Oyster Harbor Homes for Sale

Oyster Harbor Homes for Sale

Welcome to Oyster Harbor, an exquisite subdivision nestled in the heart of Annapolis, Maryland, within the scenic Anne Arundel County. Known for its stunning waterfront views and serene surroundings, Oyster Harbor offers a unique blend of coastal charm and suburban comfort, making it an ideal place to call home.

As you stroll through the beautifully landscaped streets, you’ll discover a vibrant community that is both welcoming and engaging. The neighborhood features a variety of homes for sale, each showcasing distinct architectural styles and modern amenities. Whether you’re looking for a cozy single-family home or a spacious waterfront property, Oyster Harbor has something to suit every lifestyle and budget.

Living in Oyster Harbor means enjoying the best of Maryland’s natural beauty. The subdivision is conveniently located near the Chesapeake Bay, providing residents with easy access to boating, fishing, and a plethora of outdoor activities. Imagine spending weekends sailing on the bay or enjoying a leisurely picnic at one of the nearby parks.

Additionally, the community is just a short drive from Annapolis’ historic downtown area, where you can explore charming shops, dine at exquisite restaurants, and immerse yourself in the rich maritime heritage of the city.

With homes for sale in this picturesque subdivision, now is the perfect time to discover what Oyster Harbor has to offer. Experience the tranquility of waterfront living while being just moments away from the vibrant culture of Annapolis. Come and find your dream home in Oyster Harbor today!

Newest Oyster Harbor Homes for Sale

$675,000
3 Beds ⋅ 3 Baths ⋅ MDAA2156688 MLS
AN EXCEPTIONAL OPPORTUNITY TO ASSUME THE EXISTING 4.75% Discover the charm and flexibility of the 3 - bedroom, 2.5 bath Coastal haven in Oyster Harbor, one of Annapolis most desirable water - privileged communities. AnThoughtfully designed for comfortable everyday living and the Chesapeake Bay lifestyle, the home offers inviting indoor spaces, outdoor entertaining areas, and access to exceptional community amentiies. Fresh updates - including interior paint make the home feel refreshed and ready to enjoy. On first level two bedrooms with adjoining Jack and Jill bathroom plus 1/2 bath and laundry room. Handsome hardwoods add warmth and character throughout the main living areas. A Wood burning fireplace creates a cozy focal point for cool evenings and relaxed gatherings. A large pantry provides valuable kitchen storage and everyday convenience. The spacious primary suite includes a private ensuite bath and an upper-level deck, offering a peaceful place to enjoy morning coffee or unwind outdoors. The second floor flex space can serve as a home office, sitting room, dressing area, nursery, or an opportunity to enlarge the primary bath. A screened porch extends the living space outdoors - ideal for dining, entertaining, or enjoying the quite surroundings. The fenced backyard offers privacy and room for pets, play, gardening, or outdoor entertaining. A dedicated grilling station makes hosting summer cookouts easy. The spacious garage includes a workshop area plus attic storage, with room for tools, bikes, paddle boards, boating gear, outdoor equipment, and Chesapeake Lifestyle essentials. Security system. Life here extends beyond the property lines. Oyster Harbor is a water- privileged community with access to a community marina, kayak rack, and beach, both a short stroll from the home. Enjoy boating, kayaking, fishing, swimming, or simple taking in the waterfront atmosphere without giving up the convenience of being minutes from downtown Historic Annapois. The community amenities are included through Oyster Harbor's tax district, helping make the neighborhood's recreational features part of the homeownership experience. Va Assumable loan @ 4.75% may be available. This home is more coastal charm - it is an opportunity to embrace the casual, connected, water oriented lifestyle of Annapolis

1339 Fishing Creek Rd, Annapolis
$975,000
4 Beds ⋅ 4 Baths ⋅ MDAA2157478 MLS
Experience resort like living in the water-oriented community of Oyster Harbor! Why choose between elegance and Chesapeake living when you can have both?! This stunning property offers the perfect blend of style and comfort with the ease of access to a plethora of sought after water-oriented community amenities! The main level features a beautiful, open kitchen with walk-in pantry, stainless steel appliances, center island, and large eat-in space. The living room is truly the heart of the home featuring a cozy gas/propane fireplace- perfect for gathering for cozy evenings at home. The upper floor is home to all four bedrooms- two of which have attached bathrooms and walk-in closets- and the upper level laundry adds convenience to daily living. The attached garage, with space for two vehicles and additional storage, provides practicality without compromising on style with a large driveway making it easy for guest parking. One of the standout features of this property is the spacious deck and large backyard- indoor/ outdoor living at its finest! The community of Oyster Harbor offers an exclusive lifestyle for water enthusiasts, with opportunities for boating, fishing, and enjoying the natural beauty of the bay. Enjoy easy access to many community amenities including: a large beach with gazebo, two tot lots (one on the beach!), three community marinas, boat ramp, fishing pier, kayak storage, and more! This home is not just a residence; it's a gateway to a lifestyle of luxury and leisure. Experience the perfect blend of modern amenities and serene surroundings in this exceptional Oyster Harbor property.

1326 Harbor Rd, Annapolis
$974,990
4 Beds ⋅ 3 Baths ⋅ MDAA2157360 MLS
Construction is underway — and something truly special is taking shape! Schaefer Homes is proud to present this stunning newly constructed Colonial in the prestigious Oyster Harbor community, with a target completion date of November 2026. From the moment construction began, every detail has been thoughtfully considered to deliver a home that is as beautiful as it is livable. Set on a sprawling 0.62-acre lot, this exceptional residence offers the kind of space and privacy that is increasingly rare — plenty of room to create the outdoor oasis you've always envisioned, whether that's a garden retreat, entertaining terrace, or simply wide open space to enjoy the beauty of your surroundings. Inside, the elegant Colonial layout unfolds beautifully across a thoughtfully designed floor plan featuring 4 spacious bedrooms and 2.5 elegantly appointed bathrooms. The showstopping gourmet kitchen is the heart of the home, outfitted with upgraded design features and premium finishes that will inspire everything from weeknight dinners to unforgettable gatherings with family and friends. From its classic vinyl siding exterior to its sophisticated interior appointments, this home strikes the perfect balance between timeless architectural charm and the fresh, modern feel of new construction. Every finish, every detail, and every design choice reflects the quality and craftsmanship that Schaefer Homes is known for throughout Maryland. Oyster Harbor is more than a community — it's a lifestyle. Serene, exclusive, and truly one of a kind, this is the kind of neighborhood where neighbors become friends and every day feels like a retreat. This is your opportunity to plant roots in one of the area's most sought-after addresses. Don't wait — opportunities like this don't come around often. Schedule your private appointment today and take the first step toward making this dream home yours!

3268 Kitty Duvall Dr, Annapolis
$1,285,000
4 Beds ⋅ 3 Baths ⋅ MDAA2153954 MLS
Discover elegance at 1227 Cross Road in Annapolis, Maryland, a stunning 2023-built home in the water-privileged Oyster Harbor community, elevated by upgrades made by the current owner since purchase. Enter through grand double doors into an open foyer with hickory hardwood floors, soaring ceilings, and crown molding. The great room impresses with a coffered ceiling, ceiling fan, fireplace, and large windows that flood the space with natural light. The gourmet kitchen is an entertainer’s dream, featuring a 5-foot quartz island, double oven, prep sink, breakfast nook, expansive walk-in pantry, and a butler’s pantry/wet bar upgraded by the owner for effortless hosting. The formal dining room, with its trey ceiling and designer windows, adds sophistication. A main-level office or in-law suite includes a full bath, ceiling fan, and custom California Closets added post-purchase for enhanced organization. Ascend the stunning, light-filled staircase, a true architectural centerpiece to the second floor. Here, a versatile loft/flex space is perfect for a family room, home office, or play area. Two additional bedrooms with ceiling fans and owner-installed California Closet systems offer comfort, with one boasting private bath access and a walk-in closet. The primary suite is a retreat, featuring recessed lighting, a trey ceiling, a spacious dressing/sitting area, a luxurious 6x6 shower, and a large walk-in closet with a California Closet upgrade. A laundry center, enhanced by the owner with custom cabinetry, granite countertops, and a Blanco sink, adds convenience. The oversized 2-car garage features 12-foot ceilings, an owner-applied epoxy floor, and a 240V electric vehicle hookup. A mudroom with custom storage cabinetry, added post-purchase, welcomes you from the garage. Additional owner upgrades include gutter guards, Cat6 wiring, pre-installed security system wiring, and a 1,500 sq ft conditioned crawl space for storage. Outdoors, relax on the 13x10 screened porch with recessed lighting, a thoughtful owner addition. Recent updates include kitchen backsplash subway tile, wet bar backsplash subway tile, fireplace surround and painting throughout. Enjoy Oyster Harbor’s waterfront amenities, including a boat ramp, pier, private beach, and opportunities for kayaking, fishing, and paddleboarding. With the current owner’s thoughtful upgrades since 2023, this Annapolis gem combines modern luxury with unparalleled functionality. View the full HD Video Tour and contact listing agent for a private in person tour.

1227 Cross Rd, Annapolis
$750,000
5 Beds ⋅ 5 Baths ⋅ MDAA2152934 MLS
2.625% Assumable FHA loan! Significant Price Improvement! Priced to sell, incredible value and opportunity. Excellent Condition. Welcome to this beautifully maintained custom built Tudor Style home in this small coastal community. NO HOA!! Pride of ownership shows! With a primary suite on the main level and another primary suite on the upper level, this home is perfect for Multi-Generational Living and Accessibility! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 large bedroom with a full bath and walk-in shower; and the lower level has another full bath and several areas to make additional bedrooms. The huge 1,100 sqft finished lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area; plus a family room or theatre room and private entrance! There is even space for a kitchenette! There are so many possibilities with this extra space including an apartment or in-law suite! The home is filled with natural light and scenic views throughout. Situated on almost a half of acre and only 2 blocks to the Chesapeake Bay! The lush backyard is fully fenced in and ready for entertaining and evening dinners on the updated trex deck! The lot next to the home is a county preserved wooded lot that offers privacy and attracts wildlife. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. The home has been well cared for and maintained; only two owners since it was built! Recent updates include: HVAC, water heater, main level LVP floors that are very durable, trex deck and renovated front porch with tile, custom plantation shutters, renovated primary suite and luxury full bath, front load w/d, professionally cleaned, professionally landscaped, backyard drainage system...and more! Sellers are MOTIVATED and ready for another family to make this their home! MOVE-IN READY AND A MUST-SEE! You won't find many homes with this lot size and location for this price. Don't miss this great opportunity! Schedule your showing today.

3280 Arundel On The Bay Rd, Annapolis
$530,000
3 Beds ⋅ 2 Baths ⋅ MDAA2145374 MLS
Stunning Oyster Harbor – Coastal Charm Meets Comfort This gorgeous property blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat ramp, and storage racks for kayaks and paddle boards, creating the ultimate waterfront lifestyle just minutes from downtown Annapolis. The home itself is designed for both entertaining and everyday enjoyment. An enormous screened-in porch and a spacious, fully fenced backyard provide plenty of room to garden, relax in a hammock, or host gatherings. After a day at the beach, the outdoor shower is the perfect convenience. Inside, the property features three bedrooms, two full bathrooms, and hardwood floors throughout the main level. Don’t miss the opportunity to live in this beautiful home and vibrant waterfront community—where comfort, charm, and lifestyle come together seamlessly.

1252 Creek Dr, Annapolis
$960,000
5 Beds ⋅ 5 Baths ⋅ MDAA2143700 MLS
Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up. Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint and favorable waterside placement offer strong potential to maximize views and overall design. Convenient access to the Chesapeake Bay and close proximity to Historic Downtown Annapolis by both land and water. Enjoy boating, sailing, and easy access to surrounding waterfront destinations throughout the region. Property is being sold strictly as-is. A unique opportunity for those ready to take on a full redevelopment project in a prime waterfront setting.

1254 Washington Dr, Annapolis
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