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85 listings

Homes for Sale in Oakland, MD

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24 of 85 Listings

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24 of 85 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

36Active

$235,000

2 bd · 2 ba · 1,152 sqft

1959 Birchwood Dr, Oakland, MD

Laura C Newhall · Taylor-Made Deep Creek Sales

67Active

$639,000

3 bd · 3 ba · 1,933 sqft

1529 Paradise Point Rd, Oakland, MD

Elizabeth S Spiker Holcomb · 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.

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

52Active

$645,000

2 bd · 2 ba · 1,520 sqft

100 San Francisco St, Oakland, MD

Nick Fratz-Orr · Railey Realty, Inc.

61Active

$444,700

4 bd · 4 ba · 1,585 sqft

333 Sloan Tract Rd, Oakland, MD

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

53Active

$1,199,000

4 bd · 3 ba · 1,844 sqft

20698 Garrett Hwy, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

53Active

$920,000

3 bd · 2 ba · 1,152 sqft

184 Upper Penn Point Dr, Oakland, MD

Amy Webster Mangum · Railey Realty, Inc.

52Active

$399,900

3 bd · 2 ba · 1,464 sqft

1407 Broadford Rd, Oakland, MD

Laura C Newhall · Taylor-Made Deep Creek Sales

66Active

$899,900

5 bd · 6 ba · 3,160 sqft

395 Woodlands Hill Ln, Oakland, MD

Jonathan D Bell · Railey Realty, Inc.

41Active

$375,000

2 bd · 2 ba · 1,404 sqft

18948 Garrett Hwy, Oakland, MD

Daniel Patrick Duggan Sr. · 1 Real Estate Source LLC

59Active

$689,000

4 bd · 3 ba · 2,402 sqft

180 Paradise Ridge Rd, Oakland, MD

Brian P Homberg · Taylor-Made Deep Creek Sales

124Active

$3,950,000

8 bd · 10 ba · 6,486 sqft

1131 Lake Shore Dr, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

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

51Active

$399,000

3 bd · 2 ba · 1,456 sqft

181 Glotfelty Dr, Oakland, MD

Kathy L Gibson · Railey Realty, Inc.

60Active

$799,900

4 bd · 4 ba · 0 sqft

15 Byran Dr, Oakland, MD

Jonathan D Bell · Railey Realty, Inc.

Price Reduced66Active

$769,000

4 bd · 4 ba · 3,376 sqft

325 Markwood Dr, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

Price Reduced43Active

$169,000

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

1 2…4

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: 2026-09-15 20:23:40 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

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

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

New construction
With a pool

Nearby areas

ZIP codes

21550 (91)
21541 (78)
21561 (40)
21562 (15)
21536 (10)
21531 (8)
21539 (7)
21520 (5)

Cities

Mc Henry (77)
Swanton (40)
Westernport (14)
Grantsville (10)
Friendsville (8)
Lonaconing (7)
Accident (5)
Barton (5)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

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: 2026-09-15 20:23:40 UTC

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

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

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 Homes for Sale | Realty.com

Nearby areas

ZIP codes

21550 (91)
21541 (78)
21561 (40)
21562 (15)
21536 (10)
21531 (8)
21539 (7)
21520 (5)

Cities

Mc Henry (77)
Swanton (40)
Westernport (14)
Grantsville (10)
Friendsville (8)
Lonaconing (7)
Accident (5)
Barton (5)