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Price Reduction! Seller says to bring all offers! Built by Captain Beriah Maybury in 1772 and known as the Kings' Arms Tavern, this Historically designated property is a MUST SEE! This Five-Bay wide brick Single Family Home sits on top of a high scored stone foundation. 9.5 foot ceilings illuminated by nearly floor to ceiling windows showcase a lovely Library with built-In Bookcases and a wood burning Fireplace; a Two Room Parlor, also with a wood burning Fireplace; an addition erected possibly as early as the 1830's includes a large Dining Room with high domed ceiling, a kitchen and a small porch. The upstairs 4 Bedrooms, 3 with their own wood burning Fireplace, wood floors, 2 full Baths and laundry provide plenty of room! The partially finished basement, most recently used as a woodworking shop, has a separate street entrance and could possibly be reimagined as additional living space. The long, gated driveway leads to 2 garage spaces and parking for an additional 6 cars and a charming English garden and patio area. Furnace chimney recently relined. This home is being sold AS IS, but has great bones. Bring your own TLC. Call Listing Agent with questions.

41 Cornhill St, Annapolis

Listing courtesy of Expert Realty, LLC.. Contact:

Enjoy urban living at 285 West Street #15! This stunning property offers a stylish way to embrace the best of downtown Annapolis in a modern townhome with an elevator and rooftop deck. Step outside and enjoy the city’s energy—shops, restaurants, the waterfront, and cultural attractions are all just a short stroll away—while still savoring the comfort of a private, lock-and-leave retreat. Built by Bozzuto in 2020, this four-bedroom, four-and-a-half-bath home features an open, light-filled layout designed for both everyday living and entertaining. The open floor plan on the main level includes the living room with spacious seating area and fireplace, a dining area, and a classic all white gourmet kitchen anchored by an island with ample seating, high-end appliances, and a built-in sideboard with beverage center. Upstairs, the primary suite offers two walk-in closets and a spa-like bath with double vanities, and a large tiled shower. An additional bedrooms with ensuite bath and conveniently located laundry room complete the this level. Head upstairs to the top floor via the stairs or elevator to enjoy the inviting family room, guest bedroom and enviable rooftop deck with double sided fireplace and sunshade, an incredible retreat for relaxing and entertaining on a beautiful evening. The entry level provides a flexible bedroom or office with full bath and boasts heated floors for added comfort. Rounding out the appeal is a two-car garage, plenty of storage and a plethora of upgrades and curated finishes throughout. Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

$1,450,000

4 Beds ⋅ 5 Baths

Enjoy urban living at 285 West Street #15! This stunning property offers a stylish way to embrace the best of downtown Annapolis in a modern townhome with an elevator and rooftop deck. Step outside and enjoy the city’s energy—shops, restaurants, the waterfront, and cultural attractions are all just a short stroll away—while still savoring the comfort of a private, lock-and-leave retreat. Built by Bozzuto in 2020, this four-bedroom, four-and-a-half-bath home features an open, light-filled layout designed for both everyday living and entertaining. The open floor plan on the main level includes the living room with spacious seating area and fireplace, a dining area, and a classic all white gourmet kitchen anchored by an island with ample seating, high-end appliances, and a built-in sideboard with beverage center. Upstairs, the primary suite offers two walk-in closets and a spa-like bath with double vanities, and a large tiled shower. An additional bedrooms with ensuite bath and conveniently located laundry room complete the this level. Head upstairs to the top floor via the stairs or elevator to enjoy the inviting family room, guest bedroom and enviable rooftop deck with double sided fireplace and sunshade, an incredible retreat for relaxing and entertaining on a beautiful evening. The entry level provides a flexible bedroom or office with full bath and boasts heated floors for added comfort. Rounding out the appeal is a two-car garage, plenty of storage and a plethora of upgrades and curated finishes throughout. Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

285 West St Unit 15, Annapolis

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

Selling Office: RE/MAX Leading Edge.

$1,245,000

Welcome to 704 Roane Hollow Lane! A covered front porch leads into a beautifully appointed foyer, where custom built-in shelving introduces the home’s thoughtful design and attention to detail. Flanking the entry, a private study with French doors and custom accent wall provides an ideal work-from-home retreat, while the formal living room offers an elegant space for gathering. Wide-plank flooring flows seamlessly throughout the main level, complemented by plantation shutters, fresh designer paint, and curated lighting that create a cohesive and sophisticated aesthetic. The main level is thoughtfully designed for both everyday living and elevated entertaining. At the heart of the home, the gourmet kitchen is designed to impress, featuring an expansive center island, quartz countertops, custom tile backsplash, shaker-style cabinetry, premium stainless steel appliances, wall oven, and a six-burner gas range, all complemented by a spacious pantry. The adjoining family room showcases a coffered ceiling and wood-burning fireplace, creating a warm yet refined setting, while the formal dining space is perfectly suited for entertaining. A re-screened porch with a ceiling fan extends the living space outdoors, offering a seamless indoor-outdoor lifestyle. A well-appointed powder room and a thoughtfully designed mudroom, conveniently connected to the attached two-car garage with epoxy-coated floors, offer both functionality and everyday ease. Upstairs, the primary suite is a true retreat, highlighted by a cathedral ceiling and dual walk-in closets, each thoughtfully designed with custom built-ins. The primary bath features dual sink vanities, oversized shower with glass door and a separate soaking tub area. Three additional bedrooms, share a beautifully updated hall bath. A conveniently located upper-level laundry room enhances everyday ease. The fully finished lower level offers exceptional versatility, featuring a fifth bedroom, expansive recreation and game room, a renovated full bath with a walk-in shower, and a dedicated storage room. A custom-built, multi-use cooler/refrigerator adds a unique and highly functional element, ideal for a florist, wine collector, caterer, or additional food storage. The exterior is equally impressive, featuring a recently constructed detached garage designed with dual garage doors for convenient pass-through access. Extensive hardscaping, a private hot tub patio, and a fully fenced backyard create a beautifully curated outdoor setting, while the classic stone patio, fire pit, and basketball court offer endless opportunities for recreation and entertaining. Tucked within a quiet enclave of homes, this property offers a rare sense of privacy with peaceful, wooded views to the rear. Its prime location provides easy access to downtown Annapolis, the Annapolis Town Center, and Routes 50 and 97, making commuting and everyday conveniences effortless. With thoughtful upgrades throughout and a seamless blend of style, comfort, and functionality, this home offers an exceptional living experience.

5 Beds ⋅ 4 Baths

Welcome to 704 Roane Hollow Lane! A covered front porch leads into a beautifully appointed foyer, where custom built-in shelving introduces the home’s thoughtful design and attention to detail. Flanking the entry, a private study with French doors and custom accent wall provides an ideal work-from-home retreat, while the formal living room offers an elegant space for gathering. Wide-plank flooring flows seamlessly throughout the main level, complemented by plantation shutters, fresh designer paint, and curated lighting that create a cohesive and sophisticated aesthetic. The main level is thoughtfully designed for both everyday living and elevated entertaining. At the heart of the home, the gourmet kitchen is designed to impress, featuring an expansive center island, quartz countertops, custom tile backsplash, shaker-style cabinetry, premium stainless steel appliances, wall oven, and a six-burner gas range, all complemented by a spacious pantry. The adjoining family room showcases a coffered ceiling and wood-burning fireplace, creating a warm yet refined setting, while the formal dining space is perfectly suited for entertaining. A re-screened porch with a ceiling fan extends the living space outdoors, offering a seamless indoor-outdoor lifestyle. A well-appointed powder room and a thoughtfully designed mudroom, conveniently connected to the attached two-car garage with epoxy-coated floors, offer both functionality and everyday ease. Upstairs, the primary suite is a true retreat, highlighted by a cathedral ceiling and dual walk-in closets, each thoughtfully designed with custom built-ins. The primary bath features dual sink vanities, oversized shower with glass door and a separate soaking tub area. Three additional bedrooms, share a beautifully updated hall bath. A conveniently located upper-level laundry room enhances everyday ease. The fully finished lower level offers exceptional versatility, featuring a fifth bedroom, expansive recreation and game room, a renovated full bath with a walk-in shower, and a dedicated storage room. A custom-built, multi-use cooler/refrigerator adds a unique and highly functional element, ideal for a florist, wine collector, caterer, or additional food storage. The exterior is equally impressive, featuring a recently constructed detached garage designed with dual garage doors for convenient pass-through access. Extensive hardscaping, a private hot tub patio, and a fully fenced backyard create a beautifully curated outdoor setting, while the classic stone patio, fire pit, and basketball court offer endless opportunities for recreation and entertaining. Tucked within a quiet enclave of homes, this property offers a rare sense of privacy with peaceful, wooded views to the rear. Its prime location provides easy access to downtown Annapolis, the Annapolis Town Center, and Routes 50 and 97, making commuting and everyday conveniences effortless. With thoughtful upgrades throughout and a seamless blend of style, comfort, and functionality, this home offers an exceptional living experience.

704 Roane Hollow Ln, Annapolis

Listing courtesy of Washington Fine Properties. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$1,100,000

Enjoy luxury one-level living in the heart of downtown Annapolis in this unique, penthouse condo with a one-of-a-kind, beautifully landscaped, expansive terrace. The condo includes two bedrooms plus an office or 3rd bedroom, 2.5 bathrooms and an open floor plan. Leave the cars in your secure two garage parking spaces, and walk to dinner, the waterfront, the Naval Academy, concerts, Maryland Hall for the Arts, and City Dock. This condo offers a seamless, turnkey lifestyle anchored by an open, light-filled floor plan enhanced by floor-to-ceiling windows and premium finishes throughout. The private terrace is an inviting outdoor retreat ideal for dining, entertaining, or simply relaxing under the retractable awnings on sunny afternoons. The gourmet kitchen is designed for both everyday living and effortless entertaining and features high-end appliances, gas cooking, a large island with ample work space, and dedicated wine storage. A sun-filled office that doubles as a 3rd bedroom, provides the perfect work-from-home space, while the spacious primary suite and second bedroom—thoughtfully positioned on the opposite side of the residence for added privacy—provide exceptional comfort for owners and guests alike. Welcome to 141 West Street where one level luxury living, a private penthouse terrace, two garage parking spaces, and a walk-everywhere location come together to offer benefits that are difficult to duplicate anywhere else in downtown Annapolis.

2 Beds ⋅ 3 Baths

Enjoy luxury one-level living in the heart of downtown Annapolis in this unique, penthouse condo with a one-of-a-kind, beautifully landscaped, expansive terrace. The condo includes two bedrooms plus an office or 3rd bedroom, 2.5 bathrooms and an open floor plan. Leave the cars in your secure two garage parking spaces, and walk to dinner, the waterfront, the Naval Academy, concerts, Maryland Hall for the Arts, and City Dock. This condo offers a seamless, turnkey lifestyle anchored by an open, light-filled floor plan enhanced by floor-to-ceiling windows and premium finishes throughout. The private terrace is an inviting outdoor retreat ideal for dining, entertaining, or simply relaxing under the retractable awnings on sunny afternoons. The gourmet kitchen is designed for both everyday living and effortless entertaining and features high-end appliances, gas cooking, a large island with ample work space, and dedicated wine storage. A sun-filled office that doubles as a 3rd bedroom, provides the perfect work-from-home space, while the spacious primary suite and second bedroom—thoughtfully positioned on the opposite side of the residence for added privacy—provide exceptional comfort for owners and guests alike. Welcome to 141 West Street where one level luxury living, a private penthouse terrace, two garage parking spaces, and a walk-everywhere location come together to offer benefits that are difficult to duplicate anywhere else in downtown Annapolis.

141 West St Unit 401, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

This beautifully updated home in Annapolis offers the perfect blend of comfort, style, and convenience, located just moments from downtown Annapolis and near the Navy-Marine Corps Memorial Stadium. Featuring 4 bedrooms, 3 full baths, and 1 half bath across three finished levels, this spacious property is designed for both everyday living and entertaining. Situated on a large lot backing to a wooded area, the property offers exceptional privacy and a peaceful outdoor setting. The upper level includes a spacious primary suite with a private deck and ensuite bath with soaking tub, along with two additional bedrooms, a full hall bath, and convenient upper-level laundry. The fully finished lower level is perfect for hosting guests offering a large recreation room, additional bedroom, full bath, second laundry, and direct walk-out access to the backyard. The main level features multiple living spaces, a flexible front sitting room, and a beautifully appointed chef’s kitchen complete with a Wolf range, flattop cooking surface, wine fridge, peninsula seating, and generous dining space. Step outside to enjoy the fully fenced backyard featuring a large deck, lower patio, and multiple outdoor seating areas ideal for relaxing or entertaining. Additional highlights include large sized shed, driveway parking for up to 3 vehicles, and ample street parking. Don't miss this opportunity to own a spacious, thoughtfully designed home in a sought-after Annapolis location. Qualified military and civilian buyers may be eligible to assume the seller’s existing low-interest VA loan, offering significant financing advantages.

$930,000

4 Beds ⋅ 4 Baths

This beautifully updated home in Annapolis offers the perfect blend of comfort, style, and convenience, located just moments from downtown Annapolis and near the Navy-Marine Corps Memorial Stadium. Featuring 4 bedrooms, 3 full baths, and 1 half bath across three finished levels, this spacious property is designed for both everyday living and entertaining. Situated on a large lot backing to a wooded area, the property offers exceptional privacy and a peaceful outdoor setting. The upper level includes a spacious primary suite with a private deck and ensuite bath with soaking tub, along with two additional bedrooms, a full hall bath, and convenient upper-level laundry. The fully finished lower level is perfect for hosting guests offering a large recreation room, additional bedroom, full bath, second laundry, and direct walk-out access to the backyard. The main level features multiple living spaces, a flexible front sitting room, and a beautifully appointed chef’s kitchen complete with a Wolf range, flattop cooking surface, wine fridge, peninsula seating, and generous dining space. Step outside to enjoy the fully fenced backyard featuring a large deck, lower patio, and multiple outdoor seating areas ideal for relaxing or entertaining. Additional highlights include large sized shed, driveway parking for up to 3 vehicles, and ample street parking. Don't miss this opportunity to own a spacious, thoughtfully designed home in a sought-after Annapolis location. Qualified military and civilian buyers may be eligible to assume the seller’s existing low-interest VA loan, offering significant financing advantages.

102 Brewer Ave, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: KW Metro Center.

$834,750

ONLINE REAL ESTATE AUCTION!! Online Bidding Opens - Monday, September 1, 2025. Online Bidding Closes - Wednesday, September 3, 2025 at 11:00 AM. List price is opening bid only. 199 Prince George Street is situated in the Downtown Annapolis Historic District, one block east of State Circle, and one block northwest of the City Dock. The home is within a short walk of Maryland State government offices, the State House, legislative houses, the US Naval Academy, restaurants, hotels, shops, historic sites and Annapolis Harbor. Prince George Street is a picturesque one-way street, lined with detached homes and townhomes often exceeding 100 years of age.

3 Beds ⋅ 3 Baths

ONLINE REAL ESTATE AUCTION!! Online Bidding Opens - Monday, September 1, 2025. Online Bidding Closes - Wednesday, September 3, 2025 at 11:00 AM. List price is opening bid only. 199 Prince George Street is situated in the Downtown Annapolis Historic District, one block east of State Circle, and one block northwest of the City Dock. The home is within a short walk of Maryland State government offices, the State House, legislative houses, the US Naval Academy, restaurants, hotels, shops, historic sites and Annapolis Harbor. Prince George Street is a picturesque one-way street, lined with detached homes and townhomes often exceeding 100 years of age.

199 Prince George St, Annapolis

Listing courtesy of A.J. Billig & Company. Contact:

Selling Office: Unrepresented Buyer Office.

$725,000

Welcome home! This private Annapolis retreat blends comfort and elegance, with dramatic high ceilings and main level living that feels both relaxed for everyday life and sophisticated for entertaining. Inside, discover an open floorplan with fresh paint, stunning vaulted wood ceilings, gleaming hardwood floors, and wide windows flooding the home with abundant natural light. The spacious and bright living room features a large picture window and recessed lighting, and is anchored by a striking double-sided stone gas fireplace flanked by built-in cabinets. Pass through the classic archway into the gorgeously updated kitchen (2021) featuring sleek marble countertops, new tile flooring, modern recessed lighting, and stainless steel appliances, including a high-end dual-fuel GE Café range with double oven (2021). With a central island breakfast bar and additional bank of cabinet storage, this spacious layout keeps the chef connected to the living and dining areas. Continue through the lovely glass pocket doors into the open dining and family room and be impressed by the custom vaulted wood ceiling, large windows and welcoming finishes. Down the hall, the rare main-level primary bedroom boasts a rich cathedral wood ceiling, newer plush carpeting, a cozy wood-burning fireplace that can easily convert to gas, and a unique two-level walk-in closet. Enjoy a beautifully appointed custom en suite bathroom with a luxurious oversized shower and a handsome vanity with a new countertop, sink, and faucet (2025). The second bedroom includes new soft carpeted flooring, ample closet space, and access to the second tastefully updated bathroom in the hallway. Downstairs, the lower level offers a versatile recreation room with brand new carpeting (2025) and a generously-sized storage room with built-in shelving. Two additional bedrooms and a third full bathroom with a step-in shower provide further flexibility for a private guest space, home office, or gym. Outside, enjoy an expansive wraparound and recently repainted wooden deck with built-in grill, and relax by the firepit in the privacy of nearly half an acre of fenced yard, surrounded by mature trees for a tranquil, scenic view. On the front of the home, the refinished driveway (2024) offers plenty of room for your boat or trailer. Recent major home updates include a newer roof (2022), geothermal energy-efficient HVAC (2019), upgraded Anderson doors and windows, whole-house water filtration with UV filters and a point-of-use reverse osmosis filtering sytsem, a 50-amp hookup for a potential hot tub, a gas line roughed for a future whole-house generator, replaced BAT septic system. Conveniently located just minutes to Giant, Annapolis Mall, Downtown Historic Annapolis, and Quiet Waters Park. Easy access to Route 50 and nearby commuter routes puts Annapolis, Baltimore, and the region within easy reach. Schedule a private showing to see everything this special home has to offer!

Welcome home! This private Annapolis retreat blends comfort and elegance, with dramatic high ceilings and main level living that feels both relaxed for everyday life and sophisticated for entertaining. Inside, discover an open floorplan with fresh paint, stunning vaulted wood ceilings, gleaming hardwood floors, and wide windows flooding the home with abundant natural light. The spacious and bright living room features a large picture window and recessed lighting, and is anchored by a striking double-sided stone gas fireplace flanked by built-in cabinets. Pass through the classic archway into the gorgeously updated kitchen (2021) featuring sleek marble countertops, new tile flooring, modern recessed lighting, and stainless steel appliances, including a high-end dual-fuel GE Café range with double oven (2021). With a central island breakfast bar and additional bank of cabinet storage, this spacious layout keeps the chef connected to the living and dining areas. Continue through the lovely glass pocket doors into the open dining and family room and be impressed by the custom vaulted wood ceiling, large windows and welcoming finishes. Down the hall, the rare main-level primary bedroom boasts a rich cathedral wood ceiling, newer plush carpeting, a cozy wood-burning fireplace that can easily convert to gas, and a unique two-level walk-in closet. Enjoy a beautifully appointed custom en suite bathroom with a luxurious oversized shower and a handsome vanity with a new countertop, sink, and faucet (2025). The second bedroom includes new soft carpeted flooring, ample closet space, and access to the second tastefully updated bathroom in the hallway. Downstairs, the lower level offers a versatile recreation room with brand new carpeting (2025) and a generously-sized storage room with built-in shelving. Two additional bedrooms and a third full bathroom with a step-in shower provide further flexibility for a private guest space, home office, or gym. Outside, enjoy an expansive wraparound and recently repainted wooden deck with built-in grill, and relax by the firepit in the privacy of nearly half an acre of fenced yard, surrounded by mature trees for a tranquil, scenic view. On the front of the home, the refinished driveway (2024) offers plenty of room for your boat or trailer. Recent major home updates include a newer roof (2022), geothermal energy-efficient HVAC (2019), upgraded Anderson doors and windows, whole-house water filtration with UV filters and a point-of-use reverse osmosis filtering sytsem, a 50-amp hookup for a potential hot tub, a gas line roughed for a future whole-house generator, replaced BAT septic system. Conveniently located just minutes to Giant, Annapolis Mall, Downtown Historic Annapolis, and Quiet Waters Park. Easy access to Route 50 and nearby commuter routes puts Annapolis, Baltimore, and the region within easy reach. Schedule a private showing to see everything this special home has to offer!

1114 Bay Ridge Rd, Annapolis

Listing courtesy of KW Metro Center. Contact:

Selling Office: Corcoran McEnearney.

$715,000

Welcome to this beautifully restored and thoughtfully updated 1942 gem. Step inside to find gleaming hardwood floors, sunlit living spaces, and original archtectural details blended seamlessly w contemporary updates. Outdoors, enjoy a peaceful side and rear garden, ideal for morning coffee or quiet evenings under the stars. Just a short walk is a scenic footbridge over Spa Creek to Truxton Park's pool, tennis courts and nature trails. Whether you're drawn by the charm of a historic home, the proximity to the water, or the vibrant culture of nearby downtown Annapolis, this property is the perfect place to call home

Welcome to this beautifully restored and thoughtfully updated 1942 gem. Step inside to find gleaming hardwood floors, sunlit living spaces, and original archtectural details blended seamlessly w contemporary updates. Outdoors, enjoy a peaceful side and rear garden, ideal for morning coffee or quiet evenings under the stars. Just a short walk is a scenic footbridge over Spa Creek to Truxton Park's pool, tennis courts and nature trails. Whether you're drawn by the charm of a historic home, the proximity to the water, or the vibrant culture of nearby downtown Annapolis, this property is the perfect place to call home

7 Silopanna Rd, Annapolis

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

Selling Office: Cummings & Co. Realtors.

$704,000

Gorgeous 4-Bedroom Home with High Ceilings & Flexible Living Spaces. Beautifully maintained and freshly painted, this 4-bedroom, 3.5-bath home offers generous living across three finished levels. The main floor features hardwood floors, a bright family room with fireplace, and an open-concept kitchen with a center island and 42" cabinets—ideal for both everyday living and entertaining. Upstairs, enjoy hardwood floors throughout and vaulted ceilings in the spacious primary suite. The custom-finished lower level includes new carpet, a private office or guest room, a third full bath, and a second family room with walk-out access. Step outside to a no-maintenance deck and a fully fenced rear yard that backs to trees—offering peace, privacy, and the perfect setting for outdoor enjoyment. All just a short walk to local marinas, shops, and minutes from downtown Annapolis.

4 Beds ⋅ 4 Baths

Gorgeous 4-Bedroom Home with High Ceilings & Flexible Living Spaces. Beautifully maintained and freshly painted, this 4-bedroom, 3.5-bath home offers generous living across three finished levels. The main floor features hardwood floors, a bright family room with fireplace, and an open-concept kitchen with a center island and 42" cabinets—ideal for both everyday living and entertaining. Upstairs, enjoy hardwood floors throughout and vaulted ceilings in the spacious primary suite. The custom-finished lower level includes new carpet, a private office or guest room, a third full bath, and a second family room with walk-out access. Step outside to a no-maintenance deck and a fully fenced rear yard that backs to trees—offering peace, privacy, and the perfect setting for outdoor enjoyment. All just a short walk to local marinas, shops, and minutes from downtown Annapolis.

916 King James Landing Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: RE/MAX Realty Group.

$557,000

This inviting 3-bedroom, 2 full bath rancher will feel like home the moment you step inside. Hardwood floors throughout the main level. Exposed wood beams and a wood-burning fireplace in the living room add a rustic, cozy charm. The spacious primary suite offers a comfortable retreat, while plantation shutters add timeless classic character throughout. The sunny kitchen with tile countertops opens to a dining area that flows onto a secluded deck, ideal for morning coffee or relaxed dinners surrounded by nature. Downstairs, the finished lower level provides a flexible multipurpose room, full bath, and laundry room, creating space to spread out and unwind or perfect for a third bedroom. A quaint detached one-car garage houses a workshop ideal for hobbies and weekend projects. Added bonus - New Roof! New Siding! New Windows! New Gutter System! Come see for yourself!

This inviting 3-bedroom, 2 full bath rancher will feel like home the moment you step inside. Hardwood floors throughout the main level. Exposed wood beams and a wood-burning fireplace in the living room add a rustic, cozy charm. The spacious primary suite offers a comfortable retreat, while plantation shutters add timeless classic character throughout. The sunny kitchen with tile countertops opens to a dining area that flows onto a secluded deck, ideal for morning coffee or relaxed dinners surrounded by nature. Downstairs, the finished lower level provides a flexible multipurpose room, full bath, and laundry room, creating space to spread out and unwind or perfect for a third bedroom. A quaint detached one-car garage houses a workshop ideal for hobbies and weekend projects. Added bonus - New Roof! New Siding! New Windows! New Gutter System! Come see for yourself!

1930 Severn Grove Rd, Annapolis

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

Selling Office: Next Step Realty, LLC..

$550,000

Unbeatable USNA Proximity! Perfectly Located to enjoy all of what downtown Annapolis has to offer! This delightful one-level condo at 31 College Ave places you in the premier location, literally neighbors with the Naval Academy and St. John’s. Enjoy a functional, open floor plan with a decorative fireplace, gas cooking, and a luxurious custom bath in the primary suite. Includes basement storage unit and common storage space. With Maryland Avenue’s dining and the City Dock just blocks away, this is the perfect home base for Navy fans and downtown enthusiasts alike. Enjoy the spirit of the Yard and the beauty of the City Dock every single day.

1 Beds ⋅ 1 Baths

Unbeatable USNA Proximity! Perfectly Located to enjoy all of what downtown Annapolis has to offer! This delightful one-level condo at 31 College Ave places you in the premier location, literally neighbors with the Naval Academy and St. John’s. Enjoy a functional, open floor plan with a decorative fireplace, gas cooking, and a luxurious custom bath in the primary suite. Includes basement storage unit and common storage space. With Maryland Avenue’s dining and the City Dock just blocks away, this is the perfect home base for Navy fans and downtown enthusiasts alike. Enjoy the spirit of the Yard and the beauty of the City Dock every single day.

31 College Ave, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$505,000

Great opportunity for investor or buyer looking to live in one unit and rent the other. This is a good condition legal two unit in Annapolis. Main level unit A has one bedroom, living room, kitchen, full bath, full size washer/dryer. Upper level unit B has separate entrance (side of house) two bedrooms, 1 bath, eat in kitchen, living area, loft room that is finished and is bedroom #2, full size washer/dryer in this unit as well. 1680 finished square feet (924 main level; 756 upstairs unit). Gas heat and cooking; central air conditioning. ZONED PM (Professional mixed use)...refer to city code to see what uses are allowed besides residential. Off street parking for 3 cars. Nice surprise is the 207' deep lot features a private yard. detached shed in rear offers extra storage. furnishings negotiable

Great opportunity for investor or buyer looking to live in one unit and rent the other. This is a good condition legal two unit in Annapolis. Main level unit A has one bedroom, living room, kitchen, full bath, full size washer/dryer. Upper level unit B has separate entrance (side of house) two bedrooms, 1 bath, eat in kitchen, living area, loft room that is finished and is bedroom #2, full size washer/dryer in this unit as well. 1680 finished square feet (924 main level; 756 upstairs unit). Gas heat and cooking; central air conditioning. ZONED PM (Professional mixed use)...refer to city code to see what uses are allowed besides residential. Off street parking for 3 cars. Nice surprise is the 207' deep lot features a private yard. detached shed in rear offers extra storage. furnishings negotiable

1201 West St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

LOCATION, LOCATION, LOCATION! This rare opportunity in the Annapolis Historic District is ready for the right buyer to bring it back to life. Tucked away on a charming brick path, this two-story converted carriage house offers historic character and endless potential. Featuring 1 bedroom, 2 baths, and a welcoming Dutch front door, this home is full of distinctive details. The first-floor living room boasts a cozy fireplace, while the bedroom upstairs includes its own fireplace and opens through double doors to a screened-in patio, creating a quiet retreat in the heart of the city. The garden and patio space are waiting for a creative eye to transform them into something truly special. Just blocks from the Naval Academy and City Dock, this property needs significant work but is an excellent opportunity for an investor or visionary buyer looking to make their mark in one of Annapolis’ most sought-after locations. Buyer to pay a short sale negotiation fee of $6,000.00 or 2% of the purchase price, whichever is greater, upon closing. Motivated seller – bring your offer!

$500,000

1 Beds ⋅ 2 Baths

LOCATION, LOCATION, LOCATION! This rare opportunity in the Annapolis Historic District is ready for the right buyer to bring it back to life. Tucked away on a charming brick path, this two-story converted carriage house offers historic character and endless potential. Featuring 1 bedroom, 2 baths, and a welcoming Dutch front door, this home is full of distinctive details. The first-floor living room boasts a cozy fireplace, while the bedroom upstairs includes its own fireplace and opens through double doors to a screened-in patio, creating a quiet retreat in the heart of the city. The garden and patio space are waiting for a creative eye to transform them into something truly special. Just blocks from the Naval Academy and City Dock, this property needs significant work but is an excellent opportunity for an investor or visionary buyer looking to make their mark in one of Annapolis’ most sought-after locations. Buyer to pay a short sale negotiation fee of $6,000.00 or 2% of the purchase price, whichever is greater, upon closing. Motivated seller – bring your offer!

212 King George St, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$495,000

Located on a picturesque tree-lined street in highly desirable Annapolis, MD, this property offers great potential for the experienced investor, contractor or developer. Potential uses include: 1) renovate the current structure - all brick rancher +/- 2,000 sqft included in the sale - HOME NEEDS TOTAL RENOVATION and will not pass conventional financing appraisal/condition requirements 2) demo the current structure and build a new home. Buyer to complete their own due diligence and confirm all potential uses. Property sold strictly AS-IS. Extensive engineering has been completed by current owner to build one large estate home on 341-343 Dubois Rd (2 parcels). Adjoining parcel 343 Dubois Rd can be purchased in combination or separately for $350,000. Potential to-be-built home listed under MDAA2129980. Call listing agent with questions.

341 Dubois Rd, Annapolis

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

Located on a picturesque tree-lined street in highly desirable Annapolis, MD, this property offers great potential for the experienced investor, contractor or developer. Potential uses include: 1) renovate the current structure - all brick rancher +/- 2,000 sqft included in the sale - HOME NEEDS TOTAL RENOVATION and will not pass conventional financing appraisal/condition requirements 2) demo the current structure and build a new home. Buyer to complete their own due diligence and confirm all potential uses. Property sold strictly AS-IS. Extensive engineering has been completed by current owner to build one large estate home on both parcels. Potential to-be-built home listed under MDAA2129980. Call listing agent with questions.

$495,000

3 Beds ⋅ 3 Baths

Located on a picturesque tree-lined street in highly desirable Annapolis, MD, this property offers great potential for the experienced investor, contractor or developer. Potential uses include: 1) renovate the current structure - all brick rancher +/- 2,000 sqft included in the sale - HOME NEEDS TOTAL RENOVATION and will not pass conventional financing appraisal/condition requirements 2) demo the current structure and build a new home. Buyer to complete their own due diligence and confirm all potential uses. Property sold strictly AS-IS. Extensive engineering has been completed by current owner to build one large estate home on both parcels. Potential to-be-built home listed under MDAA2129980. Call listing agent with questions.

341 Dubois Rd, Annapolis

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

Welcome to this Wonderful home very close to Annapolis & the properties to be in a private area but close proximity to be in the City of Annapolis! Located in close proximity to restaurants , shopping, and entertainmemt . You will enjoy summer evenings dining - out in the over large deck out back! The Home offers an open floor plan that leads you to entertaining with a spacious living room, Dining Room & Remodeled Kitchen with Granite counter tops and New stainless steel Appliances. The dining & Living room boasts beautiful refinished hardwood flooring and Open to a Kitchen . The primary bedroom offers private Full remodeled bath with access to shower In addition to 2 others great size bedrooms and a Full renovated bathroom! Relax in the finished basement that offers large rec room, Additional bedroom/office/playroom and full renovated 3rd bath! You will love this home! Ready for your buyer to move-in!!

$495,000

Welcome to this Wonderful home very close to Annapolis & the properties to be in a private area but close proximity to be in the City of Annapolis! Located in close proximity to restaurants , shopping, and entertainmemt . You will enjoy summer evenings dining - out in the over large deck out back! The Home offers an open floor plan that leads you to entertaining with a spacious living room, Dining Room & Remodeled Kitchen with Granite counter tops and New stainless steel Appliances. The dining & Living room boasts beautiful refinished hardwood flooring and Open to a Kitchen . The primary bedroom offers private Full remodeled bath with access to shower In addition to 2 others great size bedrooms and a Full renovated bathroom! Relax in the finished basement that offers large rec room, Additional bedroom/office/playroom and full renovated 3rd bath! You will love this home! Ready for your buyer to move-in!!

1971 Dominoe Rd, Annapolis

Listing courtesy of RE/MAX Realty Group. Contact:

Selling Office: Fairfax Realty Select.

$405,000

“The House and a Half” is a truly distinctive and beloved downtown Annapolis residence, admired by passersby and perfectly positioned in the heart of the historic district. A sun-filled foyer with a charming wood-burning fireplace sets a warm, welcoming tone and flows seamlessly into the living and dining rooms. The kitchen continues the home’s timeless appeal, featuring gray cabinetry, stainless steel appliances, and direct access to a private courtyard—ideal for entertaining or peaceful outdoor moments. Rounding out the main level is the tastefully updated powder room with porcelain tile floors, perfect for guests. The second level offers a generously sized primary bedroom and a beautifully renovated full bath with a walk-in shower. A second bedroom and a convenient laundry area complete this floor. The third level provides a versatile third bedroom, perfect for a home office, guest space, or additional storage. Just steps from the shops, dining, and entertainment of West Street, this exceptional location delivers the best of downtown Annapolis living—where historic charm meets everyday convenience. Don't miss it!

“The House and a Half” is a truly distinctive and beloved downtown Annapolis residence, admired by passersby and perfectly positioned in the heart of the historic district. A sun-filled foyer with a charming wood-burning fireplace sets a warm, welcoming tone and flows seamlessly into the living and dining rooms. The kitchen continues the home’s timeless appeal, featuring gray cabinetry, stainless steel appliances, and direct access to a private courtyard—ideal for entertaining or peaceful outdoor moments. Rounding out the main level is the tastefully updated powder room with porcelain tile floors, perfect for guests. The second level offers a generously sized primary bedroom and a beautifully renovated full bath with a walk-in shower. A second bedroom and a convenient laundry area complete this floor. The third level provides a versatile third bedroom, perfect for a home office, guest space, or additional storage. Just steps from the shops, dining, and entertainment of West Street, this exceptional location delivers the best of downtown Annapolis living—where historic charm meets everyday convenience. Don't miss it!

185 Clay St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

Amazing opportunity to renovate a home close to downtown Annapolis! This 3 bedroom, 1.5 bath home is a great opportunity for a handy buyer or investor looking to renovate and/or expand the space. Currently, there are three bedrooms and 1.5 bathrooms on the upstairs level. A spacious kitchen, living and dining room lend themselves to an open floor plan. Three bedrooms, one full bath and one half bath on upper level. Lower level has finished rec room space, and unfinished space for an additional bedroom and rough in for bath. Minutes to downtown Annapolis, Route 50, shopping and more! Property sold As-Is.

$379,000

Amazing opportunity to renovate a home close to downtown Annapolis! This 3 bedroom, 1.5 bath home is a great opportunity for a handy buyer or investor looking to renovate and/or expand the space. Currently, there are three bedrooms and 1.5 bathrooms on the upstairs level. A spacious kitchen, living and dining room lend themselves to an open floor plan. Three bedrooms, one full bath and one half bath on upper level. Lower level has finished rec room space, and unfinished space for an additional bedroom and rough in for bath. Minutes to downtown Annapolis, Route 50, shopping and more! Property sold As-Is.

1013 Hanson St, Annapolis

Listing courtesy of Compass. Contact:

Selling Office: Pearson Smith Realty, LLC.

$374,900

***$5000 seller concession with full price offer by 9/28/25*** Charming Townhome Near Downtown Annapolis & the U.S. Naval Academy Welcome to 1007 Madison Ct, a well-maintained 3-bedroom, 2-bathroom townhome ideally situated just minutes from historic downtown Annapolis and the U.S. Naval Academy. This versatile layout offers comfortable living across three levels. Upstairs, you’ll find two spacious bedrooms with plush carpeting and a full bathroom, providing a quiet retreat. The finished basement adds flexibility with a third bedroom, a second full bath, and additional living or guest space and laundry. Enjoy the convenience of being close to vibrant shops, waterfront dining, and cultural landmarks, all while tucked into a quiet, established community. Whether you're looking for a full-time residence or an investment property, this home offers location, comfort, and potential. Don’t miss this opportunity to own a home in one of Annapolis’s most desirable areas! Seller's current home warranty will transfer.

***$5000 seller concession with full price offer by 9/28/25*** Charming Townhome Near Downtown Annapolis & the U.S. Naval Academy Welcome to 1007 Madison Ct, a well-maintained 3-bedroom, 2-bathroom townhome ideally situated just minutes from historic downtown Annapolis and the U.S. Naval Academy. This versatile layout offers comfortable living across three levels. Upstairs, you’ll find two spacious bedrooms with plush carpeting and a full bathroom, providing a quiet retreat. The finished basement adds flexibility with a third bedroom, a second full bath, and additional living or guest space and laundry. Enjoy the convenience of being close to vibrant shops, waterfront dining, and cultural landmarks, all while tucked into a quiet, established community. Whether you're looking for a full-time residence or an investment property, this home offers location, comfort, and potential. Don’t miss this opportunity to own a home in one of Annapolis’s most desirable areas! Seller's current home warranty will transfer.

1007 Madison Ct, Annapolis

Listing courtesy of Redfin Corp. Contact:

Selling Office: EXP Realty, LLC.

$349,900

Step into this beautifully renovated Annapolis charmer — completely updated from the ground up in 2018! Every detail has been thoughtfully designed for comfort and style, from the **custom kitchen with quartz countertops and stainless steel appliances** to the **gleaming hardwood floors** and **spa-inspired bath**. The home features **newer roof and windows**, efficient systems, and modern finishes throughout, offering a true move-in-ready experience. Outside, enjoy a **large fenced yard**, **above-ground pool**, and **screened-in rear porch** — perfect for entertaining or relaxing all year long. Located within walking distance to **shopping, restaurants, and downtown Annapolis**, this home delivers unbeatable convenience and charm. Why rent when you can own this thoughtfully renovated gem for less?

2 Beds ⋅ 1 Baths

Step into this beautifully renovated Annapolis charmer — completely updated from the ground up in 2018! Every detail has been thoughtfully designed for comfort and style, from the **custom kitchen with quartz countertops and stainless steel appliances** to the **gleaming hardwood floors** and **spa-inspired bath**. The home features **newer roof and windows**, efficient systems, and modern finishes throughout, offering a true move-in-ready experience. Outside, enjoy a **large fenced yard**, **above-ground pool**, and **screened-in rear porch** — perfect for entertaining or relaxing all year long. Located within walking distance to **shopping, restaurants, and downtown Annapolis**, this home delivers unbeatable convenience and charm. Why rent when you can own this thoughtfully renovated gem for less?

27 Dorsey Ave, Annapolis

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

Selling Office: Compass.

$332,500

Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring throughout, presenting a promising canvas for renovation. Strategically located, this property is in close proximity to essential amenities and community .Public transportation is conveniently accessible with the Riva Road & Forest Drive bus station less than 700 meters away, enhancing the location. Additional features include a rear deck perfect for relaxation or casual gatherings, a useful rear shed for extra storage, and a generous off-street parking area that can accommodate up to 12 vehicles. Despite being sold as-is, with no repairs from the seller, the property's inherent potential and dual-use capability as both a residential and commercial space make it a lucrative deal. Capitalize on the chance to customize this space into a thriving business venture or a mixed-use development that promises both rental income and renovation possibilities. Dive into this project and shape it into your vision of success! Property is being sold AS-IS, Seller will make no repairs. All offers must have $1000 deposit and proof of deposit. Buyer responsible for all due diligence on condition of home. So much potential! Make this your today!!

2 Beds ⋅ 2 Baths

Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring throughout, presenting a promising canvas for renovation. Strategically located, this property is in close proximity to essential amenities and community .Public transportation is conveniently accessible with the Riva Road & Forest Drive bus station less than 700 meters away, enhancing the location. Additional features include a rear deck perfect for relaxation or casual gatherings, a useful rear shed for extra storage, and a generous off-street parking area that can accommodate up to 12 vehicles. Despite being sold as-is, with no repairs from the seller, the property's inherent potential and dual-use capability as both a residential and commercial space make it a lucrative deal. Capitalize on the chance to customize this space into a thriving business venture or a mixed-use development that promises both rental income and renovation possibilities. Dive into this project and shape it into your vision of success! Property is being sold AS-IS, Seller will make no repairs. All offers must have $1000 deposit and proof of deposit. Buyer responsible for all due diligence on condition of home. So much potential! Make this your today!!

40 Oak Ct, Annapolis

Listing courtesy of ExecuHome Realty. Contact:

Selling Office: Douglas Realty LLC.

$315,000

This charming 5 bedroom, 2 bath Cape Cod is located in a community with quick and easy access to Spa Road as well as West Street. There is a welcoming and covered front porch and a large back yard with a back deck. While the home will require work, it has loads of potential to be a lovely gem on Smithville.

5 Beds ⋅ 2 Baths

This charming 5 bedroom, 2 bath Cape Cod is located in a community with quick and easy access to Spa Road as well as West Street. There is a welcoming and covered front porch and a large back yard with a back deck. While the home will require work, it has loads of potential to be a lovely gem on Smithville.

1029 Smithville St, Annapolis

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

Selling Office: RE/MAX Leading Edge.

$285,000

You won't find another home like this for this price in Annapolis! There is a nice water view of College Creek! Recorded plat and deed indicate the lot goes to the shores of College Creek. Walk to downtown historic district, only 3 1/2 blocks to Calvert Street! Fully fenced back yard is much larger than other townhomes and is perfect for the gardener. The home was fully renovated in 2002: Open first floor plan, 200 amp electric, plumbing replaced, kitchen, baths, laundry on 2nd floor (bedroom level). Renovation provided excellent closet space, nice sized kitchen, living room. A bonus is the walk-up floored attic that can be finished or used for storage. Seller says roof replaced in October 2021. Access to Rideout St in back beyond rear fence gate (see subdivision drawing).

2 Beds ⋅ 2 Baths

You won't find another home like this for this price in Annapolis! There is a nice water view of College Creek! Recorded plat and deed indicate the lot goes to the shores of College Creek. Walk to downtown historic district, only 3 1/2 blocks to Calvert Street! Fully fenced back yard is much larger than other townhomes and is perfect for the gardener. The home was fully renovated in 2002: Open first floor plan, 200 amp electric, plumbing replaced, kitchen, baths, laundry on 2nd floor (bedroom level). Renovation provided excellent closet space, nice sized kitchen, living room. A bonus is the walk-up floored attic that can be finished or used for storage. Seller says roof replaced in October 2021. Access to Rideout St in back beyond rear fence gate (see subdivision drawing).

192 Clay St, Annapolis

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

Selling Office: Long & Foster Real Estate, Inc..

$275,000

NEW PRICE! Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife. Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly $40,000 in earnings in 2024 and over $22,000 already booked through August 2025. Inside, the main level features a spacious family room, dining area, and kitchen that opens to a deck and fenced backyard, perfect for entertaining. Upstairs, you’ll find two bedrooms, a full bath, and a bonus loft area for an office or guest space. Don’t miss your chance to own an Annapolis gem with walkable lifestyle perks and a track record of short-term rental success.

2 Beds ⋅ 1 Baths

NEW PRICE! Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife. Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly $40,000 in earnings in 2024 and over $22,000 already booked through August 2025. Inside, the main level features a spacious family room, dining area, and kitchen that opens to a deck and fenced backyard, perfect for entertaining. Upstairs, you’ll find two bedrooms, a full bath, and a bonus loft area for an office or guest space. Don’t miss your chance to own an Annapolis gem with walkable lifestyle perks and a track record of short-term rental success.

26 Pleasant St, Annapolis

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

Selling Office: Samson Properties.

$235,000

NEW PRICE !!! Welcome to Annapolis! This beautifully updated 3-bedroom, 1 full and 1 half-bath townhome offers a fantastic opportunity to own in one of Maryland’s most historic and charming locations. Fully renovated from top to bottom, this home features updated bathrooms, a renovated kitchen with brand-new stainless steel appliances, new LVP flooring on both levels, a new washer and dryer, a new hot water heater, new baseboard heaters, and a new window AC unit. The home has also been freshly painted throughout and includes updated plumbing. The HOA is only $26 per month. Ideally located in the heart of Annapolis, just minutes from the Capitol building, the Naval Academy, waterfront, shopping, and restaurants. Move-in ready, a must see!