Oakland Maryland Homes for Sale

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340 Grandview Drive Oakland, MD MLS# MDGA2010536 - Image 1

340 Grandview Drive Oakland, MD MLS# MDGA2010536 - Image 2

340 Grandview Drive Oakland, MD MLS# MDGA2010536 - Image 3

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340 Grandview Drive Oakland, MD MLS# MDGA2010536 - Image 84

Virtual Tour

1 of 84

$949,900

Beds

4.0

Baths

2,536

Sq.Ft.

340 Grandview Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

Crosby Drive # 64/65 Oakland, MD MLS# MDGA2010542 - Image 1

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Crosby Drive # 64/65 Oakland, MD MLS# MDGA2010542 - Image 54

Crosby Drive # 64/65 Oakland, MD MLS# MDGA2010542 - Image 55

New Construction

1 of 55

$550,000

Beds

2.0

Baths

1,986

Sq.Ft.

Crosby Drive # 64/65

Oakland, MD

Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES

1989 Lake Shore Drive Oakland, MD MLS# MDGA2010492 - Image 1

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1 of 76

$1,499,000

Beds

3.1

Baths

3,008

Sq.Ft.

1989 Lake Shore Drive

Oakland, MD

Courtesy of RAILEY REALTY, INC.

THE TIME TO SELL IS NOW!

282 Mccomas Beach Terrace Oakland, MD MLS# MDGA2010518 - Image 1

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New Construction with Virtual Tour

1 of 150

$4,200,000

Beds

5.1

Baths

4,354

Sq.Ft.

282 Mccomas Beach Terrace

Oakland, MD

Courtesy of HUNT COUNTRY SOTHEBY'S INTERNATIONAL REALTY

77 Meadow Court Oakland, MD MLS# MDGA2010516 - Image 1

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77 Meadow Court Oakland, MD MLS# MDGA2010516 - Image 64

77 Meadow Court Oakland, MD MLS# MDGA2010516 - Image 65

Virtual Tour

1 of 65

$599,900

Beds

3.0

Baths

2,436

Sq.Ft.

77 Meadow Court

Oakland, MD

Courtesy of RAILEY REALTY, INC.

102 Roanoke Avenue Oakland, MD MLS# MDGA2010452 - Image 1

102 Roanoke Avenue Oakland, MD MLS# MDGA2010452 - Image 2

102 Roanoke Avenue Oakland, MD MLS# MDGA2010452 - Image 3

102 Roanoke Avenue Oakland, MD MLS# MDGA2010452 - Image 4

102 Roanoke Avenue Oakland, MD MLS# MDGA2010452 - Image 5

102 Roanoke Avenue Oakland, MD MLS# MDGA2010452 - Image 6

102 Roanoke Avenue Oakland, MD MLS# MDGA2010452 - Image 7

1 of 7

$130,000

Beds

1.1

Baths

1,932

Sq.Ft.

102 Roanoke Avenue

Oakland, MD

Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 1

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 2

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 3

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 4

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111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 6

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 7

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 8

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 9

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 10

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 11

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 12

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 13

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 14

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 15

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 16

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 17

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 18

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 19

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 20

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 21

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 22

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 23

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 24

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 25

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 26

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 27

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 28

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111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 30

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 31

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 32

111 Knoll Crest Heights Drive Oakland, MD MLS# MDGA2010522 - Image 33

1 of 33

$189,900

Beds

2.0

Baths

3,504

Sq.Ft.

111 Knoll Crest Heights Drive

Oakland, MD

Courtesy of 1 REAL ESTATE SOURCE LLC

5024 Cranesville Road Oakland, MD MLS# MDGA2010510 - Image 1

5024 Cranesville Road Oakland, MD MLS# MDGA2010510 - Image 2

5024 Cranesville Road Oakland, MD MLS# MDGA2010510 - Image 3

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5024 Cranesville Road Oakland, MD MLS# MDGA2010510 - Image 65

5024 Cranesville Road Oakland, MD MLS# MDGA2010510 - Image 66

5024 Cranesville Road Oakland, MD MLS# MDGA2010510 - Image 67

Virtual Tour

1 of 67

$475,000

Beds

2.1

Baths

2,128

Sq.Ft.

5024 Cranesville Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

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

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329 Lemley Drive Oakland, MD MLS# MDGA2010512 - Image 78

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329 Lemley Drive Oakland, MD MLS# MDGA2010512 - Image 80

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.

3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508 - Image 1

3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508 - Image 2

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3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508 - Image 31

1 of 31

$1,800,000

Beds

4.2

Baths

5,117

Sq.Ft.

3898 3898 Underwood Rd

Oakland, MD

Courtesy of CUSTER REALTY & AUCTION

9 Timber Falls Road Oakland, MD MLS# MDGA2010352 - Image 1

9 Timber Falls Road Oakland, MD MLS# MDGA2010352 - Image 2

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9 Timber Falls Road Oakland, MD MLS# MDGA2010352 - Image 24

9 Timber Falls Road Oakland, MD MLS# MDGA2010352 - Image 25

1 of 25

$34,000

Studio

Beds

0.0

Baths

9 Timber Falls Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

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

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

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 3

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1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 75

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 76

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 77

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 78

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 79

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 80

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 81

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 82

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 83

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 84

1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462 - Image 85

1 of 85

$865,000

Beds

4.1

Baths

2,970

Sq.Ft.

1909 Pysell Crosscut Road

Oakland, MD

Courtesy of RAILEY REALTY, INC.

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

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

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1 of 33

$919,000

Beds

3.1

Baths

3,897

Sq.Ft.

39 Leo Friend Road

Oakland, MD

Courtesy of THE KW COLLECTIVE

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 1

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 2

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 3

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 4

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 5

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0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 8

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 9

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0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 11

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 12

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 13

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 14

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 15

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 16

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 17

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 18

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0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 20

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 21

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 22

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 23

0 Lake Shore Drive Oakland, MD MLS# MDGA2010464 - Image 24

1 of 24

$279,900

Studio

Beds

0.0

Baths

0 Lake Shore Drive

Oakland, MD

Courtesy of THE MIKE HAYWOOD GROUP

697 Monte Vista Road Oakland, MD MLS# MDGA2010454 - Image 1

697 Monte Vista Road Oakland, MD MLS# MDGA2010454 - Image 2

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697 Monte Vista Road Oakland, MD MLS# MDGA2010454 - Image 56

Virtual Tour

1 of 56

$359,000

Beds

3.1

Baths

3,682

Sq.Ft.

697 Monte Vista Road

Oakland, MD

Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES

961 Cedar Lane Oakland, MD MLS# MDGA2010426 - Image 1

961 Cedar Lane Oakland, MD MLS# MDGA2010426 - Image 2

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961 Cedar Lane Oakland, MD MLS# MDGA2010426 - Image 50

1 of 50

$379,000

Beds

2.1

Baths

1,920

Sq.Ft.

961 Cedar Lane

Oakland, MD

Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES

lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 1

lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 2

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lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 4

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lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 9

lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 10

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lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 12

lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 13

lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 14

lots 7 & 8 (2.57 ac) Valley Road Oakland, MD MLS# MDGA2010424 - Image 15

1 of 15

$39,000

Studio

Beds

0.0

Baths

lots 7 & 8 (2.57 ac) Valley Road

Oakland, MD

Courtesy of THE KW COLLECTIVE

336 Paradise Heights Oakland, MD MLS# MDGA2010378 - Image 1

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Virtual Tour

1 of 94

$1,499,000

Beds

3.0

Baths

2,826

Sq.Ft.

336 Paradise Heights

Oakland, MD

Courtesy of RAILEY REALTY, INC.

Whispering Pines Lane Oakland, MD MLS# MDGA2010384 - Image 1

Whispering Pines Lane Oakland, MD MLS# MDGA2010384 - Image 2

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Whispering Pines Lane Oakland, MD MLS# MDGA2010384 - Image 19

Whispering Pines Lane Oakland, MD MLS# MDGA2010384 - Image 20

1 of 20

$60,000

Studio

Beds

0.0

Baths

Whispering Pines Lane

Oakland, MD

Courtesy of RAILEY REALTY, INC.

565 Glendale Road # 210A Oakland, MD MLS# MDGA2010362 - Image 1

565 Glendale Road # 210A Oakland, MD MLS# MDGA2010362 - Image 2

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565 Glendale Road # 210A Oakland, MD MLS# MDGA2010362 - Image 33

1 of 33

$175,000

Beds

1.0

Baths

382

Sq.Ft.

565 Glendale Road # 210A

Oakland, MD

Courtesy of RAILEY REALTY, INC.

About Oakland

Listings in Oakland, MD: 186
Estimated median home price: $320,000

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	37
$100K - 200K	23
$200K - 300K	29
$300K - 400K	13
$400K - 500K	13
$500K - 600K	14
$600K - 700K	9
$700K - 800K	8
$800K - 900K	5
$900K - 1M	5
$1M - Max	30

Homes for Sale by Type in Oakland, MD

Property Type	Count
Single Family	88
Townhouse	0
Condo	28
Commercial	10
Rental	1
Lots and Land	60
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 11/11/2025)

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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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