Oyster Harbor Real Estate

Oyster Harbor Real Estate

Welcome to Oyster Harbor, a hidden gem nestled in the picturesque town of Ocean City, Maryland. This charming subdivision is a perfect blend of coastal tranquility and vibrant community living, making it an ideal choice for families, retirees, and anyone looking to embrace the serene lifestyle that Ocean City offers.

Oyster Harbor is renowned for its stunning waterfront properties, many of which boast breathtaking views of the Assawoman Bay. Imagine waking up to the gentle sound of waves lapping against the shore and enjoying your morning coffee on a private deck as the sun rises over the horizon. The community is designed with nature in mind, featuring lush landscapes, serene walking paths, and access to a variety of recreational activities.

Residents of Oyster Harbor enjoy a plethora of amenities, including a community clubhouse, a sparkling swimming pool, and private boat slips for those who love to explore the waters. The subdivision's strategic location means you're just minutes away from the vibrant boardwalk, pristine beaches, and an array of restaurants, shops, and entertainment options that Ocean City is famous for.

For families, the area is served by excellent schools and is close to parks and recreational facilities. Whether you're an outdoor enthusiast eager to kayak, fish, or simply soak in the sun, or someone who enjoys the lively atmosphere of Ocean City, Oyster Harbor provides the perfect backdrop for your dream lifestyle.

Discover the charm of Oyster Harbor, where coastal living meets community spirit, and make this enchanting subdivision your next home!

Newest Listings in Oyster Harbor

26 Oyster Road Unit 24, Urbanna
$584,900
1 Beds ⋅ 2 Baths
Enjoy low-maintenance waterfront living from this beautifully appointed 1-bedroom, 1.5-bath condo overlooking scenic Urbanna Creek. Built in 2012, this second-floor, elevator-accessible unit features an open living and dining area with wood flooring and a well-equipped kitchen. The light-filled sunroom offers stunning panoramic views of Urbanna Creek, creating the perfect place to relax and watch the boats go by. The waterside primary suite features luxury vinyl flooring, a walk-in closet with custom built-in shelving, and an ensuite bath. Included with the property is a deeded 40-foot boat slip (Slip #1) with approximately 9+ feet of mean low water, making it ideal for larger vessels and boating enthusiasts. Additional amenities include a dedicated lower-level storage locker (#8) and access to the community's waterfront swimming pool. A rare opportunity to enjoy the best of waterfront living with boating access, exceptional views, and easy access to everything charming downtown Urbanna has to offer.

26 Oyster Road Unit 24, Urbanna

Listing courtesy of Cobblestone Realty Inc.. Contact:

3349 Arundel On The Bay Rd, Annapolis
$670,000
4 Beds ⋅ 3 Baths
Welcome to your turn-key coastal retreat in the highly sought-after water-privilege community of Oyster Harbor! Situated on a rare double lot, this beautiful 4-bedroom, 3-full-bath home offers the perfect blend of modern updates and outdoor flexibility. The main level shines with refinished hardwood floors, a freshly painted interior, and a bright, open-concept kitchen, living, and dining area. Step through the glass doors onto the elevated wrap-around deck—an entertainer's dream perfect for catching cool breezes off the Chesapeake Bay. Retreat to the private primary suite addition, featuring a cozy stone fireplace, dual closets, with a private bath. The fully finished lower level boasts brand-new wall-to-wall carpet, a spacious family room, a full bath, a fourth bedroom, den, and ample storage space. Outside, the expansive double lot provides endless possibilities for a garage, boat storage, or custom gardens. Enjoy premier community amenities including a private beach, playground, and boat slips. Don't miss this incredible opportunity to live the Coastal Annapolis Lifestyle!

3349 Arundel On The Bay Rd, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

10226 Bent Creek Rd, Ocean City
$479,900
3 Beds ⋅ 2 Baths
Welcome home to this beautifully renovated 3-bedroom, 2-bath home located in a sought-after community! Thoughtfully updated in 2024, this move-in-ready property features a new kitchen and baths, stylish LVP flooring, and a cozy fireplace. Situated on a desirable corner lot, the home also offers a back deck perfect for relaxing or entertaining, along with a spacious 2-car garage. Modern updates, inviting spaces, and a great location make this home a must-see!

10226 Bent Creek Rd, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact:

1245 Creek Dr, Annapolis
$680,000
3 Beds ⋅ 2 Baths
Nestled in the charming Oyster Harbor community, this delightful Cape Cod-style home offers a perfect blend of comfort and modern living. With three spacious bedrooms and two full baths, including a luxurious soaking tub and a walk-in shower, this residence is designed for relaxation. The open floor plan seamlessly connects the kitchen-boasting stainless steel appliances and an inviting island-to the cozy living area, complete with a gas fireplace for those chilly evenings. Step outside to enjoy the serene surroundings, with Oyster Creek and the community beach and pier just a short stroll away, perfect for nature lovers. The expansive deck overlooking the headwaters of Oyster Creek and the front patio provide an ideal space for outdoor gatherings. The community is enriched by playgrounds, water access and nearby parks, ensuring a vibrant lifestyle. With a generous driveway accommodating up to five vehicles, this home is ready to welcome you. Experience the warmth and charm of Oyster Harbor-your new sanctuary awaits!

1245 Creek Dr, Annapolis

Listing courtesy of Compass. Contact:

10221 Bent Creek Rd, Ocean City
$599,899
4 Beds ⋅ 4 Baths
Located in the popular community of Oyster harbor in West Ocean City, this 4 bedroom home offers enjoyable coastal living, The home has been freshly painted and is ready for the new buyer , step inside and enjoy the comfortable flow of this floorpan , Home features include some of the following, Granite counters, wood floors, gas fireplace, Primary bed and bath on the 1st floor , private 2nd floor bedroom and Bath, Larger attic storage, all this and a garage

10221 Bent Creek Rd, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact:

1326 Harbor Rd, Annapolis
$975,000
4 Beds ⋅ 4 Baths
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

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

3268 Kitty Duvall Dr, Annapolis
$949,990
5 Beds ⋅ 4 Baths
Huge Price Drop + $5,000 Closing Help! New Construction Colonial Ready by End of Year* Schaefer Homes presents this stunning new Colonial in the prestigious Oyster Harbor community, with completion targeted for the end of 2026. Set on a sprawling 0.62-acre lot, it offers rare space and privacy, with plenty of room for a garden retreat, entertaining terrace, or open yard. The thoughtful floor plan includes 5 spacious bedrooms and 3.5 baths, plus a showstopping gourmet kitchen with upgraded design features and premium finishes. With its classic vinyl siding exterior and modern new-construction interior, this home blends timeless charm with the quality craftsmanship Schaefer Homes is known for. Oyster Harbor is a serene, exclusive community and one of the area’s most sought-after addresses. Don’t wait. Schedule your private appointment today! *Closing cost assistance terms and conditions apply.

3268 Kitty Duvall Dr, Annapolis

Listing courtesy of Blackwell Real Estate, LLC. Contact:

3280 Arundel On The Bay Rd, Annapolis
$750,000
5 Beds ⋅ 5 Baths
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

Listing courtesy of The KW Collective. Contact:

1254 Washington Dr, Annapolis
$925,000
5 Beds ⋅ 5 Baths
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

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

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