10,771

Oakland, MD Homes

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  • 0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    /22

    $25,000

    Sold Jun 27, 2025

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

    • Land
    • 1.05 Acres
    • $23,810 per Acre

    Last Sold Summary

    • 84 Days On Market

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    • 1612 Mountainview Dr, Oakland, MD 21550
      1612 Mountainview Dr, Oakland, MD 21550
      1612 Mountainview Dr, Oakland, MD 21550
      /100

      Est $819,495

      Not Listed For Sale

      1612 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,607 Sq Ft
      • Built 1993
      1612 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 198 Days On Market

  • 207 Shenandoah Ave, Oakland, MD 21550
    207 Shenandoah Ave, Oakland, MD 21550
    /2

    $205,000

    Sold May 20, 2026

    207 Shenandoah Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Above List Price
    • $137/SF
    • 6 Days On Market

    Current Estimated Value $193,540

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    207 Shenandoah Ave, Oakland, MD 21550
    • 1194 Lake Shore Dr, Oakland, MD 21550
      1194 Lake Shore Dr, Oakland, MD 21550
      1194 Lake Shore Dr, Oakland, MD 21550
      /51

      Est $659,723

      Not Listed For Sale

      1194 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft
      • Built 1997
      1194 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 46 Days On Market

  • 245 Santa fe Trail, Oakland, MD 21550
    245 Santa fe Trail, Oakland, MD 21550
    245 Santa fe Trail, Oakland, MD 21550
    /40

    $615,000

    Sold Jul 07, 2025

    245 Santa fe Trail, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft
    • Built 2003

    Last Sold Summary

    • $270/SF
    • 51 Days On Market

    Current Estimated Value $598,839

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    245 Santa fe Trail, Oakland, MD 21550
    • 219 Mountainview Dr, Oakland, MD 21550
      219 Mountainview Dr, Oakland, MD 21550
      219 Mountainview Dr, Oakland, MD 21550
      /95

      Est $812,391

      Not Listed For Sale

      219 Mountainview Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 3,041 Sq Ft
      • Built 1990
      219 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • 2045 Swallow Falls Rd, Oakland, MD 21550
    2045 Swallow Falls Rd, Oakland, MD 21550
    2045 Swallow Falls Rd, Oakland, MD 21550
    /79

    $910,000

    Sold Sep 25, 2025

    2045 Swallow Falls Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 5,416 Sq Ft
    • Built 2023

    Last Sold Summary

    • $168/SF
    • 82 Days On Market

    Current Estimated Value $909,300

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    2045 Swallow Falls Rd, Oakland, MD 21550
    • 221 Randall Way, Oakland, MD 21550
      221 Randall Way, Oakland, MD 21550
      221 Randall Way, Oakland, MD 21550
      /106

      Est $1,685,231

      Not Listed For Sale

      221 Randall Way, Oakland, MD 21550

      • 5 Beds
      • 6 Baths
      • 5,155 Sq Ft
      • Built 1997
      221 Randall Way, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • 307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    /43

    $587,500

    Sold Aug 22, 2025

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2019

    Last Sold Summary

    • $178/SF
    • 9 Days On Market

    Current Estimated Value $568,890

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    • 939 Glendale Rd Unit 16, Oakland, MD 21550
      939 Glendale Rd Unit 16, Oakland, MD 21550
      939 Glendale Rd Unit 16, Oakland, MD 21550
      /33

      Est $579,242

      Not Listed For Sale

      939 Glendale Rd Unit 16, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • Built 1993
      939 Glendale Rd Unit 16, Oakland, MD 21550

      Last Sold Summary

      • 12 Days On Market

  • 336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    /94

    $1,340,000

    Sold Apr 08, 2026

    336 Paradise Heights, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • $474/SF
    • 159 Days On Market

    Current Estimated Value $1,370,882

    Last Listing Agent Susan Bell Railey Realty, Inc.

    336 Paradise Heights, Oakland, MD 21550
    • 262 Penn Cove Rd, Oakland, MD 21550
      262 Penn Cove Rd, Oakland, MD 21550
      262 Penn Cove Rd, Oakland, MD 21550
      /106

      Est $989,459

      Not Listed For Sale

      262 Penn Cove Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,700 Sq Ft
      • Built 1989
      262 Penn Cove Rd, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • 4000 Area Broadford Rd, Oakland, MD 21550
    4000 Area Broadford Rd, Oakland, MD 21550
    4000 Area Broadford Rd, Oakland, MD 21550
    /10

    $300,000

    Sold May 06, 2026

    4000 Area Broadford Rd, Oakland, MD 21550

    • Land
    • 56.5 Acres
    • $5,310 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    4000 Area Broadford Rd, Oakland, MD 21550
    • 324 Penn Cove Rd, Oakland, MD 21550
      324 Penn Cove Rd, Oakland, MD 21550
      324 Penn Cove Rd, Oakland, MD 21550
      /88

      Est $1,145,886

      Not Listed For Sale

      324 Penn Cove Rd, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 3,820 Sq Ft
      • Built 2004
      324 Penn Cove Rd, Oakland, MD 21550

      Last Sold Summary

      • 7 Days On Market

  • 3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, Oakland, MD 21550
    /43

    $290,000

    Sold Jun 01, 2026

    3749 Maryland Hwy, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,015 Sq Ft
    • Built 1982

    Last Sold Summary

    • 11% Below List Price
    • $144/SF
    • 63 Days On Market

    Current Estimated Value $296,959

    Last Listing Agent Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, Oakland, MD 21550
    • 545 Cumberland Rd, Oakland, MD 21550
      545 Cumberland Rd, Oakland, MD 21550
      545 Cumberland Rd, Oakland, MD 21550
      /100

      Est $503,478

      Not Listed For Sale

      545 Cumberland Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 2005
      545 Cumberland Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • 34 Hooppole Ct, Oakland, MD 21550
    34 Hooppole Ct, Oakland, MD 21550
    34 Hooppole Ct, Oakland, MD 21550
    /36

    $829,000

    Sold May 22, 2026

    34 Hooppole Ct, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • Built 1975

    Last Sold Summary

    • $612/SF
    • 0 Days On Market

    Current Estimated Value $817,945

    Last Listing Agent Rich Orr Railey Realty, Inc.

    34 Hooppole Ct, Oakland, MD 21550
    • 3598 Lake Shore Dr, Oakland, MD 21550
      3598 Lake Shore Dr, Oakland, MD 21550
      3598 Lake Shore Dr, Oakland, MD 21550
      /48

      Est $382,288

      Not Listed For Sale

      3598 Lake Shore Dr, Oakland, MD 21550

      • 1 Bed
      • 1.5 Baths
      • 665 Sq Ft
      • Built 1948
      3598 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 64 Days On Market

  • 0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    /4

    $12,000

    Sold Sep 25, 2025

    0 E Reese St, Oakland, MD 21550

    • Land
    • 10,890 Sq Ft
    • $48,000 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Thomas Long Railey Realty, Inc.

    0 E Reese St, Oakland, MD 21550
    • 3003 Lake Shore Dr, Oakland, MD 21550
      3003 Lake Shore Dr, Oakland, MD 21550
      3003 Lake Shore Dr, Oakland, MD 21550
      /87

      Est $1,168,111

      Not Listed For Sale

      3003 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 4.5 Baths
      • 1,968 Sq Ft
      • Built 1940
      3003 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 104 Days On Market

  • 445 Dennett Rd, Oakland, MD 21550
    445 Dennett Rd, Oakland, MD 21550
    445 Dennett Rd, Oakland, MD 21550
    /62

    $305,000

    Sold Nov 07, 2025

    445 Dennett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,410 Sq Ft
    • Built 1955

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Current Estimated Value $296,852

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    445 Dennett Rd, Oakland, MD 21550
    • 2303 Lake Shore Dr, Oakland, MD 21550
      2303 Lake Shore Dr, Oakland, MD 21550
      2303 Lake Shore Dr, Oakland, MD 21550
      /92

      Est $2,614,635

      Not Listed For Sale

      2303 Lake Shore Dr, Oakland, MD 21550

      • 6 Beds
      • 4.5 Baths
      • 5,859 Sq Ft
      • Built 2001
      2303 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 84 Days On Market

  • 2332 Paradise Point Rd, Oakland, MD 21550
    2332 Paradise Point Rd, Oakland, MD 21550
    2332 Paradise Point Rd, Oakland, MD 21550
    /74

    $1,425,000

    Sold May 20, 2026

    2332 Paradise Point Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $690/SF
    • 2 Days On Market

    Current Estimated Value $1,355,047

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    2332 Paradise Point Rd, Oakland, MD 21550
    • 568 Skippers Point Rd, Oakland, MD 21550
      568 Skippers Point Rd, Oakland, MD 21550
      568 Skippers Point Rd, Oakland, MD 21550
      /60

      Est $532,692

      Not Listed For Sale

      568 Skippers Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1981
      568 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • 648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    /61

    $275,000

    Sold Sep 05, 2025

    648 S 3rd St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1940

    Last Sold Summary

    • $185/SF
    • 3 Days On Market

    Current Estimated Value $282,333

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
    • 228 Paradise Heights, Oakland, MD 21550
      228 Paradise Heights, Oakland, MD 21550
      228 Paradise Heights, Oakland, MD 21550
      /82

      Est $1,830,637

      Not Listed For Sale

      228 Paradise Heights, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,249 Sq Ft
      • Built 1989
      228 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • 175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    /53

    $509,000

    Sold May 05, 2026

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $159/SF
    • 72 Days On Market

    Current Estimated Value $526,797

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    • 26 Paradise Ridge Rd, Oakland, MD 21550
      26 Paradise Ridge Rd, Oakland, MD 21550
      26 Paradise Ridge Rd, Oakland, MD 21550
      /63

      Est $524,929

      Not Listed For Sale

      26 Paradise Ridge Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,104 Sq Ft
      • Built 1975
      26 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 178 Days On Market

  • 1220 Broadford Rd, Oakland, MD 21550
    1220 Broadford Rd, Oakland, MD 21550
    1220 Broadford Rd, Oakland, MD 21550
    /52

    $365,000

    Sold Aug 12, 2025

    1220 Broadford Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft
    • Built 1971

    Last Sold Summary

    • $174/SF
    • 58 Days On Market

    Current Estimated Value $363,026

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1220 Broadford Rd, Oakland, MD 21550
    • 187 Lower Penn Point Dr, Oakland, MD 21550
      187 Lower Penn Point Dr, Oakland, MD 21550
      187 Lower Penn Point Dr, Oakland, MD 21550
      /30

      Est $1,127,938

      Not Listed For Sale

      187 Lower Penn Point Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • Built 1950
      187 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 80 Days On Market

  • 65 Village Dr Unit 6, Oakland, MD 21550
    65 Village Dr Unit 6, Oakland, MD 21550
    65 Village Dr Unit 6, Oakland, MD 21550
    /52

    $585,000

    Sold Mar 31, 2026

    65 Village Dr Unit 6, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,740 Sq Ft
    • Built 2006

    Last Sold Summary

    • $336/SF
    • 390 Days On Market

    Current Estimated Value $579,619

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    65 Village Dr Unit 6, Oakland, MD 21550
    • 156 Sunrise Point Ln, Oakland, MD 21550
      156 Sunrise Point Ln, Oakland, MD 21550
      156 Sunrise Point Ln, Oakland, MD 21550
      /35

      Est $1,470,198

      Not Listed For Sale

      156 Sunrise Point Ln, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1950
      156 Sunrise Point Ln, Oakland, MD 21550

      Last Sold Summary

      • 38 Days On Market

  • 425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    /50

    $739,000

    Sold Oct 17, 2025

    425 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,586 Sq Ft
    • Built 1998

    Last Sold Summary

    • $466/SF
    • 32 Days On Market

    Current Estimated Value $723,013

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    425 Mountainview Dr, Oakland, MD 21550
    • 91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      91 Mallard Loop, Oakland, MD 21550
      /48

      Est $739,025

      Not Listed For Sale

      91 Mallard Loop, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 4,508 Sq Ft
      • Built 1997
      91 Mallard Loop, Oakland, MD 21550

      Last Sold Summary

      • 45 Days On Market

  • 3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    /80

    $1,270,000

    Sold Oct 16, 2025

    3273 Lake Shore Dr, Oakland, MD 21550

    • 6 Beds
    • 3 Baths
    • 1,714 Sq Ft
    • Built 1930

    Last Sold Summary

    • $741/SF
    • 6 Days On Market

    Current Estimated Value $1,241,878

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    3273 Lake Shore Dr, Oakland, MD 21550
    • 1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      1356 Stockslager Rd, Oakland, MD 21550
      /63

      Est $1,899,227

      Not Listed For Sale

      1356 Stockslager Rd, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,070 Sq Ft
      • Built 1997
      1356 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 229 Days On Market

  • Lot 25 W Big Piney Dr, Oakland, MD 21550
    Lot 25 W Big Piney Dr, Oakland, MD 21550
    /2

    $3,500

    Sold Feb 13, 2026

    Lot 25 W Big Piney Dr, Oakland, MD 21550

    • Land
    • 20,037 Sq Ft
    • $7,609 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 271 Days On Market

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    Lot 25 W Big Piney Dr, Oakland, MD 21550
    • 1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      1174 Stockslager Rd, Oakland, MD 21550
      /108

      Est $1,910,805

      Not Listed For Sale

      1174 Stockslager Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,616 Sq Ft
      • Built 2011
      1174 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • 1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    /93

    $3,000,000

    Sold Dec 02, 2025

    1931 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft
    • Built 2009

    Last Sold Summary

    • $588/SF
    • 430 Days On Market

    Current Estimated Value $2,959,137

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
    • 470 W Liberty St, Oakland, MD 21550
      470 W Liberty St, Oakland, MD 21550
      470 W Liberty St, Oakland, MD 21550
      /42

      Est $320,160

      Not Listed For Sale

      470 W Liberty St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,598 Sq Ft
      • Built 2006
      470 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 54 Days On Market

Showing Results 561 - 600, Page 15 of 18

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