317

Recently Sold Homes in 21550

Section Image
  • 17 Laurel Brook Dr, Oakland, MD 21550
    17 Laurel Brook Dr, Oakland, MD 21550
    17 Laurel Brook Dr, Oakland, MD 21550
    /21

    $275,000 Sold Apr 11, 2025

    17 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,840 Sq Ft
    • Built 1991

    Last Sold Summary

    • $149/SF
    • 171 Days On Market

    Current Estimated Value $285,140

    Last Listing Agent Michael Cumerlato Jason Mitchell Group

    17 Laurel Brook Dr, Oakland, MD 21550
  • 1989 Lake Shore Dr, Oakland, MD 21550
    1989 Lake Shore Dr, Oakland, MD 21550
    1989 Lake Shore Dr, Oakland, 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

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1989 Lake Shore Dr, Oakland, MD 21550
  • 11 Sunset Dr, Oakland, MD 21550
    11 Sunset Dr, Oakland, MD 21550
    11 Sunset 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

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

    11 Sunset Dr, Oakland, MD 21550
  • 180 Roman Ridge Rd Unit 18, Oakland, MD 21550
    180 Roman Ridge Rd Unit 18, Oakland, MD 21550
    180 Roman Ridge Rd Unit 18, Oakland, MD 21550
    /55

    $503,000 Sold Mar 28, 2025

    180 Roman Ridge Rd Unit 18, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 2,608 Sq Ft
    • Built 2005

    Last Sold Summary

    • $193/SF
    • 232 Days On Market

    Current Estimated Value $509,979

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    180 Roman Ridge Rd Unit 18, Oakland, MD 21550
  • 307 Sciota St, Oakland, MD 21550
    307 Sciota St, Oakland, MD 21550
    307 Sciota St, Oakland, MD 21550
    /39

    $259,000 Sold Feb 25, 2025

    307 Sciota St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,144 Sq Ft
    • Built 1985

    Last Sold Summary

    • $121/SF
    • 3 Days On Market

    Current Estimated Value $260,964

    Last Listing Agent Ben Maust Railey Realty, Inc.

    307 Sciota St, Oakland, MD 21550
  • 741 Hoyes Run Rd, Oakland, MD 21550
    741 Hoyes Run Rd, Oakland, MD 21550
    741 Hoyes Run Rd, Oakland, MD 21550
    /56

    $500,000 Sold Jan 23, 2025

    741 Hoyes Run Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1984

    Last Sold Summary

    • $231/SF
    • 10 Days On Market

    Current Estimated Value $536,333

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    741 Hoyes Run Rd, Oakland, MD 21550
  • 3472 Lake Shore Dr, Oakland, MD 21550
    3472 Lake Shore Dr, Oakland, MD 21550
    3472 Lake Shore 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 $773,363

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    3472 Lake Shore Dr, Oakland, MD 21550
  • 723 E Oak St, Oakland, MD 21550
    723 E Oak St, Oakland, MD 21550
    723 E Oak St, 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 $135,286

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    723 E Oak St, Oakland, MD 21550
  • 134 Black Diamond Ct, McHenry, MD 21541
    134 Black Diamond Ct, McHenry, MD 21541
    /2

    $49,990 Sold Mar 05, 2025

    134 Black Diamond Ct, McHenry, MD 21541

    • Land
    • 0.57 Acre
    • $87,702 per Acre

    Last Sold Summary

    • 43 Days On Market

    Last Listing Agent Jesse Hoffman HomeSmart

    134 Black Diamond Ct, McHenry, MD 21541
  • Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, 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
  • 1589 Lake Shore Dr, Oakland, MD 21550
    1589 Lake Shore Dr, Oakland, MD 21550
    1589 Lake Shore Dr, 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 $1,410,562

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    1589 Lake Shore Dr, Oakland, MD 21550
  • 108 Sundance Way, McHenry, MD 21541
    108 Sundance Way, McHenry, MD 21541
    108 Sundance Way, McHenry, MD 21541
    /12

    $68,500 Sold Feb 28, 2025

    108 Sundance Way, McHenry, MD 21541

    • Land
    • 0.76 Acre
    • $90,132 per Acre

    Last Sold Summary

    • 45% Below List Price
    • 1,010 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    108 Sundance Way, McHenry, MD 21541
  • 10 AC Shingle Camp Rd, Sang Run, MD 21541
    10 AC Shingle Camp Rd, Sang Run, MD 21541
    10 AC Shingle Camp Rd, Sang Run, MD 21541
    /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
  • 17 Driftwood Ln, Oakland, MD 21550
    17 Driftwood Ln, Oakland, MD 21550
    17 Driftwood Ln, Oakland, MD 21550
    /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

    Last Listing Agent Larry Smith Railey Realty, Inc.

    17 Driftwood Ln, Oakland, MD 21550
  • 0 Fox Tail Rd, 6, Sang Run, MD 21550
    0 Fox Tail Rd, 6, Sang Run, MD 21550
    0 Fox Tail Rd, 6, Sang Run, 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
  • 627 Hamill St, Oakland, MD 21550
    627 Hamill St, Oakland, MD 21550
    627 Hamill St, Oakland, 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

    Last Listing Agent Rich Orr Railey Realty, Inc.

    627 Hamill St, Oakland, MD 21550
  • 150 Greenbrier Dr, Mc Henry, MD 21541
    150 Greenbrier Dr, Mc Henry, MD 21541
    150 Greenbrier Dr, Mc Henry, MD 21541
    /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

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

    150 Greenbrier Dr, Mc Henry, MD 21541
  • Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    /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
  • 107 E Mason St, Oakland, MD 21550
    107 E Mason St, Oakland, MD 21550
    107 E Mason St, Oakland, MD 21550
    /24

    $27,500 Sold May 14, 2025

    107 E Mason St, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,256 Sq Ft
    • Built 1914

    Last Sold Summary

    • $12/SF
    • 18 Days On Market

    Current Estimated Value $167,299

    Last Listing Agent Kathleen Miller Better Homes & Gardens Real Estate Old Line Group

    107 E Mason St, Oakland, MD 21550
  • 29 Sloan Tract Rd, Oakland, MD 21550
    29 Sloan Tract Rd, Oakland, MD 21550
    29 Sloan Tract 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 $281,137

    Last Listing Agent Thomas Long Railey Realty, Inc.

    29 Sloan Tract Rd, Oakland, MD 21550
  • 228 Paradise Heights, Oakland, MD 21550
    228 Paradise Heights, Oakland, MD 21550
    228 Paradise Heights, 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 $1,888,632

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

    228 Paradise Heights, Oakland, MD 21550
  • 366 Glendale Rd, Oakland, MD 21550
    366 Glendale Rd, Oakland, MD 21550
    366 Glendale Rd, 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

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
  • 1014 Madison St, Oakland, MD 21550
    1014 Madison St, Oakland, MD 21550
    1014 Madison St, Oakland, MD 21550
    /69

    $450,000 Sold Feb 26, 2025

    1014 Madison St, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,016 Sq Ft
    • Built 1988

    Last Sold Summary

    • $149/SF
    • 21 Days On Market

    Current Estimated Value $463,086

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1014 Madison St, Oakland, MD 21550
  • Lot 76 Sundance Way, McHenry, MD 21541
    Lot 76 Sundance Way, McHenry, MD 21541
    Lot 76 Sundance Way, McHenry, MD 21541
    /11

    $66,250 Sold Mar 31, 2025

    Lot 76 Sundance Way, McHenry, MD 21541

    • Land
    • 0.57 Acre
    • $116,228 per Acre

    Last Sold Summary

    • 184 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    Lot 76 Sundance Way, McHenry, MD 21541
  • 157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    157 Jeffrey Ln Unit 21A, 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

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
  • 297 Paradise Point Rd, Oakland, MD 21550
    297 Paradise Point Rd, Oakland, MD 21550
    297 Paradise Point Rd, Oakland, MD 21550
    /41

    $315,000 Sold Feb 14, 2025

    297 Paradise Point Rd, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 3,024 Sq Ft
    • Built 2005

    Last Sold Summary

    • $104/SF
    • 210 Days On Market

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

    297 Paradise Point Rd, Oakland, MD 21550
  • 1714 Mayhew Inn Rd, Oakland, MD 21550
    1714 Mayhew Inn Rd, Oakland, MD 21550
    1714 Mayhew Inn Rd, 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

    Current Estimated Value $127,546

    Last Listing Agent Brian Homberg Taylor Made Deep Creek Vacations & Sales

    1714 Mayhew Inn Rd, Oakland, MD 21550
  • 939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    939 Glendale 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 $588,703

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
  • 306 Shady Acre Ln, Oakland, MD 21550
    306 Shady Acre Ln, Oakland, MD 21550
    306 Shady Acre Ln, 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

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
  • 12 Laurel Ct, Oakland, MD 21550
    12 Laurel Ct, Oakland, MD 21550
    /2

    $55,000 Sold Feb 03, 2025

    12 Laurel Ct, Oakland, MD 21550

    • Land
    • 0.72 Acre
    • $76,389 per Acre

    Last Sold Summary

    • 44% Below List Price
    • 1,251 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    12 Laurel Ct, Oakland, MD 21550
  • Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
    Lots 57 & 58 Black Oak Ln, 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
  • 590 S Blakeslee Rd, Oakland, MD 21550
    590 S Blakeslee Rd, Oakland, MD 21550
    590 S Blakeslee Rd, 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

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    590 S Blakeslee Rd, Oakland, MD 21550
  • 9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    /4

    $140,000 Sold Mar 17, 2025

    9.3 +/- Acres Upperman Rd, Oakland, MD 21550

    • Land
    • 9.2 Acres
    • $15,217 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
  • 158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    /49

    $790,000 Sold May 09, 2025

    158 Silver Tree Ln, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,250 Sq Ft
    • Built 2003

    Last Sold Summary

    • $351/SF
    • 79 Days On Market

    Current Estimated Value $839,144

    Last Listing Agent Jon Bell Railey Realty, Inc.

    158 Silver Tree Ln, Oakland, MD 21550
  • 20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    /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
  • 0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    /16

    $100,000 Sold May 02, 2025

    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550

    • Land
    • 2.4 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 433 Days On Market

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

    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
  • 15 D St, Oakland, MD 21550
    15 D St, Oakland, MD 21550
    15 D St, 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 $155,222

    Last Listing Agent Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
  • 58 Glendale Woods Rd, Oakland, MD 21550
    58 Glendale Woods Rd, Oakland, MD 21550
    58 Glendale Woods Rd, 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

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
  • 0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, Oakland, MD 21550
    /14

    $80,000 Sold Sep 26, 2025

    0 Coolidge Ave, Oakland, MD 21550

    • Land
    • 0.46 Acre
    • $173,913 per Acre

    Last Sold Summary

    • 76 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 Coolidge Ave, Oakland, MD 21550
  • 45 Village Dr Unit 4, Oakland, MD 21550
    45 Village Dr Unit 4, Oakland, MD 21550
    45 Village Dr Unit 4, 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

    Last Listing Agent Ana Dubin RE/MAX Realty Group

    45 Village Dr Unit 4, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 8

Maryland Garrett County Oakland 21550

Recently Sold Real Estate & Homes in 21550

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