148 total properties
Did you mean the neighborhood Oakland?
View Hammond Street Oakland, MD MLS# MDGA2011044
  • Recently Listed
1 of 2
$29,900
Studio

Beds

0.0

Baths

Hammond Street

Oakland, MD

Bright
Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
View 729 E Oak Street Oakland, MD MLS# MDGA2011048
  • Recently Listed
1 of 62
$185,000
3

Beds

1.1

Baths

1,170

Sq.Ft.

729 E Oak Street

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 267 San Francisco Street Oakland, MD MLS# MDGA2011040
$899,900
4

Beds

2.1

Baths

3,278

Sq.Ft.

267 San Francisco Street

Oakland, MD

Bright
Courtesy of HOMESMART
The time to sell is now! THE TIME TO SELL IS NOW!
View Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
  • Recently Listed with Virtual Tour
1 of 10
$995,000
Studio

Beds

0.0

Baths

Glendale Rd Lot 12 Alpine Village Subdivision

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 3416 Broadford Road Oakland, MD MLS# MDGA2011020
  • Recently Listed
1 of 23
$85,000
3

Beds

1.0

Baths

1,462

Sq.Ft.

3416 Broadford Road

Oakland, MD

Bright
Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
View Lots 34 & 35 Fox Tail Road Oakland, MD MLS# MDGA2011026
$5,000
Studio

Beds

0.0

Baths

Lots 34 & 35 Fox Tail Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 43 Sloan Tract Road Oakland, MD MLS# MDGA2011032
  • Recently Listed
1 of 47
$324,900
4

Beds

2.0

Baths

1,743

Sq.Ft.

43 Sloan Tract Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 711 Heritage Drive Oakland, MD MLS# MDGA2011022
$249,000
3

Beds

2.0

Baths

1,400

Sq.Ft.

711 Heritage Drive

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 232 Jeffrey Lane # 33 Oakland, MD MLS# MDGA2011030
$425,000
2

Beds

2.1

Baths

1,301

Sq.Ft.

232 Jeffrey Lane # 33

Oakland, MD

Bright
Courtesy of SAMSON PROPERTIES
View 1108 Hutton Road Oakland, MD MLS# MDGA2010986
$199,000
2

Beds

1.0

Baths

960

Sq.Ft.

1108 Hutton Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 1359 Cedar Lane Oakland, MD MLS# MDGA2010974
  • Virtual Tour
1 of 37
$275,000
2

Beds

1.1

Baths

1,440

Sq.Ft.

1359 Cedar Lane

Oakland, MD

Bright
Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
View 3395 Fingerboard Road Oakland, MD MLS# MDGA2010996
  • Recently Listed
1 of 20
$199,000
4

Beds

2.0

Baths

3395 Fingerboard Road

Oakland, MD

Bright
Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
View Upperman Road Oakland, MD MLS# MDGA2010944
$325,000
Studio

Beds

0.0

Baths

Upperman Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 931 Black Oak Drive Oakland, MD MLS# MDGA2010958
  • Recently Listed
1 of 53
$359,000
3

Beds

1.0

Baths

990

Sq.Ft.

931 Black Oak Drive

Oakland, MD

Bright
Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
View 143 Manor Drive Oakland, MD MLS# MDGA2010990
$299,900
3

Beds

1.1

Baths

1,786

Sq.Ft.

143 Manor Drive

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 178 Winding Trail Lane # 5B Oakland, MD MLS# MDGA2010960
$589,000
5

Beds

4.1

Baths

3,300

Sq.Ft.

178 Winding Trail Lane # 5B

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View Lot 17 Birchwood Drive Oakland, MD MLS# MDGA2010950
$5,000
Studio

Beds

0.0

Baths

Lot 17 Birchwood Drive

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 1358 Crellin Underwood Road Oakland, MD MLS# MDGA2010946
$85,000
2

Beds

1.0

Baths

864

Sq.Ft.

1358 Crellin Underwood Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 14 Laurel Brook Drive # 14 Oakland, MD MLS# MDGA2010940
$269,900
2

Beds

2.0

Baths

1,320

Sq.Ft.

14 Laurel Brook Drive # 14

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 5423 Gorman Road Oakland, MD MLS# MDGA2010906
$275,000
720

Sq.Ft.

5423 Gorman Road

Oakland, MD

Bright
Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES

About Oakland

Listings in Oakland, MD

158

Estimated median home price

$284,950
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

PriceCount
$0 - 100K36
$100K - 200K24
$200K - 300K23
$300K - 400K14
$400K - 500K9
$500K - 600K10
$600K - 700K9
$700K - 800K6
$800K - 900K5
$900K - 1M4
$1M - Max18

Homes for Sale by Type in Oakland, MD

Property TypeCount
Single Family66
Townhouse1
Condo20
Commercial10
Rental4
Lots and Land61
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 1/28/2026)

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.

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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