74 properties for sale in Flag Harbor

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 home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Deeded Boat Slip Conveys! Bayside Living! Bayview new construction only a short walk to the private beach & marina! This 2000sqft 3 Bed 2.5 Bath Colonial with an attached 1.5 Car Garage & an Unfinished Basement, has been designed to Maximize the Views while the. 91 acre lot maximizes privacy! The primary bedroom & attached balcony will have substantial views of the Chesapeake Bay! This floorplan has been designed to give buyers the open concept they have been looking for along with good sized bedrooms to boot. Oversized 1.5 Car Garage is perfect for storing your car and having a workshop! Engineering is already complete shortening the wait time! Call to discuss standard features/upgrades! It's hard to find new construction w/ Water Access, a Deeded Boat Slip and Bay Views under $600k! Reach out now to be in your new home by Early 2027! Inquire ASAP Before this opportunity is GONE!

Welcome to this beautifully maintained Colonial offering water views of the Chesapeake Bay! Nestled on a generously sized lot with a fenced backyard, this home features a welcoming front porch, an oversized paved driveway, a one-car garage, a storage shed, and a large deck! Inside, you'll find hardwood floors throughout much of the home and a thoughtfully updated kitchen renovated in 2020/2021 with stylish finishes, tile flooring and backsplash, shiplap ceiling details throughout, floating shelves, a new double oven (2026), and a newer refrigerator (2025). The main level also includes a dedicated home office with French doors, a formal dining room, and a comfortable living room. Upstairs, the spacious owner's suite offers a walk-in closet with a custom organization system and a private en suite bath featuring dual vanities, tile flooring, a soaking tub, and a glass-enclosed shower. Two additional bedrooms and another full bath complete the upper level. The finished walk-up basement add

Welcome to 1430 Plateau Road in Saint Leonard, Marylanda charming property that offers the perfect blend of comfort, privacy, and the beauty of Southern Maryland living. This well-maintained 3-bedroom, 2-bathroom home features a functional floor plan designed for everyday living and entertaining. The spacious living areas provide plenty of natural light, while the thoughtfully designed kitchen offers ample cabinetry and workspace for preparing meals. The primary suite includes a private full bath, creating a comfortable retreat at the end of the day. Enjoy the peaceful outdoor setting with room to relax, garden, entertain, or simply take in the surrounding scenery. Whether you're enjoying your morning coffee on the porch or hosting a backyard gathering, this property offers the flexibility to make the outdoor space your own. Conveniently located near local parks, marinas, shopping, dining, and commuter routes, you'll appreciate the balance of tranquility and accessibility this location

This private cedar cottage is situated on a quiet cul-de-sac within view of boats docked at Flag Harbor Yacht Haven. The cottage has two levels with bedrooms and bathrooms on both levels. The kitchen has an open floor plan to the dining area and living room. It has been completely painted inside as well as new luxury vinyl planking (LVP) in place. Use it as your primary residence or your weekend retreat. Wouldn't it be wonderful to have your boat docked a block away with the Chesapeake Bay right outside of the marina? Don't let this opportunity slip away!

Vacation year-round at this charming Chesapeake Bay waterfront retreat, offering breathtaking panoramic views, walkable private/community-only beach access, and access to the community boat ramp for enjoying life on the water. From the moment you arrive, the curb appeal and landscaping set the tone. Inside, beautiful hardwood flooring flows throughout the home, leading into an open and inviting layout. The living area features a cozy wood-burning fireplace with built-in shelving and opens seamlessly to the dining space, where large windows capture stunning water views. A sliding glass door leads to the expansive rear deck, creating an effortless indoor-outdoor flow for relaxing or entertaining. Just off the family room, the kitchen offers ample cabinet space and recessed lighting. Designed with flexibility in mind, the home offers a spacious primary suite with two closets, a private attached bathroom, and direct access to the rear deck overlooking the Chesapeake Bay. The perfect spot f

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

Welcome home to 4585 Mattapany Road, where peaceful country living meets everyday convenience. Nestled on nearly 1.5 private acres in the desirable Woodhaven community, this beautifully maintained Colonial offers approximately 3,300+ finished square feet of thoughtfully designed living space across three finished levels. The main level features formal living and dining rooms, a welcoming family room with a cozy fireplace, and a generously sized eat-in kitchen with upgraded stainless steel appliances. Whether youre entertaining friends or enjoying a quiet evening at home, the thoughtfully designed floor plan offers comfortable spaces for every occasion. The inviting covered front porch is the perfect place to enjoy your morning coffee while taking in the peaceful surroundings, while the expansive rear deck overlooks the private backyarda wonderful setting for entertaining and making lasting memories. Upstairs, youll find four generously sized, light-filled bright bedrooms, all featuring

Opportunities like this dont come along often. Set on 10 acres in Saint Leonard, this home offers a rare chance to live, earn, and create something that fits your life. Whether youre looking to house hack, bring multiple generations together with true separation, or run a business from home, this property gives you the flexibility to do it. Inside, youll find 3,600 square feet of updated living space, thoughtfully divided into private units. Step outside and the setting takes over. Two ponds, open land, and wide views create a sense of space and calm thats hard to find. The large patio and front porch invite you to slow down, while the oversized garage, workshop, and separate barn give you room to build, store, or grow a business. Zoned mixed-use in the town center, this property opens the door to a variety of uses. Buyers should confirm specific plans with Calvert County, especially if considering additional building on the land. Located just minutes from the heart of Saint Leonard, w

Beautifully refreshed and full of potential, this charming rambler on basement sits on approximately 1 private acre in the peaceful rural setting of St. Leonard. This property features no HOA, a fully unfinished basement with rough-in for an additional bathroom, and an impressive approximately 75 x 40 pole barn ideal for contractors, hobbyists, car enthusiasts, equipment storage, workshop space, or additional storage needs. Inside, the home has been recently freshened up with updates made to the kitchen and baths, in addition to fresh paint throughout, updated flooring, and new carpet installation, creating a clean and move-in ready feel. The living room offers cathedral ceilings, ceiling fan, sliding glass doors, The laundry is conveniently located on the main level. Located just minutes from the Chesapeake Bay, Solomons Island, local marinas, waterfront dining, parks, and beaches, this home offers easy access to boating, fishing, and all that Southern Maryland coastal living has to o

This exceptional waterfront home offers sweeping views of the Chesapeake Bay, and a setting that feels like a retreat every single day. Set on over an acre with 200+ feet of shoreline, the property blends natural beauty with thoughtful upgrades, creating a space that is both refined and relaxed. Inside, you’ll find over 4,000 square feet of living space designed to capture the water from nearly every angle. The main level features a primary suite, making everyday living easy and flexible. The kitchen opens to dining and living areas, all filled with natural light and framed by the Bay beyond. Upstairs and down, the home offers room to spread out, including a finished lower level with a full bath and bar area, ideal for entertaining or extended stays. Step outside and the property truly shines. Professionally designed ornamental gardens surround the home, creating a layered landscape of color and texture. Hardscaped patios, including a slate circular patio and paver terrace, offer perfe

Welcome to 5210 Knights Bridge Ct! Located on a quiet cul-de-sac and backing to mature woods, this well-maintained brick-front Colonial offers 4 bedrooms, 3.5 bathrooms, three finished levels, and an oversized two-car garage. The main level features an updated kitchen with cherry cabinetry, granite countertops, stainless steel appliances, subway tile backsplash, under-cabinet lighting, and a breakfast bar. Just off the kitchen is a breakfast area with built-in desk and cabinetry, along with a bright sunroom featuring skylights, casement windows, a cathedral ceiling, and a newer roof. The main level also includes a formal dining room and spacious family room. Upstairs are three bedrooms, including the primary suite with hardwood floors, two walk-in closets, and a large private bath with dual vanities, jetted tub, tiled shower, and towel warmer. The finished walkout lower level adds even more flexibility with a large recreation room and the fourth bedroom with its own en-suite bath, maki

Escape to Your Own Private Oasis: A Rare 4-Acre Calvert County Gem Finding usable, private acreage in Calvert County is a true raritybut finding it paired with a completely renovated, turn-key home is nearly impossible. Nestled along a peaceful, tree-lined country road where neighbors offer fresh-baked bread and farm-fresh eggs, this exceptional property offers the quintessential country lifestyle on nearly four pristine acres. Endless Possibilities Outdoors The land itself is a dream canvas. A flat, usable corner lot of this scale provides an expansive setting that is both manageable and majestic. With over half of the property remaining beautifully wooded, you have a totally secluded sanctuary where the neighbors are out of sight and nature takes center stage. Here, your backyard is limited only by your imagination: Create an Entertainment Hub: Pitch the ultimate oversized firepit area for cool autumn nights under starlit skies. Adventure at Home: Carve out your own private 4-wheelin

Welcome home to this spacious 4-bedroom, 2.5-bath home, situated on over an acre, offering a traditional floor plan designed for comfortable living and effortless entertaining. The main level features a formal living room, dining room, and a welcoming family room, providing plenty of space for gatherings both large and small. The kitchen flows seamlessly into the living areas, creating a functional layout for everyday living. Step outside to the deck, perfect for relaxing, grilling, or enjoying the private backyard setting. The unfinished basement offers a blank canvas with endless potential for additional living space, a home gym, workshop, or storage. Combining classic charm, generous living areas, and privacy, this home is ready for its next owner to make it their own

Nestled in the charming Long Beach Heights community, this delightful split foyer home offers a perfect blend of comfort and functionality. This residence boasts a spacious layout with three inviting bedrooms and two and a half bathrooms, making it an ideal retreat for those seeking a warm and welcoming atmosphere. The heart of the home is the country-style kitchen, complete with modern appliances including a built-in microwave, dishwasher, and electric oven/range, ensuring meal preparation is a breeze. The adjoining breakfast area is perfect for casual dining, while the formal dining area sets the stage for memorable gatherings. Natural light floods the home through double-pane, low-E windows, providing energy efficiency and a serene ambiance. The primary suite features a walk-in closet and a private bath, offering a personal sanctuary to retreat to at the end of the day. The fully finished basement, accessible via a connecting stairway, adds valuable living space and includes a laund

Some homes make you pause at the door. This is one of them. Renovated in 2025, this custom built 4 bedroom, 3.5 bath home is set on more than 5 wooded acres with over 6,000 sq ft of living space. Inside, a soaring two story foyer and dramatic staircase open to cathedral ceilings, hardwood floors, a light filled great room, and multiple living spaces designed for both everyday living and entertaining. The flexible floor plan includes a main level bedroom suite with full bath, a dedicated home office overlooking the woods, and three fireplaces throughout the home. Upstairs, the spacious primary suite offers its own fireplace, a spa inspired bath, generous proportions, and elevated views of the surrounding tree line. The finished walkout basement expands the living space even further with room for recreation, entertaining, fitness, or additional gathering space, plus a built in sauna and direct access to the lower patio. Outside, a rear deck, patio, expansive acreage, and mature woods cre

Nestled in one of Port Republic's most peaceful waterfront communities, this spacious 5-bedroom, 2-bath home offers the perfect blend of coastal charm and small-town living. The flexible floor plan features a welcoming living room, kitchen, two bedrooms, and a full bath on the main level. Upstairs you'll find a generously sized primary bedroom, two additional bedrooms, and a large hall bath, providing plenty of space for everyone. Enjoy glimpses of the water from the property, adding to the home's coastal appeal. The spacious driveway provides parking for up to four vehicles with room to accommodate a boatperfect for taking advantage of the nearby community boat ramp. A large, level side yard offers plenty of additional outdoor space for entertaining, recreation, gardening, or pets. Life here is all about enjoying the outdoors and the relaxed pace of a quiet, golf cart-friendly neighborhood. Just a short (though hilly) walk away, you'll find the community waterfront where residents enj

Beach community investment property. Discover the unbeatable Long Beach location and extraordinary upside potential with this St. Leonard property located at 5705 Oakcrest Drive. This home has Over 4,000 SF total space, with 3788 SF finished space! The property is located in a highly desirable, water-focused community with easy access to nearby beach and Flag Harbor marina within walking distance. It is ideal for coastal lifestyle enthusiasts who want a sprawling home with main level living plus income potential, multi-generational living, or even future caretaker accompaniment. The 65 x 32 rambler on basement with a 24 x 24 garage and massive rear outdoor living spaces has incredible renewal potential to customize, modernize, and create your dream home or investment property. Sold AS-IS at an attractive price point, this property represents an exceptional equity-building opportunity for savvy homeowners and real estate investors alike looking for maximum return in a prime Southern Mar

Welcome home to this spacious 4-bedroom, 2.5-bath home, situated on over an acre, offering a traditional floor plan designed for comfortable living and effortless entertaining. The main level features a formal living room, dining room, and a welcoming family room, providing plenty of space for gatherings both large and small. The kitchen flows seamlessly into the living areas, creating a functional layout for everyday living. Step outside to the deck, perfect for relaxing, grilling, or enjoying the private backyard setting. The unfinished basement offers a blank canvas with endless potential for additional living space, a home gym, workshop, or storage. Combining classic charm, generous living areas, and privacy, this home is ready for its next owner to make it their own

VA assumable mortgage at 2.625%! Welcome to 1054 Kings Creek Dr. Saint Leonard, MD 20685 a beautifully maintained Colonial in the sought-after Kings Creek Estates community, offering nearly 3,200 finished square feet, major recent capital improvements, and a private, wooded setting on more than one-half acre. Thoughtfully maintained, this home offers the ideal combination of generous living space, modern mechanical upgrades, and the privacy today's buyers are seeking. The inviting main level features hardwood floors; a spacious family room with a gas fireplace; formal dining room; dedicated home office, and an updated kitchen with granite countertops, stainless steel appliances, pantry, breakfast area, and recessed lighting. Upstairs, the spacious primary suite offers a walk-in closet, double vanity, soaking tub, and separate shower. The three additional bedrooms provide comfortable accommodations for family and guests. The finished walkout basement significantly expands the home's ver

Envision the possibilities in the Kenwood Beach community. This unique opportunity offers the chance to own in Calvert County while being within walking distance of the beach area and nearby waterfront amenities. Whether you're looking to restore, reimagine, or explore the property's future potential, this provides a blank canvas. Property is being sold strictly AS IS. Buyer is responsible for verifying all information, including zoning, utilities, permits, and any intended use of the property. Interior access may not be available, and buyers are advised to exercise caution at all times. Any items remaining on the property at the time of settlement shall convey with the property. If you've been searching for your next project, this is worth a closer look

Wake up to Chesapeake Bay views and spend your days enjoying one of Calvert County's best-kept secrets. This beautifully renovated non-riparian waterfront home sits directly across the street from a long community beach and private community pier, just steps from your front door. Whether you're launching a kayak, fishing from the pier, searching for fossils along the shoreline, or simply taking in the Bay breeze, the waterfront lifestyle is always within reach. Thoughtfully renovated inside and out, this home blends modern comfort with the character and charm that make Chesapeake Bay cottages so special. Original architectural details have been preserved and incorporated into the design, creating a warm coastal atmosphere that feels both timeless and inviting. The updated kitchen, baths, finishes, and systems allow you to move right in and start enjoying life by the water. Outdoor living takes center stage here. Gather with family and friends on the expansive terrace beneath the pergol

Open house sat august 29 1200- come on down. Now, this is what i call a house! There is So much to offer. Over 3800 Sq Ft. 2 Car Garage. Main Level Primary suite for you, a nanny, or in-laws with separate entrance, LR, Full Bath and Ramp. Easy and close access to Kitchen with SS appliances, granite countertops and open floor plan to DR, LR, Den area. TOTAL OF 5/6 Bedrooms, 4.5 Baths. Screened in Porch/Deck, Hot Tub, and that is just one level. Upstairs offers 4 Bedrooms 2 Full Baths and Laundry Room. Primary Bedroom offers Walk In Closet and Full Bath. Basement area offers walk out with bedroom/workout/office/hangout/whatever you want room, Full Bath and Storage Room. Great Setting! So many possibilities. Soak in the Hot Tub and entertain with the screened in porch. Do Not Wait on this one. Make your appointment today!