173

Homes for Sale in 21550

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  • /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
  • /110

    $1,900,000

    • 5 Beds
    • 3.5 Baths
    • 4,619 Sq Ft

    815 Chadderton School Rd, Oakland, MD 21550

    Experience lakefront living at its finest in this exceptional 5-bedroom, 3.5-bath home offering over 4,600 square feet of living space on a private lot of more than one acre. Featuring an incredibly spacious primary suite on the main level, as well as an additional master suite on the second level, this home is ideal for both full-time living and hosting guests. Enjoy breathtaking lake views from

    Kevin Liller Railey Realty, Inc.

    815 Chadderton School 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
  • /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
  • /33

    $875,000

    • 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
  • /104

    $1,350,000

    • 5 Beds
    • 5.5 Baths
    • 3,696 Sq Ft

    615 Sandy Shores Rd, Mc Henry, MD 21541

    This stunning log home near Wisp Resort offers a luxurious retreat with seasonal views, an indoor pool house and plenty of space for indoor and outdoor living. Five-bedroom, five-and-a-half-bath masterpiece is designed for both relaxation and entertainment. Step inside to discover an open floor plan adorned with exposed beams and rich wood floors. The gourmet kitchen, equipped with high-end

    Kellyann Green Railey Realty, Inc.

    615 Sandy Shores Rd, Mc Henry, MD 21541
  • /37

    $629,000

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    231 Santa fe Trail, Oakland, MD 21550

    3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. NO HOA! Conveys fully furnished. Features include central AC, exposed beams, updated flooring, gas fireplace on main level, lower level rec room with pool table and

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    231 Santa fe Trail, Oakland, MD 21550
  • /43

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 1,492 Sq Ft

    333 Sloan Tract Rd, Oakland, MD 21550

    Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home has three levels of living space, hardwood flooring and a nice fireplace. The lower level is totally finished with walk-out access. There are multiple covered porches plus a hot tub that are great outdoor spaces to enjoy year round. This home feels very secluded but is just minutes to Deep Creek Lake and Wisp

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    333 Sloan Tract Rd, Oakland, MD 21550
  • /52

    $749,900

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community with an available home warranty. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    25 Silver Tree Ln, Oakland, MD 21550
  • /2

    $555,000 Coming Soon

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

    24 Trailside Way Unit 17, Oakland, MD 21550

    Coming soon!

    Jackie Ball Daley Northrop Realty

    24 Trailside Way Unit 17, Oakland, MD 21550
  • /11

    $199,900

    • Land
    • 0.11 Acre
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • /103

    $2,399,000 Pre-Foreclosure

    • 7 Beds
    • 5 Baths
    • 4,691 Sq Ft

    41 Boyd Paugh Ln, Oakland, MD 21550

    Gorgeous 7 bedroom home with dock slip! This newer construction home sits on a quiet corner of Deep Creek Lake with 200 feet of lake frontage. Located in the beautiful and quiet Heron Cove community and comes with two community lake access points, one with a sandy beach area, tennis courts, and walking trails. The level lot is surrounded by trees and designed for privacy and outdoor enjoyment,

    Rachel Bruch Railey Realty, Inc.

    41 Boyd Paugh Ln, 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
  • /10

    $995,000

    • Land
    • 0.58 Acre
    • $1,715,517 per Acre

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550

    RARE OPPURTUNITY! Discover one of the final opportunities to own true lakefront on the iconic Glendale Road! This premier homesite offers approximately 75 feet of pristine Deep Creek Lake frontage in a serene no wake zone, perfect for swimming, kayaking, and peaceful lakeside enjoyment. Zoning in this area is Town Center. This allows for a larger building area within the lot with relaxed

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
  • /8

    $69,000

    • Land
    • 0.66 Acre
    • $104,545 per Acre

    LOT 7 Grand Estates Dr, Sang Run, MD 21541

    Looking for the perfect spot to build your Deep Creek Lake getaway? This prime mountaintop lot in Lago Vista is ready for your dream home. With public utilities available, you can start planning your mountain retreat, full-time residence, or investment property with ease. Enjoy having Wisp Resort and Lodestone Golf Club practically in your backyard, plus all the fun and adventure of Deep Creek

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    LOT 7 Grand Estates Dr, Sang Run, MD 21541
  • /13

    $119,900

    • Land
    • 0.78 Acre
    • $153,718 per Acre

    120 Sundance Way, McHenry, MD 21541

    Level wooded building lot with scenic mountain views! This .78-acre homesite is centrally located minutes from Wisp Resort, Deep Creek Lake, Lodestone Golf Course, local restaurants, and nearby state parks, all while tucked away in a private mountaintop community. Ready to build with public water and sewer hookups to site. A straightforward opportunity to build your mountain dream home right in

    Mike Fenton Railey Realty, Inc.

    120 Sundance Way, McHenry, MD 21541
  • /27

    $229,900

    • 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
  • /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
  • /29

    $75,000

    • Land
    • 0.6 Acre
    • $125,000 per Acre

    40 Fern Loop, Sang Run, MD 21541

    Escape to the mountains and relax on your own piece of paradise on "Fern Loop". Build your dream home on this beautiful wooded homesite-"Lot 40" in the peaceful community of Sandy Shores Heights. On the mountaintop with easy access to the Lodestone Golf Course and a convenient hop to Deep Creek Lake, Fork Run, Yough River & Wisp Ski Resort. Utilities to site with public water & sewer hookups

    Kathy Gibson Railey Realty, Inc.

    40 Fern Loop, Sang Run, MD 21541
  • /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

    Mike Fenton Railey Realty, Inc.

    47 Ridgewood Dr, Oakland, MD 21550
  • /10

    $99,000

    • Land
    • 9 Acres
    • $11,000 per Acre

    ±9 Acres Cranesville Rd, Mount Lake Park, MD 21550

    Escape to the quiet beauty of Western Maryland with this ±9-acre parcel offering level pastureland and wide-open views of the Cranesville countryside. Whether you’re dreaming of a peaceful mountain getaway or a full-time residence surrounded by nature, this property delivers the perfect setting. The land is open and usable—ideal for gardens, farming, or simply enjoying the space and privacy. You

    Brent Housley Railey Realty, Inc.

    ±9 Acres Cranesville Rd, Mount Lake Park, MD 21550
  • /32

    $199,999

    • 4 Beds
    • 2 Baths
    • 1,760 Sq Ft

    413 D St, Oakland, MD 21550

    Reduced price for immediate sale! 4BR, 2BA renovated home in Mountain Lake Park feels like NEW! Stripped down to the studs for a professional makeover. Stylish kitchen with stainless steel appliances and butcher block countertop, vinyl planking floors, efficient mini-split ceiling unit, modern fixtures and lighting, custom tile shower and reimagined bathroom space. Finished basement. Fenced

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    413 D St, 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
  • /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

    $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
  • /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
  • /8

    $79,900

    • Land
    • 3.67 Acres
    • $21,771 per Acre

    Lot 2 Pergin Farm Rd, Oakland, MD 21550

    3.67± Acre Perc-Approved Wooded Lot – Prime Location Near Deep Creek Lake Discover the perfect setting for your dream home on this 3.67± acre perc-approved wooded lot located just off Pergin Farm Road. Offering privacy and natural surroundings, this beautiful property is ideal for a second home getaway or full-time residence. Conveniently situated just minutes from Deep Creek Lake, and only 10

    Rich Orr Railey Realty, Inc.

    Lot 2 Pergin Farm Rd, Oakland, MD 21550
  • /6

    $4,000

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

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Here is an affordable chance to own a lot and have access to all of Youghiogheny Mountain Resort's beautiful and fun amenities!

    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
  • /26

    $475,000

    • Land
    • 1.34 Acres
    • $354,478 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

    Nina Beitzel Railey Realty, Inc.

    LOT 25 Holy Cross Dr, Oakland, MD 21550
  • /17

    $349,000

    • Land
    • 0.34 Acre
    • $1,026,471 per Acre

    LOT 12 Boulder Ridge Dr, McHenry, MD 21541

    BOULDER RIDGE #12: A premier lot in this gated community sits atop Wisp Resort. This location provides incredible lake and mountain views and is just minutes away from Deep Creek Lake, acres of state parks, world-class whitewater rafting, and a variety of golf venues for all levels of the sport! With easy access to the Eyeopener and Main Street slopes, you can hop on the trails to enjoy the first

    Kathy Gibson Railey Realty, Inc.

    LOT 12 Boulder Ridge Dr, McHenry, MD 21541
  • /32

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft

    6485 Oakland Sang Run Rd, Oakland, MD 21550

    If you are looking for an updated one-level living home with a newer roof, new hot water heater, some new windows, and new flooring, this is a great option. Offering three bedrooms and an unfinished basement with endless possibilities for additional living space, plus a 1-car integrated garage. There are washer/dryer hookups on both the main and lower levels for added convenience. The exterior

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    6485 Oakland Sang Run Rd, Oakland, MD 21550
  • /61

    $185,000

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    729 E Oak St, Oakland, MD 21550

    Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front

    Kevin Liller Railey Realty, Inc.

    729 E Oak St, 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
  • /24

    $225,000

    • Land
    • 1.33 Acres
    • $169,173 per Acre

    Lot 94 Wisp Adventure Rd, McHenry, MD 21541

    Oversized mountain-view lot in North Camp Ridge, ideally located just minutes from Wisp Resort amenities. This centrally located parcel offers the perfect setting to build your custom vacation home or mountain retreat. Enjoy expansive, unobstructed mountain views and the privacy that comes with a generously sized lot, while still being close to skiing, golf, hiking, lake activities, dining, and

    Larry Smith Railey Realty, Inc.

    Lot 94 Wisp Adventure Rd, McHenry, MD 21541
  • /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
  • /11

    $22,500

    • Land
    • 0.59 Acre
    • $38,136 per Acre

    0 C St, Mountain Lake Park, MD 21550

    .59 acre building lot in Mt Lake Park on C St. Public sewer and water available, electric on site. Partially cleared but mostly wooded setting and backs to small stream.

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 C St, Mountain Lake Park, MD 21550
  • /2

    $69,900 Coming Soon

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    74 Parks Rd, Oakland, MD 21550

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

    Emillie Albrecht Real Broker, LLC

    74 Parks Rd, Oakland, MD 21550

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