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4819 Avery Rd, Shady Side
$2,000,000
5 Beds ⋅ 5 Baths
Welcome to a truly remarkable waterfront retreat where timeless design meets resort-style living. Set along the shores of Hopkins Cove with sweeping views of the West River, this residence offers over 150 feet of water frontage and a private pier stretching nearly 270 feet, complete with boat lift and covered pavilion—everything you need to embrace life on the water. This five-bedroom, four-and-a-half-bathroom home is designed for both relaxation and entertaining. The indoor and outdoor living spaces flow seamlessly, with a backyard that feels like a private resort. Manicured gardens, a custom outdoor kitchen, and an inviting pool with hot tub create the perfect setting for gatherings large or small. From morning coffee as the sun rises to evenings spent watching the sky glow at sunset, every day here feels like a getaway. Inside, the attention to detail is immediately apparent. A dramatic two-story foyer sets the stage with custom double doors, wrought iron railings, and striking stonework that bring warmth and sophistication. The chef’s kitchen, appointed with top-tier Viking appliances, is both functional and inspiring, while the living room’s fireplace provides a cozy vantage point to take in views of the pool and river. The primary suite is a sanctuary of its own, offering a spacious retreat with a spa-like bath that rivals any five-star hotel. Additional bedrooms and baths provide comfort for family and guests, while custom finishes in stone, wood, and ironwork continue throughout the home, creating an atmosphere that is both refined and welcoming. This is more than a home—it’s a lifestyle. Whether entertaining by the pool, setting out from your private pier, or simply enjoying the quiet beauty of Hopkins Cove, every detail has been designed to elevate daily living. Experience the very best of waterfront living and make this extraordinary property your own.

4819 Avery Rd, Shady Side

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

Selling Office: Arlington Realty, Inc..

1100 Steamboat Rd, Shady Side
$1,950,000
4 Beds ⋅ 3 Baths
Spectacular West River waterfront! A serene lot with panoramic water views, a custom-built home that exudes coastal style, a private dock with two boat slips, a detached 3-car garage with a storage loft, a spacious yard for playing and entertaining, an exquisite vantage point for enjoying the area’s natural beauty, from waterfowl to sunsets. Welcome to 1100 Steamboat Road, offering the best of Chesapeake Bay living on the picturesque West River in Shady Side, MD. Privately sited at the end of Steamboat Road on a gated 0.5-acre lot, this superb property boasts approximately 133 feet of water frontage with expansive, 180-degree views of the West River. The 300-foot private dock features an ideal configuration for both sailors and powerboaters: a rare, deep-water boat slip with mean low water depth of approximately 7 feet, and a second slip with mean low water depth of approximately 3.5 feet, also equipped with a 20,000-lb motorized lift. The dock provides easy access to the channel in the river and the Bay beyond and is outfitted with electricity, water, two dock boxes, and a floating dock to accommodate dinghies, kayaks, SUPs, or other small watercraft. A dream come true for those looking to embrace the waterfront lifestyle! The meticulously-maintained 4-bedroom, 2.5-bath home was expertly designed to enhance the setting. Most living spaces enjoy sweeping, unobstructed water views. Among the many highlights are a main level with an airy, easy-flow layout great for entertaining, a gourmet eat-in kitchen, an attractive elevator for convenient access between floors, a main-level bedroom (currently configured as an office), a masonry chimney and gas fireplace, and a deck with gas fire pit - a favorite spot for savoring the sunsets year-round. The second level includes a primary suite with two walk-in closets and a spa-like bath with separate WC, a family room with prime views and a private balcony, plus two additional generously-sized bedrooms sharing a hall bath. Two staircases allow for privacy between the primary suite and guest spaces. The detached garage provides covered parking for 3 vehicles plus a substantial upper-level storage space with great potential: consider converting it to a bunk room, teen hangout, separate work studio, or other creative use. The home is equipped with three zones of HVAC and a whole-house backup generator, and the well-tended yard includes an irrigation system for lawn and landscaping. This special property also holds a place in local history: from the late 1800s to early 1900s, the steamboat “Emma Giles” docked here on a regular route from Baltimore to points on the Bay (hence the name Steamboat Road). Today, it’s ready for your enjoyment as a weekend retreat or full-time residence, conveniently located less than 40 miles from downtown DC, approximately 20 miles from Annapolis, and less than 40 miles from BWI Airport. A must-see! Agent related to owners. Square footage estimated per recent floor plan drawing; all measurements approximate.

1100 Steamboat Rd, Shady Side

Listing courtesy of Compass. Contact:

Selling Office: Unrepresented Buyer Office.

1457 Nieman Rd, Shady Side
$1,500,000
5 Beds ⋅ 4 Baths
Stunning waterfront retreat nestled along the serene shores of the Chesapeake Bay, located in the charming community of Shady Side, Maryland. Perfectly situated on Parish Creek, this spacious, move-in ready home offers a unique combination of comfort, privacy, and coastal living. The open-concept floor plan on the main level features a gourmet kitchen with sleek quartz countertops and island, a cozy breakfast area, and a generously sized great room. A dining room/office and sitting room provide versatile spaces for both relaxation and work, complemented by a full bath for added convenience. Upstairs, the tranquil waterfront primary bedroom offers a peaceful sanctuary with an ensuite bathroom and two walk-in closets. Three additional bedrooms, one full bathroom, and laundry room complete the upper level. Just steps from the water, a 20' x 20' screened cabana creates an ideal space for dining, reading, or simply enjoying the beautiful views. The detached three-car garage adds exceptional value with a fully-equipped one-bedroom, one-bath apartment above, offering the perfect space for guests or additional living needs. For boating enthusiasts, the private 100-foot pier is a true highlight, featuring a 30-foot floating dock with a 12,500lb lift, two jet-ski lifts, electrical and plumbing connections, and a water depth of 4' MLW, ensuring ample space for all your water activities. Additional amenities include a full irrigation system, horseshoe pits for outdoor entertainment, smart home switches, and a connection to public sewer. Ideally located just 30 minutes from Annapolis and less than an hour from Washington, D.C., Shady Side offers a peaceful waterfront lifestyle with marinas, quiet beaches, and a strong sense of community. Whether you’re seeking a weekend getaway or a permanent residence, this is your chance to own a piece of Chesapeake Bay paradise.

1457 Nieman Rd, Shady Side

Listing courtesy of Washington Fine Properties, LLC. Contact:

Selling Office: In-Vision Realty.

1268 Hayes Rd, Shady Side
$1,099,000
3 Beds ⋅ 2 Baths
Discover your dream lifestyle in this exceptional 3 bedroom 2 full bath waterfront property located at 1268 Hayes Road in the charming community of Shady Side, MD. combining the peacefulness of a secluded setting with essential modern amenities. As you step inside you'll notice the sun drenched open floor plan complete with a large cooks kitchen featuring a huge center island, cozy breakfast nook and walk-in pantry. The adjacent dining room is perfect for large holiday gatherings and flows seamlessly into a comfortable family room. A gorgeous living room with waterfront views divides 2 ample sized bedrooms for privacy and relaxation. Enjoy sweeping views of your very own cove or dine al fresco in the fully screened in porch. Upper level features the 3rd bedroom offering a private home office, abundant built-in drawers and shelving plus an elevated deck for morning coffee. The half acre lot is brimming with seasonal plantings, lush lawn, a two car garage and your very own dock. This is the perfect setting for those who love boating, fishing, or simply enjoying spectacular water views and stunning sunrises. Don't miss the opportunity to create your own waterfront haven just in time for summer! Recently renovated to include 2 brand new bathrooms, interior flooring, screened in porch, and much more! See upgrades sheet for full list of upgrades. If you are interested in learning more about this remarkable waterfront property, reach out to the exclusive listing broker Casey A. Sutherland with Maryland Waterfront Properties.

1268 Hayes Rd, Shady Side

Listing courtesy of Maryland Waterfront Properties LLC. Contact:

Selling Office: Keller Williams Gateway LLC.

1379 Mcdonald Rd, Shady Side
$835,000
4 Beds ⋅ 3 Baths
***BRAND NEW & READY FOR IMMEDIATE OCCUPANCY*** this stunning Arts & Crafts home by Laine Street Homes blends timeless design with modern luxury. Set on a premium 2.3 acre homesite surrounded by mature woodlands, this 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 eat-in kitchen impresses with premium quartz countertops, herringbone tile backsplash, tasteful high end 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 offers seasonal water views, luxury vinyl plank flooring, a walk-in closet, and a spa-inspired ensuite bath with a 7x6 walk-in shower boasting dual shower heads and floor-to-ceiling tile. Additional highlights include 7-inch LVP flooring throughout the main level, shake siding with stone column bases, public sewer, 2x6 construction, Pella windows, ceramic tile in all baths and laundry, high efficiency tankless water heater, 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.

1379 Mcdonald Rd, Shady Side

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

Selling Office: Compass.

1340 E West Shady, Shady Side
$795,000
3 Beds ⋅ 3 Baths
***BRAND NEW CONSTRUCTION READY FOR IMMEDIATE OCCUPANCY*** this Modern Farmhouse by local builder Laine Street Homes blends timeless architecture with modern luxury. Spanning over 2,200 finished square feet, the beautiful property features a MAIN LEVEL OWNER'S SUITE and boasts high-end appointments throughout. From the wraparound front porch, step into the open-concept main level that includes a spacious family room with gas fireplace, a formal office with cathedral ceiling, a morning room nook, dining area, and a convenient half bath. The gourmet kitchen is a true showpiece, featuring a large center island with breakfast bar, soft-close timber and dove cabinetry, open apron farmhouse sink, quartz countertops, subway tile backsplash, and a five-piece stainless steel appliance package including a wall oven, cooktop, and range hood. The main-level owner's suite offers a walk-in closet and a luxury en-suite bath with dual vanities and an expansive 7x6 spa shower with dual shower heads. Upstairs, you will find two additional bedrooms and a second full bath. Additional highlights include LVP flooring throughout the main level, ceramic tile in all baths and the laundry room, public sewer, Pella windows, high efficiency tankless water heater, 30-year architectural shingles, a 92% efficient Carrier HVAC system, air seal package, 2x6 framing, R49 ceiling insulation, R21 wall insulation. 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.

1340 E West Shady, Shady Side

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

Selling Office: Compass.

6440 W Shady, Shady Side
$600,000
4 Beds ⋅ 3 Baths
Another quality built New Construction Home by Jim Robinson/Real Estate General, LLC in the highly desired Shady Side Community. Ready to Move In! 4 bedrooms, 2.5 bathrooms, with a side entry 2 car garage on a large private .45 acre level lot. This beautiful home is filled with natural light and features an open floor plan on the main level with wide-plank LVP flooring, 9 foot ceilings, detailed trim work including crown molding, chair railing, wainscoting, and oversized baseboard, stunning kitchen with quartz countertops, designer white cabinets, and stainless steel appliances, and a propane fireplace in the Family Room framed by stylish shiplap. The upper level has a luxurious primary suite with a walk in closet featuring built-ins and a spa-like bathroom with a double vanity and a glass-enclosed tile shower. There are three additional bedrooms, another full bathroom and a laundry room on the second floor. Spacious asphalt driveway and an additional driveway area with pavers allow for the parking of multiple vehicles. Property is close to several marinas and is just up the street from Shady Side Park which has a playground, tennis/pickleball courts, basketball courts, baseball fields and a kayak launch area for access to the water. Property is near major roads with an easy commute to Washington, D.C., Annapolis and Baltimore. Enjoy the vacation lifestyle of this Southern Anne Arundel County Community!

6440 W Shady, Shady Side

Listing courtesy of J. J. Rogers Real Estate. Contact:

Selling Office: EXP Realty, LLC.

5218 Nick Rd, Shady Side
$400,000
3 Beds ⋅ 2 Baths
Welcome to a home that feels as good as it looks. This fully renovated 3-bedroom, 2-bath residence offers the charm and comfort of coastal living with no HOA. From the moment you walk in, the open floor plan space feels inviting, thoughtfully laid out, easy to live in, and designed to make everyday life feel a little more relaxed. The primary suite had an extension done, creating a spacious and private retreat complete with its own full bathroom. The home is functional and inviting, making smart use of every square foot without sacrificing comfort. Behind the warmth and style is the kind of work that truly matters. Every major system has been replaced, including brand-new electrical, plumbing, and HVAC. The home also features a new roof, siding, windows, and a well water filtration system. All renovations have been county approved and fully inspected — offering the kind of long-term peace of mind today’s buyers value. Engineered hardwood flooring runs throughout the hallways and bedrooms, adding continuity and warmth. The kitchen sits at the heart of the home, featuring stainless steel appliances, granite countertops, soft-close shaker cabinetry, a double sink, and a center island with bar seating — ideal for morning coffee, casual dinners, or gathering with friends. A tucked-away pantry with pocket door access keeps storage practical and discreet. Outside, the property is EV-ready with a 240V outlet already installed for an electric vehicle charging station. With convenient access to Route 2, Route 214, and Route 50, you’re approximately 25 minutes from Annapolis and under an hour to Washington, D.C., while still enjoying the slower pace and charm of the Shady Side community. This is more than a renovation, it’s a move-in ready home designed for comfort, connection, and peace of mind. Schedule your showing and experience it for yourself.

5218 Nick Rd, Shady Side

Listing courtesy of Samson Properties. Contact:

Selling Office: Bennett Realty Solutions.

5649 Shady, Churchton
$385,000
3 Beds ⋅ 1 Baths
Own this home with no down payment required. This property qualifies for USDA and FHA solar+ financing which provides for up to 5% of downpayment & closing cost assistance with a market interest rate, making homeownership attainable. This well-maintained home is located in an area eligible for a 100% USDA Zero-Downpayment Loan, providing a chance to buy a move-in ready home without the financial burden of a down payment. The home features a bright, open layout on a single level, designed for easy living. Positioned in the center of Churchton, this 3-bedroom coastal rambler includes a combined kitchen and dining area, spacious bedrooms, central air conditioning, public sewer, and a sizable third of an acre backyard well suited for summer gatherings. The property has been well cared for, allowing for immediate occupancy without significant renovations. Enjoy a tranquil, water-oriented lifestyle, just 1 to 2 miles from two popular waterfront locations: Franklin Point State Park, which offers over 470 acres of protected marsh, hiking trails, and wildlife viewing along the West River and Chesapeake Bay, and Jack Creek Park, which features walking trails, a secluded beach, and a launch site for kayaking, canoeing, and paddleboarding. Spend weekends enjoying boating, crabbing, or fishing, with convenient public boat launches, local marinas, and waterfront dining nearby. Experience the tranquility of a close-knit coastal community while still having an easy commute to Joint Base Andrews, the Annapolis waterfront, and the Washington Beltway, all without the hassle of an HOA.

5649 Shady, Churchton

Listing courtesy of Taylor Properties. Contact:

Selling Office: Engel & Volkers Annapolis.

6070 Shady, Shady Side
$290,000
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.

1451 Shady Rest Rd, Shady Side
$107,000
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.