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Oakland, MD Homes for Sale

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  • /19

    $65,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    This home needs TLC with the possibility to rebuild on existing foundation if you want to rehab. Buyer to confirm with the county and the town of Mt. Lake Park for rebuilding stipulations. Being sold "As Is". Caution: Entering this property is at your own discretion and responsibility.RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR

    Kathy Gibson Railey Realty, Inc.

    809 N St, Oakland, MD 21550
  • /11

    $23,000

    • Land
    • 0.12 Acre
    • $191,667 per Acre

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550

    Gallatin Woods is a unique log home community located on Lakeshore Drive in the innermost part of Deep Creek Lake. Each owner may build within the building cylinder indicated on the plat and have exclusive use of the parking area and the additional land that immediately surrounds the home site. All other land within the community is condominiumized to keep the area wooded and carefree. Owners

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
  • /50

    $679,900 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    4A Mystic Creek Trail, Oakland, MD 21550

    Discover refined mountain-lake living in this new construction townhome at Mystic Creek on Deep Creek Lake. Designed with today’s lifestyle in mind, the home features a modern open-concept main level ideal for entertaining, with clean lines, abundant natural light, and seamless flow between living, dining, and kitchen spaces. This spacious residence offers three primary suites, each with upscale

    Justin Liller Railey Realty, Inc.

    4A Mystic Creek Trail, 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

    Michael Fenton Railey Realty, Inc.

    47 Ridgewood Dr, 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
  • /2

    $349,000 Coming Soon

    • Land
    • 1.63 Acres
    • $214,110 per Acre

    189 Mountainview Ct, Oakland, MD 21550

    Coming soon! Secluded and spacious, this 1.7-acre lot in Mountainside boasts sweeping panoramic views from a hilltop perch above the lake, while still just minutes from Oakland’s dining and entertainment. The lot is picture-perfect for a personal retreat or vacation rental. The community offers public water and sewer, tennis courts, a lakeside clubhouse, and more.

    Kayla Mathew Coldwell Banker Premier

    189 Mountainview Ct, 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
  • /2

    $139,000

    • Land
    • 1 Acre
    • $139,000 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
  • /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
  • /37

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    1359 Cedar Ln, Oakland, MD 21550

    Thoughtfully remodeled and full of charm, this beautiful cabin offers 2 cozy bedrooms and 1.5 baths with an open-concept layout, laminated hardwood flooring throughout, an updated kitchen, and a spacious family room that instantly feels warm and welcoming. Whether you’re gathering inside or stepping out to enjoy the inviting hot tub, fire pit, and both a front and side deck, this home is made for

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    1359 Cedar Ln, 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
  • /2

    $4,000

    • Land
    • 0.46 Acre
    • $8,696 per Acre

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Jonathan Price Railey Realty, Inc.

    0 Rhododendron Unit MDGA2010748, 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
  • /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
  • /51

    $195,000

    • 1 Bed
    • 1 Bath
    • 460 Sq Ft

    565 Glendale Rd Unit 204B, Oakland, MD 21550

    Don’t miss this opportunity to own a beautifully updated 1-bedroom unit at Silver Tree Suites on Deep Creek Lake! This turn-key condo features recent flooring upgrades and is truly turn key, making it an ideal vacation retreat or income-producing rental. This particular unit offers a unique L-shaped layout, providing extra square footage and a more spacious feel compared to other efficiency

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 204B, 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
  • /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
  • /58

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    1021 E High St, Oakland, MD 21550

    Nestled in the convenient High Street neighborhood of Oakland, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this well-maintained 3 Bedroom 2 Bath residence boasts 1,520 sq. ft. above grade finished sq. ft. and a partially finished full basement awaiting your finishing touches. The exterior showcases a welcoming façade with a well-kept yard,

    Andrew Eiswert Railey Realty, Inc.

    1021 E High St, 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

    $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
  • /31

    $229,000

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft

    565 Glendale Rd Unit 312, Oakland, MD 21550

    Own your very own slice of peace and relaxation at Deep Creek Lake. The Suites at Silver Tree sits along 350 feet of private shoreline. The resort is a destination for many, and this unit (one of the top rental units in the building) produces an annual revenue of $25k+. One of only four loft units that has a private bedroom at the resort, this opportunity does not come up often. This is the

    Sara Wells O'Malley EXP Realty, LLC

    565 Glendale Rd Unit 312, Oakland, MD 21550
  • /29

    $369,000

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    531 Glendale Rd Unit B302, Oakland, MD 21550

    Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering

    Larry Smith Railey Realty, Inc.

    531 Glendale Rd Unit B302, Oakland, MD 21550
  • /68

    $1,199,990

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft

    444 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The View, this custom home offers stunning lake views in a serene, private setting. Centrally located less than 4 miles from Wisp while backing up to hundreds of acres of untouched forest, this property truly offers the best that Deep Creek Lake has to offer. This luxury home has been impeccably maintained as a

    Corbin Griffith Compass

    444 Woodlands Hill Ln, 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
  • /15

    $75,000

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft

    60 Gorman St, Oakland, MD 21550

    Bring you vision to this 3-bedroom, 1 bath home right outside of Oakland, Maryland. Features a spacious living room, updated kitchen and a cozy front deck. With a little love and final touches, the property could shine again - ideal for a renovation project or investment opportunity. There is a nice yard and off street parking. Great opportunity for buyers looking to invest or customize a home to

    Jennifer Jackson Charis Realty Group

    60 Gorman St, Oakland, MD 21550
  • /75

    $1,749,000

    • 4 Beds
    • 4.5 Baths
    • 2,605 Sq Ft

    1019 Lake Shore Dr, Oakland, MD 21550

    Tucked among the trees, Blue Spruce offers a perfect blend of modern comfort and serene natural beauty. This recently remodeled 4-bedroom, 4 and a half bathroom home invites you to relax, recharge, and reconnect with nature. With each bedroom offering an ensuite bathroom plus a half bath near the kitchen, this home was designed for comfort. Step inside to discover thoughtful updates throughout,

    Rachel Bruch Railey Realty, Inc.

    1019 Lake Shore Dr, 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
  • /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
  • /89

    $2,100,000

    • 6 Beds
    • 4.5 Baths
    • 3,882 Sq Ft

    209 Glendale Rd, Oakland, MD 21550

    If you're in the market for location, convenience, and rental income, this inviting 6 Bedroom 4.5 bath Lakefront home is calling for you! Located in the heart of the action on Deep Creek Lake, the 3 level chateau has been updated and upgraded both inside and out. Restaurants, the movie theatre, shopping and Deep Creek Lake State Park are all within walking distance. Offering an open layout with

    Bill Weissgerber Railey Realty, Inc.

    209 Glendale 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
  • /67

    $380,000

    • 4 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    723 Kings Ct, Oakland, MD 21550

    "Charming two-story home situated on a beautiful .292-acre level lot in a prime location (Kings Hills Estates) Enjoy the perfect blend of comfort and convenience with spacious living areas, a serene yard ideal for outdoor entertaining. Ideally located near a top-rate Hospital, popular shopping destinations, and just minutes to Broadford Lake. Whether you're enjoying a day on the water or running

    Debra Beitzel Long & Foster Real Estate, Inc.

    723 Kings Ct, Oakland, MD 21550
  • /22

    $95,000

    • Land
    • 2.86 Acres
    • $33,217 per Acre

    3501 George Washington Hwy, Oakland, MD 21550

    Welcome to 3501 George Washington Highway, a premier property containing 2.86 acres of prime land perfect for personal, or commercial storage purposes. The property features a recently renovated garage with four spacious bays, providing versatility for automotive, storage, or workshop purposes. The large gravel storage lot and concrete pad are ideal for all outdoor storage needs. Two metal

    Zach Wesolowski Railey Realty, Inc.

    3501 George Washington Hwy, Oakland, MD 21550
  • /42

    $175,000

    • Land
    • 21.46 Acres
    • $8,155 per Acre

    0 Sanders Ln Unit MDGA2009314, Oakland, MD 21550

    Tucked along scenic Sanders Lane just 4 miles from Oakland, MD, this picturesque 21.46-acre pastoral lot offers the perfect blend of open space, gentle rolling fields, and peaceful countryside charm. Surrounded by open spaces, in a sought-after neighborhood, this property is ideal for building your dream estate, hobby farm, or private retreat. Enjoy wide-open skies, room to roam, and the serenity

    Susan Bell Railey Realty, Inc.

    0 Sanders Ln Unit MDGA2009314, 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
  • /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
  • /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
  • /102

    $2,350,000

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built log home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. This home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled comfort. Nestled on 1.03

    Shelia McCracken Taylor Made Deep Creek Vacations & Sales

    2725 Stockslager Rd, Oakland, MD 21550
  • /33

    $919,000

    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft

    39 Leo Friend Rd, Oakland, MD 21550

    **In the process of having new pictures taken. To see the pictures on the prior listing, go to MSL listing

    Andrew Orr The KW Collective

    39 Leo Friend Rd, Oakland, MD 21550
  • /5

    $27,500

    • Land
    • 0 Acre

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550

    Building lot located in the premier subdivision - Gallatin Woods! This beautifully wooded community is located in the heart of the Deep Creek Lake. This is a condominium ownership type in regards to the land itself, but is buildable for a single family home! There are 8 pre-approved building plans designed and engineered by Mountaineer Log Homes that range anywhere from 1571 to 3908 square feet.

    Nina Beitzel Railey Realty, Inc.

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550
  • /25

    $269,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 4

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