300

Recently Sold Homes in 21550

Section Image
  • /2

    $399,900

    Sold May 07, 2026

    2678 Mayhew Inn Rd, Deer Park, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1971

    Last Sold Summary

    • $260/SF
    • 6 Days On Market

    Current Estimated Value $405,950

    Last Listing Agent Tina Hyatt Hyatt & Company Real Estate, LLC

    2678 Mayhew Inn Rd, Deer Park, MD 21550
  • /76

    $1,400,000

    Sold Dec 04, 2025

    1989 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,008 Sq Ft
    • Built 1964

    Last Sold Summary

    • $465/SF
    • 18 Days On Market

    Current Estimated Value $1,441,018

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1989 Lake Shore Dr, Oakland, MD 21550
  • /42

    $270,000

    Sold Nov 21, 2025

    11 Sunset Dr, Oakland, MD 21550

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

    Last Sold Summary

    • $193/SF
    • 29 Days On Market

    Current Estimated Value $278,552

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

    11 Sunset Dr, Oakland, MD 21550
  • /76

    $775,000

    Sold Aug 25, 2025

    3472 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 2,904 Sq Ft
    • Built 2007

    Last Sold Summary

    • $267/SF
    • 112 Days On Market

    Current Estimated Value $817,690

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

    3472 Lake Shore Dr, Oakland, MD 21550
  • /43

    $132,000

    Sold Aug 13, 2025

    723 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft
    • Built 1966

    Last Sold Summary

    • $134/SF
    • 2 Days On Market

    Current Estimated Value $152,848

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    723 E Oak St, Oakland, MD 21550
  • /9

    $23,000

    Sold Nov 03, 2025

    Lot 15 Little Mountain Rd, Oakland, MD 21550

    • Land
    • 2.71 Acres
    • $8,487 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 132 Days On Market

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

    Lot 15 Little Mountain Rd, Oakland, MD 21550
  • /62

    $1,399,000

    Sold Sep 05, 2025

    1589 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,872 Sq Ft
    • Built 2020

    Last Sold Summary

    • $747/SF
    • 3 Days On Market

    Current Estimated Value $1,472,718

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

    1589 Lake Shore Dr, Oakland, MD 21550
  • /17

    $250,000

    Sold Dec 19, 2025

    10 AC Shingle Camp Rd, Sang Run, MD 21541

    • Land
    • 10 Acres
    • $25,000 per Acre

    Last Sold Summary

    • 724 Days On Market

    Last Listing Agent Kelsey Meyers Railey Realty, Inc.

    10 AC Shingle Camp Rd, Sang Run, MD 21541
  • /73

    $305,000

    Sold Nov 06, 2025

    17 Driftwood Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,092 Sq Ft
    • Built 1978

    Last Sold Summary

    • $146/SF
    • 113 Days On Market

    Current Estimated Value $283,644

    Last Listing Agent Larry Smith Railey Realty, Inc.

    17 Driftwood Ln, Oakland, MD 21550
  • /15

    $26,000

    Sold Sep 18, 2025

    0 Fox Tail Rd, 6, Sang Run, MD 21550

    • Land
    • 1.58 Acres
    • $16,456 per Acre

    Last Sold Summary

    • 81 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    0 Fox Tail Rd, 6, Sang Run, MD 21550
  • /47

    $180,000

    Sold Nov 24, 2025

    627 Hamill St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,322 Sq Ft
    • Built 1886

    Last Sold Summary

    • $136/SF
    • 2 Days On Market

    Current Estimated Value $179,003

    Last Listing Agent Rich Orr Railey Realty, Inc.

    627 Hamill St, Oakland, MD 21550
  • /53

    $875,000

    Sold Nov 10, 2025

    150 Greenbrier Dr, Mc Henry, MD 21541

    • 5 Beds
    • 5.5 Baths
    • 4,345 Sq Ft
    • Built 2014

    Last Sold Summary

    • $201/SF
    • 6 Days On Market

    Current Estimated Value $873,579

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

    150 Greenbrier Dr, Mc Henry, MD 21541
  • /14

    $17,000

    Sold Dec 18, 2025

    Lot 5A Valley Rd, Oakland, MD 21550

    • Land
    • 2.45 Acres
    • $6,939 per Acre

    Last Sold Summary

    • 1,047 Days On Market

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

    Lot 5A Valley Rd, Oakland, MD 21550
  • /32

    $260,000

    Sold Jul 21, 2025

    29 Sloan Tract Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1983

    Last Sold Summary

    • $271/SF
    • 98 Days On Market

    Current Estimated Value $291,860

    Last Listing Agent Thomas Long Railey Realty, Inc.

    29 Sloan Tract Rd, Oakland, MD 21550
  • /82

    $1,900,000

    Sold May 16, 2025

    228 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 2,249 Sq Ft
    • Built 1989

    Last Sold Summary

    • $845/SF
    • 5 Days On Market

    Current Estimated Value $1,936,834

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

    228 Paradise Heights, Oakland, MD 21550
  • /29

    $369,900

    Sold Oct 17, 2025

    366 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1997

    Last Sold Summary

    • $266/SF
    • 152 Days On Market

    Current Estimated Value $376,996

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
  • /4

    $250,000

    Sold Feb 05, 2026

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550

    • Land
    • 45.7 Acres
    • $5,470 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
  • /2

    $20,000

    Sold Mar 03, 2026

    0 N Hammond St, Oakland, MD 21550

    • Land
    • 20,908 Sq Ft
    • $41,667 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 6 Days On Market

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

    0 N Hammond St, Oakland, MD 21550
  • /20

    $237,000

    Sold Oct 30, 2025

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft
    • Built 1990

    Last Sold Summary

    • $359/SF
    • 19 Days On Market

    Current Estimated Value $244,710

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

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
  • /23

    $119,000

    Sold Jul 18, 2025

    1714 Mayhew Inn Rd, Oakland, MD 21550

    • Land
    • 7.5 Acres
    • $15,867 per Acre

    Last Sold Summary

    • 56 Days On Market

    Last Listing Agent Brian Homberg Taylor-Made Deep Creek Real Estate, LLC

    1714 Mayhew Inn Rd, Oakland, MD 21550
  • /27

    $225,000

    Sold Feb 19, 2026

    1570 Garrett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft
    • Built 1984

    Last Sold Summary

    • $160/SF
    • 122 Days On Market

    Current Estimated Value $230,351

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

    1570 Garrett Rd, Oakland, MD 21550
  • /44

    $589,000

    Sold Sep 08, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft
    • Built 1995

    Last Sold Summary

    • $574/SF
    • 62 Days On Market

    Current Estimated Value $588,242

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
  • /27

    $165,000

    Sold Oct 30, 2025

    306 Shady Acre Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1972

    Last Sold Summary

    • $72/SF
    • 2 Days On Market

    Current Estimated Value $193,123

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
  • /5

    $34,500

    Sold Jan 15, 2026

    62 Crosby Dr, Oakland, MD 21550

    • Land
    • 27,442 Sq Ft
    • $54,762 per Acre

    Last Sold Summary

    • 73% Above List Price
    • 2,385 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Crosby Dr, Oakland, MD 21550
  • /20

    $17,000

    Sold Nov 21, 2025

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550

    • Land
    • 1.08 Acres
    • $15,741 per Acre

    Last Sold Summary

    • 24 Days On Market

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

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
  • /64

    $1,150,000

    Sold Oct 24, 2025

    590 S Blakeslee Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,071 Sq Ft
    • Built 2000

    Last Sold Summary

    • $374/SF
    • 102 Days On Market

    Current Estimated Value $1,156,637

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

    590 S Blakeslee Rd, Oakland, MD 21550
  • /49

    $640,000

    Sold Jan 09, 2026

    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541

    • 3 Beds
    • 3.5 Baths
    • 3,096 Sq Ft
    • Built 2004

    Last Sold Summary

    • $207/SF
    • 38 Days On Market

    Current Estimated Value $640,577

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

    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541
  • /39

    $450,000

    Sold Nov 10, 2025

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1972

    Last Sold Summary

    • $340/SF
    • 179 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
  • /44

    $140,000

    Sold Jul 08, 2025

    15 D St, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,680 Sq Ft
    • Built 1953

    Last Sold Summary

    • $83/SF
    • 86 Days On Market

    Current Estimated Value $157,922

    Last Listing Agent Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
  • /63

    $711,000

    Sold Oct 15, 2025

    58 Glendale Woods Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,556 Sq Ft
    • Built 2006

    Last Sold Summary

    • $278/SF
    • 5 Days On Market

    Current Estimated Value $740,769

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
  • /14

    $80,000

    Sold Sep 26, 2025

    0 Coolidge Ave, Oakland, MD 21550

    • Land
    • 20,037 Sq Ft
    • $173,913 per Acre

    Last Sold Summary

    • 76 Days On Market

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

    0 Coolidge Ave, Oakland, MD 21550
  • /35

    $405,000

    Sold Dec 22, 2025

    45 Village Dr Unit 4, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Built 2004

    Last Sold Summary

    • $370/SF
    • 173 Days On Market

    Current Estimated Value $404,507

    Last Listing Agent Ana Dubin RE/MAX Realty Group

    45 Village Dr Unit 4, Oakland, MD 21550
  • /36

    $326,000

    Sold Oct 10, 2025

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1997

    Last Sold Summary

    • $272/SF
    • 42 Days On Market

    Current Estimated Value $337,063

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
  • /2

    $20,000

    Sold Jun 26, 2025

    Lots 22 & 23 Black Oak Ln, Oakland, MD 21550

    • Land
    • 20,473 Sq Ft
    • $42,553 per Acre

    Last Sold Summary

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

    Lots 22 & 23 Black Oak Ln, Oakland, MD 21550
  • /69

    $1,535,000

    Sold Jan 07, 2026

    272 McComas Beach Terrace, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,448 Sq Ft
    • Built 2005

    Last Sold Summary

    • $627/SF
    • 49 Days On Market

    Current Estimated Value $1,563,903

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    272 McComas Beach Terrace, Oakland, MD 21550
  • /20

    $80,000

    Sold Jun 30, 2025

    81 Timber Ln, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 1,860 Sq Ft
    • Built 1965

    Last Sold Summary

    • $43/SF
    • 5 Days On Market

    Current Estimated Value $91,667

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    81 Timber Ln, Oakland, MD 21550
  • /21

    $155,000

    Sold May 22, 2025

    3821 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1964

    Last Sold Summary

    • $126/SF
    • 10 Days On Market

    Current Estimated Value $160,660

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

    3821 Underwood Rd, Oakland, MD 21550
  • /33

    $425,000

    Sold Dec 19, 2025

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 0 Days On Market

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

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
  • /81

    $700,000

    Sold Feb 26, 2026

    329 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,632 Sq Ft
    • Built 2004

    Last Sold Summary

    • $266/SF
    • 112 Days On Market

    Current Estimated Value $708,658

    Last Listing Agent Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
  • /18

    $19,500

    Sold Sep 04, 2025

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550

    • Land
    • 1.48 Acres
    • $13,176 per Acre

    Last Sold Summary

    • 348 Days On Market

    Last Listing Agent Brady Harden Coldwell Banker Premier

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 8

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