313

Recently Sold Homes in 21550

Section Image
  • /86

    $1,825,000 Sold Feb 13, 2026

    16 Grand Estates Dr, McHenry, MD 21541

    • 7 Beds
    • 7 Baths
    • 4,758 Sq Ft
    • Built 2025

    Last Sold Summary

    • $384/SF
    • 138 Days On Market

    Current Estimated Value $1,793,528

    Last Listing Agent Jon Bell Railey Realty, Inc.

    16 Grand Estates Dr, McHenry, MD 21541
  • /52

    $585,000 Sold Mar 31, 2026

    65 Village Dr Unit 6, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,740 Sq Ft
    • Built 2006

    Last Sold Summary

    • $336/SF
    • 390 Days On Market

    Current Estimated Value $608,132

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

    65 Village Dr Unit 6, Oakland, MD 21550
  • /50

    $739,000 Sold Oct 17, 2025

    425 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,586 Sq Ft
    • Built 1998

    Last Sold Summary

    • $466/SF
    • 32 Days On Market

    Current Estimated Value $748,303

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

    425 Mountainview Dr, Oakland, MD 21550
  • /25

    $130,000 Sold Dec 30, 2025

    Lot 32 Snowshoe Ct, Mc Henry, MD 21541

    • Land
    • 0.4 Acre
    • $325,000 per Acre

    Last Sold Summary

    • 281 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    Lot 32 Snowshoe Ct, Mc Henry, MD 21541
  • /80

    $1,270,000 Sold Oct 16, 2025

    3273 Lake Shore Dr, Oakland, MD 21550

    • 6 Beds
    • 3 Baths
    • 1,714 Sq Ft
    • Built 1930

    Last Sold Summary

    • $741/SF
    • 6 Days On Market

    Current Estimated Value $1,283,038

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    3273 Lake Shore Dr, Oakland, MD 21550
  • /2

    $3,500 Sold Feb 13, 2026

    Lot 25 W Big Piney Dr, Oakland, MD 21550

    • Land
    • 0.46 Acre
    • $7,609 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 271 Days On Market

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

    Lot 25 W Big Piney Dr, Oakland, MD 21550
  • /93

    $3,000,000 Sold Dec 02, 2025

    1931 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft
    • Built 2009

    Last Sold Summary

    • $588/SF
    • 430 Days On Market

    Current Estimated Value $3,008,434

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • /72

    $975,000 Sold Sep 25, 2025

    267 Woodlands Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft
    • Built 2021

    Last Sold Summary

    • $437/SF
    • 136 Days On Market

    Current Estimated Value $1,018,371

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

    267 Woodlands Hill Ln, Oakland, MD 21550
  • /127

    $2,550,000 Sold Aug 01, 2025

    1100 S Blakeslee Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 6,572 Sq Ft
    • Built 1998

    Last Sold Summary

    • $388/SF
    • 0 Days On Market

    Current Estimated Value $2,566,586

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    1100 S Blakeslee Rd, Oakland, MD 21550
  • /73

    $530,000 Sold Oct 03, 2025

    346 Skippers Point Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1976

    Last Sold Summary

    • $294/SF
    • 50 Days On Market

    Current Estimated Value $540,882

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, Oakland, MD 21550
  • /53

    $1,300,000 Sold Apr 30, 2025

    735 Winston Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,076 Sq Ft
    • Built 1985

    Last Sold Summary

    • $626/SF
    • 10 Days On Market

    Current Estimated Value $148,000

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

    735 Winston Rd, Oakland, MD 21550
  • /82

    $554,999 Sold Oct 03, 2025

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2007

    Last Sold Summary

    • $168/SF
    • 164 Days On Market

    Current Estimated Value $561,585

    Last Listing Agent Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
  • /12

    $380,000 Sold May 30, 2025

    Lot 76 S Blakeslee Rd, Oakland, MD 21550

    • Land
    • 1.06 Acres
    • $358,491 per Acre

    Last Sold Summary

    • 4 Days On Market

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

    Lot 76 S Blakeslee Rd, Oakland, MD 21550
  • /72

    $835,000 Sold Mar 27, 2026

    139 Overlook Ridge Dr, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,846 Sq Ft
    • Built 2004

    Last Sold Summary

    • $293/SF
    • 340 Days On Market

    Current Estimated Value $824,096

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

    139 Overlook Ridge Dr, Oakland, MD 21550
  • /58

    $249,000 Sold Mar 20, 2026

    711 Heritage Dr, Oakland, MD 21550

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

    Last Sold Summary

    • $178/SF
    • 6 Days On Market

    Current Estimated Value $247,970

    Last Listing Agent Rich Orr Railey Realty, Inc.

    711 Heritage Dr, Oakland, MD 21550
  • /60

    $280,000 Sold Nov 14, 2025

    1056 Sunrise Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,528 Sq Ft
    • Built 1976

    Last Sold Summary

    • $183/SF
    • 59 Days On Market

    Current Estimated Value $273,005

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

    1056 Sunrise Dr, Oakland, MD 21550
  • /5

    $135,000 Sold Jun 25, 2025

    Lot #5 Swan Meadow Dr, Oakland, MD 21550

    • Land
    • 10 Acres
    • $13,500 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot #5 Swan Meadow Dr, Oakland, MD 21550
  • /149

    $2,975,000 Sold Oct 03, 2025

    1087 Pergin Farm Rd, Oakland, MD 21550

    • 6 Beds
    • 5.5 Baths
    • 4,481 Sq Ft
    • Built 1984

    Last Sold Summary

    • $664/SF
    • 16 Days On Market

    Current Estimated Value $2,970,747

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
  • /23

    $18,000 Sold Jul 03, 2025

    Lot 9 Birchwood Dr, Oakland, MD 21550

    • Land
    • 0.8 Acre
    • $22,500 per Acre

    Last Sold Summary

    • 5 Days On Market

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

    Lot 9 Birchwood Dr, Oakland, MD 21550
  • /35

    $390,000 Sold Dec 12, 2025

    30 Village Dr Unit 3, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 916 Sq Ft
    • Built 2005

    Last Sold Summary

    • $426/SF
    • 34 Days On Market

    Current Estimated Value $394,914

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    30 Village Dr Unit 3, Oakland, MD 21550
  • /63

    $699,900 Sold Sep 26, 2025

    130 Wisp Adventure Rd, McHenry, MD 21541

    • 5 Beds
    • 4 Baths
    • 3,105 Sq Ft
    • Built 2021

    Last Sold Summary

    • $225/SF
    • 76 Days On Market

    Current Estimated Value $708,786

    Last Listing Agent Jon Bell Railey Realty, Inc.

    130 Wisp Adventure Rd, McHenry, MD 21541
  • /45

    $195,000 Sold Jul 11, 2025

    422 Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1972

    Last Sold Summary

    • $203/SF
    • 17 Days On Market

    Current Estimated Value $193,804

    Last Listing Agent Larry Smith Railey Realty, Inc.

    422 Underwood Rd, Oakland, MD 21550
  • /2

    $285,000 Sold Sep 05, 2025

    2360 Garrett Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 0 Days On Market

    Current Estimated Value $291,050

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    2360 Garrett Rd, Oakland, MD 21550
  • /86

    $770,000 Sold Sep 15, 2025

    722 Winding Estates Dr, Mc Henry, MD 21541

    • 4 Beds
    • 2.5 Baths
    • 2,962 Sq Ft
    • Built 2017

    Last Sold Summary

    • $260/SF
    • 380 Days On Market

    Current Estimated Value $775,465

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

    722 Winding Estates Dr, Mc Henry, MD 21541
  • /47

    $208,550 Sold Sep 26, 2025

    2805 Shady Dell Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1966

    Last Sold Summary

    • $143/SF
    • 42 Days On Market

    Current Estimated Value $217,414

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    2805 Shady Dell Rd, Oakland, MD 21550
  • /111

    $2,600,000 Sold Oct 20, 2025

    197 Black Angus Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,156 Sq Ft
    • Built 1975

    Last Sold Summary

    • $626/SF
    • 15 Days On Market

    Current Estimated Value $2,575,127

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, Oakland, MD 21550
  • /81

    $1,200,000 Sold Jan 16, 2026

    19956 Garrett Hwy Unit 6, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • Built 2007

    Last Sold Summary

    • $400/SF
    • 162 Days On Market

    Current Estimated Value $1,181,855

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
  • /22

    $212,000 Sold Dec 05, 2025

    4 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 166 Days On Market

    Current Estimated Value $214,066

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    4 Laurel Brook Dr, Oakland, MD 21550
  • /74

    $2,450,000 Sold Oct 30, 2025

    273 Glendale Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,141 Sq Ft
    • Built 2008

    Last Sold Summary

    • $477/SF
    • 7 Days On Market

    Current Estimated Value $2,478,468

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

    273 Glendale Rd, Oakland, MD 21550
  • /66

    $499,000 Sold Jul 15, 2025

    101 Sunset Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 3,024 Sq Ft
    • Built 1987

    Last Sold Summary

    • $165/SF
    • 11 Days On Market

    Current Estimated Value $474,033

    Last Listing Agent Rich Orr Railey Realty, Inc.

    101 Sunset Dr, Oakland, MD 21550
  • /24

    $17,000 Sold Aug 22, 2025

    Lot 31 Fawn Dr, Oakland, MD 21550

    • Land
    • 0.69 Acre
    • $24,638 per Acre

    Last Sold Summary

    • 19 Days On Market

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

    Lot 31 Fawn Dr, Oakland, MD 21550
  • /4

    $115,000 Sold Sep 26, 2025

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550

    • Land
    • 0.52 Acre
    • $221,154 per Acre

    Last Sold Summary

    • 32 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
  • /28

    $174,500 Sold Oct 30, 2025

    170 Tannery Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • Built 1974

    Last Sold Summary

    • $94/SF
    • 96 Days On Market

    Current Estimated Value $180,402

    Last Listing Agent Jonathan Minerick Homecoin.com

    170 Tannery Rd, Oakland, MD 21550
  • /85

    $975,000 Sold Nov 24, 2025

    202 Penelacre Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • Built 1985

    Last Sold Summary

    • $592/SF
    • 12 Days On Market

    Current Estimated Value $999,428

    Last Listing Agent Justin Liller Railey Realty, Inc.

    202 Penelacre Ln, Oakland, MD 21550
  • /10

    $30,000 Sold Apr 21, 2025

    5 Warnick Way, Oakland, MD 21550

    • Land
    • 0.84 Acre
    • $35,714 per Acre

    Last Sold Summary

    • 590 Days On Market

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    5 Warnick Way, Oakland, MD 21550
  • /93

    $3,375,000 Sold Nov 13, 2025

    870 Holy Cross Dr, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 5,681 Sq Ft
    • Built 2007

    Last Sold Summary

    • $594/SF
    • 5 Days On Market

    Current Estimated Value $3,226,564

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    870 Holy Cross Dr, Oakland, MD 21550
  • /74

    $690,000 Sold Oct 15, 2025

    41 Sandstone Cir, Mc Henry, MD 21541

    • 4 Beds
    • 3 Baths
    • 1,716 Sq Ft
    • Built 2021

    Last Sold Summary

    • $402/SF
    • 340 Days On Market

    Current Estimated Value $691,778

    Last Listing Agent Justin Liller Railey Realty, Inc.

    41 Sandstone Cir, Mc Henry, MD 21541
  • /48

    $285,000 Sold Feb 19, 2026

    143 Manor Dr, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,786 Sq Ft
    • Built 1977

    Last Sold Summary

    • 5% Below List Price
    • $160/SF
    • 2 Days On Market

    Current Estimated Value $289,194

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    143 Manor Dr, Oakland, MD 21550
  • /55

    $280,000 Sold Jul 31, 2025

    4012 Maryland Hwy, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,824 Sq Ft
    • Built 1968

    Last Sold Summary

    • $154/SF
    • 32 Days On Market

    Current Estimated Value $275,869

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    4012 Maryland Hwy, Oakland, MD 21550
  • /56

    $775,000 Sold Nov 20, 2025

    161 Kendall Camp Cir, McHenry, MD 21541

    • 4 Beds
    • 3 Baths
    • 2,135 Sq Ft
    • Built 2006

    Last Sold Summary

    • $363/SF
    • 209 Days On Market

    Current Estimated Value $754,288

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    161 Kendall Camp Cir, McHenry, MD 21541

Showing Results 241 - 280, Page 7 of 8

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