Shady Side MD Homes for Sale

Shady Side MD Homes for Sale

$995,000
3 Beds 2 Baths
Exceptional value for this exquisite, recently renovated coastal waterfront retreat, offering the perfect blend of luxury, comfort, and breathtaking water views throughout. The home features three generously sized bedrooms, including a convenient main-level primary bedroom, and two elegantly appointed bathrooms. The bright, open floor plan is enhanced by vaulted ceilings, recessed lighting, solar-powered skylights with built-in remote-controlled shades, and beautifully refinished oak hardwood flooring throughout the main level. Recent improvements include a new architectural-shingle roof, new upper-level carpeting in both bedrooms, new water treatment system, and professionally and tastefully painted inside and out. At the heart of the home, the gourmet kitchen features solid wood white cabinetry, updated appliances, new quartz countertops, a huge center island with cooktop, prep sink, ample seating, and a spacious eat-in area—ideal for the culinary enthusiast as well as for everyday living and entertaining. The inviting great room, complete with a cozy gas fireplace, is the perfect place to relax and unwind and take in the wonderful views. Step outside to a beautifully landscaped, level 0.24-acre lot and enjoy your own private L-shaped pier with resurfaced decking, multiple slips, and a boat lift. A new bulkhead adds even more value to this exceptional property situated on South Creek, just off the West River and Chesapeake Bay—perfect for boating, crabbing, fishing, and enjoying life on the water. Take in the expansive views from the multi-level decks and adjoining screened-in area, creating an outstanding setting for relaxing and entertaining. An oversized one-car garage provides additional storage, while the newly paved driveway offers off-street parking for six or more vehicles. Community amenities are complete with a swimming beach, dock, picnic area, and playground. Come experience the sought-after lifestyle of South County waterfront living—your dream coastal oasis awaits!

4958 Lerch Dr, Shady Side

Listing courtesy of Beam Realty Group, Inc.. Contact: 4438656969

$750,000
3 Beds 3 Baths
**OPEN HOUSE SAT 7/25 11am-1pm**New roof & gutters installed last week! 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. 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. 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: 4105356291

$495,000
4 Beds 3 Baths
Multi Offer Scenario. Please submit final and best offer by 12:00 noon Monday, July 13th. Set on a large double corner lot in the waterfront community of Cedarhurst, this four-bedroom, three full bath Cape Cod offers a flexible layout and thoughtful updates throughout in a setting where everyday can feel like a vacation. Just down the street from the water, the home blends relaxed coastal living with resort-style community amenities along the Chesapeake Bay in Shady Side. An open floor plan defines the main level, where vaulted ceilings connect the living room, dining area, and kitchen. Hardwood flooring runs through much of the home, while the living room is wrapped in windows and centered by a cozy gas fireplace. The kitchen features bright white cabinetry, granite countertops, a central island, and stainless steel appliances. A main-level primary bedroom provides convenience and includes an en-suite bath with beadboard trim and a double sink vanity. Two additional bedrooms and a full hall bath complete this level, along with a dedicated laundry room. Upstairs, the current owners have created a second primary suite option. This space includes a luxurious en-suite bath with a floor-to-ceiling tiled shower featuring a river rock floor and frameless glass door, along with a modern freestanding soaking tub. A walk-in closet with built-ins adds function and storage. The upper level also includes a landing area and two utility rooms, one of which features a recently added water softener system. Outdoor living is enhanced by a deck just off the living room overlooking the side yards, along with a storage shed for additional space. The interior has also been freshly painted by the current owners, giving the home a clean and updated feel. Cedarhurst on the Bay is a true waterfront community on the western shore of the Chesapeake Bay, offering residents access to a community harbor with over 60 boat slips, a boat ramp, fishing and crabbing pier, sandy beach, and expansive waterfront common areas. Additional amenities include picnic areas, playgrounds, green space, and a community house used for neighborhood events. Marina services accommodate both power and sailboats, with slips available for reservation. Residents enjoy boating, kayaking, swimming, and wide-open Chesapeake Bay views just moments from home.

5222 Spring Ave, Shady Side

Listing courtesy of Northrop Realty. Contact: 4107702910

$795,000
3 Beds 2 Baths
Waterfront living with a private dock—all for under $800,000! 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 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 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:

$650,000
4 Beds 4 Baths
There aren't many opportunities left to build brand new in Anne Arundel County at this price point, and 1430 Haile Parkway is one of them. Haile Parkway is quiet, wooded, and tucked into the laid-back charm of Shady Side, close enough to everything you need, far enough away to actually exhale. New construction at this level of quality and finish from one of the area's most respected builders is a rare find, and the price makes it even more compelling. Whitehall backs every home with a fixed-price contract, weekly progress reports, and a 5-year structural warranty, the kind of transparency that makes the building process smooth and confidence-inspiring. Construction-to-permanent or cash financing required; 100% VA financing options available for those who qualify. Whitehall Building & Company's Chessie plan is a thoughtfully designed three-level home offering over 3,000 square feet that lives larger than it looks. The main level centers around a generous family room with fireplace, a well-proportioned kitchen with pantry, dining area, and a dedicated office, the kind of layout that feels spacious and connected. A covered porch off the main level brings the peaceful, wooded setting into the daily experience. Upstairs, the primary suite is a true retreat, complete with a private bath and walk-in closet. Two additional bedrooms, a shared full bath, and upper level laundry round out the second floor. The lower level includes a bedroom and full bath, ideal for guests or added flexibility, along with a two-car garage and entry foyer.

1430 Haile Pkwy, Shady Side

Listing courtesy of Hubble Bisbee Christie's International Real Estate. Contact:

$745,000
3 Beds 2 Baths
Fantastic opportunity to own your own land lighthouse-inspired round house with water views! Perfect serene retreat for the commuter and/or investment opportunity. Quiet neighborhood, blue heron sightings, and all the advantages of coastal living without the summer beach traffic. Freshly painted! This unique home features 3 bedrooms, 2 full bathrooms, an open-concept layout, and a spacious family room off the kitchen with no closed-off spaces — ideal for entertaining. Deltec home, designed with durability and efficiency in mind. Deltec homes are known for their strength, energy efficiency, and resistance to high winds and severe weather. Large windows surround the home, filling the interior with natural light and enhancing the panoramic water views. Wood floors flow throughout, adding warmth and character. Step outside to the wraparound deck, perfect for relaxing and taking in the dreamy scenery. Additional quality exterior upgrades include durable Hardi-plank siding and architectural roof shingles, both known for their superior longevity, performance, and curb appeal. Situated on a peninsula tucked between the Chesapeake Bay and 500 acres of state park, this property is currently enjoyed as a charming second-home retreat and part-time Airbnb. Come experience this one-of-a-kind home and incredible setting! Gated community offers a boat ramp, 2 private piers for fishing, crabbing, and boating, and a walking trail along the Bay.

5341 Al Jones Dr, Shady Side

Listing courtesy of Redfin Corp. 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: 4433727171

$479,990
3 Beds 3 Baths
Would you love to live in a water oriented community? Have you ever? Come take a look at this year 2020 built 3 bedroom 2.5 bathroom home located in the AVALON SHORES community surrounded by the beautiful Chesapeake Bay and tributaries. Avalon Shores has wonderful neighborhood amenities including play areas, beach and boat launch . Come see this traditional home with an open floor plan. Plenty of wonderful sunlight on a beautiful light oak laminate floor, will provide the warmth and homey feeling you look forward to coming home to. Plenty of bathroom space to share and a very large open kitchen/dining/living combination offers that openness in a home that you desire. Eateries along the waterfront, boating is a must! This home is a must see. Brand new carpet just installed, brand new kitchen cabinets with granite counter tops, freshly painted through out. Fully fenced in yard with high quality white vinyl fencing. Extra parking pad able to handle 3 or 4 cars or maybe your camper. Large driveway!! Built in 2020 so you don't have to worry! Community dock, community boat ramp, community playgrounds for the kids!! Conveniently located to DC, Annapolis, and Andrews AFB. No HOA, Not in the flood zone so no flood insurance. This move-in ready home combines style, functionality, and comfort-don't miss the opportunity to make it yours! Welcome to Avalon Shores, a sought-after water-privileged community along the Chesapeake Bay!

1222 Juniper St, Shady Side

Listing courtesy of HomeSmart. Contact: 3013524065

$649,990
4 Beds 3 Baths
6/26/26. Home is under roof ready for drywall. August delivery. 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 time to personalize your selections so you can create a home that perfectly reflects your style. 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 quartz 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. $5,000 closing assistance with preferred lender & Title company. Actual features, finishes, and layouts may vary.

5314 Al Jones Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$538,000
4 Beds 3 Baths
Price reduction! This thoughtfully designed and 2022-built home blends modern finishes with a tranquil setting set against a backdrop of mature woods, creating a bright, open, and inviting space for both everyday living and entertaining. An open two-story foyer welcomes you inside to the main living area with vaulted ceilings, while 9' ceilings throughout the rest of the home enhance the airy, open feel. Charming cottage-style windows fill the space with natural light, and LVP flooring flows seamlessly through the living room, kitchen, and wide hallway to the bedrooms. The kitchen features oil rubbed bronze fixtures, soft-close cabinets, granite countertops, and a center island with overhang for stools, plus space for a dining table. There is also potential for a deck off the back of the home, perfect for outdoor living. The main level includes two secondary bedrooms and a spacious owner’s suite. The secondary bedrooms feature custom molding, decorative wall trims, and stylish paint finishes—one accented with decorative peelable wallpaper—and share a hall bath with granite vanity and shower/tub combo. Enjoy views of the wooded landscape from the owner’s suite, complete with two closets and a distinctive en-suite bath featuring dual sinks, granite countertops, a walk-in shower, custom wall trim accents, and removable wall covering. The lower level provides a versatile living space, including a spacious recreation room with sliding glass doors to the backyard, a flexible 4th bedroom ideal for guests or an in-home office, and an additional full bath with granite vanity and shower/tub combo. Raised garden beds just outside in the backyard and alongside the home are ideal for growing vegetables and flowers.

1411 Haile Pkwy, Shady Side

Listing courtesy of Redfin Corp. Contact: 4102028454

$349,870
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:

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