319

Recently Sold Homes in 21550

Section Image
  • /21

    $295,000

    Sold Dec 23, 2025

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft
    • Built 1997

    Last Sold Summary

    • $392/SF
    • 21 Days On Market

    Current Estimated Value $304,865

    Last Listing Agent James Matthews Taylor-Made Deep Creek Real Estate, LLC

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
  • /50

    $567,500

    Sold Mar 13, 2026

    189 Red Run Rd Unit 1C2, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $473/SF
    • 227 Days On Market

    Current Estimated Value $563,205

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

    189 Red Run Rd Unit 1C2, Oakland, MD 21550
  • /44

    $145,000

    Sold Jul 03, 2026

    1099 Table Rock Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 1,728 Sq Ft
    • Built 1940

    Last Sold Summary

    • $84/SF
    • 0 Days On Market

    Current Estimated Value $131,026

    Last Listing Agent Rich Orr Railey Realty, Inc.

    1099 Table Rock Rd, Oakland, MD 21550
  • /67

    $1,542,000

    Sold Nov 13, 2025

    1567 Pergin Farm Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft
    • Built 2002

    Last Sold Summary

    • $482/SF
    • 15 Days On Market

    Current Estimated Value $1,634,779

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, Oakland, MD 21550
  • /50

    $295,000

    Sold May 20, 2026

    163 Crestview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft
    • Built 1997

    Last Sold Summary

    • $208/SF
    • 275 Days On Market

    Current Estimated Value $287,402

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

    163 Crestview Dr, Oakland, MD 21550
  • /65

    $537,000

    Sold Feb 27, 2026

    77 Meadow Ct, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft
    • Built 2006

    Last Sold Summary

    • $220/SF
    • 100 Days On Market

    Current Estimated Value $595,222

    Last Listing Agent Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
  • /60

    $505,000

    Sold Nov 14, 2025

    36 Ridgewood Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft
    • Built 2000

    Last Sold Summary

    • $295/SF
    • 228 Days On Market

    Current Estimated Value $540,895

    Last Listing Agent Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
  • /24

    $85,000

    Sold Oct 03, 2025

    1101 Wheeling Ave, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft
    • Built 1950

    Last Sold Summary

    • $49/SF
    • 25 Days On Market

    Current Estimated Value $157,992

    Last Listing Agent Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
  • /13

    $60,000

    Sold Sep 24, 2025

    Lot 38 Fern Loop, Sang Run, MD 21541

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    Last Sold Summary

    • 607 Days On Market

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

    Lot 38 Fern Loop, Sang Run, MD 21541
  • /24

    $110,000

    Sold Sep 26, 2025

    110 W Pennington St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1946

    Last Sold Summary

    • $143/SF
    • 12 Days On Market

    Current Estimated Value $120,931

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

    110 W Pennington St, Oakland, MD 21550
  • /50

    $425,000

    Sold Jun 03, 2026

    609 Southern Pines Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $189/SF
    • 295 Days On Market

    Current Estimated Value $414,783

    Last Listing Agent Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, Oakland, MD 21550
  • /13

    $50,000

    Sold Feb 06, 2026

    72 Chimney Rock Ln, Mc Henry, MD 21541

    • Land
    • 24,829 Sq Ft
    • $87,719 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 2 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    72 Chimney Rock Ln, Mc Henry, MD 21541
  • /22

    $185,000

    Sold May 22, 2026

    1307 Broadford Rd, Oakland, MD 21550

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

    Last Sold Summary

    • 11% Below List Price
    • $195/SF
    • 46 Days On Market

    Current Estimated Value $190,466

    Last Listing Agent Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, Oakland, MD 21550
  • /48

    $229,000

    Sold Dec 15, 2025

    104 G St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • Built 1900

    Last Sold Summary

    • $142/SF
    • 26 Days On Market

    Current Estimated Value $230,979

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550
  • /22

    $38,000

    Sold Jun 16, 2026

    422 Maple Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1940

    Last Sold Summary

    • 37% Below List Price
    • $24/SF
    • 34 Days On Market

    Current Estimated Value $56,774

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    422 Maple Ave, Oakland, MD 21550
  • /20

    $195,000

    Sold Nov 12, 2025

    210 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft
    • Built 1996

    Last Sold Summary

    • $162/SF
    • 2 Days On Market

    Current Estimated Value $202,503

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
  • /38

    $780,000

    Sold Jul 02, 2026

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,929 Sq Ft
    • Built 1993

    Last Sold Summary

    • 2% Below List Price
    • $404/SF
    • 4 Days On Market

    Current Estimated Value $797,633

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
  • /71

    $950,000

    Sold Jul 29, 2026

    137 Paradise Gardens Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,730 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $348/SF
    • 76 Days On Market

    Current Estimated Value $1,006,592

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

    137 Paradise Gardens Rd, Oakland, MD 21550
  • /33

    $130,000

    Sold May 22, 2026

    565 Glendale Rd Unit 210-A, Oakland, MD 21550

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

    Last Sold Summary

    • 26% Below List Price
    • $340/SF
    • 225 Days On Market

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

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
  • /53

    $682,567

    Sold Oct 31, 2025

    183 Kendall Camp Cir, McHenry, MD 21541

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

    Last Sold Summary

    • $320/SF
    • 173 Days On Market

    Current Estimated Value $719,421

    Last Listing Agent Jon Bell Railey Realty, Inc.

    183 Kendall Camp Cir, McHenry, MD 21541
  • /22

    $180,000

    Sold Sep 12, 2025

    4643 Oakland Sang Run Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1979

    Last Sold Summary

    • $208/SF
    • 4 Days On Market

    Current Estimated Value $207,625

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
  • /45

    $750,000

    Sold Jan 16, 2026

    198 Grandview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft
    • Built 2003

    Last Sold Summary

    • $273/SF
    • 150 Days On Market

    Current Estimated Value $804,608

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
  • /60

    $1,325,000

    Sold Jun 26, 2026

    1475 Marsh Hill Rd, Mc Henry, MD 21541

    • 3 Beds
    • 3 Baths
    • 1,856 Sq Ft
    • Built 1978

    Last Sold Summary

    • 4% Below List Price
    • $714/SF
    • 2 Days On Market

    Current Estimated Value $1,303,534

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

    1475 Marsh Hill Rd, Mc Henry, MD 21541
  • /48

    $250,000

    Sold Jun 11, 2026

    18 Ollie North Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,956 Sq Ft
    • Built 1975

    Last Sold Summary

    • 13% Below List Price
    • $128/SF
    • 31 Days On Market

    Current Estimated Value $252,420

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    18 Ollie North Rd, Oakland, MD 21550
  • /65

    $558,000

    Sold Nov 10, 2025

    72 Cliff Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $256/SF
    • 32 Days On Market

    Current Estimated Value $579,048

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
  • /65

    $379,000

    Sold Oct 08, 2025

    113 G St, Oakland, MD 21550

    • 9 Beds
    • 3.5 Baths
    • 3,840 Sq Ft
    • Built 1903

    Last Sold Summary

    • $99/SF
    • 40 Days On Market

    Current Estimated Value $406,836

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

    113 G St, Oakland, MD 21550
  • /6

    $30,000

    Sold Oct 23, 2025

    28 Wild Turkey Ln, Oakland, MD 21550

    • Land
    • 1 Acre
    • $30,000 per Acre

    Last Sold Summary

    • 14 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    28 Wild Turkey Ln, Oakland, MD 21550
  • /62

    $349,900

    Sold May 08, 2026

    16 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft
    • Built 1974

    Last Sold Summary

    • $317/SF
    • 128 Days On Market

    Current Estimated Value $346,538

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, Oakland, MD 21550
  • /34

    $275,000

    Sold Jan 02, 2026

    34 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1992

    Last Sold Summary

    • 13 Days On Market

    Current Estimated Value $308,756

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

    34 Laurel Brook Dr, Oakland, MD 21550
  • /48

    $205,000

    Sold Mar 20, 2026

    565 Glendale Rd Unit 312, Oakland, MD 21550

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

    Last Sold Summary

    • 10% Below List Price
    • $261/SF
    • 6 Days On Market

    Current Estimated Value $252,949

    Last Listing Agent Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 312, Oakland, MD 21550
  • /47

    $285,000

    Sold Oct 31, 2025

    1764 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft
    • Built 1968

    Last Sold Summary

    • $124/SF
    • 175 Days On Market

    Current Estimated Value $292,198

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

    1764 Underwood Rd, Oakland, MD 21550
  • /52

    $920,000

    Sold Jun 15, 2026

    1295 Mountainview Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,550 Sq Ft
    • Built 2003

    Last Sold Summary

    • $259/SF
    • 3 Days On Market

    Current Estimated Value $924,656

    Last Listing Agent Debbie Roberts Long & Foster Real Estate, Inc.

    1295 Mountainview Dr, Oakland, MD 21550
  • /56

    $697,000

    Sold Dec 19, 2025

    969 Hoyes Run Rd, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft
    • Built 1998

    Last Sold Summary

    • $193/SF
    • 180 Days On Market

    Current Estimated Value $741,572

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
  • /2

    $10,000

    Sold Dec 19, 2025

    0 Maryland Hwy, Swanton, MD 21561

    • Land
    • 1.6 Acres
    • $6,250 per Acre

    Last Sold Summary

    • 220 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    0 Maryland Hwy, Swanton, MD 21561
  • /29

    $225,000

    Sold Nov 17, 2025

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft
    • Built 1990

    Last Sold Summary

    • $433/SF
    • 26 Days On Market

    Current Estimated Value $234,056

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
  • /39

    $195,000

    Sold Nov 12, 2025

    501 Christophers Way, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1994

    Last Sold Summary

    • $121/SF
    • 138 Days On Market

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    501 Christophers Way, Oakland, MD 21550
  • /41

    $218,000

    Sold Dec 01, 2025

    1136 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1971

    Last Sold Summary

    • $206/SF
    • 7 Days On Market

    Current Estimated Value $237,755

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

    1136 Black Oak Dr, Oakland, MD 21550
  • /18

    $200,000

    Sold Sep 15, 2025

    2571 Shady Dell Rd, Oakland, MD 21550

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

    Last Sold Summary

    • $119/SF
    • 62 Days On Market

    Current Estimated Value $255,686

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
  • /93

    $1,445,000

    Sold Nov 14, 2025

    128 Big Bass Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • Built 2023

    Last Sold Summary

    • $336/SF
    • 13 Days On Market

    Current Estimated Value $1,470,926

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
  • /78

    $1,780,000

    Sold Dec 19, 2025

    2345 Marsh Hill Rd, Mc Henry, MD 21541

    • 6 Beds
    • 6 Baths
    • 5,373 Sq Ft
    • Built 1990

    Last Sold Summary

    • $331/SF
    • 53 Days On Market

    Current Estimated Value $1,875,848

    Last Listing Agent James Matthews Taylor-Made Deep Creek Real Estate, LLC

    2345 Marsh Hill Rd, Mc Henry, MD 21541

Showing Results 161 - 200, Page 5 of 8

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