Shady Side MD Homes for Sale

This to-be-built custom modern farmhouse residence by local builder Laine Street Homes blends timeless design with modern luxury. Set on a premium 1.5-acre homesite, the property offers both privacy and functionality. Step onto the welcoming front porch and into a thoughtfully designed main level featuring a private office, formal dining room, and a spacious family room highlighted by large picture windows and a modern gas fireplace. At the heart of the home, the gourmet kitchen impresses with premium quartz countertops, herringbone tile backsplash, tasteful dove and pistachio cabinetry with dovetail joints and soft-close drawers, a walk-in pantry, farmhouse apron sink, and a large island with breakfast bar. Upstairs, the primary suite overlooks the private backyard and features luxury vinyl plank flooring, a walk-in closet, and a spa-inspired bath with a 7x6 walk-in shower boasting floor-to-ceiling tile. Additional highlights include 7-inch LVP flooring throughout the main level, shake siding with stone column bases, 2x6 construction, a 92% efficient HVAC system, and 30-year architectural shingles. With no HOA or restrictive covenants, this home offers rare flexibility and freedom in a highly desirable Anne Arundel County location, convenient to both Annapolis and Washington, D. C. Note: As the construction of this home has not been completed, pictures are from similar models and/or renderings.

6508 Shady, Shady Side

Listing courtesy of HomeSource Pro Real Estate. Contact:

$699,000

You can't beat the price for the WATERFRONT lifestyle in the Chesapeake Bay area! This stunning, open concept, 3-bedroom, 3-bath home was built in 2005 and has a PRIVATE dock -- blending modern updates, natural light, and serene water views. This home is the ideal size—not too big, not too small—offering the perfect balance of comfort, function, and privacy! Step inside an inviting open-concept main level to find luxury plank flooring throughout, and a cozy fireplace that anchors the living space. The chef’s kitchen is a showstopper, featuring a spacious island, sleek countertops, white cabinetry, and stainless appliances—ideal for entertaining and everyday living. The main level also offers a bedroom and full bath! The upper level boasts a dreamy primary suite overlooking the water, bathed in sunlight and featuring new, expansive windows . Enjoy the expansive STUNNING walk-in closet and spa-like en-suite bath with dual vanity, soaking tub, wainscoting, and a beautifully tiled frameless glass shower. Two additional bedrooms (one on main level) and bathrooms provide comfort , style and functionality with plenty of room for everyone! Outdoor living is just as special—this quiet retreat features a private dock, a fenced backyard, a paver patio and plenty of storage. Picture mornings with coffee and sunrise views, evenings on the patio watching the sunset reflect across the water, or weekends spent crabbing, kayaking, fishing, boating right from your own backyard! Not to forget a new roof (2024)! Situated in Shady Side, you’ll love the easy access to the Bay & only 25 minutes to Annapolis, 40 minutes to Washington, D.C., and 45 minutes to Northern Virginia. This home offers the perfect balance of waterfront tranquility and city convenience. So many local marinas, restaurants & the Chesapeake Yacht Club is nearby with memberships and slips available! Don’t miss this rare opportunity to occupy a turn-key waterfront property at this price point!

4922 Lerch Dr, Shady Side

Listing courtesy of Samson Properties. Contact:

$480,000

Nestled in the charming Cedarhurst on the Bay community, this delightful Cape Cod home offers a serene lifestyle with easy access to the beautiful river nearby. With four spacious bedrooms and two full bathrooms, this residence is perfect for creating lasting memories. The inviting living area features a cozy gas fireplace, ideal for gathering on cool evenings. Enjoy the outdoors on your generous 0.27-acre lot, complete with a shed for extra storage. The attached garage and ample driveway space provide convenience for you and your guests. With navigable water access, you can embrace a lifestyle filled with boating and fishing adventures. Cedarhurst on the Bay is a welcoming community that values connection and outdoor enjoyment, making it a wonderful place to call home. Experience the perfect blend of comfort and community in this lovely property! Cedarhurst on the Bay amenities include, picnic area, playground, fishing and crabbing pier and community house. Brand new carpets throughout the home, Exterior windows replaced 2026, new roof and gutters in 2025, new crawl space encapsulation 2024, HVAC replaced 2021.

1504 Cedarhurst Rd, Shady Side

Listing courtesy of Compass. Contact:

$409,990

One level living in the serene community of Idlewilde, this charming ranch-style home offers a perfect blend of comfort and functionality. With 1,339 square feet of thoughtfully designed space, this home features three bedrooms and two full bathrooms, ideal for both relaxation and entertaining. The family room, conveniently located off the kitchen is perfect for entertaining, while the formal dining room sets the stage for memorable meals.The property boasts granite counter tops, stainless steel appliances, including a built-in microwave, dishwasher, and electric range, making meal prep a breeze. The breakfast nook in the kitchen provides the perfect spot for the kitchen table for causul daily meals with your household. A dedicated laundry area with a washer and dryer adds to the home's practicality. Outside, the 0.17-acre lot features private access to the West River with the community pier! Take in the sunsets just a short stroll away, perfect for those who appreciate nature and water activities. A concrete driveway accommodates up to four vehicles, ensuring ample parking for guests. With its excellent condition and thoughtful layout, this home is a true gem, ready for you to call this your very own "Home Sweet Home" 100% financing approved with the no downpayment program available!

4734 Idlewilde Rd, Shady Side

Listing courtesy of RE/MAX One. Contact:

$145,000

Discover an extraordinary opportunity to own a stunning 1.09-acre parcel of land. Nestled in a serene setting, this exceptional lot backs to lush trees, offering a private sanctuary that seamlessly blends nature with sophistication. Imagine crafting your dream estate amidst the tranquil backdrop of towering trees. Envision grand residence designed to your specifications, complete with expansive outdoor spaces that invite entertaining and relaxation. The natural beauty surrounding the property provides an idyllic setting for a luxurious garden, an outdoor living area that captures the essence of leisure. The absence of an association fee means you have the freedom to create without restrictions, allowing your vision to flourish. With no association amenities to limit your creativity, you can design a lifestyle that reflects your unique tastes and desires. This is a rare chance to embrace exclusivity and privacy in a location that feels both secluded and connected. The lot's generous size offers ample space for a sprawling estate, complete with all the high-end features you desire. Picture expansive windows that frame the picturesque views, gourmet kitchens equipped with top-of-the-line appliances, and lavish master suites that serve as personal retreats. The possibilities are endless, limited only by your imagination. This property is more than just land; it's an invitation to a lifestyle defined by tranquility. Whether you seek a peaceful retreat from the hustle and bustle or a vibrant space for entertaining, this lot provides the perfect foundation for your vision. Seize this rare opportunity to create a luxurious haven that reflects your personal style and aspirations. With its unparalleled natural surroundings and the promise of a sophisticated lifestyle, this property is poised to become the backdrop for your most cherished memories. Don't miss your chance to invest in a future filled with elegance and serenity. Your dream home awaits

4901 Idlewilde Rd, Shady Side

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

$699,000

Come Live the Bay Lifestyle! Welcome to 1244 Pine Avenue, a charming Chesapeake Bay retreat in Shady Side, Maryland, offering beautiful water and marina views, exceptional outdoor living, and the relaxed charm of coastal Maryland. Wake up to breathtaking sunrises, watch sailboats pass by, and enjoy peaceful evenings overlooking the bay. Located in the desirable Cedarhurst community, this inviting home offers the perfect opportunity to embrace waterfront living with a residents only marina across the street. Inside, the light filled living and dining areas feature a fireplace and expansive picture windows framing beautiful water views. The updated kitchen is appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range. Just beyond, a charming screened-in porch creates the perfect setting for morning coffee or al fresco dining. The spacious rear family room offers additional living space with sweeping bay views and sliding glass doors opening to the deck and fully fenced backyard, creating a seamless connection between indoor and outdoor entertaining. The main level includes a versatile bedroom ideal for guests or a home office, while upstairs, three generously sized bedrooms offer comfortable accommodations, including a spacious primary bedroom with beautiful Chesapeake Bay views. Additional highlights include a newer roof, new washer and dryer, generous outdoor entertaining areas, and a large storage shed is wired and has electricity. For boating enthusiasts, the nearby residents only marina offers boat slips reportedly available for $350 annually, providing convenient access to the Chesapeake Bay. Cedarhurst's waterfront community center, playground, beach, and picnic areas further enhance the neighborhood's coastal lifestyle. Whether as a primary residence or weekend retreat, 1244 Pine Avenue offers an exceptional combination of water views, generous outdoor living, boating access, and the tranquility of Shady Side's beloved Chesapeake Bay community.

1244 Pine Ave, Shady Side

Listing courtesy of Compass. Contact:

$349,900

MECHANICS/WORKSHOP DREAM. Nestled in the serene Shady Side community, this charming ranch-style home offers a perfect blend of comfort and functionality. With 1,489 square feet of thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, ideal for both relaxation and entertaining. Step inside to discover a warm and welcoming interior, highlighted by a cozy breakfast area and a combination kitchen/dining space that encourages gatherings. The kitchen is equipped with stainless steel appliances, including a gas oven/range and a convenient dishwasher, making meal prep a delight. Enjoy the ease of main-floor laundry and the comfort of ceiling fans throughout. The exterior of the home is equally appealing, featuring low-maintenance vinyl siding and a spacious lot of over half an acre that backs to lush trees, providing a tranquil backdrop. Outdoor living is enhanced by a charming patio and porch, perfect for morning coffee or evening relaxation. The property also includes an oversized detached garage with car lift and a shed, offering ample storage and workspace. Perfect for the mechanic with side jobs or projects to work on. Parking is a breeze with a circular gravel driveway and additional spaces for guests or projects. This home is not just a place to live; it's a sanctuary where you can unwind and create lasting memories. Experience the perfect blend of indoor comfort and outdoor beauty in this delightful property.

1462 Columbia Beach Rd, Shady Side

Listing courtesy of RE/MAX Realty Group. Contact:

$499,900

Nestled in the charming Cedarhurst on the Bay community, this delightful split foyer home offers a perfect blend of comfort and convenience. This well-maintained residence features four spacious bedrooms and three full bathrooms, ideal for both relaxation and entertaining. Step outside to discover a serene outdoor oasis, complete with a hot tub for unwinding after a long day. The property also includes a garage and a shed, providing ample storage for all your needs. Enjoy the beauty of nature with easy access to the stunning Chesapeake Bay, where community docks invite you to explore the water and create lasting memories. The neighborhood is known for its friendly atmosphere and strong sense of community. Residents benefit from nearby parks, perfect for leisurely strolls or picnics, and excellent public services that enhance the quality of life. With a walkout basement and a cozy fireplace, this home is designed for comfort and warmth. Experience the joys of living in Cedarhurst on the Bay, where community spirit meets the tranquility of waterfront living. This home is not just a place to live; it's a place to thrive. professional pictures to come.

1183 Cedar Ave, Shady Side

Listing courtesy of United Real Estate Premier. Contact:

$574,990

Home is ready for immediate occupancy. Coastal Living Just Steps from the Chesapeake Bay! Schaefer Homes invites you to make this beautifully designed coastal-style residence your own located across the street from the bay offering nice water views. Offering over 3 stories of wide open living with LVP flooring through out (Carpet in 2 bedrooms). From the classic board-and-batten siding to the welcoming front porch, the exterior sets a striking first impression. Upper level offers water views and an open-concept layout that seamlessly connects the dining and family rooms, offering the perfect setting for everyday living or entertaining. At the heart of the home is an upgraded kitchen with oversized island, upgraded countertops, stainless steel appliances, and abundant cabinetry—ideal for casual meals or gatherings with friends. A private home office (or flexible choice room) on the main level adds convenience, while upstairs the serene owner’s suite boasts a large picture window with Bay views, a spacious walk-in closet, and a spa-inspired bath with a luxury shower. Walk to community pier, boat ramp, playground, tennis courts and more. Renderings and photos are for illustrative purposes only and may show optional features, upgrades, or configurations not included as standard. Actual features, finishes, and layouts may vary. Flood insurance is approximately $650.00 year. $5,000 in closing assistance with preferred lender and title company.

5314 Al Jones Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$464,999

REDUCED ALMOST 25K >>> HURRY THIS PROPERTY WILL NOT LAST LONG AT THIS PRICE>>>>.Nestled in the charming Avalon Shores community, this delightful Colonial home offers a perfect blend of comfort and modern living. This 3 bedroom and 2.5 bath has a thoughtfully designed space, ideal for both relaxation and entertaining. Step inside to discover an inviting open floor plan adorned with beautiful LVT floors. The huge eat-in kitchen with under cabinet lighting and stainless appliances is great for a family & entertaining with a huge dining area off kitchen. The spacious primary suite offers a serene retreat with new LVT floors and a newly remodeled bath with new vanity, new LVT floors, lighting and toilet. The separate laundry room upstairs is and added bonus!! Outside the extensive hardscape with new concrete walkways complements the lovely 17 x17 back patio and 28x10 back deck and front porch all perfect for enjoying morning coffee or evening gatherings with family and friends. The level lot with maintenance free fenced in yard provides a lovely outdoor space, while the attached garage and asphalt driveway ensure ample parking. The home is wired with a full subpanel for in house generator. There is an encapsulated crawlspace with Aquaguard w/ EZ Breath climate control and dehumidifier. Residents of Avalon Shores enjoy exclusive access to common grounds and picnic areas, a pier/dock, and playground, fostering a sense of community and outdoor enjoyment. With water and lake privileges, you can embrace a lifestyle filled with leisure and recreation. This home is not just a property; it's a sanctuary where family memories are made. Experience the perfect blend of comfort, convenience, and community in this exceptional family oriented home.

1240 Hawthorne St, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

$599,990

Huge Price Adjustment + $5,000 Closing Help! December Delivery at Cedarhurst on the Bay* Welcome to Cedarhurst on the Bay, where every day feels like a coastal escape. This beautifully crafted home blends timeless charm with modern living, with stunning Chesapeake Bay views and classic board-and-batten siding. The open-concept main level is filled with natural light, connecting the dining area and family room. The kitchen features an oversized quartz island, stainless steel appliances, and generous cabinetry, and a main-level home office or flex room adds versatility. Upstairs, the owner’s suite offers large windows, an expansive walk-in closet, and a spa-inspired bath with a luxury shower. Outside, Cedarhurst’s four acres of community-owned waterfront include a community center, playground, picnic areas, ball fields, and open lawns overlooking the wetlands and water. With direct access to the Bay, boating, fishing, and sunset views are always within reach. December will be here before you know it. Don’t wait. Schedule your appointment today! *Closing cost assistance terms and conditions apply.

1235 Spruce Ave, Shady Side

Listing courtesy of Blackwell Real Estate, LLC. Contact:

$500,000

Motivated Seller. Owners have relocated. Will consider any reasonable offer. Now is the time to take a fresh look at this beautifully designed 2022-built home, where modern style, thoughtful details, and a peaceful wooded setting come together. Move-in ready and filled with natural light, this home offers the space and flexibility buyers are looking for—without the wait or expense of new construction. Step inside to an open two-story foyer and into the inviting main living area with vaulted ceilings. Nine-foot ceilings throughout the home, charming cottage-style windows, and an open layout create an airy, comfortable feel. LVP flooring flows throughout the living room, kitchen, and wide hallway, making everyday living and entertaining effortless. The kitchen is a standout, featuring granite countertops, soft-close cabinetry, oil-rubbed bronze fixtures, and a center island with seating. There’s plenty of room for a dining table, creating an easy gathering space for family and friends. The main level offers three bedrooms including a spacious owner’s suite with two closets providing excellent storage, while the distinctive en-suite bath features dual sinks, granite countertops, a walk-in shower, custom wall trim. The two additional bedrooms feature custom molding, decorative wall treatments, and stylish finishes. The hall bath includes a granite vanity and shower/tub combination. And there’s even more living space downstairs! The lower level features a large recreation room with sliding glass doors to the backyard, a flexible fourth bedroom perfect for guests, a home office, gym, or hobby room, plus another full bath. This versatile lower level gives you room to spread out, work from home, entertain, or accommodate overnight guests. Outside, raised garden beds are ready for your favorite flowers, herbs, and vegetables. The mature, wooded backdrop provides a peaceful sense of privacy and a beautiful setting to enjoy year-round.

1411 Haile Pkwy, Shady Side

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

$1,065,000

3 Beds ⋅ 5 Baths

Waterfront living at its finest in Avalon Shores on South Creek! This 3-bedroom, 4.5-bath home features a versatile study/bonus room, beautiful wood floors, updated kitchen and baths, and modern fixtures throughout. Enjoy water views from the expansive screened-in back porch or multiple decks spanning the second and third levels. The waterfront setup is ideal for boating enthusiasts with a remote-controlled boat lift and three jet ski lifts. A 2-car garage provides convenient parking and storage. New roof installed in 2023, while bulkhead was redone in 2016. Enjoy relaxing, entertaining, and life on the water!

5060 Lerch Dr, Shady Side

Listing courtesy of Redfin Corp. Contact:

$625,000

Imagine coming home to nearly an acre of privacy, beautiful sunsets, and the freedom to enjoy life exactly as you choose. Welcome to 1221 Bast Lane, where beautifully renovated interiors, exceptional outdoor space, and an extraordinary detached garage create a property that truly stands apart. Designed for comfortable, effortless living, this beautifully updated Craftsman-style home offers over 2,000 square feet on one level, with four bedrooms, two full baths, and inviting spaces for gathering with family and friends. The gorgeous kitchen, complete with an oversized island, stainless steel appliances, and beautiful finishes, becomes the heart of the home. Picture holiday celebrations, Thanksgiving dinner, Christmas mornings by the fireplace, and evenings filled with laughter around the table. The spacious primary suite offers a peaceful retreat, while the thoughtfully designed floor plan provides the perfect balance of everyday comfort and entertaining. And then there's the garage! An incredible 1,500-square-foot detached building with three oversized bays opens the door to endless possibilities. Imagine housing your prized automobiles, storing your boat and recreational toys, creating the ultimate workshop, or designing a spectacular space for your hobbies and collections. For those who appreciate their cars, boats, tools, and toys, this is an exceptional opportunity! Outdoors, nearly an acre becomes your own private escape. Enjoy summer barbecues, celebrations under the stars, afternoons with family and friends, or simply relaxing on the expansive deck as the evening sky fills with the colors of sunset. From festive holiday gatherings to quiet Sunday mornings, this property offers the space to make every season memorable. Extensively renovated in 2022, with additional roofing and siding improvements in 2023, the home combines thoughtful updates with the freedom of no HOA. Located near the Chesapeake Bay and West River, boating, fishing, waterfront dining, and the relaxed charm of Shady Side are all part of the lifestyle. Beautifully renovated, nearly an acre, effortless one-level living, and an extraordinary three-bay garage—1221 Bast Lane is more than a place to live. It's a place to celebrate, entertain, pursue your passions, and create lasting memories. Come experience everything this exceptional property has to offer!

1221 Bast Ln, Shady Side

Listing courtesy of Coldwell Banker Realty. Contact:

$419,000

This beautifully updated 3-bedroom, 2-full-bath rancher offers comfortable one-level living on a full acre. The entire interior was completely renovated in 2023, showcasing fresh, modern finishes throughout. Additional improvements since then include a new roof, gutters, and water filtration system. Outside, enjoy a one-car garage, abundant parking, and two exterior storage sheds offering plenty of space for tools, equipment, and more. The spacious property provides room to spread out and enjoy the outdoors, while the location just minutes from the waterfront offers convenient access to Chesapeake Bay boating, kayaking, fishing, crabbing, and other recreational activities. This home is approximately 20 minutes from the Suitland Metro station, 30 minutes from Joint Base Andrews, and 30 minutes from Annapolis. With extensive interior updates, valuable exterior amenities, and convenient access to waterfront recreation, this property is ready to welcome its next owner!

1437 Cedarhurst Rd, Shady Side

Listing courtesy of Samson Properties. Contact:

$380,000

Large lot ready for you to build your private compound! 8.5 acres contains wetland areas. Located in a water-privileged community and two blocks to the Chesapeake Bay. Cedarhurst on the Bay has a private marina, pier, beachfront and community house for owners use only. Located on a peninsula, Cedarhurst on the Bay has easy access to the water and amazing views of the Bay! Nearby Annapolis, Baltimore, Washington, DC, BWI and DCA airports. You're buying more than land to build on, you're buying that water-privileged lifestyle you've always dreamed of! Nearby restaurants, shopping, parks, the Capt. Salem Avery House and The Lula G. Scott Community Center (both on the historic registry) and more. Across the street from the historic "The Brick House" (formerly "The Bay View Inn"), which is undergoing renovations. Get a feasibility study done to see what an amazing home compound you can create in this wonderful water privileged community surrounded by nature. May be possible to build one or two houses on this property. Confirm with the county. Owners willing to split the cost of a feasibility study 50/50 if buyers proceed to closing. Buyer to perform all due diligence. All offers considered.

1495 Cedarhurst Rd, Shady Side

Listing courtesy of Taylor Properties. Contact:

$515,000

Welcome home to this beautifully maintained split-foyer in Cedarhurst on the Bay, Shadyside's sought-after water-privilege community. Built in 2015, this 3-bedroom, 2.5-bath home offers 1,838 total finished square feet, including a bright main level with cathedral ceilings and a finished lower level with a half bath — ideal for entertaining or extra living space. Stone and vinyl siding give it great curb appeal, and the 2-car attached garage plus 2-car driveway provide 4 total parking spaces. Owned solar panels keep utility costs low year-round. Just one block to the Chesapeake Bay with community water access, and an easy commute to Annapolis, DC, and Baltimore. Don't miss your chance to own in one of the area's most desirable water-privilege neighborhoods.

1175 Maple Ave, Shady Side

Listing courtesy of Cummings & Co. Realtors. Contact:

$409,990

Welcome to the Chesapeake Bay lifestyle in the waterfront community of Cedarhurst! Just one block from the Bay, this picture-perfect Colonial combines classic curb appeal, comfortable living spaces, and the kind of community amenities that make everyday life feel a little more like vacation. Start your mornings on the welcoming front porch and spend summer evenings entertaining on the rear deck overlooking the lush landscaping. Inside, the inviting living room features a cozy wood-burning fireplace, while the spacious kitchen offers painted cabinetry, stainless steel appliances, and plenty of room for an eat-in dining area. Upstairs, you’ll find three generously sized bedrooms, including a spacious primary suite with vaulted ceilings and a private en-suite bath. Two additional bedrooms share a dedicated hall bath. Major updates include a NEW ROOF in 2022 and HVAC replaced in 2021. But the Cedarhurst lifestyle may just be the best part! Stroll down to the community waterfront where you’ll find a picnic area and playground overlooking the Chesapeake Bay—the perfect spot to catch the sunset to your right or watch the sunrise to your left. Launch your kayak or jet ski from the community boat ramp, or take advantage of available boat slips for just $400 per year, per slip. Residents also have exclusive access to rent the Cedarhurst Community Center for parties and gatherings. From boating and waterfront picnics to catching both sunrise and sunset along the Bay, this is more than a home—it’s the Chesapeake lifestyle you've been looking for. This property is 100% financing approved, no downpayment local program available! Welcome home!

1193 Oak Ave, Shady Side

Listing courtesy of RE/MAX One. Contact:

$299,900

Welcome to this charming 4-bedroom, 2-bath home in the desirable Snug Harbor community of Shady Side. Offering approximately 1,930 square feet of living space, this property features a spacious layout, detached garage, and generous yard with plenty of room to enjoy outdoor living. Conveniently located near marinas, parks, local dining, and Chesapeake Bay recreation, this home presents a wonderful opportunity to enjoy the relaxed waterfront lifestyle with easy access to Annapolis. This property has an exclusive boat slip!

1704 Maryland Ave, Shady Side

Listing courtesy of Sell Your Home Services. Contact:

$440,000

5 Beds ⋅ 2 Baths

Don't Miss this Amazing Opportunity in the Waterfront Community of Cedarhurst by the Bay tucked away on the quiet Shady Side Penninsula. This Spacious 5 Bedroom, 2 Full Bath home sits just steps away from the amazing community waterfront offering stunning views of the Chesapeake Bay from the Upper Balcony and a multitude of community ammenities. Wake up to breathtaking sunrises and end your evenings watching colorful sunsets. Enjoy the everyday vacation life on the expansive community waterfront with panoramic views and and refreshing coastal breezes. Enjoy time with family and friends at the picnic areas, ballfields and playground. The community pier stretches out into the bay, has a gazebo and is perfect for fishing and crabbing. The Community Harbor has over 60 slips that can be reserved by community members and direct has access to the bay serving both power boats and sail boats. Whether you are launching a boat or relaxing on the deck, this is coastal living at its finest! Your everyday vacation starts here! Cedarhurst is a Special Community Benefit District. Seller is offering property "As is".

1220 Grove Ave, Shady Side

Listing courtesy of Coldwell Banker Realty. Contact:

$699,000

5 Beds ⋅ 3 Baths

MAJOR PRICE IMPROVEMENT AND $5,000 SELLER CONTTRIBUTION TOWARDS BUYER'S CLOSING WITH ACCEPTABLE CONTRACT. Rare Opportunity with 2 detached homes on 4 Flat, Usable Acres in Shady Side! Welcome to 6066 Shady Side Rd, an incredible property offering endless versatility, income potential, and space to grow. Situated on 4 expansive, flat acres, this unique listing features two standalone ranch style homes, perfect for multigenerational living, live-and-rent setups, or investment portfolios. 🏡 Main Residence (3 Beds | 2 Baths) Turnkey Interior: Beautiful updated finishes, including durable luxury vinyl plank flooring and modern recessed lighting throughout. Gourmet Kitchen: Bright and updated with crisp white soft close cabinetry, granite countertops, tile backsplash, and sleek stainless-steel appliances. Thoughtful Layout: Offers a dedicated laundry room, spacious living areas, and stylishly tiled bathrooms with modern vanities. Outdoor Living: Relax or entertain on the front deck, back deck, or under the convenient 2-car attached carport. 🏡 Detached ADU / Guest House (2 Beds | 1 Bath) Private Setting: Tucked neatly at the rear of the lot with its own charming drive and mature tree-lined backdrop. Fully Equipped: Move-in ready home featuring an open-concept living area, dedicated kitchen space, and updated flooring. Income Potential: Ideal as a high-yield rental, guest house, home office, or private residence for family members. 🌳 The Land & Potential 4 Flat Acres: Massive, level lawn space ideal for gardening, outdoor recreation, or adding outbuildings/workshops. Future Investment: Flat topography provides great potential for future subdivision (buyer to verify local zoning/subdivision requirements). Whether you’re looking to offset your mortgage with rental income or searching for the ultimate multi-family retreat near the Chesapeake Bay, this property delivers unbeatable value and flexibility in Shady Side!

6066 Shady, Shady Side

Listing courtesy of Century 21 Downtown. Contact:

$998,000

Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking panoramic views stretching all the way to the Bay Bridge. Meticulously maintained and truly move-in ready, this exceptional property combines luxury, comfort, and the best of coastal living. The main level features beautiful hardwood floors, a spacious gourmet kitchen with granite countertops, stainless steel appliances, and an open layout overlooking the inviting family room with a gas fireplace and spectacular Bay views. A main-level bedroom and full bath provide the perfect accommodations for guests. Upstairs, you'll find three additional bedrooms and two full baths, including a stunning waterfront primary suite. Wake up each morning to endless water views through walls of glass, then step onto your private covered terrace to enjoy your morning coffee while watching the sunrise over the Chesapeake Bay. Outside, your private pier offers the perfect place to fish, crab, or take the boat for a day on the water. Cruise to the many nearby waterfront restaurants and marinas, or simply relax and enjoy the peaceful waterfront setting. Conveniently located with an easy commute to Annapolis, Washington, D.C., and Baltimore, this remarkable home is nestled in the charming waterfront community of Felicity Cove. If you've been dreaming of exceptional Chesapeake Bay waterfront living, this is a home you won't want to miss.

4721 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$249,900

1 Beds ⋅ 1 Baths

This is an estate sale. Buyer to verify all information. Cute 1 BR 1BA cottage located a few hundred yard from the bay. Needs some TLC but livable. Roof is less than 7 years old. Solar panels are owned and not leased. Includes boat slip number 7. Would make a great getaway home or investment property. Sold strictly "as is". Seller will make no repairs.

1737 Cedar Ave, Shady Side

Listing courtesy of RE/MAX Realty Plus. Contact:

$220,000

Wonderful 23-acre property in Southern Anne Arundel County offering a peaceful setting with level terrain and a mix of open and wooded areas. A home formerly occupied the property but was lost to a fire decades ago; no visible foundation remains. Sewer service is available at the road, providing added convenience for your dream home. Ideally located near the Chesapeake Bay, this property is surrounded by abundant wildlife and waterfowl, making it a great opportunity for nature lovers. Enjoy easy access to the water at Franklin Point State Park, located approximately one mile away, where you can explore the shoreline and experience the area's natural beauty.

1514 Columbia Beach Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$799,000

Welcome to 1211 Linton Lane, where space, comfort, and water-access living come together in the heart of Shady Side. Located near the Chesapeake Bay, local marinas, boat ramps, parks, and fishing spots, this home offers the ideal opportunity to enjoy Southern Anne Arundel County’s relaxed coastal lifestyle. Set on a generous lot, the property provides plenty of outdoor space for entertaining, gardening, relaxing, or creating your own private retreat. Inside, the home offers spacious living areas, comfortable bedrooms, flexible living space, and updated appliances that make everyday living easy and functional. One of the standout features is the convenient carport and expansive driveway with room to accommodate up to six cars, giving you plenty of space for guests, multiple vehicles, work trucks, boats, trailers, or recreational equipment. Whether you are hosting weekend gatherings, heading out for a day on the water, or simply looking for room to spread out, this property delivers the space and convenience buyers are looking for. Enjoy the water-access lifestyle Shady Side is known for, with nearby opportunities for boating, kayaking, paddleboarding, fishing, and peaceful days along the Chesapeake Bay. All of this while still being conveniently located near Annapolis, Edgewater, shopping, dining, commuter routes, and everyday essentials. 1211 Linton Lane is a wonderful opportunity for buyers looking for space, charm, convenience, and the chance to live close to the water.

1211 Linton Ln, Shady Side

Listing courtesy of Keller Williams Capital Properties. Contact:

$300,000

Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with convenient access to local marinas, parks, dining, and commuter routes. The interior presents a functional layout with generous living spaces, abundant natural light, and endless potential for customization. Enjoy the privacy of the surrounding landscape while taking advantage of the area's relaxed coastal lifestyle. Whether you're looking for a primary residence, a weekend retreat, or an investment opportunity, this property provides a wonderful chance to create your vision in a desirable Anne Arundel County location. Don't miss the opportunity to explore the possibilities this home has to offer. Some photos contain virtual renovation and staging.

6372 Shady, Shady Side

Listing courtesy of Maryland Realty Connection. Contact:

$680,000

***OPEN HOUSE*** Sun 11/8 11am-1pm. Welcome to the Honey Hole of the South Creek! New roof & gutters freshly installed! Welcome to your own private waterfront retreat nestled at the peaceful head of South Creek, where breathtaking views, abundant wildlife, and the ultimate Chesapeake Bay lifestyle come together. Perfectly positioned on a beautifully level lot, this exceptional property offers a private pier ideal for launching a kayak, canoe, paddleboard, or boat, while the nearby community marina provides access to deep-water slips for larger vessels. Residents also enjoy access to the community beach, making every day feel like a vacation. An added bonus is the inclusion of the adjacent Lots 17 & 18 (4907 Thomas Drive), providing additional privacy, flexibility, and future possibilities. Step inside to discover a bright, open floor plan designed to maximize both the water views and natural light. The spacious kitchen features a center island, ample cabinetry, and a sunny breakfast area highlighted by a large picture window overlooking the creek—an unforgettable place to enjoy your morning coffee. The adjoining living room offers the warmth and charm of a wood-burning stove along with sliding glass doors leading to the expansive wraparound screened porch, creating the perfect space for indoor-outdoor entertaining or simply relaxing while watching osprey, herons, and other local wildlife. Large pantry area for additional storage and separate dining room for additional room to spread out. Upstairs, all three bedrooms are thoughtfully situated, including a spacious primary suite that serves as a true waterfront sanctuary. Wake up each morning to panoramic water views from your private balcony, then unwind in the en-suite bath featuring a walk-in closet and plenty of room to recharge after a day on the water. The additional bedrooms are generously sized, with one also enjoying beautiful water views, and are served by a second full bathroom on the upper level. This home has been thoughtfully updated for peace of mind and long-term enjoyment. It may say it was built in 1941, but this home went through an extensive remodel in 1991 taking the original beach bungalow to the oversized colonial it is today. Recent improvements include a brand-new roof (2026), renovated Tigerwood deck, and a professionally encapsulated crawlspace complete with a dehumidification system. If you’ve been dreaming of a waterfront lifestyle that combines privacy, natural beauty, and everyday comfort, this is a rare opportunity to own a special piece of Southern Anne Arundel County. Whether you’re boating, crabbing, kayaking, entertaining on the screened porch, or simply enjoying the peaceful creek views, you’ll quickly understand why this location is so special.

1241 Johnson Dr, Shady Side

Listing courtesy of RE/MAX One. Contact:

$149,900

WATERFRONT OPPORTUNITY!! Discover the perfect setting to build your dream home or weekend retreat on this waterfront lot offering breathtaking views of the Chesapeake Bay. Nestled in the quiet, secluded community of Columbia Beach, this approximately 4,450-square-foot homesite is already serviced by public sewer, making it an exceptional opportunity to bring your vision to life. Wake up to stunning sunrises, enjoy the peaceful waterfront surroundings, and embrace the laid-back Chesapeake lifestyle with boating, fishing, kayaking, and endless opportunities to relax by the water. Whether you're looking to create a full-time residence or a private coastal escape, this rare waterfront property offers the chance to own a slice of the Bay in a tranquil setting. Don't miss this unique opportunity!

5209 Al Jones Dr, Shady Side

Listing courtesy of CENTURY 21 New Millennium. Contact:

$625,000

Enjoy breathtaking views of the Chesapeake Bay from this charming home in the quaint waterfront community of Felicity Cove. The ground level features two bedrooms (one without a closet), a full bathroom, and a second kitchen, making it an ideal space for guests, extended family, or multi-generational living. The main living area is located on the second floor to take full advantage of the spectacular bay views. This level also includes the primary kitchen, a bright sunroom, and deck—perfect for relaxing or entertaining while enjoying the waterfront scenery. The upper level offers a serene primary suite with stunning Chesapeake Bay views, a private bath featuring a Jacuzzi tub, and an additional guest bedroom. Experience the feeling of year-round vacation living with community amenities that include a pier and boat ramp, providing easy access to the bay.

4734 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$599,900

**Open House this Saturday September 12th 10am-12pm!** Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarged rear decking, ADT Alarm system, generator hook up. 2023 full kitchen renovation - upgraded cabinetry, leathered granite counter-top, farmhouse sink, back splash upgraded stove top / microwave, and all new wood flooring on main level. Renovated half bath-2023. 2024 new water softener / well pump (relocated to garage), and 66-gallon water heater. 2025 - replaced roof, replaced HVAC, Primary bathroom renovation (cabinet, vanity, shower, upgraded flooring, replaced toilet, fogless mirror), and replaced dryer vent. Don't miss the opportunity to purchase this stunning home sitting on a 1-acre natured filled lot. Please schedule all showings via Showing Time.

1582 Snug Harbor Rd, Shady Side

Listing courtesy of Maryland Waterfront Properties LLC. Contact:

$285,000

3 Beds ⋅ 1 Baths

Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Peninsula, conveniently located between Annapolis and Deale Maryland. This cute, updated rancher style home offers a rare affordable opportunity to enjoy Chesapeake Bay living, just one hour from the City. So much potential! Make it your weekend retreat, an Air B&B, or perhaps a tranquil place to retire, without the extra expense of association fees! Inside, you'll find an updated kitchen featuring stainless steel appliances, granite countertops, ceramic tile flooring, and a stylish backsplash. The bathroom has been renovated with an updated vanity, toilet, and jetted tub. Modern wood flooring in the living room adds warmth that complements any décor. A new roof provides peace of mind for years to come. Outside, enjoy a semi-private, ¾ fenced in yard, a spacious storage shed, and off-street parking for up to four vehicles. Community amenities include a boat ramp, marina with boat slips, fishing pier, playground, gazebo, and a beautiful waterfront community center available for private events. Conveniently located within commuting distance of Washington, DC, Annapolis, Chesapeake Beach, and NAS Patuxent River.

1172 Cedar Ave, Shady Side

Listing courtesy of Weichert, REALTORS. Contact:

$470,000

Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its original builders of the home. Situated on over one-third of an acre, this well-maintained 3-bedroom, 2.5-bath residence offers the perfect blend of comfort, space, and community living. The fully fenced backyard provides an ideal setting for entertaining, family gatherings, or simply relaxing outdoors. Inside, the updated kitchen features granite countertops and stainless steel appliances, while gorgeous hardwood floors with custom inlay accents add warmth and character throughout the home. The spacious primary suite boasts vaulted ceilings and a private en-suite bath, creating a comfortable retreat. All bedrooms are generously sized and offer ample closet space. Enjoy peaceful mornings with a cup of coffee or unwind in the evenings on the charming enclosed front porch, perfect for reading or taking in the neighborhood atmosphere. Residents of Avalon Shores enjoy exceptional community amenities, including two playgrounds, baseball fields, a community boat launch, and water access. Opportunities like this are rare in such a desirable waterfront community. Don't miss your chance to make this wonderful home your own!

4951 Bonniewood Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$765,000

Waterfront living with a private dock—all for only $765,000! Get a lower mortgage payment! Seller willing to supplement rate discount, 2-1 Buydown: 2% lower interest rate in Year 1, and 1% lower in Year 2. Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops, stainless steel appliances, a center island with seating, and a sleek range hood. Large bay windows flood the main level with natural light. Enjoy beautifully finished bathrooms, a bedroom on the main living level, and two spacious bedrooms upstairs. Want more room? There’s extra space for an office, playroom, or a bedroom in the loft. Step outside to discover 63 feet of premier waterfront along South Creek. The spacious fully-fenced backyard and private dock with electric & water offer the perfect launchpad for kayaking, paddleboarding, or simply soaking in the tranquil scenery. The primary bedroom has a private balcony to enjoy the creek views. Enjoy peace of mind with new kitchen appliances (dishwasher, fridge - 2025; range hood - 2026), new roof (2025), new HVAC (2026), and sealing work and crawl space encapsulation (2020). Complete with an attached two-car garage with a 12kW Level 2 EV charger, offering secure inside access, and the convenience of a personal air-conditioned gym (or open the doors and enjoy the view and sounds of nature!). This turnkey property is a rare opportunity to live the ultimate waterfront lifestyle. Schedule your tour today!

4950 Bonniewood Dr, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

$120,000

Sale includes both 1186 & 1188 Poplar Ave. Lots: 10,11,12,13 Rare opportunity to purchase two adjoining parcels totaling approximately 19,000 square feet or nearly 1/2 acre in the water-privileged community of Cedarhurst on the Bay. Build your dream home and enjoy the relaxed Chesapeake Bay lifestyle that makes Shady Side one of Anne Arundel County's hidden gems. Community amenities include Bay access, a beach, boat ramp, pier, clubhouse, and playground, providing endless opportunities for boating, fishing, kayaking, sailing, swimming, and waterfront recreation. Whether you're spending the day on the water, enjoying a sunset by the Bay, or simply embracing the slower pace of coastal living, this location offers the perfect balance of recreation and tranquility. Public sewer hookup is available, and the property is conveniently located within commuting distance of Annapolis, Baltimore, and Washington, D.C. A rare opportunity to secure an oversized homesite in an established waterfront community and create the home you've always envisioned.

1186 & 1188 Poplar Ave, Shady Side

Listing courtesy of Keller Williams Flagship. Contact:

$450,000

Welcome to this beautifully maintained Colonial perfectly positioned on a desirable corner lot in the water-oriented community of Cedarhurst—where Chesapeake Bay living is part of everyday life. Just in time for summer, enjoy the opportunity to lease a boat slip for only $400 per year with direct access to the Chesapeake Bay, making weekends on the water easier than ever. Inside, you’ll find hardwood floors throughout and a spacious layout designed for both comfortable living and entertaining. The oversized 21’ x 23’ primary suite offers a true retreat with plenty of room to unwind, while the additional bedrooms are generously sized as well. The main level features a versatile gym/office space that could easily serve as a fourth bedroom, guest room, or playroom depending on your needs. The heart of the home is the large eat-in kitchen with ample space for gathering, complemented by a separate formal dining room and an expansive family room featuring a cozy wood-burning fireplace. Major updates include a new roof installed in 2020, offering peace of mind for years to come. Conveniently located in a USDA-approved area, this home also qualifies for 100% financing eligibility for qualified buyers. If you’ve been searching for spacious living paired with a sought-after water lifestyle, this Cedarhurst gem checks all the boxes.

1217 Pine Ave, Shady Side

Listing courtesy of RE/MAX One. Contact:

$3,500,000

5 Beds ⋅ 6 Baths

Silver Water is a rare west-facing waterfront home designed in direct response to the Chesapeake—offering broad water views, remarkable sunsets, and a level of architectural clarity seldom found in the area. Set behind a private gate on a beautifully landscaped one-acre lot along the West River, the property combines seclusion with convenient access to Annapolis and Washington, DC. Spanning over 4,600 square feet, the home blends classic Chesapeake architecture with modern scale, light, and livability. High ceilings, oversized doors, and expansive windows draw the water into nearly every room, creating a constant connection to the horizon. The layout balances open, light-filled gathering spaces with a thoughtful separation of private areas, making it equally suited for everyday living and hosting guests. The main-level primary suite is positioned to capture water views, with a fireplace, spa-like bath, and custom walk-in closet. At the center of the home, the kitchen is designed for both daily use and entertaining, anchored by professional-grade appliances and clean, functional design. Outdoor living is fully realized. A waterside saltwater pool, bluestone terraces, teak decking, and a fully equipped pool house create a seamless extension of the home—designed for both relaxed days and larger gatherings. The lawn stretches to a protected shoreline, reinforcing the home’s connection to the water. A private 70-foot pier with lift provides immediate access to the Chesapeake, ideal for day boating and spontaneous time on the water, with nearby marinas accommodating larger vessels. Additional features include mature landscaping, a smart irrigation system, multiple outdoor living areas, a detached three-car garage, and a separate storage structure. Silver Water offers a rare combination of design, setting, and livability—an intentional waterfront home where architecture and landscape come fully into alignment.

4750 Frederick Ave, Shady Side

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$100,000

Sub-division potential for this undeveloped, 1 acre lot! May be able to reconfigure to 2 separate lots. 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, 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!

Haile Parkway, Shady Side

Listing courtesy of Samson Properties. Contact:

$100,000

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, 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— start planning your future in Shady Side, MD!

1445 & 1447 Haile Pkwy, Shady Side

Listing courtesy of Samson Properties. Contact:

$399,900

Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub and shower combination. The bright kitchen shines with white cabinetry and brand new, never used stainless steel appliances, giving it a clean, fresh feel. The living room opens to the fenced backyard and patio through a sliding glass door, inviting easy indoor and outdoor living. Just one step down from the living room is a private office with double doors, its own half bath, and access to the laundry and utility room, offering flexible space for working from home, hobbies, or guests. Outside, the circular driveway provides generous parking, and the backyard shed adds convenient storage for beach chairs, bikes, and lawn equipment. BOAT SLIPS AVAILABLE

1199 Oak Ave, Shady Side

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

$669,500

4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunity goes with this home on .57 acres of C1B commercial zoned property. Additional .375 acres and .1243 acres of MC heavy commercial zoned property for a totaling 1.0693 Acres, with 135 feet of bulkheaded waterfront, 200-foot pier, with approximately 12 boat slips. Water depth from 4 to 8 feet that can accommodate 40ft+ boats. Total income for 2025 was $6900. with only a few slips rented. Will require a commercial lender or cash to purchase.

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$699,900