Lori Rubenstein

Please reload the page to update with the latest MLS information available.

Please reload the page to update with the latest MLS information available.

Please reload the page to update with the latest MLS information available.

Reload
 

Oakland, MD Real Estate and Properties for Sale

$299,000
Active
Data Source Icon

2189 TABLE ROCK ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,736 sqft
$299,900
Active
Data Source Icon

953 BRAY SCHOOL ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,008 sqft
$259,000
Active
Data Source Icon

Lot B LOCH DEER ROAD

OAKLAND, MD 21550

  • Vacant Land
$84,369
Active
Data Source Icon

QUENTIN LANE

OAKLAND, MD 21550

  • Vacant Land
$399,900
Active
Data Source Icon

321 DEER PARK HOTEL ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,476 sqft
$615,000
Active
Data Source Icon

308 WINDING TRAIL LANE #11B

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,300 sqft
$3,249,000
Active
Data Source Icon

415 NAZELROD ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 6,036 sqft
$340,000
Active
Data Source Icon

254 LITTLE MOUNTAIN ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,792 sqft
$739,000
Active
Data Source Icon

12 ARROWHEAD LANE #12

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,650 sqft
$19,900
Active
Data Source Icon

Lot 18 BUCK DRIVE

OAKLAND, MD 21550

  • Vacant Land
$42,000
Active
Data Source Icon

MAPLE DEL LANE

OAKLAND, MD 21550

  • Vacant Land
$599,000
Active
Data Source Icon

428 SAM SNEAD CIRCLE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,542 sqft
$415,000
Active
Data Source Icon

1499 FOSTER ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,234 sqft
$379,500
Active
Data Source Icon

20160 GARRETT HIGHWAY #C307

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 636 sqft
$434,900
Active
Data Source Icon

511 HILLTOP ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,406 sqft
$715,000
Active
Data Source Icon

250 LEHMAN LANE #39

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,240 sqft
$19,000
Active
Data Source Icon

6 CEDAR LANE

OAKLAND, MD 21550

  • Vacant Land
$250,000
Active
Data Source Icon

116 E OAK STREET

OAKLAND, MD 21550

  • Commercial
$1,350,000
Active
Data Source Icon

211 HIGH POINT RIDGE ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,472 sqft
$969,000
Active
Data Source Icon

251 ROBINWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,284 sqft
$1,579,900
Active
Data Source Icon

2311 BOY SCOUT ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,278 sqft
$95,000
Active
Data Source Icon

Lot 9 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Vacant Land
$95,000
Active
Data Source Icon

Lot 10 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Vacant Land
$200,000
Active
Data Source Icon

3.15 ACRES WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Vacant Land
$250,000
Active
Data Source Icon

5 ACRES LAKE SHORE DRIVE

OAKLAND, MD 21550

  • Vacant Land
$195,000
Active
Data Source Icon

2918 OAKLAND SANG RUN ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,382 sqft
$49,900
Active
Data Source Icon

RED RUN HEIGHTS ROAD

OAKLAND, MD 21550

  • Vacant Land
$1,689,000
Active
Data Source Icon

670 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,714 sqft
$79,500
Active
Data Source Icon

8760 OAKLAND SANG RUN ROAD

OAKLAND, MD 21550

  • Vacant Land
$279,000
Active
Data Source Icon

277 CHEEKS LANE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,148 sqft
$1,200,000
Active
Data Source Icon

122 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 2,656 sqft
$250,000
Active
Data Source Icon

6.89 ACRES WOODLANDS HILL DR DRIVE

OAKLAND, MD 21550

  • Vacant Land
$1,189,000
Active
Data Source Icon

248 TARN DRIVE

OAKLAND, MD 21550

  • Single Family
  • 6 Beds
  • 6 Baths
  • 3,482 sqft
$349,900
Active
Data Source Icon

2448 BIRCHWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 3,352 sqft
$2,499,900
Active
Data Source Icon

83 BETHLEHEM ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,190 sqft
$309,000
Active
Data Source Icon

20160 GARRETT HIGHWAY #H706

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 550 sqft
$169,000
Active
Data Source Icon

9.75 AC. DENNETT ROAD

OAKLAND, MD 21550

  • Vacant Land
$419,000
Active
Data Source Icon

560 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 700 sqft
$325,000
Active
Data Source Icon

17921 GARRETT HIGHWAY

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,563 sqft
$399,900
Active
Data Source Icon

565 GLENDALE ROAD #303B

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 887 sqft
$706,035
Active
Data Source Icon

0 GNEGY CHURCH ROAD

OAKLAND, MD 21550

  • Vacant Land
$1,025,000
Active
Data Source Icon

127 PARADISE HEIGHTS

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,240 sqft
$375,000
Active
Data Source Icon

321 N 3RD STREET

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 2 Baths
  • 3,660 sqft
$745,000
Active
Data Source Icon

638 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,640 sqft
$795,000
Active
Data Source Icon

312 MOSS CREEK CIRCLE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 4,230 sqft
$224,900
Active
Data Source Icon

206 MAYHEW INN ROAD

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
$34,900
Active
Data Source Icon

3482 OAKLAND SANG RUN ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,920 sqft
$585,000
Active
Data Source Icon

55 VILLAGE DRIVE #5

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,280 sqft
$150,000
Active
Data Source Icon

SANDERS LANE

OAKLAND, MD 21550

  • Vacant Land
$1,400,000
Active
Data Source Icon

827 PENN POINT ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,832 sqft
$699,000
Active
Data Source Icon

170 CHERRYWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,560 sqft
$49,000
Active
Data Source Icon

Lot 24 EASTVIEW PLACE

OAKLAND, MD 21550

  • Vacant Land
$35,000
Active
Data Source Icon

Lot 233 CUMBERLAND

OAKLAND, MD 21550

  • Vacant Land
$3,000
Active
Data Source Icon

Lot 40 FAWN DRIVE

OAKLAND, MD 21550

  • Vacant Land
$49,900
Active
Data Source Icon

LOT 6B BETTS LANE

OAKLAND, MD 21550

  • Vacant Land
$1,100,000
Active
Data Source Icon

660 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,592 sqft
$249,900
Active
Data Source Icon

565 GLENDALE ROAD #306

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 772 sqft
$160,000
Active
Data Source Icon

132 &132A TARN DRIVE

OAKLAND, MD 21550

  • Vacant Land
$279,900
Active
Data Source Icon

400 BEAR DRIVE E

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 2 Baths
  • 560 sqft
$899,900
Active
Data Source Icon

113 JUBB MEADOWS LANE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,185 sqft
$579,000
Active
Data Source Icon

312 3RD STREET

OAKLAND, MD 21550

  • Commercial
  • 10,735 sqft
$100,000
Active
Data Source Icon

3500 Area MARYLAND HIGHWAY

OAKLAND, MD 21550

  • Vacant Land
$15,000
Active
Data Source Icon

MARYLAND HIGHWAY

OAKLAND, MD 21550

  • Vacant Land
$18,000
Active
Data Source Icon

13 BIRCHWOOD DRIVE

OAKLAND, MD 21550

  • Vacant Land
$18,000
Active
Data Source Icon

22 ELM DRIVE

OAKLAND, MD 21550

  • Vacant Land
$16,000
Active
Data Source Icon

21 BEAR DRIVE E

OAKLAND, MD 21550

  • Vacant Land
$18,000
Active
Data Source Icon

27 GOBBLER RUN ROAD

OAKLAND, MD 21550

  • Vacant Land
$749,900
Active
Data Source Icon

222 SKIPPERS POINT ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 2 Baths
  • 1,278 sqft
$294,999
Active
Data Source Icon

135 JEFFREY LANE #19A

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 2,344 sqft
$349,000
Active
Data Source Icon

552 BLACK OAK DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,152 sqft
$245,000
Active
Data Source Icon

13 LAUREL BROOK DRIVE #13

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,320 sqft
$329,900
Active
Data Source Icon

565 GLENDALE ROAD #125

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 496 sqft
$289,000
Active
Data Source Icon

163 MITCHELL DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,242 sqft
$160,000
Active
Data Source Icon

DENNETT RD, 10.10 ACRES TO OAKLAND DR

OAKLAND, MD 21550

  • Vacant Land
$275,900
Active
Data Source Icon

449 S 3RD STREET

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,928 sqft
$950,000
Active
Data Source Icon

164 GRANDVIEW DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,368 sqft
$219,000
Active
Data Source Icon

141 MONTANA LANE

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 2 Baths
  • 912 sqft
$35,000
Active
Data Source Icon

233 RHODODENDRON DRIVE

OAKLAND, MD 21550

  • Vacant Land
$399,999
Active
Data Source Icon

654 N BRADLEY LANE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,464 sqft
$287,500
Active
Data Source Icon

505 SOUTHERN PINES DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,248 sqft
$230,000
Active
Data Source Icon

N 4TH STREET

OAKLAND, MD 21550

  • Commercial
$89,900
Active
Data Source Icon

15.75 ACRES BETHLEHEM ROAD

OAKLAND, MD 21550

  • Vacant Land
$294,000
Active
Data Source Icon

157 JEFFREY LANE #21B

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 550 sqft
$769,900
Active
Data Source Icon

467 PARADISE RIDGE ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,780 sqft
$2,500,000
Active
Data Source Icon

19530 GARRETT HIGHWAY

OAKLAND, MD 21550

  • Commercial
  • 7,818 sqft
$64,900
Active
Data Source Icon

74 PARKS ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 792 sqft
$749,000
Active
Data Source Icon

130 TIMBERLOFT CIRCLE #14

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,900 sqft
$1,074,900
Active
Data Source Icon

52 DAM VIEW DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 6 Baths
  • 3,032 sqft
$629,000
Active
Data Source Icon

231 SANTA FE TRAIL

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,280 sqft
$275,000
Active
Data Source Icon

127 S OAKHALL DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,913 sqft
$439,000
Active
Data Source Icon

401 DAVE TURNEY STREET

OAKLAND, MD 21550

  • Commercial
  • 5,328 sqft
$295,000
Active
Data Source Icon

26 GREEN BRIER ROAD

OAKLAND, MD 21550

  • Commercial
$185,000
Active
Data Source Icon

729 E OAK STREET

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,170 sqft
$899,900
Active
Data Source Icon

267 SAN FRANCISCO STREET

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,278 sqft
$975,000
Active
Data Source Icon

GLENDALE RD LOT 12 ALPINE VILLAGE SUBDIVISION

OAKLAND, MD 21550

  • Vacant Land
$329,999
Active
Data Source Icon

931 BLACK OAK DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 990 sqft
$5,000
Active
Data Source Icon

Lot 17 BIRCHWOOD DRIVE

OAKLAND, MD 21550

  • Vacant Land
$569,000
Active
Data Source Icon

178 WINDING TRAIL LANE #5B

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,300 sqft
$275,000
Active
Data Source Icon

5423 GORMAN ROAD

OAKLAND, MD 21550

  • Commercial
  • 720 sqft
$124,000
Active
Data Source Icon

Lot 20 PARADISE RIDGE ROAD

OAKLAND, MD 21550

  • Vacant Land

Nearby Cities to Oakland

Postal Codes Near Oakland

The data relating to real estate for sale on this web site comes in part from the IDX program of BRIGHT MLS. Information is supplied by seller and other third parties and has not been verified. All information provided is deemed reliable but is not guaranteed. All properties are subject to prior sale or withdrawal. Data may not be reproduced or redistributed and may not be used for any purpose other than consumers’ personal, non-commercial use. MLS Data Last Updated 6/30/2026 12:30 AM PST. Copyright 2026 BRIGHT MLS – All Rights Reserved.