319

Recently Sold Homes in 21550

Section Image
  • /56

    $320,000

    Sold Nov 05, 2025

    531 S 3rd St, Oakland, MD 21550

    • 5 Beds
    • 2.5 Baths
    • 2,477 Sq Ft
    • Built 1920

    Last Sold Summary

    • $129/SF
    • 118 Days On Market

    Current Estimated Value $333,964

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
  • /52

    $840,000

    Sold Jan 31, 2026

    35 Blue Mountain View, McHenry, MD 21541

    • 5 Beds
    • 4.5 Baths
    • 2,832 Sq Ft
    • Built 2022

    Last Sold Summary

    • 16% Below List Price
    • $297/SF
    • 221 Days On Market

    Current Estimated Value $874,205

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    35 Blue Mountain View, McHenry, MD 21541
  • /26

    $110,000

    Sold Jul 07, 2026

    Lot 47 Mountaintop Rd, McHenry, MD 21550

    • Land
    • 24,829 Sq Ft
    • $192,982 per Acre

    Last Sold Summary

    • 359 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    Lot 47 Mountaintop Rd, McHenry, MD 21550
  • /71

    $590,000

    Sold Jan 16, 2026

    3084 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft
    • Built 1999

    Last Sold Summary

    • $239/SF
    • 305 Days On Market

    Current Estimated Value $653,128

    Last Listing Agent Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
  • /30

    $17,000

    Sold May 28, 2026

    Lots 37 & 38 Fir Tree Dr, Oakland, MD 21550

    • Land
    • 1.58 Acres
    • $10,759 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 12 Days On Market

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

    Lots 37 & 38 Fir Tree Dr, Oakland, MD 21550
  • /80

    $893,000

    Sold Aug 05, 2026

    208 Cliff Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,219 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $402/SF
    • 15 Days On Market

    Current Estimated Value $946,554

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    208 Cliff Dr, 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 $316,557

    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 $1,651,160

    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
  • /73

    $1,800,000

    Sold Jun 12, 2026

    62 Duck Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 4,150 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $434/SF
    • 13 Days On Market

    Current Estimated Value $1,795,605

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

    62 Duck Cove 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 $1,556,815

    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 $682,243

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
  • /28

    $335,000

    Sold Jul 07, 2026

    1740 Old Crellin Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1987

    Last Sold Summary

    • $146/SF
    • 28 Days On Market

    Current Estimated Value $326,949

    Last Listing Agent Andrew Orr The KW Collective

    1740 Old Crellin Rd, 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 $727,423

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
  • /53

    $245,000

    Sold Jul 17, 2026

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • Built 2006

    Last Sold Summary

    • 228 Days On Market

    Last Listing Agent Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, 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 $299,155

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

    215 N 10th St, Oakland, MD 21550
  • /2

    $205,000

    Sold May 20, 2026

    207 Shenandoah Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Above List Price
    • $137/SF
    • 6 Days On Market

    Current Estimated Value $195,138

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

    207 Shenandoah Ave, 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 $947,374

    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 $574,608

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
  • /7

    $14,000

    Sold Jul 24, 2026

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550

    • Land
    • 40,075 Sq Ft
    • $15,217 per Acre

    Last Sold Summary

    • 53% Below List Price
    • 73 Days On Market

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

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550
  • /82

    $815,000

    Sold Jun 26, 2026

    891 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 3,990 Sq Ft
    • Built 2002

    Last Sold Summary

    • 7% Below List Price
    • $204/SF
    • 46 Days On Market

    Current Estimated Value $858,036

    Last Listing Agent Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, 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 $1,436,140

    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
  • /10

    $300,000

    Sold May 06, 2026

    4000 Area Broadford Rd, Oakland, MD 21550

    • Land
    • 56.5 Acres
    • $5,310 per Acre

    Last Sold Summary

    • 0 Days On Market

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

    4000 Area Broadford Rd, Oakland, MD 21550
  • /43

    $290,000

    Sold Jun 01, 2026

    3749 Maryland Hwy, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,015 Sq Ft
    • Built 1982

    Last Sold Summary

    • 11% Below List Price
    • $144/SF
    • 63 Days On Market

    Current Estimated Value $284,862

    Last Listing Agent Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, Oakland, MD 21550
  • /36

    $829,000

    Sold May 22, 2026

    34 Hooppole Ct, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • Built 1975

    Last Sold Summary

    • $612/SF
    • 0 Days On Market

    Current Estimated Value $802,749

    Last Listing Agent Rich Orr Railey Realty, Inc.

    34 Hooppole Ct, 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 $138,149

    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 $685,523

    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
  • /52

    $508,000

    Sold Jun 18, 2026

    247 Sloan Tract Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Above List Price
    • $392/SF
    • 2 Days On Market

    Current Estimated Value $500,501

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    247 Sloan Tract Rd, Oakland, MD 21550
  • /59

    $815,000

    Sold Aug 10, 2026

    39 Leo Friend Rd, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft
    • Built 2003

    Last Sold Summary

    • 7% Below List Price
    • $209/SF
    • 27 Days On Market

    Current Estimated Value $866,878

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

    39 Leo Friend Rd, 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 $313,004

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    445 Dennett Rd, Oakland, MD 21550
  • /74

    $1,425,000

    Sold May 20, 2026

    2332 Paradise Point Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $690/SF
    • 2 Days On Market

    Current Estimated Value $1,368,102

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    2332 Paradise Point 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 $862,713

    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 $257,667

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
  • /24

    $38,000

    Sold Jul 02, 2026

    LOT 2 Oak Breeze Ln, Oakland, MD 21550

    • Land
    • 23,086 Sq Ft
    • $71,698 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 21 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    LOT 2 Oak Breeze Ln, 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 $509,332

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

Showing Results 201 - 240, Page 6 of 8

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