5 Bedroom Homes in Oakland, MD

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3 beds New construction With a pool

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19 Listings

Map

5 Bedroom Homes in Oakland, MD

19 Listings

66Active

19 listings

5 Bedroom Homes in Oakland, MD

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19 Listings

Map

5 Bedroom Homes in Oakland, MD

19 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

66Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$899,900

5 bd · 6 ba · 3,160 sqft

395 Woodlands Hill Ln, Oakland, MD

Jonathan D Bell · Railey Realty, Inc.

99Active

$799,000

5 bd · 4 ba · 3,480 sqft

18 Mountainside Ct, Oakland, MD

Justin D Liller · Railey Realty, Inc.

Price Reduced81Active

$2,150,000

5 bd · 4 ba · 4,200 sqft

59 Boyd Paugh Ln, Oakland, MD

James Calvin Matthews · Taylor-Made Deep Creek Sales

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

68Active

$460,000

5 bd · 2 ba · 2,860 sqft

5154 Maryland Hwy, Oakland, MD

Wilda Charlene Deremer Aburn · Coldwell Banker Home Town Realty

62Active

$775,000

5 bd · 5 ba · 4,284 sqft

251 Robinwood Dr, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

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.

Price Reduced62Active

$745,000

5 bd · 3 ba · 2,200 sqft

943 Paradise Hts, Oakland, MD

Lucas Alan Muenchow · Railey Realty, Inc.

61Active

$615,000

5 bd · 5 ba · 3,300 sqft

308 Winding Trail Ln #11B, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

Price Reduced86Active

$579,000

5 bd · 4 ba · 3,542 sqft

428 Sam Snead Cir, Oakland, MD

Justin D Liller · Railey Realty, Inc.

Price Reduced48Active

$365,000

5 bd · 2 ba · 3,660 sqft

321 N 3rd St, Oakland, MD

Christina M Ford · CENTURY 21 New Millennium

Price Reduced63Active

$899,900

5 bd · 5 ba · 4,284 sqft

251 Robinwood Dr, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

Price Reduced55Active

$699,000

5 bd · 4 ba · 4,230 sqft

312 Moss Creek Cir, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

56Active

$745,000

5 bd · 3 ba · 2,640 sqft

638 Glendale Rd, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

64Active

$1,400,000

5 bd · 4 ba · 2,832 sqft

827 Penn Point Rd, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

Price Reduced62Active

$999,000

5 bd · 3 ba · 2,592 sqft

660 Glendale Rd, Oakland, MD

Nick Fratz-Orr · Railey Realty, Inc.

50Active

$679,900

5 bd · 5 ba · 3,000 sqft

4A Mystic Creek Trl, Oakland, MD

Justin D Liller · Railey Realty, Inc.

Price Reduced115Active

$2,350,000

5 bd · 7 ba · 5,376 sqft

2725 Stockslager Rd, Oakland, MD

Shelia R McCracken · Taylor-Made Deep Creek Sales

Price Reduced52Active

$749,900

5 bd · 4 ba · 2,364 sqft

25 Silver Tree Ln, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

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: 2026-09-01 19:25:54 UTC

Oakland housing market

August 2026 · This period is still settling

Selling at 95.6% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Aug 28, 2026

Homes that sold · County records, as of Aug 12, 2026

Median sale price: $295,500$210,000–$544,500 typical range
Price per sq. ft.: $273
Sales: 15
Paid in cash: 46.7%

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Median list price: $464,900
Homes for sale: 81
Median days on market: 21 days

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

Year-over-year: 44.6%

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: 2026-09-01 19:25:54 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 · This period is still settling

Selling at 95.6% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Aug 28, 2026

Homes that sold · County records, as of Aug 12, 2026

Median sale price: $295,500$210,000–$544,500 typical range
Price per sq. ft.: $273
Sales: 15
Paid in cash: 46.7%

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Median list price: $464,900
Homes for sale: 81
Median days on market: 21 days

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

Year-over-year: 44.6%

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.

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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 12, 2026

Homes on the market · MLS, as of Aug 28, 2026–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, MD community profile

Oakland housing market

Homes that sold · County records, as of Aug 12, 2026

Homes on the market · MLS, as of Aug 28, 2026–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