300

Recently Sold Homes in 21550

Section Image
  • /32

    $1,699,900

    Sold May 23, 2025

    2353 Boy Scout Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft
    • Built 1940

    Last Sold Summary

    • $549/SF
    • 6 Days On Market

    Current Estimated Value $1,787,846

    Last Listing Agent Jon Bell Railey Realty, Inc.

    2353 Boy Scout Rd, Oakland, MD 21550
  • /97

    $985,000

    Sold Nov 10, 2025

    360 Biltmore View, McHenry, MD 21541

    • 5 Beds
    • 3.5 Baths
    • 3,756 Sq Ft
    • Built 2017

    Last Sold Summary

    • $262/SF
    • 173 Days On Market

    Current Estimated Value $954,488

    Last Listing Agent Justin Liller Railey Realty, Inc.

    360 Biltmore View, McHenry, MD 21541
  • /25

    $42,000

    Sold Aug 06, 2025

    Lot 18 Moss Creek Cir, Oakland, MD 21550

    • Land
    • 3.61 Acres
    • $11,634 per Acre

    Last Sold Summary

    • 58 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 18 Moss Creek Cir, Oakland, MD 21550
  • /53

    $1,055,000

    Sold Jun 30, 2025

    193 Greenbrier Dr, McHenry, MD 21541

    • 6 Beds
    • 5.5 Baths
    • 5,712 Sq Ft
    • Built 2019

    Last Sold Summary

    • $185/SF
    • 7 Days On Market

    Current Estimated Value $1,011,411

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    193 Greenbrier Dr, McHenry, MD 21541
  • /65

    $280,500

    Sold Sep 12, 2025

    290 Crellin Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • Built 1982

    Last Sold Summary

    • $127/SF
    • 96 Days On Market

    Current Estimated Value $289,001

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
  • /41

    $239,900

    Sold Sep 12, 2025

    502 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1956

    Last Sold Summary

    • $143/SF
    • 17 Days On Market

    Current Estimated Value $246,839

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, Oakland, MD 21550
  • /97

    $732,500

    Sold Jun 09, 2025

    116 Wanderer Ln Unit F5, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1975

    Last Sold Summary

    • $509/SF
    • 6 Days On Market

    Current Estimated Value $715,905

    Last Listing Agent Charlene Deremer Coldwell Banker Home Town Realty

    116 Wanderer Ln Unit F5, Oakland, MD 21550
  • /53

    $495,000

    Sold Oct 08, 2025

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft
    • Built 2004

    Last Sold Summary

    • $204/SF
    • 106 Days On Market

    Current Estimated Value $495,763

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

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
  • /65

    $375,000

    Sold Jul 29, 2025

    5154 Maryland Hwy, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft
    • Built 1980

    Last Sold Summary

    • $131/SF
    • 23 Days On Market

    Current Estimated Value $399,383

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

    5154 Maryland Hwy, Oakland, MD 21550
  • /67

    $760,000

    Sold Nov 14, 2025

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1993

    Last Sold Summary

    • $317/SF
    • 113 Days On Market

    Current Estimated Value $791,821

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
  • /63

    $920,000

    Sold Aug 22, 2025

    254 Middleton Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • $383/SF
    • 19 Days On Market

    Current Estimated Value $955,607

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
  • /33

    $150,000

    Sold Dec 17, 2025

    111 Knoll Crest Heights Dr, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 3,504 Sq Ft
    • Built 1971

    Last Sold Summary

    • $43/SF
    • 48 Days On Market

    Current Estimated Value $162,264

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

    111 Knoll Crest Heights Dr, Oakland, MD 21550
  • /43

    $460,000

    Sold Oct 24, 2025

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • Built 2009

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $470,941

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
  • /32

    $139,000

    Sold Aug 15, 2025

    4960 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1971

    Last Sold Summary

    • $129/SF
    • 205 Days On Market

    Current Estimated Value $142,008

    Last Listing Agent Justin Liller Railey Realty, Inc.

    4960 Hutton Rd, Oakland, MD 21550
  • /72

    $310,000

    Sold Jun 18, 2025

    202 Deerfield Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,720 Sq Ft
    • Built 1987

    Last Sold Summary

    • $114/SF
    • 128 Days On Market

    Current Estimated Value $342,315

    Last Listing Agent Sharon Murray Coldwell Banker Home Town Realty

    202 Deerfield Dr, Oakland, MD 21550
  • /108

    $370,000

    Sold Oct 10, 2025

    220 N 11th St, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 3,159 Sq Ft
    • Built 1972

    Last Sold Summary

    • $117/SF
    • 12 Days On Market

    Current Estimated Value $382,941

    Last Listing Agent Justin Liller Railey Realty, Inc.

    220 N 11th St, Oakland, MD 21550
  • /45

    $435,000

    Sold Jul 02, 2025

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,838 Sq Ft
    • Built 2004

    Last Sold Summary

    • $237/SF
    • 626 Days On Market

    Current Estimated Value $431,927

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

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
  • /37

    $199,000

    Sold Feb 25, 2026

    1108 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1989

    Last Sold Summary

    • $207/SF
    • 3 Days On Market

    Current Estimated Value $198,501

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1108 Hutton Rd, Oakland, MD 21550
  • /40

    $311,500

    Sold Aug 22, 2025

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft
    • Built 1997

    Last Sold Summary

    • $389/SF
    • 167 Days On Market

    Current Estimated Value $312,048

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

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550
  • /68

    $1,400,000

    Sold Jan 30, 2026

    3067 Shingle Camp Rd, Mc Henry, MD 21541

    • 5 Beds
    • 4 Baths
    • 3,300 Sq Ft
    • Built 1999

    Last Sold Summary

    • $424/SF
    • 149 Days On Market

    Current Estimated Value $1,401,656

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

    3067 Shingle Camp Rd, Mc Henry, MD 21541
  • /79

    $925,000

    Sold Oct 07, 2025

    1473 Pergin Farm Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 1945

    Last Sold Summary

    • $415/SF
    • 93 Days On Market

    Current Estimated Value $1,509,015

    Last Listing Agent Tony Migliaccio Long & Foster Real Estate, Inc.

    1473 Pergin Farm Rd, Oakland, MD 21550
  • /73

    $285,000

    Sold Oct 06, 2025

    122 Earl Hauser Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2012

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Current Estimated Value $291,132

    Last Listing Agent Rich Orr Railey Realty, Inc.

    122 Earl Hauser Rd, Oakland, MD 21550
  • /27

    $712,500

    Sold Dec 30, 2025

    939 Glendale Rd Unit 19, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1994

    Last Sold Summary

    • $498/SF
    • 91 Days On Market

    Last Listing Agent Rick Davis Richard A. Davis & Associates

    939 Glendale Rd Unit 19, Oakland, MD 21550
  • /26

    $1,275,000

    Sold Jun 02, 2025

    464 Lake Forest Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,496 Sq Ft
    • Built 1997

    Last Sold Summary

    • $511/SF
    • 277 Days On Market

    Current Estimated Value $1,349,065

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

    464 Lake Forest Dr, Oakland, MD 21550
  • /9

    $145,000

    Sold Jul 03, 2025

    30 Snowshoe Ct, McHenry, MD 21541

    • Land
    • 15,681 Sq Ft
    • $402,778 per Acre

    Last Sold Summary

    • 53 Days On Market

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    30 Snowshoe Ct, McHenry, MD 21541
  • /8

    $79,900

    Sold Apr 03, 2026

    Lot 2 Pergin Farm Rd, Oakland, MD 21550

    • Land
    • 3.67 Acres
    • $21,771 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot 2 Pergin Farm Rd, Oakland, MD 21550
  • /92

    $635,000

    Sold Sep 26, 2025

    5 Arrowhead Ln, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Built 1988

    Last Sold Summary

    • $385/SF
    • 116 Days On Market

    Current Estimated Value $647,578

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    5 Arrowhead Ln, Oakland, MD 21550
  • /2

    $280,000

    Sold Feb 23, 2026

    1359 Cedar Ln, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Above List Price
    • $194/SF
    • 8 Days On Market

    Current Estimated Value $288,773

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

    1359 Cedar Ln, Oakland, MD 21550
  • /40

    $171,000

    Sold May 30, 2025

    5459 Hutton Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1940

    Last Sold Summary

    • $86/SF
    • 113 Days On Market

    Current Estimated Value $172,585

    Last Listing Agent Debra Beitzel Long & Foster Real Estate, Inc.

    5459 Hutton Rd, Oakland, MD 21550
  • /62

    $237,000

    Sold Jun 13, 2025

    13903 Garrett Hwy, Oakland, MD 21550

    • 1 Bed
    • 3 Baths
    • 1,536 Sq Ft
    • Built 1977

    Last Sold Summary

    • $154/SF
    • 15 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    13903 Garrett Hwy, Oakland, MD 21550
  • /12

    $154,900

    Sold Aug 25, 2025

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550

    • Land
    • 26,136 Sq Ft
    • $258,167 per Acre

    Last Sold Summary

    • 17 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550
  • /71

    $899,900

    Sold Jun 26, 2025

    145 Lower Penn Point Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,106 Sq Ft
    • Built 2007

    Last Sold Summary

    • $427/SF
    • 135 Days On Market

    Current Estimated Value $935,208

    Last Listing Agent Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, Oakland, MD 21550
  • /58

    $1,425,000

    Sold Oct 28, 2025

    20676 Garrett Hwy, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,280 Sq Ft
    • Built 2015

    Last Sold Summary

    • $625/SF
    • 17 Days On Market

    Current Estimated Value $1,432,347

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    20676 Garrett Hwy, Oakland, MD 21550
  • /35

    $285,000

    Sold Jul 03, 2025

    506 Cedar Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1979

    Last Sold Summary

    • $212/SF
    • 16 Days On Market

    Current Estimated Value $284,230

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

    506 Cedar Ln, Oakland, MD 21550
  • /28

    $339,000

    Sold Aug 01, 2025

    20160 Garrett Hwy Unit H712, Oakland, MD 21550

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

    Last Sold Summary

    • $753/SF
    • 124 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    20160 Garrett Hwy Unit H712, Oakland, MD 21550
  • /4

    $3,000

    Sold Oct 24, 2025

    Lot 27 Stool Rock Rd, Oakland, MD 21550

    • Land
    • 22,215 Sq Ft
    • $5,882 per Acre

    Last Sold Summary

    • 67 Days On Market

    Last Listing Agent Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    Lot 27 Stool Rock Rd, Oakland, MD 21550
  • /113

    $900,000

    Sold Nov 14, 2025

    102 Mountainview Ct, Oakland, MD 21550

    • 7 Beds
    • 4.5 Baths
    • 5,376 Sq Ft
    • Built 2010

    Last Sold Summary

    • $167/SF
    • 139 Days On Market

    Current Estimated Value $978,594

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    102 Mountainview Ct, Oakland, MD 21550
  • /32

    $255,000

    Sold Apr 13, 2026

    6485 Oakland Sang Run Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft
    • Built 1966

    Last Sold Summary

    • 7% Below List Price
    • $218/SF
    • 6 Days On Market

    Current Estimated Value $273,767

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

    6485 Oakland Sang Run Rd, Oakland, MD 21550
  • /51

    $180,000

    Sold Mar 20, 2026

    565 Glendale Rd Unit 204B, Oakland, MD 21550

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

    Last Sold Summary

    • $391/SF
    • 83 Days On Market

    Last Listing Agent Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 204B, Oakland, MD 21550
  • /67

    $790,000

    Sold Apr 24, 2026

    116 Chimney Rock Ln, McHenry, MD 21541

    • 5 Beds
    • 4.5 Baths
    • 2,964 Sq Ft
    • Built 2025

    Last Sold Summary

    • $267/SF
    • 246 Days On Market

    Current Estimated Value $794,423

    Last Listing Agent Jon Bell Railey Realty, Inc.

    116 Chimney Rock Ln, McHenry, MD 21541

Showing Results 41 - 80, Page 2 of 8

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