182 total properties
Did you mean the neighborhood Oakland?
View 47 Holy Cross Oakland, MD MLS# MDGA2010560
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Save 47 Holy Cross Oakland, MD MLS# MDGA2010560
1 of 112
$6,499,900
8

Beds

8.1

Baths

11,417

Sq.Ft.

47 Holy Cross

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
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 1010 Holy Cross Drive Oakland, MD MLS# MDGA2011388
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Save 1010 Holy Cross Drive Oakland, MD MLS# MDGA2011388
1 of 147
$5,150,000
8

Beds

8.1

Baths

10,300

Sq.Ft.

1010 Holy Cross Drive

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
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
$3,690,000
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 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 19530 Garrett Highway Oakland, MD MLS# MDGA2010798
Save 19530 Garrett Highway Oakland, MD MLS# MDGA2010798
1 of 43
$2,500,000
7,200

Sq.Ft.

19530 Garrett Highway

Oakland, MD

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View 2411 Lake Shore Drive Oakland, MD MLS# MDGA2011610
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1 of 69
$2,390,000
5

Beds

4.0

Baths

3,463

Sq.Ft.

2411 Lake Shore Drive

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 REAL ESTATE
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 1038 S Blakeslee Road Oakland, MD MLS# MDGA2011370
Save 1038 S Blakeslee Road Oakland, MD MLS# MDGA2011370
1 of 69
$2,100,000
5

Beds

5.0

Baths

4,074

Sq.Ft.

1038 S Blakeslee Road

Oakland, MD

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Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
View 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
Save 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
1 of 110
$1,900,000
5

Beds

3.1

Baths

4,619

Sq.Ft.

815 Chadderton School Road

Oakland, MD

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View 62 Duck Cove Road Oakland, MD MLS# MDGA2011402
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Save 62 Duck Cove Road Oakland, MD MLS# MDGA2011402
1 of 74
$1,899,000
4

Beds

4.0

Baths

4,150

Sq.Ft.

62 Duck Cove Road

Oakland, MD

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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 1544 Stockslager Road Oakland, MD MLS# MDGA2011420
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Save 1544 Stockslager Road Oakland, MD MLS# MDGA2011420
1 of 64
$1,750,000
5

Beds

4.0

Baths

3,456

Sq.Ft.

1544 Stockslager Road

Oakland, MD

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Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
View 17848 Garrett Highway Oakland, MD MLS# MDGA2011286
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$1,700,000
6,477

Sq.Ft.

17848 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
$1,650,000
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 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
Save 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
1 of 74
$1,399,000
3

Beds

2.0

Baths

2,064

Sq.Ft.

2332 Paradise Point Road

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 660 Glendale Road Oakland, MD MLS# MDGA2011188
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Save 660 Glendale Road Oakland, MD MLS# MDGA2011188
1 of 62
$1,300,000
5

Beds

3.0

Baths

2,592

Sq.Ft.

660 Glendale Road

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
$1,149,800
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

About Oakland

Listings in Oakland, MD

182

Estimated median home price

$297,000
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 44
$100K - 200K 20
$200K - 300K 32
$300K - 400K 20
$400K - 500K 8
$500K - 600K 9
$600K - 700K 10
$700K - 800K 8
$800K - 900K 6
$900K - 1M 3
$1M - Max 22

Homes for Sale by Type in Oakland, MD

Property Type Count
Single Family 80
Townhouse 2
Condo 24
Commercial 14
Rental 6
Lots and Land 62
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 4/22/2026)

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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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