165

Oakland, MD Homes for Sale

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  • 135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    /36

    $325,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550

    Wonderful lake view condo right in the heart of Deep Creek Lake! It is truly hard to beat this location as you are so close to many of the areas favorite restaurants, bars, shopping and more! Less than 5 miles to Wisp Resort as well! Enjoy being able to take advanatage of everything Deep Creek Lake and Mountain Maryland has to offer in this excellently maintained condo that is ready for you!

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    135 Jeffrey Ln Unit 19D, 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

    $818,000

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

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Instant opportunity for $50k equity! Appraised on 08/11/2025 for $868,000 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. This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 939 Glendale Rd Unit 19, Oakland, MD 21550
    939 Glendale Rd Unit 19, Oakland, MD 21550
    939 Glendale Rd Unit 19, Oakland, MD 21550
    /27

    $785,000

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft

    939 Glendale Rd Unit 19, Oakland, MD 21550

    SEE DOCUMENTS FOR 07/2025 TAX STATEMENT--$1,533 annual assessment for HOA reserves. $1,500 Annual fee to Bill's Marine for assumable boat-strip lease. $4,500 Annual condo fees. Condo Association responsible for roof, building exterior maintenance, lawn maintenance, snow removal, replacement of deck, porch and front door. Water is included in the condo fees. Sewer fees are not included and

    Rick Davis Richard A. Davis & Associates

    939 Glendale Rd Unit 19, Oakland, MD 21550
  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /50

    $529,900

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

    126 Leo Friend Rd, Oakland, MD 21550

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

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • 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
  • 175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    /55

    $555,000

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Amazing and rare opportunity in Trader's Landing! These wonderful stand alone homes in this community do not come up for sale very often. Offering 4 bedrooms, 4 and a half baths, and over 3,100 finished square feet on 4 levels of living space, this is one of the largest homes in the development! Enjoy relaxing with some nice views on the spacious deck or go for a soak in the hot tub on the

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • 20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    /39

    $485,000

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

    Lakefront Luxury at Will O’ The Wisp – Nicely renovated Unit 308/408 offers a 2 BR, 2 Bath 2- level floor plan perfect for guests or steady rental income. Enjoy breathtaking Deep Creek Lake views from every bedroom and the main living space. Resort-Style Amenities Include:Indoor Pool with Waterfall Hot Tub, Cedar-Lined Sauna, Fitness Room & Game Room, Sandy Lakefront Beach with Community

    Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, 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

    $599,000

    • 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

    Jessie Railey Railey Realty, Inc.

    6652 George Washington Hwy, Oakland, MD 21550
  • 20 Maple Del Ln, Oakland, MD 21550
    20 Maple Del Ln, Oakland, MD 21550
    20 Maple Del Ln, Oakland, MD 21550
    /17

    $549,000 New Construction

    • 2 Beds
    • 1 Bath

    20 Maple Del Ln, Oakland, MD 21550

    *To be built A frame* Looking for a newly built home on a wooded lot close to everything Deep Creek Lake offers. This home can be delivered complete in a 4 month time span. Call today for details

    Michael Cumerlato Jason Mitchell Group

    20 Maple Del Ln, Oakland, MD 21550
  • 620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    /21

    $555,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,850 Sq Ft

    620 Crosby Dr, Oakland, MD 21550

    BRAND NEW CONSTRUCTION! 4BR/3.5BA home with attached 2 car garage in Country Club Acres! Perched at the very top of the mountain overlooking Oakland golf course, 2,850 sf and 2.84 acres of land (lots 73-79 combined). Modern design offering plenty of natural light, open living and elite finishes. Features include Andersen windows & sliders, multiple ensuites, custom tile bathrooms, fireplace,

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    620 Crosby Dr, Oakland, MD 21550
  • 0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    /9

    $49,900

    • Land
    • 1.00 Acre
    • $49,900 per Acre

    0 Longview Ln, Oakland, MD 21550

    1.00 Acre wooded lot loacted in George Brunson Subdivision. Close to Deep Creek Lake, Wisp Ski Resort and Oakland. Approved perc

    Linda Deremer Appalachian Realty

    0 Longview Ln, Oakland, MD 21550
  • 0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    /4

    $14,000

    • Land
    • 0.25 Acre
    • $56,000 per Acre

    0 E Reese St, Oakland, MD 21550

    Lot in town. Easy access to main roads and the Town of Oakland. Quiet St. Paved.

    Thomas Long Railey Realty, Inc.

    0 E Reese St, Oakland, MD 21550
  • 0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    /5

    $30,000

    • Land
    • 0.34 Acre
    • $88,235 per Acre

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550

    Love Deep Creek Lake living. This 0.34 acre wooded lot sits near the heart of everything that makes the lake special. Launch the boat at nearby marinas, hike and swim at Deep Creek Lake State Park, and enjoy four season adventure at Wisp Resort with skiing, tubing, and mountain rides. Restaurants, shops, and local events are just down the road, while your homesite feels peaceful and private. Do

    Debra Hayne Cummings & Co. Realtors

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
  • 197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    /111

    $2,600,000

    • 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 with 200' of prime frontage at the end of private lane. The impressive cottage style residence offers an inviting open main level living area with a fabulous kitchen,

    Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, Oakland, MD 21550
  • 929 Dogwood Dr, Oakland, MD 21550
    929 Dogwood Dr, Oakland, MD 21550
    929 Dogwood Dr, Oakland, MD 21550
    /30

    $220,000

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

    929 Dogwood Dr, Oakland, MD 21550

    Nestled in the heart of Yough Mountain Resort, this well-maintained 3-bedroom, 1-bath rancher offers an open floor plan with a cozy gas fireplace, stainless steel appliances, and walk-in closets. The home features a circular gravel driveway, a rear deck, and a level backyard that borders Yough Mountain common grounds, providing plenty of outdoor space for relaxation and entertainment. Perfect as

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    929 Dogwood Dr, Oakland, MD 21550
  • 2311 Boy Scout Rd, Oakland, MD 21550
    2311 Boy Scout Rd, Oakland, MD 21550
    2311 Boy Scout Rd, Oakland, MD 21550
    /68

    $1,699,900

    • 4 Beds
    • 3 Baths
    • 3,517 Sq Ft

    2311 Boy Scout Rd, Oakland, MD 21550

    Charming Lake Front Craftsman at Deep Creek Lake - Private, wooded, and nearly an acre, this waterfront property delivers rare seclusion with a clean, gentle slope into deep water. Private Type-A dock with over 100’ of lakefront. Located just off Boyscout Rd, this home is positioned forward on the lot to maximize open-water views while maintaining a natural tree line for cover. A full-length deck

    Jon Bell Railey Realty, Inc.

    2311 Boy Scout Rd, Oakland, MD 21550
  • 9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    /20

    $28,000

    • Land
    • 0.96 Acre
    • $29,167 per Acre

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    Don’t miss this rare opportunity to own a .96-acre double lot with perc approval for a 3-bedroom sand mound septic system—and a driveway already installed, making it even easier to bring your dream home or getaway cabin to life. Nestled within the quiet, wooded community of Yough Mountain Resort, this property offers the perfect blend of peace, privacy, and outdoor adventure. Enjoy access to over

    Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
  • 1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    /24

    $100,000

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft

    1101 Wheeling Ave, Oakland, MD 21550

    Investor Opportunity – 1101 Wheeling Ave, Oakland, MD 21550 – $190,000Attention Investors and Visionaries!Unlock the potential in this unique property located in the heart of Oakland, Maryland. Priced to move at $190,000, this hidden gem offers a perfect canvas for your next flip, rental, or renovated. Features 3 bedrooms 2 baths, 2 car garage, wrap around porch, jacuzzi and a pool!

    Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
  • 88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    88 Knoll Crest Heights Dr, Oakland, MD 21550
    /38

    $219,000

    • 3 Beds
    • 2.5 Baths
    • 1,867 Sq Ft

    88 Knoll Crest Heights Dr, Oakland, MD 21550

    Discover the perfect blend of convenience and country charm in this 3-bedroom, 2.5-bath home (one bath unfinished) set on a spacious lot with incredible mountain and valley views. Enjoy the peaceful atmosphere of a rural setting while being just minutes from downtown Oakland’s shopping, dining, schools, and Garrett Regional Medical Center.Inside, you’ll find a comfortable and functional

    Justin Liller Railey Realty, Inc.

    88 Knoll Crest Heights Dr, Oakland, MD 21550
  • 1256 Boiling Spring Rd, Oakland, MD 21550
    1256 Boiling Spring Rd, Oakland, MD 21550
    1256 Boiling Spring Rd, Oakland, MD 21550
    /18

    $250,000

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

    1256 Boiling Spring Rd, Oakland, MD 21550

    About 1256 Boiling Spring Rd, Oakland, MD1256 Boiling Spring Road is a raised-ranch, single-family home built in 1999. It features 3 bedrooms, 2 baths, and approximately 1,456 sq ft on a spacious 1.72-acre lot . It’s situated just outside the town of Oakland, near Deer Park—a location that offers privacy while remaining close to local attractions and community amenities Fun &

    Tanavia Greer Long & Foster Real Estate, Inc.

    1256 Boiling Spring Rd, Oakland, MD 21550
  • Lot 27 Stool Rock Rd, Oakland, MD 21550
    Lot 27 Stool Rock Rd, Oakland, MD 21550
    Lot 27 Stool Rock Rd, Oakland, MD 21550
    /4

    $3,500

    • Land
    • 0.51 Acre
    • $6,863 per Acre

    Lot 27 Stool Rock Rd, Oakland, MD 21550

    Nestled in the scenic mountains of Western Maryland, this unbuildable lot offers the perfect gateway to the peaceful surroundings, beautiful views, and abundant wildlife of the Youghiogheny Mountain Resort. This membership lot provides exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side riding, fishing at Muddy Creek, and outdoor recreation. Community

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    Lot 27 Stool Rock Rd, Oakland, MD 21550
  • 104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    /13

    $425,000

    • 4 Beds
    • 4.5 Baths
    • 1,596 Sq Ft

    104 Pine Top Trail, Oakland, MD 21550

    Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

    laura Flynn 1 Real Estate Source LLC

    104 Pine Top Trail, Oakland, MD 21550
  • 503 E Alder St, Oakland, MD 21550
    503 E Alder St, Oakland, MD 21550
    503 E Alder St, Oakland, MD 21550
    /8

    $279,991

    • 4 Beds
    • 2 Baths
    • 2,496 Sq Ft

    503 E Alder St, Oakland, MD 21550

    Investor’s Dream or Value-Seeker’s Opportunity | Queen Anne Victorian with Timeless Charm & Huge PotentialThis is the opportunity you’ve been waiting for—a true investor’s dream or the perfect chance for someone looking to buy a home at a low price and create exceptional value. This spacious and elegant Queen Anne Victorian combines historic beauty with incredible potential. The current

    Jameel Scott Coldwell Banker Realty

    503 E Alder St, 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

    $599,000

    • Land
    • 1.34 Acres
    • $447,015 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
  • 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
  • 565 Glendale Rd Unit 116, Oakland, MD 21550
    565 Glendale Rd Unit 116, Oakland, MD 21550
    565 Glendale Rd Unit 116, Oakland, MD 21550
    /29

    $179,000

    • 1 Bed
    • 1 Bath
    • 484 Sq Ft

    565 Glendale Rd Unit 116, Oakland, MD 21550

    Don't miss this rare opportunity to own a beautifully updated 1-bedroom unit at Silver Tree Suites on Deep Creek Lake! This turn-key condo features recent upgrades and is being sold fully furnished, making it perfect as a vacation getaway or income-generating rental. The unit boasts a solid rental history, offering immediate investment potential. Enjoy access to a wide range of on-site amenities,

    Nina Beitzel Railey Realty, Inc.

    565 Glendale Rd Unit 116, Oakland, MD 21550
  • 5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    5202 Hutton Rd, Oakland, MD 21550
    /38

    $239,000

    • 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
  • 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
  • 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
  • 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
  • 1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    /75

    $1,755,000

    • 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
  • 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
  • 60 Gorman St, Oakland, MD 21550
    60 Gorman St, Oakland, MD 21550
    60 Gorman St, Oakland, MD 21550
    /7

    $110,000

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

    60 Gorman St, Oakland, MD 21550

    Attention investors and savvy buyers! This 2-bedroom, 1-bathroom home in the heart of Oakland, Maryland is a prime opportunity for your next project. Whether you’re looking to fix and flip for profit or renovate and hold as a cash-flowing rental, this property is packed with potential. Located on a quiet street close to local shops, dining, and recreation, it offers a solid foundation and a

    ryan byrd Coldwell Banker Realty

    60 Gorman St, Oakland, MD 21550
  • 565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    /27

    $269,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

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

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550
  • 873 Paradise Heights, Oakland, MD 21550
    873 Paradise Heights, Oakland, MD 21550
    873 Paradise Heights, Oakland, MD 21550
    /72

    $829,000

    • 5 Beds
    • 4 Baths
    • 2,934 Sq Ft

    873 Paradise Heights, Oakland, MD 21550

    Escape to Sage Mountain Retreat, a beautifully crafted 5-bedroom, 4-bath custom home nestled in a private wooded setting—just minutes from Deep Creek Lake State Park and walking distance to popular lakefront restaurants and Silvertree Marina. This fully furnished retreat features: Modern kitchen with granite countertops, Two spacious living areas for relaxing or entertaining, Primary Bedroom

    Rich Orr Railey Realty, Inc.

    873 Paradise Heights, 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
    /28

    $179,000

    • 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

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