300

Recently Sold Homes in 21550

Section Image
  • /60

    $505,000

    Sold Nov 14, 2025

    36 Ridgewood Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft
    • Built 2000

    Last Sold Summary

    • $295/SF
    • 228 Days On Market

    Current Estimated Value $519,539

    Last Listing Agent Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
  • /24

    $85,000

    Sold Oct 03, 2025

    1101 Wheeling Ave, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft
    • Built 1950

    Last Sold Summary

    • $49/SF
    • 25 Days On Market

    Current Estimated Value $160,672

    Last Listing Agent Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
  • /13

    $60,000

    Sold Sep 24, 2025

    Lot 38 Fern Loop, Sang Run, MD 21541

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    Last Sold Summary

    • 607 Days On Market

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

    Lot 38 Fern Loop, Sang Run, MD 21541
  • /24

    $110,000

    Sold Sep 26, 2025

    110 W Pennington St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1946

    Last Sold Summary

    • $143/SF
    • 12 Days On Market

    Current Estimated Value $115,976

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

    110 W Pennington St, Oakland, MD 21550
  • /45

    $150,000

    Sold Aug 14, 2025

    414 D St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1950

    Last Sold Summary

    • $160/SF
    • 4 Days On Market

    Current Estimated Value $153,195

    Last Listing Agent Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    414 D St, Oakland, MD 21550
  • /13

    $50,000

    Sold Feb 06, 2026

    72 Chimney Rock Ln, Mc Henry, MD 21541

    • Land
    • 24,829 Sq Ft
    • $87,719 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 2 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    72 Chimney Rock Ln, Mc Henry, MD 21541
  • /48

    $525,000

    Sold Jul 11, 2025

    3554 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1993

    Last Sold Summary

    • $405/SF
    • 232 Days On Market

    Current Estimated Value $544,297

    Last Listing Agent Robert Krop Keller Williams Realty Centre

    3554 Lake Shore Dr, Oakland, MD 21550
  • /5

    $44,000

    Sold Aug 11, 2025

    142 Matthew Rd, Oakland, MD 21550

    • Land
    • 1.83 Acres
    • $24,044 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    142 Matthew Rd, Oakland, MD 21550
  • /48

    $229,000

    Sold Dec 15, 2025

    104 G St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • Built 1900

    Last Sold Summary

    • $142/SF
    • 26 Days On Market

    Current Estimated Value $225,564

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550
  • /20

    $195,000

    Sold Nov 12, 2025

    210 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft
    • Built 1996

    Last Sold Summary

    • $162/SF
    • 2 Days On Market

    Current Estimated Value $197,494

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
  • /40

    $560,000

    Sold Jun 20, 2025

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2009

    Last Sold Summary

    • $170/SF
    • 52 Days On Market

    Current Estimated Value $559,633

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

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
  • /32

    $232,500

    Sold Jul 10, 2025

    114 Waterwheel Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • $242/SF
    • 138 Days On Market

    Current Estimated Value $247,904

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

    114 Waterwheel Rd, Oakland, MD 21550
  • /53

    $682,567

    Sold Oct 31, 2025

    183 Kendall Camp Cir, McHenry, MD 21541

    • 4 Beds
    • 3 Baths
    • 2,135 Sq Ft
    • Built 2008

    Last Sold Summary

    • $320/SF
    • 173 Days On Market

    Current Estimated Value $704,114

    Last Listing Agent Jon Bell Railey Realty, Inc.

    183 Kendall Camp Cir, McHenry, MD 21541
  • /46

    $1,120,000

    Sold Jul 08, 2025

    636 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,028 Sq Ft
    • Built 1986

    Last Sold Summary

    • $552/SF
    • 11 Days On Market

    Current Estimated Value $1,160,338

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
  • /38

    $100,000

    Sold Jul 11, 2025

    5914 Maryland Hwy, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft
    • Built 1973

    Last Sold Summary

    • $56/SF
    • 4 Days On Market

    Current Estimated Value $176,747

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

    5914 Maryland Hwy, Oakland, MD 21550
  • /22

    $180,000

    Sold Sep 12, 2025

    4643 Oakland Sang Run Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1979

    Last Sold Summary

    • $208/SF
    • 4 Days On Market

    Current Estimated Value $200,952

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
  • /45

    $750,000

    Sold Jan 16, 2026

    198 Grandview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft
    • Built 2003

    Last Sold Summary

    • $273/SF
    • 150 Days On Market

    Current Estimated Value $782,244

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
  • /12

    $75,000

    Sold Jul 10, 2025

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550

    • Land
    • 1.1 Acres
    • $68,182 per Acre

    Last Sold Summary

    • 7 Days On Market

    Last Listing Agent Lucas Muenchow Railey Realty, Inc.

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
  • /65

    $558,000

    Sold Nov 10, 2025

    72 Cliff Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $256/SF
    • 32 Days On Market

    Current Estimated Value $598,945

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
  • /65

    $379,000

    Sold Oct 08, 2025

    113 G St, Oakland, MD 21550

    • 9 Beds
    • 3.5 Baths
    • 3,840 Sq Ft
    • Built 1903

    Last Sold Summary

    • $99/SF
    • 40 Days On Market

    Current Estimated Value $390,655

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

    113 G St, Oakland, MD 21550
  • /31

    $189,000

    Sold Jul 24, 2025

    1681 Shady Dell Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1985

    Last Sold Summary

    • $197/SF
    • 2 Days On Market

    Current Estimated Value $188,805

    Last Listing Agent Tim Macauley Taylor-Made Deep Creek Real Estate, LLC

    1681 Shady Dell Rd, Oakland, MD 21550
  • /6

    $30,000

    Sold Oct 23, 2025

    28 Wild Turkey Ln, Oakland, MD 21550

    • Land
    • 1 Acre
    • $30,000 per Acre

    Last Sold Summary

    • 14 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    28 Wild Turkey Ln, Oakland, MD 21550
  • /51

    $435,000

    Sold May 27, 2025

    234 Maple Del Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,750 Sq Ft
    • Built 1995

    Last Sold Summary

    • $158/SF
    • 306 Days On Market

    Current Estimated Value $474,689

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

    234 Maple Del Ln, Oakland, MD 21550
  • /62

    $349,900

    Sold May 08, 2026

    16 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft
    • Built 1974

    Last Sold Summary

    • $317/SF
    • 128 Days On Market

    Current Estimated Value $673,948

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, Oakland, MD 21550
  • /34

    $275,000

    Sold Jan 02, 2026

    34 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1992

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $325,315

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

    34 Laurel Brook Dr, Oakland, MD 21550
  • /48

    $205,000

    Sold Mar 20, 2026

    565 Glendale Rd Unit 312, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Built 2006

    Last Sold Summary

    • 10% Below List Price
    • $261/SF
    • 6 Days On Market

    Current Estimated Value $291,704

    Last Listing Agent Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 312, Oakland, MD 21550
  • /47

    $285,000

    Sold Oct 31, 2025

    1764 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft
    • Built 1968

    Last Sold Summary

    • $124/SF
    • 175 Days On Market

    Current Estimated Value $281,723

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

    1764 Underwood Rd, Oakland, MD 21550
  • /56

    $697,000

    Sold Dec 19, 2025

    969 Hoyes Run Rd, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft
    • Built 1998

    Last Sold Summary

    • $193/SF
    • 180 Days On Market

    Current Estimated Value $719,497

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
  • /2

    $10,000

    Sold Dec 19, 2025

    0 Maryland Hwy, Swanton, MD 21561

    • Land
    • 1.6 Acres
    • $6,250 per Acre

    Last Sold Summary

    • 220 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    0 Maryland Hwy, Swanton, MD 21561
  • /29

    $225,000

    Sold Nov 17, 2025

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550

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

    Last Sold Summary

    • $433/SF
    • 26 Days On Market

    Current Estimated Value $228,603

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
  • /39

    $195,000

    Sold Nov 12, 2025

    501 Christophers Way, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1994

    Last Sold Summary

    • $121/SF
    • 138 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    501 Christophers Way, Oakland, MD 21550
  • /41

    $218,000

    Sold Dec 01, 2025

    1136 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1971

    Last Sold Summary

    • $206/SF
    • 7 Days On Market

    Current Estimated Value $223,138

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

    1136 Black Oak Dr, Oakland, MD 21550
  • /18

    $200,000

    Sold Sep 15, 2025

    2571 Shady Dell Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1985

    Last Sold Summary

    • $119/SF
    • 62 Days On Market

    Current Estimated Value $221,004

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
  • /93

    $1,445,000

    Sold Nov 14, 2025

    128 Big Bass Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • Built 2023

    Last Sold Summary

    • $336/SF
    • 13 Days On Market

    Current Estimated Value $1,447,498

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
  • /78

    $1,780,000

    Sold Dec 19, 2025

    2345 Marsh Hill Rd, Mc Henry, MD 21541

    • 6 Beds
    • 6 Baths
    • 5,373 Sq Ft
    • Built 1990

    Last Sold Summary

    • $331/SF
    • 53 Days On Market

    Current Estimated Value $1,776,747

    Last Listing Agent James Matthews Taylor-Made Deep Creek Real Estate, LLC

    2345 Marsh Hill Rd, Mc Henry, MD 21541
  • /56

    $320,000

    Sold Nov 05, 2025

    531 S 3rd St, Oakland, MD 21550

    • 5 Beds
    • 2.5 Baths
    • 2,477 Sq Ft
    • Built 1920

    Last Sold Summary

    • $129/SF
    • 118 Days On Market

    Current Estimated Value $321,785

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
  • /52

    $840,000

    Sold Jan 31, 2026

    35 Blue Mountain View, McHenry, MD 21541

    • 5 Beds
    • 4.5 Baths
    • 2,832 Sq Ft
    • Built 2022

    Last Sold Summary

    • 16% Below List Price
    • $297/SF
    • 221 Days On Market

    Current Estimated Value $825,981

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    35 Blue Mountain View, McHenry, MD 21541
  • /71

    $590,000

    Sold Jan 16, 2026

    3084 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft
    • Built 1999

    Last Sold Summary

    • $239/SF
    • 305 Days On Market

    Current Estimated Value $620,209

    Last Listing Agent Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
  • /47

    $1,762,500

    Sold Jul 29, 2025

    1484 Paradise Point Rd, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,360 Sq Ft
    • Built 2022

    Last Sold Summary

    • $525/SF
    • 16 Days On Market

    Current Estimated Value $1,808,023

    Last Listing Agent Kelsey Meyers Railey Realty, Inc.

    1484 Paradise Point Rd, Oakland, MD 21550
  • /68

    $310,000

    Sold Jul 31, 2025

    707 Sunshine Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft
    • Built 2004

    Last Sold Summary

    • $151/SF
    • 94 Days On Market

    Current Estimated Value $321,966

    Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

    707 Sunshine Dr, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 8

How to Buy a Home How to Finance a Home How to Sell a Home