Oakland, MD homes for sale & real estate

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NEW 30 HRS AGO

415 Nazelrod Rd, Oakland, MD 21550
415 Nazelrod Rd, Oakland, MD 21550
415 Nazelrod Rd, Oakland, MD 21550
ABOUT THIS HOME
Oakland, MD Homes for Sale
One of Garrett County's most unique and breathtaking estates—this completely custom masterpiece is set on over 63 acres of pristine land, offering unmatched privacy, panoramic valley views, and endless possibilities. Designed with meticulous attention to detail, this extraordinary home features radiant in-floor heating, a gourmet kitchen outfitted with restaurant-grade appliances and a full butler’s pantry, and a luxurious main-level primary suite. The expansive family room opens to not one, but two attached garages for ultimate convenience. Outside, follow scenic trails past several outbuildings to a year-round stream, winding through a stunning mix of open fields and wooded ac

$3,249,000

4 beds5 baths4,680 sq ft

415 Nazelrod Rd, Oakland, MD 21550

Gourmet kitchen • Butler's pantry • Attached garages

(301) 387-2000

COMING SOON

620 Crosby Dr, Oakland, MD 21550
620 Crosby Dr, Oakland, MD 21550
620 Crosby Dr, Oakland, MD 21550
ABOUT THIS HOME
Oakland, MD Homes for Sale
BRAND NEW CONSTRUCTION! 4BR/3.5BA home with attached 2 car garage in Country Club Acres! Perched at the very top of the mountain overlooking Oakland golf course, 2,850 sf and 2.84 acres of land (lots 73-79 combined). Modern design offering plenty of natural light, open living and elite finishes. Features include Andersen windows & sliders, multiple ensuites, custom tile bathrooms, fireplace, gourmet kitchen, Kraftmaid cabinets, granite counters, massive covered deck and lower patio area and an incredibly energy efficient home! Country Club Acres is a fantastic community (NO HOA) just outside of town with easy access to town parks, sport courts, trails, Youghiogheny River & Herri

$555,000

4 beds3.5 baths2,850 sq ft

620 Crosby Dr, Oakland, MD 21550

2.84 acre lot • 2 garage spots • Built 2025

(301) 387-4700

NEW 34 HRS AGO

1589 Lake Shore Dr, Oakland, MD 21550
1589 Lake Shore Dr, Oakland, MD 21550
1589 Lake Shore Dr, Oakland, MD 21550
ABOUT THIS HOME
Oakland, MD Homes for Sale
Exquisite one of a kind contemporary tucked away on sought after Lake Shore Drive. 128 feet of lake frontage on quiet Bee Tree Hollow Cove, with 20-foot-deep water depths off spacious Type A dock and total privacy. Perched high above the cove “The Birdhouse” offers expansive four-season views from every window. The property was thoughtfully designed and planned by current owners and local architect Douglas Storck with DCL Design Studio in 2018. The home was completed in January of 2020 and features unique and custom finishes throughout. The main level features a welcoming entrance, living room with modern gas fireplace, 12-foot vaulted ceilings, recessed lighting, durable hardw

$1,399,000

3 beds3 baths1,872 sq ft

1589 Lake Shore Dr, Oakland, MD 21550

Open concept kitchen • Total privacy • Lake frontage

(301) 387-4700

502 E Oak St, Oakland, MD 21550
502 E Oak St, Oakland, MD 21550
502 E Oak St, Oakland, MD 21550
ABOUT THIS HOME
Oakland, MD Homes for Sale
Welcome to this meticulously maintained one-level home in the heart of Oakland, MD! Boasting a spacious and thoughtfully designed interior, this 3-bedroom, 2-bathroom residence offers comfortable, easy living with room to relax and entertain. The open layout includes a bright living area, a well-appointed kitchen, and generous bedrooms that provide the perfect balance of privacy and convenience. The home sits on a mostly level lot with a flat driveway—ideal for all-season access and easy maintenance. Enjoy the ease of single-level living with no stairs to navigate, making it perfect for all ages. Located just minutes from all of Oakland's town amenities—shopping, dining, schools

$249,000

3 beds2 baths1,680 sq ft

502 E Oak St, Oakland, MD 21550

One level home • Flat driveway • Open layout

(301) 387-2000

1875 Pysell Crosscut Rd, Oakland, MD 21550
1875 Pysell Crosscut Rd, Oakland, MD 21550
1875 Pysell Crosscut Rd, Oakland, MD 21550
ABOUT THIS HOME
Oakland, MD Homes for Sale
Coming Soon! Beautifully maintained 5 bedroom 5 bathroom lake area chalet. Beautifully landscaped and situated on 4 +/- acres with partial views of the south side of Deep Creek Lake. This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished living space. Featuring a large heated garage with multiple car storage and additional partially finished accessory room, a beautifully built pavilion with bar area for outdoor entertaining, an almost brand new salt water hot tub, wraparound porch with expansive views, finished concrete walkways, expansive yard space. Recent interior upgrades include an almost new central forced air HVAC sy

$835,000

5 beds5 baths3,664 sq ft

1875 Pysell Crosscut Rd, Oakland, MD 21550

3.92 acre lot • Built 2004 • Listed 3 days

(301) 387-4700

Property at 939 Glendale Rd #19, Oakland, MD 21550, 3 beds, 2 baths

$785,000

3 beds2 baths1,432 sq ft

939 Glendale Rd #19, Oakland, MD 21550

(410) 241-3725

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

$399,900

2 beds1 bath640 sq ft

20160 Garrett Hwy Unit G509, Oakland, MD 21550

(301) 387-4700

Property at 198 Grandview Dr, Oakland, MD 21550, 3 beds, 3 baths

$825,000

3 beds3 baths2,744 sq ft

198 Grandview Dr, Oakland, MD 21550

(410) 224-4400

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

$519,000

2 beds2 baths1,379 sq ft

20160 Garrett Hwy Unit D310, Oakland, MD 21550

(703) 831-6806

Property at 1260 Gnegy Church Rd, Oakland, MD 21550, 3 beds, 3 baths

$449,000

3 beds3 baths4,420 sq ft

1260 Gnegy Church Rd, Oakland, MD 21550

(301) 387-2000

Property at 1019 Lake Shore Dr, Oakland, MD 21550, 4 beds, 4.5 baths

$1,755,000

4 beds4.5 baths2,605 sq ft

1019 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 1570 Garrett Rd, Oakland, MD 21550, 3 beds, 1 bath

$345,000

3 beds1 bath1,408 sq ft

1570 Garrett Rd, Oakland, MD 21550

(301) 387-8300

Property at 60 Gorman St, Oakland, MD 21550, 2 beds, 1 bath

$115,000

2 beds1 bath1,488 sq ft

60 Gorman St, Oakland, MD 21550

(410) 740-7100

Property at 565 Glendale Rd Unit 106 B, Oakland, MD 21550, 1 bed, 1 bath

$299,900

1 bed1 bath— sq ft

565 Glendale Rd Unit 106 B, Oakland, MD 21550

(301) 387-2000

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

$859,000

5 beds4 baths2,934 sq ft

873 Paradise Hts, Oakland, MD 21550

(301) 387-2000

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

$698,500

3 beds4 baths2,460 sq ft

94 Meadow Ct, Oakland, MD 21550

(301) 387-4700

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

$995,000

5 beds3.5 baths2,347 sq ft

186 Thornberry Rd, Oakland, MD 21550

(301) 387-4700

Property at 126 Leo Friend Rd, Oakland, MD 21550, 4 beds, 3 baths

$529,900

4 beds3 baths2,235 sq ft

126 Leo Friend Rd, Oakland, MD 21550

(301) 387-2000

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

$234,900

4 beds2 baths1,456 sq ft

2805 Shady Dell Rd, Oakland, MD 21550

(301) 387-4700

Property at 163 Crestview Dr, Oakland, MD 21550, 3 beds, 2.5 baths

$335,000

3 beds2.5 baths1,416 sq ft

163 Crestview Dr, Oakland, MD 21550

(301) 387-2000

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

$529,000

3 beds2 baths1,800 sq ft

346 Skippers Point Rd, Oakland, MD 21550

(301) 387-2000

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

$379,000

3 beds2 baths2,092 sq ft

17 Driftwood Ln, Oakland, MD 21550

(301) 387-2000

Property at 511 E Green St, Oakland, MD 21550, 4 beds, 2 baths

$309,000

4 beds2 baths1,880 sq ft

511 E Green St, Oakland, MD 21550

(301) 387-4700

Property at 19956 Garrett Hwy #6, Oakland, MD 21550, 4 beds, 4 baths

$1,349,000

4 beds4 baths3,000 sq ft

19956 Garrett Hwy #6, Oakland, MD 21550

(301) 387-2000

Property at 1737 King Wildesen Rd, Oakland, MD 21550, 3 beds, 2 baths

$299,900

3 beds2 baths1,736 sq ft

1737 King Wildesen Rd, Oakland, MD 21550

(301) 387-2000

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

$209,000

3 beds2 baths1,850 sq ft

170 Tannery Rd, Oakland, MD 21550

(888) 400-2513

Property at 20160 Garrett Hwy Unit H708, Oakland, MD 21550, 1 bed, 1 bath

$300,000

1 bed1 bath550 sq ft

20160 Garrett Hwy Unit H708, Oakland, MD 21550

(443) 574-1600

Property at 20676 Garrett Hwy, Oakland, MD 21550, 5 beds, 4.5 baths

$1,499,950

5 beds4.5 baths2,280 sq ft

20676 Garrett Hwy, Oakland, MD 21550

(855) 885-4663

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

$2,159,000

7 beds6.5 baths3,735 sq ft

237 Glendale Rd, Oakland, MD 21550

(301) 387-2000

Property at 333 Sloan Tract Rd, Oakland, MD 21550, 4 beds, 3.5 baths

$475,000

4 beds3.5 baths1,492 sq ft

333 Sloan Tract Rd, Oakland, MD 21550

(301) 387-4700

Property at 285 Winding Trail Ln Unit 10A, Oakland, MD 21550, 5 beds, 4.5 baths

$589,000

5 beds4.5 baths3,300 sq ft

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

(301) 387-2000

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

$139,000

2 beds1 bath720 sq ft

320 Coolidge Ave, Oakland, MD 21550

(301) 387-2000

Property at 62 Middleton Rd, Oakland, MD 21550, 3 beds, 2.5 baths

$829,900

3 beds2.5 baths2,397 sq ft

62 Middleton Rd, Oakland, MD 21550

(301) 387-2000

Property at 590 S Blakeslee Rd, Oakland, MD 21550, 4 beds, 3.5 baths

$1,249,000

4 beds3.5 baths3,071 sq ft

590 S Blakeslee Rd, Oakland, MD 21550

(301) 387-4700

Property at 501 Christophers Way, Oakland, MD 21550, 3 beds, 2 baths

$249,000

3 beds2 baths1,617 sq ft

501 Christophers Way, Oakland, MD 21550

(301) 387-4700

Property at 4 Laurel Brook Dr #4, Oakland, MD 21550, 2 beds, 2 baths

$235,000

2 beds2 baths— sq ft

4 Laurel Brook Dr #4, Oakland, MD 21550

(301) 387-4700

Property at 52 Dam View Dr, Oakland, MD 21550, 4 beds, 5 baths

$1,147,000

4 beds5 baths3,032 sq ft

52 Dam View Dr, Oakland, MD 21550

(301) 387-4700

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

$248,900

2 beds2 baths1,678 sq ft

2571 Shady Dell Rd, Oakland, MD 21550

(301) 334-5757

Property at 45 Village Dr #4, Oakland, MD 21550, 2 beds, 2 baths

$450,000

2 beds2 baths1,096 sq ft

45 Village Dr #4, Oakland, MD 21550

(301) 921-4500

Property at 531 Glendale Rd Unit B302, Oakland, MD 21550, 2 beds, 1 bath

$369,000

2 beds1 bath887 sq ft

531 Glendale Rd Unit B302, Oakland, MD 21550

(301) 387-2000

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

$600,000

2 beds2 baths1,027 sq ft

939 Glendale Rd #13, Oakland, MD 21550

(866) 525-3466

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Average home prices near Oakland, MD

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Zip Codes

21550 homes for sale
$449,000

Oakland, MD real estate trends

$560K

Sale price

+224.3%
since last year

$169

Sale $/sq ft

+56.5%
since last year

Under list price

Days on market

Down payment

—

Total homes sold

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