Homes Under $500K in Oakland, MD

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3 beds New construction With a pool

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24 of 48 Listings

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Homes Under $500K in Oakland, MD

24 of 48 Listings

26Active

48 listings

Homes Under $500K in Oakland, MD

Hide Map

24 of 48 Listings

Map

Homes Under $500K in Oakland, MD

24 of 48 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

26Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$279,000

2 bd · 1 ba · 772 sqft

565 Glendale Rd #316, Oakland, MD

Brent Daniel Housley · Railey Realty, Inc.

36Active

$235,000

2 bd · 2 ba · 1,152 sqft

1959 Birchwood Dr, Oakland, MD

Laura C Newhall · Taylor-Made Deep Creek Sales

77Active

$499,000

5 bd · 4 ba · 3,800 sqft

607 Pin Oak Cir, Oakland, MD

Rachel Bruch · Railey Realty, Inc.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

52Active

$229,000

3 bd · 2 ba · 1,612 sqft

139 S Oakhall Dr, Oakland, MD

Laura C Newhall · Taylor-Made Deep Creek Sales

25Active

$296,500

1 bd · 1 ba · 600 sqft

20160 Garett Hwy #105a, Oakland, MD

Richard B Orr · Railey Realty, Inc.

38Active

$74,990

3 bd · 1 ba · 1,932 sqft

102 Roanoke Ave, Oakland, MD

Heidi J Heiderman · Samson Properties

32Active

$289,000

4 bd · 2 ba · 2,240 sqft

586 Bray School Rd, Oakland, MD

Julia Mead · The KW Collective

34Active

$449,000

3 bd · 2 ba · 2,160 sqft

482 Pergin Farm Rd, Oakland, MD

Laura C Newhall · Taylor-Made Deep Creek Sales

61Active

$444,700

4 bd · 4 ba · 1,585 sqft

333 Sloan Tract Rd, Oakland, MD

Debra A Beitzel · Long & Foster Real Estate, Inc.

52Active

$399,900

3 bd · 2 ba · 1,464 sqft

1407 Broadford Rd, Oakland, MD

Laura C Newhall · Taylor-Made Deep Creek Sales

41Active

$375,000

2 bd · 2 ba · 1,404 sqft

18948 Garrett Hwy, Oakland, MD

Daniel Patrick Duggan Sr. · 1 Real Estate Source LLC

24Active

$225,000

1 bd · 1 ba · 0 sqft

565 Glendale Rd #213, Oakland, MD

Charlotte Savoy · The KW Collective

68Active

$460,000

5 bd · 2 ba · 2,860 sqft

5154 Maryland Hwy, Oakland, MD

Wilda Charlene Deremer Aburn · Coldwell Banker Home Town Realty

Price Reduced51Active

$374,900

3 bd · 2 ba · 1,456 sqft

181 Glotfelty Dr, Oakland, MD

Kathy L Gibson · Railey Realty, Inc.

Price Reduced43Active

$159,000

3 bd · 1 ba · 1,516 sqft

40 Sunshine, Oakland, MD

Danielle Luscombe · Taylor-Made Deep Creek Sales

29Active

$269,900

2 bd · 2 ba · 1,400 sqft

5 Laurel Brook Dr #5, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

Price Reduced35Active

$149,000

2 bd · 1 ba · 2,008 sqft

206 W Liberty St, Oakland, MD

Nicole Jackson · Railey Realty, Inc.

Price Reduced63Active

$325,000

5 bd · 3 ba · 2,165 sqft

112 E Pennington St, Oakland, MD

Sheila L Howell · Lake Homes Realty, LLC

60Active

$365,000

5 bd · 3 ba · 2,652 sqft

615 E Oak St, Oakland, MD

Lucas Alan Muenchow · Railey Realty, Inc.

43Active

$259,900

3 bd · 2 ba · 1,998 sqft

102 N 3rd St, Oakland, MD

Kevin D Liller · Railey Realty, Inc.

65Active

$464,900

3 bd · 4 ba · 1,838 sqft

256 Jeffrey Ln #28, Oakland, MD

Larry E Smith · Railey Realty, Inc.

Price Reduced47Active

$384,500

3 bd · 2 ba · 2,476 sqft

321 Deer Park Hotel Rd, Oakland, MD

Pamela Debnam · Houwzer, LLC

49Active

$379,500

1 bd · 1 ba · 636 sqft

20160 Garrett Hwy #C307, Oakland, MD

Justin D Liller · Railey Realty, Inc.

Price Reduced64Active

$375,000

4 bd · 2 ba · 2,234 sqft

1499 Foster Rd, Oakland, MD

Kelsey Lynn Meyers · Railey Realty, Inc.

Listing data & MLS disclosures

Bright MLS: 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: 2026-09-19 13:36:48 UTC

Oakland housing market

August 2026

Selling at 95.5% of asking price

Buyers here are paying below asking. MLS · 21 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 27, 2026

Median sale price: $289,250$116,000–$684,250 typical range
Price per sq. ft.: $281
Sales: 26
Paid in cash: 46.2%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $464,900
Homes for sale: 81
Median days on market: 30 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 41.5%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,536 sq. ft.

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

Explore Oakland homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Listing data & MLS disclosures

Bright MLS: 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: 2026-09-19 13:36:48 UTC

Oakland housing market

August 2026

Selling at 95.5% of asking price

Buyers here are paying below asking. MLS · 21 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 27, 2026

Median sale price: $289,250$116,000–$684,250 typical range
Price per sq. ft.: $281
Sales: 26
Paid in cash: 46.2%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $464,900
Homes for sale: 81
Median days on market: 30 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 41.5%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,536 sq. ft.

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

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Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Oakland housing market

Homes that sold · County records, as of Aug 27, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Oakland, MD community profile

Explore Oakland homes

Your local brokerage

Listing data & MLS disclosures

Oakland housing market

Homes that sold · County records, as of Aug 27, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Oakland, MD community profile