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Oakland, MD 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) 998-1539

    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
  • 62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    /75

    $2,095,000 Open Sun 10AM - 12PM

    • 4 Beds
    • 4 Baths
    • 4,150 Sq Ft

    62 Duck Cove Rd, Oakland, MD 21550

    Panoramic lakefront living greets you on the point of this remarkable 4 bedroom, 4 bathroom lakefront home with 231' of premium lakefront facing east, offering amazing sunrises looking down a long stretch of the lake toward Turkeyneck! 1 oversize attached garage spaces offer plenty of space for your vehicles on the street side and 2 attached garage spaces provide room for your lake toys on the

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 376-4139

    62 Duck Cove Rd, 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

    $695,000

    • 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) 759-2822

    65 Village Dr Unit 6, 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) 896-3828

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
  • 1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    /149

    $4,450,000

    • 7 Beds
    • 7 Baths
    • 5,695 Sq Ft

    1240 Boy Scout Rd, Oakland, MD 21550

    An Iconic 50-acre Estate at Deep Creek Lake with a Deeded Boat Slip, Equestrian Amenities and Rental/Event Potential!Introducing "Double Eagle Ranch," a one-of-a-kind property at Deep Creek Lake, offering the perfect blend of luxury, outdoor adventure, and incredible income-producing potential. This 50-acre Aspen style ranch and estate is a true gem for horse lovers, nature enthusiasts, and those

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 851-4712

    1240 Boy Scout Rd, Oakland, MD 21550
  • Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    /14

    $30,000

    • Land
    • 2.45 Acres
    • $12,245 per Acre

    Lot 5A Valley Rd, Oakland, MD 21550

    2.45 Acres in the Pleasant Valley area! Previously approved perc site will need re-evaluated by Health Department. Location is within 30 minutes to Timberline and Canaan Valley Resorts, as well as Deep Creek Lake and Wisp Resort! Call today to see how this can become your future homesite!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 451-8589

    Lot 5A Valley Rd, Oakland, MD 21550
  • Lot 6 Hoye Crest Rd, Oakland, MD 21550
    Lot 6 Hoye Crest Rd, Oakland, MD 21550
    Lot 6 Hoye Crest Rd, Oakland, MD 21550
    /15

    $44,900

    • Land
    • 6 Acres
    • $7,337 per Acre

    Lot 6 Hoye Crest Rd, Oakland, MD 21550

    Opportunity to own over 6 acres on Backbone Mountain adjoining the Highest Point in Maryland! This lot will offer some of the best views from Maryland's highest point with western exposure. Approved perc and electric on site . Ready for you to build your dream home! Lots in this community have been selling fast. Call today to claim this one before it sells too!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 652-2465

    Lot 6 Hoye Crest Rd, Oakland, MD 21550
  • Lot 25 W Big Piney Dr, Oakland, MD 21550
    Lot 25 W Big Piney Dr, Oakland, MD 21550
    /2

    $4,000

    • Land
    • 0.46 Acre
    • $8,696 per Acre

    Lot 25 W Big Piney Dr, Oakland, MD 21550

    Membership lot in Youghiogheny Mountain Resort on the corner of Big Piney and Rabbit Run! Lot sale is for access to community and membership only. Non-Buildable lot. Experience over 50 miles of trails for recreational use, riding side by sides, fishing at Muddy Creek and more! Call today!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 434-0180

    Lot 25 W Big Piney Dr, Oakland, MD 21550
  • 36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    /35

    $250,000

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550

    Welcome to "Lakeview Loft" – your perfect Deep Creek getaway! This 2-bedroom, 1-bathroom unit offers expansive lake views and a central location that puts you in the heart of Deep Creek Lake. Enjoy your morning coffee with panoramic water views, or take a short walk to one of Deep Creek’s most popular plazas for your shopping and dining needs. Whether you're looking for a weekend retreat, a

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 623-5426

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
  • 1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    /60

    $295,000

    • 4 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    1056 Sunrise Dr, Oakland, MD 21550

    Welcome to 1056 Sunrise Drive! This 4-bedroom, 2-bath home offers the perfect blend of comfort and style in the heart of Oakland MD. Inside, enjoy recent renovations that add a cozy appeal throughout, including a bright and open main living area, and a refreshed kitchen and bathrooms. The fully finished basement adds valuable living space, perfect for a rec room, home office, or guest suite. Set

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 219-8052

    1056 Sunrise Dr, 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) 502-1143

    163 Crestview Dr, Oakland, MD 21550
  • Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    /9

    $35,000

    • Land
    • 2.71 Acres
    • $12,915 per Acre

    Lot 15 Little Mountain Rd, Oakland, MD 21550

    Welcome to Backbone Ridge, where privacy, natural beauty, and mountain living converge. This 2.71-acre parcel is perfectly situated near the highest point in Maryland, offering breathtaking mountain views and a tranquil, secluded setting.Located in one of the region’s most desirable areas, this property is ready for your dream home. The homesite is already cleared, a gravel driveway in place, and

    Agent Photo

    ADAM MURRAY

    BHHS Touchdown Home Pros Realty

    (240) 797-1759

    Lot 15 Little Mountain Rd, Oakland, MD 21550
  • Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    /16

    $50,000

    • Land
    • 0.60 Acre
    • $83,333 per Acre

    Lot 2 Cedar Ln, Oakland, MD 21550

    Cleared, perc approved and ready to build! Lot 2 Cedar Lane sits on a 0.6 acre level lot at the beginning of Cedar Lane which sits close to the community center, tennis courts, pavilion and only a short ride to Muddy Creek and the access to Youghiogheny River! Youghiogheny Mountain Resort offers over 50 miles of trails for riding ATV’s, side by sides, fishing at Muddy Creek and much more! The

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 594-8377

    Lot 2 Cedar Ln, Oakland, MD 21550
  • Lot 14 Dogwood Dr, Oakland, MD 21550
    Lot 14 Dogwood Dr, Oakland, MD 21550
    Lot 14 Dogwood Dr, Oakland, MD 21550
    /19

    $35,000

    • Land
    • 0.59 Acre
    • $59,322 per Acre

    Lot 14 Dogwood Dr, Oakland, MD 21550

    Buildable lot in Youghiogheny Mountain Resort! This .59 acre lot offers a level homesite with approval for a sand mound septic system. The YMR community is a gated community offering the ultimate recreational experience with over 50 miles of trails, access to state lands, Youghiogheny River and much more. Looking for a site to build your getaway? This property may be for you!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 981-5866

    Lot 14 Dogwood Dr, Oakland, MD 21550
  • 155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    /51

    $699,900

    • 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
  • 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
    /101

    $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
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /45

    $1,359,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, 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

    $3,489,000

    • 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
  • 1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    /53

    $1,599,900

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    1674 Paradise Point Rd, Oakland, MD 21550

    Beautifully remodeled lakefront home offering private dock and stunning views of Deep Creek Lake! Located on Paradise Point Rd, this home faces south for abundant natural light. 4 Bedrooms, 2.5 Bathrooms and sold fully furnished providing a gorgeous contemporary aesthetic throughout. Bright and Open with lots of glass to bring in the scenic lake views! Cozy fireplace in the main living area.

    Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
  • 415 Nazelrod Rd, Oakland, MD 21550
    415 Nazelrod Rd, Oakland, MD 21550
    415 Nazelrod Rd, Oakland, MD 21550
    /93

    $3,249,000 New Construction

    • 4 Beds
    • 5 Baths
    • 6,036 Sq Ft

    415 Nazelrod Rd, Oakland, MD 21550

    One of Garrett County's most unique and breathtaking estates—this completely custom masterpiece is set on over 63 acres of pristine land, offering unmatched privacy, panoramic valley views, and endless possibilities. Designed with meticulous attention to detail, built with 2x10 framing, this extraordinary home of over 6,000 total square feet features radiant in-floor heating, a gourmet kitchen

    Larry Smith Railey Realty, Inc.

    415 Nazelrod Rd, Oakland, MD 21550
  • 1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    /142

    $5,150,000

    • 8 Beds
    • 8.5 Baths
    • 10,300 Sq Ft

    1010 Holy Cross Dr, Oakland, MD 21550

    ICONIC. A design masterpiece of stone and timber — a true Rex Anderson build that reflects the seamless merging of inspiration and architecture. Warm, and undeniably welcoming, this home stands as a statement of craftsmanship and vision. Discover a breathtaking blend of contemporary luxury and timeless timber frame construction, perfectly positioned for privacy within the prestigious

    Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550
  • 16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550
    /70

    $589,000

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft

    16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

    Welcome to this beautifully crafted 4 bedroom, 3 bath home nestled in the sought-after Silver Ridge community, right in the heart of Deep Creek Lake. Just minutes from Wisp Resort, the lake’s public access, and all four of the area’s premier golf courses, this home offers an unbeatable location for year-round adventure and relaxation.From the moment you arrive, the home’s craftsman-style

    Justin Liller Railey Realty, Inc.

    16 Silver Ridge Ct Unit 41/2, 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
  • 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

    $529,900

    • 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
    /113

    $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
  • 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

    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
  • 321 Deer Park Hotel Rd, Oakland, MD 21550
    321 Deer Park Hotel Rd, Oakland, MD 21550
    321 Deer Park Hotel Rd, Oakland, MD 21550
    /146

    $360,000

    • 3 Beds
    • 2 Baths
    • 2,516 Sq Ft

    321 Deer Park Hotel Rd, Oakland, MD 21550

    New Price – Now $360,000!Beautifully Updated Mountain Retreat Near Deep Creek LakeHere’s your chance to own a move-in-ready mountain retreat with major upgrades—now offered at just $360,000! Located only 10 miles from Deep Creek Lake and minutes to Oakland, this 3-bedroom, 2-bath home sits on nearly an acre and blends small-town convenience with peaceful mountain living.Step

    Thomas Long Railey Realty, Inc.

    321 Deer Park Hotel Rd, Oakland, MD 21550
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /117

    $565,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    328 Stool Rock Rd, Oakland, MD 21550

    Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, 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
  • 3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    /79

    $1,295,000

    • 6 Beds
    • 3 Baths
    • 1,714 Sq Ft

    3273 Lake Shore Dr, Oakland, MD 21550

    Nestled on 100+/- feet of pristine Deep Creek Lake shoreline, this 6-bedroom, 3-bathroom cottage perfectly blends classic lakeside charm with modern comfort. Featuring a Type A dock, wood-burning stone fireplace, hardwood floors, tile bathrooms, and a remodeled kitchen with granite countertops and Bosch appliances, the home is designed for both relaxation and entertaining. Thoughtful custom

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    3273 Lake Shore Dr, Oakland, MD 21550
  • 66 Paradise Ridge Rd, Oakland, MD 21550
    66 Paradise Ridge Rd, Oakland, MD 21550
    66 Paradise Ridge Rd, Oakland, MD 21550
    /6

    $650,000

    • 4 Beds
    • 3 Baths
    • 1,680 Sq Ft

    66 Paradise Ridge Rd, Oakland, MD 21550

    Welcome to 66 Paradise Ridge Rd, a charming single-familyhome in the picturesque town of Oakland, MD. LAKE ACCESS WITH DEEDED "A" Dock.Built in 1984, this two-story residence offers a spacious layout with 4 bathrooms and 1,680square feet of finished living space. Situated on a generous 21,780-square-foot lot, theproperty provides plenty of room to roam and enjoy the natural

    Joseph Hawkins Hawkins Real Estate Company

    66 Paradise Ridge Rd, Oakland, MD 21550
  • 180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    /43

    $472,500

    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

    Discover the perfect blend of comfort and style in this finely appointed 3BR, 2.5BA vacation home, offering two fully finished levels designed for relaxation and entertaining. The main level features an inviting open floor plan with hardwood floors, a grand stone gas fireplace, and a spacious dining area filled with natural light. The gourmet kitchen is a chef’s delight, complete with custom

    Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 5

Maryland Garrett County Oakland

Real Estate & Homes for Sale in Oakland, MD

Frequently Asked Questions Why Live in Oakland

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $585,320.
Are home prices dropping in Oakland?
Yes, home prices in Oakland are down 9% in the last 12 months.
How many homes have sold over the last 12 months in Oakland, MD?
112 homes have sold in Oakland, MD over the last 12 months.
What are the most popular zip codes in Oakland, MD?
The most popular zip codes in Oakland, MD include 21550, 26764, 21561, 21541 and 26720.
How much do you need to make to afford a house in Oakland?
The median home price in Oakland is $450,000. If you put a 20% down payment of $90,000 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $2,290 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $98K a year to afford the median home price in Oakland.
How are the schools in Oakland, MD?
Oakland, MD has highly rated public and private schools. Some of the best schools in Oakland based on Niche Grades are Swan Meadow School, Crellin Elementary School and Southern Middle School. Browse all the schools in Oakland, MD to learn more.
Learn more about living in Oakland

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 99 days on the market compared to the national average of 52 days. The median sale price for homes in Oakland, MD over the last 12 months is $408,500, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$408,500
Median Single Family Sale Price
$463,000
Median Townhouse Sale Price
$544,950
Median 2 Bedroom Sale Price
$318,250
Median 1 Bedroom Sale Price
$276,500
Average Price Per Sq Ft
$266
Number of Homes for Sale
72
Last 12 months Home Sales
112
Months of Supply
7.70
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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