260

Recently Sold Oakland, MD Homes

Section Image
  • 5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    /50

    $239,000 Sold Feb 11, 2026

    5202 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,199 Sq Ft
    • Built 1950

    Last Sold Summary

    • $199/SF
    • 149 Days On Market

    Current Estimated Value $233,922

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
  • 0 Weber Ct, Oakland, MD 21550
    0 Weber Ct, Oakland, MD 21550
    0 Weber Ct, Oakland, MD 21550
    /13

    $20,000 Sold Nov 05, 2025

    0 Weber Ct, Oakland, MD 21550

    • Land
    • 0.24 Acre
    • $83,333 per Acre

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    0 Weber Ct, Oakland, MD 21550
  • 465 King Wildesen Rd, Oakland, MD 21550
    465 King Wildesen Rd, Oakland, MD 21550
    465 King Wildesen Rd, Oakland, MD 21550
    /40

    $335,000 Sold May 23, 2025

    465 King Wildesen Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1988

    Last Sold Summary

    • 22% Below List Price
    • $436/SF
    • 123 Days On Market

    Current Estimated Value $350,904

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

    465 King Wildesen Rd, Oakland, MD 21550
  • 9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    /20

    $17,000 Sold Oct 29, 2025

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    • Land
    • 0.96 Acre
    • $17,708 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
  • 0 E Water St, Oakland, MD 21550
    0 E Water St, Oakland, MD 21550
    /2

    $8,000 Sold Aug 29, 2025

    0 E Water St, Oakland, MD 21550

    • Land
    • 0.33 Acre
    • $24,242 per Acre

    Last Sold Summary

    • 2 Days On Market

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

    0 E Water St, Oakland, MD 21550
  • 204 E St, Oakland, MD 21550
    204 E St, Oakland, MD 21550
    204 E St, Oakland, MD 21550
    /37

    $120,000 Sold Dec 04, 2025

    204 E St, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 1975

    Last Sold Summary

    • $58/SF
    • 1 Day On Market

    Current Estimated Value $124,269

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
  • 403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    /47

    $270,000 Sold Jun 20, 2025

    403 O St, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,240 Sq Ft
    • Built 1976

    Last Sold Summary

    • $121/SF
    • 329 Days On Market

    Current Estimated Value $275,521

    Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    403 O St, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H708, Oakland, MD 21550
    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    /47

    $260,000 Sold Feb 27, 2026

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Built 1972

    Last Sold Summary

    • $473/SF
    • 234 Days On Market

    Current Estimated Value $280,937

    Last Listing Agent Charlotte Savoy The KW Collective

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • 421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    /107

    $1,350,000 Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,467,349

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
  • 249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    /67

    $855,000 Sold May 12, 2025

    249 Marys Ln, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,874 Sq Ft
    • Built 2017

    Last Sold Summary

    • $297/SF
    • 7 Days On Market

    Current Estimated Value $927,254

    Last Listing Agent Jon Bell Railey Realty, Inc.

    249 Marys Ln, Oakland, MD 21550
  • 939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    /61

    $820,000 Sold Sep 02, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1990

    Last Sold Summary

    • 18 Days On Market

    Current Estimated Value $845,117

    Last Listing Agent Sean Sober Taylor Made Deep Creek Real Estate

    939 Glendale Rd, Oakland, MD 21550
  • 237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, Oakland, MD 21550
    /100

    $1,860,000 Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Current Estimated Value $1,915,411

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
  • 416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, Oakland, MD 21550
    /56

    $157,000 Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $159,542

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
  • 12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    /51

    $425,000 Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Current Estimated Value $435,126

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
  • 0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    /3

    $13,000 Sold Apr 14, 2025

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550

    • Land
    • 2 Acres
    • $6,500 per Acre

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Julie Mead The KW Collective

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
  • 17979 Garrett Hwy, Oakland, MD 21550
    17979 Garrett Hwy, Oakland, MD 21550
    17979 Garrett Hwy, Oakland, MD 21550
    /37

    $365,900 Sold Mar 23, 2026

    17979 Garrett Hwy, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $381/SF
    • 9 Days On Market

    Current Estimated Value $357,220

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    17979 Garrett Hwy, Oakland, MD 21550
  • 216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    /86

    $1,100,000 Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,208,583

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

    216 Tarn Dr, Oakland, MD 21550
  • 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 Real Estate

    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

    Current Estimated Value $296,981

    Last Listing Agent James Matthews Taylor Made Deep Creek Real Estate

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
  • 189 Red Run Rd Unit 1C2, Oakland, MD 21550
    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    189 Red Run Rd Unit 1C2, 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 $515,730

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

    189 Red Run Rd Unit 1C2, 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

    Current Estimated Value $1,552,445

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, 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
  • 77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, 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 $594,833

    Last Listing Agent Jon Bell Railey Realty, Inc.

    77 Meadow Ct, 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

    Current Estimated Value $519,078

    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 $156,308

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

    1101 Wheeling Ave, Oakland, MD 21550
  • 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 $116,556

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

    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 $153,947

    Last Listing Agent Michelle Clark Taylor Made Deep Creek Real Estate

    414 D St, Oakland, 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 $542,898

    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

    Current Estimated Value $225,689

    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

    Current Estimated Value $197,321

    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 $558,057

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

    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 $246,561

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    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 $399,590

    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 $259,283

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Real Estate

    11 Laurel Brook Dr, 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 $180,876

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    5914 Maryland Hwy, Oakland, MD 21550
  • 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 $1,164,119

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, 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 $199,582

    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

    Current Estimated Value $778,208

    Last Listing Agent Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, 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

    Current Estimated Value $564,465

    Last Listing Agent Larry Smith Railey Realty, Inc.

    72 Cliff Dr, Oakland, MD 21550

Showing Results 121 - 160, Page 4 of 7

Maryland Garrett County Oakland

Recently Sold Real Estate & Homes in Oakland, MD

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