271

Recently Sold Oakland, MD Homes

Section Image
  • /38

    $280,000

    Sold Jul 29, 2026

    505 Southern Pines Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $224/SF
    • 124 Days On Market

    Current Estimated Value $290,150

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

    505 Southern Pines Dr, Oakland, MD 21550
  • /76

    $1,400,000

    Sold Dec 04, 2025

    1989 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,008 Sq Ft
    • Built 1964

    Last Sold Summary

    • $465/SF
    • 18 Days On Market

    Current Estimated Value $1,507,407

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1989 Lake Shore Dr, Oakland, MD 21550
  • /42

    $270,000

    Sold Nov 21, 2025

    11 Sunset Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2000

    Last Sold Summary

    • $193/SF
    • 29 Days On Market

    Current Estimated Value $282,691

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

    11 Sunset Dr, Oakland, MD 21550
  • /76

    $775,000

    Sold Aug 25, 2025

    3472 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 2,904 Sq Ft
    • Built 2007

    Last Sold Summary

    • $267/SF
    • 112 Days On Market

    Current Estimated Value $824,967

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

    3472 Lake Shore Dr, Oakland, MD 21550
  • /43

    $132,000

    Sold Aug 13, 2025

    723 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft
    • Built 1966

    Last Sold Summary

    • $134/SF
    • 2 Days On Market

    Current Estimated Value $168,148

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    723 E Oak St, Oakland, MD 21550
  • /9

    $23,000

    Sold Nov 03, 2025

    Lot 15 Little Mountain Rd, Oakland, MD 21550

    • Land
    • 2.71 Acres
    • $8,487 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 132 Days On Market

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

    Lot 15 Little Mountain Rd, Oakland, MD 21550
  • /62

    $1,399,000

    Sold Sep 05, 2025

    1589 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,872 Sq Ft
    • Built 2020

    Last Sold Summary

    • $747/SF
    • 3 Days On Market

    Current Estimated Value $1,499,645

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

    1589 Lake Shore Dr, Oakland, MD 21550
  • /73

    $305,000

    Sold Nov 06, 2025

    17 Driftwood Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,092 Sq Ft
    • Built 1978

    Last Sold Summary

    • $146/SF
    • 113 Days On Market

    Current Estimated Value $293,353

    Last Listing Agent Larry Smith Railey Realty, Inc.

    17 Driftwood Ln, Oakland, MD 21550
  • /47

    $180,000

    Sold Nov 24, 2025

    627 Hamill St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,322 Sq Ft
    • Built 1886

    Last Sold Summary

    • $136/SF
    • 2 Days On Market

    Current Estimated Value $189,828

    Last Listing Agent Rich Orr Railey Realty, Inc.

    627 Hamill St, Oakland, MD 21550
  • /14

    $17,000

    Sold Dec 18, 2025

    Lot 5A Valley Rd, Oakland, MD 21550

    • Land
    • 2.45 Acres
    • $6,939 per Acre

    Last Sold Summary

    • 1,047 Days On Market

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

    Lot 5A Valley Rd, Oakland, MD 21550
  • /29

    $369,900

    Sold Oct 17, 2025

    366 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1997

    Last Sold Summary

    • $266/SF
    • 152 Days On Market

    Current Estimated Value $372,891

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
  • /4

    $250,000

    Sold Feb 05, 2026

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550

    • Land
    • 45.7 Acres
    • $5,470 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
  • /2

    $20,000

    Sold Mar 03, 2026

    0 N Hammond St, Oakland, MD 21550

    • Land
    • 20,908 Sq Ft
    • $41,667 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 6 Days On Market

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

    0 N Hammond St, Oakland, MD 21550
  • /20

    $237,000

    Sold Oct 30, 2025

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550

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

    Last Sold Summary

    • $359/SF
    • 19 Days On Market

    Current Estimated Value $242,026

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

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
  • /35

    $165,000

    Sold Jun 15, 2026

    505 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,632 Sq Ft
    • Built 1950

    Last Sold Summary

    • $101/SF
    • 3 Days On Market

    Current Estimated Value $163,981

    Last Listing Agent Justin Liller Railey Realty, Inc.

    505 Shenandoah Ave, Oakland, MD 21550
  • /27

    $225,000

    Sold Feb 19, 2026

    1570 Garrett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft
    • Built 1984

    Last Sold Summary

    • $160/SF
    • 122 Days On Market

    Current Estimated Value $242,470

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

    1570 Garrett Rd, Oakland, MD 21550
  • /44

    $589,000

    Sold Sep 08, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft
    • Built 1995

    Last Sold Summary

    • $574/SF
    • 62 Days On Market

    Current Estimated Value $588,433

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
  • /27

    $165,000

    Sold Oct 30, 2025

    306 Shady Acre Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1972

    Last Sold Summary

    • $72/SF
    • 2 Days On Market

    Current Estimated Value $197,974

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
  • /5

    $34,500

    Sold Jan 15, 2026

    62 Crosby Dr, Oakland, MD 21550

    • Land
    • 27,442 Sq Ft
    • $54,762 per Acre

    Last Sold Summary

    • 73% Above List Price
    • 2,385 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Crosby Dr, Oakland, MD 21550
  • /20

    $17,000

    Sold Nov 21, 2025

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550

    • Land
    • 1.08 Acres
    • $15,741 per Acre

    Last Sold Summary

    • 24 Days On Market

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

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
  • /2

    $4,700,000

    Sold Jul 09, 2026

    1010 Holy Cross Dr, Oakland, MD 21550

    • 8 Beds
    • 8.5 Baths
    • 10,300 Sq Ft
    • Built 2013

    Last Sold Summary

    • 9% Below List Price
    • $456/SF
    • 78 Days On Market

    Current Estimated Value $5,183,675

    Last Listing Agent Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550
  • /64

    $1,150,000

    Sold Oct 24, 2025

    590 S Blakeslee Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,071 Sq Ft
    • Built 2000

    Last Sold Summary

    • $374/SF
    • 102 Days On Market

    Current Estimated Value $1,188,110

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

    590 S Blakeslee Rd, Oakland, MD 21550
  • /51

    $165,000

    Sold Jun 26, 2026

    565 Glendale Rd Unit 208, Oakland, MD 21550

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

    Last Sold Summary

    • 3% Below List Price
    • $341/SF
    • 10 Days On Market

    Current Estimated Value $183,964

    Last Listing Agent Jesse Shimrock Railey Realty, Inc.

    565 Glendale Rd Unit 208, Oakland, MD 21550
  • /39

    $450,000

    Sold Nov 10, 2025

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1972

    Last Sold Summary

    • $340/SF
    • 179 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
  • /63

    $711,000

    Sold Oct 15, 2025

    58 Glendale Woods Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,556 Sq Ft
    • Built 2006

    Last Sold Summary

    • $278/SF
    • 5 Days On Market

    Current Estimated Value $759,219

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
  • /14

    $80,000

    Sold Sep 26, 2025

    0 Coolidge Ave, Oakland, MD 21550

    • Land
    • 20,037 Sq Ft
    • $173,913 per Acre

    Last Sold Summary

    • 76 Days On Market

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

    0 Coolidge Ave, Oakland, MD 21550
  • /35

    $405,000

    Sold Dec 22, 2025

    45 Village Dr Unit 4, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Built 2004

    Last Sold Summary

    • $370/SF
    • 173 Days On Market

    Current Estimated Value $422,095

    Last Listing Agent Ana Dubin RE/MAX Realty Group

    45 Village Dr Unit 4, Oakland, MD 21550
  • /36

    $326,000

    Sold Oct 10, 2025

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1997

    Last Sold Summary

    • $272/SF
    • 42 Days On Market

    Current Estimated Value $334,445

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

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
  • /69

    $1,535,000

    Sold Jan 07, 2026

    272 McComas Beach Terrace, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,448 Sq Ft
    • Built 2005

    Last Sold Summary

    • $627/SF
    • 49 Days On Market

    Current Estimated Value $1,648,323

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    272 McComas Beach Terrace, Oakland, MD 21550
  • /33

    $425,000

    Sold Dec 19, 2025

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 0 Days On Market

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

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
  • /81

    $700,000

    Sold Feb 26, 2026

    329 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,632 Sq Ft
    • Built 2004

    Last Sold Summary

    • $266/SF
    • 112 Days On Market

    Current Estimated Value $738,115

    Last Listing Agent Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
  • /18

    $360,000

    Sold Jun 24, 2026

    3930 Mayhew Inn Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $162/SF
    • 44 Days On Market

    Current Estimated Value $392,891

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

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • /18

    $19,500

    Sold Sep 04, 2025

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550

    • Land
    • 1.48 Acres
    • $13,176 per Acre

    Last Sold Summary

    • 348 Days On Market

    Last Listing Agent Brady Harden Coldwell Banker Premier

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
  • /65

    $280,500

    Sold Sep 12, 2025

    290 Crellin Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • Built 1982

    Last Sold Summary

    • $127/SF
    • 96 Days On Market

    Current Estimated Value $295,463

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
  • /25

    $28,000

    Sold Jun 02, 2026

    9 Timber Falls Rd, Oakland, MD 21550

    • Land
    • 6.9 Acres
    • $4,058 per Acre

    Last Sold Summary

    • 220 Days On Market

    Last Listing Agent Jesse Shimrock Railey Realty, Inc.

    9 Timber Falls Rd, Oakland, MD 21550
  • /41

    $239,900

    Sold Sep 12, 2025

    502 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1956

    Last Sold Summary

    • $143/SF
    • 17 Days On Market

    Current Estimated Value $249,014

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, Oakland, MD 21550
  • /53

    $495,000

    Sold Oct 08, 2025

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft
    • Built 2004

    Last Sold Summary

    • $204/SF
    • 106 Days On Market

    Current Estimated Value $483,207

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

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
  • /67

    $760,000

    Sold Nov 14, 2025

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1993

    Last Sold Summary

    • $317/SF
    • 113 Days On Market

    Current Estimated Value $797,633

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
  • /63

    $920,000

    Sold Aug 22, 2025

    254 Middleton Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • $383/SF
    • 19 Days On Market

    Current Estimated Value $976,771

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
  • /10

    $90,000

    Sold Jul 22, 2026

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550

    • Land
    • 1.7 Acres
    • $52,941 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 89 Days On Market

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

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 7

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $611,924.
What is the average time to sell a house in Oakland, MD?
The houses for sale in Oakland, MD spend an average of 97 days on the market.
What is the number of active homes for sale in Oakland, MD?
There are 62 active homes for sale in Oakland, MD.
How many homes have sold over the last 12 months in Oakland, MD?
143 homes have sold in Oakland, MD over the last 12 months.

Home Price Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$422,500
Median Townhouse Sale Price
$462,450
Median 2 Bedroom Sale Price
$276,000
Median 1 Bedroom Sale Price
$221,950
Average Price Per Sq Ft
$275
Number of Homes for Sale
62
Last 12 months Home Sales
143
Months of Supply
5.20
Median List Price
$425,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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