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Oakland Homes for Sale

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  • 15 Village Dr Unit 1, Oakland, MD 21550
    15 Village Dr Unit 1, Oakland, MD 21550
    15 Village Dr Unit 1, Oakland, MD 21550
    /37

    $440,000

    • 2 Beds
    • 1 Bath

    15 Village Dr Unit 1, Oakland, MD 21550

    Escape to a simpler time with all the modern conveniences you desire at this 2-bedroom log cabin in the Yellowstone Village. The main level envelops you with the uniqueness and charm from the great room with an old-fashioned stone fireplace to warm up the chilling evenings and furniture that begs you to sit a while, to the quaint, yet full-sized kitchen with the cutest dining table. Venture up

    Agent Photo

    Dale Carpenter

    Railey Realty, Inc.

    (240) 255-9771

    15 Village Dr Unit 1, Oakland, MD 21550
  • 621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, Oakland, MD 21550
    /97

    $695,000

    • 4 Beds
    • 3 Baths
    • 3,242 Sq Ft

    621 Paradise Heights, Oakland, MD 21550

    Opportunity to own one of Deep Creek Lake's most unique homes! 621 Paradise Heights is a geodesic dome house offering 4 bedrooms, 3 full bathrooms and over 4300 square feet of interior space. Become the ultimate host of guests with the many entertainment spaces in the house including main level living room, parlor with wet bar, expansive deck, stacked stone fireplace, fit pit in back yard and

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 240-3916

    621 Paradise Heights, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H708, Oakland, MD 21550
    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    /47

    $300,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    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

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (301) 479-6357

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • 267 Woodlands Hill Ln, Oakland, MD 21550
    267 Woodlands Hill Ln, Oakland, MD 21550
    267 Woodlands Hill Ln, Oakland, MD 21550
    /72

    $1,075,000

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft

    267 Woodlands Hill Ln, Oakland, MD 21550

    267 Woodlands Hill Lane offers mountain living at its finest! This custom, 2021 built chalet is designed for ultimate comfort and enjoyment. The mountain setting offers breathtaking views with a location close to all of the areas most desirable amenities. Offering 4 bedrooms, 3.5 bathrooms and 3 levels of living, this home offers plenty of room for entertaining guests. You'll be greeted with oak

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 895-9233

    267 Woodlands Hill Ln, Oakland, MD 21550
  • 65 Village Dr Unit 6, Oakland, MD 21550
    65 Village Dr Unit 6, Oakland, MD 21550
    65 Village Dr Unit 6, Oakland, MD 21550
    /52

    $715,000

    • 3 Beds
    • 3 Baths
    • 1,740 Sq Ft

    65 Village Dr Unit 6, Oakland, MD 21550

    Looking for that cozy cabin getaway at the lake? 65 Village Drive offers cabin living at its finest with 3 full bedrooms and 3 full bathrooms minutes from all of Deep Creek Lake's most popular amenities. Two wood burning fireplaces give ultimate ambiance in the main level living room and four seasons room where the hot tub is also located. The Yellowstone Village community offers one of Deep

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 820-3626

    65 Village Dr Unit 6, Oakland, MD 21550
  • 163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, Oakland, MD 21550
    /50

    $335,000

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    163 Crestview Dr, Oakland, MD 21550

    Welcome to 163 Crestview Drive — a beautifully maintained 3-bedroom, 2.5-bath home nestled in the Mitchell Manor neighborhood. This inviting Cape Cod offers timeless charm, modern updates, and a peaceful setting just minutes from downtown Oakland. Many recent improvements including HVAC, water treatment/filtration system, flooring and landscaping! Step inside to an open, light-filled floor plan

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 363-0878

    163 Crestview Dr, Oakland, MD 21550
  • 565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    /20

    $215,000

    • 1 Bed
    • 1 Bath
    • 527 Sq Ft

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550

    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

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 923-7703

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
  • Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    /24

    $19,000

    • Land
    • 0.69 Acre
    • $27,536 per Acre

    Lot 31 Fawn Dr, Oakland, MD 21550

    Lot 31 Fawn Drive offers a serene 0.69-acre wooded setting in the desirable Youghiogheny Mountain Resort—a gated community perfect for outdoor enthusiast. This peaceful parcel is approved for a sand mound septic system, making it a great spot for your future mountain getaway or full-time residence. Engineering plans on file for the sand mound system, ready for you to begin building your dream

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 594-8525

    Lot 31 Fawn Dr, Oakland, MD 21550
  • 2045 Swallow Falls Rd, Oakland, MD 21550
    2045 Swallow Falls Rd, Oakland, MD 21550
    2045 Swallow Falls Rd, Oakland, MD 21550
    /79

    $950,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 5,416 Sq Ft

    2045 Swallow Falls Rd, Oakland, MD 21550

    Craftsman elegance awaits you at this newly built home just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls the Youghiogheny River and all of western Maryland's finest attractions! No details were missed! it would be very difficult to recreate this home today at this price with today's building costs. Offering 5 bedrooms, 3.5 bathrooms and over 5400 square feet of living space, this home

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 663-8213

    2045 Swallow Falls Rd, Oakland, MD 21550
  • 346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    /73

    $529,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    346 Skippers Point Rd, Oakland, MD 21550

    Escape to your ideal mountain-lake retreat at Deep Creek Lake with this charming chalet-style home, nestled in a peaceful, wooded setting. This warm and inviting 3-bedroom, 2-bath getaway blends rustic charm with modern comfort—perfect as a vacation home or full-time residence. Take in filtered lake views from your home and expansive deck or relax by the lake with exclusive access to a sandy

    Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, Oakland, MD 21550
  • 19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    /81

    $1,349,000

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft

    19956 Garrett Hwy Unit 6, Oakland, MD 21550

    Experience the best in maintenance free lakefront living on Deep Creek Lake! This 4 BR 4 Bath lakefront townhome with assigned dock slip is located within walking distance of many of the lake's best restaurants and attractions. The open floor plan offers a main level great room and lower level family/game room. The large kitchen offers a lake facing island with breakfast bar. Three

    Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
  • 113 Paradise Ln, Oakland, MD 21550
    113 Paradise Ln, Oakland, MD 21550
    113 Paradise Ln, Oakland, MD 21550
    /61

    $1,389,000

    • 5 Beds
    • 3 Baths
    • 2,056 Sq Ft

    113 Paradise Ln, Oakland, MD 21550

    Incredible opportunity to own a 5 bedroom, 3 bath lakefront home with over 215 feet of prime frontage on Deep Creek Lake! Situated on a level to gently sloping lot, this property offers expansive views and easy lake access in one of the area's most desirable settings. Inside, you’ll find tasteful upgrades throughout—including a beautifully renovated kitchen with higher-end finishes and updated

    Nina Beitzel Railey Realty, Inc.

    113 Paradise Ln, Oakland, MD 21550
  • 444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    /83

    $1,295,000

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft

    444 Woodlands Hill Ln, Oakland, MD 21550

    Experience the serenity of Deep Creek Lake from this updated luxury 4 bedroom home with over 5,000+ square feet! The seller’s improvements over the last few years showcase impeccable craftsmanship and outstanding construction quality, both inside and out. Nestled on 2 acres in a private community, enjoy beautiful water views of the lake from the expansive front deck or from many of the interior

    Mike Kennedy Railey Realty, Inc.

    444 Woodlands Hill Ln, Oakland, MD 21550
  • 783 Mountainview Dr, Oakland, MD 21550
    783 Mountainview Dr, Oakland, MD 21550
    783 Mountainview Dr, Oakland, MD 21550
    /76

    $595,000

    • 3 Beds
    • 3 Baths
    • 1,971 Sq Ft

    783 Mountainview Dr, Oakland, MD 21550

    Beautiful, 3 bedroom, 3 bath home located in the sought after community of Mountainside at Deep Creek Lake. This home offers one level living, 2 bonus rooms which could be used as extra sleeping areas, a sauna, 2 car attached garage, a large & level yard. Enjoy several community amenities including lake access, a marina, picnic areas, tennis & basketball courts, & more! A current vacation rental

    Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
  • 102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    /103

    $975,000

    • 7 Beds
    • 4.5 Baths
    • 5,376 Sq Ft

    102 Mountainview Ct, Oakland, MD 21550

    Mountainside Luxury Log Home. "Boulder Escape" is a stunning 7-bedroom, 4.5 bath lake access home on 1.6 acres in this prestigious mountaintop community. This income-producing property, offering over 5600 square feet, has an open concept floor plan with amazing expansive space on all levels. You will find an easy flow throughout the living, dining, and kitchen areas. Comfort and ambiance are

    Kathy Gibson Railey Realty, Inc.

    102 Mountainview Ct, Oakland, MD 21550
  • 290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    /65

    $299,000

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft

    290 Crellin Underwood Rd, Oakland, MD 21550

    Awesome 3BR/2BA Log home sitting on 2 acre lot. Third bedroom in on lower level and does not have an egress window. Full bath with soaking tub on main level with 24 X 12 bedroom and additional BR. Full bath on lower level as well. Huge Family Room with Native Stone wall with wood burning stove to supplement heating system. Heat is propane forced air. Large deck, partially covered on main level.

    Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
  • 56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    /141

    $2,845,000

    • 6 Beds
    • 7.5 Baths
    • 5,100 Sq Ft

    56 Bee Tree Ln, Oakland, MD 21550

    Unmatched EXCEPTIONAL Lakefront Living – 6 Bedrooms | 7.5 Baths | Tucked Among the PinesDiscover a rare opportunity to own a true lakefront, lakeview gem—this 5,400 sq ft, 6-bedroom, 7.5-bath home that is nestled among tall pines on an exceptional lot that sits unusually close to the water’s edge. With peaceful views across a quiet cove and expansive open-water vistas from the oversized covered

    Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, Oakland, MD 21550
  • 433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    /66

    $599,900

    • 6 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    433 San Francisco St, Oakland, MD 21550

    Fully renovated, fully loaded, and fully ready to be your Deep Creek Lake getaway! This 6-bedroom mountain retreat is packed with upgrades—New flooring, new septic, new hot tub, and a sleek modern kitchen with concrete counters, soft-close cabinets, and stainless steel appliances. One wood-burning fireplace for the cozy nights, one propane for the lazy mornings. Two and a half bathrooms, all

    Jon Bell Railey Realty, Inc.

    433 San Francisco St, Oakland, MD 21550
  • 2719 Broadford Rd, Oakland, MD 21550
    2719 Broadford Rd, Oakland, MD 21550
    2719 Broadford Rd, Oakland, MD 21550
    /98

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 4,253 Sq Ft

    2719 Broadford Rd, Oakland, MD 21550

    Stunning Brick Ranch Near Broadford Lake Park! This magnificent one-level brick ranch sits on a level 1.5-acre lot backing to scenic farmland and walking distance to Broadford Lake Park. The 3,600 sq. ft. floor plan includes a master suite with a private bath, his & her closets, custom tiled shower, and granite vanity tops.The recently remodeled kitchen features granite countertops, an oversized

    Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
  • 25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    /52

    $775,000

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any season, while offering views from

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    25 Silver Tree Ln, Oakland, MD 21550
  • 155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    /51

    $714,900

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft

    155 Basswood Way, Oakland, MD 21550

    Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped in fresh stain (09/24) and packed with updates - "Time Is On My Side" is dialed in for comfort. Five bedrooms, three baths, including a main-level primary. Inside, modern meets rustic with a sleek kitchen, new propane fireplace, and fresh paint throughout. The lower level offers a second living area, pool

    Michael Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
  • 247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    /82

    $569,900

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550

    Overlooking Deep Creek Lake, this modern townhome delivers luxury, comfort, and unbeatable convenience. Located in Timberlake Village, the 5-bedroom, 4.5-bath retreat is minutes from top restaurants, marinas, state parks, and Wisp Resort. The main level was recently reimagined with contemporary lighting and timber accents, a modern kitchen featuring granite counters, stainless appliances, and a

    Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
  • 36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, Oakland, MD 21550
    36 Ridgewood Dr, Oakland, MD 21550
    /60

    $525,000

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft

    36 Ridgewood Dr, Oakland, MD 21550

    Looking for the secluded cabin in the woods but want to be close to everything the Lake has to offer? Look no further! This 3 bedroom 3 1/2 bath home offers just that! Located in the established and sought after community of Mountainside, this home is an inviting and place where you can get away from it all. Cozy up to the large stone wood burning fireplace in the living room, open concept

    Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
  • 3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    /71

    $625,000

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft

    3084 Lake Shore Dr, Oakland, MD 21550

    Cozy Retreat on Lake Shore Drive! This 4-bed, 3-bath cottage was built for relaxation, entertainment, and making memories. The open-concept living area keeps everyone connected, while the expansive deck and hot tub allow you to take the fun outside. Upstairs, the primary suite steals the show! A personal fireplace with a wall of glass to let in the light and soak in the views. Three more bedrooms

    Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
  • 1118 Lake Shore Dr, Oakland, MD 21550
    1118 Lake Shore Dr, Oakland, MD 21550
    1118 Lake Shore Dr, Oakland, MD 21550
    /95

    $675,000

    • 3 Beds
    • 2 Baths
    • 2,446 Sq Ft

    1118 Lake Shore Dr, Oakland, MD 21550

    Escape to Serenity: Your Dream Log Home Awaits! Nestled in the heart of a picturesque lake and mountain area, this charming log home offers the perfect blend of rustic charm and modern touches. With cathedral wood ceilings and a cozy gas fireplace, the spacious living area invites you to relax and soak in the warmth and beauty of your surroundings. The living area steps out to a large covered

    Susan Bell Railey Realty, Inc.

    1118 Lake Shore Dr, Oakland, MD 21550
  • 170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    /45

    $589,000

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550

    Spacious home located in the Timberlake Village community. This duplex home offers three levels of living space, granite counter tops, hardwood flooring, propane fireplace and an attached garage. The large kitchen and open floorplan make this an ideal permanent or vacation home. The exterior space is just as pleasing offering a covered front deck and a lower patio, which boasts a hot tub for your

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
  • 1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    /93

    $3,689,000

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft

    1931 Lake Shore Dr, Oakland, MD 21550

    Deep Creek Lakes, Sunset Hills, luxury retreat offering majestic mountain & lake views. A unique lakefront property that plays a perfect host to relaxing vacations with family and friends is a low-key lifestyle centered around the outdoors. Vast stretches of glass ensure a sparkling water view is always on hand. Though sleek materials and high-end finishes abound, their low-profile design puts

    Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • 939 Glendale Rd Unit 19, Oakland, MD 21550
    939 Glendale Rd Unit 19, Oakland, MD 21550
    939 Glendale Rd Unit 19, Oakland, MD 21550
    /30

    $785,000

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft

    939 Glendale Rd Unit 19, Oakland, MD 21550

    SEE DOCUMENTS FOR 07/2025 TAX STATEMENT--$1,533 annual assessment for HOA reserves. $1,500 Annual fee to Bill's Marine for assumable boat-strip lease. $4,500 Annual condo fees. Condo Association responsible for roof, building exterior maintenance, lawn maintenance, snow removal, replacement of deck, porch and front door. Water is included in the condo fees. Sewer fees are not and averaged $90

    Rick Davis Richard A. Davis & Associates

    939 Glendale Rd Unit 19, Oakland, MD 21550
  • 20160 Garrett Hwy Unit G509, Oakland, MD 21550
    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    /35

    $399,900

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft

    20160 Garrett Hwy Unit G509, Oakland, MD 21550

    Experience lakefront living at its finest with this beautifully updated 2-level condo on the shores of Deep Creek Lake. Unit G509 features 2 bedrooms and 1 full bathroom, offering breathtaking lake views. The main level includes a well-appointed kitchen and a cozy living area complete with a wood-burning fireplace—perfect for year-round relaxation. Upstairs, you’ll find two spacious bedrooms with

    Tim Macauley Taylor Made Deep Creek Vacations & Sales

    20160 Garrett Hwy Unit G509, Oakland, MD 21550
  • 198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    /45

    $825,000

    • 3 Beds
    • 3 Baths
    • 2,744 Sq Ft

    198 Grandview Dr, Oakland, MD 21550

    Lake views for days and room to relax in every direction!Welcome to 198 Grandview Drive, a 3-bedroom, 3-bath log home perfectly perched to capture sweeping views of Deep Creek Lake and the surrounding mountains. With three finished levels of living space, this home blends rustic charm with modern comfort. Hardwood floors span the main and upper levels, while the finished lower level features

    Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
  • 873 Paradise Heights, Oakland, MD 21550
    873 Paradise Heights, Oakland, MD 21550
    873 Paradise Heights, Oakland, MD 21550
    /72

    $859,000

    • 5 Beds
    • 4 Baths
    • 2,934 Sq Ft

    873 Paradise Heights, Oakland, MD 21550

    Escape to Sage Mountain Retreat, a beautifully crafted 5-bedroom, 4-bath custom home nestled in a private wooded setting—just minutes from Deep Creek Lake State Park and walking distance to popular lakefront restaurants and Silvertree Marina. This fully furnished retreat features: Modern kitchen with granite countertops, Two spacious living areas for relaxing or entertaining, Primary Bedroom

    Rich Orr Railey Realty, Inc.

    873 Paradise Heights, Oakland, MD 21550
  • 285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    /50

    $589,000

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550

    Welcome to this stunning 5-bedroom, 4.5-bathroom duplex-style home at Deep Creek Lake, offering the perfect blend of mountain charm, modern finishes, and exceptional rental potential. This meticulously maintained retreat spans three finished levels and boasts a spacious, professionally designed lower-level patio featuring a cozy fire pit, relaxing mountain views, and a brand-new 2024 hot

    Mike Kennedy Railey Realty, Inc.

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
  • 531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    /29

    $369,000

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    531 Glendale Rd Unit B302, Oakland, MD 21550

    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

    Larry Smith Railey Realty, Inc.

    531 Glendale Rd Unit B302, Oakland, MD 21550
  • 175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    /55

    $555,000

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Amazing and rare opportunity in Trader's Landing! These wonderful stand alone homes in this community do not come up for sale very often. Offering 4 bedrooms, 4 and a half baths, and over 3,100 finished square feet on 4 levels of living space, this is one of the largest homes in the development! Enjoy relaxing with some nice views on the spacious deck or go for a soak in the hot tub on the

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • 189 Red Run Rd Unit 1C2, Oakland, MD 21550
    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    /50

    $589,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    189 Red Run Rd Unit 1C2, Oakland, MD 21550

    2+BR, 2BA waterfront condo at Red Run offering lake views and assigned deep water boat slip! Immaculately maintained, the owners have remodeled the entire unit in the last year. Luxurious and well-appointed with upscale furnishings & contents - conveys essentially TURNKEY. Gorgeous master suite with lake views, spacious bedrooms, wood burning fireplace, lakeside balcony and additional outdoor

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    189 Red Run Rd Unit 1C2, Oakland, MD 21550
  • 12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    /51

    $554,900

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    SOLD TURN KEY - FULLY FURNISHED!!! As its vacation rental name describes, "Whispering Waters" provides a glistening open view of Deep Creek Lake from nearly every window! This 3 bedroom, 3 and 1/2 bath townhome is located right in the middle of all of the areas amenities and very close to restaurants, boat rentals, and more! All of the modern conveniences and finishes are included such as central

    Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
  • 20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    /39

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

    Lakefront Luxury at Will O’ The Wisp – Nicely renovated Unit 308/408 offers a 2 BR, 2 Bath 2- level floor plan perfect for guests or steady rental income. Enjoy breathtaking Deep Creek Lake views from every bedroom and the main living space. Resort-Style Amenities Include:Indoor Pool with Waterfall Hot Tub, Cedar-Lined Sauna, Fitness Room & Game Room, Sandy Lakefront Beach with Community Boat

    Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
  • 565 Glendale Rd Unit 307A, Oakland, MD 21550
    565 Glendale Rd Unit 307A, Oakland, MD 21550
    565 Glendale Rd Unit 307A, Oakland, MD 21550
    /43

    $329,900

    • 1 Bed
    • 1 Bath
    • 832 Sq Ft

    565 Glendale Rd Unit 307A, Oakland, MD 21550

    Third-level unit at Silver Tree Suites with direct lake frontage and stunning water views. One-bedroom plus loft, one bath, and a cozy fireplace create the perfect getaway. Strong rental potential, top-tier amenities, and direct access to the lake’s best restaurant. Professional on-site management handles everything, so you don’t have to. Hit the gym, unwind in the sauna, or kick back in the game

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 307A, Oakland, MD 21550
  • 565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    /55

    $349,900

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    565 Glendale Rd Unit 125, Oakland, MD 21550

    Wake up to the lake at your doorstep. This ground-level, end-unit condo puts you right where you want to be—direct lakefront with unbeatable access to everything Deep Creek offers. Walk out to the water, hit the gym, unwind in the sauna, or challenge friends in the game room. Dutch’s at Silver Tree, The Harbor Bar, and Silvertree Marina are all within reach, making lakeside dining and boat days

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • 20 Maple Del Ln, Oakland, MD 21550
    20 Maple Del Ln, Oakland, MD 21550
    20 Maple Del Ln, Oakland, MD 21550
    /17

    $549,000 New Construction

    • 2 Beds
    • 1 Bath

    20 Maple Del Ln, Oakland, MD 21550

    *To be built A frame* Looking for a newly built home on a wooded lot close to everything Deep Creek Lake offers. This home can be delivered complete in a 4 month time span. Call today for details

    Michael Cumerlato Jason Mitchell Group

    20 Maple Del Ln, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 3

Maryland Oakland Oakland

Real Estate & Homes for Sale in Oakland, Oakland

Frequently Asked Questions Why Live in Oakland

Is Oakland a good place to live?
Oakland is a good place to live. Oakland is considered car-dependent and somewhat bikeable. Oakland has 5 parks for recreational activities. A local real estate agent serving Oakland can help you decide if this neighborhood is the right one for you. Learn more on our Oakland neighborhood guide.
What are the best public schools in Oakland?
The best public schools that serve Oakland are:
What are the most popular zip codes in Oakland, Oakland, MD?
The most popular zip codes in Oakland, Oakland, MD include 21550, 21561, 26764, 21541 and 21520.
Learn more about living in Oakland
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