164 total properties
Did you mean the neighborhood Oakland?
View 1240 Boy Scout Road Oakland, MD MLS# MDGA2008536
  • Virtual Tour
Save 1240 Boy Scout Road Oakland, MD MLS# MDGA2008536
1 of 149
$4,390,000
7

Beds

5.2

Baths

5,695

Sq.Ft.

1240 Boy Scout Road

Oakland, MD

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Courtesy of THE KW COLLECTIVE
View 282 Mccomas Beach Terrace Oakland, MD MLS# MDGA2010518
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Save 282 Mccomas Beach Terrace Oakland, MD MLS# MDGA2010518
1 of 150
$4,200,000
6

Beds

5.1

Baths

4,354

Sq.Ft.

282 Mccomas Beach Terrace

Oakland, MD

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Courtesy of HUNT COUNTRY SOTHEBY'S INTERNATIONAL REALTY
View 56 Bee Tree Lane Oakland, MD MLS# MDGA2009212
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Save 56 Bee Tree Lane Oakland, MD MLS# MDGA2009212
1 of 141
$2,845,000
6

Beds

7.1

Baths

5,100

Sq.Ft.

56 Bee Tree Lane

Oakland, MD

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The time to sell is now! THE TIME TO SELL IS NOW!
View 65 Enterprise Drive Oakland, MD MLS# MDGA2010098
Save 65 Enterprise Drive Oakland, MD MLS# MDGA2010098
1 of 67
$2,799,900
30,000

Sq.Ft.

65 Enterprise Drive

Oakland, MD

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View 41 Boyd Paugh Lane Oakland, MD MLS# MDGA2007342
Save 41 Boyd Paugh Lane Oakland, MD MLS# MDGA2007342
1 of 103
$2,399,000
7

Beds

5.0

Baths

4,691

Sq.Ft.

41 Boyd Paugh Lane

Oakland, MD

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View 2725 Stockslager Road Oakland, MD MLS# MDGA2008312
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Save 2725 Stockslager Road Oakland, MD MLS# MDGA2008312
1 of 115
$2,350,000
5

Beds

6.1

Baths

5,376

Sq.Ft.

2725 Stockslager Road

Oakland, MD

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Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
View 12743 Garrett Highway Oakland, MD MLS# MDGA2008424
Save 12743 Garrett Highway Oakland, MD MLS# MDGA2008424
1 of 62
$1,999,900
32,544

Sq.Ft.

12743 Garrett Highway

Oakland, MD

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View 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
Save 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
1 of 31
$1,800,000
4

Beds

4.2

Baths

5,117

Sq.Ft.

3898 3898 Underwood Rd

Oakland, MD

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Courtesy of CUSTER REALTY & AUCTION
View 499 Oakland Drive Oakland, MD MLS# MDGA2003394
Save 499 Oakland Drive Oakland, MD MLS# MDGA2003394
1 of 103
$1,750,000
15,000

Sq.Ft.

499 Oakland Drive

Oakland, MD

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View 272 Mccomas Beach Terrace Oakland, MD MLS# MDGA2010302
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Save 272 Mccomas Beach Terrace Oakland, MD MLS# MDGA2010302
1 of 71
$1,589,000
5

Beds

3.1

Baths

2,448

Sq.Ft.

272 Mccomas Beach Terrace

Oakland, MD

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View 336 Paradise Heights Oakland, MD MLS# MDGA2010378
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Save 336 Paradise Heights Oakland, MD MLS# MDGA2010378
1 of 94
$1,499,000
5

Beds

3.0

Baths

2,826

Sq.Ft.

336 Paradise Heights

Oakland, MD

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View 439 Paradise Heights Oakland, MD MLS# MDGA2008472
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Save 439 Paradise Heights Oakland, MD MLS# MDGA2008472
1 of 45
$1,329,000
6

Beds

4.1

Baths

4,113

Sq.Ft.

439 Paradise Heights

Oakland, MD

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View 19956 Garrett Highway # 6 Oakland, MD MLS# MDGA2009898
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Save 19956 Garrett Highway # 6 Oakland, MD MLS# MDGA2009898
1 of 81
$1,289,000
4

Beds

4.0

Baths

3,000

Sq.Ft.

19956 Garrett Highway # 6

Oakland, MD

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View 444 Woodlands Hill Lane Oakland, MD MLS# MDGA2010802
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Save 444 Woodlands Hill Lane Oakland, MD MLS# MDGA2010802
1 of 68
$1,199,990
4

Beds

4.2

Baths

4,744

Sq.Ft.

444 Woodlands Hill Lane

Oakland, MD

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View 127 Paradise Heights Oakland, MD MLS# MDGA2009010
Save 127 Paradise Heights Oakland, MD MLS# MDGA2009010
1 of 58
$1,100,000
3

Beds

2.1

Baths

2,240

Sq.Ft.

127 Paradise Heights

Oakland, MD

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View 1720 Pysell Crosscut Road Oakland, MD MLS# MDGA2010210
Save 1720 Pysell Crosscut Road Oakland, MD MLS# MDGA2010210
1 of 114
$999,999
5

Beds

5.1

Baths

8,000

Sq.Ft.

1720 Pysell Crosscut Road

Oakland, MD

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View 340 Grandview Drive Oakland, MD MLS# MDGA2010536
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Save 340 Grandview Drive Oakland, MD MLS# MDGA2010536
1 of 87
$949,900
6

Beds

4.0

Baths

2,536

Sq.Ft.

340 Grandview Drive

Oakland, MD

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View 39 Leo Friend Road Oakland, MD MLS# MDGA2010444
Save 39 Leo Friend Road Oakland, MD MLS# MDGA2010444
1 of 33
$919,000
3

Beds

3.1

Baths

3,897

Sq.Ft.

39 Leo Friend Road

Oakland, MD

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View 139 Overlook Ridge Drive Oakland, MD MLS# MDGA2009000
Save 139 Overlook Ridge Drive Oakland, MD MLS# MDGA2009000
1 of 73
$875,000
5

Beds

4.1

Baths

2,846

Sq.Ft.

139 Overlook Ridge Drive

Oakland, MD

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View 1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462
Save 1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462
1 of 85
$865,000
4

Beds

4.1

Baths

2,970

Sq.Ft.

1909 Pysell Crosscut Road

Oakland, MD

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About Oakland

Listings in Oakland, MD

167

Estimated median home price

$299,500
Oakland MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Oakland, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Oakland, MD.

Homes for Sale by Price in Oakland, MD

Price Count
$0 - 100K 38
$100K - 200K 24
$200K - 300K 23
$300K - 400K 13
$400K - 500K 12
$500K - 600K 12
$600K - 700K 8
$700K - 800K 11
$800K - 900K 4
$900K - 1M 4
$1M - Max 18

Homes for Sale by Type in Oakland, MD

Property Type Count
Single Family 68
Townhouse 0
Condo 24
Commercial 10
Rental 1
Lots and Land 65
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 12/9/2025)

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Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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