124

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

    $425,000

    • 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
  • 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

    $289,900

    • 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 your

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (301) 479-6357

    20160 Garrett Hwy Unit H708, 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

    $625,000

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

    65 Village Dr Unit 6, Oakland, MD 21550

    One of Deep Creek Lake's best performing vacation rental properties! Over 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; one in the main level living room and one in the four seasons room where the hot tub is also located. Many recent

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 759-2822

    65 Village Dr Unit 6, 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
  • 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
    • 0.6 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
  • Lots 13/17 Dogwood Dr, Oakland, MD 21550
    Lots 13/17 Dogwood Dr, Oakland, MD 21550
    Lots 13/17 Dogwood Dr, Oakland, MD 21550
    /26

    $32,000

    • Land
    • 1.23 Acres
    • $26,016 per Acre

    Lots 13/17 Dogwood Dr, Oakland, MD 21550

    Discover the perfect blend of privacy and potential with these two adjoining lots located in the Youghiogheny Mountain Resort community. Lot 13 Dogwood Drive and Lot 17 Birchwood Drive together offer 1.23 wooded acres of mountain serenity, with the rear property lines connected for an expansive feel and extra buffer from neighbors. Lot 13 is approved for a sand mound septic system, making it an

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-6552

    Lots 13/17 Dogwood Dr, 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
    /18

    $44,900

    • Land
    • 6.12 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 to site, ready for you to build your dream home! Residential community. No camping, no hunting. Call today to schedule a time too see this remarkable property!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 652-2465

    Lot 6 Hoye Crest Rd, Oakland, MD 21550
  • 163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, Oakland, MD 21550
    /50

    $325,000

    • 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
  • 565 Glendale Rd Unit 210-A, Oakland, MD 21550
    565 Glendale Rd Unit 210-A, Oakland, MD 21550
    565 Glendale Rd Unit 210-A, Oakland, MD 21550
    /33

    $175,000

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

    565 Glendale Rd Unit 210-A, Oakland, MD 21550

    Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel communities! Silver Tree Suites offers over 350' of pristine lakefront with western exposure. Located directly adjacent to Dutch's at Silver Tree, this location offers convenience to one of the areas most desirable restaurants, and is only 5-10 minutes to all of the local amenities and attractions you come to

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 623-5408

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
  • Lot 18 Laurel Ct, Oakland, MD 21550
    Lot 18 Laurel Ct, Oakland, MD 21550
    Lot 18 Laurel Ct, Oakland, MD 21550
    /35

    $95,000

    • Land
    • 1.08 Acres
    • $87,963 per Acre

    Lot 18 Laurel Ct, Oakland, MD 21550

    Discover the perfect setting for your Deep Creek Lake getaway on this beautiful 1.08-acre homesite located at the end of a quiet cul-de-sac in the desirable Paradise Ridge community. Lot 18 Laurel Court offers a peaceful, private setting surrounded by mature trees and mountain views. Paradise Ridge features one of the nicest lake access areas on Deep Creek Lake—perfect for swimming, kayaking, and

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 916-1185

    Lot 18 Laurel Ct, 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

    $210,000

    • 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
  • 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
  • 1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    /149

    $4,390,000

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

    1240 Boy Scout Rd, Oakland, MD 21550

    Welcome to Double Eagle Ranch — quite possibly the most beautiful property in Garrett County. This iconic 50-acre estate is set in the heart of Deep Creek Lake and includes its own deeded waterfront parcel with a brand-new dock, giving you private lake access just minutes from the property. Rarely does an offering combine such incredible privacy, natural beauty, and income-producing potential in

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 851-4712

    1240 Boy Scout Rd, 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

    $649,000

    • 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
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /117

    $545,000

    • 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 separate

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, Oakland, MD 21550
  • 329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    /81

    $750,000

    • 4 Beds
    • 3.5 Baths
    • 2,632 Sq Ft

    329 Lemley Dr, Oakland, MD 21550

    Lake View Chalet at Deep Creek Lake – This 4 Bedroom 3.5 Bath Mountain Home is privately seated on 1.72 acres of wooded land and features vaulted ceilings, an oversized loft, 2 gas fireplaces, and seasonal views of Deep Creek Lake! Open layout with hardwood floors and custom built-in bookshelves. Walk-out basement with 2nd living space and a pool table. Two stories of outdoor living with upper

    Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
  • 47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    /109

    $6,499,900

    • 8 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, Oakland, MD 21550
  • 180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    /98

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    180 Paradise Ridge Rd, Oakland, MD 21550

    Discover your perfect Deep Creek Lake getaway in the desirable Ridge at Paradise Point community, where breathtaking lake views and incredible amenities await! This charming entry level vacation home offers exclusive access to one of the most stunning shared lakefront areas, featuring a level shoreline, picnic pavilion, ample parking, and easy entry for kayaks, canoes, swimming, and

    Justin Liller Railey Realty, Inc.

    180 Paradise Ridge Rd, 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
  • 1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    /93

    $829,000

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft

    1001 Sutter Ln, Oakland, MD 21550

    Discover the ultimate mountain–lake getaway in this stunning 5BR Southern-style home on a private 2.4-acre wooded lot bordering Broadford Lake recreational area! Located just minutes from Deep Creek Lake and Wisp Resort, this magnificent property offers over 6,500 sq ft. and delivers unforgettable space, luxury, and privacy. Step inside to soaring cathedral ceilings, skylights, oak floors, and a

    Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, Oakland, MD 21550
  • 155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    /51

    $674,900

    • 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
  • 340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    /87

    $949,900

    • 6 Beds
    • 4 Baths
    • 2,536 Sq Ft

    340 Grandview Dr, Oakland, MD 21550

    Lake Access property overlooking Cherry Creek Cove in the coveted Mountainside community, at 2,536 square feet, this fully furnished retreat pairs modern comfort with timeless mountain style. Freshly updated from top to bottom, with a new roof and deck staining, every detail feels dialed in. A wall of glass and open layout connects bright gathering spaces with panoramic lake views that steal the

    Jon Bell Railey Realty, Inc.

    340 Grandview Dr, Oakland, MD 21550
  • 220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    /85

    $775,000

    • 5 Beds
    • 3 Baths
    • 2,660 Sq Ft

    220 Woodlands Hill Ln, Oakland, MD 21550

    Discover this spacious 5-bedroom, 3-bath chalet in The View community at Deep Creek Lake, offering three finished levels of comfortable living and a strong history as the well-known rental 'Divided Sky'. The foyer greets you with a beautiful built-in for hanging jackets, leave your ski boots on the convenient tile floor and proceed in to the main level, where two-story ceilings paneled in solid

    Ana Dubin RE/MAX Realty Group

    220 Woodlands Hill Ln, 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
  • 77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, Oakland, MD 21550
    /65

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft

    77 Meadow Ct, Oakland, MD 21550

    Lake Access Chalet at Deep Creek Lake – Featured on HGTV’s Lakefront Bargain Hunt, this property is quietly tucked away on over half an acre on rolling mountain pasture in the sought after Paradise Ridge community, and pairs rustic comfort with clean, modern lines. Warm wood tones, vaulted ceilings, and a two-story stone fireplace anchor the main level. Open kitchen and dining area flow into a

    Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
  • 16 Lemley Dr, Oakland, MD 21550
    16 Lemley Dr, Oakland, MD 21550
    16 Lemley Dr, Oakland, MD 21550
    /62

    $399,000

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    16 Lemley Dr, Oakland, MD 21550

    Nestled in the serene community of Roman Nose Spa at Deep Creek Lake, this charming contemporary home offers a perfect blend of comfort and style and makes a great basecamp. With 4 beds and 2 1/2 baths and a thoughtfully designed living space, ideal for both relaxation and entertaining. Enjoy breathtaking views of Deep Creek Lake and the surrounding mountains from your backyard, where outdoor

    Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, Oakland, MD 21550
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /45

    $1,329,000

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

    $599,900

    • 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
  • 336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    /94

    $1,499,000

    • 5 Beds
    • 3 Baths
    • 2,826 Sq Ft

    336 Paradise Heights, Oakland, MD 21550

    Architecturally unique, private and spacious lakefront home with a perfect central location! Step into a home that blends striking architectural design with the best of lake living. The living room showcases a dramatic wall of glass and a floor-to-ceiling stone fireplace, while a large glass-walled rec room on the lower level offers another light-filled space to relax or entertain. This

    Susan Bell Railey Realty, Inc.

    336 Paradise Heights, 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

    $759,900

    • 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
  • 20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    /68

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550

    Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace,

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    5024 Cranesville Rd, Oakland, MD 21550

    Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1.68-acre hillside in a beautiful conservation area, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence.Inside, the main level features a spacious primary suite with a jetted tub, double vanity, and shower, a

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • 282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    /150

    $4,200,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 4,354 Sq Ft

    282 McComas Beach Terrace, Oakland, MD 21550

    Discover The Birch Bower, a rare architect-designed lakefront sanctuary offering 600 feet of private shoreline on Deep Creek Lake. Completed in 2021, this 6-bedroom, 5.5-bath residence exemplifies modern luxury, combining meticulous design, serene natural surroundings, and proven short-term rental performance. Offered turn-key and fully furnished, this extraordinary lakefront estate presents a

    Morgan Boyer Hunt Country Sotheby's International Realty

    282 McComas Beach Terrace, Oakland, MD 21550
  • 2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    /11

    $199,900

    • Land
    • 0.11 Acre
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • 41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    /103

    $2,399,000 Pre-Foreclosure

    • 7 Beds
    • 5 Baths
    • 4,691 Sq Ft

    41 Boyd Paugh Ln, Oakland, MD 21550

    Gorgeous 7 bedroom home with dock slip! This newer construction home sits on a quiet corner of Deep Creek Lake with 200 feet of lake frontage. Located in the beautiful and quiet Heron Cove community and comes with two community lake access points, one with a sandy beach area, tennis courts, and walking trails. The level lot is surrounded by trees and designed for privacy and outdoor enjoyment,

    Rachel Bruch Railey Realty, Inc.

    41 Boyd Paugh Ln, Oakland, MD 21550
  • 3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    /31

    $1,800,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    One of a kind 4 BR 4 BA brick Home. 5,100 sq. ft. + 3 car garage. Situated on 23.47 elevated acres with unbelievable panoramic views of Pleasant Valley and surrounding farming community. Living area on one level with full unfinished basement. Views from every room. Massive amount of closet space The opportunities are abundant with this property.

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /50

    $529,900

    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • 0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    /55

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft

    0 Crosby Dr Unit 64/65, Oakland, MD 21550

    TO BE BUILT on lots 64 & 65 Country Club Acres - 3BR, 2BA new construction with full walkout basement & attached 2 car garage fronting on hole #13 of the Oakland golf course. Impressive views from .61+/- acres of land, rare privacy and modern floor plan. 1,986 sf of finished living space on the first floor and 1,986 sq ft unfinished basement will have a full bath rough-in and can be finished

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Crosby Dr Unit 64/65, Oakland, MD 21550
  • 0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    /6

    $119,000

    • Land
    • 3.1 Acres
    • $38,387 per Acre

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 29 is located in a subdivision called the View, and it lives up to the name! Offering a generous 3.10 Acres with possible lake views this attractive location is close to lake amenities while giving a sense of privacy. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
  • 565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    /27

    $249,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 4

Maryland Garrett County Oakland

Real Estate & Homes for Sale in Oakland, MD

Why Live in Oakland

When people think of Maryland, the bustling city of Baltimore and the coastal capital of Annapolis often come to mind. But there’s much more to discover in the western portion of this state, particularly in the mountain city of Oakland. “Deep Creek ...

Learn more about living in Oakland

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $576,940.
Are home prices dropping in Oakland?
Yes, home prices in Oakland are down 3% in the last 12 months.
How many homes have sold over the last 12 months in Oakland, MD?
138 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 26705.
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 6.22%, your estimated principal and interest payment would be $2,210 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $95K a year to afford the median home price in Oakland. Learn how much home you can afford with our Home Affordability Calculator.
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.

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 87 days on the market compared to the national average of 53 days. The median sale price for homes in Oakland, MD over the last 12 months is $454,500, up 14% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$454,500
Median Single Family Sale Price
$447,000
Median Townhouse Sale Price
$485,000
Median 2 Bedroom Sale Price
$329,000
Median 1 Bedroom Sale Price
$249,900
Average Price Per Sq Ft
$264
Number of Homes for Sale
43
Last 12 months Home Sales
138
Months of Supply
3.70
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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