313

Recently Sold Homes in 21550

Section Image
  • 968 Hutton Rd, Oakland, MD 21550
    968 Hutton Rd, Oakland, MD 21550
    968 Hutton Rd, Oakland, MD 21550
    /38

    $265,000 Sold Dec 30, 2025

    968 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2012

    Last Sold Summary

    • $148/SF
    • 25 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    968 Hutton Rd, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    /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

    Last Listing Agent James Matthews Taylor Made Deep Creek Vacations & Sales

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
  • 946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    /100

    $1,765,000 Sold Mar 14, 2025

    946 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,546 Sq Ft
    • Built 2001

    Last Sold Summary

    • $498/SF
    • 16 Days On Market

    Current Estimated Value $1,772,515

    Last Listing Agent Jon Bell Railey Realty, Inc.

    946 Glendale Rd, Oakland, MD 21550
  • 1567 Pergin Farm Rd, Oakland, MD 21550
    1567 Pergin Farm Rd, Oakland, MD 21550
    1567 Pergin Farm 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

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, Oakland, MD 21550
  • 112 B St, Oakland, MD 21550
    112 B St, Oakland, MD 21550
    112 B St, Oakland, MD 21550
    /42

    $175,000 Sold Mar 21, 2025

    112 B St, Oakland, MD 21550

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

    Last Sold Summary

    • $182/SF
    • 23 Days On Market

    Current Estimated Value $176,535

    Last Listing Agent Thomas Long Railey Realty, Inc.

    112 B St, Oakland, MD 21550
  • Lot 9 Pheasant Run, Oakland, MD 21550
    Lot 9 Pheasant Run, Oakland, MD 21550
    Lot 9 Pheasant Run, Oakland, MD 21550
    /10

    $59,000 Sold Jun 26, 2025

    Lot 9 Pheasant Run, Oakland, MD 21550

    • Land
    • 6.22 Acres
    • $9,486 per Acre

    Last Sold Summary

    • 15 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 9 Pheasant Run, Oakland, MD 21550
  • 36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, 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

    Last Listing Agent Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
  • 1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, 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 $168,667

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

    1101 Wheeling Ave, Oakland, MD 21550
  • Lot 38 Fern Loop, Sang Run, MD 21541
    Lot 38 Fern Loop, Sang Run, MD 21541
    Lot 38 Fern Loop, Sang Run, MD 21541
    /13

    $60,000 Sold Sep 24, 2025

    Lot 38 Fern Loop, Sang Run, MD 21541

    • Land
    • 0.61 Acre
    • $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
  • 110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    /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 $113,172

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    110 W Pennington St, Oakland, MD 21550
  • 414 D St, Oakland, MD 21550
    414 D St, Oakland, MD 21550
    414 D St, Oakland, MD 21550
    /45

    $150,000 Sold Aug 14, 2025

    414 D St, Oakland, MD 21550

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

    Last Sold Summary

    • $160/SF
    • 4 Days On Market

    Current Estimated Value $150,397

    Last Listing Agent Michelle Clark Taylor Made Deep Creek Vacations & Sales

    414 D St, Oakland, MD 21550
  • 72 Chimney Rock Ln, Mc Henry, MD 21541
    72 Chimney Rock Ln, Mc Henry, MD 21541
    72 Chimney Rock Ln, Mc Henry, MD 21541
    /13

    $50,000 Sold Feb 06, 2026

    72 Chimney Rock Ln, Mc Henry, MD 21541

    • Land
    • 0.57 Acre
    • $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
  • 96 Black Diamond Ct, McHenry, MD 21541
    96 Black Diamond Ct, McHenry, MD 21541
    96 Black Diamond Ct, McHenry, MD 21541
    /20

    $45,000 Sold Feb 21, 2025

    96 Black Diamond Ct, McHenry, MD 21541

    • Land
    • 0.63 Acre
    • $71,429 per Acre

    Last Sold Summary

    • 380 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    96 Black Diamond Ct, McHenry, MD 21541
  • 8 Pheasant Run Rd, Deer Park, MD 21550
    8 Pheasant Run Rd, Deer Park, MD 21550
    8 Pheasant Run Rd, Deer Park, MD 21550
    /8

    $60,000 Sold Apr 09, 2025

    8 Pheasant Run Rd, Deer Park, MD 21550

    • Land
    • 5.82 Acres
    • $10,309 per Acre

    Last Sold Summary

    • 484 Days On Market

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    8 Pheasant Run Rd, Deer Park, MD 21550
  • 3554 Lake Shore Dr, Oakland, MD 21550
    3554 Lake Shore Dr, Oakland, MD 21550
    3554 Lake Shore Dr, Oakland, MD 21550
    /48

    $525,000 Sold Jul 11, 2025

    3554 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1993

    Last Sold Summary

    • $405/SF
    • 232 Days On Market

    Current Estimated Value $531,727

    Last Listing Agent Robert Krop Keller Williams Realty Centre

    3554 Lake Shore Dr, Oakland, MD 21550
  • 142 Matthew Rd, Oakland, MD 21550
    142 Matthew Rd, Oakland, MD 21550
    142 Matthew Rd, Oakland, MD 21550
    /5

    $44,000 Sold Aug 11, 2025

    142 Matthew Rd, Oakland, MD 21550

    • Land
    • 1.83 Acres
    • $24,044 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    142 Matthew Rd, Oakland, MD 21550
  • 104 G St, Oakland, MD 21550
    104 G St, Oakland, MD 21550
    104 G St, 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

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550
  • 210 Seneca Ave, Oakland, MD 21550
    210 Seneca Ave, Oakland, MD 21550
    210 Seneca 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

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
  • 258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    /40

    $560,000 Sold Jun 20, 2025

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2009

    Last Sold Summary

    • $170/SF
    • 52 Days On Market

    Current Estimated Value $562,641

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
  • 114 Waterwheel Rd, Oakland, MD 21550
    114 Waterwheel Rd, Oakland, MD 21550
    114 Waterwheel Rd, Oakland, MD 21550
    /32

    $232,500 Sold Jul 10, 2025

    114 Waterwheel Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • $242/SF
    • 138 Days On Market

    Current Estimated Value $238,631

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    114 Waterwheel Rd, Oakland, MD 21550
  • 142 Lemley Dr Unit I, Oakland, MD 21550
    142 Lemley Dr Unit I, Oakland, MD 21550
    142 Lemley Dr Unit I, Oakland, MD 21550
    /26

    $400,000 Sold Apr 21, 2025

    142 Lemley Dr Unit I, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • Built 1987

    Last Sold Summary

    • 146 Days On Market

    Current Estimated Value $405,653

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    142 Lemley Dr Unit I, Oakland, MD 21550
  • 11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    /26

    $237,500 Sold Apr 15, 2025

    11 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 157 Days On Market

    Current Estimated Value $257,598

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Vacations & Sales

    11 Laurel Brook Dr, Oakland, MD 21550
  • 183 Kendall Camp Cir, McHenry, MD 21541
    183 Kendall Camp Cir, McHenry, MD 21541
    183 Kendall Camp Cir, McHenry, MD 21541
    /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 $684,555

    Last Listing Agent Jon Bell Railey Realty, Inc.

    183 Kendall Camp Cir, McHenry, MD 21541
  • 636 Paradise Heights, Oakland, MD 21550
    636 Paradise Heights, Oakland, MD 21550
    636 Paradise Heights, Oakland, MD 21550
    /46

    $1,120,000 Sold Jul 08, 2025

    636 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,028 Sq Ft
    • Built 1986

    Last Sold Summary

    • $552/SF
    • 11 Days On Market

    Current Estimated Value $1,110,707

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
  • 5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, Oakland, MD 21550
    /38

    $100,000 Sold Jul 11, 2025

    5914 Maryland Hwy, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft
    • Built 1973

    Last Sold Summary

    • $56/SF
    • 4 Days On Market

    Current Estimated Value $150,686

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    5914 Maryland Hwy, Oakland, MD 21550
  • 10 Peach Tree Ln, Deer Park, MD 21550
    10 Peach Tree Ln, Deer Park, MD 21550
    10 Peach Tree Ln, Deer Park, MD 21550
    /37

    $60,000 Sold Mar 19, 2025

    10 Peach Tree Ln, Deer Park, MD 21550

    • 2 Beds
    • 1 Bath
    • 500 Sq Ft
    • Built 1980

    Last Sold Summary

    • $120/SF
    • 80 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    10 Peach Tree Ln, Deer Park, MD 21550
  • 4643 Oakland Sang Run Rd, Oakland, MD 21550
    4643 Oakland Sang Run Rd, Oakland, MD 21550
    4643 Oakland Sang Run Rd, Oakland, MD 21550
    /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 $190,901

    Last Listing Agent Jon Bell Railey Realty, Inc.

    4643 Oakland Sang Run Rd, Oakland, MD 21550
  • 198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, 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

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
  • Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    /12

    $75,000 Sold Jul 10, 2025

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550

    • Land
    • 1.1 Acres
    • $68,182 per Acre

    Last Sold Summary

    • 7 Days On Market

    Last Listing Agent Lucas Muenchow Railey Realty, Inc.

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
  • 72 Cliff Dr, Oakland, MD 21550
    72 Cliff Dr, Oakland, MD 21550
    72 Cliff Dr, 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

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550
  • 113 G St, Oakland, MD 21550
    113 G St, Oakland, MD 21550
    113 G St, 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 $378,042

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    113 G St, Oakland, MD 21550
  • 1681 Shady Dell Rd, Oakland, MD 21550
    1681 Shady Dell Rd, Oakland, MD 21550
    1681 Shady Dell Rd, Oakland, MD 21550
    /31

    $189,000 Sold Jul 24, 2025

    1681 Shady Dell Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1985

    Last Sold Summary

    • $197/SF
    • 2 Days On Market

    Current Estimated Value $188,945

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Vacations & Sales

    1681 Shady Dell Rd, Oakland, MD 21550
  • 28 Wild Turkey Ln, Oakland, MD 21550
    28 Wild Turkey Ln, Oakland, MD 21550
    28 Wild Turkey Ln, 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 Vacations & Sales

    28 Wild Turkey Ln, Oakland, MD 21550
  • 234 Maple Del Ln, Oakland, MD 21550
    234 Maple Del Ln, Oakland, MD 21550
    234 Maple Del Ln, Oakland, MD 21550
    /51

    $435,000 Sold May 27, 2025

    234 Maple Del Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,750 Sq Ft
    • Built 1995

    Last Sold Summary

    • $158/SF
    • 306 Days On Market

    Current Estimated Value $458,329

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    234 Maple Del Ln, Oakland, MD 21550
  • 34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook 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

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    34 Laurel Brook Dr, Oakland, MD 21550
  • 1764 Underwood Rd, Oakland, MD 21550
    1764 Underwood Rd, Oakland, MD 21550
    1764 Underwood Rd, 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 $278,744

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    1764 Underwood Rd, Oakland, MD 21550
  • 969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, 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

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
  • 0 Maryland Hwy, Swanton, MD 21561
    0 Maryland Hwy, Swanton, MD 21561
    /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
  • 36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    /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

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
  • 501 Christophers Way, Oakland, MD 21550
    501 Christophers Way, Oakland, MD 21550
    501 Christophers Way, 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 Vacations & Sales

    501 Christophers Way, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 8

Maryland Garrett County Oakland 21550

Recently Sold Real Estate & Homes in 21550

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