21550 Real Estate Search

21550 Homes with a Pool for Sale

The real estate market around the 21550 area offers a diverse selection of homes with pools, catering to a variety of lifestyles and preferences. Buyers can find properties ranging from charming single-family homes to luxurious estates, each featuring private swimming pools that provide a perfect retreat for relaxation and entertainment. The availability of these homes not only enhances the outdoor living experience but also adds considerable appeal for families and individuals looking for a slice of luxury. With local amenities, parks, and recreational areas nearby, this region presents a wonderful opportunity for those seeking to enjoy a vibrant community while indulging in the comfort of their own backyard oasis.

Our website features the best real estate search for homes with a pool available in 21550 and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest 21550 Homes with a Pool for Sale

$539,000
3 Beds ⋅ 3 Baths
Discover this charming cabin-style home located just 5 minutes from Deep Creek Lake. This 3-bedroom, 2.5 bathroom home offers a perfect blend of comfort and outdoor enjoyment. Step in to an open concept main level with vaulted ceilings and wood finished throughout. A wood-burning fireplace adds warmth and character to the living area, creating an inviting atmosphere for gatherings.The fully finished basement provides additional living space, perfect for entertaining or relaxation. Step outside to enjoy your own personal pool. Situated on a 4.96-acre lot a detached 3 car, 2 story garage and work space. This home combines the charm of a lodge-style retreat with modern amenities, making it an excellent choice for anyone looking to embrace a lifestyle centered around relaxation and recreation. Don't miss the opportunity to make this unique property your own!

5847 Bittinger Rd, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

$395,000
3 Beds ⋅ 1 Baths
Nestled on nearly 5 acres of serene landscape, this charming farmhouse-style home offers a perfect blend of rustic charm and modern comfort. With 1,800 square feet of living space, this residence features three cozy bedrooms and a well-appointed full bathroom, making it an ideal retreat for those seeking tranquility and space. Step inside to discover a warm and inviting interior, where traditional design meets contemporary convenience. The combination kitchen and dining area is perfect for gatherings, featuring a country-style kitchen. Natural light pours in through insulated windows, enhancing the inviting ambiance throughout the home. The living spaces are adorned with a mix of hardwood, carpet, and vinyl flooring, providing both comfort and style. Ceiling fans in key areas ensure a pleasant airflow, making every corner of the home feel just right. The traditional floor plan allows for easy movement between rooms, making daily living a breeze. Step outside to your own personal oasis, where a heated in-ground pool awaits, perfect for summer relaxation and fun. The expansive outdoor space includes a deck and patio, ideal for hosting barbecues or enjoying quiet evenings under the stars. Invite family and friends over to enjoy the in ground pool! Additional structures on the property, such as a gazebo, machine shed, and greenhouse, provide ample storage and opportunities for gardening enthusiasts. Parking is a breeze with a spacious attached garage that accommodates up to three vehicles, along with additional driveway space for guests. The asphalt driveway leads you home, ensuring easy access year-round. This property is not just a house; it's a place where memories are made. Whether you're looking to unwind in your private retreat or entertain loved ones, this home offers the perfect backdrop for a fulfilling lifestyle. Embrace the charm and comfort of country living while enjoying the conveniences of modern amenities. Your dream home awaits!

265 Fearer Rd, Friendsville

Listing courtesy of Railey Realty, Inc.. Contact:

$3,950,000
8 Beds ⋅ 10 Baths
Experience exceptional lakefront living in this spectacular eight-bedroom estate designed for unforgettable gatherings and year-round enjoyment. Perfectly positioned on an oversized lakefront lot with 116’ LF, this remarkable home offers easy access to the water via a walking path, and the abundance of windows fill the interior with natural light. At the heart of the home is a magnificent great room with soaring ceilings, creating an impressive space for entertaining family and friends. The gourmet kitchen is a chef's dream, featuring premium finishes, generous prep space, and abundant cabinetry, making it as functional as it is beautiful. Boasting an indoor sparkling pool and sauna right off the lower-level family room, along with a full kitchen and a playroom. Then step outside to your private lakeside retreat, complete with two relaxing hot tubs, a fire pit area, a sports court in the front, and spacious outdoor living areas ideal for dining, entertaining, or simply soaking in the peaceful surroundings. With eight spacious en-suite bedrooms, there is ample room for guests, making this an exceptional primary residence, vacation home, or luxury rental opportunity “The Haven”. Offering the perfect blend of elegance, comfort, and resort-style amenities, this extraordinary waterfront property is a rare opportunity to own the ultimate lakefront lifestyle.

1131 Lake Shore Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$3,299,900
8 Beds ⋅ 9 Baths
Luxury Lakefront wth a Dock Slip at Deep Creek Lake - Experience refined lake living at 14 Stillwater Drive, an exceptional modern home in the desirable Stillwater Community offering luxury, comfort, and spectacular lake views. On nearly 3/4 acres of lakefront mountain pasture, this 8-bed, 8.5 Bath boasts almost 9000 sq ft of finished living space. Inside, soaring ceilings and expansive windows fill the home with natural light, while a dramatic floor-to-ceiling stone fireplace creates a striking focal point in the main living area. The spacious open floor plan is ideal for both everyday living and entertaining, with a well-appointed gourmet kitchen, flowing seamlessly into the dining and great room. Indoor pool for year-round enjoyment. The lower level features a sprawling rec room with multiple game tables, wet-bar, and private theater room. 6 en suites with two overlooking the lake from their private balconies. Outside is the beautiful lakeside patio, the perfect place to relax, entertain, soak in the hot tub, or take in the peaceful surroundings and panoramic water views and abundant wildlife, including deer, beavers, turtles, geese, and eagles! Self-sufficient with a whole-house generator, several zoned HVAC system, and full water treatment complete with UV light. With the recently added sprinkler system, "Castle on the Cove" is rent-ready and sure to become one of Deep Creek Lake's premier vacation rentals. Combining timeless craftsmanship, resort-style amenities, and an unbeatable setting, this one-of-a-kind home offers an exceptional lifestyle inside and out. Don’t miss your chance to see this remarkable Deep Creek classic… Call today to schedule your private showing!

14 Stilwater Dr, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

$899,000
6 Beds ⋅ 5 Baths
Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy. Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and expansive windows that fill the home with natural light while showcasing the serene surroundings. The beautifully updated kitchen is designed for gathering, featuring granite countertops, abundant cabinetry, stainless steel appliances, and a spacious island that flows seamlessly into the dining and living areas. With six generously sized bedrooms and four-and-a-half baths, there's room for everyone to relax in comfort. Thoughtful upgrades throughout the home provide a fresh, modern feel while maintaining the warmth and character of this impressive property. Outside, your own private retreat awaits. Spend summer days enjoying the heated in-ground swimming pool, entertain on the expansive rear deck, or simply unwind while taking in the views of the park-like backyard. The sprawling acreage offers plenty of room for recreation, gardening, or simply enjoying the beauty of nature. Completing the property is a 3-car attached garage, offering ample space for vehicles, outdoor gear, and storage. Conveniently located just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and Oakland's historic downtown, this remarkable home delivers the perfect balance of luxury, convenience, and country living. Whether you're searching for a full-time residence or a private retreat near Maryland's premier four-season destination, this extraordinary property is one you won't want to miss. *$5,000 buyer credit for carpeting with accepted offer*

17240 Garrett Hwy, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,799,900
6 Beds ⋅ 8 Baths
Sunset Serenity is a newly constructed luxury mountain retreat completed in 2026, offering an exceptional blend of modern design, upscale amenities, and year-round recreation in the heart of Deep Creek Lake. This expansive residence features 6 bedrooms, 6 full bathrooms, 2 half bathrooms, and is thoughtfully designed to accommodate large gatherings while maintaining comfort and privacy throughout. The home's striking architecture is highlighted by soaring ceilings, oversized windows, and an open-concept floor plan that fills the interior with natural light. The spacious great room flows seamlessly into a chef-inspired kitchen featuring premium finishes, abundant cabinetry, and generous dining space ideal for entertaining. Designed with recreation and relaxation in mind, the property showcases a rare private indoor swimming pool, creating a true four-season resort experience. Additional entertainment space includes a game room and multiple gathering areas throughout the home. Outdoor living is equally impressive, with expansive covered decking with plenty of entertainment space, and a hot tub positioned to enjoy the peaceful wooded surroundings. Whether hosting guests or unwinding after a day of outdoor adventure, the setting offers the perfect balance of privacy and luxury. Ideally situated less than a mile from Lodestone Golf Course, and minutes from Deep Creek Lake—the property provides convenient access to boating, skiing, hiking, golf, restaurants, breweries, and countless year-round opportunities. The location, combined with the home's premium amenities and spacious layout, makes Sunset Serenity a rare and unique opportunity to to own a private mountain retreat, with all the stylish modern comforts of home!

49 Greenstone Way, Mc Henry

Listing courtesy of Railey Realty, Inc.. Contact:

$5,250,000
5 Beds ⋅ 7 Baths
Welcome to "Stone Manor", one of Deep Creek Lake's most extraordinary waterfront estates. Custom built in 2023 by renowned builder Don Nemith and beautifully curated by Juniper Interiors, this remarkable lakefront retreat blends timeless craftsmanship, luxury design, and exceptional investment potential. Situated on nearly an acre with 108.9 feet of level lake frontage and a coveted Class A private dock, the property offers over 8,300 square feet of thoughtfully designed living space in one of Deep Creek Lake's most desirable locations. Paying homage to the property's rich history, the owners incorporated stone from the original Stone Manor into the construction and landscape design, creating a one-of-a-kind residence that honors the past while delivering every modern luxury imaginable. Inside, you'll find 5 bedrooms, 6 full baths, 1 half bath, soaring ceilings, expansive gathering spaces, designer finishes, and walls of glass that frame breathtaking lake views throughout the home. The spectacular indoor pool creates a true four-season resort experience, while multiple indoor and outdoor entertaining areas were designed for unforgettable gatherings with family and friends. The exterior is equally impressive, featuring extensive custom hardscaping, an outdoor kitchen, multiple lakeside entertaining spaces, and easy access to the private dock just steps from the home. A massive 4-car garage provides exceptional space for vehicles, boats, lake toys, and storage. Currently operating as the highly successful Stone Manor vacation rental, the property has generated an average of $201,000 in annual gross rental revenue, offering established income potential alongside luxury lakefront ownership. One of the few newer luxury homes on Deep Creek Lake offering a Class A dock, indoor pool, and proven six-figure rental history, Stone Manor presents a rare opportunity to own a private waterfront resort in the heart of Deep Creek Lake. Conveniently located just minutes from Wisp Resort, golf, marinas, restaurants, and year-round recreation. Offered fully furnished and turnkey. Shown by appointment only. Call today for your private tour.

230 Rock Lodge Rd, Mc Henry

Listing courtesy of The KW Collective. Contact: 4435741600
$794,500
4 Beds ⋅ 3 Baths
Recently updated in 2021, this home features modern finishes, premium hardwood floors, and upgraded systems throughout. This home has never been rented but is projected to do just under $90k a year! Fully finished rec room with kitchenette above the garage that the buyers can use however they wish! Located next to Wisp Resort and Fantasy Valley golf course, this property is just minutes from everything Deep Creek Lake has to offer! Step into your private oasis featuring an incredible outdoor patio with a luxurious saltwater pool. The patio is complete with a hot tub, a wood burning fireplace, outdoor bar, and plenty of lounge seating. It's resort style living right in your own backyard. The main house is 4 bedrooms and 3 full bathrooms with just under 3,000 square feet of living space. The kitchen features top-of-the-line appliances, custom cabinetry, and an island perfect for setting up food. Designed for both style and function, it’s a chef’s dream—where gourmet meals and everyday living come together effortlessly. The primary bedroom features a hot tub on the balcony, perfect for a relaxing movie night. All bathrooms have been beautifully updated and appointed. Downstairs is the perfect place to enjoy any sports game. There is a game table, pool table and a second living room perfect for game night! The massive 38ftx50ft (2,272 sq ft) heated garage offers so much space for storage or a workstation with an apartment/in-law suite above. The sellers currently have the space above the garage setup as a 3 bedroom and 1 full bathroom. This property is located outside of zoning, so the new owner can decide what they wish to do with this amazing space! Please contact me today to schedule a private tour of this McHenry oasis! This property features a video and audio security system.

2250 Hoyes Run Rd, Mc Henry

Listing courtesy of Railey Realty, Inc.. Contact:

$1,500,000
5 Beds ⋅ 6 Baths
Private Indoor Pool on Lakefront Links — Deeded Slip, Five En Suites, Four-Season Deep Creek Living Rare on Deep Creek Lake: your own private indoor pool. Set on coveted Lakefront Links Drive in the Waterfront Greens community, this five-en-suite retreat delivers what almost nothing else on the market can — true four-season enjoyment. Swim laps in the sun-room pool while snow falls on the slopes at Wisp, then warm up by the fire after a day on the water. Inside, an open living-dining-kitchen with granite counters flows to expansive lake views, and each of the five bedrooms has its own full bath — ideal for hosting family and friends with room for everyone to spread out. A dedicated dock slip puts you on the water for boating, waterskiing, fishing, and kayaking all summer long. Waterfront Greens surrounds you with amenities most lake homes can’t match: a par-3 nine-hole golf course, tennis courts, mini golf, a catch-and-release fishing pond, and a community clubhouse — minutes from Wisp Resort, restaurants, and shopping. Offered turn-key as an established vacation rental, this is a lifestyle home that works just as hard as an investment. Comparable slip homes on this street are asking well into the $1.8M–$1.9M range — this is your opportunity to own the one with the private indoor pool, at a fraction of the cost.

342 Lakefront Links Dr, Swanton

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$1,899,900
5 Beds ⋅ 5 Baths
Lakefront Craftsman in one of Deep Creek Lake's finest communities. This 5-bed 5-bath home directly adjoins Deep Creek Lake with 100 ft of frontage and your very own boat slip. Clean, contemporary build with 3,788 finished sqft on 0.86 acres. Recently updated with new flooring, modern kitchen, bathroom vanities and rustic timber accents. Open main level with cathedral ceilings, hardwood floors, wood-burning fireplace, and a quartzite-topped kitchen with island and breakfast bar. Main-level primary suite plus two additional ensuite bedrooms. The walkout lower level adds a second living space with a gameroom, gas fireplace, and wet bar. The attached Indoor pool with a brand new liner sets this one apart. EV Charger included. Outdoor living includes a hot tub, fire pit, and a level yard at the water’s edge. Wraparound and screened decking to take in the lake views. An established rental, "Stilwater Serenity" makes an excellent private mountain/lake retreat or something that helps pay for itself when you're not using it. Call today for details!

200 Stilwater Dr, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

$1,649,000
7 Beds ⋅ 6 Baths
Experience elevated living in this luxury contemporary home. Built in 2023, this was thoughtfully designed for both relaxation and entertainment. Boasting 7 spacious bedrooms and 6 beautifully appointed bathrooms, this turnkey property comes fully furnished and ready for immediate enjoyment or continued rental success. With an established rental history exceeding $100K annually, this home presents an outstanding investment opportunity as well as a luxurious retreat. To provide the best experience for their guests, the owners have added an additional $95K in upgrades & improvements. The open concept layout showcases a gourmet kitchen with high-end finishes, seamlessly flowing into expansive living and dining areas accented by two cozy fireplaces. Designed for year-round enjoyment, the home features a private indoor pool, a 10 seat state-of-the-art home theatre and a fully equipped game room-perfect for hosting guests or creating unforgettable family memories. Step outside to enjoy easy access to the par 3 golf course or spend some quiet time paddling your canoe or kayak at the lakefront of Deep Creek Lake. Relax on the large deck providing comfortable living room style seating with oversized hot tub and gather around the cozy fire pit area during cooler Garrett County evenings. This private community offers multiple other amenities for fun to include a clubhouse, tennis courts , picklebalI and mini-golf. Ideally located near popular area attractions, you will have both convenience and easy year round access for all things fun at Deep Creek!

619 Waterfront Greens Dr, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

$1,699,900
7 Beds ⋅ 6 Baths
Finished in the summer of 2025, “Grey Haven” is sure to become one of the top income-producing properties in the Deep Creek Lake area! This 7-bedroom, 5-bath luxury retreat features a spacious open-concept design that blends modern comfort with timeless mountain charm. Signature amenities include a private indoor pool, an 8-foot hot tub , an expansive deck, and a custom home theater. Adding a unique character, the living room is anchored by a one-of-a-kind chandelier crafted from a locally made 1960’s canoe. Designed with sustainability in mind, Grey Haven is an exceptionally “green” home. Constructed with an ICF foundation and top-grade insulation, it uses no carbon fuels for heating or cooling. Instead, it features advanced heat pump technology, all-electric appliances, dual EV chargers, and a restored vintage Malm wood-burning fireplace—delivering eco-conscious efficiency with average utility costs under $300 per month, even with heating the pool! Additional upgrades include $10,000 in custom window treatments throughout, a full sprinkler and alarm system, and a TVRU/rental license in place, making this a true turn-key opportunity. Located just minutes from Wisp Resort, marinas, restaurants, and year-round recreation, Grey Haven is the ultimate mountain escape—whether for private enjoyment or as a high-performing vacation rental property. Call today for details!

2614 Marsh Hill Rd, Mc Henry

Listing courtesy of Railey Realty, Inc.. Contact:

$1,299,000
5 Beds ⋅ 6 Baths
This stunning log home near Wisp Resort offers a luxurious retreat with seasonal views, an indoor pool house and plenty of space for indoor and outdoor living. Five-bedroom, five-and-a-half-bath masterpiece is designed for both relaxation and entertainment. Step inside to discover an open floor plan adorned with exposed beams and rich wood floors. The gourmet kitchen, equipped with high-end appliances including a built-in microwave, wall oven, and cooktop, flows effortlessly into the dining and living areas, perfect for hosting gatherings. Cozy up by one of the two stunning stone fireplaces, or unwind in the fully finished walkout basement, which offers additional living space and direct access to the outdoors. Outside, indulge in your own private oasis featuring a newly upgraded fire pit area overlooking the private 1.46 acre wooded lot. Enjoy breathtaking mountain views and seasonal lake views from the expansive deck or patio, ideal for alfresco dining or morning coffee. Renters and primary residents alike will both love the indoor pool house to enjoy year-round. Property offers a strong rental history! With Deep Creek Lake, andWISP Ski area just moments away, outdoor enthusiasts will appreciate year round activities. This property is not just a home; it's a lifestyle of luxury, comfort, and natural beauty. Experience the perfect blend of tranquility and sophistication in this remarkable residence. Fairly rental projection of $98k annually.

615 Sandy Shores Rd, Mc Henry

Listing courtesy of Railey Realty, Inc.. Contact:

$684,000
3 Beds ⋅ 4 Baths
Luxury Mountaintop Ski Chalet with scenic Deep Creek Lake Access for year-round enjoyment. Just minutes from Wisp's ski slopes and ASCI Whitewater, this fantastic location is ideal for exciting summer adventures and winter skiing with effortless connections to the Ski Lodge, easy-access mountaintop ski parking, lift tickets, on-site community amenities, and everything you need. Exceptional craftsmanship and upscale finishes shine throughout this home's bright, open layout designed for entertaining. Unwind by the striking stone fireplace in the inviting living room, while a generous family room and sunlit, flexible loft provide ideal spaces for entertaining, relaxing, or hosting guests. Three bedrooms and 3.5 baths across three beautifully designed levels deliver comfort, privacy, and room to gather. A convenient double carport adds everyday ease for owners and visitors alike. Surrounded by lush, thoughtfully landscaped trees, the setting offers a quiet mountain ambiance with filtered woodland views and a true resort feel. Designed for four-season mountain living, this home offers a high-efficiency HVAC system, architecturally enhanced cylindrical exterior columns, and tastefully updated interior and exterior paint—combining luxury aesthetics with resort-level performance. The home has been carefully maintained over time, reflecting pride of ownership and presenting with the feel often associated with well cared for owner-occupied properties. You'll love the Deep Creek Highlands community, featuring private lakefront access, scenic walking trails, sports courts, playground, and a resort-style outdoor pool with pavilion—ideal for both active adventures and laid-back mountain living. From first tracks at Wisp to summer days at the lake and championship golf at Lodestone, this prime location places every season’s adventure just minutes away, making it a rare and rewarding place to call home.

105 Mountain Overlook Court, Mc Henry

Listing courtesy of Railey Realty, Inc.. Contact:

$6,499,900
7 Beds ⋅ 9 Baths
Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with a sprawling island, Wolf range, and access to a four-season room that opens fully to the outdoors through custom bi-fold doors. The main-level primary suite spans nearly 900 sq ft with a private balcony, soaking tub, his-and-her vanities, and a massive walk-in closet. Enjoy five fireplaces, an indoor pool with fountains and a full bath, and three levels of outdoor living, including an outdoor kitchen, built-in hot tub with gazebo, outdoor shower, and deck drainage system to keep lower levels dry. Entertain with ease in the rec room with an industrial-style bar, climate-controlled wine cellar, and fully equipped gym. Three attached garages connect to a locker-style mudroom, with a lower-level garage ideal for a side-by-side or lake toys. Radiant heat, a whole-house generator, and three dock slips make this property as functional as it is flawless. A rare opportunity to own a true statement home in one of Deep Creek Lake’s most prestigious communities. Call today for your private tour!

47 Holy Cross, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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