Recently Sold Homes in 21550, MD

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SOLD OCT 15, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Discover Easy Like Sunday Morning, a stunning 4-bedroom, 3-bath log cabin perfectly placed in the heart of Deep Creek Lake. This inviting retreat combines rustic charm with fresh upgrades, including a newly finished lower level that expands the living space and adds a spacious fourth bedroom. Gather around the open living area with soaring ceilings, or step onto the oversized deck to soak in seasonal lake views. With plenty of parking and a central location close to Wisp Resort, state parks, restaurants, and nightlife, every adventure is just minutes away. Already a successful vacation rental with a proven history, this home offers both investment potential and the perfect mountain escape.

$711,000 Last sold price

4 beds3.5 baths2,556 sq ft

58 Glendale Woods Rd, Oakland, MD 21550

(301) 387-2000

SOLD SEP 2, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Welcome to this stunning 5-bedroom, 4.5-bathroom duplex-style home at Deep Creek Lake, offering the perfect blend of mountain charm, modern finishes, and exceptional rental potential. This meticulously maintained retreat spans three finished levels and boasts a spacious, professionally designed lower-level patio featuring a cozy fire pit, relaxing mountain views, and a brand-new 2024 hot tub—perfect for entertaining or unwinding after a day on the slopes or lake. Inside, the main level showcases an open-concept kitchen with granite countertops, stainless steel appliances, and a rustic shiplap accent wall that adds warmth and character. The inviting living area features a gas fireplace

$559,250 Last sold price

5 beds4.5 baths3,300 sq ft

285 Winding Trail Ln Unit 10A, Oakland, MD 21550

(301) 387-2000

SOLD SEP 25, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Welcome home to this recently renovated single-family ranch featuring 3 bedrooms, 1 bathroom, and approximately 1,500 sq ft of bright, single-level living. Timeless hardwood floors flow through an open, easy layout that's ideal for everyday life and effortless entertaining. New windows invite generous natural light throughout, and the refreshed kitchen with modern finishes anchors the heart of the home, offering plenty of room for meal prep and casual gathering. Set on a generous corner lot, the property provides space to garden, play, or unwind. A privacy fence along the back adds seclusion, perfect for pets, kids, and weekend get-togethers on the lawn. Tucked in a quiet, desirable neighbo

$279,000 Last sold price

3 beds1 bath1,518 sq ft

215 N 10th St, Oakland, MD 21550

(301) 334-8454

SOLD SEP 5, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
An extremely charming 3 bed 2 full bath home located on one of the most desired and convenient streets in Oakland and the gateway to the valley. This home has had recent tasteful upgrades and TLC making it move-in ready and with a sturdy oversized garage and partially fenced in side yard, the comforts of home are everywhere.

$275,000 Last sold price

3 beds2 baths1,488 sq ft

648 S 3rd St, Oakland, MD 21550

(301) 387-2000

SOLD SEP 26, 2025

ABOUT THIS HOME
Recently Sold Home in 21550, MD:
Affordable starter home on an alley in the town of Oakland with many possibilities. This rancher offers hardwood floors, newer roof , newer siding, covered porch and a full basement that can provide more living space. The natural gas heat is another plus. You are also within walking distance to many things in downtown Oakland.

$110,000 Last sold price

2 beds1 bath768 sq ft

110 W Pennington St, Oakland, MD 21550

(301) 387-4700

Property at 710 Hunters Ridge Dr, Oakland, MD 21550, 3 beds, 2 baths

$550,000 Last sold price

3 beds2 baths1,736 sq ft

710 Hunters Ridge Dr, Oakland, MD 21550

(301) 387-2000

Property at 723 E Oak St, Oakland, MD 21550, 3 beds, 1 bath

$132,000 Last sold price

3 beds1 bath988 sq ft

723 E Oak St, Oakland, MD 21550

(301) 387-2000

Property at 131 Rock Ridge Ln #12, Oakland, MD 21550, 4 beds, 3.5 baths

$495,000 Last sold price

4 beds3.5 baths2,422 sq ft

131 Rock Ridge Ln #12, Oakland, MD 21550

(301) 387-4700

Property at 416 Shenandoah Ave, Oakland, MD 21550, 3 beds, 1.5 baths

$157,000 Last sold price

3 beds1.5 baths975 sq ft

416 Shenandoah Ave, Oakland, MD 21550

(301) 387-2000

Property at 353 Basswood Way #24, Oakland, MD 21550, 4 beds, 3 baths

$695,000 Last sold price

4 beds3 baths2,664 sq ft

353 Basswood Way #24, Oakland, MD 21550

(301) 387-2000

Property at 237 Glendale Rd, Oakland, MD 21550, 7 beds, 6.5 baths

$1,860,000 Last sold price

7 beds6.5 baths3,735 sq ft

237 Glendale Rd, Oakland, MD 21550

(301) 387-2000

Property at 783 Mountainview Dr, Oakland, MD 21550, 3 beds, 3 baths

$420,000 Last sold price

3 beds3 baths1,971 sq ft

783 Mountainview Dr, Oakland, MD 21550

(301) 387-2000

Property at 10 Laurel Brook Dr #10, Oakland, MD 21550, 2 beds, 2 baths

$210,000 Last sold price

2 beds2 baths— sq ft

10 Laurel Brook Dr #10, Oakland, MD 21550

(410) 533-5486

Property at 122 Earl Hauser Rd, Oakland, MD 21550, 3 beds, 2 baths

$285,000 Last sold price

3 beds2 baths1,664 sq ft

122 Earl Hauser Rd, Oakland, MD 21550

(301) 387-2000

Property at 5 Laurel Brook Dr #5, Oakland, MD 21550, 2 beds, 2 baths

$187,500 Last sold price

2 beds2 baths1,400 sq ft

5 Laurel Brook Dr #5, Oakland, MD 21550

(410) 561-0044

Property at 2719 Broadford Rd, Oakland, MD 21550, 3 beds, 2.5 baths

$590,000 Last sold price

3 beds2.5 baths4,253 sq ft

2719 Broadford Rd, Oakland, MD 21550

(301) 387-2000

Property at 2571 Shady Dell Rd, Oakland, MD 21550, 2 beds, 2 baths

$200,000 Last sold price

2 beds2 baths1,678 sq ft

2571 Shady Dell Rd, Oakland, MD 21550

(301) 334-5757

Property at 220 N 11th St, Oakland, MD 21550, 4 beds, 2.5 baths

$370,000 Last sold price

4 beds2.5 baths3,159 sq ft

220 N 11th St, Oakland, MD 21550

(301) 387-2000

Property at 1220 Broadford Rd, Oakland, MD 21550, 4 beds, 2.5 baths

$365,000 Last sold price

4 beds2.5 baths2,092 sq ft

1220 Broadford Rd, Oakland, MD 21550

(301) 387-2000

Property at 707 Sunshine Dr, Oakland, MD 21550, 3 beds, 2 baths

$310,000 Last sold price

3 beds2 baths2,052 sq ft

707 Sunshine Dr, Oakland, MD 21550

(681) 252-3002

Property at 88 Knoll Crest Hts, Oakland, MD 21550, 3 beds, 2.5 baths

$225,000 Last sold price

3 beds2.5 baths1,867 sq ft

88 Knoll Crest Hts, Oakland, MD 21550

(301) 387-2000

Property at 929 Dogwood Dr, Oakland, MD 21550, 3 beds, 1 bath

$200,000 Last sold price

3 beds1 bath1,152 sq ft

929 Dogwood Dr, Oakland, MD 21550

(301) 387-4700

Property at 3472 Lake Shore Dr, Oakland, MD 21550, 5 beds, 5.5 baths

$775,000 Last sold price

5 beds5.5 baths2,904 sq ft

3472 Lake Shore Dr, Oakland, MD 21550

(301) 387-4700

Property at 1006 Lake Shore Dr, Oakland, MD 21550, 4 beds, 3 baths

$650,000 Last sold price

4 beds3 baths1,935 sq ft

1006 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 939 Glendale Rd #13, Oakland, MD 21550, 2 beds, 2 baths

$589,000 Last sold price

2 beds2 baths1,027 sq ft

939 Glendale Rd #13, Oakland, MD 21550

(866) 525-3466

Property at 793 Mountainview Dr, Oakland, MD 21550, 3 beds, 2.5 baths

$545,000 Last sold price

3 beds2.5 baths1,564 sq ft

793 Mountainview Dr, Oakland, MD 21550

(301) 387-2000

Property at 425 Mountainview Dr, Oakland, MD 21550, 3 beds, 3 baths

$739,000 Last sold price

3 beds3 baths1,825 sq ft

425 Mountainview Dr, Oakland, MD 21550

(301) 387-4700

Property at 181 Jeffrey Ln Unit 23D, Oakland, MD 21550, 2 beds, 1.5 baths

$311,500 Last sold price

2 beds1.5 baths800 sq ft

181 Jeffrey Ln Unit 23D, Oakland, MD 21550

(301) 387-4700

Property at 36 Jeffrey Ln Unit 6B, Oakland, MD 21550, 2 beds, 1 bath

$235,000 Last sold price

2 beds1 bath660 sq ft

36 Jeffrey Ln Unit 6B, Oakland, MD 21550

(301) 387-2000

Property at 12 Roman Ridge Rd Unit 22B, Oakland, MD 21550, 3 beds, 3.5 baths

$425,000 Last sold price

3 beds3.5 baths1,722 sq ft

12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

(301) 387-2000

Property at 939 Glendale Rd #2, Oakland, MD 21550, 3 beds, 3 baths

$820,000 Last sold price

3 beds3 baths— sq ft

939 Glendale Rd #2, Oakland, MD 21550

(301) 387-4700

Property at 1484 Paradise Point Rd, Oakland, MD 21550, 5 beds, 4.5 baths

$1,762,500 Last sold price

5 beds4.5 baths3,360 sq ft

1484 Paradise Point Rd, Oakland, MD 21550

(301) 387-2000

Property at 366 Glendale Rd, Oakland, MD 21550, 3 beds, 2 baths

$369,900 Last sold price

3 beds2 baths1,392 sq ft

366 Glendale Rd, Oakland, MD 21550

(202) 243-7700

Property at 186 Thornberry Rd, Oakland, MD 21550, 5 beds, 3.5 baths

$915,000 Last sold price

5 beds3.5 baths2,347 sq ft

186 Thornberry Rd, Oakland, MD 21550

(301) 387-4700

Property at 1100 S Blakeslee Rd, Oakland, MD 21550, 5 beds, 5.5 baths

$2,550,000 Last sold price

5 beds5.5 baths6,572 sq ft

1100 S Blakeslee Rd, Oakland, MD 21550

(301) 387-2000

Property at 5 Arrowhead Ln #5, Oakland, MD 21550, 3 beds, 3 baths

$635,000 Last sold price

3 beds3 baths1,650 sq ft

5 Arrowhead Ln #5, Oakland, MD 21550

(301) 387-2000

Property at 254 Middleton Rd, Oakland, MD 21550, 4 beds, 4 baths

$920,000 Last sold price

4 beds4 baths2,400 sq ft

254 Middleton Rd, Oakland, MD 21550

(301) 387-2000

Property at 421 Penn Cove Rd, Oakland, MD 21550, 4 beds, 3.5 baths

$1,350,000 Last sold price

4 beds3.5 baths4,284 sq ft

421 Penn Cove Rd, Oakland, MD 21550

(301) 387-2000

Property at 20160 Garrett Hwy Unit H712, Oakland, MD 21550, 1 bed, 1 bath

$339,000 Last sold price

1 bed1 bath450 sq ft

20160 Garrett Hwy Unit H712, Oakland, MD 21550

(301) 387-2000

Property at 20160 Garrett Hwy Unit G509, Oakland, MD 21550, 2 beds, 1 bath

$380,000 Last sold price

2 beds1 bath640 sq ft

20160 Garrett Hwy Unit G509, Oakland, MD 21550

(301) 387-4700

Property at 346 Skippers Point Rd, Oakland, MD 21550, 3 beds, 2 baths

$530,000 Last sold price

3 beds2 baths1,800 sq ft

346 Skippers Point Rd, Oakland, MD 21550

(301) 387-2000

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Recently Sold Homes in 21550

There are currently 114 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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