21550, MD homes for sale & real estate

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NEW 10 HRS AGO

ABOUT THIS HOME
21550, 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

NEW 15 HRS AGO

ABOUT THIS HOME
21550, 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

NEW 1 DAY AGO

ABOUT THIS HOME
21550, MD Homes for Sale
Welcome to your ultimate woodland retreat! Nestled in a private, serene setting, this meticulously maintained 3-bedroom, 3.5-bathroom log home perfectly blends rustic charm with modern luxury. Freshly painted throughout and boasting gleaming, well-maintained wide-plank hardwood floors and new carpeting, this property is completely turn-key. The heart of the home is the grand family room, which features soaring open ceilings, an abundance of natural light, and a majestic stone fireplace perfect for cozy evenings. Right off the family room, the newly renovated chef's kitchen comes fully equipped with granite countertops, brand-new appliances, a custom tile backsplash, and a garbage disposal.

$540,000

3 beds3.5 baths3,276 sq ft

204 Farm View Ln, Oakland, MD 21550

Grand family room • Granite countertops • 1.59 acre lot

(301) 698-5005

COMING SOON

ABOUT THIS HOME
21550, MD Homes for Sale
Rare opportunity to own a thoughtfully designed container home in the Deep Creek Lake area! This distinctive 2BR/2BA retreat combines modern comfort with a private wooded setting. The open-concept interior features abundant natural light, a full kitchen, comfortable living space, and large sliders connecting the indoors to the outdoors. Enjoy a private backyard with hot tub, fire pit, and grill, plus additional storage for outdoor gear. Conveniently located near Deep Creek Lake, Wisp Resort, hiking, biking, golf, boating, fishing, state park trails, and local dining. Built with quality, this home features Superior foundation walls, high end finishes and a mountaintop setting that is sure to

$645,000

2 beds2 baths1,520 sq ft

100 San Francisco St, Oakland, MD 21550

Hot tub • Grill • Private backyard

(301) 387-2000

ABOUT THIS HOME
21550, MD Homes for Sale
Location, location, location! Enjoy easy living in this one-level raised rancher featuring 3 bedrooms and 1.5 baths, with all bedrooms conveniently located on the main level. Beautiful hardwood floors add warmth, while the covered front porch and side covered deck offer inviting spaces to relax and enjoy the peaceful surroundings. The fenced-in backyard provides plenty of outdoor space for pets, play, or entertaining. The full basement is ready for your finishing touches and offers additional potential, while the attached one-car lower-level garage provides convenient parking or extra storage. Recent updates include a new roof and a full WaterGuard system installed along the interior baseme

$229,000

3 beds1.5 baths1,612 sq ft

139 S Oakhall Dr, Oakland, MD 21550

Covered front porch • Full basement • Waterguard system

(301) 387-4700

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 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 619 Hotel Rd, Deer Park, MD 21550, 1 bed, 1.5 baths

$185,000

1 bed1.5 baths1,536 sq ft

619 Hotel Rd, Deer Park, 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 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 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 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 102 Roanoke Ave, Oakland, MD 21550, 3 beds, 1 bath

$74,990

3 beds1 bath1,932 sq ft

102 Roanoke Ave, Oakland, MD 21550

(703) 378-8810

Property at 808 N St, Oakland, MD 21550, 2 beds, 2 baths

$229,900

2 beds2 baths1,008 sq ft

808 N St, Oakland, MD 21550

(301) 387-4700

Property at 1407 Broadford Rd, Oakland, MD 21550, 3 beds, 2 baths

$399,900

3 beds2 baths1,464 sq ft

1407 Broadford Rd, Oakland, MD 21550

(301) 387-4700

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 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 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 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 670 Woodlands Hill Ln, Oakland, MD 21550, 5 beds, 4.5 baths

$1,499,000

5 beds4.5 baths3,714 sq ft

670 Woodlands Hill Ln, Oakland, MD 21550

(301) 387-2000

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

$174,900

2 beds1 bath2,008 sq ft

206 W Liberty St, Oakland, MD 21550

(301) 387-2000

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

$169,000

3 beds1 bath1,516 sq ft

40 Sunshine, Oakland, MD 21550

(301) 387-4700

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

$399,000

3 beds2 baths1,456 sq ft

181 Glotfelty Dr, Oakland, MD 21550

(301) 387-2000

Property at 94 Sandy View Ct, Mc Henry, MD 21541, 5 beds, 3.5 baths

$835,000

5 beds3.5 baths2,734 sq ft

94 Sandy View Ct, Mc Henry, MD 21541

(301) 387-4700

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 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 312 Moss Creek Cir, Oakland, MD 21550, 5 beds, 3.5 baths

$699,000

5 beds3.5 baths4,230 sq ft

312 Moss Creek Cir, Oakland, MD 21550

(301) 387-4700

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

$249,900

2 beds2 baths560 sq ft

400 Bear Dr E, Oakland, MD 21550

(301) 387-4700

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Average home prices near 21550, MD

Cities

Zip Codes

21550, MD real estate trends

All Home Types trends in 21550, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$364,792

+7.6% 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

21550, MD

$364,792

+7.6%

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