300

Recently Sold Homes in 21550

Section Image
  • /66

    $490,000

    Sold Aug 08, 2025

    462 Skippers Point Rd, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1983

    Last Sold Summary

    • $302/SF
    • 51 Days On Market

    Current Estimated Value $537,834

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    462 Skippers Point Rd, Oakland, MD 21550
  • /44

    $225,000

    Sold Jul 18, 2025

    600 Hope Ave, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,480 Sq Ft
    • Built 1981

    Last Sold Summary

    • $91/SF
    • 21 Days On Market

    Current Estimated Value $234,711

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

    600 Hope Ave, Oakland, MD 21550
  • /35

    $285,000

    Sold Nov 13, 2025

    473 Cumberland Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $205/SF
    • 155 Days On Market

    Current Estimated Value $302,416

    Last Listing Agent Jeremy McDonough Mr. Lister Realty

    473 Cumberland Rd, Oakland, MD 21550
  • /13

    $67,500

    Sold Jan 07, 2026

    Lot 38 Winding Estates Dr, Mc Henry, MD 21550

    • Land
    • 1 Acre
    • $67,500 per Acre

    Last Sold Summary

    • 141 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    Lot 38 Winding Estates Dr, Mc Henry, MD 21550
  • /75

    $1,525,000

    Sold Sep 04, 2025

    1419 Sandy Shores Rd, Mc Henry, MD 21541

    • 5 Beds
    • 5 Baths
    • 3,696 Sq Ft
    • Built 1999

    Last Sold Summary

    • $413/SF
    • 125 Days On Market

    Current Estimated Value $1,549,415

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1419 Sandy Shores Rd, Mc Henry, MD 21541
  • /20

    $55,000

    Sold Nov 17, 2025

    19 Pheasant Run, Oakland, MD 21550

    • Land
    • 2.84 Acres
    • $19,366 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    19 Pheasant Run, Oakland, MD 21550
  • /18

    $160,000

    Sold Aug 28, 2025

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550

    • Land
    • 25 Acres
    • $6,400 per Acre

    Last Sold Summary

    • 44 Days On Market

    Last Listing Agent Ally Litten Mountainside Home Realty

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
  • /2

    $200,000

    Sold Feb 27, 2026

    0 Laurel Run Rd, Oakland, MD 21550

    • Land
    • 70 Acres
    • $2,857 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    0 Laurel Run Rd, Oakland, MD 21550
  • /53

    $1,500,000

    Sold Dec 01, 2025

    1674 Paradise Point Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 465 Days On Market

    Current Estimated Value $1,514,649

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
  • /64

    $695,000

    Sold Oct 09, 2025

    353 Basswood Way Unit 24, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 2005

    Last Sold Summary

    • $261/SF
    • 14 Days On Market

    Current Estimated Value $686,768

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
  • /61

    $650,000

    Sold Aug 21, 2025

    1006 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1993

    Last Sold Summary

    • $336/SF
    • 27 Days On Market

    Current Estimated Value $708,350

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
  • /48

    $279,000

    Sold Sep 25, 2025

    215 N 10th St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,518 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Below List Price
    • $184/SF
    • 6 Days On Market

    Current Estimated Value $292,385

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    215 N 10th St, Oakland, MD 21550
  • /22

    $25,000

    Sold Jun 27, 2025

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

    • Land
    • 1.05 Acres
    • $23,810 per Acre

    Last Sold Summary

    • 84 Days On Market

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

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
  • /40

    $615,000

    Sold Jul 07, 2025

    245 Santa fe Trail, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft
    • Built 2003

    Last Sold Summary

    • $270/SF
    • 51 Days On Market

    Current Estimated Value $625,109

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

    245 Santa fe Trail, Oakland, MD 21550
  • /79

    $910,000

    Sold Sep 25, 2025

    2045 Swallow Falls Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 5,416 Sq Ft
    • Built 2023

    Last Sold Summary

    • $168/SF
    • 82 Days On Market

    Current Estimated Value $930,371

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

    2045 Swallow Falls Rd, Oakland, MD 21550
  • /43

    $587,500

    Sold Aug 22, 2025

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2019

    Last Sold Summary

    • $178/SF
    • 9 Days On Market

    Current Estimated Value $579,961

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
  • /94

    $1,340,000

    Sold Apr 08, 2026

    336 Paradise Heights, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • $474/SF
    • 159 Days On Market

    Current Estimated Value $1,466,811

    Last Listing Agent Susan Bell Railey Realty, Inc.

    336 Paradise Heights, Oakland, MD 21550
  • /15

    $87,000

    Sold Feb 06, 2026

    Lot 69 Sundance Way, Mc Henry, MD 21541

    • Land
    • 30,056 Sq Ft
    • $126,087 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 588 Days On Market

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    Lot 69 Sundance Way, Mc Henry, MD 21541
  • /17

    $15,000

    Sold Jul 09, 2025

    815 L St, Oakland, MD 21550

    • Land
    • 12,196 Sq Ft
    • $53,571 per Acre

    Last Sold Summary

    • 1 Day On Market

    Current Estimated Value $91,333

    Last Listing Agent Lauren McCann Railey Realty, Inc.

    815 L St, Oakland, MD 21550
  • /39

    $134,000

    Sold Dec 12, 2025

    105 Main St, Deer Park, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,466 Sq Ft
    • Built 1880

    Last Sold Summary

    • $91/SF
    • 74 Days On Market

    Current Estimated Value $134,251

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

    105 Main St, Deer Park, MD 21550
  • /43

    $651,000

    Sold Oct 29, 2025

    68 Sundance Way, McHenry, MD 21541

    • 4 Beds
    • 3 Baths
    • 1,932 Sq Ft
    • Built 2023

    Last Sold Summary

    • $337/SF
    • 232 Days On Market

    Current Estimated Value $674,936

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

    68 Sundance Way, McHenry, MD 21541
  • /4

    $12,000

    Sold Sep 25, 2025

    0 E Reese St, Oakland, MD 21550

    • Land
    • 10,890 Sq Ft
    • $48,000 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Thomas Long Railey Realty, Inc.

    0 E Reese St, Oakland, MD 21550
  • /62

    $305,000

    Sold Nov 07, 2025

    445 Dennett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,410 Sq Ft
    • Built 1955

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Current Estimated Value $308,607

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    445 Dennett Rd, Oakland, MD 21550
  • /47

    $850,000

    Sold Apr 17, 2026

    130 Lodestone Way, Mc Henry, MD 21541

    • 4 Beds
    • 3 Baths
    • 2,512 Sq Ft
    • Built 2024

    Last Sold Summary

    • $338/SF
    • 270 Days On Market

    Current Estimated Value $858,674

    Last Listing Agent Charlotte Savoy The KW Collective

    130 Lodestone Way, Mc Henry, MD 21541
  • /61

    $275,000

    Sold Sep 05, 2025

    648 S 3rd St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1940

    Last Sold Summary

    • $185/SF
    • 3 Days On Market

    Current Estimated Value $284,667

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
  • /53

    $509,000

    Sold May 05, 2026

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $159/SF
    • 72 Days On Market

    Current Estimated Value $527,377

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • /52

    $365,000

    Sold Aug 12, 2025

    1220 Broadford Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft
    • Built 1971

    Last Sold Summary

    • $174/SF
    • 58 Days On Market

    Current Estimated Value $378,432

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1220 Broadford Rd, Oakland, MD 21550
  • /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 $1,807,324

    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 $583,030

    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 $742,265

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

    425 Mountainview Dr, Oakland, MD 21550
  • /25

    $130,000

    Sold Dec 30, 2025

    Lot 32 Snowshoe Ct, Mc Henry, MD 21541

    • Land
    • 17,424 Sq Ft
    • $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 $1,287,061

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

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

    $3,500

    Sold Feb 13, 2026

    Lot 25 W Big Piney Dr, Oakland, MD 21550

    • Land
    • 20,037 Sq Ft
    • $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 $3,023,969

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • /59

    $210,000

    Sold May 06, 2026

    313 W Liberty St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft
    • Built 1947

    Last Sold Summary

    • 5% Below List Price
    • $197/SF
    • 39 Days On Market

    Current Estimated Value $217,343

    Last Listing Agent Justin Liller Railey Realty, Inc.

    313 W Liberty St, 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 $1,018,676

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

    267 Woodlands Hill Ln, Oakland, MD 21550
  • /107

    $575,000

    Sold Apr 30, 2026

    621 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,242 Sq Ft
    • Built 1988

    Last Sold Summary

    • 25% Below List Price
    • $177/SF
    • 502 Days On Market

    Current Estimated Value $654,678

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

    621 Paradise Heights, 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 $2,693,188

    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 $565,781

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    346 Skippers Point 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 $558,473

    Last Listing Agent Jon Bell Railey Realty, Inc.

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

Showing Results 201 - 240, Page 6 of 8

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