Homes for Sale in Oakland, MD

price
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$20,000 | Whispering Pines Lane, Oakland, MD 21550
New

$20,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.51
Acres

Whispering Pines Lane, Oakland, MD 21550

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$199,000 | 408 M Street, Oakland, MD 21550
1/48

$199,000

2
Bedrooms
1,368
Square Feet
0.28
Acres

408 M Street, Oakland, MD 21550

$699,999 | 36 Greenstone Way, Oakland, MD 21550
1/68

$699,999

4
Bedrooms
1,932
Square Feet
0.50
Acres

36 Greenstone Way, Oakland, MD 21550

$645,000 | 100 San Francisco Street, Oakland, MD 21550
1/52

$645,000

2
Bedrooms
1,520
Square Feet
0.69
Acres

100 San Francisco Street, Oakland, MD 21550

$235,000 | 1959 Birchwood Drive, Oakland, MD 21550
1/36
Virtual Tour

$235,000

2
Bedrooms
1,152
Square Feet
1.26
Acres

1959 Birchwood Drive, Oakland, MD 21550

$639,000 | 1529 Paradise Point Road, Oakland, MD 21550
1/67
Virtual Tour

$639,000

3
Bedrooms
1,933
Square Feet
0.63
Acres

1529 Paradise Point Road, Oakland, MD 21550

$499,000 | 607 Pin Oak Circle, Oakland, MD 21550
1/77

$499,000

5
Bedrooms
3,800
Square Feet
0.56
Acres

607 Pin Oak Circle, Oakland, MD 21550

$229,000 | 139 South Oakhall Drive, Oakland, MD 21550
1/52
Virtual Tour

$229,000

3
Bedrooms
1,612
Square Feet
0.22
Acres

139 South Oakhall Drive, Oakland, MD 21550

a view of a swimming pool with a yard
1/25

$296,500

1
Bedrooms
600
Square Feet

20160 Garrett Highway, Unit 105A, Oakland, MD 21550

$289,000 | 586 Bray School Road, Oakland, MD 21550
1/32

$289,000

4
Bedrooms
2,240
Square Feet
1
Acres

586 Bray School Road, Oakland, MD 21550

$6,500 | Cedar Lane, Oakland, MD 21550
1/12

$6,500

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.94
Acres

Cedar Lane, Oakland, MD 21550

a green field with lots of trees in the background
1/26

$37,500

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1
Acres

Wild Turkey Lane, Oakland, MD 21550

$185,000 | 619 Hotel Road, Deer Park, MD 21550
1/63

$185,000

1
Bedrooms
1,536
Square Feet
0.20
Acres

619 Hotel Road, Deer Park, MD 21550

$229,900 | 808 M Street, Oakland, MD 21550
1/40

$229,900

2
Bedrooms
1,008
Square Feet
0.41
Acres

808 M Street, Oakland, MD 21550

$74,990 | 102 Roanoke Avenue, Oakland, MD 21550
1/43

$74,990

3
Bedrooms
1,932
Square Feet
0.28
Acres

102 Roanoke Avenue, Oakland, MD 21550

a view of a dry yard with wooden floor and a yard
1/27

$40,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.43
Acres

Yough View Drive, Oakland, MD 21550

a view of a house with a yard and tree s
1/55

$449,000

3
Bedrooms
2,160
Square Feet
1.14
Acres

482 Pergin Farm Road, Oakland, MD 21550

a view of a lush green forest with a lake
1/7

$65,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
4.91
Acres

Lot 4 Hunters Ridge Drive, Oakland, MD 21550

a view of a house with back yard and a patio
1/52
New Construction

$399,900

3
Bedrooms
1,464
Square Feet
0.69
Acres

1407 Broadford Road, Oakland, MD 21550

a view of a volley ball court
1/53

$920,000

3
Bedrooms
1,152
Square Feet
0.41
Acres

184 Upper Penn Point Drive, Oakland, MD 21550

$899,900 | 395 Woodlands Hill Lane, Oakland, MD 21550
1/66

$899,900

5
Bedrooms
3,160
Square Feet
2.03
Acres

395 Woodlands Hill Lane, Oakland, MD 21550

a view of a bunch of flowers and trees
1/16

$10,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.46
Acres

Lot 8 Stool Rock Road, Oakland, MD 21550

a house view with a outdoor space
1/61

$444,700

4
Bedrooms
1,585
Square Feet
0.41
Acres

333 Sloan Tract Road, Oakland, MD 21550

$1,199,000 | 20698 Garrett Highway, Oakland, MD 21550
1/52

$1,199,000

4
Bedrooms
1,844
Square Feet
0.28
Acres

20698 Garrett Highway, Oakland, MD 21550

an aerial view of a golf course with parking space
1/46

$489,900

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.5
Acres

Lot 7 Heron Cove West, Oakland, MD 21550

$165,000 | 14 Woodlands Hill Lane, Oakland, MD 21550
1/12

$165,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.04
Acres

14 Woodlands Hill Lane, Oakland, MD 21550

$137,500 | 24 Woodlands Hill Lane, Oakland, MD 21550
1/14

$137,500

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.53
Acres

24 Woodlands Hill Lane, Oakland, MD 21550

a view of a large yard with plants and large tree
1/6

$40,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
3.46
Acres

Grey Squirrel Road, Oakland, MD 21550

a view of empty room with wooden floor
1/124

$3,950,000

8
Bedrooms
6,486
Square Feet
1.53
Acres

1131 Lake Shore Drive, Oakland, MD 21550

a sign of golf club on a wall under a tree
1/59
Virtual Tour

$689,000

4
Bedrooms
2,402
Square Feet
0.63
Acres

180 Paradise Ridge Road, Oakland, MD 21550

a house view with a garden space
1/60
New Construction

$799,900

4
Bedrooms
Unavailable
Square Feet
0.64
Acres

15 Bryan Drive, Oakland, MD 21550

$375,000 | 18948 Garrett Highway, Oakland, MD 21550
1/41

$375,000

2
Bedrooms
1,404
Square Feet
1
Acres

18948 Garrett Highway, Oakland, MD 21550

a view of a sign in a field

$249,900

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
7.72
Acres

2560 Bray School Road, Oakland, MD 21550

a sign that is on the side of the road
1/6

$169,900

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.97
Acres

Mayhew Inn Road, Oakland, MD 21550

a front view of a house with garden
1/65

$460,000

5
Bedrooms
2,860
Square Feet
2.3
Acres

5154 Maryland Highway, Oakland, MD 21550

a city view from a balcony
1/24

$225,000

1
Bedrooms
Unavailable
Square Feet

565 Glendale Road, Unit 213, Oakland, MD 21550

$399,000 | 181 Glotfelty Drive, Oakland, MD 21550
1/51

$399,000

3
Bedrooms
1,456
Square Feet
1.29
Acres

181 Glotfelty Drive, Oakland, MD 21550

an aerial view of a house with a garden and yard
1/60

$365,000

5
Bedrooms
2,652
Square Feet
0.13
Acres

615 East Oak Street, Oakland, MD 21550

a front view of house with yard and green space
1/43

$169,000

3
Bedrooms
1,516
Square Feet
0.96
Acres

40 Sunshine Lane, Oakland, MD 21550

a front view of a house with garden
1/35

$174,900

2
Bedrooms
2,008
Square Feet
0.18
Acres

206 West Liberty Street, Oakland, MD 21550

a view of outdoor space and trees
1/4

$19,900

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.05
Acres

Bear Drive East, Oakland, MD 21550

$325,000 | 112 East Pennington Street, Oakland, MD 21550
1/55

$325,000

5
Bedrooms
2,165
Square Feet
0.12
Acres

112 East Pennington Street, Oakland, MD 21550

$769,000 | 325 Markwood Drive, Oakland, MD 21550
1/66

$769,000

4
Bedrooms
3,376
Square Feet
4.35
Acres

325 Markwood Drive, Oakland, MD 21550

front view of a house with a yard
1/44

$1,425,000

3
Bedrooms
1,695
Square Feet
0.45
Acres

187 Lower Penn Point Drive, Oakland, MD 21550

a view of a house with pool and chairs
1/29

$269,900

2
Bedrooms
1,400
Square Feet
Unavailable
Acres

5 Laurel Brook Drive, Unit 5, Oakland, MD 21550

$175,000 | Robinwood Drive, Unit 9, Oakland, MD 21550
1/6

$175,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
3.46
Acres

Robinwood Drive, Unit 9, Oakland, MD 21550

a view of outdoor space and yard
1/14

$149,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
3.29
Acres

16 Woodlands Hill Lane, Oakland, MD 21550

a view of a lake with a yard
1/22

$159,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.02
Acres

22 Woodlands Hill Lane, Oakland, MD 21550

a view of green landscape with trees in the background
1/21

$99,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.84
Acres

Robinwood Drive, Unit 13, Oakland, MD 21550

a front view of a house with a yard
1/62
Virtual Tour

$745,000

5
Bedrooms
2,200
Square Feet
0.17
Acres

943 Paradise Heights, Oakland, MD 21550

$569,000 | 97-acres Lot C 97-acres Road, Oakland, MD 21550
1/21

$569,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
97.57
Acres

97-acres Lot C 97-acres Road, Oakland, MD 21550

$899,000 | 17240 Garrett Highway, Oakland, MD 21550
1/104

$899,000

6
Bedrooms
5,547
Square Feet
10.33
Acres

17240 Garrett Highway, Oakland, MD 21550

a front view of a house with a yard
1/65
Virtual Tour

$464,900

3
Bedrooms
1,838
Square Feet
Unavailable
Acres

256 Jeffrey Lane, Unit 28, Oakland, MD 21550

a view of a house with a yard and garage
1/43

$259,900

3
Bedrooms
1,998
Square Feet
0.15
Acres

102 North 3rd Street, Oakland, MD 21550

$719,999 | 941 Mountainview Drive, Oakland, MD 21550
1/60
Virtual Tour

$719,999

4
Bedrooms
4,377
Square Feet
1.17
Acres

941 Mountainview Drive, Oakland, MD 21550

$550,000 | 193 Red Run Road, Unit 1B3, Oakland, MD 21550
1/57

$550,000

2
Bedrooms
1,340
Square Feet

193 Red Run Road, Unit 1B3, Oakland, MD 21550

a picture of a lake with a house in the background
1/32
Virtual Tour

$1,095,000

2
Bedrooms
2,914
Square Feet
64
Acres

826 G G Swauger Road, Oakland, MD 21550

a view of an outdoor space and a yard
1/26

$259,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
42
Acres

Lot B Loch Deer Road, Oakland, MD 21550

$175,000 | Lot 4 Lodestone Way, Oakland, MD 21550
1/20

$175,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.32
Acres

Lot 4 Lodestone Way, Oakland, MD 21550

$1,799,900 | 49 Greenstone Way, Oakland, MD 21550
1/88
New Construction

$1,799,900

6
Bedrooms
4,477
Square Feet
0.48
Acres

49 Greenstone Way, Oakland, MD 21550

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