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Unique Waterfront Lot Opportunity at Columbia Beach – Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to own a buildable waterfront lot in the serene, gated community of Columbia Beach, offering breathtaking views of the Chesapeake Bay. This exclusive neighborhood is just 30 minutes from the I-495 Beltway and Annapolis, and only 45 minutes to Washington, D.C., and the Woodrow Wilson Bridge in Virginia. Community Highlights: Gated access for privacy and peace of mind. Stunning bayfront scenery. Boat ramp, short pier, and long pier for water access. Family-friendly playgrounds. Sports facilities including tennis, basketball, and pickleball. Pet-friendly with a commitment to preserving the peaceful environment. Columbia Beach is served by Public Sewer and is known for its quiet streets, low traffic, and tight-knit community, making it an ideal setting for a primary residence or vacation getaway. AirBNB is allowed. Lot Details: Approx 60'x100' Buildable waterfront lot with completed boundary survey (available via listing documents). 20year loan available with 25% down, local and competitive lender. Listed separately as a "House-to-Be-Built" option with flexible design options. Ideal for a custom home measuring up to 46' wide x 32' deep each level. Potential for 2 finished levels plus attic, and designed for: 5BED/4BH. Main level bedroom with full bath – wheelchair accessible. 2-car garage. Deck and/or balcony for stunning water views. "Qualified buyers can finance the entire project — including lot and building — with as little as 5% down, thanks to Construction-to-Permanent loans that may allow for 10%, 15%, or even 20% equity from the start." An experienced builder is ready to work with you to create a custom dream home, offering competitive pricing and may even absorb a portion of the lot cost. For additional Info on Columbia Beach: Visit the Columbia Beach page to learn more about the community. Lot owner reserves the right to accept or reject any offer.

5235 Al Jones Dr, Shady Side

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

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

$349,500

This charming 3-bedroom, 2-full-bath cottage offers the perfect blend of comfort, convenience, and coastal living. Nestled in a sought-after water privileged community, you will enjoy easy access to the bay, making it ideal for boating, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, the home features a bright and inviting layout with comfortable living spaces and well-appointed bedrooms. Step outside to a fully fenced backyard-perfect for pets and entertaining. Whether you're looking for a year-round residence or a peaceful getaway, this cottage offers the best of Chesapeake Bay living in a friendly community with water access and a relaxed coastal atmosphere. Don't miss the opportunity to make this charming bay cottage your own.

3 Beds ⋅ 2 Baths

This charming 3-bedroom, 2-full-bath cottage offers the perfect blend of comfort, convenience, and coastal living. Nestled in a sought-after water privileged community, you will enjoy easy access to the bay, making it ideal for boating, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, the home features a bright and inviting layout with comfortable living spaces and well-appointed bedrooms. Step outside to a fully fenced backyard-perfect for pets and entertaining. Whether you're looking for a year-round residence or a peaceful getaway, this cottage offers the best of Chesapeake Bay living in a friendly community with water access and a relaxed coastal atmosphere. Don't miss the opportunity to make this charming bay cottage your own.

1314 Pine St, Shady Side

Listing courtesy of Peninsula Properties, LLC.. Contact:

Selling Office: Peninsula Properties, LLC..

$347,000

Don’t miss this wonderful opportunity to own a well-maintained home at an affordable price! This inviting property features a spacious living/dining room combo with soaring cathedral ceilings that create an open, airy feel. The primary bedroom includes a full en-suite bath and sliding doors that lead to your private deck—perfect for enjoying the large, fully fenced backyard. The kitchen boasts newer appliances and another set of sliders opening to a secluded patio, ideal for outdoor dining or relaxation. Two additional bedrooms and a second full bath offer plenty of space for family or guests. A convenient utility room comes equipped with a newer washer and dryer. Large shed with electricity. Oversized paved driveway. Solar panels with average electric bills of just $33/month. Roof less than 5 years old. Carpet installed less than 1 year ago. HVAC system less than 3 years old. All windows and exterior doors replaced within the last 2 years. Located just a few blocks from the community beach, boat ramp, playground, and more, this home also qualifies for 100% USDA financing—a perfect fit for first-time buyers.

3 Beds ⋅ 2 Baths

Don’t miss this wonderful opportunity to own a well-maintained home at an affordable price! This inviting property features a spacious living/dining room combo with soaring cathedral ceilings that create an open, airy feel. The primary bedroom includes a full en-suite bath and sliding doors that lead to your private deck—perfect for enjoying the large, fully fenced backyard. The kitchen boasts newer appliances and another set of sliders opening to a secluded patio, ideal for outdoor dining or relaxation. Two additional bedrooms and a second full bath offer plenty of space for family or guests. A convenient utility room comes equipped with a newer washer and dryer. Large shed with electricity. Oversized paved driveway. Solar panels with average electric bills of just $33/month. Roof less than 5 years old. Carpet installed less than 1 year ago. HVAC system less than 3 years old. All windows and exterior doors replaced within the last 2 years. Located just a few blocks from the community beach, boat ramp, playground, and more, this home also qualifies for 100% USDA financing—a perfect fit for first-time buyers.

4913 Chestnut St, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

Selling Office: Redfin Corp.

$327,500

Peaceful Living by the Bay – Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal opportunity for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural beauty—with low maintenance. With a short walk less than 700 feet to bay front, you’ll love starting your mornings with coastal breezes and winding down with sunset walks to the community pier. Inside, enjoy a warm and inviting open layout, complete with a cozy wood stove and a splash of personality from the bright red front door. Major updates—roof, HVAC, water softener, and well pump—all installed in 2022—mean you can move in and relax from day one. The manageable yard has 2 sheds for extra storage. The oversized driveway allows space for guest parking during the summer months or boat storage year round. Plus, the neighboring nature reserve means no new development next door—ever. If you’re ready to downsize to comfort, convenience, and coastal charm, this is the home for you.

3 Beds ⋅ 1 Baths

Peaceful Living by the Bay – Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal opportunity for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural beauty—with low maintenance. With a short walk less than 700 feet to bay front, you’ll love starting your mornings with coastal breezes and winding down with sunset walks to the community pier. Inside, enjoy a warm and inviting open layout, complete with a cozy wood stove and a splash of personality from the bright red front door. Major updates—roof, HVAC, water softener, and well pump—all installed in 2022—mean you can move in and relax from day one. The manageable yard has 2 sheds for extra storage. The oversized driveway allows space for guest parking during the summer months or boat storage year round. Plus, the neighboring nature reserve means no new development next door—ever. If you’re ready to downsize to comfort, convenience, and coastal charm, this is the home for you.

4738 Washington Ave, Shady Side

Listing courtesy of Samson Properties. Contact:

Selling Office: Lazar Real Estate.

$325,000

Three living spaces, one property, half an acre near the water. This 2,807 sq. ft. home in Shady Side offers a rare setup: three separately accessible living areas under one roof, each with its own entrance. The main residence has two bedrooms, one full bath, a kitchen, and a family room opening to a rear deck. A private in-law suite (its own entrance, separate electric meter) is currently rented at $675/month with a long-term tenant in place. The upper level, accessible from both inside the home and its own exterior entrance, adds two more bedrooms, a living room, and a kitchenette, offering additional income potential or space for extended family. Set on a generous half-acre lot close to Shady Side Marina & Herrington Harbour Marina, this is a strong fit for investors, multi-generational buyers, or anyone looking to offset their mortgage with rental income from day one. The home does need updating and is being sold as-is. Conventional financing or cash buyers only.

4 Beds ⋅ 3 Baths

Three living spaces, one property, half an acre near the water. This 2,807 sq. ft. home in Shady Side offers a rare setup: three separately accessible living areas under one roof, each with its own entrance. The main residence has two bedrooms, one full bath, a kitchen, and a family room opening to a rear deck. A private in-law suite (its own entrance, separate electric meter) is currently rented at $675/month with a long-term tenant in place. The upper level, accessible from both inside the home and its own exterior entrance, adds two more bedrooms, a living room, and a kitchenette, offering additional income potential or space for extended family. Set on a generous half-acre lot close to Shady Side Marina & Herrington Harbour Marina, this is a strong fit for investors, multi-generational buyers, or anyone looking to offset their mortgage with rental income from day one. The home does need updating and is being sold as-is. Conventional financing or cash buyers only.

6201 Shady, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

Selling Office: Curtis Real Estate Company.

$325,000

Beautiful updated coastal cottage in the heart of Columbia Beach! *New roof 2023* This move-in ready 2-bedroom home features hardwood floors, a brand-new kitchen with stainless steel appliances, quartz countertops, and updated cabinets. Amazing loft area inside. Enjoy skylights and beautiful views. Beautifully landscaped level lot with a spacious back deck ideal for relaxing or entertaining. Enjoy exclusive community access to the Chesapeake Bay with a private boat ramp, pier, and beach. Close to Franklin Point State Park for even more outdoor fun. Fresh, bright, and full of charm this is coastal living at its best! Lot 28/29/30. All included for the sale.

2 Beds ⋅ 1 Baths

Beautiful updated coastal cottage in the heart of Columbia Beach! *New roof 2023* This move-in ready 2-bedroom home features hardwood floors, a brand-new kitchen with stainless steel appliances, quartz countertops, and updated cabinets. Amazing loft area inside. Enjoy skylights and beautiful views. Beautifully landscaped level lot with a spacious back deck ideal for relaxing or entertaining. Enjoy exclusive community access to the Chesapeake Bay with a private boat ramp, pier, and beach. Close to Franklin Point State Park for even more outdoor fun. Fresh, bright, and full of charm this is coastal living at its best! Lot 28/29/30. All included for the sale.

1731 Columbia Beach Rd, Shady Side

Listing courtesy of RE/MAX Excellence Realty. Contact:

Selling Office: Hyatt & Company Real Estate LLC.

$325,000

Charming Brick Home in Shady Side – Country Living with Coastal Perks Welcome to this peaceful brick retreat nestled in the heart of Shady Side. Set back on a beautifully flat and spacious 0.6-acre lot, this home offers privacy and tranquility surrounded by mature trees. The expansive backyard and side yard provide ample space for all your lifestyle needs—whether it’s boat storage, a travel trailer, or simply enjoying the outdoors. A circular driveway and covered carport make guest parking a breeze, while the freshly painted interior and exterior give the home a crisp, move-in-ready feel. Inside, you'll find three entry-level bedrooms and original hardwood floors throughout most rooms, adding warmth and character. Whether you're a first-time buyer or looking to downsize, this home is a perfect fit. Located just off Shady Side Road, you're minutes from Annapolis and enjoy easy access to all the charm and convenience the area has to offer. Best of all, the area offers many marinas and provides direct access to the Chesapeake Bay—ideal for kayaking, paddleboarding, boating, or simply soaking in the waterfront lifestyle. Bring all your water toys and start living your best Bay life!

3 Beds ⋅ 1 Baths

Charming Brick Home in Shady Side – Country Living with Coastal Perks Welcome to this peaceful brick retreat nestled in the heart of Shady Side. Set back on a beautifully flat and spacious 0.6-acre lot, this home offers privacy and tranquility surrounded by mature trees. The expansive backyard and side yard provide ample space for all your lifestyle needs—whether it’s boat storage, a travel trailer, or simply enjoying the outdoors. A circular driveway and covered carport make guest parking a breeze, while the freshly painted interior and exterior give the home a crisp, move-in-ready feel. Inside, you'll find three entry-level bedrooms and original hardwood floors throughout most rooms, adding warmth and character. Whether you're a first-time buyer or looking to downsize, this home is a perfect fit. Located just off Shady Side Road, you're minutes from Annapolis and enjoy easy access to all the charm and convenience the area has to offer. Best of all, the area offers many marinas and provides direct access to the Chesapeake Bay—ideal for kayaking, paddleboarding, boating, or simply soaking in the waterfront lifestyle. Bring all your water toys and start living your best Bay life!

1460 Cedarhurst Rd, Shady Side

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: The Southside Group Real Estate.

$319,900

Welcome to 4950 W End Ave – a charming coastal bungalow just steps from the Chesapeake Bay! This beautifully renovated home perfectly blends modern updates with relaxed bay-side living. Set on a total of .242 acs (additional lot included total), this property offers serenity, space, and privacy. Step inside to an open and airy floor plan filled with natural light. Warm hardwood floors, a soft coastal palette, and stylish finishes create a space that feels both fresh and welcoming. The updated kitchen features sleek gray cabinetry, butcher block counters, a full pantry, and an easy flow into the dining and living areas – perfect for entertaining or everyday comfort. The main level bedroom and renovated bath offer convenience, while the upper-level suite provides a personal retreat with a private bath. A new mini-split system adds year-round comfort and energy efficiency. Outside, enjoy ample parking, a spacious yard, your own putting green, a large storage shed, newer deck, and your own personal boat slip – ready for your next day on the water! Whether hosting summer cookouts or relaxing after a day on the bay, you’ll love the laid-back seaside vibe this property delivers. Located in a water-privileged community offering a bayside pier, boat ramp, and entertaining areas, you’ll experience the best of Chesapeake living right at your doorstep. Ideal as a full-time residence, weekend getaway, or vacation investment.

2 Beds ⋅ 2 Baths

Welcome to 4950 W End Ave – a charming coastal bungalow just steps from the Chesapeake Bay! This beautifully renovated home perfectly blends modern updates with relaxed bay-side living. Set on a total of .242 acs (additional lot included total), this property offers serenity, space, and privacy. Step inside to an open and airy floor plan filled with natural light. Warm hardwood floors, a soft coastal palette, and stylish finishes create a space that feels both fresh and welcoming. The updated kitchen features sleek gray cabinetry, butcher block counters, a full pantry, and an easy flow into the dining and living areas – perfect for entertaining or everyday comfort. The main level bedroom and renovated bath offer convenience, while the upper-level suite provides a personal retreat with a private bath. A new mini-split system adds year-round comfort and energy efficiency. Outside, enjoy ample parking, a spacious yard, your own putting green, a large storage shed, newer deck, and your own personal boat slip – ready for your next day on the water! Whether hosting summer cookouts or relaxing after a day on the bay, you’ll love the laid-back seaside vibe this property delivers. Located in a water-privileged community offering a bayside pier, boat ramp, and entertaining areas, you’ll experience the best of Chesapeake living right at your doorstep. Ideal as a full-time residence, weekend getaway, or vacation investment.

4950 W End Ave, Shady Side

Listing courtesy of RE/MAX One. Contact:

Selling Office: Samson Properties.

$315,000

Adorable and inviting bayside bungalow in the highly sought-after Cedarhurst community along the Chesapeake Bay! This charming 2-bedroom, 1-bath home is move-in ready and full of character. Whether you're looking for a peaceful primary residence, weekend retreat, or investment opportunity, this property checks all the boxes. Step inside to a bright and welcoming front den, leading into a cozy living space highlighted by warm wood flooring throughout. The updated kitchen features modern cabinetry and countertops, offering both style and functionality. Out back, enjoy a private yard complete with a slate patio—perfect for relaxing evenings or entertaining outdoors. Located in a desirable waterfront community known for its charm and access to the bay, this home is a rare find. Contact the listing agent today for more information or to schedule your showing!

2 Beds ⋅ 1 Baths

Adorable and inviting bayside bungalow in the highly sought-after Cedarhurst community along the Chesapeake Bay! This charming 2-bedroom, 1-bath home is move-in ready and full of character. Whether you're looking for a peaceful primary residence, weekend retreat, or investment opportunity, this property checks all the boxes. Step inside to a bright and welcoming front den, leading into a cozy living space highlighted by warm wood flooring throughout. The updated kitchen features modern cabinetry and countertops, offering both style and functionality. Out back, enjoy a private yard complete with a slate patio—perfect for relaxing evenings or entertaining outdoors. Located in a desirable waterfront community known for its charm and access to the bay, this home is a rare find. Contact the listing agent today for more information or to schedule your showing!

1223 Pine Ave, Shady Side

Listing courtesy of Hutchins Properties. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$315,000

Charming 1BR, 1BA cottage in Avalon Shores—just a short stroll to the water! This cozy home was offers a perfect blend of comfort and convenience. Step inside to find a layout ideal for weekend getaways or year-round living. The Kitchen features stainless steel appliances and lots of counter space. The spacious fully fenced backyard is a standout, featuring two outbuildings—one perfect for a workshop, studio, or hobby space of your choice that is insulated. Enjoy the peaceful, laid-back lifestyle of this water-oriented community. Don’t miss this unique opportunity to own a little slice of the good life in southern Anne Arundel County!

1 Beds ⋅ 1 Baths

Charming 1BR, 1BA cottage in Avalon Shores—just a short stroll to the water! This cozy home was offers a perfect blend of comfort and convenience. Step inside to find a layout ideal for weekend getaways or year-round living. The Kitchen features stainless steel appliances and lots of counter space. The spacious fully fenced backyard is a standout, featuring two outbuildings—one perfect for a workshop, studio, or hobby space of your choice that is insulated. Enjoy the peaceful, laid-back lifestyle of this water-oriented community. Don’t miss this unique opportunity to own a little slice of the good life in southern Anne Arundel County!

4962 Elm St, Shady Side

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

Selling Office: CENTURY 21 New Millennium.

$314,400

Estate sale handled by an attorney. This well-loved home has been in the same family since 1953 and is now ready for its next chapter. Offering generous living space and abundant potential, this property is ideal for buyers looking to build sweat equity and restore its original charm. Situated on a large lot, the sale also includes an additional 25' x 100' parcel located to the right of the home. The primary heating system is oil-fired radiator heat, complemented by a ductless mini-split system on the main level. A versatile bonus room on the main floor may serve as a third bedroom or home office. Hardwood floors run throughout the home (currently under area carpet), and newer windows. The home is being sold as is, and most contents will convey with the sale.

2 Beds ⋅ 2 Baths

Estate sale handled by an attorney. This well-loved home has been in the same family since 1953 and is now ready for its next chapter. Offering generous living space and abundant potential, this property is ideal for buyers looking to build sweat equity and restore its original charm. Situated on a large lot, the sale also includes an additional 25' x 100' parcel located to the right of the home. The primary heating system is oil-fired radiator heat, complemented by a ductless mini-split system on the main level. A versatile bonus room on the main floor may serve as a third bedroom or home office. Hardwood floors run throughout the home (currently under area carpet), and newer windows. The home is being sold as is, and most contents will convey with the sale.

1241 Steamboat Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

Selling Office: RE/MAX Executive.

$309,000

Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to the water. Situated in Columbia Beach, feel like you're vacationing year round! Whether your taking a walk in the gated community, or entertaining in the spacious home, you'll enjoy living here! No HOA. Please read agent remarks.

3 Beds ⋅ 3 Baths

Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to the water. Situated in Columbia Beach, feel like you're vacationing year round! Whether your taking a walk in the gated community, or entertaining in the spacious home, you'll enjoy living here! No HOA. Please read agent remarks.

1512 Lincoln Rd, Shady Side

Listing courtesy of CENTURY 21 New Millennium. Contact:

Selling Office: Coldwell Banker Realty.

$292,000

A Charming Cedarhurst Cottage Near the Water - This charming 1944 cottage in Cedarhurst on the Bay offers easy coastal living and only a few houses from the Bay and the community amenities. Recent improvements within the last year include a new roof, new windows, a new hot water tank and a new water pressure tank. The kitchen has white cabinetry and there is a small laundry room with a washer and dryer combination machine. Both bedrooms are comfortable in size and the bathroom includes a walk in white shower stall with built in shelves for storage. The fenced backyard features a shed and a pleasant deck. Enjoy community amenities such as a pier and gazebo overlooking the Chesapeake, a small beach area, open green space and a marina with boat slips. A relaxed bayside setting makes this a great full time home or weekend getaway.

2 Beds ⋅ 1 Baths

A Charming Cedarhurst Cottage Near the Water - This charming 1944 cottage in Cedarhurst on the Bay offers easy coastal living and only a few houses from the Bay and the community amenities. Recent improvements within the last year include a new roof, new windows, a new hot water tank and a new water pressure tank. The kitchen has white cabinetry and there is a small laundry room with a washer and dryer combination machine. Both bedrooms are comfortable in size and the bathroom includes a walk in white shower stall with built in shelves for storage. The fenced backyard features a shed and a pleasant deck. Enjoy community amenities such as a pier and gazebo overlooking the Chesapeake, a small beach area, open green space and a marina with boat slips. A relaxed bayside setting makes this a great full time home or weekend getaway.

1213 Oak Ave, Shady Side

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

Selling Office: Gamble Realty, Inc.

$290,000

Don't miss this wonderful opportunity to own this porch front home seated in an expansive private lot approximately 3.38 acres. Home features hardwood floors that flows from the combined living and dining rooms to the nice sized kitchen with appliances and main level bedroom and bath. There is a full bath on each level and three more bedrooms on the upper level. The sunroom with wide windows and lots of natural light has a great view of the backyard and leads to the rear deck, which is a perfect spot for outdoor fun. The rear exterior includes a 3-car detached garage with large workshop and an unfinished upper level. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side attractions. NOTE - Buyers winning the Highest & Best must understand that they participated in a Highest & Best, Multiple Offers Situation and that any requests to the Seller for Special Concessions, Repairs or Switch in Financing could result in the Seller terminating and retaining Buyer's EMD.

4 Beds ⋅ 2 Baths

Don't miss this wonderful opportunity to own this porch front home seated in an expansive private lot approximately 3.38 acres. Home features hardwood floors that flows from the combined living and dining rooms to the nice sized kitchen with appliances and main level bedroom and bath. There is a full bath on each level and three more bedrooms on the upper level. The sunroom with wide windows and lots of natural light has a great view of the backyard and leads to the rear deck, which is a perfect spot for outdoor fun. The rear exterior includes a 3-car detached garage with large workshop and an unfinished upper level. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side attractions. NOTE - Buyers winning the Highest & Best must understand that they participated in a Highest & Best, Multiple Offers Situation and that any requests to the Seller for Special Concessions, Repairs or Switch in Financing could result in the Seller terminating and retaining Buyer's EMD.

6070 Shady, Shady Side

Listing courtesy of Century 21 Downtown. Contact:

Selling Office: Engel & Volkers Annapolis.

$285,000

Listed and sold simultaneously. Home needed tremendous amount of work.

2 Beds ⋅ 2 Baths

Listed and sold simultaneously. Home needed tremendous amount of work.

4908 Olive St, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

Selling Office: Unrepresented Buyer Office.

$276,000

Great opportunity to live by the water! Welcome to Columbia Beach!!! This gated community has wonderful amenities such as a fishing pier, boat ramp, tot lot, basketball court, common grounds and benches to relax and enjoy the beautiful water views. Take advantage of this great opportunity to live in a water privileged community. Home is being sold As-Is but is totally livable.

3 Beds ⋅ 2 Baths

Great opportunity to live by the water! Welcome to Columbia Beach!!! This gated community has wonderful amenities such as a fishing pier, boat ramp, tot lot, basketball court, common grounds and benches to relax and enjoy the beautiful water views. Take advantage of this great opportunity to live in a water privileged community. Home is being sold As-Is but is totally livable.

1503 Callaway Dr, Shady Side

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: RE/Max Experience.

$274,000

Listed & sold simultaneously. Home needed tremendous amount of work. Buyer was responsible for removing tremendous amount of trash both inside and out.

4 Beds ⋅ 2 Baths

Listed & sold simultaneously. Home needed tremendous amount of work. Buyer was responsible for removing tremendous amount of trash both inside and out.

4939 Bonniewood Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

Selling Office: Unrepresented.

$274,000

Welcome to 4717 Frederick Avenue — a charming and updated cottage just two blocks from the West River in the Idlewilde on the Bay community. This 2-bedroom, 1-bath ranch-style home offers comfortable one-level living with thoughtful improvements throughout. Step inside to a bright, open living area featuring neutral finishes and a cozy fireplace, ideal for everyday relaxation. The renovated kitchen includes stylish cabinetry, modern countertops, stainless steel appliances, and space for casual dining. An additional office/flex room provides versatility for work or hobbies. Both bedrooms offer natural light and easy access to the updated full bath. Main-floor laundry adds everyday convenience. Outside, enjoy updated landscaping, a private driveway, and multiple outdoor spaces perfect for entertaining, gardening, or simply enjoying the coastal surroundings. With vinyl siding, central air, and public sewer, this home offers low-maintenance living in a peaceful setting. Conveniently located near waterfront parks, community marinas, and local dining, this move-in-ready home is an excellent opportunity to enjoy the best of Shady Side living.

2 Beds ⋅ 1 Baths

Welcome to 4717 Frederick Avenue — a charming and updated cottage just two blocks from the West River in the Idlewilde on the Bay community. This 2-bedroom, 1-bath ranch-style home offers comfortable one-level living with thoughtful improvements throughout. Step inside to a bright, open living area featuring neutral finishes and a cozy fireplace, ideal for everyday relaxation. The renovated kitchen includes stylish cabinetry, modern countertops, stainless steel appliances, and space for casual dining. An additional office/flex room provides versatility for work or hobbies. Both bedrooms offer natural light and easy access to the updated full bath. Main-floor laundry adds everyday convenience. Outside, enjoy updated landscaping, a private driveway, and multiple outdoor spaces perfect for entertaining, gardening, or simply enjoying the coastal surroundings. With vinyl siding, central air, and public sewer, this home offers low-maintenance living in a peaceful setting. Conveniently located near waterfront parks, community marinas, and local dining, this move-in-ready home is an excellent opportunity to enjoy the best of Shady Side living.

4717 Frederick Ave, Shady Side

Listing courtesy of Next Step Realty. Contact:

Selling Office: Keller Williams Flagship.

$260,000

Offers cannot be submitted for seller review until 1/18/26. Set in a peaceful bayside community, this 3-bedroom, 1.5-bath home offers 1,320 square feet and the chance to create your vision near the water. The home features a rear deck and is within walking distance to the beach. The property requires substantial renovation and is priced accordingly. Sold As-Is with no repairs. A great opportunity for investors or buyers looking for a project in an established waterfront community. Cash or renovation loans only.

3 Beds ⋅ 2 Baths

Offers cannot be submitted for seller review until 1/18/26. Set in a peaceful bayside community, this 3-bedroom, 1.5-bath home offers 1,320 square feet and the chance to create your vision near the water. The home features a rear deck and is within walking distance to the beach. The property requires substantial renovation and is priced accordingly. Sold As-Is with no repairs. A great opportunity for investors or buyers looking for a project in an established waterfront community. Cash or renovation loans only.

1160 Oak Ave, Shady Side

Listing courtesy of Metro DMV Realty. Contact:

Selling Office: Douglas Realty LLC.

$230,500

Charming coastal cottage just two blocks from the water! Welcome to 4717 Frederick Avenue, a beautifully maintained 2-bedroom, 1-bath home nestled in the serene Idlewilde on the Bay community of Shady Side. Offering water access to the West River, this updated single-level home is perfect for year-round living, a weekend getaway, or a cozy investment opportunity. Step inside to find an efficient, light-filled layout with engineered wood flooring, a spacious living area with a wood-burning fireplace, and a flexible bonus room ideal for a home office or guest space. The kitchen provides easy flow for cooking and entertaining, while the updated bath and central air conditioning ensure modern comfort. Enjoy the outdoors with a modest backyard and off-street parking via a private driveway, this property offers ease of maintenance and everyday convenience. Located in a quiet waterfront community just minutes from marinas, parks, and dining—this is your opportunity to enjoy relaxed living near the Chesapeake Bay.

2 Beds ⋅ 1 Baths

Charming coastal cottage just two blocks from the water! Welcome to 4717 Frederick Avenue, a beautifully maintained 2-bedroom, 1-bath home nestled in the serene Idlewilde on the Bay community of Shady Side. Offering water access to the West River, this updated single-level home is perfect for year-round living, a weekend getaway, or a cozy investment opportunity. Step inside to find an efficient, light-filled layout with engineered wood flooring, a spacious living area with a wood-burning fireplace, and a flexible bonus room ideal for a home office or guest space. The kitchen provides easy flow for cooking and entertaining, while the updated bath and central air conditioning ensure modern comfort. Enjoy the outdoors with a modest backyard and off-street parking via a private driveway, this property offers ease of maintenance and everyday convenience. Located in a quiet waterfront community just minutes from marinas, parks, and dining—this is your opportunity to enjoy relaxed living near the Chesapeake Bay.

4717 Frederick Ave, Shady Side

Listing courtesy of Next Step Realty. Contact:

Selling Office: Next Step Realty.

$164,950

Build your dream home! few lots like this one. Dry area, very private & wooded lot surrounded by 73 acres in conservation easement. Enjoy peaceful nature. This lot has a right of way agreement along with lot at 6512 W Shady Side Rd See attached documents and maps. Located close to the west river and community Baseball diamond and basketball courts.

6508 Shady, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

Selling Office: HomeSource Pro Real Estate.

$143,850

Investor special in the charming Columbia Beach community of Shadyside. This quaint 2-bedroom, 1-bath home offers great potential for investors, renovators, or buyers looking to create their own coastal retreat. Inside, you'll find classic panel walls, a cozy fireplace, and a bright sunroom that adds extra living space and character. Nestled in a peaceful setting near the water, this property is full of opportunity for the right buyer to restore and reimagine. Bring your vision and make this hidden gem shine.

2 Beds ⋅ 1 Baths

Investor special in the charming Columbia Beach community of Shadyside. This quaint 2-bedroom, 1-bath home offers great potential for investors, renovators, or buyers looking to create their own coastal retreat. Inside, you'll find classic panel walls, a cozy fireplace, and a bright sunroom that adds extra living space and character. Nestled in a peaceful setting near the water, this property is full of opportunity for the right buyer to restore and reimagine. Bring your vision and make this hidden gem shine.

1502 Garst Rd, Shady Side

Listing courtesy of Fusion Elite Realty. Contact:

Selling Office: Non Subscribing Office.

$130,000

Beautiful Chesapeake Bay property for sale! Don’t miss this rare opportunity to build your dream home in the quaint, gated community of Columbia Beach, a serene neighborhood offering breathtaking bay views. Enjoy coastal living with a private pier, boat ramp, playground, tennis and basketball courts, and pickleball. Perfect for boating, fishing, sailing, kayaking, or simply relaxing by the water in a tight-knit, pet-friendly community that feels like stepping back into a simpler time, while staying close to modern conveniences. Convenient Location: 30 minutes to I-495 Beltway and Annapolis. 45 minutes to Washington, D.C. and the Woodrow Wilson Bridge Property Highlights: Served by public sewer Vacant lot — go and show anytime Motivated seller — bring all offers! Community amenities: gated access, piers, boat ramp, playgrounds, sports courts, and quiet, low-traffic streets Buyer to verify all building requirements, water frontage, riparian rights, and high/low water levels.

5314 Al Jones Dr, Shady Side

Listing courtesy of NextHome Mims Realty Group. Contact:

Selling Office: Schwartz Realty, Inc..

$110,000

REDUCED $45,000.00 ALL CASH OFFERS-FIRE DAMANGED INTERIOR- TOTAL REHAB-2 BR 1 Bath quiet secluded street. New Homes being built on same street. Owner reserves right to accept or reject any offer. Owner doing 1031 tax free exchange. Settlement 7-30 days. Haile Parkway/tax record Heile

2 Beds ⋅ 1 Baths

REDUCED $45,000.00 ALL CASH OFFERS-FIRE DAMANGED INTERIOR- TOTAL REHAB-2 BR 1 Bath quiet secluded street. New Homes being built on same street. Owner reserves right to accept or reject any offer. Owner doing 1031 tax free exchange. Settlement 7-30 days. Haile Parkway/tax record Heile

1432 Heile/Haile Pkwy, Shady Side

Listing courtesy of Flag Real Estate Inc.. Contact:

Selling Office: Samson Properties.

$107,000

Rare opportunity in Shady Side on 1.58 acres, just minutes from the Chesapeake Bay. 1451 Shady Rest Rd features a partially built home.. The groundwork is in place, and the next owner can bring their own vision to life. The property includes a permitted 3-bedroom septic system and a working well, giving you a strong starting point for a new build. This desirable South County area is seeing many buyers turn older or unfinished homes into custom retreats. The lot is ideal for anyone looking to build, finish a project, or own land close to the Bay lifestyle. This is a short sale being handled by a professional short sale team. Property is sold strictly as-is. All showings must be scheduled in advance and accompanied by a licensed agent. No unauthorized entry or walking the property. FEASIBILITY STUDY: Buyers will be allowed a 30-day feasibility period, including well and septic inspections. Buyers may request all existing documentation, including information on the well, septic, blueprints, and permits.

3 Beds ⋅ 1 Baths

Rare opportunity in Shady Side on 1.58 acres, just minutes from the Chesapeake Bay. 1451 Shady Rest Rd features a partially built home.. The groundwork is in place, and the next owner can bring their own vision to life. The property includes a permitted 3-bedroom septic system and a working well, giving you a strong starting point for a new build. This desirable South County area is seeing many buyers turn older or unfinished homes into custom retreats. The lot is ideal for anyone looking to build, finish a project, or own land close to the Bay lifestyle. This is a short sale being handled by a professional short sale team. Property is sold strictly as-is. All showings must be scheduled in advance and accompanied by a licensed agent. No unauthorized entry or walking the property. FEASIBILITY STUDY: Buyers will be allowed a 30-day feasibility period, including well and septic inspections. Buyers may request all existing documentation, including information on the well, septic, blueprints, and permits.

1451 Shady Rest Rd, Shady Side

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Home Towne Real Estate.

$52,050

Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility. With convenient access to Route 2 & Route 4, commuting to Annapolis, Baltimore, or Washington, D.C., is effortless—yet the moment you arrive, you'll feel miles away from the urban rush. Surrounded by lush trees and natural scenery, this blank canvas is ready for you to bring your vision to life. Shady Side is known for its close-knit community and outdoor recreation, from boating and fishing on the West River and Chesapeake Bay to exploring local parks and nature trails. Nearby shopping and dining ensure you have modern conveniences without compromising the charm of country living. Don’t miss this unique opportunity—contact us today to schedule a private tour and start planning your future in Shady Side, MD! 1408 Haile make up Lots 13 & 14, and are being offered along with 1410 Haile Pkwy (lots 15 & 16.). The owner of these lots own several others, also on Haile Pkwy, some of which are adjacent to each other. See 1445 & 1447 (being offered together) Please note the buyer is responsible for conducting all due diligence on lot including location, use, restrictions, and taxes.

1408 & 1410 Haile Pkwy, Shady Side

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

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