21550, MD homes for sale & real estate

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258 Winding Trail Ln Unit 8B, Oakland, MD 21550
258 Winding Trail Ln Unit 8B, Oakland, MD 21550
258 Winding Trail Ln Unit 8B, Oakland, MD 21550
ABOUT THIS HOME
21550, MD Homes for Sale
258 Winding Trail Lane is a luxurious duplex home located in the serene yet convenient community of Timberlake Village. The home feels warm and inviting from the moment you enter. Offering 3,300 SF with an open floorplan, three levels of living space, a large kitchen with granite countertops, two stone propane fireplaces, and LVF on the main and lower levels. This home boasts many recent upgrades, including a tankless water heater and a new washer and dryer. The location feels very private, and the wooded setting makes for an ideal backdrop to this great property. Step outside to enjoy a nice covered deck, fenced in backyard, hot tub and a firepit. If you are looking for a home that checks

$609,000

5 beds4.5 baths3,300 sq ft

258 Winding Trail Ln Unit 8B, Oakland, MD 21550

$350 HOA • Car-dependent

(301) 387-4700

20241 Garrett Hwy #5, Oakland, MD 21550
20241 Garrett Hwy #5, Oakland, MD 21550
20241 Garrett Hwy #5, Oakland, MD 21550
ABOUT THIS HOME
21550, MD Homes for Sale
Located right in the heart of Deep Creek Lake, this stunning 3-level condo offers the perfect blend of luxury and comfort with breathtaking water views! Boasting 3 spacious bedrooms and 2.5 baths, this home features an open-concept main floor with an eat in kitchen, cozy living area, separate dining space, breakfast nook, and large windows that flood the space with natural light. The main level also hosts a tranquil primary suite with an updated bathroom, while the upper lower level provides two additional bedrooms with a shared bath. The lower level includes an additional living area along with a half bath, ideal for a family room, office, or guest retreat. An attached 1-car garage adds co

$395,000

3 beds2.5 baths2,330 sq ft

20241 Garrett Hwy #5, Oakland, MD 21550

$67 HOA • Garage • Car-dependent

(301) 387-2000

COMING SOON

$1,100,000

4 beds3.5 baths3,348 sq ft

267 Woodlands Hill Ln, Oakland, MD 21550

2.21 acre lot • $67 HOA • 2 garage spots

(703) 752-8660

735 Winston Rd, Oakland, MD 21550
735 Winston Rd, Oakland, MD 21550
735 Winston Rd, Oakland, MD 21550
ABOUT THIS HOME
21550, MD Homes for Sale
366.62 acre farm 30 minutes from Deep Creek Lake, 30 minutes from Canaan Valley West Virginia offers cleared farmland and wooded acreage teeming with wildlife, this farm nestled in the woods along Route 50 is suited for hunters and homesteaders alike. Along with plenty of room to roam and abundant privacy, this property features two farm sheds with ample workspace, storage space and potential office space; a detached 3-bay garage and a family home. The 1985 residence is solid post and beam construction, with hardwood floors, finished wood walls and plenty of large windows offering abundant natural light on both floors. The partial wraparound porch attached to a small enclosed back entrance

$1,300,000

2 beds2 baths2,076 sq ft

735 Winston Rd, Oakland, MD 21550

367 acre lot • 3 garage spots • Car-dependent

(301) 387-8300

1385 Mountainview Dr, Oakland, MD 21550
1385 Mountainview Dr, Oakland, MD 21550
1385 Mountainview Dr, Oakland, MD 21550
ABOUT THIS HOME
21550, MD Homes for Sale
Nestled in a serene wooded neighborhood, this stunning water-access chalet offers the perfect blend of rustic charm and modern comfort. Spanning three levels and over 2600 sq ft of finished space, the home boasts an inviting open-concept living space with a striking stone fireplace, perfect for cozy evenings. The main floor features a well-appointed kitchen, a spacious dining area, and large windows that flood the space with natural light. With three comfortable bedrooms, including a private primary suite, there's plenty of room for family and guests. The lower level could easily function and/or be converted to a 4th bedroom. Step outside to enjoy the gorgeous outdoor area, ideal for relaxi

$639,000

3 beds3 baths2,660 sq ft

1385 Mountainview Dr, Oakland, MD 21550

1.04 acre lot • $132 HOA • 2 garage spots

(301) 387-2000

Property at 247 Winding Trail Ln Unit 6B, Oakland, MD 21550, 5 beds, 4.5 baths

$599,900

5 beds4.5 baths3,300 sq ft

247 Winding Trail Ln Unit 6B, Oakland, MD 21550

(301) 387-2000

Property at 134 Knoll Crest Heights Dr, Oakland, MD 21550, 4 beds, 2 baths

$249,000

4 beds2 baths2,408 sq ft

134 Knoll Crest Heights Dr, Oakland, MD 21550

(703) 752-8660

Property at 607 K, Mountain Lake Park, MD 21550, 4 beds, 2 baths

$199,000

4 beds2 baths1,332 sq ft

607 K, Mountain Lake Park, MD 21550

(301) 387-4700

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

$520,000

2 beds2 baths1,096 sq ft

45 Village Dr #4, Oakland, MD 21550

(301) 921-4500

Property at 426 Pergin Farm Rd, Oakland, MD 21550, 3 beds, 2 baths

$449,000

3 beds2 baths1,596 sq ft

426 Pergin Farm Rd, Oakland, MD 21550

(301) 387-4700

Property at 36 Ridgewood Dr, Oakland, MD 21550, 3 beds, 3.5 baths

$589,000

3 beds3.5 baths1,713 sq ft

36 Ridgewood Dr, Oakland, MD 21550

(301) 387-2000

Property at 565 Glendale Rd #312, Oakland, MD 21550, 1 bed, 1 bath

$259,999

1 bed1 bath785 sq ft

565 Glendale Rd #312, Oakland, MD 21550

(443) 275-7188

Property at 114 Waterwheel Rd, Oakland, MD 21550, 3 beds, 1 bath

$289,000

3 beds1 bath960 sq ft

114 Waterwheel Rd, Oakland, MD 21550

(301) 387-4700

Property at 603 Oak, Oakland, MD 21550, 3 beds, 1.5 baths

$220,000

3 beds1.5 baths1,200 sq ft

603 Oak, Oakland, MD 21550

(301) 387-2000

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

$250,000

2 beds2 baths1,678 sq ft

2571 Shady Dell Rd, Oakland, MD 21550

(888) 860-7369

Property at 130 Timberloft Cir #14, Oakland, MD 21550, 3 beds, 3 baths

$780,000

3 beds3 baths1,900 sq ft

130 Timberloft Cir #14, Oakland, MD 21550

(301) 387-2000

Property at 3084 Lake Shore Dr, Oakland, MD 21550, 4 beds, 3 baths

$665,000

4 beds3 baths2,464 sq ft

3084 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 31 Mount Airy Ct, Oakland, MD 21550, 3 beds, 2 baths

$129,900

3 beds2 baths1,092 sq ft

31 Mount Airy Ct, Oakland, MD 21550

(301) 387-4700

Property at 180 Paradise Ridge Rd, Oakland, MD 21550, 3 beds, 2 baths

$425,000

3 beds2 baths1,152 sq ft

180 Paradise Ridge Rd, Oakland, MD 21550

(301) 387-2000

Property at 29 Sloan Tract Rd, Oakland, MD 21550, 3 beds, 2 baths

$349,900

3 beds2 baths960 sq ft

29 Sloan Tract Rd, Oakland, MD 21550

(301) 387-2000

Property at 5459 Hutton Rd, Oakland, MD 21550, 4 beds, 2 baths

$175,000

4 beds2 baths2,000 sq ft

5459 Hutton Rd, Oakland, MD 21550

(301) 722-4700

Property at 215 Lower Penn Point Dr, Oakland, MD 21550, 5 beds, 4.5 baths

$1,400,000

5 beds4.5 baths2,580 sq ft

215 Lower Penn Point Dr, Oakland, MD 21550

(301) 387-2000

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

$359,000

2 beds1.5 baths800 sq ft

181 Jeffrey Ln Unit 23D, Oakland, MD 21550

(301) 387-4700

Property at 65 Village Dr #6, Oakland, MD 21550, 3 beds, 3 baths

$725,000

3 beds3 baths1,740 sq ft

65 Village Dr #6, Oakland, MD 21550

(301) 387-2000

Property at 6652 George Washington Hwy, Oakland, MD 21550, 6 beds, 2.5 baths

$760,000

6 beds2.5 baths2,672 sq ft

6652 George Washington Hwy, Oakland, MD 21550

(301) 387-2000

Property at 1359 Cedar Ln, Oakland, MD 21550, 2 beds, 1.5 baths

$325,000

2 beds1.5 baths1,600 sq ft

1359 Cedar Ln, Oakland, MD 21550

(410) 326-4100

Property at 158 Silver Tree Ln, Oakland, MD 21550, 5 beds, 4.5 baths

$829,900

5 beds4.5 baths2,250 sq ft

158 Silver Tree Ln, Oakland, MD 21550

(301) 387-2000

Property at 465 King Wildesen Rd, Oakland, MD 21550, 2 beds, 1 bath

$429,900

2 beds1 bath768 sq ft

465 King Wildesen Rd, Oakland, MD 21550

(301) 334-8454

Property at 223 Old Crellin Rd, Oakland, MD 21550, 1 bed, 1 bath

$225,000

1 bed1 bath980 sq ft

223 Old Crellin Rd, Oakland, MD 21550

(717) 650-1284

Property at 511 Main St, Deer Park, MD 21550, 5 beds, 1.5 baths

$235,000

5 beds1.5 baths1,536 sq ft

511 Main St, Deer Park, MD 21550

(301) 387-8300

Property at 145 Lower Penn Point Dr, Oakland, MD 21550, 2 beds, 3.5 baths

$997,900

2 beds3.5 baths2,106 sq ft

145 Lower Penn Point Dr, Oakland, MD 21550

(855) 450-0442

Property at 565 Glendale Rd #212, Oakland, MD 21550, 1 bed, 1 bath

$221,000

1 bed1 bath527 sq ft

565 Glendale Rd #212, Oakland, MD 21550

(301) 387-2000

Property at 230 Moose Xing, Oakland, MD 21550, 3 beds, 2 baths

$499,000

3 beds2 baths2,441 sq ft

230 Moose Xing, Oakland, MD 21550

(301) 387-2000

Property at 202 Deerfield Dr, Oakland, MD 21550, 4 beds, 3 baths

$320,500

4 beds3 baths2,720 sq ft

202 Deerfield Dr, Oakland, MD 21550

(304) 788-3322

Property at 1118 Lake Shore Dr, Oakland, MD 21550, 3 beds, 2 baths

$675,000

3 beds2 baths2,446 sq ft

1118 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

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

$1,479,000

4 beds3 baths1,844 sq ft

20698 Garrett Hwy, Oakland, MD 21550

(301) 387-4700

Property at 15 Village Dr #1, Oakland, MD 21550, 2 beds, 1 bath

$530,000

2 beds1 bath— sq ft

15 Village Dr #1, Oakland, MD 21550

(301) 387-2000

Property at 1240 Boy Scout Rd, Oakland, MD 21550, 7 beds, 6 baths

$4,750,000

7 beds6 baths3,695 sq ft

1240 Boy Scout Rd, Oakland, MD 21550

(443) 574-1600

Property at 3941 Pleasant Valley Rd, Oakland, MD 21550, 3 beds, 2 baths

$180,000

3 beds2 baths2,060 sq ft

3941 Pleasant Valley Rd, Oakland, MD 21550

(301) 387-2000

Property at 383 Penn Cove Rd, Oakland, MD 21550, 5 beds, 3 baths

$1,599,000

5 beds3 baths2,080 sq ft

383 Penn Cove Rd, Oakland, MD 21550

(301) 387-4700

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Average home prices near 21550, MD

Cities

Zip Codes

21550, MD real estate trends

$379K

Sale price

-5.2%
since last year

$231

Sale $/sq ft

+40.9%
since last year

Under list price

4.9%

Days on market

Down payment

—

Total homes sold

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