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Oakland, MD Real Estate and Properties for Sale

$1,200,000
Active
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826 G SWAUGER ROAD

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 3 Baths
  • 2,914 sqft
$299,000
Active
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2189 TABLE ROCK ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,736 sqft
$299,900
Active
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953 BRAY SCHOOL ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,008 sqft
$259,000
Active
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Lot B LOCH DEER ROAD

OAKLAND, MD 21550

  • Vacant Land
$84,369
Active
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QUENTIN LANE

OAKLAND, MD 21550

  • Vacant Land
$399,900
Active
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321 DEER PARK HOTEL ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,476 sqft
$615,000
Active
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308 WINDING TRAIL LANE #11B

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,300 sqft
$3,249,000
Active
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415 NAZELROD ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 6,036 sqft
$340,000
Active
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254 LITTLE MOUNTAIN ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,792 sqft
$739,000
Active
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12 ARROWHEAD LANE #12

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,650 sqft
$19,900
Active
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Lot 18 BUCK DRIVE

OAKLAND, MD 21550

  • Vacant Land
$42,000
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MAPLE DEL LANE

OAKLAND, MD 21550

  • Vacant Land
$599,000
Active
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428 SAM SNEAD CIRCLE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,542 sqft
$415,000
Active
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1499 FOSTER ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,234 sqft
$379,500
Active
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20160 GARRETT HIGHWAY #C307

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 636 sqft
$434,900
Active
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511 HILLTOP ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,406 sqft
$715,000
Active
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250 LEHMAN LANE #39

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,240 sqft
$19,000
Active
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6 CEDAR LANE

OAKLAND, MD 21550

  • Vacant Land
$250,000
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116 E OAK STREET

OAKLAND, MD 21550

  • Commercial
$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
$969,000
Active
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251 ROBINWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,284 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
$95,000
Active
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Lot 9 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Vacant Land
$95,000
Active
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Lot 10 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Vacant Land
$200,000
Active
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3.15 ACRES WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Vacant Land
$250,000
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5 ACRES LAKE SHORE 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
$49,900
Active
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RED RUN HEIGHTS ROAD

OAKLAND, MD 21550

  • Vacant Land
$1,689,000
Active
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670 WOODLANDS HILL LANE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,714 sqft
$79,500
Active
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8760 OAKLAND SANG RUN ROAD

OAKLAND, MD 21550

  • Vacant Land
$279,000
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277 CHEEKS LANE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,148 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
$250,000
Active
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6.89 ACRES WOODLANDS HILL DR DRIVE

OAKLAND, MD 21550

  • Vacant Land
$1,189,000
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248 TARN DRIVE

OAKLAND, MD 21550

  • Single Family
  • 6 Beds
  • 6 Baths
  • 3,482 sqft
$349,900
Active
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2448 BIRCHWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 3,352 sqft
$2,499,900
Active
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83 BETHLEHEM ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,190 sqft
$309,000
Active
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20160 GARRETT HIGHWAY #H706

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 550 sqft
$169,000
Active
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9.75 AC. DENNETT ROAD

OAKLAND, MD 21550

  • Vacant Land
$419,000
Active
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560 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 700 sqft
$325,000
Active
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17921 GARRETT HIGHWAY

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,563 sqft
$399,900
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565 GLENDALE ROAD #303B

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 887 sqft
$706,035
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0 GNEGY CHURCH ROAD

OAKLAND, MD 21550

  • Vacant Land
$1,025,000
Active
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127 PARADISE HEIGHTS

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,240 sqft
$375,000
Active
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321 N 3RD STREET

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 2 Baths
  • 3,660 sqft
$745,000
Active
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638 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,640 sqft
$795,000
Active
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312 MOSS CREEK CIRCLE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 4,230 sqft
$224,900
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206 MAYHEW INN ROAD

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
$34,900
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3482 OAKLAND SANG RUN ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,920 sqft
$585,000
Active
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55 VILLAGE DRIVE #5

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,280 sqft
$150,000
Active
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SANDERS LANE

OAKLAND, MD 21550

  • Vacant Land
$1,400,000
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827 PENN POINT ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,832 sqft
$699,000
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170 CHERRYWOOD DRIVE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,560 sqft
$49,000
Active
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Lot 24 EASTVIEW PLACE

OAKLAND, MD 21550

  • Vacant Land
$35,000
Active
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Lot 233 CUMBERLAND

OAKLAND, MD 21550

  • Vacant Land
$3,000
Active
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Lot 40 FAWN DRIVE

OAKLAND, MD 21550

  • Vacant Land
$49,900
Active
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LOT 6B BETTS LANE

OAKLAND, MD 21550

  • Vacant Land
$1,100,000
Active
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660 GLENDALE ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 3 Baths
  • 2,592 sqft
$249,900
Active
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565 GLENDALE ROAD #306

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 772 sqft
$160,000
Active
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132 &132A TARN DRIVE

OAKLAND, MD 21550

  • Vacant Land
$269,000
Active
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400 BEAR DRIVE E

OAKLAND, MD 21550

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

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,185 sqft
$579,000
Active
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312 3RD STREET

OAKLAND, MD 21550

  • Commercial
  • 10,735 sqft
$100,000
Active
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3500 Area MARYLAND HIGHWAY

OAKLAND, MD 21550

  • Vacant Land
$15,000
Active
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MARYLAND HIGHWAY

OAKLAND, MD 21550

  • Vacant Land
$18,000
Active
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13 BIRCHWOOD DRIVE

OAKLAND, MD 21550

  • Vacant Land
$18,000
Active
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22 ELM DRIVE

OAKLAND, MD 21550

  • Vacant Land
$16,000
Active
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21 BEAR DRIVE E

OAKLAND, MD 21550

  • Vacant Land
$18,000
Active
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27 GOBBLER RUN ROAD

OAKLAND, MD 21550

  • Vacant Land
$749,900
Active
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222 SKIPPERS POINT ROAD

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 2 Baths
  • 1,278 sqft
$294,999
Active
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135 JEFFREY LANE #19A

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 2,344 sqft
$349,000
Active
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552 BLACK OAK DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,152 sqft
$245,000
Active
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13 LAUREL BROOK DRIVE #13

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,320 sqft
$329,900
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565 GLENDALE ROAD #125

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 1 Bath
  • 496 sqft
$289,000
Active
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163 MITCHELL DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,242 sqft
$160,000
Active
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DENNETT RD, 10.10 ACRES TO OAKLAND DR

OAKLAND, MD 21550

  • Vacant Land
$275,900
Active
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449 S 3RD STREET

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,928 sqft
$950,000
Active
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164 GRANDVIEW DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,368 sqft
$219,000
Active
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141 MONTANA LANE

OAKLAND, MD 21550

  • Single Family
  • 1 Bed
  • 2 Baths
  • 912 sqft
$35,000
Active
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233 RHODODENDRON DRIVE

OAKLAND, MD 21550

  • Vacant Land
$399,999
Active
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654 N BRADLEY LANE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,464 sqft
$287,500
Active
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505 SOUTHERN PINES DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,248 sqft
$230,000
Active
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N 4TH STREET

OAKLAND, MD 21550

  • Commercial
$89,900
Active
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15.75 ACRES BETHLEHEM ROAD

OAKLAND, MD 21550

  • Vacant Land
$294,000
Active
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157 JEFFREY LANE #21B

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 550 sqft
$769,900
Active
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467 PARADISE RIDGE ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,780 sqft
$2,500,000
Active
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19530 GARRETT HIGHWAY

OAKLAND, MD 21550

  • Commercial
  • 7,818 sqft
$64,900
Active
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74 PARKS ROAD

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 792 sqft
$749,000
Active
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130 TIMBERLOFT CIRCLE #14

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,900 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
$629,000
Active
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231 SANTA FE TRAIL

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,280 sqft
$275,000
Active
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127 S OAKHALL DRIVE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,913 sqft
$439,000
Active
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401 DAVE TURNEY STREET

OAKLAND, MD 21550

  • Commercial
  • 5,328 sqft
$295,000
Active
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26 GREEN BRIER ROAD

OAKLAND, MD 21550

  • Commercial
$185,000
Active
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729 E OAK STREET

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,170 sqft
$899,900
Active
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267 SAN FRANCISCO STREET

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,278 sqft
$975,000
Active
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GLENDALE RD LOT 12 ALPINE VILLAGE SUBDIVISION

OAKLAND, MD 21550

  • Vacant Land
$329,999
Active
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931 BLACK OAK DRIVE

OAKLAND, MD 21550

  • Single Family
  • 3 Beds
  • 1 Bath
  • 990 sqft
$5,000
Active
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Lot 17 BIRCHWOOD DRIVE

OAKLAND, MD 21550

  • Vacant Land
$569,000
Active
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178 WINDING TRAIL LANE #5B

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,300 sqft
$275,000
Active
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5423 GORMAN ROAD

OAKLAND, MD 21550

  • Commercial
  • 720 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 6/30/2026 02:31 PM PST. Copyright 2026 BRIGHT MLS – All Rights Reserved.