Homes with Pools for Sale in Oakland, MD

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ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
"RANCHER WITH IN GROUND POOL" Well maintained Cedar Siding Rancher on large level lot with 3 bedrooms, 1 1/2 baths, beautiful hardwood floors on main level, Living room with wood burning brick fireplace, Large eat-in-kitchen/ dining area, with door that leads to deck overlooking in ground pool! Fenced yard and huge shed/pool storage, lower level finished great room for family entertaining with cozy wood stove which will be great for chilly days. New roof, hot water heater, cedar just stained/sealed! AND NEW DRIVEWAY 10/2026 COST WAS $8K - Come take a look!

$285,000

3 beds1.5 baths1,984 sq ft

216 N 12th St, Oakland, MD 21550

Fenced yard • Finished great room • Huge shed

(410) 879-8080

ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
Get ready to relax & enjoy Deep Creek Lake at your 5 BR 5 Bath home offering a wooded level setting with the lake and dock slip right out in front of you. Located in the area's premiere community, Blakeslee, you'll appreciate the inviting open floor plan featuring two living areas, 5 suites with direct bath access, direct access to a large deck, covered porch or relax in the comfy screened porch. The outdoor area also offers a fire pit and room for outdoor games. Beautifully and tastefully decorated, the atmosphere within and without is perfect regardless of season. The home has had over 30 meaningful updates including bathroom remodels and major mechanical improvements allowing you t

$2,100,000

5 beds5.5 baths4,074 sq ft

1038 S Blakeslee Rd, Oakland, MD 21550

Covered porch • Screened porch • Fire pit

(301) 387-2000

ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy. Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and expansive windows that fill the home with natural light while showcasing the serene surroundings. The beautifully updated kitchen is designed for gathering, featuring granite countertops, abundant cabinetry, stainless steel appliances, and a spacious island that flows seamlessly into the dining and living a

$859,000

6 beds4.5 baths5,547 sq ft

17240 Garrett Hwy, Oakland, MD 21550

Open floor plan • Expansive windows • Updated kitchen

(301) 387-2000

ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a new water heater and sink, an upgraded electrical panel, and premium cement-backed luxury vinyl plank flooring for ultimate durability. Stunning new shiplap ceilings with recessed lighting illuminate the freshly painted main living spaces, complete with a cozy wood-burning fireplace. Includes an assi

$550,000

2 beds2 baths1,340 sq ft

193 Red Run Rd Unit 1-B-3, Oakland, MD 21550

Lakefront living • Soft-close cabinetry • Granite countertops

(301) 698-5005

ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
Experience exceptional lakefront living in this spectacular eight-bedroom estate designed for unforgettable gatherings and year-round enjoyment. Perfectly positioned on an oversized lakefront lot with 116’ LF, this remarkable home offers easy access to the water via a walking path, and the abundance of windows fill the interior with natural light. At the heart of the home is a magnificent great room with soaring ceilings, creating an impressive space for entertaining family and friends. The gourmet kitchen is a chef's dream, featuring premium finishes, generous prep space, and abundant cabinetry, making it as functional as it is beautiful. Boasting an indoor sparkling pool and sauna

$3,950,000

8 beds9 baths6,486 sq ft

1131 Lake Shore Dr, Oakland, MD 21550

Lakefront lot • Outdoor living areas • Gourmet kitchen

(301) 387-4700

Property at 20160 Garrett Hwy Unit H706, Oakland, MD 21550, 1 bed, 1 bath

$299,000

1 bed1 bath550 sq ft

20160 Garrett Hwy Unit H706, Oakland, MD 21550

(301) 387-4700

Property at 20160 Garrett Hwy Unit C307, Oakland, MD 21550, 1 bed, 1 bath

$379,500

1 bed1 bath636 sq ft

20160 Garrett Hwy Unit C307, Oakland, MD 21550

(301) 387-2000

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NEW 16 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
Ultimate Ski-In/Ski-Out Mountain Retreat at Wisp Resort! Experience the best of four-season mountain living from this exceptional 8-bedroom, 6-bathroom retreat perched at the top of Ace’s Run on the North Camp side of Wisp Resort. Offering true ski-in/ski-out access, this impressive property combines an unbeatable slope-side location with resort-style amenities designed for unforgettable gatherings and year-round enjoyment. The private indoor pool provides endless entertainment regardless of the season, while two outdoor hot tubs offer the perfect place to unwind after a day on the slopes. Gather around the outdoor fire pit for evenings under the stars and enjoy the mountain setting t

$1,899,000

8 beds6 baths5,768 sq ft

66 Ridge Run Rd, Mc Henry, MD 21541

Slope-side location • Outdoor fire pit • Outdoor hot tubs

(301) 387-2000

OPEN SUN, 10AM TO 12PM

ABOUT THIS HOME
Home with a Pool for sale in Oakland, WV:
Make Big Bear Lake your year-round retreat! Situated on just over 2 acres, this well-maintained and updated 3-bedroom, 2-bath home offers room to relax inside and out. A recently added bonus room provides extra space to unwind, while the wood-burning stove keeps things cozy on chilly evenings. Outside, gather around the custom fire pit or put the heated, detached 1-car garage to work—with a built-in air compressor included! Multiple storage buildings offer plenty of space for tools, equipment, and outdoor gear. Enjoy the privacy, space, and comfort of your own Big Bear Lake getaway. Schedule your tour today!

$229,000

3 beds2 baths1,879 sq ft

134 Endicott St, Bruceton Mills, WV 26525

Wood-burning stove • Bonus room • 2 acres

ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
Welcome to 431 Mountaintop Road at Deep Creek Lake! This 5 bedroom, 3.5 bathroom mountain retreat offers over 3200 square feet of finished living space on 3 levels. The Deep Creek Highlands community offers premium amenities including lake access, tennis courts, outdoor pool in the summer seasons and walking trails to a scenic overlook. This home offers a main level bedroom with en-suite bathroom provides layout functionality and convenience, two gas fireplaces for warmth and ambiance in the winter months, a four-seasons screened-in room, paved driveway and a private, mountain feel. New roof and completely repainted interior in 2025! Call today to schedule private tour of this excellent mou

$949,000

5 beds3.5 baths3,285 sq ft

431 Mountaintop Rd, Mc Henry, MD 21541

Outdoor pool • Main level bedroom • Scenic overlook

(301) 387-2000

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Oakland, WV:
Welcome to * Alpine Lake Resort * This lovely 3-4 bedroom, 3 full bath home in a peaceful lake community has everything you need! A brand-new roof and gutter guards were just added on September 14th, 2026. You’ll appreciate the concrete driveway, beautiful hardwood floors, and a large 2-car attached garage. Thoughtfully designed with room for everyone to relax and enjoy. The primary bedroom features a convenient attached bath, while the generous living spaces provide plenty of room for guests, and everyday living. A comfortable home with space to spread out and make your own! The level, wooded lot gives you plenty of privacy and a touch of nature. Plus, the updated appliances make c

$324,700

3 beds3 baths1,797 sq ft

1002 Goldenrod Dr, Terra Alta, WV 26764

Updated appliances • Brand new roof • Level wooded lot

ABOUT THIS HOME
Home with a Pool for sale in Oakland, MD:
Enjoy direct views of Squirrel Cage from this desirable unit at The Lodges at Wisp, located in the “Village Inn” section! This property offers an excellent opportunity for a mountain getaway, with rental opportunities available through the on-site rental pool. An added owner benefit is that there are no condo fees while the unit remains in the rental pool, providing an attractive ownership advantage. Owners also enjoy ski and golf privileges, making it easy to take advantage of everything Wisp Resort has to offer. With skiing and snow sports in the winter and golf, hiking, boating, and other outdoor activities throughout the warmer months, this unit offers true year-round appeal

$52,500

1 bed1 bath356 sq ft

290 Marsh Hill Rd Unit 305C, Mchenry, MD 21541

No condo fees • $836 HOA • Parking

(301) 387-2000

ABOUT THIS HOME
Home with a Pool for sale in Oakland, WV:
LAKE VIEWS! Who doesn’t want a lake view? This lakeside home, located within the Alpine Lake HOA community, is being sold COMPLETELY FURNISHED (minus one chair), so you can start enjoying it right away! Located approximately 70 yards from the water, this home features a furnace system installed in 2022, smart appliances, an electric fireplace, and USB-equipped leather sofas—all included! Step outside and stroll through the beautiful pine patch in front of the home to access the 7-Bridges hiking trail and the stocked 150-acre Alpine Lake. And there’s even more to enjoy! Alpine Lake offers kayaking, pickleball, an 18-hole golf course, hiking trails, lake activities, and plen

$250,000

3 beds1 bath1,056 sq ft

714 Bluebell, Terra Alta, WV 26764

Lakeside home • Smart appliances • Lake views

Property at 17 Goldfinch, Terra Alta, WV 26764, 3 beds, 3.5 baths

$457,700

3 beds3.5 baths2,800 sq ft

17 Goldfinch, Terra Alta, WV 26764

Property at 264 Primrose, Terra Alta, WV 26764, 2 beds, 2.5 baths

$267,400

2 beds2.5 baths1,780 sq ft

264 Primrose, Terra Alta, WV 26764

Property at 5847 Bittinger Rd, Swanton, MD 21561, 3 beds, 3 baths

$525,000

3 beds3 baths1,344 sq ft

5847 Bittinger Rd, Swanton, MD 21561

(301) 387-2000

Property at 221 Anemone, Terra Alta, WV 26764, 3 beds, 2 baths

$349,000

3 beds2 baths1,790 sq ft

221 Anemone, Terra Alta, WV 26764

Property at 596 Hemlock Cir, Terra Alta, WV 26764, 2 beds, 2 baths

$275,000

2 beds2 baths1,258 sq ft

596 Hemlock Cir, Terra Alta, WV 26764

Property at 290 Marsh Hill Rd Unit 222A, Oakland, MD 21541, 1 bed, 1 bath

$49,900

1 bed1 bath— sq ft

290 Marsh Hill Rd Unit 222A, Oakland, MD 21541

(301) 387-2000

Property at 644 Pine Dr, Terra Alta, WV 26764, 2 beds, 2 baths

$307,700

2 beds2 baths1,215 sq ft

644 Pine Dr, Terra Alta, WV 26764

Property at 485 Redwood Dr, Terra Alta, WV 26764, 3 beds, 2 baths

$344,000

3 beds2 baths2,200 sq ft

485 Redwood Dr, Terra Alta, WV 26764

(301) 259-1119

Property at 14 Stilwater Dr, Swanton, MD 21561, 8 beds, 8.5 baths

$3,299,900

8 beds8.5 baths8,442 sq ft

14 Stilwater Dr, Swanton, MD 21561

(301) 387-2000

Property at 290 Marsh Hill Rd #706, Mchenry, MD 21541, 2 beds, 1 bath

$54,900

2 beds1 bath450 sq ft

290 Marsh Hill Rd #706, Mchenry, MD 21541

(301) 387-2000

Property at 49 Greenstone Way, Mc Henry, MD 21541, 6 beds, 7 baths

$1,799,900

6 beds7 baths4,477 sq ft

49 Greenstone Way, Mc Henry, MD 21541

(301) 387-2000

Property at 230 Rock Lodge Rd, Mc Henry, MD 21541, 5 beds, 6.5 baths

$5,250,000

5 beds6.5 baths8,342 sq ft

230 Rock Lodge Rd, Mc Henry, MD 21541

(443) 574-1600

Property at 888 E Alpine Dr, Terra Alta, WV 26764, 4 beds, 2 baths

$499,000

4 beds2 baths2,716 sq ft

888 E Alpine Dr, Terra Alta, WV 26764

Property at 134 Day Lily Ct, Terra Alta, WV 26764, 3 beds, 2.5 baths

$425,000

3 beds2.5 baths1,936 sq ft

134 Day Lily Ct, Terra Alta, WV 26764

Homes with Pools for Sale in Oakland

There are currently 7 homes with pools for sale in Oakland at a median listing price of $312K. 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 134 days. This map is refreshed with the newest listings in Oakland every 15 minutes.

In the past month, 4 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.

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