Oyster Harbor Real Estate

Oyster Harbor Real Estate

Welcome to Oyster Harbor, a picturesque subdivision nestled in the heart of Annapolis, Maryland. This charming community is a hidden gem within Anne Arundel County, offering a perfect blend of tranquility and accessibility. With its scenic waterfront views and lush, tree-lined streets, Oyster Harbor is not just a place to live; it’s a lifestyle.

Oyster Harbor boasts a diverse array of beautifully designed homes, each exuding character and warmth. From cozy single-family residences to modern townhouses, there’s something to suit every taste and family size. Residents enjoy spacious lots, meticulously landscaped gardens, and a strong sense of community that fosters lasting relationships among neighbors.

One of the standout features of Oyster Harbor is its proximity to the stunning Chesapeake Bay. Residents can enjoy leisurely strolls along the waterfront, partake in boating adventures, or simply relax while taking in breathtaking sunsets. The community is also conveniently located near a variety of parks, recreational facilities, and nature trails, making it an outdoor enthusiast’s paradise.

For those who appreciate the charm of city life, downtown Annapolis is just a short drive away. Here, you’ll find an eclectic mix of shops, restaurants, and cultural attractions. The vibrant local scene is perfect for families and individuals alike, offering everything from fine dining to casual eateries, art galleries, and historic sites.

With its welcoming atmosphere and prime location, Oyster Harbor is more than just a subdivision; it’s a place where cherished memories are made. Discover the beauty and community spirit of Oyster Harbor, and make it your new home today!

Newest Listings in Oyster Harbor

$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
$253,500
MDAA2153330 MLS
Rare opportunity to build your dream coastal retreat on this premium 50' x 200' lot in the highly sought-after waterfront community of Oyster Harbor! Instantly impressive, this beautifully manicured 0.23-acre parcel features a grand, half-moon driveway that offers elegant curb appeal and effortless pull-through access for vehicles or watercraft. This cleared and pristine canvas is ready for your custom build, with county sewer service available and suited for an individual well system. Nestled on a scenic peninsula between Oyster Creek and Fishing Creek, this exceptional location puts an unparalleled maritime lifestyle right at your doorstep. Boaters and outdoor enthusiasts will love the premier, resident-only privileges, including three private marinas, a community boat ramp, a fishing pier, and direct seasonal navigation to the Chesapeake Bay with views of the iconic Thomas Point Lighthouse. As a private special-taxing district, Oyster Harbor ensures beautifully maintained roads and a cohesive neighborhood environment. The exceptionally family-friendly neighborhood also boasts two community playgrounds—one at the sandy neighborhood beach and another on Harbor Road. Enjoy a peaceful, amenity-rich sanctuary just minutes from historic downtown Annapolis!

3354 Arundel On The Bay Rd, Annapolis
$750,000
5 Beds ⋅ 5 Baths ⋅ MDAA2152934 MLS
Significant Price Improvement! Priced to sell, incredible value. 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. OPEN HOUSE SATURDAY 9/12 1-3PM.

3280 Arundel On The Bay Rd, Annapolis
$649,900
4 Beds ⋅ 3 Baths ⋅ MDAA2150794 MLS
Experience the perfect blend of modern luxury and waterfront living at 1412 Ellis Road in the highly sought-after, water-privileged community of Oyster Harbor. This beautifully renovated home offers exceptional style, flexible living spaces, and outstanding indoor and outdoor entertaining—all just minutes from downtown Annapolis. The main residence features 3 spacious bedrooms and 2 full bathrooms, thoughtfully updated with today's finishes and designed for comfortable everyday living. The gourmet kitchen is the heart of the home, showcasing sleek cabinetry, premium appliances, and generous prep space, making it ideal for everything from casual family meals to hosting friends. A standout feature of this property is the detached studio suite, complete with its own kitchen, full bathroom, and washer and dryer. Perfect as a guest house, private home office, creative studio, or space for extended family. Does someone need a place to stay when visiting the Naval Academy. $$ This would work. The inviting living area offers a warm, welcoming atmosphere year-round. During the cooler months, relax in the cozy interior spaces, and when the weather warms up, step outside to enjoy two expansive rear decks that seamlessly extend your living space outdoors. Whether you're grilling, dining under the stars, or simply unwinding with family and friends, these outdoor spaces were designed to be enjoyed in every season Beyond the home, Oyster Harbor provides an exceptional Chesapeake Bay lifestyle with community amenities that include a private beach, boat ramp, fishing pier, kayak launch, playground, and picnic area. Here, you'll enjoy the charm of waterfront living while remaining just minutes from Historic Annapolis, shopping, restaurants, and major commuter routes.

1412 Ellis 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
$1,000,000
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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