Oakland Maryland Homes for Sale

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163 Mitchell Drive Oakland, MD MLS# MDGA2011294 - Image 1

163 Mitchell Drive Oakland, MD MLS# MDGA2011294 - Image 2

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163 Mitchell Drive Oakland, MD MLS# MDGA2011294 - Image 62

Virtual Tour

1 of 62

$289,000

Beds

2.1

Baths

2,242

Sq.Ft.

163 Mitchell Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

17848 Garrett Highway Oakland, MD MLS# MDGA2011286 - Image 1

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Virtual Tour

1 of 122

$1,700,000

6,477

Sq.Ft.

17848 Garrett Highway

Oakland, MD

Courtesy of RAILEY REALTY, INC.

449 S 3Rd Street Oakland, MD MLS# MDGA2011304 - Image 1

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1 of 68

$275,900

Beds

2.0

Baths

1,928

Sq.Ft.

449 S 3Rd Street

Oakland, MD

Courtesy of RAILEY REALTY, INC.

THE TIME TO SELL IS NOW!

Dennett Rd, 10.10 Acres To Oakland Dr Oakland, MD MLS# MDGA2011252 - Image 1

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Dennett Rd, 10.10 Acres To Oakland Dr Oakland, MD MLS# MDGA2011252 - Image 10

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Dennett Rd, 10.10 Acres To Oakland Dr Oakland, MD MLS# MDGA2011252 - Image 21

1 of 21

$160,000

Studio

Beds

0.0

Baths

Dennett Rd, 10.10 Acres To Oakland Dr

Oakland, MD

Courtesy of THE KW COLLECTIVE

141 Montana Lane Oakland, MD MLS# MDGA2011248 - Image 1

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1 of 57

$219,000

Beds

1.1

Baths

912

Sq.Ft.

141 Montana Lane

Oakland, MD

Courtesy of RAILEY REALTY, INC.

164 Grandview Drive Oakland, MD MLS# MDGA2011052 - Image 1

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Virtual Tour

1 of 54

$950,000

Beds

2.1

Baths

2,368

Sq.Ft.

164 Grandview Drive

Oakland, MD

Courtesy of TAYLOR-MADE DEEP CREEK SALES

654 N Bradley Lane Oakland, MD MLS# MDGA2011266 - Image 1

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654 N Bradley Lane Oakland, MD MLS# MDGA2011266 - Image 13

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654 N Bradley Lane Oakland, MD MLS# MDGA2011266 - Image 40

654 N Bradley Lane Oakland, MD MLS# MDGA2011266 - Image 41

New Construction

1 of 41

$424,900

Beds

2.0

Baths

1,464

Sq.Ft.

654 N Bradley Lane

Oakland, MD

Courtesy of TAYLOR-MADE DEEP CREEK SALES

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 1

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 2

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 3

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 4

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 5

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 6

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 7

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 8

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 9

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 10

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 11

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 12

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 13

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 14

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 15

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 16

233 Rhododendron Drive Oakland, MD MLS# MDGA2011228 - Image 17

1 of 17

$35,000

Studio

Beds

0.0

Baths

233 Rhododendron Drive

Oakland, MD

Courtesy of TAYLOR-MADE DEEP CREEK SALES

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 1

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 2

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 3

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N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 9

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N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 11

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 12

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 13

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 14

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 15

N 4Th Street Oakland, MD MLS# MDGA2011244 - Image 16

New Construction

1 of 16

$230,000

N 4Th Street

Oakland, MD

Courtesy of THE KW COLLECTIVE

505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 1

505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 2

505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 3

505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 4

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505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 7

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505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 11

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505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 37

505 Southern Pines Drive Oakland, MD MLS# MDGA2011242 - Image 38

Virtual Tour

1 of 38

$287,500

Beds

2.0

Baths

1,248

Sq.Ft.

505 Southern Pines Drive

Oakland, MD

Courtesy of TAYLOR-MADE DEEP CREEK SALES

401 Dave Turney Street Oakland, MD MLS# MDGA2011080 - Image 1

401 Dave Turney Street Oakland, MD MLS# MDGA2011080 - Image 2

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401 Dave Turney Street Oakland, MD MLS# MDGA2011080 - Image 9

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401 Dave Turney Street Oakland, MD MLS# MDGA2011080 - Image 14

401 Dave Turney Street Oakland, MD MLS# MDGA2011080 - Image 15

401 Dave Turney Street Oakland, MD MLS# MDGA2011080 - Image 16

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401 Dave Turney Street Oakland, MD MLS# MDGA2011080 - Image 61

1 of 61

$439,000

5,328

Sq.Ft.

401 Dave Turney Street

Oakland, MD

Courtesy of JASON MITCHELL GROUP

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 1

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 2

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 3

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 4

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 5

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 6

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 7

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 8

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 9

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 10

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 11

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820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 13

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 14

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 15

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 16

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 17

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 18

820 N 4Th Street Oakland, MD MLS# MDGA2011246 - Image 19

1 of 19

$40,000

Beds

1.0

Baths

782

Sq.Ft.

820 N 4Th Street

Oakland, MD

Courtesy of THE KW COLLECTIVE

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

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 56

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

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

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 71

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 72

62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 73

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62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182 - Image 75

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

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

1 of 77

$899,000

Beds

3.1

Baths

2,464

Sq.Ft.

62 Whispering Pines Lane

Oakland, MD

Courtesy of RAILEY REALTY, INC.

TBD 15.75 Acres Bethlehem Road Oakland, MD MLS# MDGA2011216 - Image 1

TBD 15.75 Acres Bethlehem Road Oakland, MD MLS# MDGA2011216 - Image 2

TBD 15.75 Acres Bethlehem Road Oakland, MD MLS# MDGA2011216 - Image 3

TBD 15.75 Acres Bethlehem Road Oakland, MD MLS# MDGA2011216 - Image 4

TBD 15.75 Acres Bethlehem Road Oakland, MD MLS# MDGA2011216 - Image 5

1 of 5

$89,900

Studio

Beds

0.0

Baths

TBD 15.75 Acres Bethlehem Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 1

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 2

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 3

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19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 35

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 36

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 37

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 38

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 39

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 40

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 41

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 42

19530 Garrett Highway Oakland, MD MLS# MDGA2010798 - Image 43

1 of 43

$2,500,000

7,200

Sq.Ft.

19530 Garrett Highway

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

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 6

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

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 10

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

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 12

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 13

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 14

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 15

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 16

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 17

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 18

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 19

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 20

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 21

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 22

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 23

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 25

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 26

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 35

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 37

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 38

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 39

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 40

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

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 42

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

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 48

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 49

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 50

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 51

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467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 53

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 54

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 55

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 56

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

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 58

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 59

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

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 61

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 62

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 63

467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164 - Image 64

1 of 64

$769,900

Beds

3.1

Baths

3,780

Sq.Ft.

467 Paradise Ridge Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 1

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 2

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 3

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 4

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 5

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 6

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 7

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 8

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 9

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 10

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 11

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 12

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 13

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 14

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 15

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 16

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 17

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 18

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 19

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 20

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 21

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 22

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 23

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 24

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 25

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 26

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 27

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 28

157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174 - Image 29

Virtual Tour

1 of 29

$297,000

Beds

1.0

Baths

550

Sq.Ft.

157 Jeffrey Lane # 21B

Oakland, MD

Courtesy of TAYLOR-MADE DEEP CREEK SALES

74 Parks Road Oakland, MD MLS# MDGA2011172 - Image 1

74 Parks Road Oakland, MD MLS# MDGA2011172 - Image 2

1 of 2

$64,900

Beds

1.0

Baths

792

Sq.Ft.

74 Parks Road

Oakland, MD

Courtesy of REAL BROKER, LLC

Lot 36 Fox Tail Rd Oakland, MD MLS# MDGA2011162 - Image 1

Lot 36 Fox Tail Rd Oakland, MD MLS# MDGA2011162 - Image 2

Lot 36 Fox Tail Rd Oakland, MD MLS# MDGA2011162 - Image 3

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Lot 36 Fox Tail Rd Oakland, MD MLS# MDGA2011162 - Image 17

Lot 36 Fox Tail Rd Oakland, MD MLS# MDGA2011162 - Image 18

1 of 18

$4,000

Studio

Beds

0.0

Baths

Lot 36 Fox Tail Rd

Oakland, MD

Courtesy of TAYLOR-MADE DEEP CREEK SALES

815 Chadderton School Road Oakland, MD MLS# MDGA2011092 - Image 1

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815 Chadderton School Road Oakland, MD MLS# MDGA2011092 - Image 108

815 Chadderton School Road Oakland, MD MLS# MDGA2011092 - Image 109

815 Chadderton School Road Oakland, MD MLS# MDGA2011092 - Image 110

Virtual Tour

1 of 110

$1,900,000

Beds

3.1

Baths

4,619

Sq.Ft.

815 Chadderton School Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

About Oakland

Listings in Oakland, MD: 208
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	51
$100K - 200K	26
$200K - 300K	30
$300K - 400K	22
$400K - 500K	12
$500K - 600K	7
$600K - 700K	8
$700K - 800K	12
$800K - 900K	6
$900K - 1M	7
$1M - Max	27

Homes for Sale by Type in Oakland, MD

Property Type	Count
Single Family	93
Townhouse	2
Condo	24
Commercial	16
Rental	6
Lots and Land	73
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 6/12/2026)

Find Properties in Oakland, MD

Oakland, MD Information

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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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