Oakland Maryland Homes for Sale

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Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 1

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 2

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 3

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 4

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 5

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 6

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 7

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 8

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 9

Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036 - Image 10

Virtual Tour

1 of 10

$995,000

Studio

Beds

0.0

Baths

Glendale Rd Lot 12 Alpine Village Subdivision

Oakland, MD

Courtesy of RAILEY REALTY, INC.

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 1

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 2

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 3

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 4

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 5

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 6

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 7

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 8

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 9

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 10

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 11

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 12

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 13

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 14

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 15

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 16

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 17

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 18

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 19

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 20

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 21

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 23

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 24

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 25

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 26

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 27

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 28

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 29

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 30

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 31

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 35

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 36

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 37

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 38

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 39

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 40

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 41

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 42

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 43

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 44

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 45

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 47

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 48

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 49

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 50

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 61

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 62

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 63

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 64

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 65

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 66

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 67

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 76

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 77

Recently Listed

1 of 77

$930,000

Beds

3.1

Baths

2,464

Sq.Ft.

62 Whispering Pines Lane

Oakland, MD

Courtesy of RAILEY REALTY, INC.

267 San Francisco Street Oakland, MD MLS# MDGA2011040 - Image 1

267 San Francisco Street Oakland, MD MLS# MDGA2011040 - Image 2

267 San Francisco Street Oakland, MD MLS# MDGA2011040 - Image 3

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267 San Francisco Street Oakland, MD MLS# MDGA2011040 - Image 30

1 of 30

$899,900

Beds

2.1

Baths

3,278

Sq.Ft.

267 San Francisco Street

Oakland, MD

Courtesy of HOMESMART

THE TIME TO SELL IS NOW!

139 Overlook Ridge Drive Oakland, MD MLS# MDGA2009000 - Image 1

139 Overlook Ridge Drive Oakland, MD MLS# MDGA2009000 - Image 2

139 Overlook Ridge Drive Oakland, MD MLS# MDGA2009000 - Image 3

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1 of 73

$875,000

Beds

4.1

Baths

2,846

Sq.Ft.

139 Overlook Ridge Drive

Oakland, MD

Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE

39 Leo Friend Road Oakland, MD MLS# MDGA2010444 - Image 1

39 Leo Friend Road Oakland, MD MLS# MDGA2010444 - Image 2

39 Leo Friend Road Oakland, MD MLS# MDGA2010444 - Image 3

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1 of 33

OPEN HOUSE: Saturday 3/7 2:00 PM - 4:00 PM

$875,000

Beds

3.1

Baths

3,897

Sq.Ft.

39 Leo Friend Road

Oakland, MD

Courtesy of THE KW COLLECTIVE

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 1

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 2

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1 of 85

$865,000

Beds

4.1

Baths

2,970

Sq.Ft.

1909 Pysell Crosscut Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

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

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 74

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 77

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

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14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 90

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 91

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 92

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 93

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 94

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 95

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 96

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 97

14 Commerce Drive Oakland, MD MLS# MDGA2010002 - Image 98

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.

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 1

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 2

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 3

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 4

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 5

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 7

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 8

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 9

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 11

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 41

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 43

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 44

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 45

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 46

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 47

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 57

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 60

Recently Listed

1 of 60

$799,900

Beds

3.1

Baths

3,780

Sq.Ft.

467 Paradise Ridge Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

1001 Sutter Lane Oakland, MD MLS# MDGA2010778 - Image 1

1001 Sutter Lane Oakland, MD MLS# MDGA2010778 - Image 2

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1001 Sutter Lane Oakland, MD MLS# MDGA2010778 - Image 92

1001 Sutter Lane Oakland, MD MLS# MDGA2010778 - Image 93

1001 Sutter Lane Oakland, MD MLS# MDGA2010778 - Image 94

Virtual Tour

1 of 94

$799,000

Beds

4.2

Baths

6,550

Sq.Ft.

1001 Sutter Lane

Oakland, MD

Courtesy of RAILEY REALTY, INC.

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 7

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 8

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1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 41

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 42

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1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 47

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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 59

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1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 61

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 62

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 63

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 64

1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078 - Image 65

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 REAL ESTATE

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

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

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519 Paradise Heights Oakland, MD MLS# MDGA2010792 - Image 14

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

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

25 Silver Tree Lane Oakland, MD MLS# MDGA2009038 - Image 48

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 REAL ESTATE

130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 1

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130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 73

130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 74

130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 75

130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 76

130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 77

130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 78

130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146 - Image 79

1 of 79

$749,000

Beds

3.0

Baths

1,900

Sq.Ft.

130 Timberloft Circle # 14

Oakland, MD

Courtesy of RAILEY REALTY, INC.

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 1

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 2

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 3

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 4

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 5

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 6

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 7

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 8

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 9

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 10

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 11

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 12

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 13

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 14

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 15

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 16

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 17

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 18

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 19

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Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 25

Memorial Drive Oakland, MD MLS# MDGA2010668 - Image 26

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

621 Paradise Heights Oakland, MD MLS# MDGA2008332 - Image 2

621 Paradise Heights Oakland, MD MLS# MDGA2008332 - Image 3

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621 Paradise Heights Oakland, MD MLS# MDGA2008332 - Image 113

621 Paradise Heights Oakland, MD MLS# MDGA2008332 - Image 114

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621 Paradise Heights Oakland, MD MLS# MDGA2008332 - Image 116

621 Paradise Heights Oakland, MD MLS# MDGA2008332 - Image 117

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.

4A Mystic Creek Trail Oakland, MD MLS# MDGA2010920 - Image 1

4A Mystic Creek Trail Oakland, MD MLS# MDGA2010920 - Image 2

4A Mystic Creek Trail Oakland, MD MLS# MDGA2010920 - Image 3

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4A Mystic Creek Trail Oakland, MD MLS# MDGA2010920 - Image 50

New Construction

1 of 50

$679,900

Beds

4.1

Baths

3,000

Sq.Ft.

4A Mystic Creek Trail

Oakland, MD

Courtesy of RAILEY REALTY, INC.

George Washington Highway Oakland, MD MLS# MDGA2010274 - Image 1

George Washington Highway Oakland, MD MLS# MDGA2010274 - Image 2

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George Washington Highway Oakland, MD MLS# MDGA2010274 - Image 14

George Washington Highway Oakland, MD MLS# MDGA2010274 - Image 15

George Washington Highway Oakland, MD MLS# MDGA2010274 - Image 16

1 of 16

$675,000

Studio

Beds

0.0

Baths

George Washington Highway

Oakland, MD

Courtesy of THE KW COLLECTIVE

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

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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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1 of 10

$649,000

Studio

Beds

0.0

Baths

13209 Garrett Highway

Oakland, MD

Courtesy of RAILEY REALTY, INC.

130 Mystic Creek Trail # 1B Oakland, MD MLS# MDGA2011072 - Image 1

130 Mystic Creek Trail # 1B Oakland, MD MLS# MDGA2011072 - Image 2

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130 Mystic Creek Trail # 1B Oakland, MD MLS# MDGA2011072 - Image 70

130 Mystic Creek Trail # 1B Oakland, MD MLS# MDGA2011072 - Image 71

Virtual Tour

1 of 71

$639,000

Beds

4.1

Baths

2,200

Sq.Ft.

130 Mystic Creek Trail # 1B

Oakland, MD

Courtesy of RAILEY REALTY, INC.

About Oakland

Listings in Oakland, MD: 157
Estimated median home price: $295,000

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	36
$100K - 200K	19
$200K - 300K	30
$300K - 400K	13
$400K - 500K	7
$500K - 600K	10
$600K - 700K	10
$700K - 800K	7
$800K - 900K	4
$900K - 1M	2
$1M - Max	19

Homes for Sale by Type in Oakland, MD

Property Type	Count
Single Family	65
Townhouse	2
Condo	22
Commercial	13
Rental	6
Lots and Land	55
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 3/6/2026)

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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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