Oakland, MD homes for sale & real estate

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ABOUT THIS HOME
Oakland, MD Homes for Sale
Immaculate from top to bottom, this exceptional five-bedroom home offers three levels of beautifully maintained living space, making it an ideal choice for a primary residence. Thoughtfully designed for comfortable everyday living, the home provides plenty of room to gather, relax, and spread out. A stunning fireplace creates a warm and inviting focal point, while the attached two-car garage adds convenience and storage. Above the garage, an unfinished room offers exciting potential for additional storage, an office, guest quarters, or additional living space. The downstairs family room offers expansive square footage for cozy gatherings. Numerous recent upgrades, including a new roof, high

$499,000

5 beds3.5 baths3,800 sq ft

607 Pin Oak Cir, Oakland, MD 21550

Unfinished room • Close to wisp resort • 0.56 acre lot

(301) 387-2000

ABOUT THIS HOME
Oakland, MD Homes for Sale
Roman Ridge is the perfect location for your Deep Creek retreat! This unit has been very well taken care of and conveys fully furnished for immediate enjoyment! Main floor bedroom with full bath and upper level loft bedroom provide great resting space for family and friends. The inviting living area is complete with a warm wood-burning fireplace, perfect for those cool Garrett County evenings! Excellently maintained with new appliances to include stove, refrigerator and hot water heater. Enjoy outdoor entertaining with wonderful lake and mountain views from the expanded deck! Take a look now at Roman Ridge!

$279,000

2 beds1 bath700 sq ft

127 Jeffrey Ln #4, Oakland, MD 21550

Expanded deck • New appliances • Main floor bedroom

(301) 387-2000

ABOUT THIS HOME
Oakland, MD Homes for Sale
Deep Creek Lake living, without the upkeep. This Silver Tree Suites unit features two beds, an oversized loft, plus a kitchenette, gas fireplace, and private balcony. That's paired with resort-style on-site amenities: a marina, fitness room, sauna, and expansive lakefront deck, all just steps from your door. Dutch's at Silver Tree is directly adjoining along with the Harbor Bar, and Wisp Resort, state parks, and year-round recreation are minutes away. Already an active vacation rental, so the income starts the day you close. Call for more details or to schedule your private tour today!

$279,000

2 beds1 bath772 sq ft

565 Glendale Rd #316, Oakland, MD 21550

Kitchenette • Private balcony • Sauna

(301) 387-2000

ABOUT THIS HOME
Oakland, MD Homes for Sale
Comfy, cozy, and full of mountain charm! This inviting 2-bedroom, 1.5-bath cabin is nestled on 1.26 private acres within Yough Mountain Resort, offering the perfect setting for a weekend getaway, recreational retreat, or peaceful escape. The open floor plan creates a comfortable gathering space, highlighted by a beautiful stone fireplace with a wood-burning insert that adds warmth and character, while stainless steel appliances and recent updates make the home easy to enjoy. Recent improvements include laminate flooring, added washer and dryer hookups, a water filtration system, a vapor barrier installed in the crawlspace, a new gravel circular driveway, and a new shed for additional storag

$235,000

2 beds1.5 baths1,152 sq ft

1959 Birchwood Dr, Oakland, MD 21550

Laminate flooring • Stone fireplace • 1.26 acre lot

(301) 387-4700

ABOUT THIS HOME
Oakland, MD Homes for Sale
This exquisite Northern White Cedar Construction (naturally rot resistant) log home offers a harmonious blend of rustic charm and modern luxury. The spacious, open floor plan invites you to experience a warm and inviting atmosphere, accentuated by stunning wood floors and walls, cathedral beam ceiling, and a cozy stone fireplace with glass doors, perfect for intimate gatherings. The heart of the home features a well-appointed kitchen equipped with nice appliances, and an eat-in bar. Retreat to the spacious primary suite, complemented by two additional bedrooms, providing ample space for relaxation. The fully finished basement, with a convenient walkout entrance just steps from the driveway,

$639,000

3 beds2.5 baths1,933 sq ft

1529 Paradise Point Rd, Oakland, MD 21550

Open floor plan • Cozy stone fireplace • Walkout entrance

(301) 387-4700

Property at 100 San Francisco St, Oakland, MD 21550, 2 beds, 2 baths

$645,000

2 beds2 baths1,520 sq ft

100 San Francisco St, Oakland, MD 21550

(301) 387-2000

Property at 184 Upper Penn Point Dr, Oakland, MD 21550, 3 beds, 2 baths

$920,000

3 beds2 baths1,152 sq ft

184 Upper Penn Point Dr, Oakland, MD 21550

(301) 387-2000

Property at 482 Pergin Farm Rd, Oakland, MD 21550, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths2,160 sq ft

482 Pergin Farm Rd, Oakland, MD 21550

(301) 387-4700

Property at 395 Woodlands Hill Ln, Oakland, MD 21550, 5 beds, 6 baths

$899,900

5 beds6 baths3,160 sq ft

395 Woodlands Hill Ln, Oakland, MD 21550

(301) 387-2000

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

$444,700

4 beds3.5 baths1,585 sq ft

333 Sloan Tract Rd, Oakland, MD 21550

(301) 722-4700

Property at 586 Bray School Rd, Oakland, MD 21550, 4 beds, 2 baths

$289,000

4 beds2 baths2,240 sq ft

586 Bray School Rd, Oakland, MD 21550

(301) 259-1119

Property at 20160 Garett Hwy Unit 105A, Oakland, MD 21550, 1 bed, 1 bath

$296,500

1 bed1 bath600 sq ft

20160 Garett Hwy Unit 105A, Oakland, MD 21550

(301) 387-2000

Property at 15 Byran Dr, Oakland, MD 21550, 4 beds, 4 baths

$799,900

4 beds4 baths— sq ft

15 Byran Dr, Oakland, MD 21550

(301) 387-2000

Property at 20698 Garrett Hwy, Oakland, MD 21550, 4 beds, 3 baths

$1,199,000

4 beds3 baths1,844 sq ft

20698 Garrett Hwy, Oakland, MD 21550

(301) 387-4700

Property at 325 Markwood Dr, Oakland, MD 21550, 4 beds, 3.5 baths

$769,000

4 beds3.5 baths3,376 sq ft

325 Markwood Dr, Oakland, MD 21550

(301) 387-4700

Property at 941 Mountainview Dr, Oakland, MD 21550, 4 beds, 3.5 baths

$719,999

4 beds3.5 baths4,377 sq ft

941 Mountainview Dr, Oakland, MD 21550

(301) 387-2000

Property at 180 Paradise Ridge Rd, Oakland, MD 21550, 4 beds, 3 baths

$689,000

4 beds3 baths2,402 sq ft

180 Paradise Ridge Rd, Oakland, MD 21550

(301) 387-4700

Property at 206 W Liberty St, Oakland, MD 21550, 2 beds, 1 bath

$149,000

2 beds1 bath2,008 sq ft

206 W Liberty St, Oakland, MD 21550

(301) 387-2000

Property at 193 Red Run Rd Unit 1-B-3, Oakland, MD 21550, 2 beds, 2 baths

$550,000

2 beds2 baths1,340 sq ft

193 Red Run Rd Unit 1-B-3, Oakland, MD 21550

(301) 698-5005

Property at 17240 Garrett Hwy, Oakland, MD 21550, 6 beds, 4.5 baths

$899,000

6 beds4.5 baths5,547 sq ft

17240 Garrett Hwy, Oakland, MD 21550

(301) 387-2000

Property at 40 Sunshine, Oakland, MD 21550, 3 beds, 1 bath

$159,000

3 beds1 bath1,516 sq ft

40 Sunshine, Oakland, MD 21550

(301) 387-4700

Property at 112 E Pennington St, Oakland, MD 21550, 5 beds, 3 baths

$325,000

5 beds3 baths2,165 sq ft

112 E Pennington St, Oakland, MD 21550

(866) 525-3466

Property at 1131 Lake Shore Dr, Oakland, MD 21550, 8 beds, 9 baths

$3,950,000

8 beds9 baths6,486 sq ft

1131 Lake Shore Dr, Oakland, MD 21550

(301) 387-4700

Property at 122 Woodlands Hill Ln, Oakland, MD 21550, 4 beds, 4.5 baths

$1,089,000

4 beds4.5 baths2,656 sq ft

122 Woodlands Hill Ln, Oakland, MD 21550

(301) 387-4700

Property at 943 Paradise Hts, Oakland, MD 21550, 5 beds, 3 baths

$745,000

5 beds3 baths2,200 sq ft

943 Paradise Hts, Oakland, MD 21550

(301) 387-2000

Property at 560 Glendale Rd, Oakland, MD 21550, 2 beds, 1 bath

$374,900

2 beds1 bath700 sq ft

560 Glendale Rd, Oakland, MD 21550

(301) 387-2000

Property at 187 Lower Penn Point Dr, Oakland, MD 21550, 3 beds, 2 baths

$1,425,000

3 beds2 baths1,695 sq ft

187 Lower Penn Point Dr, Oakland, MD 21550

(301) 387-2000

Property at 181 Glotfelty Dr, Oakland, MD 21550, 3 beds, 2 baths

$374,900

3 beds2 baths1,456 sq ft

181 Glotfelty Dr, Oakland, MD 21550

(301) 387-2000

Property at 256 Jeffrey Ln #28, Oakland, MD 21550, 3 beds, 3.5 baths

$464,900

3 beds3.5 baths1,838 sq ft

256 Jeffrey Ln #28, Oakland, MD 21550

(301) 387-2000

Property at 1167 Tall Oaks Dr, Oakland, MD 21550, 2 beds, 2.5 baths

$349,000

2 beds2.5 baths1,920 sq ft

1167 Tall Oaks Dr, Oakland, MD 21550

(301) 387-2000

Property at 127 Paradise Hts, Oakland, MD 21550, 3 beds, 2.5 baths

$999,999

3 beds2.5 baths2,240 sq ft

127 Paradise Hts, Oakland, MD 21550

(888) 838-9044

Property at 565 Glendale Rd #213, Oakland, MD 21550, 1 bed, 1 bath

$225,000

1 bed1 bath— sq ft

565 Glendale Rd #213, Oakland, MD 21550

(443) 574-1600

Property at 18948 Garrett Hwy, Oakland, MD 21550, 2 beds, 2 baths

$375,000

2 beds2 baths1,404 sq ft

18948 Garrett Hwy, Oakland, MD 21550

(301) 387-8300

Property at 400 Bear Dr E, Oakland, MD 21550, 2 beds, 2 baths

$235,000

2 beds2 baths560 sq ft

400 Bear Dr E, Oakland, MD 21550

(301) 387-4700

Property at 251 Robinwood Dr, Oakland, MD 21550, 5 beds, 4.5 baths

$775,000

5 beds4.5 baths4,284 sq ft

251 Robinwood Dr, Oakland, MD 21550

(301) 387-4700

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

$1,059,900

4 beds5 baths3,032 sq ft

52 Dam View Dr, Oakland, MD 21550

(301) 387-2000

Property at 1499 Foster Rd, Oakland, MD 21550, 4 beds, 2 baths

$375,000

4 beds2 baths2,234 sq ft

1499 Foster Rd, Oakland, MD 21550

(301) 387-2000

Property at 141 Montana Ln, Oakland, MD 21550, 1 bed, 1.5 baths

$219,000

1 bed1.5 baths912 sq ft

141 Montana Ln, Oakland, MD 21550

(301) 387-2000

Property at 102 N 3rd St, Oakland, MD 21550, 3 beds, 2 baths

$259,900

3 beds2 baths1,998 sq ft

102 N 3rd St, Oakland, MD 21550

(301) 387-2000

Property at 660 Glendale Rd, Oakland, MD 21550, 5 beds, 3 baths

$999,000

5 beds3 baths2,592 sq ft

660 Glendale Rd, Oakland, MD 21550

(301) 387-2000

Property at 231 Santa Fe Trl, Oakland, MD 21550, 4 beds, 3 baths

$629,000

4 beds3 baths2,280 sq ft

231 Santa Fe Trl, Oakland, MD 21550

(301) 387-4700

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Average home prices near Oakland, MD

Cities

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$174,900
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$280,000
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Tunnelton homes for sale
Accident homes for sale
$625,000
Swanton homes for sale
$1,299,000
Terra Alta homes for sale
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Elk Garden homes for sale
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Albright homes for sale
$89,900
Kingwood homes for sale
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Mountain Lake Park homes for sale
$229,900

Zip Codes

21550 homes for sale
$446,850

Oakland, MD real estate trends

All Home Types trends in Oakland, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$369,655

+70.0% YoY | Aug 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2026

Growth

% YoY

Oakland, MD

$369,655

+70.0%

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