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

    $2,195,000

    • 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) 837-8381

    62 Duck Cove Rd, 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
  • 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) 869-6858

    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) 332-0716

    Lot 25 W Big Piney Dr, 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
  • 4.00 Acres Moose Crossing, Oakland, MD 21550
    4.00 Acres Moose Crossing, Oakland, MD 21550
    4.00 Acres Moose Crossing, Oakland, MD 21550
    /18

    $89,000

    • Land
    • 4.00 Acres
    • $22,250 per Acre

    4.00 Acres Moose Crossing, Oakland, MD 21550

    Welcome to Moose Crossing – a rare opportunity to own a mostly level, open 4-acre parcel in a peaceful rural setting. This expansive lot offers minimal clearing with no major trees, making it easy to begin building. Approved for up to a 3-bedroom home, it’s the perfect canvas for your full-time residence, vacation retreat, or investment property. No zoning or HOA! Enjoy the tranquility of country

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 349-7682

    4.00 Acres Moose Crossing, 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
  • 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) 981-5925

    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) 617-3988

    Lot 14 Dogwood 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
  • 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) 221-6329

    Lot 5A Valley Rd, 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

    $925,000 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
  • 197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    /150

    $3,890,000

    • 5 Beds
    • 3.5 Baths
    • 4,156 Sq Ft

    197 Black Angus Dr, Oakland, MD 21550

    A one of a kind lakefront retreat overlooking a beautiful cove in the peaceful Pergin Farm community at Deep Creek Lake. Situated at the end of a quiet lane, the completely updated 5 bedroom 4.5 bath cottage style home also offers a separate 2 bedroom 2 bath guest dwelling, two individual dock sites and a beautiful tennis facility. With 2.15 acres+- and 400' of prime lake frontage at the end

    Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, 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
  • 1473 Pergin Farm Rd, Oakland, MD 21550
    1473 Pergin Farm Rd, Oakland, MD 21550
    1473 Pergin Farm Rd, Oakland, MD 21550
    /79

    $999,500

    • 4 Beds
    • 2 Baths
    • 2,230 Sq Ft

    1473 Pergin Farm Rd, Oakland, MD 21550

    TIME TO UNWIND at this absolutely stunning Deep Creek Lake retreat boasting million-dollar panoramic views and private lake access! This fully furnished, meticulously renovated 4-bedroom, 2-bath raised rancher is the ultimate escape—perfect for weekend getaways, full-time living, or a savvy investment—sited on 2 pristine acres in the highly sought-after Pergin Farm community, a peaceful peninsula

    Tony Migliaccio Long & Foster Real Estate, Inc.

    1473 Pergin Farm Rd, 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

    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
  • 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
  • 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
  • 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

    $3,689,000

    • 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
  • 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
  • 503 Southern Pines Dr, Oakland, MD 21550
    503 Southern Pines Dr, Oakland, MD 21550
    503 Southern Pines Dr, Oakland, MD 21550
    /62

    $399,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,642 Sq Ft

    503 Southern Pines Dr, Oakland, MD 21550

    Brand new and built to make life easy. Tucked in the quiet, sought-after Southern Pines community, this single-level home keeps everything simple and smooth. Three beds, two and a half baths, and space that actually works. Oversized two-car heated garage. Inside, the kitchen comes complete with stainless appliances, hardwood cabinets, stone tops, walk-in pantry, and a big island bar made for

    Jon Bell Railey Realty, Inc.

    503 Southern Pines Dr, 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 $849,906.
Are home prices dropping in Oakland?
Yes, home prices in Oakland are down 24% in the last 12 months.
How many homes have sold over the last 12 months in Oakland, MD?
54 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 $529,500. If you put a 20% down payment of $105,900 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $2,740 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $117K 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 120 days on the market compared to the national average of 70 days. The median sale price for homes in Oakland, MD over the last 12 months is $514,000, down 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$514,000
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$369,900
Median 2 Bedroom Sale Price
$440,000
Median 1 Bedroom Sale Price
$259,999
Average Price Per Sq Ft
$372
Number of Homes for Sale
39
Last 12 months Home Sales
54
Months of Supply
8.70
Median List Price
$529,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
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