Luxury homes for sale & real estate in Oakland, MD

17 homes

Sort:

Recommended

COMING SOON

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The View, this custom home offers stunning lake views in a serene, private setting. Centrally located less than 4 miles from Wisp while backing up to hundreds of acres of untouched forest, this property truly offers the best that Deep Creek Lake has to offer. This luxury home has been impeccably maintained as a second home, and has never been used as a rental property. No expense has been spared as this home boasts four master suites, two gas fireplaces, a saltwater hot tub with lake views, 10' ceilings throughout, and a newly built, 2,000 square foot custom composite deck complete with an underdeck draina

$1,199,990

4 beds5 baths4,744 sq ft

444 Woodlands Hill Ln, Oakland, MD 21550

2.02 acre lot • 2 garage spots • Built 2007

(240) 219-2422

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with a sprawling island, Wolf range, and access to a four-season room that opens fully to the outdoors through custom bi-fold doors. The main-level primary suite spans nearly 900 sq ft with a private balcony, soaking tub, his-and-her vanities, and a massive walk-in closet. Enjoy five fireplaces, an indoo

$6,499,900

8 beds8.5 baths11,417 sq ft

47 Holy Cross, Oakland, MD 21550

Lakefront living • Four season room • Primary suite

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Lake Access property overlooking Cherry Creek Cove in the coveted Mountainside community, at 2,536 square feet, this fully furnished retreat pairs modern comfort with timeless mountain style. Freshly updated from top to bottom, with a new roof and deck staining, every detail feels dialed in. A wall of glass and open layout connects bright gathering spaces with panoramic lake views that steal the show. Stone fireplaces, warm wood accents, and clean finishes create a space that feels both grounded while perched on high. Six bedrooms and four full baths offer room for family, friends, or guests. The lower-level walkout is made for game nights and slow mornings by the fire. Outside, a sprawling

$949,900

6 beds4 baths2,536 sq ft

340 Grandview Dr, Oakland, MD 21550

Private acres • Hot tub • Sprawling deck

(301) 387-2000

NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Discover The Birch Bower, a rare architect-designed lakefront sanctuary offering 600 feet of private shoreline on Deep Creek Lake. Completed in 2021, this 6-bedroom, 5.5-bath residence exemplifies modern luxury, combining meticulous design, serene natural surroundings, and proven short-term rental performance. Offered turn-key and fully furnished, this extraordinary lakefront estate presents a unique opportunity for discerning buyers seeking a distinguished and enduring retreat on Deep Creek Lake. Set on 0.39 acres with an adjoining 1.5± acre buffer strip, the property affords unparalleled privacy and ecological significance, with protected forest supporting endangered native species

$4,200,000

6 beds5.5 baths4,354 sq ft

282 Mccomas Beach Ter, Oakland, MD 21550

0.39 acre lot • 15 parking spots • Built 2021

(703) 443-1757

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Architecturally unique, private and spacious lakefront home with a perfect central location! Step into a home that blends striking architectural design with the best of lake living. The living room showcases a dramatic wall of glass and a floor-to-ceiling stone fireplace, while a large glass-walled rec room on the lower level offers another light-filled space to relax or entertain. This 5-bedroom, 3-bath residence includes a spacious private primary suite with its own balcony, plus a main level bedroom, and three lower-level bedrooms, two overlooking the lake! Multiple decks, and a hot tub with a peaceful water view backdrop. Enjoy the rare combination of being centrally located yet tucked

$1,499,000

5 beds3 baths2,826 sq ft

336 Paradise Hts, Oakland, MD 21550

Private balcony • Architectural design • Wall of glass

(301) 387-2000

Property at 1010 Holy Cross Dr, Oakland, MD 21550, 8 beds, 8.5 baths

$5,150,000

8 beds8.5 baths10,300 sq ft

1010 Holy Cross Dr, Oakland, MD 21550

(301) 387-2000

Property at 2311 Boy Scout Rd, Oakland, MD 21550, 4 beds, 3 baths

$1,699,900

4 beds3 baths3,517 sq ft

2311 Boy Scout Rd, Oakland, MD 21550

(301) 387-2000

Property at 39 Leo Friend Rd, Oakland, MD 21550, 3 beds, 3.5 baths

$950,000

3 beds3.5 baths3,897 sq ft

39 Leo Friend Rd, Oakland, MD 21550

(301) 259-1119

Property at 1909 Pysell Crosscut Rd, Oakland, MD 21550, 4 beds, 4.5 baths

$865,000

4 beds4.5 baths2,970 sq ft

1909 Pysell Crosscut Rd, Oakland, MD 21550

(301) 387-2000

Property at 439 Paradise Hts, Oakland, MD 21550, 6 beds, 4.5 baths

$1,329,000

6 beds4.5 baths4,113 sq ft

439 Paradise Hts, Oakland, MD 21550

(301) 387-2000

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 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 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 415 Nazelrod Rd, Oakland, MD 21550, 4 beds, 5 baths

$3,249,000

4 beds5 baths6,036 sq ft

415 Nazelrod Rd, Oakland, MD 21550

(301) 387-2000

Property at 1240 Boy Scout Rd, Oakland, MD 21550, 7 beds, 6 baths

$4,390,000

7 beds6 baths5,695 sq ft

1240 Boy Scout Rd, Oakland, MD 21550

(443) 574-1600

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 000 Coffee Pot Rd, Gypsum, CO 81637

$14,000,000

— beds— baths— sq ft

000 Coffee Pot Rd, Gypsum, CO 81637

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Experience luxury mountain living at its finest in this brand new construction, slope-front masterpiece at Wisp Resort in Deep Creek Lake! Perfectly positioned steps from the ski slope and Chair Lift 7 in North Camp, this extraordinary 8-bedroom, 7 full bath, 2 half bath home offers true ski-in/ski-out access and an impressive array of high-end features—complete with its own indoor pool, expansive slope and mountain views, and exceptional rental potential, with projections reaching up to $193K in annual owner gross rent. The main level welcomes you with a grand living room showcasing soaring vaulted ceilings, a striking stone fireplace, and large windows framing expansive views of the

$2,099,000

8 beds8 baths5,564 sq ft

353 Lower Camp Rd, Mc Henry, MD 21541

Gourmet kitchen • Media theatre room • Indoor pool

(301) 387-2000

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Luxury cedar chalet in the heart of Deep Creek Lake. This custom lodge sits beside the ASCI whitewater course, placing you in the center of Garrett county’s year-round outdoor scene and just minutes from local shops and restaurants. The community trail gives direct access to Wisp on one side, and Fork Run’s 550-acre nature preserve on the other. Finished in 2022, the home was crafted for open-concept living with two full stories of light and space. Vaulted ceilings and a wall of glass on the chalet’s prow pull in the mountain setting and set the tone the moment you walk in. Two large primary suites and four spacious en-suites, make the layout ideal for multiple families. H

$1,599,900

6 beds6.5 baths4,484 sq ft

110 Wisp Adventure Rd, Mc Henry, MD 21541

Cedar chalet • Wall of glass • Vaulted ceilings

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
This striking 5 bed/7 bath log home sits in one of Wisp Mountain’s most sought-after locations, offering a warm four-season retreat just minutes from Deep Creek Lake, Lodestone Golf Course, Wisp Resort, and the area’s top dining and recreation. Seasonal lake views from the living room and deck enhance the setting and connect the home to its surroundings. The main level features a bright, open layout with a wall of windows, a floor-to-ceiling stone fireplace, and a well-equipped kitchen with granite, stainless appliances, gas range, farm sink, and a large island. Sliding doors extend the space onto an expansive deck with a covered outdoor fireplace, making indoor-outdoor entertai

$1,395,000

5 beds6 baths4,416 sq ft

19 Greenside Ct, Mc Henry, MD 21541

0.65 acre lot • 2 garage spots • Built 2021

(301) 387-2000

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Lake access! Lake views! One of a kind Custom 4 bedroom Log home built with 18” logs, large antler chandelier, custom cedar spiral stairs, indoor and outdoor fireplaces, large deck and covered patio area. This is a one of a kind property and must be seen in person to appreciate! Wow, this striking four-bedroom residence stands out as one of the most distinctive homes on Deep Creek Lake. The main level features a gourmet kitchen with professional-grade stainless steel appliances and granite countertops, complemented by a spacious living room and a cozy family room centered around a wood-burning stove. Step outside onto the expansive 22' x 13' deck to enjoy panoramic lake views. Upstair

$969,000

4 beds2 baths— sq ft

211 Highwood Dr, Mc Henry, MD 21541

Cedar spiral stairs • Custom log home • Indoor fireplaces

(301) 259-1119

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
Discover the perfect mountain retreat just a short walk from beautiful Deep Creek Lake. This quintessential cabin sits on 53 private acres bordering the 1,800 acre Deep Creek Lake State Park, offering direct access to endless outdoor recreation-fishing, swimming, boating, hiking, and more. Inside, you’ll find a spacious living/gathering room featuring a stunning floor-to-ceiling stone fireplace, perfect for cozy evenings after a day on the trails. The main level includes a comfortable bedroom, full bath, and a kitchen with plenty of space for family and guests. The upper level features a large bedroom with built-in bunk beds and an open loft area, providing extra sleeping and lounge

$1,200,000

2 beds1 bath1,581 sq ft

725 Candle Tree Ln, Swanton, MD 21561

Private acres • Direct access • Mature timber

(301) 259-1119

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Oakland, MD:
This stunning lakefront residence is a true masterpiece on the shores of Deep Creek Lake — where design, nature, and craftsmanship converge. Completely reimagined and luxuriously curated with Restoration Hardware furnishings, fixtures, and décor throughout, it offers a seamless blend of modern sophistication and timeless mountain warmth. With unobstructed, year-round views of Deep Creek Lake and the surrounding mountains, the scenery is nothing short of breathtaking. The home’s expansive wall of glass brings the lake to your doorstep, with nearly every room offering a front-row view of the water’s edge. The open main-level layout provides effortless living, featurin

$4,790,000

6 beds6.5 baths4,570 sq ft

3135 Turkey Nck, Swanton, MD 21561

Lakefront residence • Gourmet kitchen • Unobstructed views

(301) 387-2000

Property at 1321 Marsh Hill Rd, Mc Henry, MD 21541, 3 beds, 2 baths

$1,200,000

3 beds2 baths1,512 sq ft

1321 Marsh Hill Rd, Mc Henry, MD 21541

(301) 387-4700

Property at 48 Stone Tavern Ln #2, Mchenry, MD 21541, 3 beds, 2 baths

$969,000

3 beds2 baths1,370 sq ft

48 Stone Tavern Ln #2, Mchenry, MD 21541

(301) 387-2000

Property at 152 Ridge Run Rd, Mc Henry, MD 21541, 6 beds, 5.5 baths

$1,799,900

6 beds5.5 baths4,044 sq ft

152 Ridge Run Rd, Mc Henry, MD 21541

(301) 387-2000

Property at 294 N Shoreline Dr, Swanton, MD 21561, 5 beds, 4.5 baths

$2,089,000

5 beds4.5 baths3,980 sq ft

294 N Shoreline Dr, Swanton, MD 21561

(301) 387-4700

Property at 142 Ridge Run Rd, Mc Henry, MD 21541, 6 beds, 6.5 baths

$2,199,000

6 beds6.5 baths5,494 sq ft

142 Ridge Run Rd, Mc Henry, MD 21541

(703) 242-0005

Property at 120 Rock Lodge Rd, Mc Henry, MD 21541, 3 beds, 2 baths

$919,000

3 beds2 baths1,269 sq ft

120 Rock Lodge Rd, Mc Henry, MD 21541

(301) 259-1119

Property at 16 Grand Estates Dr, Mc Henry, MD 21541, 7 beds, 7 baths

$1,999,900

7 beds7 baths4,758 sq ft

16 Grand Estates Dr, Mc Henry, MD 21541

(301) 387-2000

Property at 34 Shingle Camp Ter, Mc Henry, MD 21541, 3 beds, 1 bath

$1,200,000

3 beds1 bath1,568 sq ft

34 Shingle Camp Ter, Mc Henry, MD 21541

(301) 387-4700

Property at 495 White Oak Dr, Swanton, MD 21561, 3 beds, 2 baths

$875,000

3 beds2 baths2,448 sq ft

495 White Oak Dr, Swanton, MD 21561

(301) 387-4700

Property at 723 Pinnacle Dr, Swanton, MD 21561, 5 beds, 5 baths

$974,900

5 beds5 baths3,716 sq ft

723 Pinnacle Dr, Swanton, MD 21561

(703) 378-8810

Property at 25 Cedar Shores Dr, Mc Henry, MD 21541, 6 beds, 5 baths

$4,250,000

6 beds5 baths6,120 sq ft

25 Cedar Shores Dr, Mc Henry, MD 21541

(301) 387-2000

Property at 82 Landmark Dr #4, Mc Henry, MD 21541, 4 beds, 4 baths

$999,000

4 beds4 baths3,083 sq ft

82 Landmark Dr #4, Mc Henry, MD 21541

(301) 387-2000

Property at 699 Harveys Peninsula Rd, Swanton, MD 21561, 3 beds, 2 baths

$899,000

3 beds2 baths1,176 sq ft

699 Harveys Peninsula Rd, Swanton, MD 21561

(301) 387-4700

Property at Lot 12, Phase 4 Marsh Hill Rd, Mchenry, MD 21541

$949,000

— beds— baths— sq ft

Lot 12, Phase 4 Marsh Hill Rd, Mchenry, MD 21541

(301) 387-4700

Luxury Homes for Sale in Oakland

There are currently 17 luxury homes for sale in Oakland at a median listing price of $440K. 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 149 days. This map is refreshed with the newest listings in Oakland every 15 minutes.

In the past month, 5 homes have been sold in Oakland. In addition to houses in Oakland, there was also 1 condo, 3 townhouses, 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

Nearby Cities

Zip Codes

21550 homes for sale

Nearby Cities with Luxury Homes

More to explore in Oakland, MD

Featured
Price

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.