300

Recently Sold Homes in 21550

Section Image
  • /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, LLC

    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 $845,884

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

    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 $247,527

    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 $275,253

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

    1056 Sunrise Dr, Oakland, MD 21550
  • /2

    $276,000

    Sold May 08, 2026

    226 N Hammond St, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Below List Price
    • $276/SF
    • 39 Days On Market

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

    226 N Hammond St, 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 $3,036,407

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
  • /60

    $260,000

    Sold May 08, 2026

    2571 Shady Dell Rd, Oakland, MD 21550

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

    Last Sold Summary

    • 3% Below List Price
    • $155/SF
    • 0 Days On Market

    Current Estimated Value $221,004

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

    2571 Shady Dell Rd, Oakland, MD 21550
  • /23

    $18,000

    Sold Jul 03, 2025

    Lot 9 Birchwood Dr, Oakland, MD 21550

    • Land
    • 34,848 Sq Ft
    • $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 $385,386

    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 $721,092

    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 $197,600

    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 $296,700

    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 $770,457

    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 $222,315

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

    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 $2,636,603

    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 $1,173,528

    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 $214,189

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

    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 $2,493,520

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

    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 $478,187

    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
    • 30,056 Sq Ft
    • $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
    • 22,651 Sq Ft
    • $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 $178,943

    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 $986,600

    Last Listing Agent Justin Liller Railey Realty, Inc.

    202 Penelacre Ln, 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 $3,409,867

    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 $689,447

    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 $288,465

    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 $284,137

    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 $764,166

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    161 Kendall Camp Cir, McHenry, MD 21541
  • /18

    $75,000

    Sold Sep 25, 2025

    4.00 Acres Moose Crossing, Oakland, MD 21550

    • Land
    • 4 Acres
    • $18,750 per Acre

    Last Sold Summary

    • 27 Days On Market

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

    4.00 Acres Moose Crossing, Oakland, MD 21550
  • /25

    $215,000

    Sold Mar 20, 2026

    41 Fox Den Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,569 Sq Ft
    • Built 1940

    Last Sold Summary

    • 19% Below List Price
    • $137/SF
    • 310 Days On Market

    Current Estimated Value $244,028

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

    41 Fox Den Rd, Oakland, MD 21550
  • /70

    $555,000

    Sold Nov 20, 2025

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 2009

    Last Sold Summary

    • $206/SF
    • 68 Days On Market

    Current Estimated Value $546,737

    Last Listing Agent Justin Liller Railey Realty, Inc.

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
  • /103

    $320,000

    Sold Jul 18, 2025

    206 N 10th St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,772 Sq Ft
    • Built 1972

    Last Sold Summary

    • $115/SF
    • 37 Days On Market

    Current Estimated Value $341,726

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    206 N 10th St, Oakland, MD 21550
  • /20

    $40,000

    Sold Oct 20, 2025

    111 Tarn Dr, Oakland, MD 21550

    • Land
    • 1 Acre
    • $40,000 per Acre

    Last Sold Summary

    • 260 Days On Market

    Current Estimated Value $969,419

    Last Listing Agent Amy Grubby AEK Real Estate, LLC

    111 Tarn Dr, Oakland, MD 21550
  • /70

    $802,500

    Sold Feb 18, 2026

    200 Kendall Camp Cir, McHenry, MD 21541

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

    Last Sold Summary

    • 6% Below List Price
    • $376/SF
    • 44 Days On Market

    Current Estimated Value $805,882

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    200 Kendall Camp Cir, McHenry, MD 21541
  • /79

    $735,000

    Sold Dec 18, 2025

    465 Pergin Farm Rd, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,960 Sq Ft
    • Built 2006

    Last Sold Summary

    • $248/SF
    • 9 Days On Market

    Current Estimated Value $735,894

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

    465 Pergin Farm Rd, Oakland, MD 21550
  • /4

    $61,125

    Sold Jun 25, 2025

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550

    • Land
    • 6.75 Acres
    • $9,056 per Acre

    Last Sold Summary

    Last Listing Agent Rich Orr Railey Realty, Inc.

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
  • /8

    $87,500

    Sold Mar 12, 2026

    54 Greenstone Way, Sang Run, MD 21541

    • Land
    • 23,522 Sq Ft
    • $162,037 per Acre

    Last Sold Summary

    • 50% Below List Price
    • 667 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    54 Greenstone Way, Sang Run, MD 21541
  • /43

    $110,000

    Sold Jul 16, 2025

    408 Shenandoah Ave, Oakland, MD 21550

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

    Last Sold Summary

    • $115/SF
    • 2 Days On Market

    Current Estimated Value $115,759

    Last Listing Agent Rich Orr Railey Realty, Inc.

    408 Shenandoah Ave, Oakland, MD 21550
  • /57

    $1,200,000

    Sold Jun 13, 2025

    19956 Garrett Hwy Unit 2, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,012 Sq Ft
    • Built 2007

    Last Sold Summary

    • $398/SF
    • 5 Days On Market

    Current Estimated Value $1,175,649

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

    19956 Garrett Hwy Unit 2, Oakland, MD 21550

Showing Results 241 - 280, Page 7 of 8

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