Oakland, MD Real Estate Search

Oakland, MD Waterfront Homes for Sale

Oakland, MD, known for its stunning natural beauty and serene atmosphere, offers a unique opportunity for prospective buyers interested in waterfront homes. Nestled among the picturesque landscapes of Deep Creek Lake and the surrounding mountains, these homes provide not only breathtaking views but also a lifestyle centered around outdoor recreation and relaxation. The real estate market in this area features a diverse selection of properties, from charming cabins to luxurious lakefront estates, catering to various tastes and preferences. With easy access to water activities like boating, fishing, and swimming, as well as hiking trails and local amenities, waterfront homes in Oakland embody a perfect blend of tranquility and adventure, making them an ideal choice for both primary residents and vacationers alike.

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Newest Oakland, MD Waterfront Homes for Sale

$296,500
1 Beds ⋅ 1 Baths
Will O the Wisp unit 105A is a charming one-bedroom, one-bath lakefront condominium. Unit 105A offers convenient first-floor living with ground-level access from a private patio directly to the waters edge, beach area and docks. . The unit features a fully equipped kitchen, comfortable living and dining areas, a cozy fireplace, one queen bed, and a sleeper sofa—accommodating up to three adults. Relax at the private patio, spending the day on the sandy beach, or taking advantage of the community’s indoor pool, game room, fitness center, and additional on-site amenities. An ideal lakefront getaway with comfort, convenience, and beautiful waterfront access!

20160 Garett Hwy Unit #105A, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,100,000
3 Beds ⋅ 2 Baths
Vintage 3BR Lakefront Dome Home with Private Type "A" Dock! & no HOA . Own a piece of Deep Creek charm with this unique 3-bedroom, 2-bath vintage lakefront home w/ 2,034 finished square ft of living area, featuring 100 feet of lake frontage, beautiful sandy shoreline, and a private dock. The eye-catching dome-style architecture sets this property apart, offering a cozy and distinctive retreat. Located just minutes from Wisp Ski & Golf Resort and the ASCI Whitewater Course, it’s perfectly positioned for year-round adventure. Currently an established rental, this home offers both personal enjoyment and income potential. Don’t miss your chance to own a truly special lakefront getaway! Schedule your showing today

2849 Shingle Camp Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$920,000
3 Beds ⋅ 2 Baths
Welcome to this charming 3Br, 2BA home in the quiet and serene Penn Point area of Deep Creek Lake. A Type A dock slip is included and is just an easy walk or golf-cart ride from the property, making lake days more convenient and enjoyable. Inside you'll find an inviting open concept kitchen, dining, and living area that flows seamlessly onto a spacious outdoor deck. Enjoy morning coffee, outdoor dining, grilling and entertaining while taking in the peaceful surroundings. The home sits on just under 1/2 acre, offering plenty of space to enjoy and potential for future expanding. The large, detached garage provides exceptional storage for your boat, jet skis, lake toys, and all your recreational gear. Whether you're looking for a year-round home or a Deep Creek getaway, this property offers the perfect combination of comfort, outdoor enjoyment, and access to the lake. Deep Creek Lake is a four-season destination with boating, golfing, hiking, skiing, dining, and activities for all ages. Conveniently located on Upper Penn Point Road, you'll be close to everything Deep Creek has to offer while still enjoying the peaceful setting. Come see all this property has to offer!

184 Upper Penn Point Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,199,000
4 Beds ⋅ 3 Baths
Beautiful lakefront home offering 89' of lakefront and a private dock. This home has been remodeled and is very warm and inviting from the moment you enter. Boasting a great island featuring granite countertops, and plenty of seating for family and friends. The lakefront views are unobstructed year round, and can be enjoyed from most any room. The outside space is just as pleasing with a wrap-around Trex deck, stone patio with a hot tub, and a firepit. If all of this isn't enough, take a few steps down to the lakefront and enjoy the type A dock. The central location is also hard to beat, just minutes to coffee, ice cream, Wisp Ski Resort, grocery stores and restaurants. Established rental "Moments & Memories". Call today to preview!

20698 Garrett Hwy, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$3,950,000
8 Beds ⋅ 10 Baths
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 right off the lower-level family room, along with a full kitchen and a playroom. Then step outside to your private lakeside retreat, complete with two relaxing hot tubs, a fire pit area, a sports court in the front, and spacious outdoor living areas ideal for dining, entertaining, or simply soaking in the peaceful surroundings. With eight spacious en-suite bedrooms, there is ample room for guests, making this an exceptional primary residence, vacation home, or luxury rental opportunity “The Haven”. Offering the perfect blend of elegance, comfort, and resort-style amenities, this extraordinary waterfront property is a rare opportunity to own the ultimate lakefront lifestyle.

1131 Lake Shore Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$225,000
1 Beds ⋅ 1 Baths
Turnkey lakeview studio at The Suites at Silver Tree! This condo has an average annual gross rental of $25,342. Enjoy beautiful views of Deep Creek Lake from your private covered balcony while owning one of the area's most desirable vacation destinations. This fully furnished studio offers an open floor plan with a king bed, sleeper sofa, cozy gas fireplace, kitchenette, dining area, and full bath, making it the perfect weekend getaway or investment opportunity. The Suites at Silver Tree features an impressive timber-frame lobby with soaring ceilings and massive stone fireplaces, an expansive lakeside deck, sandy beach, lake access, on-site marina, fitness center, sauna, game room, and Dutch's at Silver Tree restaurant. Ideally located in the heart of Deep Creek Lake, you're just minutes from Wisp Resort, golf, hiking, shopping, and year-round recreation. Whether you're looking for a low-maintenance vacation home, rental property, or your own place at the lake, this one checks all the boxes. Call today for your private showing!

565 Glendale Rd Unit #213, Oakland

Listing courtesy of The KW Collective. Contact: 4435741600
$799,000
4 Beds ⋅ 4 Baths
LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates community is adjacent to 598 acres of DNR / state land fronting on the Youghiogheny River. Set up for one level living - bedroom suite and laundry room on first floor. Features include whole-house generator, wood-burning fireplace, a recently finished basement adding a game room and a fourth bedroom, front and rear decks (trex on back deck), covered porches, fire-pit, wrap-around driveway and a spacious loft that serves as a third living room. Must see to appreciate the solitude of this fantastic home! Furnishings negotiable. Short term rentals are not permitted in this community.

325 Markwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$1,425,000
3 Beds ⋅ 2 Baths
Cozy cottage with split lakefront and Type A dock located in the serene quiet Penn Point Cove. This quaint home has plenty of room for family, guests and entertaining. The covered & heated outdoor deck facing the lake is a great place for morning coffee and evening dinner. The large, bright kitchen & dining area is another great entertaining space with quartz countertops, stainless steel appliances and plenty of room for large family gatherings. The home has 2 bedrooms on the main floor, a roomy living area with fireplace, full bathroom and a bonus sunroom with a wood burning fireplace. Upstairs has a great bunk room bedroom that can easily sleep 4 people, plus another living room and bathroom with a claw foot tub and shower. Beautifully landscaped outdoor area has a firepit space, a detached garage with plenty of storage area and an easy walk to your dock area. Great places to watch some of the best sunsets! This home will convey turnkey furnished with a few seller exceptions. Schedule your tour today, this home has so much to offer.

187 Lower Penn Point Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$775,000
5 Beds ⋅ 5 Baths
One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. Seller also offering an adjacent unbuilt riverfront lot (#9) for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$550,000
2 Beds ⋅ 2 Baths
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 assigned deep-water boat slip, outdoor storage, and access to 11 acres of incredible amenities: a heated pool, tennis courts, playground, kayak racks, and a stone fire pit. Major community updates include a new metal roof and resurfaced courts. Just minutes from downtown Oakland, Garret Cinemas, and shopping! Seller will sell his 2011 Sea Ray 195 with 4.2 L EFI engine for $4500.00 OBO "As=Is " see photos and dock slip

193 Red Run Rd Unit #1-B-3, Oakland

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005
$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:

$899,900
5 Beds ⋅ 5 Baths
One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. The house on lot 8 is also offered on its own WITHOUT the adjacent riverfront building lot for $775,000, MLS listing #MDGA2012378. Lot #9 offered by itself for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$309,000
1 Beds ⋅ 1 Baths
Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or income-producing rental. Start your mornings with exceptional sunrises from your private lakefront balcony, then enjoy the many resort-style amenities Will O' the Wisp has to offer, including an indoor heated pool, hot tubs, fitness room, sauna, arcade/game room, sandy beach, covered garage parking, restaurant access, community boat slip access through the POA, and a fully serviced front desk for guest support and added convenience. Currently operating as a successful short-term rental through Railey Vacations, this rarely available lakefront condo is located just minutes from Wisp Resort, state parks, dining, shopping, and four-season Deep Creek Lake recreation.

20160 Garrett Hwy Unit #H706, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$399,900
2 Beds ⋅ 1 Baths
Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added functionality of the upper-level loft living space with desk area and additional bedroom. A custom wine rack with built-in liquor cabinet adds the perfect finishing touch to this inviting mountain-lake retreat. Community amenities include; a game room, fitness center, meeting room and convenient on-site laundry facilities. Located just steps from one of the lake's most popular waterfront dining destinations, Dutch's at Silver Tree. Also, conveniently located to a host of other attractions; State parks, Wisp Golf and Ski Resort, Thousand Acres Lakeside Golf Club and more! Call today to schedule your private tour.

565 Glendale Rd Unit #303B, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$1,400,000
5 Beds ⋅ 4 Baths
Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with abundant parking, oversized multi-car garage with interior access, usable backyard, wooded walking paths, and nearby UTV and snowmobile trails, the setting offers a rare balance of privacy and recreation. Inside, natural light fills the home, where hardwood floors, cathedral ceilings, wood-burning fireplaces, and open-concept living spaces create warmth and character. A flexible layout with multiple living areas offers room for gathering, multi-generational living, or separate guest quarters, with potential for vacation rental use. Minutes from Pawn Run, downtown Oakland, and a short drive or boat ride to Wisp Resort, restaurants, and shopping, this is a rare opportunity to own a legacy property designed for making memories for generations.

827 Penn Point Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$329,900
1 Beds ⋅ 1 Baths
Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks, and boating convenience—all just steps away. This property is not only the perfect getaway, but also a proven Vacation Rental Income Producing Condo —Recognized as one of the top-performing rental units in the SilverTree building, averaging $30,000 per year in Vacation Rental Income. Whether you're looking for a low-maintenance lake retreat or a high-performing income-producing property, this unit delivers the best of both worlds in one of Deep Creek’s most desirable lakefront communities. Call today to schedule a private showing.

565 Glendale Rd Unit #125, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$299,900
2 Beds ⋅ 1 Baths
Charming true 1-bedroom + loft (can be used as 2nd bedroom) condo at Silver Tree Suites, LAKEFRONT living at its finest! This spacious second-floor unit features a private balcony, fully equipped kitchenette, cozy gas fireplace and abundant natural light. Enjoy resort-style amenities including a fitness center, sauna, on-site laundry and game room, plus steps-away fine dining at Dutch’s at Silver Tree and cocktails on Harbor Bar’s waterfront deck with breathtaking views of Deep Creek Lake. Here, every day is a promise of relaxation, adventure, and luxury living. Located just minutes from Wisp Ski Resort, Swallow Falls, hiking trails, whitewater rafting, golf courses, Deep Creek Lake State Park beach and boat ramp, and local shopping, this property is ideally situated. Take this rare opportunity to own your own slice of Lakefront paradise at Deep Creek Lake! Schedule your private showing today!

565 Glendale Rd Unit #B206, Oakland

Listing courtesy of Jason Mitchell Group. Contact: 4105335486
$6,499,900
7 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:

$339,900
2 Beds ⋅ 1 Baths
Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering flexibility and privacy. Take in views of Deep Creek Lake and just a stones throw from your door, enjoy unbeatable proximity to Dutch’s at Silver Tree and The Harbor Bar. Whether you're looking for a weekend retreat or a hassle-free getaway, this turnkey condo is truly maintenance-free—just drop your bags and start enjoying lake life!

531 Glendale Rd Unit #B302, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$160,000
1 Beds ⋅ 1 Baths
Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western exposure centrally located to all area amenities. Unit 212A offers a one level floorpan with private bedroom on the second floor of building A which offers easy access to the lobby, elevator, gym, sauna, game room and patio area overlooking the lake. Condominium ownership at Silver Tree Suites offers ease of maintenance as the association takes care of all of the grounds and building maintenance. This unit is an established vacation rental ready for you to take ownership this summer! Call today to schedule a private showing!

565 Glendale Rd Unit #212A, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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