Stilwater, Oakland, MD Real Estate Search

Stilwater, Oakland, MD Waterfront Homes for Sale

Our website features the best real estate search for waterfront homes available in Stilwater, Oakland, MD and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Stilwater, Oakland, MD real estate market? Sign up for a  Stilwater, Oakland, MD Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Stilwater, Oakland, MD Waterfront Homes for Sale

$2,925,000
4 Beds 4 Baths
A rare opportunity to own a lakefront property in the Blakeslee. Located in one of best coves and communities on Deep Creek Lake, the 4 bedroom, 3.5 bath property offers the perfect home and lot package for the best in lakefront living. The 1+ acre wooded property with 150' of premium frontage was the first building site purchased when the development opened . The gently sloping wooded sunset facing lot provides easy access to the lake and dock areas. The current owners have added multiple landscape upgrades including paver stone walkways along with lakeside picnic and fire pit areas. A paved circular driveway provides easy year round access from the street. With lake and summer sunset views from nearly every room, the well designed home offers an open floor plan featuring plenty of window coverage. The main level offers a recently upgraded kitchen and lake facing eating area. A large lake facing great room with fireplace adjoins a cozy family room with its own fireplace and direct deck access. The recently added primary bedroom suite includes a spacious bedroom, luxurious bath, 2 walk in closets and a bonus room currently used as an office. The second floor includes a second primary suite and two spacious bedrooms along with a loft. There is also a lower level with a room that could be a game and or work out area. Many would consider the recently added lakeside covered porch with impressive wood fireplace their favorite spot. It offers direct access to the new deck and primary suite. The property also offers an attached 2 car garage and a detached 24 x 24 garage with plenty of interior height for boat and or tall vehicle storage. Additional upgrades and features includes the addition of a detached 2 car garage, complete deck replacement, whole house generator, replacement and updated HVAC and security systems. The roof shingles have also been recently replaced . Blakeslee is considered by many to be the finest community in the Deep Creek Lake area. The developers believed quality was more important than quantity and designed a community with great amenities and over 100 acres of open space that is restricted from additional development. Blakeslee has also attracted a healthy mixture of full time and vacation owners. The self managed community offers many unique amenities. These amenities include a community center with indoor heated pool, locker rooms, kitchen and decking. Two tennis courts along with a basketball and pickleball courts are well maintained . A multipurpose field is available for outdoor games. A trail system runs through the wooded areas for area residents. Other important features include a storage areas for boats and trailers along with a dedicated trash removal area. It all adds up to a a great opportunity to experience all the benefits that home ownership in the Deep Creek Lake area has to offer. Schedule your showing today as homes for sale in this community typically don't last long.

255 Thornberry Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$379,500
1 Beds 1 Baths
Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then spend the day enjoying the incredible amenities that make Will O' The Wisp one of Deep Creek Lake's most sought-after destinations. Residents and guests have access to an indoor swimming pool and hot tub, racquetball court, fitness center, and arcade, providing year-round entertainment for all ages. RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. DURING INCLEMENT WEATHER CONDITIONS, PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ASSOCIATED WITH OR BY WEATHER AT THE PROPERTY. Boating enthusiasts will appreciate the community's 22 dock slips available for reservation and 4 dedicated jet ski docks, making it easy to get out and enjoy the lake. When it's time to relax, take advantage of two exceptional waterfront restaurant and bar venues located on-site, both featuring stunning lake views and convenient commercial docking. With professional on-site management, resort-style amenities, and a premier lakefront location just minutes from Wisp Resort, state parks, golf courses, and countless outdoor activities, this property offers an incredible opportunity to own a piece of Deep Creek Lake's waterfront lifestyle. Whether you're looking for a weekend escape or a property with strong rental appeal, this lakeview condo checks all the boxes.

20160 Garrett Hwy Unit #C307, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$875,000
3 Beds 4 Baths
Stunning split lakefront retreat with sweeping views and Type-A dock. Experience exceptional lake life in this beautifully maintained one owner home offering breathtaking lake views and timeless craftsmanship in a serene landscaped setting. This impressive 3 bedroom 3.5 bathroom residence welcomes you through an elegant foyer with soaring cathedral ceilings and a striking oak staircase that sets the tone for the home’s warm refined character. Nearly 4,000 sq ft of thoughtfully designed living space is wrapped in a classic stone exterior that blends seamlessly into its natural surroundings. The main living area offers a cozy yet grand atmosphere with a stunning stone fireplace perfect for crisp mountain evenings while the adjoining dining area opens through sliding glass doors to a charming patio ideal for entertaining or simply enjoying the peaceful lake backdrop. The lower level is built for gathering and entertaining, featuring a spacious recreation room with a rustic stone wet bar. A generous 13 x 16 den currently used as a 4th bedroom adds flexible living space for guests or hobbies. Outdoor living shines just as brightly with a welcoming front patio offering another peaceful advantage to take in the lake views while just across the street you’ll find your private dock area complete with storage shed firepit and Type A dock providing effortless access to the water and endless opportunities for lakeside enjoyment. Blending comfort space and true lake living this exceptional property is the perfect retreat for making lasting memories. Schedule your showing today!

39 Leo Friend Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

$575,000
3 Beds 2 Baths
With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace, queen sleeper sofa, high top table with stools and a breathtaking balcony. Just up the stairs, enjoy the king bed in a loft bedroom that overlooks the living room and towering two-story window facing Deep Creek Lake! Also on this level is another bedroom with a Queen bed that shares a hallway bathroom with luxury finishes and a walk-in shower. On the top level you will enjoy even more space and accommodations. The 7th floor level has an additional hallway entrance for more privacy. Relax in the King bed and look out to your private balcony with gorgeous lake views. This space also features a well appointed luxury bathroom with walk-in shower and double bowl sinks. An additional mini-fridge and Keurig coffee maker provide easy access if you don't want to go downstairs. Up above in the vaulted loft curl up in the Queen size bed and take in panoramic sunrise views from every angle. Head down to the sandy beach to watch the water gently roll along the sandy shore of the resort’s private beachfront. No matter the season, there is plenty to keep you entertained with an on-site indoor pool, game room, fitness center, and more! RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. DURING INCLEMENT WEATHER CONDITIONS, PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ASSOCIATED WITH OR BY WEATHER AT THE PROPERTY.

20160 Garrett Hwy Unit #F501-701, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$6,499,900
8 Beds 9 Baths
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 indoor pool with fountains and a full bath, and three levels of outdoor living, including an outdoor kitchen, built-in hot tub with gazebo, outdoor shower, and deck drainage system to keep lower levels dry. Entertain with ease in the rec room with an industrial-style bar, climate-controlled wine cellar, and fully equipped gym. Three attached garages connect to a locker-style mudroom, with a lower-level garage ideal for a side-by-side or lake toys. Radiant heat, a whole-house generator, and three dock slips make this property as functional as it is flawless. A rare opportunity to own a true statement home in one of Deep Creek Lake’s most prestigious communities. Call today for your private tour!

47 Holy Cross, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Start Your Search