86

Oakland, MD Homes for Sale with Acreage

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  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /61

    $835,000

    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Coming Soon! Beautifully maintained 5 bedroom 5 bathroom lake area chalet. Beautifully landscaped and situated on 4 +/- acres with partial views of the south side of Deep Creek Lake. This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished living space. Featuring a large heated garage with multiple car storage and additional

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    198 Grandview Dr, Oakland, MD 21550
    /45

    $825,000

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

    198 Grandview Dr, Oakland, MD 21550

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

    Heather Taylor RE/MAX One

    198 Grandview Dr, Oakland, MD 21550
  • 186 Thornberry Rd, Oakland, MD 21550
    186 Thornberry Rd, Oakland, MD 21550
    186 Thornberry Rd, Oakland, MD 21550
    /74

    $995,000

    • 5 Beds
    • 3.5 Baths
    • 2,347 Sq Ft

    186 Thornberry Rd, Oakland, MD 21550

    186 Thornberry is a lovely lake access contemporary in the much sought after Blakeslee community on the shores of Deep Creek Lake. This home feels warm and inviting from the moment you pull in the driveway. The detail to the landscaping and beautiful shrubbery makes a very nice first impression. Upon entering, the layout flows very nicely with two stone wood burning fireplaces, a great enclosed

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    186 Thornberry Rd, Oakland, MD 21550
  • 1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    /94

    $899,900

    • 5 Beds
    • 6 Baths
    • 6,588 Sq Ft

    1001 Sutter Ln, Oakland, MD 21550

    Set on a serene 2.4-acre wooded lot, this thoughtfully crafted Southern-inspired property offers exceptional privacy while placing you minutes from the region’s most popular destinations—including Deep Creek Lake, Wisp Resort, Broadford Lake Park, and everyday essentials like shopping and medical care. Built to accommodate both relaxation and entertaining on a grand scale, the home offers 5

    Jackie Ball Daley Northrop Realty

    1001 Sutter Ln, Oakland, MD 21550
  • 62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    /67

    $829,900

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft

    62 Middleton Rd, Oakland, MD 21550

    Tucked in the trees at The Blakeslee, this 3-bed, 2.5-bath home delivers space, style, and a dock slip just down the road! Fresh interior paint throughout. Beautiful sunroom soaked in light—easily the best room in the house. Spacious back deck and brand-new hot tub make the outdoor setup just as strong. Inside, you’ve got a pass-through stone fireplace, stainless appliances, central A/C, and a

    Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
  • 969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, Oakland, MD 21550
    /56

    $725,000

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft

    969 Hoyes Run Rd, Oakland, MD 21550

    Tucked among towering pines and hardwoods, this fully TURN KEY 5-bedroom log chalet blends natural beauty with cozy, upscale charm. The home sits on a gentle slope overlooking a meandering stream, its melodic sounds carrying through the trees and adding a tranquil soundtrack to life. A wraparound deck offers views of the forest and stream bank. Inside, the open floor plan welcomes you with a

    Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /22

    $650,000

    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    355 Lonesome Pine Rd, Oakland, MD 21550

    Escape to your own private mountain retreat! This contemporary 2-bed, 2-bath home is perfectly situated on approximately 84 acres of pristine land, offering breathtaking views overlooking a picturesque 7-acre field. Expansive windows, high vaulted ceilings and an open layout maximize the stunning scenery, allowing natural light to flood the space. Whether you're seeking a peaceful getaway, an

    Brody Monahan Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • 6652 George Washington Hwy, Oakland, MD 21550
    6652 George Washington Hwy, Oakland, MD 21550
    6652 George Washington Hwy, Oakland, MD 21550
    /33

    $695,000

    • 6 Beds
    • 2.5 Baths
    • 2,672 Sq Ft

    6652 George Washington Hwy, Oakland, MD 21550

    Beautiful home sitting on 35 acres, built by the current owners. Enter the main level into a grand foyer, with a lofty ceiling and beautiful chandelier. To the left is a separate dining room which leads to the large kitchen and living room. Off the living room is the primary bedroom with a huge walk-in closet and a full bathroom, including a newly installed walk-in shower. On the other side of

    Andrew Orr Railey Realty, Inc.

    6652 George Washington Hwy, Oakland, MD 21550
  • 98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    /27

    $268,900

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    98 Bear Run Rd, Oakland, MD 21550

    TIRED OF CITY LIVING? ENJOY PLENTY OF ROOM TO ROAM ON THIS 2 ACRE TRACT WHICH INCLUDES A “FULLY FURNISHED” (26’ X 42’) 3 BR, 2 BA RANCHER (D-WIDE) W VINYL SIDING, SHINGLE ROOF, LGE COVERED FRONT PORCH, REAR ENCLOSED PORCH, CONCRETE BLOCK FOUNDATION AND 8-10 GRAVEL PARKING AREA. INTERIOR OFFERS A SPACIOUS LIV RM W CEILING FAN/LIGHT, W-W CARPET & PANEL WALLS. EAT-IN KIT W ALL APPLIANCES, TABLE &

    Mike Haywood The Mike Haywood Group

    98 Bear Run Rd, Oakland, MD 21550
  • 5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    /38

    $259,000

    • 3 Beds
    • 1 Bath
    • 1,199 Sq Ft

    5202 Hutton Rd, Oakland, MD 21550

    Charming ranch-style home offering 3 bedrooms, 1 full bath, and loads of potential! This one-level home sits on over 12 beautiful acres, providing plenty of space for outdoor activities, gardening, or even future expansion. The attached garage adds convenience, and the layout makes for easy, comfortable living. While the home does need some TLC, it’s priced to sell and perfect for those looking

    Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
  • Lot 53 Mountainview Dr, Oakland, MD 21550
    Lot 53 Mountainview Dr, Oakland, MD 21550
    Lot 53 Mountainview Dr, Oakland, MD 21550
    /5

    $124,900

    • Land
    • 1.02 Acres
    • $122,451 per Acre

    Lot 53 Mountainview Dr, Oakland, MD 21550

    Ready to build lot in Deep Creek Lake's Mountainside Subdivision. This wooded lot is relatively level can be connected to public water and has an approved percolation test for an onsite septic system. Build you dream home in this mountaintop community with homes values ranging up to $2,000,000.

    Richard Saunders Samson Properties

    Lot 53 Mountainview Dr, Oakland, MD 21550
  • Lot 7 Backbone Ridge Rd, Oakland, MD 21550
    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
    /7

    $29,950

    • Land
    • 4.00 Acres
    • $7,488 per Acre

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550

    This 4-acre building lot in the Backbone Ridge community offers breathtaking mountain views and a 3-bedroom perc approval — ready for your dream home. Perfectly positioned near Deep Creek Lake, WISP Ski Resort, Canaan Valley, Timberline Ski Resort, and Blackwater Falls State Park, outdoor adventure is just minutes away. Whether you're building a year-round residence or a weekend escape, enjoy the

    Brent Housley Railey Realty, Inc.

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
  • 1260 Gnegy Church Rd, Oakland, MD 21550
    1260 Gnegy Church Rd, Oakland, MD 21550
    1260 Gnegy Church Rd, Oakland, MD 21550
    /58

    $449,000

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

    1260 Gnegy Church Rd, Oakland, MD 21550

    Discover space, privacy, and mountain charm on this stunning property nestled on over 76.03 +/- wooded acres. The home offers 3 bedrooms, 3 bathrooms, a spacious main level with open-concept living, and a partially finished upstairs ready for your personal touch. An attached garage, oversized detached garage, and expansive outdoor space provide endless possibilities—whether you’re seeking a

    Nina Beitzel Railey Realty, Inc.

    1260 Gnegy Church Rd, Oakland, MD 21550
  • 1570 Garrett Rd, Oakland, MD 21550
    1570 Garrett Rd, Oakland, MD 21550
    1570 Garrett Rd, Oakland, MD 21550
    /27

    $300,000

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    1570 Garrett Rd, Oakland, MD 21550

    Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, including a stream, pond, barn and outbuildings with many possibilities to include potential subdivision configurations. The log home needs some TLC and updates; it is being sold as part of an estate. Some items of personal property remain in the house and on grounds. Those items are being removed. More photos

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    1570 Garrett Rd, Oakland, MD 21550
  • 2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    /47

    $234,900

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2805 Shady Dell Rd, Oakland, MD 21550

    Nestled in the heart of Pleasant Valley, an area known for its peaceful country charm, this 4-bedroom, 2-bath home offers a serene setting. Enclosed decks run the full length of both the front and back of the house, with an additional private deck just off the dining room. The master bedroom features access to a covered deck and includes a full bathroom, while a second spacious bedroom also opens

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    2805 Shady Dell Rd, Oakland, MD 21550
  • 421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    /107

    $1,599,000

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft

    421 Penn Cove Rd, Oakland, MD 21550

    Exquisite Lakefront Log Home Retreat at Deep Creek Lake. Nestled on a private, wooded 1-acre lot with 169 feet of pristine lakefront along a serene cove on the southern end of Deep Creek Lake, this well-maintained log home offers the perfect balance of rustic charm and luxurious lakefront living. From the moment you arrive, the home’s park-like setting and lush landscaping welcome you

    Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
  • 0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
    /15

    $199,900

    • Land
    • 10 Acres
    • $20,737 per Acre

    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550

    A rare opportunity to acquire a high-potential 9.64 acre parcel located in the heart of Oakland. The location is very close to schools, grocery stores, restaurants, hospital and shopping. This site offers an ideal setting for residential, mixed-use, multifamily, or commercial development (subject to zoning approval). Easy access to infrastructure, with public utilities nearby at the street. This

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 8th & Dennett Road St Unit MDGA2009886, Oakland, MD 21550
  • 170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    /15

    $209,000

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    170 Tannery Rd, Oakland, MD 21550

    Charming Country Home with Pond, Views & Space to Grow! Welcome to your peaceful getaway just south of Oakland! This cozy and well-kept 3-bedroom, 2-bath home sits on 1.7 private acres and offers so much more than you’d expect — including your very own pond, with blooming lilies and fish you can catch right from your backyard. Built from solid concrete blocks and topped with a durable metal roof,

    Jonathan Minerick Homecoin.com

    170 Tannery Rd, Oakland, MD 21550
  • 8760 Oakland Sang Run Rd, Oakland, MD 21550
    8760 Oakland Sang Run Rd, Oakland, MD 21550
    8760 Oakland Sang Run Rd, Oakland, MD 21550
    /28

    $82,500

    • Land
    • 2.53 Acres
    • $32,609 per Acre

    8760 Oakland Sang Run Rd, Oakland, MD 21550

    Attention outdoor enthusiasts! This 2.53 acre lot just across the road from state-owned land down to the world-famous Youghiogheny River is a whitewater lover or fisherman's dream. Complete with a gravel driveway up to a flat gravel pad and electric meter ready to go, perfect for a camper or a forever home. Perc-approved for 3 bedrooms and less than half a mile from easy public Yough access.

    Elizabeth Ware Railey Realty, Inc.

    8760 Oakland Sang Run Rd, Oakland, MD 21550
  • 609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    /59

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,030 Sq Ft

    609 Southern Pines Dr, Oakland, MD 21550

    Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built traditional-style residence combines comfort, and convenience. Just minutes from Broadford Lake Park, healthcare, shopping, Deep Creek Lake, and Wisp Ski Resort, this peaceful property offers easy access to all the local amenities. Two story stone & cedar, 4BR, 2.5 Bath w/ 2 - car attached garage, & 2 - car

    Brian Covell BHHS Touchdown Home Pros Realty

    609 Southern Pines Dr, Oakland, MD 21550
  • Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    /9

    $35,000

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

    Lot 15 Little Mountain Rd, Oakland, MD 21550

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

    ADAM MURRAY BHHS Touchdown Home Pros Realty

    Lot 15 Little Mountain Rd, Oakland, MD 21550
  • 590 S Blakeslee Rd, Oakland, MD 21550
    590 S Blakeslee Rd, Oakland, MD 21550
    590 S Blakeslee Rd, Oakland, MD 21550
    /64

    $1,249,000

    • 4 Beds
    • 3.5 Baths
    • 3,071 Sq Ft

    590 S Blakeslee Rd, Oakland, MD 21550

    Nestled in the much sought after Blakeslee community you will find this lovely mountain retreat with lake access and exceptional amenities. This contemporary-style home is designed for both relaxation and entertainment, featuring a spacious open-concept layout, multiple family rooms, a large loft, and a well-appointed kitchen. Offering three levels of living space, hardwood flooring, quartz

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    590 S Blakeslee Rd, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 3

Maryland Garrett County Oakland

Homes for Sale with Acreage in Oakland, MD

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 $525,000, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$525,000
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
$373
Number of Homes for Sale
40
Last 12 months Home Sales
55
Months of Supply
8.70
Median List Price
$529,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 86 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Oakland, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Oakland and discover the potential and freedom that comes with owning your own piece of property.

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