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There's a version of Annapolis living where you don't have to choose between being close to everything and having room to enjoy being home. With a VA assumable loan at an interest rate of approximately 2.7%–2.8%, qualified buyers may also have an opportunity to secure financing at a rate that's difficult to find in today's market. This updated 3-bedroom, 2-bath home sits in a residential setting just minutes from downtown Annapolis, the Naval Academy, Eastport, marinas, restaurants, and shopping, while offering something that can be hard to find this close to the city: real outdoor space. Step outside and the fully fenced backyard speaks for itself. A covered deck flows to the patio and firepit, creating a space for morning coffee, dinner outside, a quiet evening by the fire, or hosting when you want to. Inside, the home balances comfort and function. Both baths feature updated showers, and the fireplace anchors the main living area. The partially finished basement with a bar adds flexible space for entertaining, movie nights, or whatever fits the way you live. The updates go beyond cosmetic. The covered deck and roofs on both the home and garage were replaced in 2021, the fence was added in 2024, and a new front porch, mailbox, walkway, and water heater followed in 2025. The detached garage adds parking and storage, with room for a workshop. Close to the energy of Annapolis, with plenty of room to unwind when you get home. VA loan assumption is subject to loan servicer approval, buyer qualification, and applicable requirements.

1033 Hyde Park Dr, Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

$1,250,000

Welcome to 313 Fourth St, one of only three townhomes at The Tecumseh and a rare opportunity in one of Eastport’s most distinctive waterfront communities. Completed in 1968 on the site of a former boatyard, The Tecumseh was Annapolis’s earliest condominium communities, designed around the boating lifestyle that continues to define Eastport today. Set directly on Spa Creek, the community offers a 72-slip private marina, waterfront swimming pool and deck, and gated private parking. Located at the corner of Fourth St and Severn Ave, this three-story, approximately 2,700-square-foot residence offers three bedrooms, two-and-a-half baths, expansive third-floor bonus space, charming Eastport street appeal, and a private rear courtyard. The main level is filled with character, featuring charming arched details, a newly renovated powder room, spacious kitchen with breakfast nook, dining area, walk-in butler’s pantry, and custom built-in bookshelves surrounding a gas fireplace. A generous living area opens through sliding glass doors to a private courtyard with a paved patio—perfect for dining al fresco and entertaining. Upstairs, the second floor features a spacious primary suite with an ensuite bath and two closets, plus two additional bedrooms that share a full bath. The third floor surprises with vaulted ceilings, a large finished bonus room, additional unfinished space, and a laundry area—offering tremendous flexibility for a home office, gym, playroom, studio, or additional living space. Just beyond your back door is direct access to The Tecumseh’s waterfront amenities, including its marina and waterfront swimming pool. For the boater, ownership also includes a 40-foot boat slip entitlement. What truly sets this property apart is the lifestyle. Step outside and you’re moments from Spa Creek and just steps from Eastport’s Restaurant Row, while downtown Annapolis is easily accessible across the bridge. Rarely available, 313 Fourth St offers the opportunity to become part of a waterfront community cherished for its history, location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

Welcome to 313 Fourth St, one of only three townhomes at The Tecumseh and a rare opportunity in one of Eastport’s most distinctive waterfront communities. Completed in 1968 on the site of a former boatyard, The Tecumseh was Annapolis’s earliest condominium communities, designed around the boating lifestyle that continues to define Eastport today. Set directly on Spa Creek, the community offers a 72-slip private marina, waterfront swimming pool and deck, and gated private parking. Located at the corner of Fourth St and Severn Ave, this three-story, approximately 2,700-square-foot residence offers three bedrooms, two-and-a-half baths, expansive third-floor bonus space, charming Eastport street appeal, and a private rear courtyard. The main level is filled with character, featuring charming arched details, a newly renovated powder room, spacious kitchen with breakfast nook, dining area, walk-in butler’s pantry, and custom built-in bookshelves surrounding a gas fireplace. A generous living area opens through sliding glass doors to a private courtyard with a paved patio—perfect for dining al fresco and entertaining. Upstairs, the second floor features a spacious primary suite with an ensuite bath and two closets, plus two additional bedrooms that share a full bath. The third floor surprises with vaulted ceilings, a large finished bonus room, additional unfinished space, and a laundry area—offering tremendous flexibility for a home office, gym, playroom, studio, or additional living space. Just beyond your back door is direct access to The Tecumseh’s waterfront amenities, including its marina and waterfront swimming pool. For the boater, ownership also includes a 40-foot boat slip entitlement. What truly sets this property apart is the lifestyle. Step outside and you’re moments from Spa Creek and just steps from Eastport’s Restaurant Row, while downtown Annapolis is easily accessible across the bridge. Rarely available, 313 Fourth St offers the opportunity to become part of a waterfront community cherished for its history, location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

313 Fourth St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$925,000

Welcome to 1422 Bay Head Road, a true Annapolis oasis offering flexible living space, thoughtful updates, and exceptional outdoor amenities. The upper level features four bedrooms, including a large primary suite with barn siding accents, a custom closet, and an ensuite bath with a large soaking tub and separate shower. Three additional bedrooms share a hall bathroom. The main level includes a living room, dining room, and kitchen with stainless steel appliances, granite countertops, and a center island. The family room features a fireplace and provides a comfortable space for everyday living and entertaining. The finished lower level adds even more versatility with a family room, custom bar, and a large storage room. Outside, enjoy professionally landscaped grounds, a large deck overlooking the built-in pool and spa, and convenient access to a full bathroom with shower. A generous yard with firepit creates an inviting setting for outdoor gatherings. The property also includes a greenhouse/chicken coop. The community offers nearby water access for kayaks and canoes and is close to parks and walking trails B&O bike trail, golf cart to Podickory Point Yacht & Beach Club. Conveniently located with easy access to Route 50, the Bay Bridge, and downtown Annapolis.

Welcome to 1422 Bay Head Road, a true Annapolis oasis offering flexible living space, thoughtful updates, and exceptional outdoor amenities. The upper level features four bedrooms, including a large primary suite with barn siding accents, a custom closet, and an ensuite bath with a large soaking tub and separate shower. Three additional bedrooms share a hall bathroom. The main level includes a living room, dining room, and kitchen with stainless steel appliances, granite countertops, and a center island. The family room features a fireplace and provides a comfortable space for everyday living and entertaining. The finished lower level adds even more versatility with a family room, custom bar, and a large storage room. Outside, enjoy professionally landscaped grounds, a large deck overlooking the built-in pool and spa, and convenient access to a full bathroom with shower. A generous yard with firepit creates an inviting setting for outdoor gatherings. The property also includes a greenhouse/chicken coop. The community offers nearby water access for kayaks and canoes and is close to parks and walking trails B&O bike trail, golf cart to Podickory Point Yacht & Beach Club. Conveniently located with easy access to Route 50, the Bay Bridge, and downtown Annapolis.

1422 Bay Head Rd, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

$1,675,000

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

5 Beds ⋅ 3 Baths

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

250 Prince George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,395,000

Highly desirable Eastport location just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

4 Beds ⋅ 5 Baths

Highly desirable Eastport location just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

1030 Boucher Ave, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$730,000

Rare opportunity in the heart of Downtown Annapolis! This spacious residence at 141 West combines modern interiors, garage parking, elevator access, and a large covered balcony overlooking West Street and Downtown Annapolis. A wall of windows fills the open living space with natural light, complemented by wide-plank wood floors and a shiplap accent wall with electric fireplace. The kitchen features quartz countertops, subway tile backsplash, stainless steel appliances, a generous island, and brand-new lighting. The primary suite features full-length windows with plantation shutters, a walk-in closet, and an upgraded bath with double vanity and large shower. A brand-new washer and dryer adds another recent update. Step outside to the private covered balcony overlooking Downtown Annapolis, an ideal spot for morning coffee, evening cocktails, and taking in the energy of West Street. A dedicated garage parking space and elevator access make downtown living exceptionally convenient. Located in the West Street Arts District, just a short walk to Main Street, City Dock, the Naval Academy, restaurants, galleries, boutiques, and the waterfront. Modern, spacious, and incredibly convenient, this is Downtown Annapolis living at its best.

Rare opportunity in the heart of Downtown Annapolis! This spacious residence at 141 West combines modern interiors, garage parking, elevator access, and a large covered balcony overlooking West Street and Downtown Annapolis. A wall of windows fills the open living space with natural light, complemented by wide-plank wood floors and a shiplap accent wall with electric fireplace. The kitchen features quartz countertops, subway tile backsplash, stainless steel appliances, a generous island, and brand-new lighting. The primary suite features full-length windows with plantation shutters, a walk-in closet, and an upgraded bath with double vanity and large shower. A brand-new washer and dryer adds another recent update. Step outside to the private covered balcony overlooking Downtown Annapolis, an ideal spot for morning coffee, evening cocktails, and taking in the energy of West Street. A dedicated garage parking space and elevator access make downtown living exceptionally convenient. Located in the West Street Arts District, just a short walk to Main Street, City Dock, the Naval Academy, restaurants, galleries, boutiques, and the waterfront. Modern, spacious, and incredibly convenient, this is Downtown Annapolis living at its best.

141 West St Unit 308, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$327,500

Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table space, making it a cozy spot for casual meals. The home features three spacious bedrooms, including a primary suite that encompasses the entire third floor, with a luxurious walk-in closet and an en-suite bathroom. Additional highlights include a laundry room, a second-floor bathroom, updated lighting, ceiling fans for added comfort, and plush carpeting that enhances the inviting atmosphere throughout. The stainless steel refrigerator and gas range, washer, dryer, carpet, and heat pump have all been updated within the past 5 years. The home has a brand-new storm door and bay window at the front of the house). Homeowners and investors will appreciate the low-maintenance lifestyle this property offers, with an association fee that includes lawn maintenance and snow removal. The community amenities include outdoor common grounds, a refreshing pool, and a fitness center. Parking is hassle-free with two parking permits included -one parking place is assigned and located directly in front of the townhome. An additional car can be parked (with permit), in the "Permit Required" spaces. The community's prime location (close proximity to Quiet Waters Park, Downtown Annapolis, the US Naval Academy, and shopping) ensures easy access to local amenities and attractions. Whether you're looking to buy or invest, this Annapolis Overlook property is a fantastic opportunity. With its blend of modern features, community amenities, and strategic location, it stands ready to deliver both comfort and value for years to come. Don't miss your chance to purchase this delightful home!

Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table space, making it a cozy spot for casual meals. The home features three spacious bedrooms, including a primary suite that encompasses the entire third floor, with a luxurious walk-in closet and an en-suite bathroom. Additional highlights include a laundry room, a second-floor bathroom, updated lighting, ceiling fans for added comfort, and plush carpeting that enhances the inviting atmosphere throughout. The stainless steel refrigerator and gas range, washer, dryer, carpet, and heat pump have all been updated within the past 5 years. The home has a brand-new storm door and bay window at the front of the house). Homeowners and investors will appreciate the low-maintenance lifestyle this property offers, with an association fee that includes lawn maintenance and snow removal. The community amenities include outdoor common grounds, a refreshing pool, and a fitness center. Parking is hassle-free with two parking permits included -one parking place is assigned and located directly in front of the townhome. An additional car can be parked (with permit), in the "Permit Required" spaces. The community's prime location (close proximity to Quiet Waters Park, Downtown Annapolis, the US Naval Academy, and shopping) ensures easy access to local amenities and attractions. Whether you're looking to buy or invest, this Annapolis Overlook property is a fantastic opportunity. With its blend of modern features, community amenities, and strategic location, it stands ready to deliver both comfort and value for years to come. Don't miss your chance to purchase this delightful home!

40 Ironstone Ct Unit B, Annapolis

Listing courtesy of RE/MAX One. Contact:

$650,000

Welcome to 953 Mastline Drive, a spacious ranch style home in the highly sought after 55+ community of Heritage Harbour. Offering just under 2,000 square feet, three bedrooms, two full bathrooms, and a two car garage, this home provides easy single level living with plenty of space to enjoy. Inside, fresh paint and brand new carpet give the home a clean, refreshed feel throughout. Generous living and dining areas offer flexibility for everyday life and entertaining, while the primary suite features its own private bathroom. Updated windows and HVAC, along with new insulation, add to the improvements already completed, allowing you to move right in while still having the opportunity to personalize the home over time. Heritage Harbour offers an impressive collection of amenities, including indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine hole golf course, community Lodge, library, and an extensive calendar of clubs, activities, and social opportunities. Shopping, dining, healthcare, and everyday conveniences are nearby, with easy access to Routes 50 and 97 and Historic Downtown Annapolis just a short drive away. Combining a spacious ranch layout, valuable updates, and the active lifestyle of one of the Annapolis area’s most established 55+ communities, 953 Mastline Drive is ready to welcome its next owner.

Welcome to 953 Mastline Drive, a spacious ranch style home in the highly sought after 55+ community of Heritage Harbour. Offering just under 2,000 square feet, three bedrooms, two full bathrooms, and a two car garage, this home provides easy single level living with plenty of space to enjoy. Inside, fresh paint and brand new carpet give the home a clean, refreshed feel throughout. Generous living and dining areas offer flexibility for everyday life and entertaining, while the primary suite features its own private bathroom. Updated windows and HVAC, along with new insulation, add to the improvements already completed, allowing you to move right in while still having the opportunity to personalize the home over time. Heritage Harbour offers an impressive collection of amenities, including indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine hole golf course, community Lodge, library, and an extensive calendar of clubs, activities, and social opportunities. Shopping, dining, healthcare, and everyday conveniences are nearby, with easy access to Routes 50 and 97 and Historic Downtown Annapolis just a short drive away. Combining a spacious ranch layout, valuable updates, and the active lifestyle of one of the Annapolis area’s most established 55+ communities, 953 Mastline Drive is ready to welcome its next owner.

953 Mastline Dr, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact:

$750,000

NEW!! $10,000 BUYER INCENTIVE BEING OFFERED. Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level, stairs, and living room feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50

4 Beds ⋅ 3 Baths

NEW!! $10,000 BUYER INCENTIVE BEING OFFERED. Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level, stairs, and living room feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50

303 Riding Ridge Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,300,000

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

5 Beds ⋅ 4 Baths

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

135 Conduit St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

78 Old Mill Bottom Rd N Unit 311, Annapolis

$699,000

Experience elevated 55+ living in the largest condominium model offered within this amenity-rich, resort-style community of Element of Old Mill. Built in 2024, this impressive third-floor corner residence offers 1,723 square feet, two spacious bedrooms, two full bathrooms and a private study that can serve as a home office, den or hobby room. The centerpiece of the open living space is the stunning gourmet kitchen with expansive kitchen island, creating a striking focal point and generous space for meal preparation, casual dining and entertaining. The kitchen is further enhanced by upgraded cabinetry, premium stainless steel appliances and stylish finishes. The is in unit laundry and ample storage in this residence. Abundant natural light complements the fresh paint, designer lighting and custom closet systems found throughout the home. Step onto the private balcony for morning coffee, outdoor dining or a quiet place to unwind. Reserved garage parking and a private storage unit add convenience and are especially desirable features within the community. Residents enjoy a low condo fee and access to tons of amenities, including pickleball courts, olympic sized pool, billiards, walking trails, a golf simulator, a putting green, a dog park, grilling areas and welcoming indoor and outdoor gathering spaces. Conveniently located near downtown Annapolis, waterfront dining, shopping and the Bay Bridge, this beautifully maintained corner condo delivers generous living space, modern style and an active, low-maintenance lifestyle.

Experience elevated 55+ living in the largest condominium model offered within this amenity-rich, resort-style community of Element of Old Mill. Built in 2024, this impressive third-floor corner residence offers 1,723 square feet, two spacious bedrooms, two full bathrooms and a private study that can serve as a home office, den or hobby room. The centerpiece of the open living space is the stunning gourmet kitchen with expansive kitchen island, creating a striking focal point and generous space for meal preparation, casual dining and entertaining. The kitchen is further enhanced by upgraded cabinetry, premium stainless steel appliances and stylish finishes. The is in unit laundry and ample storage in this residence. Abundant natural light complements the fresh paint, designer lighting and custom closet systems found throughout the home. Step onto the private balcony for morning coffee, outdoor dining or a quiet place to unwind. Reserved garage parking and a private storage unit add convenience and are especially desirable features within the community. Residents enjoy a low condo fee and access to tons of amenities, including pickleball courts, olympic sized pool, billiards, walking trails, a golf simulator, a putting green, a dog park, grilling areas and welcoming indoor and outdoor gathering spaces. Conveniently located near downtown Annapolis, waterfront dining, shopping and the Bay Bridge, this beautifully maintained corner condo delivers generous living space, modern style and an active, low-maintenance lifestyle.

78 Old Mill Bottom Rd N Unit 311, Annapolis

Listing courtesy of Samson Properties. Contact:

$379,900

Nestled in the serene community of Whispering Woods, this charming townhouse offers a perfect blend of comfort and functionality. Built in 1991, this well-maintained home boasts 1,672 square feet of inviting living space, ideal for creating lasting memories. Step inside to discover a warm and welcoming interior featuring a harmonious mix of engineered wood and neutral, freshly-painted interiors. Equipped with newer appliances and graced by maple cabinetry, recessed lighting and granite countertops, the kitchen is both practical and stylish. Newer deck overlooks a quite wooded area. Newer architectural-grade roof. The home features three generously sized bedrooms, providing ample space for relaxation and personalization. With two full bathrooms and two convenient half-bathrooms, morning routines will be a breeze. Owner's bedroom delights in an en-suite bath, dressing area and walk-in closet. Natural light floods the home through quality Andersen double-pane windows, a new front storm door, and new sliding glass doors, enhancing the inviting atmosphere and offering lovely views of the surrounding trees and woods. The full basement, complete with a connecting stairway and walkout level, presents endless possibilities. Whether you envision a bedroom, a cozy family room, a home office, or additional storage, this versatile space can be tailored to meet your needs and offers ample storage space and a workshop. The basement outside entrance opens up at grade, adding convenience, making it easy to enjoy the outdoors. The Whispering Woods community offers common grounds and tot lots/playgrounds, perfect for leisurely strolls or enjoying time outdoors. The association fee includes management, ensuring the community remains well-maintained and inviting. Parking is plentiful. The property sits on a lovely, landscaped 0.05-acre lot, providing a serene outdoor living space for gardening or relaxation. This townhouse is not just a house; it's a place to call home. With its blend of comfort, functionality, community amenities, and proximity to all major thoroughfares and the town of Annapolis, it's an exciting opportunity. Experience the tranquility of Whispering Woods and envision your future in this delightful residence.

3 Beds ⋅ 4 Baths

Nestled in the serene community of Whispering Woods, this charming townhouse offers a perfect blend of comfort and functionality. Built in 1991, this well-maintained home boasts 1,672 square feet of inviting living space, ideal for creating lasting memories. Step inside to discover a warm and welcoming interior featuring a harmonious mix of engineered wood and neutral, freshly-painted interiors. Equipped with newer appliances and graced by maple cabinetry, recessed lighting and granite countertops, the kitchen is both practical and stylish. Newer deck overlooks a quite wooded area. Newer architectural-grade roof. The home features three generously sized bedrooms, providing ample space for relaxation and personalization. With two full bathrooms and two convenient half-bathrooms, morning routines will be a breeze. Owner's bedroom delights in an en-suite bath, dressing area and walk-in closet. Natural light floods the home through quality Andersen double-pane windows, a new front storm door, and new sliding glass doors, enhancing the inviting atmosphere and offering lovely views of the surrounding trees and woods. The full basement, complete with a connecting stairway and walkout level, presents endless possibilities. Whether you envision a bedroom, a cozy family room, a home office, or additional storage, this versatile space can be tailored to meet your needs and offers ample storage space and a workshop. The basement outside entrance opens up at grade, adding convenience, making it easy to enjoy the outdoors. The Whispering Woods community offers common grounds and tot lots/playgrounds, perfect for leisurely strolls or enjoying time outdoors. The association fee includes management, ensuring the community remains well-maintained and inviting. Parking is plentiful. The property sits on a lovely, landscaped 0.05-acre lot, providing a serene outdoor living space for gardening or relaxation. This townhouse is not just a house; it's a place to call home. With its blend of comfort, functionality, community amenities, and proximity to all major thoroughfares and the town of Annapolis, it's an exciting opportunity. Experience the tranquility of Whispering Woods and envision your future in this delightful residence.

311 Sloping Woods Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$799,900

The Sellers of this home are offering a $10,000 concession for a Buyer with an acceptable offer. Use that to buy down your rate or towards closing costs! Don't delay - grab your agent and schedule a tour today! Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

The Sellers of this home are offering a $10,000 concession for a Buyer with an acceptable offer. Use that to buy down your rate or towards closing costs! Don't delay - grab your agent and schedule a tour today! Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

2691 Claibourne Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$500,000

Inside the Annapolis city limits on a cul-de-sac, this Dutch Colonial pairs four bedrooms and two full baths with a fully fenced yard and about 1,928 finished square feet on three levels. A bedroom and full bath on the main level give guests their own space or make room for a home office, and three more bedrooms and a second full bath are upstairs. The fully finished basement adds room for a rec room, gym, or office. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. Out back, a deck steps down to the fenced yard, and a shed adds storage. The driveway parks two cars. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, the restaurants of Eastport, the Annapolis Maritime Museum, and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore, and the Eastern Shore within reach, for the commute or for the weekend. Ask your agent about a lender closing-cost credit of up to $2,000 for applications by December 31, 2026, and no lender fees on VA loans.

4 Beds ⋅ 2 Baths

Inside the Annapolis city limits on a cul-de-sac, this Dutch Colonial pairs four bedrooms and two full baths with a fully fenced yard and about 1,928 finished square feet on three levels. A bedroom and full bath on the main level give guests their own space or make room for a home office, and three more bedrooms and a second full bath are upstairs. The fully finished basement adds room for a rec room, gym, or office. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. Out back, a deck steps down to the fenced yard, and a shed adds storage. The driveway parks two cars. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, the restaurants of Eastport, the Annapolis Maritime Museum, and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore, and the Eastern Shore within reach, for the commute or for the weekend. Ask your agent about a lender closing-cost credit of up to $2,000 for applications by December 31, 2026, and no lender fees on VA loans.

1017 Hyde Park Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$264,900

This exceptional 2nd level unit, ideally located in North Green Condos offers a harmonious blend of contemporary design and modern amenities. Spanning 1,082 square feet, this well-maintained condo features two spacious bedrooms and two full bathrooms, including a primary bath with walk-in shower. The open floor plan enhances the living space, complemented by wood floors, dining room and a bright breakfast area that invites natural light. The kitchen is equipped with 42inch cabinets, stone countertops, and NEW stainless-steel appliances, including a built-in microwave, dishwasher, and electric oven/range, ensuring a seamless cooking experience. You will appreciate the new luxury carpet in bedrooms and fresh paint throughout. Additional conveniences include in-unit laundry washer and dryer, as well as a walk-in closet for ample storage. Residents can enjoy community amenities such as an outdoor pool, patio area, and beautifully maintained common grounds. The property is surrounded by sidewalks, public transport and fitness center amenities. Situated in a vibrant neighborhood, North Green Condos is conveniently located near shopping centers and local parks, providing recreational opportunities for outdoor enthusiasts. The community is well-served by public services, pet friendly, and is in proximity to schools and recreation facilities, making it a desirable location for those seeking a balanced lifestyle. The association fee covers essential services, including maintenance, building insurance, water/sewer and trash removal, ensuring worry-free living. This property represents an excellent opportunity for those seeking a modern, well-appointed home to enjoy the historic maritime experience of Annapolis. Just minutes from the United States Naval Academy and downtown city dock.

This exceptional 2nd level unit, ideally located in North Green Condos offers a harmonious blend of contemporary design and modern amenities. Spanning 1,082 square feet, this well-maintained condo features two spacious bedrooms and two full bathrooms, including a primary bath with walk-in shower. The open floor plan enhances the living space, complemented by wood floors, dining room and a bright breakfast area that invites natural light. The kitchen is equipped with 42inch cabinets, stone countertops, and NEW stainless-steel appliances, including a built-in microwave, dishwasher, and electric oven/range, ensuring a seamless cooking experience. You will appreciate the new luxury carpet in bedrooms and fresh paint throughout. Additional conveniences include in-unit laundry washer and dryer, as well as a walk-in closet for ample storage. Residents can enjoy community amenities such as an outdoor pool, patio area, and beautifully maintained common grounds. The property is surrounded by sidewalks, public transport and fitness center amenities. Situated in a vibrant neighborhood, North Green Condos is conveniently located near shopping centers and local parks, providing recreational opportunities for outdoor enthusiasts. The community is well-served by public services, pet friendly, and is in proximity to schools and recreation facilities, making it a desirable location for those seeking a balanced lifestyle. The association fee covers essential services, including maintenance, building insurance, water/sewer and trash removal, ensuring worry-free living. This property represents an excellent opportunity for those seeking a modern, well-appointed home to enjoy the historic maritime experience of Annapolis. Just minutes from the United States Naval Academy and downtown city dock.

300 Hilltop Ln Unit 300E, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$449,000

Back On The Market Through No Fault Of The Seller!! A wonderful second opportunity for buyers who missed it the first time!! Beautifully updated and move-in ready in an ideal Annapolis location! HVAC, ROOF, & HOT WATER HEATER ALL REPLACED APPROX. 2021. This inviting home has been thoughtfully refreshed with updated kitchen finishes, new flooring, fresh interior paint and beautifully updated bathrooms, creating a bright, fresh feel throughout. The main level offers a comfortable, functional layout with generous living and entertaining spaces and a beautifully updated kitchen at the heart of the home. Upstairs, spacious bedrooms and refreshed bathrooms continue the clean, updated feel. Enjoy additional living space and flexibility throughout the home, along with outdoor space perfect for relaxing or entertaining. Ideally located in Annapolis just minutes from Quiet Waters Park, downtown Annapolis, Eastport, shopping, dining and major commuter routes. With so many of the important updates already completed, this home offers an incredible opportunity to move right in and enjoy everything the Annapolis lifestyle has to offer!

Back On The Market Through No Fault Of The Seller!! A wonderful second opportunity for buyers who missed it the first time!! Beautifully updated and move-in ready in an ideal Annapolis location! HVAC, ROOF, & HOT WATER HEATER ALL REPLACED APPROX. 2021. This inviting home has been thoughtfully refreshed with updated kitchen finishes, new flooring, fresh interior paint and beautifully updated bathrooms, creating a bright, fresh feel throughout. The main level offers a comfortable, functional layout with generous living and entertaining spaces and a beautifully updated kitchen at the heart of the home. Upstairs, spacious bedrooms and refreshed bathrooms continue the clean, updated feel. Enjoy additional living space and flexibility throughout the home, along with outdoor space perfect for relaxing or entertaining. Ideally located in Annapolis just minutes from Quiet Waters Park, downtown Annapolis, Eastport, shopping, dining and major commuter routes. With so many of the important updates already completed, this home offers an incredible opportunity to move right in and enjoy everything the Annapolis lifestyle has to offer!

150 Quiet Waters Pl, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$9,500,000

Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!

6 Beds ⋅ 10 Baths

Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!

3285 Harness Creek Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$995,000

Experience the best of downtown Annapolis living from this exceptional corner residence in highly sought-after Acton’s Landing. This 2 bedroom, with an extra den unit, offers nearly 2,000 square feet of beautifully designed living space. This extraordinary condominium combines the ease of maintenance-free living with a rare feature that truly sets it apart: its own exterior entrance. Step directly outside and begin enjoying the restaurants, shops, waterfront, events, and unmistakable charm of downtown Annapolis without ever having to walk through the building. The private exterior entrance also provides exceptional convenience for guests, particularly after concierge hours, allowing them to arrive directly at your door. Inside, the spacious, open-concept floor plan has been freshly painted and features brand-new carpeting, abundant natural light, and a wall of windows overlooking the outdoor patio area. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, stainless steel appliances—including gas cooktop and a new refrigerator —and a generous island/breakfast bar that opens seamlessly to the main living area. The thoughtfully designed layout provides excellent separation between the two expansive bedroom suites. The primary suite features two closets, including a walk-in, along with a spacious private bath complete with a separate soaking tub. On the opposite side of the residence, the second bedroom offers its own en-suite bath, creating an ideal private retreat for overnight guests. A separate den/office provides valuable additional living space and offers the flexibility to serve as a home office, library, media room, or occasional guest space. A conveniently located powder room makes entertaining especially easy. Adding to the exceptional convenience are two garage parking spaces located just steps from the residence, along with an owned private storage unit—valuable amenities for downtown Annapolis living. Acton’s Landing further enhances the lifestyle with a fitness center, library, recreation/community room, beautifully landscaped courtyard, and concierge service. And when you are ready to venture out, downtown Annapolis is right outside your door. Few residences offer this combination of nearly 2,000 square feet, two garage parking spaces, private storage, luxury amenities, and the rare convenience of a direct entrance/exit with its own outdoor, covered patio—all within walking distance of everything that makes Annapolis such an extraordinary place to live. This is more than simply a downtown condo; it is an opportunity to enjoy the Annapolis lifestyle with the space, comfort, convenience, and accessibility of a true luxury residence.

2 Beds ⋅ 3 Baths

Experience the best of downtown Annapolis living from this exceptional corner residence in highly sought-after Acton’s Landing. This 2 bedroom, with an extra den unit, offers nearly 2,000 square feet of beautifully designed living space. This extraordinary condominium combines the ease of maintenance-free living with a rare feature that truly sets it apart: its own exterior entrance. Step directly outside and begin enjoying the restaurants, shops, waterfront, events, and unmistakable charm of downtown Annapolis without ever having to walk through the building. The private exterior entrance also provides exceptional convenience for guests, particularly after concierge hours, allowing them to arrive directly at your door. Inside, the spacious, open-concept floor plan has been freshly painted and features brand-new carpeting, abundant natural light, and a wall of windows overlooking the outdoor patio area. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, stainless steel appliances—including gas cooktop and a new refrigerator —and a generous island/breakfast bar that opens seamlessly to the main living area. The thoughtfully designed layout provides excellent separation between the two expansive bedroom suites. The primary suite features two closets, including a walk-in, along with a spacious private bath complete with a separate soaking tub. On the opposite side of the residence, the second bedroom offers its own en-suite bath, creating an ideal private retreat for overnight guests. A separate den/office provides valuable additional living space and offers the flexibility to serve as a home office, library, media room, or occasional guest space. A conveniently located powder room makes entertaining especially easy. Adding to the exceptional convenience are two garage parking spaces located just steps from the residence, along with an owned private storage unit—valuable amenities for downtown Annapolis living. Acton’s Landing further enhances the lifestyle with a fitness center, library, recreation/community room, beautifully landscaped courtyard, and concierge service. And when you are ready to venture out, downtown Annapolis is right outside your door. Few residences offer this combination of nearly 2,000 square feet, two garage parking spaces, private storage, luxury amenities, and the rare convenience of a direct entrance/exit with its own outdoor, covered patio—all within walking distance of everything that makes Annapolis such an extraordinary place to live. This is more than simply a downtown condo; it is an opportunity to enjoy the Annapolis lifestyle with the space, comfort, convenience, and accessibility of a true luxury residence.

66 Franklin St Unit 102, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$2,795,000

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

113 Bay Dr, Annapolis

Listing courtesy of Krauss Real Property Brokerage. Contact:

2104 Chesapeake Harbour Dr E Unit 202, Annapolis

$669,000

Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and high-end upgrades from top to bottom. The open, light-filled layout features stylish new LVP flooring (Oct 2024) and contemporary lighting throughout (2024). Cook and entertain in the updated kitchen with custom cabinetry and quartz countertops (Dec 2024), plus brand-new appliances (Jan 2025). Relax in the primary suite with its custom Closet America walk-in closet (Sept 2025). Living in Chesapeake Harbour gives you direct access to a deep-water marina, private beach, pools, tennis courts, 24/7 security, and an on-site waterfront restaurant, all just minutes from historic Downtown Annapolis.

Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and high-end upgrades from top to bottom. The open, light-filled layout features stylish new LVP flooring (Oct 2024) and contemporary lighting throughout (2024). Cook and entertain in the updated kitchen with custom cabinetry and quartz countertops (Dec 2024), plus brand-new appliances (Jan 2025). Relax in the primary suite with its custom Closet America walk-in closet (Sept 2025). Living in Chesapeake Harbour gives you direct access to a deep-water marina, private beach, pools, tennis courts, 24/7 security, and an on-site waterfront restaurant, all just minutes from historic Downtown Annapolis.

2104 Chesapeake Harbour Dr E Unit 202, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$275,000

NEW PRICE and MOVE-IN READY! Top-floor 3 bed, 2 full bath condo in Fairwinds of Annapolis. Offering low-maintenance living and an unbeatable location just minutes from Downtown Annapolis. This large floorplan home features a bright, open layout and a private balcony. The updated kitchen features new flooring, gas cooking, ample cabinet storage, and a new refrigerator. Bathrooms have been refreshed with newly installed floors and lighting. The HVAC system was replaced in 2022, providing added peace of mind. The spacious primary bedroom features a private full bath and two closets, including a large walk-in closet. Two generously sized secondary bedrooms share an additional full bath. Enjoy the convenience of gas heating, hot water, and cooking, along with access to the community pool and tennis courts. Reserved off-street parking is available for a fee through the condo association. This new price and location are hard to beat! Walking distance to grocery stores, coffee shops, and restaurants. Easy access to shopping, Downtown Annapolis, Eastport, the Naval Academy, and major commuter routes. Schedule a tour today!

NEW PRICE and MOVE-IN READY! Top-floor 3 bed, 2 full bath condo in Fairwinds of Annapolis. Offering low-maintenance living and an unbeatable location just minutes from Downtown Annapolis. This large floorplan home features a bright, open layout and a private balcony. The updated kitchen features new flooring, gas cooking, ample cabinet storage, and a new refrigerator. Bathrooms have been refreshed with newly installed floors and lighting. The HVAC system was replaced in 2022, providing added peace of mind. The spacious primary bedroom features a private full bath and two closets, including a large walk-in closet. Two generously sized secondary bedrooms share an additional full bath. Enjoy the convenience of gas heating, hot water, and cooking, along with access to the community pool and tennis courts. Reserved off-street parking is available for a fee through the condo association. This new price and location are hard to beat! Walking distance to grocery stores, coffee shops, and restaurants. Easy access to shopping, Downtown Annapolis, Eastport, the Naval Academy, and major commuter routes. Schedule a tour today!

142 Georgetown Rd Unit 9, Annapolis

Listing courtesy of Redfin Corp. Contact:

$1,875,000

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$475,000

SELLER PROVIDING A CREDIT FOR 1 YEAR'S WORTH OF CONDO FEES ($10,000) AT CLOSING IN ADDITION TO 2-1 BUYDOWN FINANCING. ELEVATOR ACCESS TO COVETED SPACE #2 IN THE CONDO GARAGE CONVEYS!!! Spanning 1,588 square feet, this beautifully maintained residence features two spacious bedrooms and two full bathrooms adjoining the brightly lit sunroom providing ample space for relaxation and entertaining. Step inside to discover a gourmet kitchen that is a chef's dream, complete with cherry cabinetry, granite countertops, natural gas cooktop, a built-in microwave and wall oven, all designed to inspire culinary creativity. The open layout flows effortlessly into a cozy dining area and a bright breakfast nook, perfect for enjoying morning coffee or hosting intimate gatherings. The living space is adorned with plush carpeting and ceramic tile, creating a warm and inviting atmosphere throughout. The primary suite is a true retreat, featuring 2 walk-in closets and a luxurious bathroom equipped with 2 separate vanities and both a stall shower and tub, ensuring a spa-like experience at home. Additional interior highlights include 9' ceilings and all window treatments that enhance privacy while allowing natural light to fill the space. Step outside to enjoy the meticulously landscaped grounds, complete with extensive hardscaping, irrigated landscaping and additional outdoor parking for guests. This 55+ adult community boasts an array of amenities designed for an active lifestyle, including a fitness center, tennis/pickleball courts and an executive par 3 nine hole golf course complete with club house and dining facility. For those who enjoy socializing, the waterfront clubhouse known as The Lodge offers indoor and outdoor pools plus a wide range of clubs, social activities, and creative spaces fostering a true sense of community. Condo and HOA fees include access to all community amenities, making for easy, low maintenance living. Water enthusiasts will appreciate the private access to the South River, complete with a community dock and multiple slips for boating adventures. Whether you prefer a leisurely day by the water, pool or an invigorating game of pickleball, golf or tennis, this community caters to all interests. With convenient transportation options and a dedicated parking space in the garage, this property ensures ease of access to historic downtown Annapolis with it's intown dining, shopping, cultural events and activities. Experience the perfect blend of luxury, comfort, and community in this exceptional residence, where every detail has been thoughtfully curated to enhance your lifestyle. Embrace the opportunity to make this exceptional property your own.

SELLER PROVIDING A CREDIT FOR 1 YEAR'S WORTH OF CONDO FEES ($10,000) AT CLOSING IN ADDITION TO 2-1 BUYDOWN FINANCING. ELEVATOR ACCESS TO COVETED SPACE #2 IN THE CONDO GARAGE CONVEYS!!! Spanning 1,588 square feet, this beautifully maintained residence features two spacious bedrooms and two full bathrooms adjoining the brightly lit sunroom providing ample space for relaxation and entertaining. Step inside to discover a gourmet kitchen that is a chef's dream, complete with cherry cabinetry, granite countertops, natural gas cooktop, a built-in microwave and wall oven, all designed to inspire culinary creativity. The open layout flows effortlessly into a cozy dining area and a bright breakfast nook, perfect for enjoying morning coffee or hosting intimate gatherings. The living space is adorned with plush carpeting and ceramic tile, creating a warm and inviting atmosphere throughout. The primary suite is a true retreat, featuring 2 walk-in closets and a luxurious bathroom equipped with 2 separate vanities and both a stall shower and tub, ensuring a spa-like experience at home. Additional interior highlights include 9' ceilings and all window treatments that enhance privacy while allowing natural light to fill the space. Step outside to enjoy the meticulously landscaped grounds, complete with extensive hardscaping, irrigated landscaping and additional outdoor parking for guests. This 55+ adult community boasts an array of amenities designed for an active lifestyle, including a fitness center, tennis/pickleball courts and an executive par 3 nine hole golf course complete with club house and dining facility. For those who enjoy socializing, the waterfront clubhouse known as The Lodge offers indoor and outdoor pools plus a wide range of clubs, social activities, and creative spaces fostering a true sense of community. Condo and HOA fees include access to all community amenities, making for easy, low maintenance living. Water enthusiasts will appreciate the private access to the South River, complete with a community dock and multiple slips for boating adventures. Whether you prefer a leisurely day by the water, pool or an invigorating game of pickleball, golf or tennis, this community caters to all interests. With convenient transportation options and a dedicated parking space in the garage, this property ensures ease of access to historic downtown Annapolis with it's intown dining, shopping, cultural events and activities. Experience the perfect blend of luxury, comfort, and community in this exceptional residence, where every detail has been thoughtfully curated to enhance your lifestyle. Embrace the opportunity to make this exceptional property your own.

940 Astern Way Unit 112, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$378,900

BRAND-NEW HVAC SYSTEM—ONLY ONE MONTH OLD! Welcome to 1133 Lake Heron Drive, Unit 2B, a beautifully maintained second-level condo situated in one of the neighborhood’s most desirable locations. Tucked beside a large, open grassy field, this home offers a rare sense of privacy with peaceful views of nature from the side windows. Inside, you’ll find high-quality hardwood floors, a beautifully working wood-burning fireplace that creates a warm and inviting focal point, an updated kitchen, and marble bathroom sinks. Enjoy outdoor living from not one, but two balconies—one in the front and one in the back—providing wonderful spaces to relax, enjoy your morning coffee, or unwind at the end of the day. Step outside and enjoy beautiful, scenic jogging and walking paths throughout the community, surrounded by peaceful natural scenery. Community amenities also include an outdoor swimming pool and workout room, making it easy to stay active and enjoy the neighborhood without leaving home. The second-level setting provides an elevated outlook, while the location alongside the open green space makes this unit particularly special. Conveniently located in Annapolis, with easy access to everything the area has to offer, including shopping, dining, recreation, and the charm of downtown Annapolis. A wonderful combination of location, updates, amenities, outdoor space, and natural surroundings!

BRAND-NEW HVAC SYSTEM—ONLY ONE MONTH OLD! Welcome to 1133 Lake Heron Drive, Unit 2B, a beautifully maintained second-level condo situated in one of the neighborhood’s most desirable locations. Tucked beside a large, open grassy field, this home offers a rare sense of privacy with peaceful views of nature from the side windows. Inside, you’ll find high-quality hardwood floors, a beautifully working wood-burning fireplace that creates a warm and inviting focal point, an updated kitchen, and marble bathroom sinks. Enjoy outdoor living from not one, but two balconies—one in the front and one in the back—providing wonderful spaces to relax, enjoy your morning coffee, or unwind at the end of the day. Step outside and enjoy beautiful, scenic jogging and walking paths throughout the community, surrounded by peaceful natural scenery. Community amenities also include an outdoor swimming pool and workout room, making it easy to stay active and enjoy the neighborhood without leaving home. The second-level setting provides an elevated outlook, while the location alongside the open green space makes this unit particularly special. Conveniently located in Annapolis, with easy access to everything the area has to offer, including shopping, dining, recreation, and the charm of downtown Annapolis. A wonderful combination of location, updates, amenities, outdoor space, and natural surroundings!

1133 Lake Heron Dr Unit 2B, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

$525,000

Price Reduction. Gorgeous 4 level townhome situated on a premium, landscaped lot with water views. Every level highlights the connection to nature and privacy in this well-maintained, thoughtfully designed home. The ground level features a one car garage with storage shelves and a spa-like ensuite bedroom that leads to a private screened porch and fenced backyard. Perfect for guests, this space evokes relaxation and privacy. The main level offers a spacious family room, a gourmet kitchen, and large dining area that leads to a deck with views of the backyard oasis. Options for entertaining here are endless, with comfortable spaces for all to enjoy. The bedroom level offers a unique primary bedroom suite with ample closet space, sitting room/second bedroom, and upgraded primary bath with a luxury shower, double vanity, and soaking tub. The water view is prominent on this level. The bonus loft level provides an additional bedroom or office/flex space and a full bath. The wooded walking trail that leads to the community pier is a short walk away, providing stunning views and water access. With hardwood flooring on each level this home shows exceptionally well and is just waiting for its next occupants. Welcome Home!

Price Reduction. Gorgeous 4 level townhome situated on a premium, landscaped lot with water views. Every level highlights the connection to nature and privacy in this well-maintained, thoughtfully designed home. The ground level features a one car garage with storage shelves and a spa-like ensuite bedroom that leads to a private screened porch and fenced backyard. Perfect for guests, this space evokes relaxation and privacy. The main level offers a spacious family room, a gourmet kitchen, and large dining area that leads to a deck with views of the backyard oasis. Options for entertaining here are endless, with comfortable spaces for all to enjoy. The bedroom level offers a unique primary bedroom suite with ample closet space, sitting room/second bedroom, and upgraded primary bath with a luxury shower, double vanity, and soaking tub. The water view is prominent on this level. The bonus loft level provides an additional bedroom or office/flex space and a full bath. The wooded walking trail that leads to the community pier is a short walk away, providing stunning views and water access. With hardwood flooring on each level this home shows exceptionally well and is just waiting for its next occupants. Welcome Home!

218 Wintergull Ln, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,250,000

Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5-minute walk from the Naval Academy Marine Corps Stadium, this beautifully renovated 2026 home offers the rare combination of privacy, convenience and Annapolis charm. Set on a generous .598-acre tract, the property backs-up to Tawes Gardens, that gives the home a tranquil and private setting. The home has been completely renovated in 2026, both inside and out, offering thoughtful updates while maintaining the integrity of the community. Enjoy the best of Annapolis, all within walking distance or true city living just a short drive away. Welcome home to 700 Miller Road. Ask about great below market seller financing.

Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5-minute walk from the Naval Academy Marine Corps Stadium, this beautifully renovated 2026 home offers the rare combination of privacy, convenience and Annapolis charm. Set on a generous .598-acre tract, the property backs-up to Tawes Gardens, that gives the home a tranquil and private setting. The home has been completely renovated in 2026, both inside and out, offering thoughtful updates while maintaining the integrity of the community. Enjoy the best of Annapolis, all within walking distance or true city living just a short drive away. Welcome home to 700 Miller Road. Ask about great below market seller financing.

700 Miller Rd, Annapolis

Listing courtesy of Cottage Street Realty LLC. Contact:

$1,495,000

A significant price reduction has been made on this stunning home! Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek and parking on both sides of street, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.