Luxury Homes in Oakland, MD

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3 beds New construction With a pool

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11 Listings

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Luxury Homes in Oakland, MD

11 Listings

53Active

11 listings

Luxury Homes in Oakland, MD

Hide Map

11 Listings

Map

Luxury Homes in Oakland, MD

11 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

53Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$1,199,000

4 bd · 3 ba · 1,844 sqft

20698 Garrett Hwy, Oakland, MD

Elizabeth S Spiker Holcomb · 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

Price Reduced33Active

$1,095,000

2 bd · 3 ba · 2,914 sqft

826 G Swauger Rd, Oakland, MD

Larry E. Roth · Railey Realty, Inc.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced44Active

$1,425,000

3 bd · 2 ba · 1,695 sqft

187 Lower Penn Point Dr, Oakland, MD

Amy Webster Mangum · Railey Realty, Inc.

145Active

$3,249,000

4 bd · 5 ba · 6,036 sqft

415 Nazelrod Rd, Oakland, MD

Larry E Smith · Railey Realty, Inc.

Price Reduced59Active

$1,089,000

4 bd · 5 ba · 2,656 sqft

122 Woodlands Hill Ln, Oakland, MD

Brian P Homberg · Taylor-Made Deep Creek Sales

43Active

$2,499,900

4 bd · 2 ba · 2,190 sqft

83 Bethlehem Rd, Oakland, MD

Jonathan D Bell · Railey Realty, Inc.

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 Reduced97Active

$1,059,900

4 bd · 6 ba · 3,032 sqft

52 Dam View Dr, Oakland, MD

Michael Fenton · Railey Realty, Inc.

109Active

$6,499,900

7 bd · 9 ba · 11,417 sqft

47 Holy Cross, Oakland, MD

Jonathan D Bell · Railey Realty, Inc.

Price Reduced45Active

$1,329,000

6 bd · 5 ba · 4,113 sqft

439 Paradise Hts, Oakland, MD

Michael N Kennedy · 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: 2026-09-15 18:47:41 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: 2026-09-15 18:47:41 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: 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.

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Registered offenders on the map

Registered offenders on the map

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, MD community profile

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