Oyster Harbor Real Estate

Oyster Harbor Real Estate

Welcome to Oyster Harbor, a hidden gem nestled in the picturesque landscapes of Maryland. This charming subdivision offers a unique blend of serene coastal living and vibrant community spirit, making it an ideal choice for families, retirees, and anyone seeking a tranquil lifestyle.

Oyster Harbor is strategically located just moments away from the breathtaking shores of the Chesapeake Bay, providing residents with easy access to sandy beaches, boating, and a plethora of water activities. The community is enveloped by lush greenery and mature trees, creating a peaceful retreat from the hustle and bustle of city life, while still being conveniently close to essential amenities.

Life in Oyster Harbor is characterized by a tight-knit community feel, where neighbors become friends and local events foster connections. The subdivision features beautifully designed homes that reflect a harmonious blend of modern comfort and classic charm, each offering spacious layouts and stunning outdoor spaces perfect for family gatherings or quiet evenings under the stars.

For those who love the outdoors, Oyster Harbor is surrounded by scenic parks and nature trails, ideal for hiking, biking, or simply enjoying a leisurely stroll. Additionally, the area boasts excellent schools, shopping centers, and dining options, making it a well-rounded environment for families and individuals alike.

Whether you’re looking to settle down or invest in a vacation home, Oyster Harbor offers a slice of Maryland paradise that you won’t want to miss. Come explore this enchanting community and discover why so many choose to call Oyster Harbor home!

Newest Listings in Oyster Harbor

4 Beds ⋅ 3 Baths

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

Listing courtesy of TTR Sotheby's International Realty. Contact: (703) 745-1212

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

Listing courtesy of Real Estate Professionals, Inc.. Contact:

5 Beds ⋅ 5 Baths

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

Listing courtesy of The KW Collective. Contact: 4435741600

4 Beds ⋅ 3 Baths

Construction has began on this beautiful Schaefer Homes, design!! Ready in November! Discover an unparalleled opportunity to own a luxurious, newly constructed Colonial masterpiece in the prestigious Oyster Harbor community. This exquisite residence, set to be completed in 2026, boasts a sprawling 0.62-acre lot, offering ample space for outdoor entertaining and serene relaxation. With 4 spacious bedrooms and 2.5 elegantly designed bathrooms, this home is a canvas for your dream lifestyle. The architectural elegance of vinyl siding complements the sophisticated interior layout with stunning gourmet kitchen and upgraded design features! Embrace the exclusive lifestyle that comes with living in Oyster Harbor, where luxury meets tranquility. This is more than a home; it's an invitation to a life of elegance and comfort. Don't miss your chance to make this dream a reality!

3268 Kitty Duvall Dr, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

3 Beds ⋅ 2 Baths

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

Listing courtesy of Keller Williams Flagship. Contact:

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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Jessica Sauls | Realtor | Memory Lane Property Group

With over two decades of experience and thousands of successful home sales, I provide calm, confident guidance through every stage of the real estate journey. Since 2003, I’ve helped buyers, sellers, investors, military families, and those navigating major life transitions make smart, well informed decisions. I do this with clarity, integrity, and strong advocacy. Real estate is more than a transaction, it’s deeply personal. I’m known for creating a steady, reassuring experience during what can often feel overwhelming. My clients value my ability to listen closely, communicate clearly, and protect their interests at every step. Whether negotiating complex terms, preparing a home for market, or navigating unexpected challenges, I lead with professionalism, transparency, and care. As a top performing Realtor in Maryland and Pennsylvania, I combine deep market expertise with a strategic, hands on approach. I help sellers maximize value through thoughtful preparation, including repairs and upgrades with payment deferred until closing. For buyers, I provide honest insight, strong negotiation, and a no-pressure approach. I want all of my Clients to move forward with confidence. Having successfully navigated multiple market cycles, I understand how to adapt strategies in changing conditions while keeping my clients’ goals front and center. Beyond real estate, I am deeply committed to my community, supporting scholarships, housing initiatives, and local education. That commitment to service carries into my work, showing up fully, advocating fiercely, and always doing what’s right for my Clients. If you’re looking for an experienced, steady professional who will treat your goals with care and deliver a strong, strategic outcome, I would be honored to work with you. It's my Mission to provide strategic, ethical, and compassionate real estate guidance that empowers people to build stability, wealth, and a life they love. We create calm, clear, and trustworthy experiences, and we strengthen our community through service, connection, and integrity. I believe in building futures, relationships, and legacies that last.

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Brian Sauls | Realtor | Memory Lane Property Group

Brian brings a thoughtful, detail-oriented approach to every real estate transaction. He helps clients understand the true condition and quality of a home beyond surface details, offering valuable insight during showings and throughout the decision-making process. Known for his calm demeanor, reliability, and strong attention to detail, Brian ensures clients feel comfortable, informed, and well supported from start to finish. He answers questions in real time, offers practical perspective, and helps buyers assess homes with confidence and clarity. Brian’s approach is grounded, professional, and service-oriented. His ability to provide meaningful guidance while keeping the process smooth and stress-free makes him a trusted advocate for his clients every step of the way.

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Christina Jones | Client Care | Memory Lane Property Group

Christina is the heart of our client experience and serves as our Director of Client Care. From the moment a client enters our world to well beyond the closing table, Christina ensures every detail is handled with care, clarity, and consistency. With a calm, organized, and compassionate approach, Christina manages communication, timelines, and behind-the-scenes coordination so our clients feel supported and informed at every step. She is often the friendly voice checking in, the steady hand keeping everything on track, and the person making sure nothing slips through the cracks. Christina is deeply committed to creating a smooth, low-stress experience for buyers and sellers alike. She understands that real estate transactions often come during significant life moments, and she brings patience, empathy, and professionalism to each interaction. Her focus on service, follow-through, and genuine care allows our team to deliver a thoughtful, high-level experience — one where clients feel heard, respected, and confident throughout the process.

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Payson Clausen Realtor

Payson Clausen | Realtor | Memory Lane Property Group

Payson Clausen brings together years of experience in real estate, media production, and marketing to support our team and elevate the client experience. With a strong background in both the real estate industry and creative media, Payson plays a key role in how properties, brands, and stories are presented. His expertise in video production, marketing strategy, and digital content helps ensure our listings and messaging are clear, compelling, and thoughtfully executed. Beyond his professional skill set, Payson is deeply committed to serving his community. He regularly volunteers his time working with local students and is actively involved in raising funds for SkillsUSA, supporting career and technical education programs that prepare young people for future success. Payson’s blend of industry knowledge, creative talent, and community involvement reflects our team’s values — using our work not just to serve clients, but to make a meaningful impact beyond the transaction. (function() { var rg = document.createElement('script'); rg.type = 'text/javascript'; rg.async = true; rg.src = 'https://widgets.realgeeks.com/static/js/search_widget_new.js?v=3'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(rg, s); })();

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