Recently Sold Homes in 21550, MD

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SOLD OCT 16, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Nestled on 100+/- feet of pristine Deep Creek Lake shoreline, this 6-bedroom, 3-bathroom cottage perfectly blends classic lakeside charm with modern comfort. Featuring a Type A dock, wood-burning stone fireplace, hardwood floors, tile bathrooms, and a remodeled kitchen with granite countertops and Bosch appliances, the home is designed for both relaxation and entertaining. Thoughtful custom touches throughout highlight the seller’s careful upgrades, including updated electrical, new heating and cooling, renovated bathrooms, and a new roof. A partially covered wraparound deck offers unobstructed lake views, making it the ideal spot for morning coffee or evening sunsets. Perfectly situa

$1,270,000 Last sold price

6 beds3 baths1,714 sq ft

3273 Lake Shore Dr, Oakland, MD 21550

(301) 387-4700

SOLD SEP 22, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
A unique opportunity to own a lakefront/ lake view 2-bedroom, 2-bath with a bonus room at Will O' The Wisp Prestige Condominiums, unit D310/410. The 'D” units are highly sought after as there are only 4 D units and this one offers a bonus room. The unit was remodeled with new drywall, new insulation was installed for heating and cooling efficiency. Upgrades are not just cosmetic and include an upgraded and expanded electrical system and plumbing, two water heaters, private WIFI/cable and 2 HVAC systems result in energy efficiency and lower electric bills. Owners replaced the top expansive windows in the main room with UV windows and added window film to the others, to keep the room co

$485,000 Last sold price

2 beds2 baths1,379 sq ft

20160 Garrett Hwy Unit D310, Oakland, MD 21550

(703) 831-6806

SOLD OCT 3, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Step into a home like no other—where architectural charm meets modern comfort, and lake views greet you from nearly every room. With six bedrooms and five-and-a-half baths, there’s space for everyone to relax in style. The open, light-filled main living area is anchored by a striking fireplace and a window-wrapped dining alcove with serene water views, while a wall of windows frames the gorgeous kitchen at one end. Off the open living/dining/kitchen area, you’ll find a second living space, perfect for intimate gatherings or quiet reading. The sunlit study is a dream, with floor-to-ceiling windows and skylights that bring the outdoors in. The spacious lakeside main-level pr

$2,975,000 Last sold price

6 beds5.5 baths4,481 sq ft

1087 Pergin Farm Rd, Oakland, MD 21550

(301) 387-2000

SOLD OCT 17, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Impressive lake-access home located in the desirable Paradise Ridge community. This modern retreat showcases breathtaking views of the mountains and Deep Creek Lake. From the moment you step inside, you'll be welcomed by a warm, inviting atmosphere featuring wood-accented ceilings, luxury vinyl plank flooring, quartz countertops, and an abundance of natural light through expansive windows. With three ensuite bedrooms and four full bathrooms, there’s ample space for hosting family and friends in comfort. Outdoor living is just as impressive, with a spacious wraparound deck, a covered side porch, and a lower-level patio—perfect for relaxing or entertaining. The large yard, paved d

$664,500 Last sold price

3 beds4 baths2,460 sq ft

94 Meadow Ct, Oakland, MD 21550

(301) 387-4700

SOLD OCT 20, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
A one of a kind lakefront retreat overlooking a beautiful cove in the peaceful Pergin Farm community at Deep Creek Lake. Situated at the end of a quiet lane, the completely updated 5 bedroom 4.5 bath cottage style home with 200' of prime frontage at the end of private lane. The impressive cottage style residence offers an inviting open main level living area with a fabulous kitchen, beautiful wood burning fireplace, 3 suites and direct access to an expansive deck with a hot tub that has been built into the deck surface. The lower level offers two additional suites and a relaxing lakeside family room. Enjoy the fire pit area overlooking the beautiful cove or take a walk on over 3 miles of pr

$2,600,000 Last sold price

5 beds3.5 baths4,156 sq ft

197 Black Angus Dr, Oakland, MD 21550

(301) 387-2000

Property at 462 Skippers Point Rd, Oakland, MD 21550, 5 beds, 2 baths

$490,000 Last sold price

5 beds2 baths1,620 sq ft

462 Skippers Point Rd, Oakland, MD 21550

(301) 387-2000

Property at 414 D St, Oakland, MD 21550, 2 beds, 1 bath

$150,000 Last sold price

2 beds1 bath936 sq ft

414 D St, Oakland, MD 21550

(301) 387-4700

Property at 1101 Wheeling Ave, Oakland, MD 21550, 3 beds, 2 baths

$85,000 Last sold price

3 beds2 baths1,718 sq ft

1101 Wheeling Ave, Oakland, MD 21550

(301) 249-1600

Property at 500 Seneca Ave, Oakland, MD 21550, 3 beds, 1 bath

$62,000 Last sold price

3 beds1 bath1,284 sq ft

500 Seneca Ave, Oakland, MD 21550

(301) 334-5757

Property at 343 Maple Del Ln, Oakland, MD 21550, 3 beds, 2.5 baths

$405,000 Last sold price

3 beds2.5 baths1,404 sq ft

343 Maple Del Ln, Oakland, MD 21550

(301) 387-2000

Property at 2360 Garrett Rd, Oakland, MD 21550, 2 beds, 1 bath

$285,000 Last sold price

2 beds1 bath1,050 sq ft

2360 Garrett Rd, Oakland, MD 21550

(301) 387-2000

Property at 290 Crellin Underwood Rd, Oakland, MD 21550, 3 beds, 2 baths

$280,500 Last sold price

3 beds2 baths2,208 sq ft

290 Crellin Underwood Rd, Oakland, MD 21550

(301) 387-2000

Property at 4643 Oakland Sang Run Rd, Oakland, MD 21550, 2 beds, 2 baths

$180,000 Last sold price

2 beds2 baths864 sq ft

4643 Oakland Sang Run Rd, Oakland, MD 21550

(301) 387-2000

Property at 4960 Hutton Rd, Oakland, MD 21550, 2 beds, 1 bath

$139,000 Last sold price

2 beds1 bath1,080 sq ft

4960 Hutton Rd, Oakland, MD 21550

(301) 387-2000

Property at 5154 Maryland Hwy, Oakland, MD 21550, 5 beds, 2 baths

$375,000 Last sold price

5 beds2 baths2,860 sq ft

5154 Maryland Hwy, Oakland, MD 21550

(301) 387-8300

Property at 4012 Maryland Hwy, Oakland, MD 21550, 3 beds, 1 bath

$280,000 Last sold price

3 beds1 bath1,824 sq ft

4012 Maryland Hwy, Oakland, MD 21550

(301) 387-2000

Property at 180 Mystic Creek Trl Unit 3A, Oakland, MD 21550, 3 beds, 3.5 baths

$460,000 Last sold price

3 beds3.5 baths2,200 sq ft

180 Mystic Creek Trl Unit 3A, Oakland, MD 21550

(301) 387-2000

Property at 502 E Oak St, Oakland, MD 21550, 3 beds, 2 baths

$239,900 Last sold price

3 beds2 baths1,680 sq ft

502 E Oak St, Oakland, MD 21550

(301) 387-2000

Property at 1589 Lake Shore Dr, Oakland, MD 21550, 3 beds, 3 baths

$1,399,000 Last sold price

3 beds3 baths1,872 sq ft

1589 Lake Shore Dr, Oakland, MD 21550

(301) 387-4700

Property at 41 Sandstone Cir, Mc Henry, MD 21541, 4 beds, 3 baths

$690,000 Last sold price

4 beds3 baths1,716 sq ft

41 Sandstone Cir, Mc Henry, MD 21541

(301) 387-2000

Property at 1473 Pergin Farm Rd, Oakland, MD 21550, 4 beds, 2 baths

$925,000 Last sold price

4 beds2 baths2,230 sq ft

1473 Pergin Farm Rd, Oakland, MD 21550

(410) 529-1900

Property at 216 Tarn Dr, Oakland, MD 21550, 6 beds, 4.5 baths

$1,100,000 Last sold price

6 beds4.5 baths4,769 sq ft

216 Tarn Dr, Oakland, MD 21550

(301) 387-4700

Property at 320 Coolidge Ave, Oakland, MD 21550, 2 beds, 1 bath

$135,000 Last sold price

2 beds1 bath720 sq ft

320 Coolidge Ave, Oakland, MD 21550

(301) 387-2000

Property at 83 Boston Post Rd, Oakland, MD 21550, 1 bed, 1 bath

$247,500 Last sold price

1 bed1 bath400 sq ft

83 Boston Post Rd, Oakland, MD 21550

(301) 387-2000

Property at 612 Harvey Winters Dr, Oakland, MD 21550, 4 beds, 3 baths

$465,000 Last sold price

4 beds3 baths2,473 sq ft

612 Harvey Winters Dr, Oakland, MD 21550

(301) 387-2000

Property at 307 Winding Trail Ln Unit 12B, Oakland, MD 21550, 5 beds, 4.5 baths

$587,500 Last sold price

5 beds4.5 baths3,300 sq ft

307 Winding Trail Ln Unit 12B, Oakland, MD 21550

(301) 387-2000

Property at 181 Grand Estates Dr, Mc Henry, MD 21541, 4 beds, 2.5 baths

$660,000 Last sold price

4 beds2.5 baths2,640 sq ft

181 Grand Estates Dr, Mc Henry, MD 21541

(301) 387-4700

Property at 722 Winding Estates Dr, Mc Henry, MD 21541, 4 beds, 2.5 baths

$770,000 Last sold price

4 beds2.5 baths2,962 sq ft

722 Winding Estates Dr, Mc Henry, MD 21541

(301) 387-2000

Property at 1419 Sandy Shores Rd, Mc Henry, MD 21541, 5 beds, 5 baths

$1,525,000 Last sold price

5 beds5 baths3,696 sq ft

1419 Sandy Shores Rd, Mc Henry, MD 21541

(301) 387-2000

Property at 2805 Shady Dell Rd, Oakland, MD 21550, 4 beds, 2 baths

$208,550 Last sold price

4 beds2 baths1,456 sq ft

2805 Shady Dell Rd, Oakland, MD 21550

(301) 387-4700

Property at 267 Woodlands Hill Ln, Oakland, MD 21550, 4 beds, 3.5 baths

$975,000 Last sold price

4 beds3.5 baths2,232 sq ft

267 Woodlands Hill Ln, Oakland, MD 21550

(301) 387-2000

Property at 2045 Swallow Falls Rd, Oakland, MD 21550, 5 beds, 3.5 baths

$910,000 Last sold price

5 beds3.5 baths5,416 sq ft

2045 Swallow Falls Rd, Oakland, MD 21550

(301) 387-2000

Property at 200 Lake Shore Dr, Oakland, MD 21550, 4 beds, 3.5 baths

$745,000 Last sold price

4 beds3.5 baths2,559 sq ft

200 Lake Shore Dr, Oakland, MD 21550

(888) 400-2513

Property at 118 Roman Ridge Rd, Oakland, MD 21550, 3 beds, 3.5 baths

$485,000 Last sold price

3 beds3.5 baths1,820 sq ft

118 Roman Ridge Rd, Oakland, MD 21550

(443) 574-1600

$420,000

— beds2 baths2,752 sq ft

425 E Alder St, Oakland, MD 21550

$190,000

— beds2 baths1,252 sq ft

220 N 12th St, Oakland, MD 21550

$1,525,000

— beds5 baths3,696 sq ft

1419 Sandy Shores Rd, Mc Henry, MD 21541

$100,000

— beds1 bath1,126 sq ft

1705 Paradise Point Rd, Oakland, MD 21550

$270,000

— beds2 baths960 sq ft

29 Sloan Tract Rd, Oakland, MD 21550

$216,900

— beds3 baths1,800 sq ft

705 Pensinger Blvd, Oakland, MD 21550

$200,000

— beds1 bath1,232 sq ft

3855 Hutton Rd, Oakland, MD 21550

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Recently Sold Homes in 21550

There are currently 115 recently sold homes for sale in 21550 at a median listing price of $530K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21550 stay on the market for 109 days. This map is refreshed with the newest listings in 21550 every 15 minutes.

In the past month, 25 homes have been sold in 21550. In addition to houses in 21550, there were also 14 condos, 18 townhouses, and 1 multi-family unit for sale in 21550 last month. Find your dream home in 21550 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21550 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21550. If you're looking to sell your home in the 21550 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21550 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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