Recently Sold Homes in Oakland, MD

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SOLD OCT 15, 2025

ABOUT THIS HOME
Recently Sold Home in Oakland, 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 NOV 24, 2025

ABOUT THIS HOME
Recently Sold Home in Oakland, MD:
Inviting Country 3-Bedroom Traditional Farmhouse. This updated farmhouse offers a perfect mix of character and modern upgrades. Featuring 3 bedrooms, a bright sun porch, and a detached 2-car garage, the home is designed for both comfort and convenience. Enjoy outdoor living with a fenced-in yard, back deck, and peaceful valley views. The location is ideal—just minutes from town and shopping. Recent improvements include: LVT flooring & carpet, updated stove/range, metal roof and gutters, replacement windows. Full of farmhouse charm and move-in ready. Call now for your private tour!

$180,000 Last sold price

3 beds1 bath1,322 sq ft

627 Hamill St, Oakland, MD 21550

(301) 387-2000

SOLD NOV 20, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Oakland, MD:
Welcome to this impeccably crafted 4-bedroom, 3-bath home in the desirable Silver Ridge community at Deep Creek Lake. From the moment you arrive, the home’s curb appeal is undeniable—classic craftsman-style architecture, a bold red exterior with stone accents, and a welcoming covered porch create an immediate sense of charm and quality. With four private deeded parking spaces located directly in front of the home, convenience meets comfort right at your doorstep. Step inside to discover a residence defined by craftsmanship and thoughtful design. Soaring ceilings and a striking stone fireplace anchor the open-concept living area, while rich wood finishes and upscale details add w

$555,000 Last sold price

4 beds3 baths2,700 sq ft

16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

(301) 387-2000

SOLD SEP 2, 2025

ABOUT THIS HOME
Recently Sold Home in Oakland, 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 NOV 13, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Oakland, MD:
A magnificent waterfront retreat in The Reserve at Holy Cross on the shores of Deep Creek Lake, representing the pinnacle of lake life living. This incomparable estate captures the essence of refined waterfront with a private dock, expansive outdoor entertaining spaces, and tranquil lakeside ambiance. Featuring 7 total bedrooms, 5 of which are en-suites, this home was thoughtfully designed with privacy, comfort, and flexibility in mind. Nature and luxury converge in perfect harmony with beautifully landscaped grounds creating an unmatched backdrop for lakefront gatherings, comfort and peace of mind.

$3,375,000 Last sold price

7 beds6.5 baths5,681 sq ft

870 Holy Cross Dr, Oakland, MD 21550

(301) 387-2000

Property at 215 N 10th St, Oakland, MD 21550, 3 beds, 1 bath

$279,000 Last sold price

3 beds1 bath1,518 sq ft

215 N 10th St, Oakland, MD 21550

(301) 334-8454

Property at 648 S 3rd St, Oakland, MD 21550, 3 beds, 2 baths

$275,000 Last sold price

3 beds2 baths1,488 sq ft

648 S 3rd St, Oakland, MD 21550

(301) 387-2000

Property at 110 W Pennington St, Oakland, MD 21550, 2 beds, 1 bath

$110,000 Last sold price

2 beds1 bath768 sq ft

110 W Pennington St, Oakland, MD 21550

(301) 387-4700

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 1056 Sunrise Dr, Oakland, MD 21550, 4 beds, 2.5 baths

$280,000 Last sold price

4 beds2.5 baths1,528 sq ft

1056 Sunrise Dr, 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 1567 Pergin Farm Rd, Oakland, MD 21550, 5 beds, 3.5 baths

$1,542,000 Last sold price

5 beds3.5 baths3,200 sq ft

1567 Pergin Farm Rd, 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 501 Christophers Way, Oakland, MD 21550, 3 beds, 2 baths

$195,000 Last sold price

3 beds2 baths1,617 sq ft

501 Christophers Way, Oakland, MD 21550

(301) 387-4700

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 1764 Underwood Rd, Oakland, MD 21550, 4 beds, 1.5 baths

$285,000 Last sold price

4 beds1.5 baths2,304 sq ft

1764 Underwood Rd, Oakland, MD 21550

(301) 387-4700

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 445 Dennett Rd, Oakland, MD 21550, 3 beds, 1 bath

$305,000 Last sold price

3 beds1 bath1,410 sq ft

445 Dennett Rd, Oakland, MD 21550

(301) 387-2000

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 11 Sunset Dr, Oakland, MD 21550, 3 beds, 2 baths

$270,000 Last sold price

3 beds2 baths1,400 sq ft

11 Sunset Dr, Oakland, MD 21550

(301) 387-4700

Property at 17 Driftwood Ln, Oakland, MD 21550, 3 beds, 2 baths

$305,000 Last sold price

3 beds2 baths2,092 sq ft

17 Driftwood Ln, 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 590 S Blakeslee Rd, Oakland, MD 21550, 4 beds, 3.5 baths

$1,150,000 Last sold price

4 beds3.5 baths3,071 sq ft

590 S Blakeslee Rd, Oakland, MD 21550

(301) 387-4700

Property at 157 Jeffrey Ln Unit 21A, Oakland, MD 21550, 2 beds, 1 bath

$237,000 Last sold price

2 beds1 bath660 sq ft

157 Jeffrey Ln Unit 21A, Oakland, MD 21550

(301) 387-4700

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 36 Jeffrey Ln Unit 6A, Oakland, MD 21550, 2 beds, 1 bath

$225,000 Last sold price

2 beds1 bath520 sq ft

36 Jeffrey Ln Unit 6A, 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 36 Ridgewood Dr, Oakland, MD 21550, 3 beds, 3.5 baths

$505,000 Last sold price

3 beds3.5 baths1,713 sq ft

36 Ridgewood 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 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 baths2,202 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 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 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 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 72 Cliff Dr, Oakland, MD 21550, 3 beds, 2 baths

$558,000 Last sold price

3 beds2 baths2,176 sq ft

72 Cliff Dr, Oakland, MD 21550

(301) 387-2000

Property at 2463 Mayhew Inn Rd, Oakland, MD 21550, 6 beds, 5.5 baths

$1,950,000 Last sold price

6 beds5.5 baths5,389 sq ft

2463 Mayhew Inn Rd, Oakland, MD 21550

(301) 387-2000

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Recently Sold Homes in Oakland

There are currently 109 recently sold homes for sale in Oakland at a median listing price of $440K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oakland stay on the market for 149 days. This map is refreshed with the newest listings in Oakland every 15 minutes.

In the past month, 5 homes have been sold in Oakland. In addition to houses in Oakland, there was also 1 condo, 3 townhouses, and 1 multi-family unit for sale in Oakland last month. Find your dream home in Oakland 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 Oakland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oakland. Our Oakland real estate stats and trends will give you more information about home buying and selling trends in Oakland. If you're looking to sell your home in the Oakland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oakland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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