250 properties for sale in Oyster Harbor

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 dec

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 H

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home complete with elevator. Takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the waters edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. Theres 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled fo

Rarely available, all-brick rancher in the amenity-rich, sought-after Hillsmere Shores community. This home has been meticulously cared for and loved, and it will show from the moment you step in! Gleaming hardwood floors, freshly painted interior, and abundant natural light perfectly framed by custom plantation shutters are your first signs that this is a special home. As you make your way through the dining/eating area, you will begin to realize that there is way more space inside than you might have imagined from the outside. Prepare to be completely wow'd as you step into the four-season room! Vaulted ceilings, skylights, a brick accent wall, a pellet stove, and a dedicated Mitsubishi split heat and A/C system will quickly make you realize you have found your favorite room in the house. The second bathroom's shower was converted for accessibility to main level laundry. Enjoy the convenience, or easily convert back as there is still laundry available in the basement. Speaking of the

Direct, unobstructed views of Chesapeake Bay define this terrace-level home in Chesapeake Harbour. The two-bedroom, two-bath condominium features an open living and dining area centered around a fireplace, plus a kitchen with granite countertops, a subway-tile backsplash, and white cabinetry. A patio at the front and another at the rear provide two distinct outdoor spaces. The primary bedroom is well-appointed and includes direct patio access and a generously sized walk-in closet. A second bedroom, a full hall bath, and in-unit laundry complete the interior. The current floor plan measures approximately 1,267 square feet of finished interior space. Chesapeake Harbour is a gated waterfront community with 24-hour security and convenient access to downtown Annapolis. Amenities include a private beach, marina, two pools, tennis and pickleball courts, walking paths, kayak access and storage, and waterfront dining within the community. Few homes in this community see the water this directly.

GREAT PRICE and all major items replaced. Space, flexibility and the Annapolis water-oriented lifestyle come together at 1007 Harbor Drive, offering 3722 finished square feet, four bedrooms, three full and two half baths, a two car garage and a finished lower level. All in the sought-after Annapolis Roads community. The versatile floor plan provides room to spread out, work from home, entertain and accommodate guests, while the finished lower level adds a recreation room, kitchenette, full bath, bonus room and private entrance. Outdoor living is equally impressive. Enjoy the screened porch, deck, 10-person hot tub and newly built fire pit with custom paver patio overlooking the level, fenced backyard. An extra-wide driveway provides parking for additional vehicles, a boat or RV, while the two-car garage offers extensive storage with a floored attic, shelving and cabinets. Inside, hardwood and luxury vinyl plank flooring, fresh paint, new upstairs carpet and recessed lighting complement

Discover easy, turn-key living in this beautifully maintained two-bedroom, two-bathroom condo overlooking a peaceful courtyard. This move-in-ready opportunity offers an incredible community lifestyle. Cool off during hot summer days in the community pool, host effortless gatherings at the picnic area, or enjoy a game at the nearby pickleball and tennis courts. If you love the outdoors, the spectacular Quiet Waters Park is just minutes away. Ideally located just minutes from downtown Annapolis, premier dining, and shopping, this home offers the perfect blend of convenience and tranquility. Step inside to a spacious living room that opens to a private balconyperfect for your morning coffee or relaxing evenings. The functional layout features a separate dining area and a nicely remodeled kitchen with an adjoining breakfast space/den, offering both comfort and versatility. Both the primary suite and the second bedroom are generously sized, providing a welcoming retreat at the end of a busy

OPEN HOUSE MONDAY SEPTEMBER 28, 2026 FROM 4:00-5:00 PM List Price is Opening bid at Online Auction to be conducted on auctioneer's website. Online Auction Only! Bidding begins Saturday, September 26th and ends Thursday October 1, 2026 at 1:00 PM. Waterfront-Inspired Annapolis Living with Exceptional Community Amenities Experience the appeal of Annapolis living at 2004 Quay Village Court, Unit T-1, a desirable main-level condominium in the water-privileged First Village of Chesapeake Harbour community. Offering an inviting blend of comfort, privacy, and resort-style amenities, this residence presents an exceptional opportunity to create a refined retreat in one of Marylands most desirable waterfront communities. Inside, The main-level design offers effortless one-floor living, with an open living and dining area (with a fireplace), Powder room, designated laundry area, and kitchen. The living space extends outdoors via the rear patio, creating a welcoming setting for morning coffee, eve

New price for an exceptional property! Experience the ultimate waterfront lifestyle in the prestigious Harbour Village Marina at Chesapeake Harbour, where panoramic marina views and exceptional amenities create one of Annapolis' most sought-after communities. This beautifully updated 3 bedroom 3 bath waterfront condominium offers an inviting blend of elegance, comfort, and coastal charm. Wake each morning to tranquil marina views from your private balcony, spend your afternoons enjoying the private sandy beach, waterfront pool, tennis and pickleball courts, or simply watch the boats come and go from one of the area's premier marinas. Whether you're an avid boater or simply appreciate life on the water, this is waterfront living at its finest. Inside, the spacious floor plan is designed for both everyday living and effortless entertaining. The living room and primary suite each feature a gas fireplace, creating warm and inviting spaces to unwind. Multiple balconies capture beautiful mar

OPEN HOUSE: Sat, 10/24 from 12-2*Experience exceptional waterfront living at 7428 Bluffs Lane, Unit C2. Tucked away in a secluded 11-unit community on a private road, this beautifully updated home offers ground-level entry with no stairs, ample parking, and breathtaking water views at every turn. Step through the foyer and immediately take in the water, with a dramatic wall of windows and sliding doors spanning the back of the home and showcasing the serene setting from virtually every angle of the living spaces. The open floor plan features hardwood floors throughout, a dedicated dining area, bar seating, recessed lighting, crown molding, a wood-burning fireplace and a spacious kitchen with a tile backsplash, stainless appliances, abundant cabinet storage and under-cabinet lighting. Thoughtful upgrades include new designer interior doors throughout, elegant acrylic door knobs, Hunter Douglas blinds, customized closets for efficient storage and an HVAC system replaced in 2022. Both bat

Truly charming 4 bed. & 2 bathroom Cape Cod on almost half acre lot with 2 sheds/ work shops; in Eastport general area. Really nice big porch to enjoy your morning coffee. Freshly painted inside and out with recent upgrades. Classic features include hardwood floors, built-ins and custom trim. Great bonus sunroom/ office space. Separate dining & living room. Roof 5 years new and new boiler. Great lifestyle with easy stroll to downtown Eastport & Historic Annapolis shops, restaurants & Quiet Waters Park on the South River; with its extensive biking & hiking trails and doggie parks & beach. Also summer concerts & other events. Great place to call home!:)

Welcome to 952 Yachtsman Way an Annapolis home with space, character, and the opportunity to make it your own in the sought-after Mariners Point community. This 2-bedroom, 2-bath home features a bright, open layout with vaulted ceilings, abundant natural light, and a wood-burning fireplace that anchors the main living space. The dining area opens to a rear deck and backyard, creating an easy flow for everyday living, grilling, entertaining, or simply enjoying the outdoors. The main level offers a bedroom and full bath, while the upper level includes a second bedroom plus flexible loft-style space that can serve as a home office, reading nook, or additional living area. Recently refreshed with interior paint, the home also offers off-street parking, outdoor storage, and access to Mariners Point community amenities including the pool and clubhouse. Located just minutes from downtown Annapolis, Eastport, Quiet Waters Park, shopping, dining, marinas, and major commuter routes, 952 Yachtsma

Welcome to a rare opportunity in sought-after Mariners Point! One of the largest residences in the community, this spacious 3-bedroom, 2.5-bath townhome offers an exceptional combination of generous living space, thoughtful updates, and an expansive backyard nestled against a private, tree-lined setting. Step inside to a beautifully renovated kitchen featuring all-new appliances and brand-new flooring, giving the home a fresh, updated feel thats truly move-in ready. A cozy fireplace brings warmth and character to the main living area, while a staircase leads to an airy upper-level loft overlooking the space below. Upstairs, the spacious owners suite is enhanced by high ceilings, creating an open and inviting retreat. Outdoor living is equally appealing, with a sizable backyard, patio, and deck overlooking mature treesan ideal setting for entertaining, outdoor dining, or simply relaxing in peaceful surroundings. Two driveway parking spaces add everyday convenience. Mariners Point offers

SELLER IS OFFERING $10,000 toward a new fence or buyer closing costs, providing added flexibility and value for the next homeowner. This exceptional Annapolis home truly has it all. Beautifully maintained, move-in ready home on a private lane. Updated with features that include a new roof, skylight, gutters, heat pump, hot water heater, carpet, sliding glass door, basement outdoor steps, fresh paint and more. The spacious kitchens vaulted ceiling has a skylight with a remote-controlled shade, beautiful quartz countertops, tile backsplash, breakfast bar, stainless steel appliances and opens to the family room with a wood-burning fireplace. The expansive screened porch is perfect for morning coffee, relaxing and entertaining. Elegant wood style flooring enhances the main living areas including a separate dining room and a large living room. Bathrooms have been tastefully updated. The unfinished basement with DryLok painted walls offers excellent potential for future living space. Well in

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 deckan 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

Beautiful Views of Chesapeake Bay and Chesapeake Harbour Marina immediately capture your attention in this stunning 2-bedroom, 2-bathroom waterfront condo at Chesapeake Harbour. Bright, open, and filled with natural light, this spacious home offers just over 1,200 square feet of comfortable living space with an inviting floor plan that is perfect for both everyday living and entertaining. The Tuscan-style kitchen opens seamlessly to the dining and living areas, creating an easy flow throughout the main living space. A wood-burning fireplace adds warmth and character to the living room, while large windows and doors bring the beautiful waterfront surroundings into the home. One of the most exceptional features is the expansive balcony accessible from both the living room and primary bedroom. This wonderful outdoor space offers breathtaking panoramic views of the Chesapeake Bay and Chesapeake Harbour Marina, along with a clear view of the Bay Bridge. Whether you're starting your day with

Price adjusted as sellers have found their next home! Welcome to easy waterfront living in the heart of Eastport. Rarely available and beautifully renovated, this top-floor 2-bedroom, 2-bath condominium in the sought-after Severn House community offers direct views of Back Creek, turnkey interiors, and effortless access to the Annapolis waterfront lifestyle. Inside, the residence has been thoughtfully updated with a clean, coastal feel and comfortable, move-in ready finishes throughout. The open-concept living spaces are bright, inviting, and designed for easy everyday living. The kitchen opens to the dining area and living room, creating a comfortable flow for entertaining, gathering, or simply enjoying the sense of space. From the main living area, sliding glass doors lead to a private balcony with direct views over Back Creek, adding a beautiful waterfront backdrop to the home. The primary suite features an ensuite bathroom and walk-in closet, while the second bedroom offers a graci

Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and high-end upgrades from top to bottom. The open, light-filled layout features stylish new LVP flooring (Oct 2024) and contemporary lighting throughout (2024). Cook and entertain in the updated kitchen with custom cabinetry and quartz countertops (Dec 2024), plus brand-new appliances (Jan 2025). Relax in the primary suite with its custom Closet America walk-in closet (Sept 2025). Living in Chesapeake Harbour gives you direct access to a deep-water marina, private beach, pools, tennis courts, 24/7 security, and an on-site waterfront restaurant, all just minutes from historic Downtown Annapolis

Something special is coming to hillsmere shores! Get ready to fall in love with 103 Great Lake Drive, an exciting new opportunity in one of Annapolis' most sought-after waterfront communities! Offering wonderful versatility and inviting spaces designed for both everyday comfort and effortless entertaining, this home features 2 fireplaces, a fabulous deck perfect for outdoor gatherings, and a separate in-law, nanny, or au pair suite that provides exceptional flexibility for extended family, guests, or multigenerational living. Imagine cozy evenings beside the fire, summer dinners under the stars, and weekends enjoying everything that makes Hillsmere Shores so specialincluding its beautiful community beach, marina, pool, and vibrant waterfront lifestyle. All just minutes from Historic Downtown Annapolis, shopping, dining, and everything the Chesapeake Bay region has to offer. A home with character, flexibility, and an address you'll love. More details and photographs coming soon. Stay tu

Don't miss out on this great location. Fall is here and it is time to make your move and be settled in before the holiday season is here! Must see inside to appreciate all this home has to offer. Sellers are highly motivated! Details and features; The kitchen used to be the carport. The upper cabinets in the kitchen are custom made. Luxury vinyl flooring in kitchen. Propane fireplace in living room/insert is only 2 years old. Propane gas for grill. 2-100-gallon propane tanks/owned. Propane back up heat. Blown in insulation in attic area. Master bath gutted and updated 5 years ago. HVAC units in lower level and in barn/garage. Lower-level walk out to bar area and firepit. Full covered huge deck. Fully fenced back yard. Private access to Quiet Waters Park. Metal roof on barn/garage. Custom built doors on barn/garage This home is located in the highly desirable Hillsmere Shores community, offering a private beach, community pool, marina, and multiple launch areas for boats, kayaks, canoes

Welcome Home! You don't want to miss this great news! The seller's loan is ASSUMABLE @ 2.875 % to qualified buyers. This beautifully Renovated Eastport Marina Condo with Deeded 30 Slip A 54 & Waterfront Pool. This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuiltnew electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring butcher-block countertops, stainless-steel appliances, gas range with vent hood, built-in microwave, and designer recessed lighting throughout the home. Custom built-ins include a butlers pantry and laundry cabinetry for smart, hidden storage. A full wall of sliding glass doors opens to a spacious deck offering peaceful seasonal views of Back Creek. The residence also includes a large deeded basement storage unit. Enjoy exclusive ownership of a deeded deep water 30+ foot boat slipone of the few in Annap

Welcome to 293 Cedar Lane, a classic 1963 ranch on a private. 27 acre lot in the water privileged community of Hillsmere Estates, steps from Quiet Waters Park and minutes to the South River. Original hardwood floors flow through the main level, where a living room with custom built in shelving opens to a galley kitchen with an electric stove top, wall oven, and dishwasher, full of potential for your personal touch. The full bath keeps its classic pedestal sink charm. Downstairs, a full basement offers a finished rec area and bonus room alongside generous unfinished storage and utility space, ready for however you want to use it. Step outside to a rear deck made for morning coffee or evening unwinding. Ceiling fans keep the main level comfortable, while public sewer and a private well simplify utilities. Sold strictly as is, this well loved home offers real bones in one of Annapolis's most sought after neighborhoods, home to a private beach, marina, and community pool. Come discover wha

Discover Your Dream Home in Coveted Mariners Point! Perfectly positioned in the highly sought-after Mariners Point community of Eastport-Annapolis, this charming end-of-row townhome offers the ultimate blend of convenience, comfort, and coastal living. Just moments from the Chesapeake Bay, it provides a peaceful retreat while keeping you effortlessly close to the rich history, dining, shopping, and culture of Annapolis. As a bright and airy end-unit, the home shares only one wall, allowing abundant natural light to pour in throughout the day. Spanning three finished levels with over 1,800 sq. Ft. of living space, it features 3 generously sized bedrooms and 3.5 bathrooms. The inviting floor plan seamlessly connects the living and dining areas to a well-appointed kitchen, complete with gorgeous wood-look laminate floors, a cozy space for casual dining, and updated stainless steel appliances. Home Highlights: New Kitchen Appliances: Enjoy peace of mind with a brand-new stainless steel ref

Life takes on a different pace in Oakwood, where the calm waters of Fishing Creek and the South River provide an idyllic backdrop and effortless access to the Chesapeake Bay. With 93 feet of shoreline, a private pier with multiple slips, and a substantial 25,000-pound boat lift, this property is perfectly suited for boating enthusiasts and those who appreciate the beauty and tranquility of the Chesapeake lifestyle. Designed for both everyday comfort and effortless entertaining, the home offers an inviting open floor plan with seamless flow between the gourmet kitchen with center island, sunroom, soaring two-story living room, and adjacent family room. Walls of windows frame picturesque water views and fill the home with natural light. A versatile main-level room with an adjoining full bath provides ideal space for guests, a private office, or flexible living needs. Upstairs, the spacious primary suite serves as a peaceful retreat with abundant windows capturing the ever-changing waterf

Price Improvement! Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures,

25,000 Price reduction! Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full

Open house saturday, 10/17, 12-2pm! Character, comfort, and versatility come together in this beautifully appointed Hillsmere home. Set among large, mature trees within an established waterfront community, the main level offers an open, airy feel with vaulted ceilings, attractive flooring, and a kitchen with stainless steel appliances. Every bathroom has been remodeled, including the primary suite's bath with a spacious shower, tile flooring, and custom shelving. The finished lower level adds a bedroom, an updated half bath, and a rec room wood stove, while a bonus room with its own private entrance offers flexible space for an office, studio, or additional living area and could potentially be converted back to a one-car garage. Outside, an expansive private yard bordered by a creek provides a serene backdrop, along with a spacious deck. Hillsmere is adjacent to Quiet Waters Park, and community amenities include an outdoor pool, marinas, beaches, playgrounds, a boat ramp, and boat stor

Welcome home to this beautifully updated 2-bedroom, 2-bathroom condo, offering comfortable living, stylish upgrades, and an unbeatable location within the community. The updated kitchen features new soft-close cabinets and new quartz countertops, creating a fresh and modern space for cooking and entertaining. The condo also boasts new flooring and fresh paint throughout, giving the entire home a bright, clean, move-in-ready feel. Relax by the cozy fireplace or step outside onto the private deck off the bedroom, where you can enjoy beautiful water views and unwind at the end of the day. For added convenience, the condo is located right next to the community pool, making it easy to enjoy resort-style amenities just steps from your door. You'll also appreciate being close to shopping, dining, and everyday conveniences. With its thoughtful updates, water views, convenient location, and community amenities, this condo is a wonderful place to call home! More than one photo virtually staged