Oakland, MD Homes & Real Estate for Sale

Page 4 of 11
211 listings
237 GLENDALE RD, Oakland, MD 21550
Single-Family Home For Sale

$2,159,000

  • 7 bed |
  • 7 bath |
  • 3,735 sqft |
  • 0.57 acre lot
237 GLENDALE RD Oakland, MD 21550

#MDGA2009792 - Railey Realty, Inc.

333 SLOAN TRACT RD, Oakland, MD 21550
Single-Family Home For Sale

$475,000

  • 4 bed |
  • 4 bath |
  • 1,492 sqft |
  • 0.41 acre lot
333 SLOAN TRACT RD Oakland, MD 21550

#MDGA2009836 - Taylor Made Deep Creek Vacations & Sales

8760 OAKLAND SANG RUN RD, Oakland, MD 21550
Land For Sale

$82,500

  • 2.53 acre lot
8760 OAKLAND SANG RUN RD Oakland, MD 21550

#MDGA2009830 - Railey Realty, Inc.

0 COOLIDGE AVENUE, Oakland, MD 21550
Land For Sale

$85,000

  • 0.46 acre lot
0 COOLIDGE AVENUE Oakland, MD 21550

#MDGA2009824 - Taylor Made Deep Creek Vacations & Sales

609 SOUTHERN PINES DR, Oakland, MD 21550
Single-Family Home For Sale

$450,000

  • 4 bed |
  • 3 bath |
  • 2,030 sqft |
  • 3.91 acre lot
609 SOUTHERN PINES DR Oakland, MD 21550

#MDGA2009816 - BHHS Touchdown Home Pros Realty

285 WINDING TRAIL LN #10A, Oakland, MD 21550
Single-Family Home For Sale

$575,000

  • 5 bed |
  • 5 bath |
  • 3,300 sqft
285 WINDING TRAIL LN #10A Oakland, MD 21550

#MDGA2009744 - Railey Realty, Inc.

Lot 15 LITTLE MOUNTAIN ROAD, Oakland, MD 21550
Land For Sale

$35,000

  • 2.71 acre lot
Lot 15 LITTLE MOUNTAIN ROAD Oakland, MD 21550

#MDGA2009802 - BHHS Touchdown Home Pros Realty

62 MIDDLETON RD, Oakland, MD 21550
Single-Family Home For Sale

$829,900

  • 3 bed |
  • 3 bath |
  • 2,397 sqft |
  • 1.09 acre lot
62 MIDDLETON RD Oakland, MD 21550

#MDGA2009756 - Railey Realty, Inc.

FOX TAIL ROAD, Oakland, MD 21550
Land For Sale

$43,000

  • 1.58 acre lot
FOX TAIL ROAD Oakland, MD 21550

#MDGA2009788 - Railey Realty, Inc.

GEORGE WASHINGTON HWY, Oakland, MD 21550
Land For Sale

$934,000

  • 212.15 acre lot
GEORGE WASHINGTON HWY Oakland, MD 21550

#MDGA2009730 - Keller Williams Realty Centre

590 S BLAKESLEE RD, Oakland, MD 21550
Single-Family Home For Sale

$1,249,000

  • 4 bed |
  • 4 bath |
  • 3,071 sqft |
  • 1.68 acre lot
590 S BLAKESLEE RD Oakland, MD 21550

#MDGA2009738 - Taylor Made Deep Creek Vacations & Sales

501 CHRISTOPHERS WAY, Oakland, MD 21550
Single-Family Home For Sale

$249,000

  • 3 bed |
  • 2 bath |
  • 1,617 sqft |
  • 3 acre lot
501 CHRISTOPHERS WAY Oakland, MD 21550

#MDGA2009724 - Taylor Made Deep Creek Vacations & Sales

413 D ST, Mountain Lake Park, MD 21550
Single-Family Home For Sale

$239,000

  • 4 bed |
  • 2 bath |
  • 1,760 sqft |
  • 10,454 sqft lot
413 D ST Mountain Lake Park, MD 21550

#MDGA2009720 - Taylor Made Deep Creek Vacations & Sales

4 LAUREL BROOK DRIVE # 4, Oakland, MD 21550
Town Home For Sale

$235,000

  • 2 bed |
  • 2 bath
4 LAUREL BROOK DRIVE # 4 Oakland, MD 21550

#MDGA2009716 - Taylor Made Deep Creek Vacations & Sales

52 DAM VIEW DR, Oakland, MD 21550
Single-Family Home For Sale

$1,147,000

  • 4 bed |
  • 6 bath |
  • 3,032 sqft |
  • 1 acre lot
52 DAM VIEW DR Oakland, MD 21550

#MDGA2009714 - Taylor Made Deep Creek Vacations & Sales

2571 SHADY DELL RD, Oakland, MD 21550
Pending

$248,900

  • 2 bed |
  • 2 bath |
  • 1,678 sqft |
  • 2.02 acre lot
2571 SHADY DELL RD Oakland, MD 21550

#MDGA2009710 - Garrett Land Sales, PC

45 VILLAGE DR #4, Oakland, MD 21550
Single-Family Home For Sale

$450,000

  • 2 bed |
  • 2 bath |
  • 1,096 sqft
45 VILLAGE DR #4 Oakland, MD 21550

#MDGA2009698 - RE/MAX Realty Group

81 TIMBER LANE, Oakland, MD 21550
Pending

$125,000

  • 4 bed |
  • 2 bath |
  • 1,860 sqft |
  • 0.75 acre lot
81 TIMBER LANE Oakland, MD 21550

#MDGA2009696 - Lake Homes Realty, LLC

132 &132A TARN DRIVE, Oakland, MD 21550
Land For Sale

$175,000

  • 3.04 acre lot
132 &132A TARN DRIVE Oakland, MD 21550

#MDGA2009670 - Railey Realty, Inc.

MAYHEW INN ROAD, Oakland, MD 21550
Land For Sale

$165,000

  • 12.95 acre lot
MAYHEW INN ROAD Oakland, MD 21550

#MDGA2009662 - Railey Realty, Inc.

Presented by James Mark Wilson - Veterans United Realty

Veterans United Homefront
IDX Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement.

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. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose.

BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors. ©2025 BrightMLS. All rights reserved. Data displayed may be a portion of, and not a complete set of all listings published in the MLS.

For questions call 1-833-252-8030

Copyright © 2025 Veterans United Realty and Did You Serve, LLC. Homefront.com is NOT affiliated with any government agencies, including the VA. Homefront.com is a service of Did You Serve, LLC. Veterans United and the Veterans United House logo are registered trademarks of Mortgage Research Center, LLC, used under license agreement. Terms of Use.