Recently Sold Homes in 21550, MD

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SOLD NOV 24, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Welcome to 202 Penelacre Lane – a rare opportunity to own 97 feet of serene lakefront on one of Deep Creek Lake’s most sought-after roads. Nestled on a flat, easily accessible lot, this 3-bedroom, 2-bathroom home offers effortless one-level living and a front-row seat to Western Maryland’s four-season beauty along with a Type-A dock permit. Inside, you’ll find a spacious open-concept kitchen, dining, and family room area that’s perfect for entertaining or cozy nights in. Wake up to the peaceful sounds from the lake with your private lakefront sunroom — an ideal spot for your morning coffee or a relaxing evening with friends. A detached two-car garage adds

$975,000 Last sold price

3 beds2 baths1,648 sq ft

202 Penelacre Ln, Oakland, MD 21550

(301) 387-2000

SOLD NOV 10, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Don't miss this incredible opportunity to own a 3-bedroom, 2-bath home nestled on a spacious, wooded lot. Located in the serene lake-access community of Paradise Gardens, this property includes a dedicated dock slip, making it perfect for boating enthusiasts and lake lovers alike. Enjoy the great outdoors with expansive decks ideal for entertaining, relaxing, or taking in the tranquil wooded surroundings. Gather around the fire pit on cool evenings and create lasting memories with friends and family. Inside, cozy up tothe wood burning fireplace after a day summer or winter time fun . Downstairs the unfinished basement offers a blank canvas for future expansion — whether you're dreami

$558,000 Last sold price

3 beds2 baths2,176 sq ft

72 Cliff Dr, Oakland, MD 21550

(301) 387-2000

SOLD NOV 25, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Iconic Lakeside Mountain Retreat at Deep Creek Lake! Recently Renovated, This 6 Bedroom 5.5 Bath Rental Goliath features a shiny new gourmet kitchen, updated bathrooms, several new mini split systems, a new hot tub, updated furnishings, a fresh coat of exterior stain, and new floors throughout. Complete facelift of the outdoor living space with sprawling new treks deck, fire pit, and concrete retaining wall. Multiple living/entertaining spaces, along with 3 true ensuites equipped with updated treks balconies. Boasting 7700 sq. ft, this house includes a 13-seat 150" Home Theater, indoor pool, several stacked stone fireplaces, and 3 stories of outdoor living space with a tube slide! Unde

$1,950,000 Last sold price

6 beds5.5 baths5,389 sq ft

2463 Mayhew Inn Rd, Oakland, MD 21550

(301) 387-2000

SOLD SEP 26, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Experience lakefront living at its finest with this beautifully updated 2-level condo on the shores of Deep Creek Lake. Unit G509 features 2 bedrooms and 1 full bathroom, offering breathtaking lake views. The main level includes a well-appointed kitchen and a cozy living area complete with a wood-burning fireplace—perfect for year-round relaxation. Upstairs, you’ll find two spacious bedrooms with new carpeting and a renovated bathroom featuring a walk-in shower. Enjoy exclusive community amenities including an indoor swimming pool, fitness center, lakefront beach, and potential boat slip access through the association. Just steps away are popular dining options like Ace’s

$380,000 Last sold price

2 beds1 bath640 sq ft

20160 Garrett Hwy Unit G509, Oakland, MD 21550

(301) 387-4700

SOLD OCT 3, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Escape to your ideal mountain-lake retreat at Deep Creek Lake with this charming chalet-style home, nestled in a peaceful, wooded setting. This warm and inviting 3-bedroom, 2-bath getaway blends rustic charm with modern comfort—perfect as a vacation home or full-time residence. Take in filtered lake views from your home and expansive deck or relax by the lake with exclusive access to a sandy beach. Enjoy the use of a boat slip on a rotational basis. With 1/10 undivided ownership of this beautifully maintained lakeside parcel, you’ll have secure and shared enjoyment of a premium waterfront experience—excellent for swimming, sunbathing, kayaking, and boating. Inside, a spaci

$530,000 Last sold price

3 beds2 baths1,800 sq ft

346 Skippers Point Rd, Oakland, MD 21550

(301) 387-2000

Property at 473 Cumberland Rd, Oakland, MD 21550, 3 beds, 2 baths

$285,000 Last sold price

3 beds2 baths1,389 sq ft

473 Cumberland Rd, Oakland, MD 21550

(410) 486-4504

Property at 3273 Lake Shore Dr, Oakland, MD 21550, 6 beds, 3 baths

$1,270,000 Last sold price

6 beds3 baths1,714 sq ft

3273 Lake Shore Dr, Oakland, MD 21550

(301) 387-4700

Property at 1989 Lake Shore Dr, Oakland, MD 21550, 4 beds, 3.5 baths

$1,400,000 Last sold price

4 beds3.5 baths3,008 sq ft

1989 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 20160 Garrett Hwy Unit D310, Oakland, MD 21550, 2 beds, 2 baths

$485,000 Last sold price

2 beds2 baths1,379 sq ft

20160 Garrett Hwy Unit D310, Oakland, MD 21550

(703) 831-6806

Property at 1087 Pergin Farm Rd, Oakland, MD 21550, 6 beds, 5.5 baths

$2,975,000 Last sold price

6 beds5.5 baths4,481 sq ft

1087 Pergin Farm Rd, Oakland, MD 21550

(301) 387-2000

Property at 531 S 3rd St, Oakland, MD 21550, 5 beds, 2.5 baths

$320,000 Last sold price

5 beds2.5 baths2,477 sq ft

531 S 3rd St, Oakland, MD 21550

(240) 801-5011

Property at 94 Meadow Ct, Oakland, MD 21550, 3 beds, 4 baths

$664,500 Last sold price

3 beds4 baths2,460 sq ft

94 Meadow Ct, Oakland, MD 21550

(301) 387-4700

Property at 1674 Paradise Point Rd, Oakland, MD 21550, 4 beds, 2.5 baths

$1,500,000 Last sold price

4 beds2.5 baths2,340 sq ft

1674 Paradise Point Rd, Oakland, MD 21550

(301) 387-2000

Property at 197 Black Angus Dr, Oakland, MD 21550, 5 beds, 3.5 baths

$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 113 G St, Oakland, MD 21550, 9 beds, 3.5 baths

$379,000 Last sold price

9 beds3.5 baths3,840 sq ft

113 G 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 607 K, Oakland, MD 21550, 4 beds, 2 baths

$115,000 Last sold price

4 beds2 baths1,332 sq ft

607 K, Oakland, MD 21550

(301) 387-4700

Property at 306 Shady Acre Ln, Oakland, MD 21550, 4 beds, 3 baths

$165,000 Last sold price

4 beds3 baths2,288 sq ft

306 Shady Acre Ln, Oakland, MD 21550

(866) 525-3466

Property at 170 Tannery Rd, Oakland, MD 21550, 3 beds, 2 baths

$174,500 Last sold price

3 beds2 baths1,850 sq ft

170 Tannery Rd, Oakland, MD 21550

(888) 400-2513

Property at 105 Main St, Oakland, MD 21550, 3 beds, 1.5 baths

$134,000 Last sold price

3 beds1.5 baths1,466 sq ft

105 Main St, Oakland, MD 21550

(301) 387-4700

Property at 247 Winding Trail Ln Unit 6B, Oakland, MD 21550, 5 beds, 4.5 baths

$554,999 Last sold price

5 beds4.5 baths3,300 sq ft

247 Winding Trail Ln Unit 6B, 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 273 Glendale Rd, Oakland, MD 21550, 5 beds, 5.5 baths

$2,450,000 Last sold price

5 beds5.5 baths5,141 sq ft

273 Glendale Rd, Oakland, MD 21550

(301) 387-4700

Property at 1931 Lake Shore Dr, Oakland, MD 21550, 5 beds, 5.5 baths

$3,000,000 Last sold price

5 beds5.5 baths5,100 sq ft

1931 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 150 Greenbrier Dr, Mc Henry, MD 21541, 5 beds, 5.5 baths

$875,000 Last sold price

5 beds5.5 baths4,345 sq ft

150 Greenbrier Dr, Mc Henry, MD 21541

(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 20676 Garrett Hwy, Oakland, MD 21550, 5 beds, 4.5 baths

$1,425,000 Last sold price

5 beds4.5 baths2,280 sq ft

20676 Garrett Hwy, Oakland, MD 21550

(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 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 102 Mountainview Ct, Oakland, MD 21550, 7 beds, 4.5 baths

$900,000 Last sold price

7 beds4.5 baths5,376 sq ft

102 Mountainview Ct, Oakland, MD 21550

(301) 387-2000

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 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 50 Village Dr #7, Oakland, MD 21550, 2 beds, 2 baths

$459,000 Last sold price

2 beds2 baths1,008 sq ft

50 Village Dr #7, Oakland, MD 21550

(301) 387-2000

Property at 873 Paradise Hts, Oakland, MD 21550, 5 beds, 4 baths

$780,000 Last sold price

5 beds4 baths2,934 sq ft

873 Paradise Hts, Oakland, MD 21550

(301) 387-2000

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 128 Big Bass Dr, Oakland, MD 21550, 5 beds, 3.5 baths

$1,445,000 Last sold price

5 beds3.5 baths4,305 sq ft

128 Big Bass Dr, Oakland, MD 21550

(301) 387-2000

Property at 20160 Garrett Hwy Unit D308/408, Oakland, MD 21550, 2 beds, 2 baths

$450,000 Last sold price

2 beds2 baths1,325 sq ft

20160 Garrett Hwy Unit D308/408, 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 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

$280,000

— beds— baths— sq ft

36 Laurel Brook Dr #36, Oakland, MD 21550

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Recently Sold Homes in 21550

There are currently 126 recently sold homes for sale in 21550 at a median listing price of $527K. 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 125 days. This map is refreshed with the newest listings in 21550 every 15 minutes.

In the past month, 24 homes have been sold in 21550. In addition to houses in 21550, there were also 13 condos, 6 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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