54

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
    /107

    $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 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
  • 1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    /150

    $4,250,000

    • 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
  • Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    /31

    $130,000

    • Land
    • 2.1 Acres
    • $61,905 per Acre

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550

    Discover the perfect setting for your mountain retreat in the Paradise Ridge community at Deep Creek Lake. This beautiful 2.10 acre wooded lot is tucked away on a quiet cul-de-sac, offering privacy, natural surroundings, and a peaceful atmosphere. The property has already been approved for a conventional septic system, making it an ideal choice for building your dream home or vacation getaway.

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 526-7577

    Lot 20 Paradise Ridge 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
    /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
  • 220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    /85

    $750,000

    • 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 on over 2 acres of private woods!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 oak create an impressive

    Ana Dubin RE/MAX Realty Group

    220 Woodlands Hill Ln, 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
  • 336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    /94

    $1,449,000

    • 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
  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $399,000

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

    5024 Cranesville Rd, Oakland, MD 21550

    Just Reduced!! 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,

    Rich Orr Railey Realty, Inc.

    5024 Cranesville 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
    /123

    $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
  • 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
  • 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
  • 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
  • 697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    697 Monte Vista Rd, 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
  • 47 Ridgewood Dr, Oakland, MD 21550
    47 Ridgewood Dr, Oakland, MD 21550
    47 Ridgewood Dr, Oakland, MD 21550
    /29

    $219,900

    • Land
    • 1.1 Acres
    • $199,909 per Acre

    47 Ridgewood Dr, Oakland, MD 21550

    Prime Lake Access Lot in Mountainside – Perfect for Your Dream Home! Nestled on a one-acre wooded lot in the sought-after Mountainside community, this homesite offers breathtaking views of Deep Creek Lake and the ideal slope for a walk-out basement. Enjoy the best of four-season living with easy access to community lake privileges, state parks, restaurants, and WISP Resort. Plus, take advantage

    Mike Fenton Railey Realty, Inc.

    47 Ridgewood Dr, Oakland, MD 21550
  • 9 Timber Falls Rd, Oakland, MD 21550
    9 Timber Falls Rd, Oakland, MD 21550
    9 Timber Falls Rd, Oakland, MD 21550
    /25

    $34,000

    • Land
    • 6.9 Acres
    • $4,928 per Acre

    9 Timber Falls Rd, Oakland, MD 21550

    Buildable wooded lot on Backbone Ridge—approved for a 4-bedroom traditional septic system. Perfectly positioned between Canaan Valley and Deep Creek Lake, this property offers prime access to four-season adventure: hunting, hiking, skiing, and ATV riding. Minutes from Blackwater Falls, Whitegrass XC Ski Center, and the vibrant mountain towns of Thomas and Davis

    Jesse Shimrock Railey Realty, Inc.

    9 Timber Falls Rd, Oakland, MD 21550
  • 0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
    /3

    $135,000

    • Land
    • 1 Acre
    • $135,000 per Acre

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550

    Centrally located 1-acre lake access homesite with a dock slip! This property has endless possibilities to build, and depending on where you decide to position your new home, there could be potential for lake views. Offering public sewer and no HOA fees. The only decision left to be made is what style home you will build. Just minutes to the DCL State Park, several restaurants, convenience store,

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
  • 0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    /2

    $149,000

    • Land
    • 1 Acre
    • $149,000 per Acre

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550

    Wooded lot with spectacular views of Paradise Point area of lake. Great privacy. Sewer tap available

    John Zorzit Eagle Commercial Realty

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
  • 511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    /33

    $180,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is located on the southwest corner of Maryland Highway, State Route 135 and Main Street, Deer Park. It is 2.5 acres, more or less, which is part of Parcel 0069 Map 0073, containing 32.20 acres, more or less. The remaining 30.00 acres on the northwest side of Route 135 is not included. The 2.5 acres is an estimate of area and is subject to a survey for verification.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • 0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
    /6

    $119,000

    • Land
    • 3.05 Acres
    • $39,016 per Acre

    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 28 located in a subdivision called the view, it lives up to the name and offers 3.05 Acres. Prime location for a vacation rental, second home, or primary residence with filtered lake and mountain views. Northwestern orientation offers a chance for beautiful sunset views. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 28 Briarwood Ln Unit MDGA2008896, 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 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
  • LOT 25 Holy Cross Dr, Oakland, MD 21550
    LOT 25 Holy Cross Dr, Oakland, MD 21550
    LOT 25 Holy Cross Dr, Oakland, MD 21550
    /25

    $499,999

    • Land
    • 1.34 Acres
    • $373,134 per Acre

    LOT 25 Holy Cross Dr, Oakland, MD 21550

    Discover the perfect blend of privacy, prestige, and natural beauty with Lot 25 in The Reserve at Holy Cross—a premier wooded lakefront homesite tucked into a serene private cove on Deep Creek Lake. Boasting 1.34 acres and an impressive 251 feet of lake frontage, this exceptional lot offers the ideal setting to build your dream retreat. Enjoy direct access to the water with two dedicated boat

    Steven Ritchie Railey Realty, Inc.

    LOT 25 Holy Cross Dr, Oakland, MD 21550
  • Lot G Randall Way, Oakland, MD 21550
    Lot G Randall Way, Oakland, MD 21550
    Lot G Randall Way, Oakland, MD 21550
    /10

    $250,000

    • Land
    • 2.07 Acres
    • $120,773 per Acre

    Lot G Randall Way, Oakland, MD 21550

    Pergin Farm lake access lot with 2 acres and one boat slip. A private wooded setting in one of Deep Creeks most desirable, warm, and inviting locations.

    Russell Bounds Railey Realty, Inc.

    Lot G Randall Way, Oakland, MD 21550
  • Lot 1 Cherrywood Dr, Oakland, MD 21550
    Lot 1 Cherrywood Dr, Oakland, MD 21550
    Lot 1 Cherrywood Dr, Oakland, MD 21550
    /17

    $38,000

    • Land
    • 3.03 Acres
    • $12,541 per Acre

    Lot 1 Cherrywood Dr, Oakland, MD 21550

    ****NOW ONLY $38,000!! Discover the perfect blend of space, privacy, and convenience with this 3.03 acre lot, a short drive from downtown Oakland, Deep Creek Lake, Potomac State Forest and Garrett State Forest! With a 5-bedroom perc on file, this property is ready for your dream home. This beautiful property is located in Cherrywood Ridge Subdivision, with only 7 lots in the community.

    Amy Skipper Railey Realty, Inc.

    Lot 1 Cherrywood Dr, Oakland, MD 21550
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /67

    $769,000

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

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    With a new price you don't want to miss this chance! 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. Recently Professionally appraised for $868,000! This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, Oakland, MD 21550
    /19

    $295,000

    • Land
    • 8.48 Acres
    • $34,788 per Acre

    26 Green Brier Rd, Oakland, MD 21550

    8.48± acres offering excellent commercial or residential potential. Property features an existing well and septic system, with easy access and outstanding visibility. Conveniently located just minutes from the Oakland city limits outside of Zoning Districts. Ideal opportunity for development or investment.

    Rich Orr Railey Realty, Inc.

    26 Green Brier Rd, Oakland, MD 21550
  • 0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    /26

    $699,000

    • Land
    • 33.93 Acres
    • $20,601 per Acre

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550

    Incredible Development Opportunity! Almost 34 acres of beautiful grounds zoned Residential/Industrial/Professional (RIP). This parcel would make a beautiful site for a single family or condo/townhome subdivision, business park, or industrial complex. Or, build your dream home with over 33 acres of privacy, yet close to schools, hospital, and downtown Oakland shopping. Public Water on site and

    Justin Liller Railey Realty, Inc.

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
  • lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
    /15

    $39,000

    • Land
    • 2.57 Acres
    • $15,175 per Acre

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

    2 lots (7 & 8) totaling 2.57 acres, on gently sloping wooded area. Nestled between Cannan Valley & Deep Creek Lake, this promises to be a perfect blend of convenience and tranquility. Nature surrounds you - the perfect spot for a cozy cabin! Call agent for more information!

    Julie Mead The KW Collective

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
  • 0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    /5

    $79,000

    • Land
    • 8.73 Acres
    • $9,049 per Acre

    0 Bethlehem Rd, Oakland, MD 21550

    LOT A= 8.73 acre parcel, located off Bethlehem Rd, in Western Maryland! Separate lot B (7.02 acres) behind this lot, also for sale. Near Potomac State Forest, this country setting, offers level land, perfect for building a home or if you are looking for a recreational outdoor property, this is a perfect spot for your adventures. Located outside the town of Oakland, just 8 mins away from schools,

    Thomas Long Railey Realty, Inc.

    0 Bethlehem 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

    $585,000

    • 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
  • 1 Lowes Dr, Oakland, MD 21550
    1 Lowes Dr, Oakland, MD 21550
    1 Lowes Dr, Oakland, MD 21550
    /15

    $175,000

    • Land
    • 1.6 Acres
    • $109,375 per Acre

    1 Lowes Dr, Oakland, MD 21550

    Lot #1. is 1.6 Acre Cleared Commercial Site in Lowe's Subdivision. Public Utilities and Natural gas to the site. Paved street access and High Traffic Zone. Plat available.

    Rich Orr Railey Realty, Inc.

    1 Lowes Dr, Oakland, MD 21550
  • 3395 Fingerboard Rd, Oakland, MD 21550
    3395 Fingerboard Rd, Oakland, MD 21550
    3395 Fingerboard Rd, Oakland, MD 21550
    /20

    $199,000 New Construction

    • 4 Beds
    • 2 Baths

    3395 Fingerboard Rd, Oakland, MD 21550

    6+ acre homestead with a 4BR, 2BA home currently under construction. Sellers plans have changed and they will not be finishing the house. The structure is under roof, mostly framed-in with building materials on site that will convey with the sale. A new well has been drilled and septic permit is approved for 4BRs. Located just outside of town limits, this parcel has impressive mountain views and

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    3395 Fingerboard Rd, Oakland, MD 21550
  • 519 Paradise Heights, Oakland, MD 21550
    519 Paradise Heights, Oakland, MD 21550
    519 Paradise Heights, Oakland, MD 21550
    /17

    $765,000

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    519 Paradise Heights, Oakland, MD 21550

    Secluded 4 bedroom 3 bath log home with lake access and single dock slip located in the heart of Deep Creek Lake Resort Area Full unfinished basement, front covered porch and rear deck. Call Office for particulares.

    Linda Deremer Appalachian Realty

    519 Paradise Heights, 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

    $440,000

    • 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 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    /3

    $45,900

    • Land
    • 1.02 Acres
    • $45,000 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy mountain views from this 1.02-acre, mostly wooded lot! No mobile homes permitted. No HOA. Easy access off Spring Glade Rd. Ideally situated between Oakland and Deep Creek Lake. Contact me today for more info!

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, Oakland, MD 21550
  • 267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    /30

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    267 San Francisco St, Oakland, MD 21550

    Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake views! So clear you’ll catch the slopes of Wisp in the distance. Includes 3 lots and the privacy is unmatched. This house was torn down to the foundation and a new house was built in 2009. Inside, you’ll find four spacious bedrooms, two and a half baths, and soaring vaulted ceilings and a grand fireplace.

    Bradley West HomeSmart

    267 San Francisco St, Oakland, MD 21550
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /50

    $379,000

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

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    961 Cedar Ln, Oakland, MD 21550
  • 0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • 62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    /30

    $249,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 2

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 88 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 $442,500, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$442,500
Median Single Family Sale Price
$431,000
Median Townhouse Sale Price
$510,000
Median 2 Bedroom Sale Price
$319,000
Median 1 Bedroom Sale Price
$239,900
Average Price Per Sq Ft
$265
Number of Homes for Sale
43
Last 12 months Home Sales
136
Months of Supply
3.80
Median List Price
$435,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 54 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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