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Homes Under $400K in Oakland, MD
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Homes Under $400K in Oakland, MD

Homes Under $400K in Oakland, MD

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24 of 38 Listings
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Homes Under $400K in Oakland, MD

24 of 38 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 216 N 12th St — photo1Active

    $285,000

    3 bd · 2 ba · 1,984 sqft

    216 N 12th St, Oakland, MD

    Lisa A Pannell · Long & Foster Real Estate, Inc.

  2. 210 Seneca Ave — photo34Active

    $229,000

    3 bd · 1 ba · 1,204 sqft

    210 Seneca Ave, Oakland, MD

    Daniel Shockey · Taylor-Made Deep Creek Sales

  3. 565 Glendale Rd #316 — photo26Active

    $279,000

    2 bd · 1 ba · 772 sqft

    565 Glendale Rd #316, Oakland, MD

    Brent Daniel Housley · Railey Realty, Inc.

  4. 127 Jeffrey Ln #4 — photo49Active

    $279,000

    2 bd · 1 ba · 700 sqft

    127 Jeffrey Ln #4, Oakland, MD

    Kathy L Gibson · Railey Realty, Inc.

  5. 1959 Birchwood Dr — photo36Active

    $235,000

    2 bd · 2 ba · 1,152 sqft

    1959 Birchwood Dr, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  6. 139 S Oakhall Dr — photo52Active

    $229,000

    3 bd · 2 ba · 1,612 sqft

    139 S Oakhall Dr, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  7. 20160 Garett Hwy #105a — photo25Active

    $296,500

    1 bd · 1 ba · 600 sqft

    20160 Garett Hwy #105a, Oakland, MD

    Richard B Orr · Railey Realty, Inc.

  8. 102 Roanoke Ave — photoPrice Reduced38Active

    $69,990

    3 bd · 1 ba · 1,932 sqft

    102 Roanoke Ave, Oakland, MD

    Heidi J Heiderman · Samson Properties

  9. 586 Bray School Rd — photo32Active

    $289,000

    4 bd · 2 ba · 2,240 sqft

    586 Bray School Rd, Oakland, MD

    Julia Mead · The KW Collective

  10. 1407 Broadford Rd — photo52Active

    $399,900

    3 bd · 2 ba · 1,464 sqft

    1407 Broadford Rd, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  11. 18948 Garrett Hwy — photo41Active

    $375,000

    2 bd · 2 ba · 1,404 sqft

    18948 Garrett Hwy, Oakland, MD

    Daniel Patrick Duggan Sr. · 1 Real Estate Source LLC

  12. 565 Glendale Rd #213 — photoPrice Reduced24Active

    $215,000

    1 bd · 1 ba · 0 sqft

    565 Glendale Rd #213, Oakland, MD

    Charlotte Savoy · The KW Collective

  13. 181 Glotfelty Dr — photoPrice Reduced51Active

    $374,900

    3 bd · 2 ba · 1,456 sqft

    181 Glotfelty Dr, Oakland, MD

    Kathy L Gibson · Railey Realty, Inc.

  14. 40 Sunshine — photoPrice Reduced43Active

    $159,000

    3 bd · 1 ba · 1,516 sqft

    40 Sunshine, Oakland, MD

    Danielle Luscombe · Taylor-Made Deep Creek Sales

  15. 5 Laurel Brook Dr #5 — photo29Active

    $269,900

    2 bd · 2 ba · 1,400 sqft

    5 Laurel Brook Dr #5, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  16. 206 W Liberty St — photoPrice Reduced35Active

    $149,000

    2 bd · 1 ba · 2,008 sqft

    206 W Liberty St, Oakland, MD

    Nicole Jackson · Railey Realty, Inc.

  17. 112 E Pennington St — photoPrice Reduced63Active

    $325,000

    5 bd · 3 ba · 2,165 sqft

    112 E Pennington St, Oakland, MD

    Sheila L Howell · Lake Homes Realty, LLC

  18. 615 E Oak St — photo60Active

    $365,000

    5 bd · 3 ba · 2,652 sqft

    615 E Oak St, Oakland, MD

    Lucas Alan Muenchow · Railey Realty, Inc.

  19. 102 N 3rd St — photo43Active

    $259,900

    3 bd · 2 ba · 1,998 sqft

    102 N 3rd St, Oakland, MD

    Kevin D Liller · Railey Realty, Inc.

  20. 321 Deer Park Hotel Rd — photoPrice Reduced47Active

    $384,500

    3 bd · 2 ba · 2,476 sqft

    321 Deer Park Hotel Rd, Oakland, MD

    Pamela Debnam · Houwzer, LLC

  21. 20160 Garrett Hwy #C307 — photo49Active

    $379,500

    1 bd · 1 ba · 636 sqft

    20160 Garrett Hwy #C307, Oakland, MD

    Justin D Liller · Railey Realty, Inc.

  22. 1499 Foster Rd — photoPrice Reduced64Active

    $375,000

    4 bd · 2 ba · 2,234 sqft

    1499 Foster Rd, Oakland, MD

    Kelsey Lynn Meyers · Railey Realty, Inc.

  23. 560 Glendale Rd — photoPrice Reduced24Active

    $374,900

    2 bd · 1 ba · 700 sqft

    560 Glendale Rd, Oakland, MD

    Lauren McCann · Railey Realty, Inc.

  24. 20160 Garrett Hwy #H706 — photo27Active

    $309,000

    1 bd · 1 ba · 550 sqft

    20160 Garrett Hwy #H706, Oakland, MD

    James Calvin Matthews · Taylor-Made Deep Creek Sales

12

About Homes Under $400K in Oakland, MD

Homes Under $400K in Oakland, MD: 38 active listings as of October 5, 2026, 22:14 UTC.

Property types among these 38 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence1539.5%
Condominium615.8%

Explore Oakland homes

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-10-05 19:27:43 UTC
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    Your local brokerage

    TO

    Thomas O'Leary

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    Lic. #01-6355

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    Oakland, MD community profile

    Population
    1,810
    Median income
    $67,177
    Housing units
    929
    People per sq. mi.
    8.8
    Area
    205.5 sq. mi.

    Source: HJN community data

    Oakland housing market

    September 2026

    Oakland 12-month median sale price trend

    Selling at 96.5% of asking price

    Buyers here are paying below asking. MLS · 21 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $318,500$115,000–$520,000 typical range
    Price per sq. ft.
    $192
    Sales
    29
    Paid in cash
    44.8%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $454,500
    Homes for sale
    78
    Median days on market
    53 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    64.3%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    1,536 sq. ft.