Oakland, MD Real Estate and Properties for Sale | Berkshire Hathaway HomeServices Fox & Roach

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Oakland, MD Real Estate and Properties for Sale

$6,499,900
Active
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47 HOLY CROSS

OAKLAND, MD 21550

  • Single Family
  • 8 Beds
  • 9 Baths
  • 11,417 sqft
$6,000,000
Active
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4009 MAYHEW INN

OAKLAND, MD 21550

  • Commercial
  • 2,864 sqft
$3,249,000
Active
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415 NAZELROD ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 6,036 sqft
$2,799,900
Active
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65 ENTERPRISE DRIVE

OAKLAND, MD 21550

  • Commercial
  • 30,000 sqft
$2,500,000
Active
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19530 GARRETT HIGHWAY

OAKLAND, MD 21550

  • Commercial
  • 7,818 sqft
$2,499,900
Active
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83 BETHLEHEM ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,190 sqft
$2,350,000
Active
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2725 STOCKSLAGER ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 7 Baths
  • 5,376 sqft
$1,750,000
Active
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499 OAKLAND DRIVE

OAKLAND, MD 21550

  • Commercial
  • 15,000 sqft
$1,689,000
Active
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670 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,714 sqft
$1,650,000
Active
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3898 3898 UNDERWOOD RD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 6 Baths
  • 5,117 sqft
$1,579,900
Active
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2311 BOY SCOUT ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,278 sqft
$1,400,000
Active
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827 PENN POINT ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,832 sqft
$1,350,000
Active
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211 HIGH POINT RIDGE ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,472 sqft
$1,329,000
Active
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439 PARADISE HEIGHTS

OAKLAND, MD 21550

  • Single Family
  • 6 Beds
  • 5 Baths
  • 4,113 sqft
$1,200,000
Active
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122 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 2,656 sqft
$1,189,000
Active
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248 TARN DRIVE

OAKLAND, MD 21550

  • Single Family
  • 6 Beds
  • 6 Baths
  • 3,482 sqft
$1,100,000
Active
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660 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,592 sqft
$1,074,900
Active
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52 DAM VIEW DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 6 Baths
  • 3,032 sqft
$1,025,000
Active
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127 PARADISE HEIGHTS

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,240 sqft
$975,000
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GLENDALE RD LOT 12 ALPINE VILLAGE SUBDIVISION

OAKLAND, MD 21550

  • Vacant Land
$969,000
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251 ROBINWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,284 sqft
$950,000
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164 GRANDVIEW DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,368 sqft
$899,900
Active
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113 JUBB MEADOWS LANE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,185 sqft
$899,900
Active
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267 SAN FRANCISCO STREET

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,278 sqft
$800,000
Active
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14 COMMERCE DRIVE

OAKLAND, MD 21550

  • Commercial
  • 10,000 sqft
$795,000
Active
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312 MOSS CREEK CIRCLE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 4,230 sqft
$769,900
Active
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467 PARADISE RIDGE ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,780 sqft
$760,000
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1909 PYSELL CROSSCUT ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 2,970 sqft
$749,900
Active
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25 SILVER TREE LANE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,364 sqft
$749,900
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222 SKIPPERS POINT ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 2 Baths
  • 1,278 sqft
$749,000
Active
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130 TIMBERLOFT CIRCLE #14

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,900 sqft
$745,000
Active
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638 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,640 sqft
$715,000
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250 LEHMAN LANE #39

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,240 sqft
$706,035
Active
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0 GNEGY CHURCH ROAD

OAKLAND, MD 21550

  • Vacant Land
$699,000
Active
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170 CHERRYWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,560 sqft
$679,900
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4A MYSTIC CREEK TRAIL

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,000 sqft
$675,000
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GEORGE WASHINGTON HIGHWAY

OAKLAND, MD 21550

  • Vacant Land
$629,000
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231 SANTA FE TRAIL

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,280 sqft
$615,000
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308 WINDING TRAIL LANE #11B

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,300 sqft
$599,000
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428 SAM SNEAD CIRCLE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,542 sqft
$585,000
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55 VILLAGE DRIVE #5

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,280 sqft
$579,000
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312 3RD STREET

OAKLAND, MD 21550

  • Commercial
  • 10,735 sqft
$575,000
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20160 GARRETT HIGHWAY #F501-701

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,700 sqft
$569,000
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178 WINDING TRAIL LANE #5B

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,300 sqft
$545,000
Active
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328 STOOL ROCK ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,860 sqft
$499,900
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126 LEO FRIEND ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,235 sqft
$475,000
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333 SLOAN TRACT ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 1,492 sqft
$439,000
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401 DAVE TURNEY STREET

OAKLAND, MD 21550

  • Commercial
  • 5,328 sqft
$434,900
Active
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511 HILLTOP ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,406 sqft
$425,000
Active
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LOT 25 HOLY CROSS DRIVE

OAKLAND, MD 21550

  • Vacant Land
$425,000
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104 PINE TOP TRAIL

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 4 Baths
  • 1,596 sqft
$419,000
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560 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 700 sqft
$415,000
Active
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1499 FOSTER ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,234 sqft
$400,000
Active
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3257 GEORGE WASHINGTON HIGHWAY

OAKLAND, MD 21550

  • Vacant Land
$399,999
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654 N BRADLEY LANE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,464 sqft
$399,900
Active
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321 DEER PARK HOTEL ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,476 sqft
$399,900
Active
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565 GLENDALE ROAD #303B

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 887 sqft
$399,000
Active
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216 E ALDER STREET

OAKLAND, MD 21550

  • Commercial
  • 3,422 sqft
$399,000
Active
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5024 CRANESVILLE ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,128 sqft
$389,000
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20160 GARRETT HIGHWAY #G507

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 912 sqft
$379,500
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20160 GARRETT HIGHWAY #C307

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 636 sqft
$375,000
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321 N 3RD STREET

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 2 Baths
  • 3,660 sqft
$349,900
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2448 BIRCHWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 3,352 sqft
$349,000
Active
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552 BLACK OAK DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,152 sqft
$340,000
Active
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254 LITTLE MOUNTAIN ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,792 sqft
$339,900
Active
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531 GLENDALE ROAD #B302

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 887 sqft
$339,000
Active
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961 CEDAR LANE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,920 sqft
$329,999
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931 BLACK OAK DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 990 sqft
$329,900
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565 GLENDALE ROAD #125

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 496 sqft
$325,000
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17921 GARRETT HIGHWAY

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,563 sqft
$309,000
Active
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20160 GARRETT HIGHWAY #H706

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 550 sqft
$309,000
Active
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8946 OAKLAND SANG RUN ROAD

OAKLAND, MD 21550

  • Vacant Land
$304,000
Active
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565 GLENDALE ROAD #B206

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 780 sqft
$299,900
Active
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953 BRAY SCHOOL ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,008 sqft
$299,000
Active
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2189 TABLE ROCK ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,736 sqft
$295,000
Active
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26 GREEN BRIER ROAD

OAKLAND, MD 21550

  • Vacant Land
$289,000
Active
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163 MITCHELL DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,242 sqft
$287,500
Active
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505 SOUTHERN PINES DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,248 sqft
$285,500
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1737 KING WILDESEN ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,736 sqft
$279,900
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400 BEAR DRIVE E

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 2 Baths
  • 560 sqft
$279,000
Active
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277 CHEEKS LANE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,148 sqft
$275,900
Active
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449 S 3RD STREET

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,928 sqft
$275,000
Active
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127 S OAKHALL DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,913 sqft
$275,000
Active
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5423 GORMAN ROAD

OAKLAND, MD 21550

  • Commercial
  • 720 sqft
$269,500
Active
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315 COOLIDGE AVENUE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,600 sqft
$259,900
Active
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181 JEFFREY LANE #23A

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 670 sqft
$259,000
Active
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Lot B LOCH DEER ROAD

OAKLAND, MD 21550

  • Vacant Land
$250,000
Active
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6.89 ACRES WOODLANDS HILL DR DRIVE

OAKLAND, MD 21550

  • Vacant Land
$250,000
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5 ACRES LAKE SHORE DRIVE

OAKLAND, MD 21550

  • Vacant Land
$250,000
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116 E OAK STREET

OAKLAND, MD 21550

  • Commercial
$249,900
Active
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565 GLENDALE ROAD #306

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 772 sqft
$230,000
Active
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N 4TH STREET

OAKLAND, MD 21550

  • Commercial
$224,900
Active
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206 MAYHEW INN ROAD

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
$219,000
Active
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141 MONTANA LANE

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 2 Baths
  • 912 sqft
$214,900
Active
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565 GLENDALE ROAD #106 B

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
$200,000
Active
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3.15 ACRES WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Vacant Land
$199,900
Active
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0 LAKE SHORE DRIVE

OAKLAND, MD 21550

  • Vacant Land
$199,900
Active
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2 OVERLOOK RIDGE DRIVE

OAKLAND, MD 21550

  • Vacant Land
$195,000
Active
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2918 OAKLAND SANG RUN ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,382 sqft
$185,000
Active
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729 E OAK STREET

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,170 sqft

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 6/29/2026 05:17 PM PST. Copyright 2026 BRIGHT MLS – All Rights Reserved.