Oakland Maryland Homes for Sale

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 1

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 2

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 3

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 4

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 6

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 7

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 8

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 9

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 11

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 13

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 14

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 16

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 18

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 19

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 20

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 21

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 27

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 50

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 56

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 60

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 76

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 78

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 81

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 99

1 of 99

$800,000

10,000

Sq.Ft.

14 Commerce Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 1

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 2

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 3

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 4

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 5

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 7

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 8

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 9

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 10

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 11

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 15

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 16

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 35

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 37

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 38

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 41

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 42

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 46

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 47

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 49

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 51

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 53

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222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 55

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 56

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 57

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 58

222 Skippers Point Road Oakland, MD MLS# MDGA2010764 - Image 59

1 of 59

$779,000

Beds

1.1

Baths

1,278

Sq.Ft.

222 Skippers Point Road

Oakland, MD

Courtesy of THE KW COLLECTIVE

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 1

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 2

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 3

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 4

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 5

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198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 7

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 8

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 9

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198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 11

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 12

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198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 14

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 15

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 16

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198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 25

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 26

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198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 28

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198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 31

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198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 33

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 34

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 35

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 36

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 37

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 38

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 39

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 40

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 41

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 42

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 43

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 44

198 Grandview Drive Oakland, MD MLS# MDGA2010020 - Image 45

Virtual Tour

1 of 45

$775,000

Beds

3.0

Baths

2,744

Sq.Ft.

198 Grandview Drive

Oakland, MD

Courtesy of RE/MAX ONE

THE TIME TO SELL IS NOW!

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 1

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 2

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 3

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1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 12

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1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 54

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 55

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 56

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1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 58

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 59

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1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 66

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 67

1 of 67

$769,000

Beds

5.0

Baths

3,664

Sq.Ft.

1875 Pysell Crosscut Road

Oakland, MD

Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES

939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 1

939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 2

939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 3

939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 4

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939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 13

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939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 16

939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 17

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939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 19

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939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 28

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939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096 - Image 30

1 of 30

$765,000

Beds

2.0

Baths

1,432

Sq.Ft.

939 Glendale Road # 19

Oakland, MD

Courtesy of RICHARD DAVIS & ASSOCIATES

519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 1

519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 2

519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 3

519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 4

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519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 15

519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 16

519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 17

1 of 17

$765,000

Beds

3.0

Baths

2,112

Sq.Ft.

519 Paradise Heights

Oakland, MD

Courtesy of APPALACHIAN REALTY

329 Lemley Drive Oakland, MD MLS# MDGA2010512 - Image 1

329 Lemley Drive Oakland, MD MLS# MDGA2010512 - Image 2

329 Lemley Drive Oakland, MD MLS# MDGA2010512 - Image 3

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329 Lemley Drive Oakland, MD MLS# MDGA2010512 - Image 81

Virtual Tour

1 of 81

$750,000

Beds

3.1

Baths

2,632

Sq.Ft.

329 Lemley Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

220 Woodlands Hill Lane Oakland, MD MLS# MDGA2010752 - Image 1

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Virtual Tour

1 of 85

$750,000

Beds

3.0

Baths

2,660

Sq.Ft.

220 Woodlands Hill Lane

Oakland, MD

Courtesy of RE/MAX REALTY GROUP

25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 1

25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 2

25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 3

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25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 47

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25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 49

25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 50

25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 51

25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 52

Virtual Tour

1 of 52

$749,900

Beds

4.0

Baths

2,364

Sq.Ft.

25 Silver Tree Lane

Oakland, MD

Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 1

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1 of 26

$699,000

Studio

Beds

0.0

Baths

Memorial Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

621 Paradise Heights Oakland, MD MLS# MDGA2008332 - Image 1

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Virtual Tour

1 of 117

$695,000

Beds

3.0

Baths

3,242

Sq.Ft.

621 Paradise Heights

Oakland, MD

Courtesy of RAILEY REALTY, INC.

155 Basswood Way Oakland, MD MLS# MDGA2009018 - Image 1

155 Basswood Way Oakland, MD MLS# MDGA2009018 - Image 2

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Virtual Tour

1 of 54

$674,900

Beds

3.0

Baths

2,792

Sq.Ft.

155 Basswood Way

Oakland, MD

Courtesy of RAILEY REALTY, INC.

13209 Garrett Highway Oakland, MD MLS# MDGA2006142 - Image 1

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13209 Garrett Highway Oakland, MD MLS# MDGA2006142 - Image 6

1 of 6

$649,000

13209 Garrett Highway

Oakland, MD

Courtesy of RAILEY REALTY, INC.

13209 Garrett Highway Oakland, MD MLS# MDGA2008426 - Image 1

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13209 Garrett Highway Oakland, MD MLS# MDGA2008426 - Image 6

13209 Garrett Highway Oakland, MD MLS# MDGA2008426 - Image 7

13209 Garrett Highway Oakland, MD MLS# MDGA2008426 - Image 8

13209 Garrett Highway Oakland, MD MLS# MDGA2008426 - Image 9

13209 Garrett Highway Oakland, MD MLS# MDGA2008426 - Image 10

1 of 10

$649,000

Studio

Beds

0.0

Baths

13209 Garrett Highway

Oakland, MD

Courtesy of RAILEY REALTY, INC.

1118 Lake Shore Drive Oakland, MD MLS# MDGA2008542 - Image 1

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1118 Lake Shore Drive Oakland, MD MLS# MDGA2008542 - Image 101

Virtual Tour

1 of 101

$649,000

Beds

2.0

Baths

2,446

Sq.Ft.

1118 Lake Shore Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

65 Village Drive # 6 Oakland, MD MLS# MDGA2008728 - Image 1

65 Village Drive # 6 Oakland, MD MLS# MDGA2008728 - Image 2

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Virtual Tour

1 of 55

$625,000

Beds

3.0

Baths

1,740

Sq.Ft.

65 Village Drive # 6

Oakland, MD

Courtesy of RAILEY REALTY, INC.

66 Paradise Ridge Road Oakland, MD MLS# MDGA2010278 - Image 1

66 Paradise Ridge Road Oakland, MD MLS# MDGA2010278 - Image 2

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1 of 24

$619,900

Beds

4.0

Baths

2,550

Sq.Ft.

66 Paradise Ridge Road

Oakland, MD

Courtesy of HAWKINS REAL ESTATE COMPANY

2701 Old Crellin Road Oakland, MD MLS# MDGA2007826 - Image 1

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1 of 63

$600,000

4,700

Sq.Ft.

2701 Old Crellin Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

3084 Lake Shore Drive Oakland, MD MLS# MDGA2008870 - Image 1

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3084 Lake Shore Drive Oakland, MD MLS# MDGA2008870 - Image 71

Virtual Tour

1 of 71

$599,900

Beds

3.0

Baths

2,464

Sq.Ft.

3084 Lake Shore Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

433 San Francisco Street Oakland, MD MLS# MDGA2009232 - Image 1

433 San Francisco Street Oakland, MD MLS# MDGA2009232 - Image 2

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433 San Francisco Street Oakland, MD MLS# MDGA2009232 - Image 66

Virtual Tour

1 of 66

$599,900

Beds

2.1

Baths

2,560

Sq.Ft.

433 San Francisco Street

Oakland, MD

Courtesy of RAILEY REALTY, INC.

About Oakland

Listings in Oakland, MD: 155
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	33
$100K - 200K	23
$200K - 300K	23
$300K - 400K	12
$400K - 500K	9
$500K - 600K	12
$600K - 700K	8
$700K - 800K	9
$800K - 900K	4
$900K - 1M	3
$1M - Max	19

Homes for Sale by Type in Oakland, MD

Property Type	Count
Single Family	64
Townhouse	0
Condo	21
Commercial	10
Rental	4
Lots and Land	60
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 12/27/2025)

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21550

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 Reciprocity^SM 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.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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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