319

Recently Sold Homes in 21550

Section Image
  • /32

    $114,000

    Sold Jul 31, 2026

    5151 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $111/SF
    • 53 Days On Market

    Current Estimated Value $115,858

    Last Listing Agent Mark Van Tyne Julian Agency Real Estate

    5151 Hutton Rd, Oakland, MD 21550
  • /20

    $200,000

    Sold Feb 06, 2026

    123 Mountainview Ct, Oakland, MD 21550

    • Land
    • 1.69 Acres
    • $118,343 per Acre

    Last Sold Summary

    • 72 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
  • /51

    $660,000

    Sold Jan 30, 2026

    155 Basswood Way, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 268 Days On Market

    Current Estimated Value $661,053

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
  • /37

    $250,000

    Sold Dec 31, 2025

    511 E Green St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft
    • Built 1924

    Last Sold Summary

    • $133/SF
    • 176 Days On Market

    Current Estimated Value $250,919

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

    511 E Green St, Oakland, MD 21550
  • /98

    $590,000

    Sold Oct 10, 2025

    2719 Broadford Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 4,253 Sq Ft
    • Built 1984

    Last Sold Summary

    • $139/SF
    • 168 Days On Market

    Current Estimated Value $609,271

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
  • /29

    $185,000

    Sold Jan 23, 2026

    141 Truesdale Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft
    • Built 1988

    Last Sold Summary

    • $101/SF
    • 4 Days On Market

    Current Estimated Value $226,048

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

    141 Truesdale Rd, Oakland, MD 21550
  • /71

    $912,500

    Sold Dec 05, 2025

    78 Mountainside Ct, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,492 Sq Ft
    • Built 2002

    Last Sold Summary

    • $261/SF
    • 61 Days On Market

    Current Estimated Value $955,513

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

    78 Mountainside Ct, Oakland, MD 21550
  • /82

    $785,000

    Sold Jun 03, 2026

    53 Meadow Ct, Oakland, MD 21550

    • 4 Beds
    • 6 Baths
    • 3,630 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $216/SF
    • 6 Days On Market

    Current Estimated Value $793,238

    Last Listing Agent Jon Bell Railey Realty, Inc.

    53 Meadow Ct, Oakland, MD 21550
  • /87

    $867,500

    Sold Feb 20, 2026

    340 Grandview Dr, Oakland, MD 21550

    • 6 Beds
    • 4 Baths
    • 2,536 Sq Ft
    • Built 2003

    Last Sold Summary

    • $342/SF
    • 88 Days On Market

    Current Estimated Value $930,076

    Last Listing Agent Jon Bell Railey Realty, Inc.

    340 Grandview Dr, Oakland, MD 21550
  • /37

    $382,500

    Sold Feb 27, 2026

    15 Village Dr Unit 1, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • Built 2004

    Last Sold Summary

    • 408 Days On Market

    Current Estimated Value $397,583

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    15 Village Dr Unit 1, Oakland, MD 21550
  • /76

    $420,000

    Sold Oct 15, 2025

    783 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,971 Sq Ft
    • Built 2002

    Last Sold Summary

    • $213/SF
    • 122 Days On Market

    Current Estimated Value $476,076

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
  • /35

    $380,000

    Sold Sep 26, 2025

    20160 Garrett Hwy Unit G 509, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1974

    Last Sold Summary

    • $594/SF
    • 24 Days On Market

    Current Estimated Value $383,168

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

    20160 Garrett Hwy Unit G 509, Oakland, MD 21550
  • /50

    $239,000

    Sold Feb 11, 2026

    5202 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,199 Sq Ft
    • Built 1950

    Last Sold Summary

    • $199/SF
    • 149 Days On Market

    Current Estimated Value $246,742

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
  • /89

    $2,000,000

    Sold Jun 18, 2026

    209 Glendale Rd, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 3,882 Sq Ft
    • Built 2001

    Last Sold Summary

    • 5% Below List Price
    • $515/SF
    • 122 Days On Market

    Current Estimated Value $1,979,570

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    209 Glendale Rd, Oakland, MD 21550
  • /13

    $20,000

    Sold Nov 05, 2025

    0 Weber Ct, Oakland, MD 21550

    • Land
    • 10,454 Sq Ft
    • $83,333 per Acre

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    0 Weber Ct, Oakland, MD 21550
  • /58

    $1,100,000

    Sold Feb 20, 2026

    515 Winding Estates Dr, McHenry, MD 21541

    • 5 Beds
    • 5.5 Baths
    • 3,594 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $306/SF
    • 20 Days On Market

    Current Estimated Value $1,158,467

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

    515 Winding Estates Dr, McHenry, MD 21541
  • /20

    $17,000

    Sold Oct 29, 2025

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    • Land
    • 41,817 Sq Ft
    • $17,708 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
  • /2

    $8,000

    Sold Aug 29, 2025

    0 E Water St, Oakland, MD 21550

    • Land
    • 14,374 Sq Ft
    • $24,242 per Acre

    Last Sold Summary

    • 2 Days On Market

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

    0 E Water St, Oakland, MD 21550
  • /22

    $60,000

    Sold Apr 24, 2026

    3501 George Washington Hwy, Oakland, MD 21550

    • Land
    • 2.86 Acres
    • $20,979 per Acre

    Last Sold Summary

    • 61% Below List Price
    • 707 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    3501 George Washington Hwy, Oakland, MD 21550
  • /37

    $120,000

    Sold Dec 04, 2025

    204 E St, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 1975

    Last Sold Summary

    • $58/SF
    • 1 Day On Market

    Current Estimated Value $125,461

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
  • /64

    $1,010,000

    Sold Jan 09, 2026

    635 Biltmore Ridge Trail, Mc Henry, MD 21541

    • 5 Beds
    • 5 Baths
    • 4,437 Sq Ft
    • Built 2024

    Last Sold Summary

    • $228/SF
    • 91 Days On Market

    Current Estimated Value $1,098,170

    Last Listing Agent Edward Bass EXP Realty, LLC

    635 Biltmore Ridge Trail, Mc Henry, MD 21541
  • /78

    $689,000

    Sold Jun 26, 2026

    276 Sundance Way, Mc Henry, MD 21541

    • 3 Beds
    • 3.5 Baths
    • 2,670 Sq Ft
    • Built 2018

    Last Sold Summary

    • $258/SF
    • 61 Days On Market

    Current Estimated Value $682,601

    Last Listing Agent Kelsey Meyers Railey Realty, Inc.

    276 Sundance Way, Mc Henry, MD 21541
  • /11

    $375,000

    Sold Apr 30, 2026

    2173 King Wildesen Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • Built 2025

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $375,281

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

    2173 King Wildesen Rd, Oakland, MD 21550
  • /47

    $260,000

    Sold Feb 27, 2026

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Built 1972

    Last Sold Summary

    • $473/SF
    • 234 Days On Market

    Current Estimated Value $269,069

    Last Listing Agent Charlotte Savoy The KW Collective

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • /107

    $1,350,000

    Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,540,945

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
  • /61

    $820,000

    Sold Sep 02, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1990

    Last Sold Summary

    • 18 Days On Market

    Current Estimated Value $882,370

    Last Listing Agent Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    939 Glendale Rd, Oakland, MD 21550
  • /100

    $1,860,000

    Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Current Estimated Value $1,975,176

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
  • /2

    $699,000

    Sold Jul 31, 2026

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $191/SF
    • 38 Days On Market

    Current Estimated Value $737,877

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

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • /46

    $660,000

    Sold Aug 22, 2025

    181 Grand Estates Dr, Mc Henry, MD 21541

    • 4 Beds
    • 2.5 Baths
    • 2,640 Sq Ft
    • Built 2018

    Last Sold Summary

    • $250/SF
    • 56 Days On Market

    Current Estimated Value $697,149

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

    181 Grand Estates Dr, Mc Henry, MD 21541
  • /56

    $157,000

    Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $161,213

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
  • /39

    $1,065,000

    Sold Jun 18, 2026

    588 Lake Forest Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $755/SF
    • 6 Days On Market

    Current Estimated Value $1,099,140

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    588 Lake Forest Dr, Oakland, MD 21550
  • /51

    $425,000

    Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Current Estimated Value $439,576

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
  • /17

    $118,800

    Sold Jun 16, 2026

    1995 Bethlehem Rd, Oakland, MD 21550

    • Land
    • 7.33 Acres
    • $16,207 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    1995 Bethlehem Rd, Oakland, MD 21550
  • /20

    $150,000

    Sold Jul 01, 2026

    3395 Fingerboard Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • Built 2025

    Last Sold Summary

    • 25% Below List Price
    • 146 Days On Market

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

    3395 Fingerboard Rd, Oakland, MD 21550
  • /10

    $55,000

    Sold May 25, 2026

    114 C St, Oakland, MD 21550

    • 768 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Below List Price
    • $72/SF
    • 60 Days On Market

    Current Estimated Value $55,500

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

    114 C St, Oakland, MD 21550
  • /37

    $365,900

    Sold Mar 23, 2026

    17979 Garrett Hwy, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $381/SF
    • 9 Days On Market

    Current Estimated Value $378,673

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    17979 Garrett Hwy, Oakland, MD 21550
  • /86

    $1,100,000

    Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,219,101

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

    216 Tarn Dr, Oakland, MD 21550
  • /38

    $265,000

    Sold Dec 30, 2025

    968 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2012

    Last Sold Summary

    • $148/SF
    • 25 Days On Market

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

    968 Hutton Rd, Oakland, MD 21550
  • /50

    $1,200,000

    Sold Jun 30, 2026

    209 Black Angus Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft
    • Built 1991

    Last Sold Summary

    • $1,038/SF
    • 0 Days On Market

    Current Estimated Value $1,175,618

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    209 Black Angus Dr, Oakland, MD 21550
  • /18

    $3,500

    Sold Jun 24, 2026

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    • Land
    • 20,473 Sq Ft
    • $7,447 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 107 Days On Market

    Last Listing Agent Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    Lot 36 Fox Tail Rd, Oakland, MD 21550

Showing Results 121 - 160, Page 4 of 8

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