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Newest Homes for Sale in Oakland, MD

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  • 13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    /42

    $245,000

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    13 Laurel Brook Dr, Oakland, MD 21550

    Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

    Bill Weissgerber Railey Realty, Inc.

    13 Laurel Brook Dr, Oakland, MD 21550
  • 62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    /73

    $1,899,000

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

    62 Duck Cove Rd, Oakland, MD 21550

    One of Deep Creek Lake's most premium settings greets you on the point of this remarkable 4 bedroom, 4 bathroom lakefront home with 231' of level lakefront with eastern exposure, offering amazing sunrises looking down a long stretch of the lake toward Turkeyneck! 1 oversize attached garage space offers plenty of space for your vehicles on the street side and 2 attached garage spaces provide room

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-6601

    62 Duck Cove Rd, Oakland, MD 21550
  • 620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    /62

    $739,000

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    620 Crosby Dr, Oakland, MD 21550

    This stunning, recently built 4+ bedroom, 3.5 bath home in Country Club Acres offers modern design, thoughtful upgrades, and unmatched privacy on 3.43 wooded acres perched at the top of the mountain overlooking Oakland Golf Course and multiple ponds. The bright, open-concept layout is filled with natural light and features commercial-grade LVP flooring throughout, complemented by mid-range,

    Jay Ferguson Taylor Made Deep Creek Real Estate

    620 Crosby Dr, Oakland, MD 21550
  • 135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
    /22

    $294,999

    • 2 Beds
    • 1 Bath
    • 2,344 Sq Ft

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550

    Experience the best of lakeview living in this great condo at Deep Creek Lake. Offering two bedrooms, a fireplace and a lower-level family room for your enjoyment. Wake up to peaceful water views and enjoy ample space for everyday comfort and entertaining. The location is another plus, within walking distance to coffee shop, dining, and shopping. A perfect blend of size, scenery, and value!

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
  • 422 Maple Ave, Oakland, MD 21550
    422 Maple Ave, Oakland, MD 21550
    422 Maple Ave, Oakland, MD 21550
    /22

    $60,000

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft

    422 Maple Ave, Oakland, MD 21550

    Investor opportunity in a highly desirable location! This property has been gutted and is ready for your vision. A rare chance to renovate and customize to your exact specifications. Ideal for resale, rental investment, or personal use. Ideally located near Loch Lynn Heights Wetland Trails, soccer complex, and community park. Great potential for the right buyer. RAILEY REALTY IS NOT THE CARETAKER

    Nicole Jackson Railey Realty, Inc.

    422 Maple Ave, Oakland, MD 21550
  • 1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    /147

    $5,150,000 Coming Soon

    • 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 Reserve at

    Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550
  • 552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    /46

    $359,000 Coming Soon

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

    552 Black Oak Dr, Oakland, MD 21550

    Looking for a vacation spot or main living, Check out this nicely remolded home in a gated community. 3 bedrooms, 1 1/2 bathrooms, main level laundry room. Great rustic touches . Detached Garage with pellet stove. Yough Mountain Resort is the ultimate mountain escape! Nestled in a quiet, secluded area, this beautifully updated retreat offers modern comfort in a rustic Access to over 50 miles of

    Connie Leprevost Long & Foster Real Estate, Inc.

    552 Black Oak Dr, Oakland, MD 21550
  • 3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    /81

    $399,900

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    3930 Mayhew Inn Rd, Oakland, MD 21550

    2 for 1 on 2 .3 +/- acres! Remodeled 2BR 2BA cottage with auxiliary building that has an oversized garage, multiple workshop areas and 1BR 1BA apartment on the second level. New Maryland legislation, Accessory Dwelling Units Act of 2025, will allow expanded access to use the apartment above the garage in a more meaningful manner. Cabin boasts high end finishes and open living space with a cozy

    Jay Ferguson Taylor Made Deep Creek Real Estate

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • 1544 Stockslager Rd, Oakland, MD 21550
    1544 Stockslager Rd, Oakland, MD 21550
    1544 Stockslager Rd, Oakland, MD 21550
    /63

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 3,456 Sq Ft

    1544 Stockslager Rd, Oakland, MD 21550

    Enjoy lakefront living at its finest in this beautifully remodeled home with a private dock. Thoughtfully updated with modern finishes including a kitchen remodel, new windows and doors, new upper balcony, new flooring throughout, and recently added mini splits on the lower level. This property offers stunning water views, an open-concept layout, five bedrooms (three of which are en suites), and

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    1544 Stockslager Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    /55

    $329,900

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    565 Glendale Rd Unit 125, Oakland, MD 21550

    Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks,

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • 407 Seneca Ave, Oakland, MD 21550
    407 Seneca Ave, Oakland, MD 21550
    407 Seneca Ave, Oakland, MD 21550
    /37

    $219,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    407 Seneca Ave, Oakland, MD 21550

    Move right into this charming ranch style home offering comfortable one-level living! Recent improvements include a brand-new roof and fresh carpet throughout, giving the home a clean, updated feel. Offering three bedrooms and a wood burning fireplace which just adds to the warmth and coziness. The level yard provides great space for relaxing and entertaining family and friends. The location is

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    407 Seneca Ave, Oakland, MD 21550
  • 1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, Oakland, MD 21550
    /69

    $2,100,000 Open Sat 10AM - 2PM

    • 5 Beds
    • 5 Baths
    • 4,074 Sq Ft

    1038 S Blakeslee Rd, Oakland, MD 21550

    Welcome to 1038 S Blakeslee Road! A spacious lakefront retreat on Deep Creek Lake offering effortless lakeside living. A Rare opportunity to own in one of Deep Creek’s most sought-after lakeside communities. This five-bedroom, five-bath home sits on a large 1.11-acre level lot with easy access to the water and generous outdoor space for recreation and entertaining. Inside, the home is warm and

    Eric Crawford Taylor Made Deep Creek Real Estate

    1038 S Blakeslee Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 124, Oakland, MD 21550
    565 Glendale Rd Unit 124, Oakland, MD 21550
    565 Glendale Rd Unit 124, Oakland, MD 21550
    /30

    $159,000

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

    565 Glendale Rd Unit 124, Oakland, MD 21550

    Public: If you are looking for an affordable way to own at Deep Creek Lake, this is it! This Silver Tree Suites unit is is main floor and beautiful. .Offering a king size bed, and a propane fireplace. The hotel offers a sitting area, sauna and workout area for your enjoyment. The Dutch's restaurant & Harbor Bar are just steps away, offering wonderful dining options while never having to leave the

    ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    565 Glendale Rd Unit 124, Oakland, MD 21550
  • 0 Cub Dr, Oakland, MD 21550
    0 Cub Dr, Oakland, MD 21550
    0 Cub Dr, Oakland, MD 21550
    /13

    $29,999

    • Land
    • 1.93 Acres
    • $15,544 per Acre

    0 Cub Dr, Oakland, MD 21550

    Make an offer, buy it now. +/- 1.93 Acre lot of land in Garrett County. Close to the West Virginia Border. Easy access to major traffic artery Cranesville Rd. Parcel is vacant.

    Adam Shpritz

    0 Cub Dr, Oakland, MD 21550
  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /67

    $525,000

    • 2 Beds
    • 2 Baths
    • 4,720 Sq Ft

    355 Lonesome Pine Rd, Oakland, MD 21550

    Welcome to your own slice of paradise—this stunning home sits on 84 breathtaking acres with incredible water frontage, offering unmatched privacy and a true connection to nature. Step inside and be captivated by walls of windows that flood the home with natural light, creating a warm and inviting atmosphere throughout the expansive living spaces. Whether you're entertaining or simply relaxing,

    Sheila Howell Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • 1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    /61

    $379,000

    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Picture perfect log cabin on 11 private, wooded acres in the gated Timbers on the Yough community featuring Youghiogheny River access. This inviting home features a metal roof, spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. The primary bath offers dual sinks, an oversized soaking tub, dual shower heads and radiant floor heat!Recent updates

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, Oakland, MD 21550
  • 891 Mountainview Dr, Oakland, MD 21550
    891 Mountainview Dr, Oakland, MD 21550
    891 Mountainview Dr, Oakland, MD 21550
    /6

    $875,000 Coming Soon

    • 3 Beds
    • 4 Baths
    • 3,990 Sq Ft

    891 Mountainview Dr, Oakland, MD 21550

    Discover the perfect blend of rustic charm and modern comfort in this inviting turnkey 3‐bedroom mountaintop chalet, set on 1.17 private acres with expansive outdoor entertainment space. Whether you're hosting friends or enjoying quiet mountain evenings, this fully-furnished home delivers an unforgettable retreat. Inside, the great room impresses with a soaring stacked‐stone fireplace. The

    Brent Housley Railey Realty, Inc.

    891 Mountainview Dr, Oakland, MD 21550
  • 0 Hoye St, Oakland, MD 21550
    0 Hoye St, Oakland, MD 21550
    0 Hoye St, Oakland, MD 21550
    /8

    $25,000

    • Land
    • 3 Acres
    • $8,333 per Acre

    0 Hoye St, Oakland, MD 21550

    Make an offer, buy it now +/- 2.96 Acre lot of land in Garrett County. Close to the West Virginias Border. Easy access to major traffic artery Seneca Trail Highway. Parcel is vacant. Deposit is $5,000

    Adam Shpritz

    0 Hoye St, Oakland, MD 21550
  • 0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550
    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550
    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550
    /10

    $99,900

    • Land
    • 1.7 Acres
    • $58,765 per Acre

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550

    Ready to bring your Deep Creek Lake dream home to life? This beautiful 1.7-acre lot in the sought after community of Paradise Ridge offers the perfect blend of peace, privacy, and lake access. Spend your summer days down by the water, where owners enjoy access to one of the area’s best lakefront spots, complete with a sandy beach, picnic pavilions, and kayak or swimming areas. When the day winds

    Eric Crawford Taylor Made Deep Creek Real Estate

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550
  • 226 N Hammond St, Oakland, MD 21550
    226 N Hammond St, Oakland, MD 21550
    226 N Hammond St, Oakland, MD 21550
    /19

    $289,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    226 N Hammond St, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! This 2BR/2BA, 1000sf cottage is located in the historic 2nd Street area of Oakland and features modern design with elite finishes. Key features include Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and drawers, quartz counters and range backsplash, shiplap backsplash accents, stainless steel Frigidaire

    Jay Ferguson Taylor Made Deep Creek Real Estate

    226 N Hammond St, Oakland, MD 21550
  • 163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    /62

    $314,000

    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, Oakland, MD 21550
  • 24 Trailside Way, Oakland, MD 21550
    24 Trailside Way, Oakland, MD 21550
    24 Trailside Way, Oakland, MD 21550
    /43

    $555,000

    • 4 Beds
    • 3.5 Baths
    • 2,430 Sq Ft

    24 Trailside Way, Oakland, MD 21550

    Tucked in the Silver Ridge community at Deep Creek Lake, this inviting home blends rustic charm with comfortable modern living. Community trails and shared green space offer opportunities for outdoor recreation, while the wooded setting behind the home provides a sense of privacy and a peaceful natural backdrop. Step inside to an interior that reflects its surroundings, where warm wood accents,

    Jackie Ball Daley Northrop Realty

    24 Trailside Way, Oakland, MD 21550
  • 0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
    /20

    $160,000

    • Land
    • 10.1 Acres
    • $15,842 per Acre

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550

    Over 10 acres ready for developing off Dennett Rd. and Oakland Ave. Can be subdivided or could be large parcel to build your dream home, privacy off main streets with 3 separate entrances connecting to town roads. Engineered drawings for subdivision with grading permit in place at time of survey, is available and will be transferred with sale. (Potential up to 20 lots) Public sewar & water can be

    Julie Mead The KW Collective

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
  • 1307 Broadford Rd, Oakland, MD 21550
    1307 Broadford Rd, Oakland, MD 21550
    1307 Broadford Rd, Oakland, MD 21550
    /22

    $207,500

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    1307 Broadford Rd, Oakland, MD 21550

    Nestled in the scenic countryside of Oakland, this charming ready to move in 2 bed 1 Bath home offers the perfect blend of privacy, space, and small-town convenience. Situated on a beautiful property along Broadford Road, the home provides peaceful surroundings while remaining just minutes from downtown Oakland, schools, shopping, and plenty of outdoor recreation areas.. Properties in this area

    Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, Oakland, MD 21550
  • 449 S 3rd St, Oakland, MD 21550
    449 S 3rd St, Oakland, MD 21550
    449 S 3rd St, Oakland, MD 21550
    /64

    $275,900

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft

    449 S 3rd St, Oakland, MD 21550

    Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic

    Justin Liller Railey Realty, Inc.

    449 S 3rd St, Oakland, MD 21550
  • 3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, Oakland, MD 21550
    3749 Maryland Hwy, Oakland, MD 21550
    /43

    $325,000

    • 2 Beds
    • 2 Baths
    • 2,015 Sq Ft

    3749 Maryland Hwy, Oakland, MD 21550

    Set on a beautiful lot in Deep Creek, Maryland, this stunning property offers the perfect blend of privacy, relaxation, and investment potential. Currently enjoyed as a second home, the residence has also been successfully utilized as a partial Airbnb, generating approximately $28,000 in rental income last year. The home has been thoughtfully updated, creating a warm and inviting atmosphere with

    Jovan Vidulovic Keller Williams Realty

    3749 Maryland Hwy, Oakland, MD 21550
  • 53 Bird Ave, Oakland, MD 21550
    53 Bird Ave, Oakland, MD 21550
    53 Bird Ave, Oakland, MD 21550
    /34

    $239,700

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    53 Bird Ave, Oakland, MD 21550

    Opportunity and a peaceful country setting on 1.55 acres in Deer Park. This 3BR, 2BA ranch offers 1,872 sq ft with solid bones and room to make it your own. The spacious kitchen with hickory cabinets, gas stove, and propane fireplace creates a warm gathering space at the heart of the home. Outside, several outbuildings—including a large shop and secondary wood shop with heat and electric, a

    Rachel Bruch Railey Realty, Inc.

    53 Bird Ave, Oakland, MD 21550
  • 141 Montana Ln, Oakland, MD 21550
    141 Montana Ln, Oakland, MD 21550
    141 Montana Ln, Oakland, MD 21550
    /57

    $219,000

    • 1 Bed
    • 1.5 Baths
    • 912 Sq Ft

    141 Montana Ln, Oakland, MD 21550

    Nestled on nearly 3 acres across two parcels, this chalet-style home offers a rare opportunity to create your retreat just minutes from the lake. Renovate the existing structure, or start fresh and build the lake-area retreat or cabin you’ve always imagined. The level, wooded setting provides privacy, peace, and plenty of room to expand, garden, or simply enjoy nature. With well and septic

    Larry Smith Railey Realty, Inc.

    141 Montana Ln, Oakland, MD 21550
  • 164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    /50

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    164 Grandview Dr, Oakland, MD 21550

    Experience mountain living at its finest in this breathtaking mountaintop home overlooking Deep Creek Lake. With sweeping views from almost every room, your hardest decision may be where to sit to enjoy them. Offering three levels of living space, hardwood floors ( which were recently refinished), and some new appliances. The multiple decks are ideal to enjoy family and friends while taking in

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    164 Grandview Dr, Oakland, MD 21550
  • 74 Parks Rd, Oakland, MD 21550
    74 Parks Rd, Oakland, MD 21550
    /2

    $69,900

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    74 Parks Rd, Oakland, MD 21550

    **Investor Special with Mountain & Water Views**Opportunity is knocking at 74 Parks Road in Oakland, Maryland! This 3-bedroom, 1-bath one story is perfectly positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region.Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from

    Emillie Albrecht Real Broker, LLC

    74 Parks Rd, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    /28

    $299,000

    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

    Nestled in the charming Traders Landing community, this delightful end-of-row townhouse offers a perfect blend of comfort and convenience with one of the best unobstructed views of the lake in Traders Landing. This villa-style home features two cozy bedrooms and a full bathroom, ideal for relaxation and unwinding after a long day. The inviting living space is enhanced by a warm wood-burning

    Agent Photo

    James Matthews

    Taylor Made Deep Creek Real Estate

    (240) 883-5848

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • 233 Rhododendron Dr, Oakland, MD 21550
    233 Rhododendron Dr, Oakland, MD 21550
    233 Rhododendron Dr, Oakland, MD 21550
    /17

    $35,000

    • Land
    • 1.92 Acres
    • $18,229 per Acre

    233 Rhododendron Dr, Oakland, MD 21550

    Fantastic opportunity in the gated community of Youghiogheny Mountain Resort. This 1.92-acre lot is perfect for outdoor enthusiasts, offering ATV riding, hunting, fishing, and more. Build your dream home or a recreational retreat. Approved for a 2-bedroom conventional system, with the option to expand using a sand mound system. Located just minutes from Wisp Resort, Deep Creek Lake, Herrington

    Laura Newhall Taylor Made Deep Creek Real Estate

    233 Rhododendron Dr, Oakland, MD 21550
  • 654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    /17

    $449,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines MAJESTIC scenic views with modern design, elite finishes and outdoor living. Key features include multiple wood-burning fireplaces (inside + out), Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets

    Jay Ferguson Taylor Made Deep Creek Real Estate

    654 N Bradley Ln, Oakland, MD 21550
  • 505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    /38

    $292,500

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    505 Southern Pines Dr, Oakland, MD 21550

    Charming ranch-style home located in the desirable Southern Pines neighborhood. From the moment you enter, you’ll appreciate the warm and inviting feel of the open layout. The main level features three comfortable bedrooms, two full bathrooms, beautiful hardwood flooring, and a seamless kitchen, living, and dining area that creates an ideal space for everyday living and entertaining. The recently

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    505 Southern Pines Dr, Oakland, MD 21550
  • 820 N 4th St, Oakland, MD 21550
    820 N 4th St, Oakland, MD 21550
    820 N 4th St, Oakland, MD 21550
    /19

    $60,000

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    820 N 4th St, Oakland, MD 21550

    Step into potential with this 2 bed, 1 bath home being sold AS IS. Located in a convenient community with town water & sewer, this property offers a blank canvas for the savvy buyer or investor ready to bring a vision to life. The house has been gutted and is ready for the new owner to start the renovation, providing a clear interior and a fresh slate to customize the layout, finishes, and

    Duane Stein II The KW Collective

    820 N 4th St, Oakland, MD 21550
  • TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550
    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550
    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550
    /5

    $89,900

    • Land
    • 15.75 Acres
    • $5,708 per Acre

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550

    Tucked away just minutes from town, this 15.75± acre wooded parcel offers a quiet country setting with the privacy many buyers are searching for. Located off Bethlehem Road near the Potomac State Forest, the property features largely level terrain, mature trees, and abundant wildlife—an ideal backdrop for a private residence, weekend retreat, or recreational use. The surrounding area provides

    Thomas Long Railey Realty, Inc.

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550
  • 62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    /77

    $930,000

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

    62 Whispering Pines Ln, Oakland, MD 21550

    Tucked away on just over 7 acres of serene, wooded privacy, this stunning custom Yellowstone log home offers the perfect blend of rustic charm and modern comfort—just minutes from Swallow Falls State Park and only 10 minutes to Deep Creek Lake and Wisp Resort. The inviting open main level is designed for effortless entertaining, highlighted by a warm gas fireplace in the family room, a spacious

    Justin Liller Railey Realty, Inc.

    62 Whispering Pines Ln, Oakland, MD 21550
  • 313 W Liberty St, Oakland, MD 21550
    313 W Liberty St, Oakland, MD 21550
    313 W Liberty St, Oakland, MD 21550
    /59

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft

    313 W Liberty St, Oakland, MD 21550

    Charming and meticulously maintained 1947 brick ranch located at the edge of Oakland town limits on a beautiful 1⁄4-acre lot. This 2-bedroom, 1-bath home features spacious rooms, natural gas heat, public utilities, and a full unfinished basement offering great storage or future potential. Ownership includes a 1⁄2 interest in a shared 2-car garage. Conveniently situated near schools, the hospital,

    Justin Liller Railey Realty, Inc.

    313 W Liberty St, Oakland, MD 21550
  • 467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    /60

    $799,900

    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft

    467 Paradise Ridge Rd, Oakland, MD 21550

    Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of the hill on 1.29 acres, this 4-bedroom, 3 full and 1 half bath retreat offers 3,780 finished square feet across three levels. Abundant glass frames the surrounding ridgelines with views of Deep Creek Lake from every room in the house!

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • 8 Laurel Brook Dr, Oakland, MD 21550
    8 Laurel Brook Dr, Oakland, MD 21550
    8 Laurel Brook Dr, Oakland, MD 21550
    /30

    $284,900

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    8 Laurel Brook Dr, Oakland, MD 21550

    Re-positioned price to sell. Beautiful Renovated 2-bedroom, 2-bath condo is Turnkey Ready Now for Part-time, Full-time Living or Rental, located in this quiet desirable Laurel Brook community, close to the lake, local activities, and everyday amenities. Warm, welcoming, and filled with natural light, the home features mountain views and a skylight in the living room that enhances the open airy

    Karen Hart Cummings & Co. Realtors

    8 Laurel Brook Dr, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 4

Maryland Garrett County Oakland

Newest Listings for Sale in Oakland, MD

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $539,208.
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?
140 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 $405,000. If you put a 20% down payment of $81,000 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $2,020 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $87K 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 96 days on the market compared to the national average of 55 days. The median sale price for homes in Oakland, MD over the last 12 months is $413,500, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$413,500
Median Single Family Sale Price
$399,900
Median Townhouse Sale Price
$472,500
Median 2 Bedroom Sale Price
$310,250
Median 1 Bedroom Sale Price
$217,450
Average Price Per Sq Ft
$259
Number of Homes for Sale
53
Last 12 months Home Sales
140
Months of Supply
4.50
Median List Price
$405,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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