205 total properties
Did you mean the neighborhood Oakland?
View Bear Drive E Oakland, MD MLS# MDGA2012426
  • Recently Listed
Save Bear Drive E Oakland, MD MLS# MDGA2012426
1 of 5
$19,900
Studio

Beds

0.0

Baths

Bear Drive E

Oakland, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 325 Markwood Drive Oakland, MD MLS# MDGA2012328
  • Recently Listed
Save 325 Markwood Drive Oakland, MD MLS# MDGA2012328
1 of 65
$799,000
4

Beds

3.1

Baths

3,376

Sq.Ft.

325 Markwood Drive

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View 187 Lower Penn Point Drive Oakland, MD MLS# MDGA2012396
  • Recently Listed
Save 187 Lower Penn Point Drive Oakland, MD MLS# MDGA2012396
1 of 44
$1,450,000
3

Beds

2.0

Baths

1,695

Sq.Ft.

187 Lower Penn Point Drive

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 995 Betts Lane Oakland, MD MLS# MDGA2012114
  • Recently Listed
Save 995 Betts Lane Oakland, MD MLS# MDGA2012114
1 of 45
$549,900
4

Beds

2.1

Baths

2,548

Sq.Ft.

995 Betts Lane

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View 255 Thornberry Road Oakland, MD MLS# MDGA2012400
  • Recently Listed with Virtual Tour
Save 255 Thornberry Road Oakland, MD MLS# MDGA2012400
1 of 122
$2,925,000
4

Beds

3.1

Baths

3,883

Sq.Ft.

255 Thornberry Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 5 Laurel Brook Drive # 5 Oakland, MD MLS# MDGA2012388
  • Recently Listed
Save 5 Laurel Brook Drive # 5 Oakland, MD MLS# MDGA2012388
1 of 29
$269,900
2

Beds

2.0

Baths

1,400

Sq.Ft.

5 Laurel Brook Drive # 5

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View 251 Robinwood Drive Oakland, MD MLS# MDGA2012378
  • Recently Listed
Save 251 Robinwood Drive Oakland, MD MLS# MDGA2012378
1 of 62
$775,000
5

Beds

4.1

Baths

4,284

Sq.Ft.

251 Robinwood Drive

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
  • Recently Listed
Save Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
1 of 6
$175,000
Studio

Beds

0.0

Baths

Robinwood Drive # 9

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View 37 Skippers Point Road Oakland, MD MLS# MDGA2012292
  • Recently Listed
Save 37 Skippers Point Road Oakland, MD MLS# MDGA2012292
1 of 49
$875,000
4

Beds

3.0

Baths

2,280

Sq.Ft.

37 Skippers Point Road

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View 610 Harvey Winters Drive Oakland, MD MLS# MDGA2012326
  • Recently Listed
Save 610 Harvey Winters Drive Oakland, MD MLS# MDGA2012326
1 of 38
$325,000
3

Beds

2.0

Baths

1,539

Sq.Ft.

610 Harvey Winters Drive

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
  • Recently Listed
Save 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
1 of 15
$149,000
Studio

Beds

0.0

Baths

16 Woodlands Hill Court

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
  • Recently Listed
Save 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
1 of 22
$159,000
Studio

Beds

0.0

Baths

22 Woodlands Hill Lane

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View Robinwood Drive # 13 Oakland, MD MLS# MDGA2012320
  • Recently Listed
Save Robinwood Drive # 13 Oakland, MD MLS# MDGA2012320
1 of 21
$99,000
Studio

Beds

0.0

Baths

Robinwood Drive # 13

Oakland, MD

Bright
Courtesy of TAYLOR-MADE DEEP CREEK SALES
View Bethlehem Rd Oakland, MD MLS# MDGA2012316
  • Recently Listed
Save Bethlehem Rd Oakland, MD MLS# MDGA2012316
1 of 7
$119,000
Studio

Beds

0.0

Baths

Bethlehem Rd

Oakland, MD

Bright
Courtesy of CUSTER REALTY & AUCTION
View 112 E Pennington Street Oakland, MD MLS# MDGA2012308
  • Recently Listed
Save 112 E Pennington Street Oakland, MD MLS# MDGA2012308
1 of 63
$350,000
5

Beds

3.0

Baths

2,165

Sq.Ft.

112 E Pennington Street

Oakland, MD

Bright
Courtesy of LAKE HOMES REALTY, LLC
View Cranesville Road Oakland, MD MLS# MDGA2012284
  • Recently Listed
Save Cranesville Road Oakland, MD MLS# MDGA2012284
1 of 17
$115,000
Studio

Beds

0.0

Baths

Cranesville Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
  • Recently Listed
Save 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
1 of 21
$599,000
Studio

Beds

0.0

Baths

97 acres Lot C Garrett Road

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 104 Roman Ridge Road # 21 Oakland, MD MLS# MDGA2012268
  • Recently Listed
Save 104 Roman Ridge Road # 21 Oakland, MD MLS# MDGA2012268
1 of 61
$605,000
5

Beds

4.1

Baths

2,582

Sq.Ft.

104 Roman Ridge Road # 21

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 17240 Garrett Highway Oakland, MD MLS# MDGA2012252
  • Recently Listed
Save 17240 Garrett Highway Oakland, MD MLS# MDGA2012252
1 of 104
$998,000
6

Beds

4.1

Baths

5,547

Sq.Ft.

17240 Garrett Highway

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.
View 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
  • Recently Listed with Virtual Tour
Save 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
1 of 65
$464,900
3

Beds

3.1

Baths

1,838

Sq.Ft.

256 Jeffrey Lane # 28

Oakland, MD

Bright
Courtesy of RAILEY REALTY, INC.

About Oakland

Listings in Oakland, MD

203

Estimated median home price

$304,000
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

PriceCount
$0 - 100K44
$100K - 200K23
$200K - 300K34
$300K - 400K27
$400K - 500K8
$500K - 600K10
$600K - 700K9
$700K - 800K16
$800K - 900K4
$900K - 1M5
$1M - Max23

Homes for Sale by Type in Oakland, MD

Property TypeCount
Single Family91
Townhouse1
Condo26
Commercial12
Rental6
Lots and Land73
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/22/2026)

Find Properties in Oakland, MD

Oakland, MD Information

Find Properties by Zip

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.

© 2026 BrightMLS. All Rights Reserved.