10,714

Oakland, MD Homes

Section Image
  • 462 Skippers Point Rd, Oakland, MD 21550
    462 Skippers Point Rd, Oakland, MD 21550
    462 Skippers Point Rd, Oakland, MD 21550
    /66

    $490,000 Sold Aug 08, 2025

    462 Skippers Point Rd, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1983

    Last Sold Summary

    • $302/SF
    • 51 Days On Market

    Current Estimated Value $505,329

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    462 Skippers Point Rd, Oakland, MD 21550
    • 2236 Paradise Point Rd, Oakland, MD 21550
      2236 Paradise Point Rd, Oakland, MD 21550
      2236 Paradise Point Rd, Oakland, MD 21550
      /80

      Est $1,472,322 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,004 Sq Ft

      2236 Paradise Point Rd, Oakland, MD 21550

      2236 Paradise Point Rd, Oakland, MD 21550
  • 600 Hope Ave, Oakland, MD 21550
    600 Hope Ave, Oakland, MD 21550
    600 Hope Ave, Oakland, MD 21550
    /44

    $225,000 Sold Jul 18, 2025

    600 Hope Ave, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,480 Sq Ft
    • Built 1981

    Last Sold Summary

    • $91/SF
    • 21 Days On Market

    Current Estimated Value $228,060

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    600 Hope Ave, Oakland, MD 21550
    • 591 Calderwood Rd, Oakland, MD 21550
      591 Calderwood Rd, Oakland, MD 21550
      591 Calderwood Rd, Oakland, MD 21550
      /67

      Est $395,113 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,191 Sq Ft

      591 Calderwood Rd, Oakland, MD 21550

      591 Calderwood Rd, Oakland, MD 21550
  • 473 Cumberland Rd, Oakland, MD 21550
    473 Cumberland Rd, Oakland, MD 21550
    473 Cumberland Rd, Oakland, MD 21550
    /35

    $285,000 Sold Nov 13, 2025

    473 Cumberland Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $205/SF
    • 155 Days On Market

    Last Listing Agent Jeremy McDonough Mr. Lister Realty

    473 Cumberland Rd, Oakland, MD 21550
    • 128 Shaffer Ln, Oakland, MD 21550
      128 Shaffer Ln, Oakland, MD 21550
      128 Shaffer Ln, Oakland, MD 21550
      /27

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,040 Sq Ft

      128 Shaffer Ln, Oakland, MD 21550

      128 Shaffer Ln, Oakland, MD 21550
  • 180 Winding Trail Ln Unit 5A, Oakland, MD 21550
    180 Winding Trail Ln Unit 5A, Oakland, MD 21550
    180 Winding Trail Ln Unit 5A, Oakland, MD 21550
    /69

    $535,000 Sold Mar 21, 2025

    180 Winding Trail Ln Unit 5A, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft
    • Built 2006

    Last Sold Summary

    • $178/SF
    • 277 Days On Market

    Current Estimated Value $539,417

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

    180 Winding Trail Ln Unit 5A, Oakland, MD 21550
    • 400 E St, Oakland, MD 21550
      400 E St, Oakland, MD 21550
      400 E St, Oakland, MD 21550
      /74

      Est $195,082 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft

      400 E St, Oakland, MD 21550

      400 E St, Oakland, MD 21550
  • 19 Pheasant Run, Oakland, MD 21550
    19 Pheasant Run, Oakland, MD 21550
    19 Pheasant Run, Oakland, MD 21550
    /20

    $55,000 Sold Nov 17, 2025

    19 Pheasant Run, Oakland, MD 21550

    • Land
    • 2.84 Acres
    • $19,366 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    19 Pheasant Run, Oakland, MD 21550
    • 67 Fireside Rd, Oakland, MD 21550
      67 Fireside Rd, Oakland, MD 21550
      67 Fireside Rd, Oakland, MD 21550
      /32

      Est $330,786 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft

      67 Fireside Rd, Oakland, MD 21550

      67 Fireside Rd, Oakland, MD 21550
  • 0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    /18

    $160,000 Sold Aug 28, 2025

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550

    • Land
    • 25 Acres
    • $6,400 per Acre

    Last Sold Summary

    • 44 Days On Market

    Last Listing Agent Ally Litten Mountainside Home Realty

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    • 315 Glendale Rd, Oakland, MD 21550
      315 Glendale Rd, Oakland, MD 21550
      315 Glendale Rd, Oakland, MD 21550
      /89

      Est $2,274,019 Not Listed For Sale

      • 7 Beds
      • 4.5 Baths
      • 4,372 Sq Ft

      315 Glendale Rd, Oakland, MD 21550

      315 Glendale Rd, Oakland, MD 21550
  • 247 Sloan Tract Rd, Oakland, MD 21550
    247 Sloan Tract Rd, Oakland, MD 21550
    247 Sloan Tract Rd, Oakland, MD 21550
    /49

    $461,000 Sold Feb 14, 2025

    247 Sloan Tract Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2004

    Last Sold Summary

    • $356/SF
    • 3 Days On Market

    Current Estimated Value $481,981

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    247 Sloan Tract Rd, Oakland, MD 21550
    • 116 S Oakhall Dr, Oakland, MD 21550
      116 S Oakhall Dr, Oakland, MD 21550
      116 S Oakhall Dr, Oakland, MD 21550
      /35

      Est $262,074 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      116 S Oakhall Dr, Oakland, MD 21550

      116 S Oakhall Dr, Oakland, MD 21550
  • 604 Harvey Winters Dr, Oakland, MD 21550
    604 Harvey Winters Dr, Oakland, MD 21550
    604 Harvey Winters Dr, Oakland, MD 21550
    /121

    $685,000 Sold Jan 31, 2025

    604 Harvey Winters Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,982 Sq Ft
    • Built 1988

    Last Sold Summary

    • $172/SF
    • 48 Days On Market

    Current Estimated Value $697,297

    Last Listing Agent Justin Liller Railey Realty, Inc.

    604 Harvey Winters Dr, Oakland, MD 21550
    • 419 Seneca Ave, Oakland, MD 21550
      419 Seneca Ave, Oakland, MD 21550
      419 Seneca Ave, Oakland, MD 21550
      /26

      Est $154,676 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,184 Sq Ft

      419 Seneca Ave, Oakland, MD 21550

      419 Seneca Ave, Oakland, MD 21550
  • 1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    /53

    $1,500,000 Sold Dec 01, 2025

    1674 Paradise Point Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 465 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
    • 581 Skippers Point Rd, Oakland, MD 21550
      581 Skippers Point Rd, Oakland, MD 21550
      581 Skippers Point Rd, Oakland, MD 21550
      /62

      Est $1,461,181 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft

      581 Skippers Point Rd, Oakland, MD 21550

      581 Skippers Point Rd, Oakland, MD 21550
  • 8 Winding Trail Ln Unit 1, Oakland, MD 21550
    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    /66

    $575,000 Sold Apr 04, 2025

    8 Winding Trail Ln Unit 1, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2006

    Last Sold Summary

    • $174/SF
    • 174 Days On Market

    Current Estimated Value $576,677

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    • 233 N 2nd St, Oakland, MD 21550
      233 N 2nd St, Oakland, MD 21550
      233 N 2nd St, Oakland, MD 21550
      /87

      Est $326,252 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,218 Sq Ft

      233 N 2nd St, Oakland, MD 21550

      233 N 2nd St, Oakland, MD 21550
  • 353 Basswood Way Unit 24, Oakland, MD 21550
    353 Basswood Way Unit 24, Oakland, MD 21550
    353 Basswood Way Unit 24, Oakland, MD 21550
    /64

    $695,000 Sold Oct 09, 2025

    353 Basswood Way Unit 24, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 2005

    Last Sold Summary

    • $261/SF
    • 14 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
    • 503 Tower St, Oakland, MD 21550
      503 Tower St, Oakland, MD 21550
      503 Tower St, Oakland, MD 21550
      /20

      Est $172,159 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 856 Sq Ft

      503 Tower St, Oakland, MD 21550

      503 Tower St, Oakland, MD 21550
  • 1006 Lake Shore Dr, Oakland, MD 21550
    1006 Lake Shore Dr, Oakland, MD 21550
    1006 Lake Shore Dr, Oakland, MD 21550
    /61

    $650,000 Sold Aug 21, 2025

    1006 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1993

    Last Sold Summary

    • $336/SF
    • 27 Days On Market

    Current Estimated Value $653,440

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
    • 1094 Eagle Rock Rd, Oakland, MD 21550
      1094 Eagle Rock Rd, Oakland, MD 21550
      1094 Eagle Rock Rd, Oakland, MD 21550
      /76

      Est $639,780 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,780 Sq Ft

      1094 Eagle Rock Rd, Oakland, MD 21550

      1094 Eagle Rock Rd, Oakland, MD 21550
  • 601 Hope Ave, Oakland, MD 21550
    601 Hope Ave, Oakland, MD 21550
    601 Hope Ave, Oakland, MD 21550
    /38

    $398,350 Sold May 07, 2025

    601 Hope Ave, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,142 Sq Ft
    • Built 2025

    Last Sold Summary

    • $186/SF
    • 0 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    601 Hope Ave, Oakland, MD 21550
    • 700 N St, Oakland, MD 21550
      700 N St, Oakland, MD 21550
      700 N St, Oakland, MD 21550
      /34

      Est $205,522 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,724 Sq Ft

      700 N St, Oakland, MD 21550

      700 N St, Oakland, MD 21550
  • 215 N 10th St, Oakland, MD 21550
    215 N 10th St, Oakland, MD 21550
    215 N 10th St, Oakland, MD 21550
    /48

    $279,000 Sold Sep 25, 2025

    215 N 10th St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,518 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Below List Price
    • $184/SF
    • 6 Days On Market

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    215 N 10th St, Oakland, MD 21550
    • 134 Skippers Ln, Oakland, MD 21550
      134 Skippers Ln, Oakland, MD 21550
      134 Skippers Ln, Oakland, MD 21550
      /46

      Est $346,639 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,497 Sq Ft

      134 Skippers Ln, Oakland, MD 21550

      134 Skippers Ln, Oakland, MD 21550
  • 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 Vacations & Sales

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    • 1634 Shady Dell Rd, Oakland, MD 21550
      1634 Shady Dell Rd, Oakland, MD 21550
      1634 Shady Dell Rd, Oakland, MD 21550
      /48

      Est $222,361 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,176 Sq Ft

      1634 Shady Dell Rd, Oakland, MD 21550

      1634 Shady Dell Rd, Oakland, MD 21550
  • 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 $600,934

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    245 Santa fe Trail, Oakland, MD 21550
    • 685 Oakland Dr, Oakland, MD 21550
      685 Oakland Dr, Oakland, MD 21550
      685 Oakland Dr, Oakland, MD 21550
      /51

      Est $250,016 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,378 Sq Ft

      685 Oakland Dr, Oakland, MD 21550

      685 Oakland Dr, Oakland, MD 21550
  • 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

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

    2045 Swallow Falls Rd, Oakland, MD 21550
    • 248 Markwood Dr, Oakland, MD 21550
      248 Markwood Dr, Oakland, MD 21550
      248 Markwood Dr, Oakland, MD 21550
      /84

      Est $958,387 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 4,739 Sq Ft

      248 Markwood Dr, Oakland, MD 21550

      248 Markwood Dr, Oakland, MD 21550
  • 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 $582,385

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    • 615 E High St, Oakland, MD 21550
      615 E High St, Oakland, MD 21550
      615 E High St, Oakland, MD 21550
      /22

      Est $207,696 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,180 Sq Ft

      615 E High St, Oakland, MD 21550

      615 E High St, Oakland, MD 21550
  • 112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    /4

    $73,900 Sold May 12, 2025

    112 E Pennington St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,380 Sq Ft
    • Built 1916

    Last Sold Summary

    • $54/SF
    • 1 Day On Market

    Current Estimated Value $109,228

    Last Listing Agent Robert Custer Custer Realty & Auction

    112 E Pennington St, Oakland, MD 21550
    • 524 Bray School Rd, Oakland, MD 21550
      524 Bray School Rd, Oakland, MD 21550
      524 Bray School Rd, Oakland, MD 21550
      /87

      Est $495,176 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,536 Sq Ft

      524 Bray School Rd, Oakland, MD 21550

      524 Bray School Rd, Oakland, MD 21550
  • 815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    /17

    $15,000 Sold Jul 09, 2025

    815 L St, Oakland, MD 21550

    • Land
    • 0.28 Acre
    • $53,571 per Acre

    Last Sold Summary

    • 1 Day On Market

    Current Estimated Value $94,477

    Last Listing Agent Lauren McCann Railey Realty, Inc.

    815 L St, Oakland, MD 21550
    • 514 M St, Oakland, MD 21550
      514 M St, Oakland, MD 21550
      514 M St, Oakland, MD 21550
      /38

      Est $182,814 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,326 Sq Ft

      514 M St, Oakland, MD 21550

      514 M St, Oakland, MD 21550

Showing Results 481 - 520, Page 13 of 18

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