Oakland, MD homes for sale & real estate

view of front of home featuring a garage and a front yard

view of front facade featuring a front yard

New - 8 hours on Rocket

$9,025 Closing Credit¹

$760,000

6 beds • 2.5 baths • 2,672 sqft

6652 George Washington Hwy, Oakland MD 21550

Andrew C Orr, Listing Office: Railey Realty, Inc.

snow covered back of property featuring a deck

living room with a wood stove, ceiling fan, lofted ceiling, and hardwood / wood-style flooring

living room featuring hardwood / wood-style flooring, ceiling fan, and lofted ceiling

$3,978 Closing Credit¹

$335,000

2 beds • 1.5 baths • 1,600 sqft

1359 Cedar Ln, Oakland MD 21550

Patrick Christopher Murphy, Listing Office: Home Towne Real Estate

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front of property with a fire pit and a front yard

wooden terrace featuring a mountain view, a hot tub, and grilling area

view of patio / terrace with an outdoor fire pit

$9,855 Closing Credit¹

$829,900

5 beds • 4.5 baths • 2,250 sqft

158 Silver Tree Ln, Oakland MD 21550

Jonathan D Bell, Listing Office: Railey Realty, Inc.

111 Tarn Dr, Oakland MD, 21550 land for sale

Listing photo 2 for 111 Tarn Dr, Oakland MD 21550

Listing photo 3 for 111 Tarn Dr, Oakland MD 21550

$57,900

Land • 1 Acre

111 Tarn Dr, Oakland MD 21550

Amy Elizabeth Grubby, Listing Office: 3% Realty Elite, Simply Full Service Realty

465 King Wildesen Rd, Oakland MD, 21550, 2 bedrooms, 1 bath house for sale

Listing photo 2 for 465 King Wildesen Rd, Oakland MD 21550

Listing photo 3 for 465 King Wildesen Rd, Oakland MD 21550

$5,105 Closing Credit¹

$429,900

2 beds • 1 bath • 768 sqft

465 King Wildesen Rd, Oakland MD 21550

Listing Office: BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

birds eye view of property featuring a rural view

$5,105 Closing Credit¹

$429,900

2 beds • 1 bath • 768 sqft

465 King Wildesen Rd, Oakland MD 21550

Adam Murray, Listing Office: BHHS Touchdown Home Pros Realty

snow covered property featuring a sunroom

$2,791 Closing Credit¹

$235,000

5 beds • 1.5 baths • 1,536 sqft

511 Main St, Deer Park MD 21550

Daniel Patrick Duggan Sr., Listing Office: 1 Real Estate Source LLC

Room to negotiate?

Median Sold Price

$385K

Avg. Sale Time

127 Days

Based on our December 2024 Market Report.

back of house with a wooden deck and a lawn

Backup offers

$10,000 Closing Credit¹

$849,999

5 beds • 5 baths • 3,088 sqft

297 Woodlands Hill Ln, Oakland MD 21550

Roberta J McNamara, Listing Office: RE/MAX Results

birds eye view of property featuring a water view

$2,624 Closing Credit¹

$221,000

1 bed • 1 bath • 527 sqft

565 Glendale Rd Unit 212, Oakland MD 21550

Nick Fratz-Orr, Listing Office: Railey Realty, Inc.

$8,016 Closing Credit¹

$675,000

3 beds • 2 baths • 2,446 sqft

1118 Lake Shore Dr, Oakland MD 21550

Susan R Bell, Listing Office: Railey Realty, Inc.

living room with ceiling fan, sink, and light hardwood / wood-style floors

laundry area with light hardwood / wood-style floors and stacked washer / drying machine

$10,000 Closing Credit¹

$1,100,000

2 beds • 3.5 baths • 2,106 sqft

145 Lower Penn Point Dr, Oakland MD 21550

Emillie H. Albrecht, Listing Office: Real Broker, LLC

White Pine Cir, Oakland MD, 21550 land for sale

Listing photo 2 for White Pine Cir, Oakland MD 21550

Listing photo 3 for White Pine Cir, Oakland MD 21550

$20,000

Land • 1 Acre

White Pine Cir, Oakland MD 21550

Nina A Beitzel, Listing Office: Railey Realty, Inc.

rear view of house featuring a deck and a yard

3D tour

$3,889 Closing Credit¹

$327,500

4 beds • 3 baths • 2,720 sqft

202 Deerfield Dr, Oakland MD 21550

Sharon K Kay Murray, Listing Office: Coldwell Banker Home Town Realty

back of property featuring a lawn, a wooden deck, and a patio

rear view of property featuring a lawn and a deck

$10,000 Closing Credit¹

$1,479,000

4 beds • 3 baths • 1,844 sqft

20698 Garrett Hwy, Oakland MD 21550

Elizabeth S Spiker Holcomb, Listing Office: Taylor Made Deep Creek Vacations & Sales

view of front of house with a wooden deck

Backup offers

$5,807 Closing Credit¹

$489,000

3 beds • 2 baths • 2,160 sqft

741 Hoyes Run Rd, Oakland MD 21550

Elizabeth S Spiker Holcomb, Listing Office: Taylor Made Deep Creek Vacations & Sales

bungalow with a front yard, an outbuilding, and a garage

$2,969 Closing Credit¹

$250,000

3 beds • 1 bath • 1,296 sqft

476 Garrett Hwy, Oakland MD 21550

Brent Daniel Housley, Listing Office: Railey Realty, Inc.

view of front property with covered porch and a garage

view of front property featuring a porch, a garage, and a lawn

snow covered house featuring a lawn and a wooden deck

Backup offers

$5,807 Closing Credit¹

$489,000

5 beds • 3.5 baths • 3,016 sqft

1014 Madison, Oakland MD 21550

Justin D Liller, Listing Office: Railey Realty, Inc.

$6,294 Closing Credit¹

$530,000

2 beds • 1 bath

15 Village Dr Unit 1, Oakland MD 21550

Dale M Carpenter, Listing Office: Railey Realty, Inc.

back of house featuring a deck and a jacuzzi

birds eye view of property with a water view

living room with wood ceiling, a wealth of natural light, light wood-type flooring, and high vaulted ceiling

Backup offers

$5,451 Closing Credit¹

$459,000

4 beds • 2 baths • 1,296 sqft

247 Sloan Tract Rd, Oakland MD 21550

Andrew L Eiswert, Listing Office: Railey Realty, Inc.

view of front of home featuring a porch and a front lawn

$2,482 Closing Credit¹

$209,000

3 beds • 2 baths • 2,060 sqft

3941 Pleasant Valley Rd, Oakland MD 21550

Ben W Maust, Listing Office: Railey Realty, Inc.

view of front of home featuring a front yard and a wooden deck

back of property featuring outdoor lounge area, a hot tub, and a wooden deck

back of house with a wooden deck and an outdoor living space

$10,000 Closing Credit¹

$1,599,000

5 beds • 3 baths • 2,080 sqft

383 Penn Cove Rd, Oakland MD 21550

Elizabeth S Spiker Holcomb, Listing Office: Taylor Made Deep Creek Vacations & Sales

$1,959 Closing Credit¹

$165,000

2 beds • 1 bath • 1,080 sqft

4960 Hutton Rd, Oakland MD 21550

Justin D Liller, Listing Office: Railey Realty, Inc.

LOT5 Bobcat Hill Ln, Oakland MD, 21550 land for sale

Listing photo 2 for LOT5 Bobcat Hill Ln, Oakland MD 21550

Listing photo 3 for LOT5 Bobcat Hill Ln, Oakland MD 21550

Backup offers

$99,000

Land • 2.36 Acres

LOT5 Bobcat Hill Ln, Oakland MD 21550

Kimberly S. Palmer, Listing Office: Marquee Properties, Inc.

carpeted empty room featuring a baseboard heating unit

Backup offers

$2,165 Closing Credit¹

$182,300

3 beds • 1 bath • 960 sqft

112 B St, Oakland MD 21550

Thomas Long, Listing Office: Railey Realty, Inc.

view of front of house featuring a garage

rear view of house featuring a wooden deck and a hot tub

3D tour

$6,994 Closing Credit¹

$589,000

5 beds • 4.5 baths • 3,300 sqft

170 Winding Trail Ln Unit 4B, Oakland MD 21550

Elizabeth S Spiker Holcomb, Listing Office: Taylor Made Deep Creek Vacations & Sales

rear view of property featuring a wooden deck

$10,000 Closing Credit¹

$2,349,900

6 beds • 5.5 baths • 5,389 sqft

2463 Mayhew Inn Rd, Oakland MD 21550

Jonathan D Bell, Listing Office: Railey Realty, Inc.

view of property exterior featuring a garage

$2,434 Closing Credit¹

$205,000

3 beds • 2 baths • 2,184 sqft

405 Sunnyside Rd, Oakland MD 21550

Steve A DuBrueler, Listing Office: Coldwell Banker Premier

rear view of property featuring a lawn, ceiling fan, a wooden deck, and a patio

rear view of house with a wooden deck, ceiling fan, a patio, and a yard

living room with wood ceiling, hardwood / wood-style flooring, high vaulted ceiling, beamed ceiling, and a fireplace

3D tour

$10,000 Closing Credit¹

$1,119,000

4 beds • 2 baths • 2,230 sqft

1473 Pergin Farm Rd, Oakland MD 21550

Tony Migliaccio, Listing Office: Long & Foster Real Estate, Inc.

back of house featuring a wooden deck, a lawn, and a gazebo

sunroom featuring lofted ceiling with beams and a water view

$10,000 Closing Credit¹

$1,399,000

6 beds • 4.5 baths • 4,113 sqft

439 Paradise Hts, Oakland MD 21550

Michael N Kennedy, Listing Office: Railey Realty, Inc.

view of front facade featuring a carport and a front yard

Backup offers

$8,301 Closing Credit¹

$699,000

5 beds • 3.5 baths • 3,982 sqft

604 Harvey Winters Dr, Oakland MD 21550

Justin D Liller, Listing Office: Railey Realty, Inc.

LOT14 Warnick Way, Oakland MD, 21550 land for sale

Listing photo 2 for LOT14 Warnick Way, Oakland MD 21550

Listing photo 3 for LOT14 Warnick Way, Oakland MD 21550

$45,900

Land • 1.02 Acres

LOT14 Warnick Way, Oakland MD 21550

Terry L Boggs, Listing Office: Railey Realty, Inc.

view of front of home with a wooden deck

living room with light hardwood / wood-style flooring, wood walls, wooden ceiling, and a baseboard radiator

living room with wooden walls, wooden ceiling, ceiling fan, and crown molding

$3,858 Closing Credit¹

$324,900

2 beds • 2 baths • 560 sqft

400 Bear Dr E, Oakland MD 21550

Michael N Kennedy, Listing Office: Railey Realty, Inc.

view of dock featuring a water view and a yard

$10,000 Closing Credit¹

$1,950,000

4 beds • 3.5 baths • 5,576 sqft

2829 Shady Dell Rd, Oakland MD 21550

Jonathan D Bell, Listing Office: Railey Realty, Inc.

1 Lowes Dr, Oakland MD, 21550 land for sale

Listing photo 2 for 1 Lowes Dr, Oakland MD 21550

Listing photo 3 for 1 Lowes Dr, Oakland MD 21550

$175,000

Land • 1.60 Acres

1 Lowes Dr, Oakland MD 21550

Richard B Orr, Listing Office: Railey Realty, Inc.

$5,926 Closing Credit¹

$499,000

3 beds • 2 baths • 2,441 sqft

230 Moose Xing, Oakland MD 21550

Nick Fratz-Orr, Listing Office: Railey Realty, Inc.

$6,519 Closing Credit¹

$549,000

2 beds • 1 bath

20 Maple Del Ln, Oakland MD 21550

Michael Cumerlato, Listing Office: Jason Mitchell Group

Listing photo 2 for LOT20 Maple Del Ln, Oakland MD 21550

Listing photo 3 for LOT20 Maple Del Ln, Oakland MD 21550

$67,500

Land • 1.02 Acres

LOT20 Maple Del Ln, Oakland MD 21550

Michael Cumerlato, Listing Office: Jason Mitchell Group

bedroom with hardwood / wood-style flooring, ceiling fan, and lofted ceiling

$10,000 Closing Credit¹

$1,250,000

6 beds • 4 baths • 2,536 sqft

340 Grandview Dr, Oakland MD 21550

Michael Cumerlato, Listing Office: Jason Mitchell Group

339.03/-ACRES Baker Farm Rd, Oakland MD, 21550 land for sale

Listing photo 2 for 339.03/-ACRES Baker Farm Rd, Oakland MD 21550

Listing photo 3 for 339.03/-ACRES Baker Farm Rd, Oakland MD 21550

$1,899,900

Land • 339.03 Acres

339.03/-ACRES Baker Farm Rd, Oakland MD 21550

Kaleb M Hurley, Listing Office: Hurley Real Estate & Auctions

view of front of home featuring a wooden deck

birds eye view of property featuring a water and mountain view

$8,894 Closing Credit¹

$749,000

5 beds • 3 baths • 3,242 sqft

621 Paradise Hts, Oakland MD 21550

Nick Fratz-Orr, Listing Office: Railey Realty, Inc.

Oakland, MD Real Estate Market Overview

Browse 116 homes for sale in Oakland, MD. View properties, photos, nearby real estate with school and housing market information. Between November 2024 and December 2024, Oakland, MD real estate market has seen increase in the number of listings by 6.6%. While the average time on the market in December 2024 was 127 days, the median list price was $385,000. In December 2024 more than 1 listings in Oakland, MD were sold above the asking price. During the same period more than 2 listings were sold at asking price, while more than 12 were sold below.

From Rocket Homes Real Estate and based on county public records data

Homes for sale in Oakland, MD

Oakland, MD Real Estate Market Overview

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