10,739

Oakland, MD Homes

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  • /72

    $975,000 Sold Sep 25, 2025

    267 Woodlands Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft
    • Built 2021

    Last Sold Summary

    • $437/SF
    • 136 Days On Market

    Current Estimated Value $1,018,371

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

    267 Woodlands Hill Ln, Oakland, MD 21550
    • /63

      Est $546,425 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

      • 6% Above List Price
      • $466/SF
      • 178 Days On Market

      Last Sold Price $515,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /127

    $2,550,000 Sold Aug 01, 2025

    1100 S Blakeslee Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 6,572 Sq Ft
    • Built 1998

    Last Sold Summary

    • $388/SF
    • 0 Days On Market

    Current Estimated Value $2,655,634

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    1100 S Blakeslee Rd, Oakland, MD 21550
    • /30

      Est $1,174,432 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

      • 7% Above List Price
      • 80 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Amy Mangum Railey Realty, Inc.

  • /73

    $530,000 Sold Oct 03, 2025

    346 Skippers Point Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1976

    Last Sold Summary

    • $294/SF
    • 50 Days On Market

    Current Estimated Value $558,996

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, Oakland, MD 21550
    • /35

      Est $1,464,010 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

      • 8% Below List Price
      • $2,222/SF
      • 38 Days On Market

      Last Sold Price $1,600,000

      Last Listing Agent Steven Ritchie Railey Realty, Inc.

  • /53

    $1,300,000 Sold Apr 30, 2025

    735 Winston Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,076 Sq Ft
    • Built 1985

    Last Sold Summary

    • $626/SF
    • 10 Days On Market

    Current Estimated Value $85,000

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

    735 Winston Rd, Oakland, MD 21550
    • /48

      Est $782,307 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

      • 8% Above List Price
      • $161/SF
      • 45 Days On Market

      Last Sold Price $725,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /82

    $554,999 Sold Oct 03, 2025

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2007

    Last Sold Summary

    • $168/SF
    • 164 Days On Market

    Current Estimated Value $558,475

    Last Listing Agent Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    • /63

      Est $1,797,403 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

      • 10% Below List Price
      • $648/SF
      • 229 Days On Market

      Last Sold Price $1,990,000

      Last Listing Agent Steven Ritchie Railey Realty, Inc.

  • /12

    $380,000 Sold May 30, 2025

    Lot 76 S Blakeslee Rd, Oakland, MD 21550

    • Land
    • 1.06 Acres
    • $358,491 per Acre

    Last Sold Summary

    • 4 Days On Market

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

    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    • /108

      Est $1,832,926 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

      • 7% Below List Price
      • $756/SF
      • 0 Days On Market

      Last Sold Price $1,977,000

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /72

    $835,000 Sold Mar 27, 2026

    139 Overlook Ridge Dr, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,846 Sq Ft
    • Built 2004

    Last Sold Summary

    • $293/SF
    • 340 Days On Market

    Current Estimated Value $824,096

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

    139 Overlook Ridge Dr, Oakland, MD 21550
    • /42

      Est $338,628 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

      • 10% Above List Price
      • $193/SF
      • 54 Days On Market

      Last Sold Price $309,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /58

    $249,000 Sold Mar 20, 2026

    711 Heritage Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2000

    Last Sold Summary

    • $178/SF
    • 6 Days On Market

    Current Estimated Value $246,506

    Last Listing Agent Rich Orr Railey Realty, Inc.

    711 Heritage Dr, Oakland, MD 21550
    • /55

      Est $367,946 Not Listed For Sale

      1262 Memorial Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,345 Sq Ft
      • Built 1992
      1262 Memorial Dr, Oakland, MD 21550

      Last Sold Summary

      • 17% Above List Price
      • $134/SF
      • 95 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /60

    $280,000 Sold Nov 14, 2025

    1056 Sunrise Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,528 Sq Ft
    • Built 1976

    Last Sold Summary

    • $183/SF
    • 59 Days On Market

    Current Estimated Value $273,941

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

    1056 Sunrise Dr, Oakland, MD 21550
    • /42

      Est $256,766 Not Listed For Sale

      600 S 3rd St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1955
      600 S 3rd St, Oakland, MD 21550

      Last Sold Summary

      • 1% Below List Price
      • $137/SF
      • 4 Days On Market

      Last Sold Price $259,000

      Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

  • /5

    $135,000 Sold Jun 25, 2025

    Lot #5 Swan Meadow Dr, Oakland, MD 21550

    • Land
    • 10 Acres
    • $13,500 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    • /51

      Est $422,381 Not Listed For Sale

      305 Crook Crest Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,800 Sq Ft
      • Built 1891
      305 Crook Crest Rd, Oakland, MD 21550

      Last Sold Summary

      • 2% Above List Price
      • $148/SF
      • 3 Days On Market

      Last Sold Price $415,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /149

    $2,975,000 Sold Oct 03, 2025

    1087 Pergin Farm Rd, Oakland, MD 21550

    • 6 Beds
    • 5.5 Baths
    • 4,481 Sq Ft
    • Built 1984

    Last Sold Summary

    • $664/SF
    • 16 Days On Market

    Current Estimated Value $3,060,363

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
    • /56

      Est $292,906 Not Listed For Sale

      309 Woodland Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1970
      309 Woodland Dr, Oakland, MD 21550

      Last Sold Summary

      • 15% Above List Price
      • $117/SF
      • 8 Days On Market

      Last Sold Price $255,000

      Last Listing Agent Brent Housley Railey Realty, Inc.

  • /23

    $18,000 Sold Jul 03, 2025

    Lot 9 Birchwood Dr, Oakland, MD 21550

    • Land
    • 0.8 Acre
    • $22,500 per Acre

    Last Sold Summary

    • 5 Days On Market

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

    Lot 9 Birchwood Dr, Oakland, MD 21550
    • /31

      Est $202,333 Not Listed For Sale

      219 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 1925
      219 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 2% Above List Price
      • $146/SF
      • 185 Days On Market

      Last Sold Price $198,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /35

    $390,000 Sold Dec 12, 2025

    30 Village Dr Unit 3, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 916 Sq Ft
    • Built 2005

    Last Sold Summary

    • $426/SF
    • 34 Days On Market

    Current Estimated Value $386,354

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    30 Village Dr Unit 3, Oakland, MD 21550
    • /98

      Est $335,726 Not Listed For Sale

      413 N 2nd St, Oakland, MD 21550

      • 5 Beds
      • 2.5 Baths
      • 3,472 Sq Ft
      • Built 1962
      413 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 1% Below List Price
      • $98/SF
      • 10 Days On Market

      Last Sold Price $340,000

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

  • /45

    $195,000 Sold Jul 11, 2025

    422 Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1972

    Last Sold Summary

    • $203/SF
    • 17 Days On Market

    Current Estimated Value $198,268

    Last Listing Agent Larry Smith Railey Realty, Inc.

    422 Underwood Rd, Oakland, MD 21550
    • /73

      Est $197,729 Not Listed For Sale

      708 E Reese St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,944 Sq Ft
      • Built 1926
      708 E Reese St, Oakland, MD 21550

      Last Sold Summary

      • 6% Above List Price
      • $96/SF
      • 8 Days On Market

      Last Sold Price $186,171

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /2

    $285,000 Sold Sep 05, 2025

    2360 Garrett Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 0 Days On Market

    Current Estimated Value $300,513

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    2360 Garrett Rd, Oakland, MD 21550
    • /69

      Est $232,825 Not Listed For Sale

      132 N 8th St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1940
      132 N 8th St, Oakland, MD 21550

      Last Sold Summary

      • 2% Below List Price
      • $190/SF
      • 3 Days On Market

      Last Sold Price $237,200

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

  • /47

    $208,550 Sold Sep 26, 2025

    2805 Shady Dell Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1966

    Last Sold Summary

    • $143/SF
    • 42 Days On Market

    Current Estimated Value $222,375

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    2805 Shady Dell Rd, Oakland, MD 21550
    • /36

      Est $246,442 Not Listed For Sale

      514 E Alder St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,152 Sq Ft
      • Built 1928
      514 E Alder St, Oakland, MD 21550

      Last Sold Summary

      • 5% Above List Price
      • $109/SF
      • 22 Days On Market

      Last Sold Price $235,000

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

  • /111

    $2,600,000 Sold Oct 20, 2025

    197 Black Angus Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,156 Sq Ft
    • Built 1975

    Last Sold Summary

    • $626/SF
    • 15 Days On Market

    Current Estimated Value $2,531,663

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, Oakland, MD 21550
    • /21

      Not Listed For Sale

      1400 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1990
      1400 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • $94/SF
      • 27 Days On Market

      Last Sold Price $105,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /81

    $1,200,000 Sold Jan 16, 2026

    19956 Garrett Hwy Unit 6, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • Built 2007

    Last Sold Summary

    • $400/SF
    • 162 Days On Market

    Current Estimated Value $1,181,855

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    • /67

      Est $206,033 Not Listed For Sale

      1405 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,530 Sq Ft
      • Built 1992
      1405 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 6% Below List Price
      • $144/SF
      • 3 Days On Market

      Last Sold Price $220,000

      Last Listing Agent Ashley Fadley Railey Realty, Inc.

  • /22

    $212,000 Sold Dec 05, 2025

    4 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 166 Days On Market

    Current Estimated Value $212,719

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    4 Laurel Brook Dr, Oakland, MD 21550
    • /25

      Est $142,716 Not Listed For Sale

      512 Roanoke Ave, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1976
      512 Roanoke Ave, Oakland, MD 21550

      Last Sold Summary

      • $149/SF
      • 5 Days On Market

      Last Sold Price $143,000

      Last Listing Agent Andrew Orr The KW Collective

  • /74

    $2,450,000 Sold Oct 30, 2025

    273 Glendale Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,141 Sq Ft
    • Built 2008

    Last Sold Summary

    • $477/SF
    • 7 Days On Market

    Current Estimated Value $2,493,520

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

    273 Glendale Rd, Oakland, MD 21550
    • /19

      Est $139,064 Not Listed For Sale

      204 D St, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1973
      204 D St, Oakland, MD 21550

      Last Sold Summary

      • 12% Above List Price
      • $162/SF
      • 216 Days On Market

      Last Sold Price $124,500

      Last Listing Agent Tim Macauley Taylor Made Deep Creek Real Estate

Showing Results 561 - 600, Page 15 of 18

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