158 total properties
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View 47 Holy Cross Oakland, MD MLS# MDGA2010560
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Save 47 Holy Cross Oakland, MD MLS# MDGA2010560
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$6,499,900
8

Beds

8.1

Baths

11,417

Sq.Ft.

47 Holy Cross

Oakland, MD

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View 4009 Mayhew Inn Oakland, MD MLS# MDGA2007236
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$6,000,000

4009 Mayhew Inn

Oakland, MD

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Courtesy of JASON MITCHELL GROUP
View 1240 Boy Scout Road Oakland, MD MLS# MDGA2008536
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1 of 150
$4,250,000
7

Beds

5.2

Baths

5,695

Sq.Ft.

1240 Boy Scout Road

Oakland, MD

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Courtesy of THE KW COLLECTIVE
The time to sell is now! THE TIME TO SELL IS NOW!
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 255 Thornberry Road Oakland, MD MLS# MDGA2010918
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Save 255 Thornberry Road Oakland, MD MLS# MDGA2010918
1 of 122
$3,100,000
4

Beds

3.1

Baths

3,883

Sq.Ft.

255 Thornberry Road

Oakland, MD

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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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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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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 209 Glendale Road Oakland, MD MLS# MDGA2010922
Save 209 Glendale Road Oakland, MD MLS# MDGA2010922
1 of 89
$2,100,000
6

Beds

4.1

Baths

3,882

Sq.Ft.

209 Glendale Road

Oakland, MD

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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 1019 Lake Shore Drive Oakland, MD MLS# MDGA2010014
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Save 1019 Lake Shore Drive Oakland, MD MLS# MDGA2010014
1 of 75
$1,749,000
4

Beds

4.1

Baths

2,605

Sq.Ft.

1019 Lake Shore Drive

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
$1,449,000
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
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$1,329,000
6

Beds

4.1

Baths

4,113

Sq.Ft.

439 Paradise Heights

Oakland, MD

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View 444 Woodlands Hill Lane Oakland, MD MLS# MDGA2010802
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 285 Lake Shore Drive Oakland, MD MLS# MDGA2010466
Save 285 Lake Shore Drive Oakland, MD MLS# MDGA2010466
1 of 47
$1,199,000
5

Beds

4.1

Baths

2,593

Sq.Ft.

285 Lake Shore Drive

Oakland, MD

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Courtesy of KELLER WILLIAMS CAPITAL PROPERTIES
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 Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
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Save Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
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$995,000
Studio

Beds

0.0

Baths

Glendale Rd Lot 12 Alpine Village Subdivision

Oakland, MD

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About Oakland

Listings in Oakland, MD

158

Estimated median home price

$284,950
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 36
$100K - 200K 24
$200K - 300K 23
$300K - 400K 14
$400K - 500K 9
$500K - 600K 10
$600K - 700K 9
$700K - 800K 6
$800K - 900K 5
$900K - 1M 4
$1M - Max 18

Homes for Sale by Type in Oakland, MD

Property Type Count
Single Family 66
Townhouse 1
Condo 20
Commercial 10
Rental 4
Lots and Land 61
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 1/28/2026)

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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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Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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