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
$5,495,000
Active
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218 SMITH POINTE ROAD

SWANTON, MD 21561

  • Single Family
  • 6 Beds
  • 6 Baths
  • 6,225 sqft
$4,000,000
Active
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180 GLEN COVE ROAD

SWANTON, MD 21561

  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,009 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
$2,748,000
Active
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42 RED OAK WAY

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 7 Baths
  • 3,648 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
$1,939,900
Active
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282 LAKEFRONT LINKS DRIVE

SWANTON, MD 21561

  • Single Family
  • 6 Beds
  • 7 Baths
  • 6,697 sqft
$1,929,900
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200 STILLWATER DRIVE

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,788 sqft
$1,899,000
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389 SAWMILL HOLLOW ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,585 sqft
$1,889,000
Active
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2187 STATE PARK ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,248 sqft
$1,850,000
Active
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507 SHORELINE DRIVE

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,417 sqft
$1,750,000
Active
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499 OAKLAND DRIVE

OAKLAND, MD 21550

  • Commercial
  • 15,000 sqft
$1,740,000
Active
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619 WATERFRONT GREENS DRIVE

SWANTON, MD 21561

  • Single Family
  • 7 Beds
  • 6 Baths
  • 4,559 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
$1,649,000
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85 WINDY COVE ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,508 sqft
$1,625,000
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410 S SHORE ROAD

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,870 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
$1,549,000
Active
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425 HINES DRIVE

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,640 sqft
$1,500,000
Active
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342 LAKEFRONT LINKS DRIVE

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 6 Baths
  • 3,606 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
$1,399,900
Active
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340 S SHORE ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,227 sqft
$1,385,000
Active
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105 MONASTERY WAY

SWANTON, MD 21561

  • Single Family
  • 10 Beds
  • 10 Baths
  • 3,309 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
$1,325,000
Active
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85 CLUBHOUSE DRIVE

SWANTON, MD 21561

  • Single Family
  • 6 Beds
  • 6 Baths
  • 3,360 sqft
$1,200,000
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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
$1,189,000
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96 WHISPERING WAY

SWANTON, MD 21561

  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,344 sqft
$1,150,000
Active
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725 CANDLE TREE LANE

SWANTON, MD 21561

  • Single Family
  • 2 Beds
  • 1 Bath
  • 1,581 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
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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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3836 CHESTNUT GROVE ROAD

SWANTON, MD 21561

  • Single Family
  • 4 Beds
  • 3 Baths
  • 5,120 sqft
$975,000
Active
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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
$949,000
Active
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723 PINNACLE DRIVE

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,716 sqft
$945,000
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304 WATERFRONT GREENS DRIVE

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,926 sqft
$925,000
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949 HARVEYS PENINSULA ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,148 sqft
$914,999
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2828 GLENDALE ROAD

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 6 Baths
  • 4,110 sqft
$899,900
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267 SAN FRANCISCO STREET

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 3,278 sqft
$899,900
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113 JUBB MEADOWS LANE

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,185 sqft
$825,000
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495 WHITE OAK DRIVE

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,448 sqft
$800,000
Active
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14 COMMERCE DRIVE

OAKLAND, MD 21550

  • Commercial
  • 10,000 sqft
$799,000
Active
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302 OAK WAY ROAD

SWANTON, MD 21561

  • Single Family
  • 4 Beds
  • 4 Baths
  • 1,404 sqft
$795,000
Active
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312 MOSS CREEK CIRCLE

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 4 Baths
  • 4,230 sqft
$795,000
Active
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32 MONASTERY WAY

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 5 Baths
  • 2,700 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
Active
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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
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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
$695,000
Active
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398 SNOWBIRD LANE

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 4 Baths
  • 2,310 sqft
$679,900
Active
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4A MYSTIC CREEK TRAIL

OAKLAND, MD 21550

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

OAKLAND, MD 21550

  • Vacant Land
$669,000
Active
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32 HAZELHURST LANE

SWANTON, MD 21561

  • Single Family
  • 5 Beds
  • 3 Baths
  • 3,100 sqft
$639,900
Active
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1651 SWANTON ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 3,640 sqft
$629,000
Active
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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
$599,900
Active
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167 SEARS LANE

SWANTON, MD 21561

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,688 sqft
$599,000
Active
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428 SAM SNEAD CIRCLE

OAKLAND, MD 21550

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

OAKLAND, MD 21550

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

OAKLAND, MD 21550

  • Commercial
  • 10,735 sqft
$575,000
Active
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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
$524,900
Active
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365 RIDGE ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,080 sqft
$499,900
Active
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126 LEO FRIEND ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,235 sqft
$480,000
Active
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119 CEDAR HILL DRIVE

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,400 sqft
$475,000
Active
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333 SLOAN TRACT ROAD

OAKLAND, MD 21550

  • Single Family
  • 4 Beds
  • 4 Baths
  • 1,492 sqft
$459,000
Active
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807 GREEN GLADE RD.

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,449 sqft
$449,000
Active
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249 HAZELHURST ROAD

SWANTON, MD 21561

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,512 sqft
$439,000
Active
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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
Active
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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
Active
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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
Active
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20160 GARRETT HIGHWAY #G507

OAKLAND, MD 21550

  • Single Family
  • 2 Beds
  • 1 Bath
  • 912 sqft
$389,000
Active
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TURKEY NECK ROAD #LOT 12

SWANTON, MD 21561

  • Vacant Land
$385,000
Active
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2195 GLENDALE ROAD

SWANTON, MD 21561

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

OAKLAND, MD 21550

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

OAKLAND, MD 21550

  • Single Family
  • 5 Beds
  • 2 Baths
  • 3,660 sqft
$349,900
Active
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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

Nearby Cities to 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.