MLS Listings for Sale in Oakland, MD

120 homes

Sort:

Recommended

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style. The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs, two primary bedrooms with private baths provide flexibility for family or guests. The full apartment-style basement includes its own kitchen, laundry, and heated floors, offering an inviting space for extended stays or independent living. Outdoors, a stamped concrete driveway leads to an oversized two-car ga

$865,000

4 beds4.5 baths2,970 sq ft

1909 Pysell Crosscut Rd, Oakland, MD 21550

Move-in ready • In-ground pool • Country living

(301) 387-2000

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly condo fee covers exterior, common grounds, and lakefront access. Don’t miss your chance to own premium lakefront without the price tag!

$239,900

1 bed1 bath— sq ft

565 Glendale Rd Unit 106 B, Oakland, MD 21550

Balcony doors • Tidy kitchenette • Lake views

(301) 387-2000

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel communities! Silver Tree Suites offers over 350' of pristine lakefront with western exposure. Located directly adjacent to Dutch's at Silver Tree, this location offers convenience to one of the areas most desirable restaurants, and is only 5-10 minutes to all of the local amenities and attractions you come to look for here at the lake! Established vacation rental with on site management! Want to schedule a private showing? Call today to schedule a private tour!

$175,000

1 bed1 bath382 sq ft

565 Glendale Rd Unit 210A, Oakland, MD 21550

$465 HOA • Parking • Built 2006

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180° views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive windows allowing natural light to flood the interior and provide endless vistas of the tranquil water. With over 4,000 sq ft of living space, this spacious home features soaring ceilings, rich wood finishes, and an open-concept floor plan that’s perfect for entertaining. The main level l

$1,329,000

6 beds4.5 baths4,113 sq ft

439 Paradise Hts, Oakland, MD 21550

Kathadin log home • Boat slip • Expansive deck

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lakefront living at Deep Creek Lake! This fully furnished, beautifully updated, rarely available, top-floor two-level condo features one bedroom and one bath, offering 550 square feet of comfort, charm, and versatility — perfect as a vacation home, year-round retreat, or income-producing rental. Start your mornings with exceptional sunrises from your private lakefront balcony — one of the best views in the building! Inside, you’ll find brand-new luxury vinyl plank flooring, updated lighting, and a show-stopping custom staircase, which replaced the outdated spiral design and was so substan

$289,900

1 bed1 bath550 sq ft

20160 Garrett Hwy Unit H708, Oakland, MD 21550

Custom staircase • Hot tubs • Lakefront balcony

(443) 574-1600

Property at 3898 3898 Underwood Rd, Oakland, MD 21550, 4 beds, 5 baths

$1,800,000

4 beds5 baths5,117 sq ft

3898 3898 Underwood Rd, Oakland, MD 21550

(301) 334-4876

Property at 104 Pine Top Trl, Oakland, MD 21550, 3 beds, 3.5 baths

$425,000

3 beds3.5 baths1,596 sq ft

104 Pine Top Trl, Oakland, MD 21550

(301) 387-8300

Property at 1118 Lake Shore Dr, Oakland, MD 21550, 3 beds, 2 baths

$649,000

3 beds2 baths2,446 sq ft

1118 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 355 Lonesome Pine Rd, Oakland, MD 21550, 2 beds, 2 baths

$585,000

2 beds2 baths1,584 sq ft

355 Lonesome Pine Rd, Oakland, MD 21550

(866) 525-3466

Property at 621 Paradise Hts, Oakland, MD 21550, 4 beds, 3 baths

$695,000

4 beds3 baths3,242 sq ft

621 Paradise Hts, Oakland, MD 21550

(301) 387-2000

Property at 206 Mayhew Inn Rd, Oakland, MD 21550, 1 bed, 1 bath

$229,000

1 bed1 bath— sq ft

206 Mayhew Inn Rd, Oakland, MD 21550

(301) 387-4700

Property at 163 Crestview Dr, Oakland, MD 21550, 3 beds, 2.5 baths

$325,000

3 beds2.5 baths1,416 sq ft

163 Crestview Dr, Oakland, MD 21550

(301) 387-2000

Property at 531 Glendale Rd Unit B302, Oakland, MD 21550, 2 beds, 1 bath

$369,000

2 beds1 bath887 sq ft

531 Glendale Rd Unit B302, Oakland, MD 21550

(301) 387-2000

Property at 565 Glendale Rd #312, Oakland, MD 21550, 1 bed, 1 bath

$229,000

1 bed1 bath785 sq ft

565 Glendale Rd #312, Oakland, MD 21550

(888) 860-7369

Property at 328 Stool Rock Rd, Oakland, MD 21550, 4 beds, 2.5 baths

$545,000

4 beds2.5 baths1,860 sq ft

328 Stool Rock Rd, Oakland, MD 21550

(301) 387-2000

Property at 139 Overlook Ridge Dr, Oakland, MD 21550, 5 beds, 4.5 baths

$875,000

5 beds4.5 baths2,846 sq ft

139 Overlook Ridge Dr, Oakland, MD 21550

(301) 387-4700

Property at 127 Paradise Hts, Oakland, MD 21550, 3 beds, 2.5 baths

$1,100,000

3 beds2.5 baths2,240 sq ft

127 Paradise Hts, Oakland, MD 21550

(301) 387-4700

Property at 565 Glendale Rd #116, Oakland, MD 21550, 1 bed, 1 bath

$169,000

1 bed1 bath484 sq ft

565 Glendale Rd #116, Oakland, MD 21550

(301) 387-2000

Property at 41 Boyd Paugh Ln, Oakland, MD 21550, 7 beds, 5 baths

$2,399,000

7 beds5 baths4,691 sq ft

41 Boyd Paugh Ln, Oakland, MD 21550

(301) 387-2000

Property at 315 Coolidge Ave, Oakland, MD 21550, 3 beds, 2 baths

$269,500

3 beds2 baths1,600 sq ft

315 Coolidge Ave, Oakland, MD 21550

(301) 387-4700

Property at 723 Kings, Oakland, MD 21550, 4 beds, 2.5 baths

$380,000

4 beds2.5 baths1,824 sq ft

723 Kings, Oakland, MD 21550

(301) 722-4700

Property at 611 E Oak St, Oakland, MD 21550, 5 beds, 3 baths

$295,000

5 beds3 baths1,800 sq ft

611 E Oak St, Oakland, MD 21550

(301) 387-2000

Property at 565 Glendale Rd #212, Oakland, MD 21550, 1 bed, 1 bath

$210,000

1 bed1 bath527 sq ft

565 Glendale Rd #212, Oakland, MD 21550

(301) 387-2000

Property at 433 San Francisco St, Oakland, MD 21550, 6 beds, 2.5 baths

$599,900

6 beds2.5 baths2,560 sq ft

433 San Francisco St, Oakland, MD 21550

(301) 387-2000

Property at LOT 2 Beaver Run Rd, Oakland, MD 21550

$3,500

— beds— baths— sq ft

LOT 2 Beaver Run Rd, Oakland, MD 21550

(301) 387-4700

Property at Garrett Trl, 16, Mountain Lake Park, MD 21550

$29,900

— beds— baths— sq ft

Garrett Trl, 16, Mountain Lake Park, MD 21550

(301) 387-8300

Property at 125 N 2nd, Oakland, MD 21550

$115,000

— beds— baths— sq ft

125 N 2nd, Oakland, MD 21550

(301) 387-2000

Property at 000 Coffee Pot Rd, Gypsum, CO 81637

$14,000,000

— beds— baths— sq ft

000 Coffee Pot Rd, Gypsum, CO 81637

Property at 3257 George Washington Hwy, Oakland, MD 21550

$280,000

— beds— baths— sq ft

3257 George Washington Hwy, Oakland, MD 21550

(301) 387-2000

Property at Lot 40 Big Piney Dr, Oakland, MD 21550

$17,000

— beds— baths— sq ft

Lot 40 Big Piney Dr, Oakland, MD 21550

(301) 387-4700

Property at Lots 13/17 Dogwood Dr, Oakland, MD 21550

$32,000

— beds— baths— sq ft

Lots 13/17 Dogwood Dr, Oakland, MD 21550

(301) 387-2000

Property at 170 San Francisco St, Oakland, MD 21550

$129,900

— beds— baths— sq ft

170 San Francisco St, Oakland, MD 21550

(717) 757-2717

Property at 123 Mountainview Ct, Oakland, MD 21550

$221,000

— beds— baths— sq ft

123 Mountainview Ct, Oakland, MD 21550

(301) 387-2000

Property at 0 Lake Shore Dr, Oakland, MD 21550

$248,500

— beds— baths— sq ft

0 Lake Shore Dr, Oakland, MD 21550

(304) 788-5540

Property at Lot 18 Laurel Ct, Oakland, MD 21550

$95,000

— beds— baths— sq ft

Lot 18 Laurel Ct, Oakland, MD 21550

(301) 387-2000

Property at Fox Tail Rd, Oakland, MD 21550

$39,500

— beds— baths— sq ft

Fox Tail Rd, Oakland, MD 21550

(301) 387-2000

Property at Mayhew Inn Rd, Oakland, MD 21550

$120,000

— beds— baths— sq ft

Mayhew Inn Rd, Oakland, MD 21550

(301) 387-2000

Property at 3.35 acres </> 4th St, Oakland, MD 21550

$150,000

— beds— baths— sq ft

3.35 acres </> 4th St, Oakland, MD 21550

(301) 259-1119

Property at Santa Fe Trl, 14, West Oakland, MD 21550

$30,000

— beds— baths— sq ft

Santa Fe Trl, 14, West Oakland, MD 21550

(410) 823-0033

Property at LOT 25 Holy Cross Dr, Oakland, MD 21550

$499,999

— beds— baths— sq ft

LOT 25 Holy Cross Dr, Oakland, MD 21550

(301) 387-2000

Property at 9 Timber Falls Rd, Oakland, MD 21550

$34,000

— beds— baths— sq ft

9 Timber Falls Rd, Oakland, MD 21550

(301) 387-2000

Viewing page 2 of 3

MLS Listings for Sale in Oakland

There are currently 120 mls listings for sale in Oakland at a median listing price of $417K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oakland stay on the market for 138 days. This map is refreshed with the newest listings in Oakland every 15 minutes.

In the past month, 3 homes have been sold in Oakland. In addition to houses in Oakland, there was also 1 condo, 1 townhouse, and 1 multi-family unit for sale in Oakland last month. Find your dream home in Oakland using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Oakland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oakland. Our Oakland real estate stats and trends will give you more information about home buying and selling trends in Oakland. If you're looking to sell your home in the Oakland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oakland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Oakland, MD

More to explore in Oakland, MD

Featured
Bedroom

How to buy a house in Oakland, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

MLS Listings for Sale in Oakland, MD

MLS Listings for Sale in Oakland

More real estate resources for Oakland, MD

Nearby Cities

Zip Codes

Nearby Cities with MLS Listings

More to explore in Oakland, MD

How to buy a house in Oakland, MD

Popular Markets in Maryland