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Homes for sale in Oakland, MD

Figures for Oakland, MD, week ending September 15, 2026.

Paige

watching Oakland · 185 homes for sale

Paige

The biggest price drop in town this week happened at 122 Woodlands Hill Lane, a residential property that just moved from $1,200,000 down to $1,089,000. If you want to get out and look at places, 1959 Birchwood Drive in Youghiougheny Mountain is a 2 bedrooms residential listed 4 days ago for $235,000. There is also 204 Farm View Lane in George Brunson, a 3 bedrooms residential asking $540,000 that came on 5 days ago. Right now homes are staying listed for a median of 62 days, while the 30 homes sold in the last 30 days spent a median of 51 days on market. With 3 new listings arriving this week and 7 price cuts, sellers are showing a willingness to adjust their expectations to get deals moving. Are you looking to buy or sell a home in Oakland?

1959 BIRCHWOOD DRIVE

For SaleBright MLS

1959 BIRCHWOOD DRIVE, Oakland

2 bd · 2 ba · House · 5 DOM

MDGA2012770, Taylor-Made Deep Creek Sales

204 FARM VIEW LANE

For SaleBright MLS

204 FARM VIEW LANE, Oakland

3 bd · 4 ba · House · 6 DOM

MDGA2012756, RE/MAX Results

122 WOODLANDS HILL LANE

For SaleBright MLS

122 WOODLANDS HILL LANE, Oakland

4 bd · 5 ba · House · 119 DOM

MDGA2011982, Taylor-Made Deep Creek Sales

1529 PARADISE POINT ROAD

For SaleBright MLS

1529 PARADISE POINT ROAD, Oakland

3 bd · 2.5 ba · House · 6 DOM

MDGA2012752, Taylor-Made Deep Creek Sales

607 PIN OAK CIRCLE

For SaleBright MLS

607 PIN OAK CIRCLE, Oakland

5 bd · 4 ba · House · 12 DOM

MDGA2012740, Railey Realty, Inc.

139 OAKHALL DRIVE

For SaleBright MLS

139 OAKHALL DRIVE, Oakland

3 bd · 2 ba · House · 13 DOM

MDGA2012746, Taylor-Made Deep Creek Sales

20160 GARETT HIGHWAY Unit 105A

For SaleBright MLS

20160 GARETT HIGHWAY Unit 105A, Oakland

1 bd · 1 ba · Condo · 13 DOM

MDGA2012720, Railey Realty, Inc.

102 ROANOKE AVENUE

For SaleBright MLS

102 ROANOKE AVENUE, Oakland

3 bd · 1 ba · House · 14 DOM

MDGA2012700, Samson Properties

586 BRAY SCHOOL ROAD

For SaleBright MLS

586 BRAY SCHOOL ROAD, Oakland

4 bd · 2 ba · House · 15 DOM

MDGA2012712, The KW Collective

2849 SHINGLE CAMP ROAD

Under ContractBright MLS

2849 SHINGLE CAMP ROAD, Oakland

3 bd · 2 ba · House · 15 DOM

MDGA2012730, Railey Realty, Inc.

482 PERGIN FARM ROAD

For SaleBright MLS

482 PERGIN FARM ROAD, Oakland

3 bd · 2 ba · House · 20 DOM

MDGA2012680, Taylor-Made Deep Creek Sales

100 SAN FRANCISCO STREET

For SaleBright MLS

100 SAN FRANCISCO STREET, Oakland

2 bd · 2 ba · House · 23 DOM

MDGA2012742, Railey Realty, Inc.

333 SLOAN TRACT ROAD

For SaleBright MLS

333 SLOAN TRACT ROAD, Oakland

4 bd · 4 ba · House · 30 DOM

MDGA2012576, Long & Foster Real Estate, Inc.

20698 GARRETT HIGHWAY

For SaleBright MLS

20698 GARRETT HIGHWAY, Oakland

4 bd · 3 ba · House · 31 DOM

MDGA2012616, Taylor-Made Deep Creek Sales

184 UPPER PENN POINT DRIVE

For SaleBright MLS

184 UPPER PENN POINT DRIVE, Oakland

3 bd · 2 ba · House · 32 DOM

MDGA2012648, Railey Realty, Inc.

704 OLD CRELLIN ROAD

Under ContractBright MLS

704 OLD CRELLIN ROAD, Oakland

5 bd · 2.5 ba · House · 33 DOM

MDGA2012604, The KW Collective

1407 BROADFORD ROAD

For SaleBright MLS

1407 BROADFORD ROAD, Oakland

3 bd · 2 ba · House · 33 DOM

MDGA2012662, Taylor-Made Deep Creek Sales

395 WOODLANDS HILL LANE

For SaleBright MLS

395 WOODLANDS HILL LANE, Oakland

5 bd · 6 ba · House · 35 DOM

MDGA2012628, Railey Realty, Inc.

18948 GARRETT HIGHWAY

For SaleBright MLS

18948 GARRETT HIGHWAY, Oakland

2 bd · 2 ba · House · 40 DOM

MDGA2012540, 1 Real Estate Source LLC

565 GLENDALE ROAD Unit 213

For SaleBright MLS

565 GLENDALE ROAD Unit 213, Oakland

1 bd · 1 ba · Condo · 46 DOM

MDGA2012506, The KW Collective

Tap a home and I'll open it here — we can keep talking about it.

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