220

Homes for Sale in 21550

Section Image
  • 98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    /30

    $550,000

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

    98 Bear Run Rd, Oakland, MD 21550

    Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 acres for a total of 42.19 acres. The 2-acre parcel is improved by a fully furnished (26’X42’), 3-bedroom, 2-bathroom Ranch style dwelling and a large parking area. The interior offers a spacious living room, and an eat-in kitchen with all appliances, furniture and window AC units. The land is un-zoned

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    98 Bear Run Rd, Oakland, MD 21550
  • 3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    /55

    $400,000

    $120K PRICE INCREASE
    • Land
    • 43.72 Acres
    • $9,149 per Acre

    3257 George Washington Hwy, Oakland, MD 21550

    Discover approximately 43.72 acres of beautiful mostly wooded land offering privacy, mountain views, and exceptional convenience. This expansive property provides easy access to both George Washington Highway and Garrett Highway, making travel simple while still feeling tucked away in nature. Set up with a well and septic system, this property is perfect to build your dream home with an already

    Justin Liller Railey Realty, Inc.

    3257 George Washington Hwy, Oakland, MD 21550
  • 2 Fern Loop, Sang Run, MD 21541
    2 Fern Loop, Sang Run, MD 21541
    2 Fern Loop, Sang Run, MD 21541
    /15

    $64,900

    $14K PRICE DROP
    • Land
    • 30,927 Sq Ft
    • $91,408 per Acre

    2 Fern Loop, Sang Run, MD 21541

    A clean .71-acre building lot in Sandy Shores Heights—level, partially wooded, with utilities to site. Minutes from Lodestone, Wisp, and Deep Creek Lake... this property sits in a quiet golf side loop with mountain views and paved access. Water and sewer taps included. Road maintenance and snow removal covered by HOA fees. Call today for details!

    Mike Fenton Railey Realty, Inc.

    2 Fern Loop, Sang Run, MD 21541
  • 0 Mayhew Inn Rd Unit MDGA2012550, Oakland, MD 21550
    0 Mayhew Inn Rd Unit MDGA2012550, Oakland, MD 21550
    0 Mayhew Inn Rd Unit MDGA2012550, Oakland, MD 21550
    /7

    $169,900

    • Land
    • 42,253 Sq Ft
    • $175,155 per Acre

    0 Mayhew Inn Rd Unit MDGA2012550, Oakland, MD 21550

    Picture this: your own slice of the woods at Deep Creek Lake, with a path straight to the water. This 0.97 acre raw land parcel (Tax ID 1218071878) borders Maryland's lakefront buffer strip and puts you in one of the most desirable settings in the area, part of the Millhouse Manor subdivision, with a community lake access area at the end of Red Run Cove. This no wake cove is made for lazy days of

    Jeremy Cunningham Railey Realty, Inc.

    0 Mayhew Inn Rd Unit MDGA2012550, Oakland, MD 21550
  • 0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550
    0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550
    0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550
    /21

    $599,900

    • Land
    • 18.87 Acres
    • $31,791 per Acre

    0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550

    An exceptional opportunity to own 18.87 acres in one of Deep Creek Lake's most desirable locations. Featuring 8 approved perc sites, this lake access property offers outstanding potential for a private estate, luxury mountain retreat, or future subdivision with the possibility of up to 8 homesites. Ideally situated on Boy Scout Road, the property provides the perfect balance of privacy and

    Jon Bell Railey Realty, Inc.

    0 Boy Scout Rd Unit MDGA2012474, Oakland, MD 21550
  • 758 Wisp Mountain Rd Unit 9A, Mc Henry, MD 21541
    758 Wisp Mountain Rd Unit 9A, Mc Henry, MD 21541
    758 Wisp Mountain Rd Unit 9A, Mc Henry, MD 21541
    /66

    $184,000

    $39K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,086 Sq Ft

    758 Wisp Mountain Rd Unit 9A, Mc Henry, MD 21541

    If you are interested in easy living while still enjoying a houseful of company, this could be the place for you. Five owners share in ownership of this villa (not a time share). Each owner gets about 10 weeks per year via a rotation list established twice a year. Owners also have a large, locked closet within the garage to hold miscellaneous personal items, food, sports equipment, clothes, etc.

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    758 Wisp Mountain Rd Unit 9A, Mc Henry, MD 21541
  • 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
  • 400 Bear Dr E, Oakland, MD 21550
    400 Bear Dr E, Oakland, MD 21550
    400 Bear Dr E, Oakland, MD 21550
    /42

    $249,900

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 560 Sq Ft

    400 Bear Dr E, Oakland, MD 21550

    Tucked away in the scenic beauty of Yough Mountain Resort, this exceptional 2-bedroom, 2-bath log cabin offers the perfect blend of rustic charm and modern comfort. Spanning two stories, this immaculately maintained home has seen thoughtful renovations in recent years, creating a warm and inviting retreat that’s move-in ready.Step inside to discover cozy living spaces ideal for relaxing

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    400 Bear Dr E, Oakland, MD 21550
  • Lot 18 Buck Dr, Oakland, MD 21550
    Lot 18 Buck Dr, Oakland, MD 21550
    Lot 18 Buck Dr, Oakland, MD 21550
    /6

    $19,900

    • Land
    • 1.35 Acres
    • $14,741 per Acre

    Lot 18 Buck Dr, Oakland, MD 21550

    This 1.352 acre lot borders Buck Drive and also Antelope Drive. It is best to access the lot using the directions provided via Antelope Drive as it is a much better road. Buck Drive is very difficult to traverse and access through Antelope Drive is recommended. Pictures of the lot are taken from Antelope Drive. Perc approved for a three bedroom home with a sand mound system. Wooded lot just

    Kevin Liller Railey Realty, Inc.

    Lot 18 Buck Dr, Oakland, MD 21550
  • 181 Glotfelty Dr, Oakland, MD 21550
    181 Glotfelty Dr, Oakland, MD 21550
    181 Glotfelty Dr, Oakland, MD 21550
    /51

    $399,000

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

    181 Glotfelty Dr, Oakland, MD 21550

    Talk about central location! Only minutes to Deep Creek Lake, Wisp Resort and downtown Oakland! This 3 bedroom, 2 bath home sits on a nice-sized 1.29 AC partially wooded lot, at the end of a private, no thru street. Great outdoor living space as well with a covered porch, back deck and large 24x44 detached garage. Many upgrades & improvements by the current owner, to include new HVAC, all new

    Kathy Gibson Railey Realty, Inc.

    181 Glotfelty Dr, Oakland, MD 21550
  • 826 G Swauger Rd, Oakland, MD 21550
    826 G Swauger Rd, Oakland, MD 21550
    826 G Swauger Rd, Oakland, MD 21550
    /33

    $1,095,000

    $105K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,914 Sq Ft

    826 G Swauger Rd, Oakland, MD 21550

    A Rare Fine Indeed! The private, end of the road farm is located in the much-desired Pleasant Valley area of southern Garrett County, MD.Built in 1933 and remodeled in 2020, this farmhouse is a must see. The inviting living area is complemented by a wood burning stove, while a LP gas furnace provides hot water radiant heat throughout the home. The kitchen features concrete countertops and is

    Larry Roth Railey Realty, Inc.

    826 G Swauger Rd, Oakland, MD 21550
  • 23 Snowshoe Ct, McHenry, MD 21541
    23 Snowshoe Ct, McHenry, MD 21541
    23 Snowshoe Ct, McHenry, MD 21541
    /12

    $249,000

    • Land
    • 16,117 Sq Ft
    • $672,973 per Acre

    23 Snowshoe Ct, McHenry, MD 21541

    True ski-in/out slope front building lot at Wisp ski resort with expansive lake and scenic mountain views too! Located at the top of the Main Street slope, this building site is one of the rare slope front building sites with direct access to the ski trail and chair lift that also has views of Deep Creek Lake! Take advantage of the entire winter ski season as Wisp has historically opened this

    Mike Kennedy Railey Realty, Inc.

    23 Snowshoe Ct, McHenry, MD 21541
  • Lot 115 Biltmore View, McHenry, MD 21541
    Lot 115 Biltmore View, McHenry, MD 21541
    Lot 115 Biltmore View, McHenry, MD 21541
    /11

    $125,000

    • Land
    • 30,492 Sq Ft
    • $178,571 per Acre

    Lot 115 Biltmore View, McHenry, MD 21541

    Premium golf-front building lot located in a private, gated community and ideally situated near all Deep Creek Lake amenities, including Wisp Ski Resort, the ASCI Whitewater Course, and Fork Run Trails. This .7-acre level, wooded parcel offers potential views of the golf course and surrounding mountain landscape—an exceptional setting to build your dream home in the heart of Deep Creek Lake.

    Kellyann Green Railey Realty, Inc.

    Lot 115 Biltmore View, McHenry, MD 21541
  • 5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    /68

    $460,000

    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft

    5154 Maryland Hwy, Oakland, MD 21550

    Escape to the tranquility of country living in this spacious 5-bedroom, 2-bath home nestled on over 2 acres and conveniently located just minutes from the recreational opportunities of Deep Creek Lake and the charming town of Oakland, The property offers the perfect combination of peaceful country living and easy access to shopping, dining, and year-round activities. The kitchen has been

    Charlene Deremer Aburn Coldwell Banker Home Town Realty

    5154 Maryland Hwy, Oakland, MD 21550
  • LOT 33 Winding Estates Dr, Mc Henry, MD 21550
    LOT 33 Winding Estates Dr, Mc Henry, MD 21550
    LOT 33 Winding Estates Dr, Mc Henry, MD 21550
    /9

    $120,000

    $5K PRICE DROP
    • Land
    • 1.2 Acres
    • $100,000 per Acre

    LOT 33 Winding Estates Dr, Mc Henry, MD 21550

    Located on Wisp Mountain in the sought-after Lago Vista community, this 1.20-acre lot offers exceptional privacy and a beautiful natural setting. The frontage is wide along the road and expands further toward the back, creating a generous building area surrounded by trees. Seasonal views of Deep Creek Lake can be enjoyed when the leaves are down, and the preserved common area across the street

    Kelsey Meyers Railey Realty, Inc.

    LOT 33 Winding Estates Dr, Mc Henry, MD 21550
  • 8946 Oakland Sang Run Rd, Oakland, MD 21550
    8946 Oakland Sang Run Rd, Oakland, MD 21550
    /2

    $309,000

    $60K PRICE DROP
    • Land
    • 20,473 Sq Ft
    • $657,447 per Acre

    8946 Oakland Sang Run Rd, Oakland, MD 21550

    There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082 All parcels together are 8 acres WARNING: The house on this property is condemned and ready for tear down. Enter at your own risk.

    Joe Zorzit Eagle Commercial Realty

    8946 Oakland Sang Run Rd, Oakland, MD 21550
  • 325 Markwood Dr, Oakland, MD 21550
    325 Markwood Dr, Oakland, MD 21550
    325 Markwood Dr, Oakland, MD 21550
    /65

    $799,000

    • 4 Beds
    • 3.5 Baths
    • 3,376 Sq Ft

    325 Markwood Dr, Oakland, MD 21550

    LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    325 Markwood Dr, Oakland, MD 21550
  • 3 Nature Run, Mc Henry, MD 21541
    3 Nature Run, Mc Henry, MD 21541
    3 Nature Run, Mc Henry, MD 21541
    /32

    $659,900

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 2,877 Sq Ft

    3 Nature Run, Mc Henry, MD 21541

    Brand New Log Style Chalet at Deep Creek Lake! Scheduled for completion in 2026, this 5 Bed, 3.5 Bath mountain retreat pairs refined design with a focus on efficiency and long-term performance. The open-concept layout is defined by soaring vaulted ceilings, expansive windows, and curated natural wood finishes that bring warmth and scale to the space. The stylish fireplace anchors the main living

    Jon Bell Railey Realty, Inc.

    3 Nature Run, Mc Henry, MD 21541
  • 58 Bright Passage Rd Unit 6B, McHenry, MD 21541
    58 Bright Passage Rd Unit 6B, McHenry, MD 21541
    58 Bright Passage Rd Unit 6B, McHenry, MD 21541
    /54

    $382,500

    • 2 Beds
    • 3 Baths
    • 1,536 Sq Ft

    58 Bright Passage Rd Unit 6B, McHenry, MD 21541

    Lakeview townhome at Villages of Wisp just steps from the ski slopes and a short drive down the mountain to the community access to enjoy Deep Creek Lake! The perfect blend of mountain charm and lake-area convenience in this well-appointed getaway. Open kitchen/dining/living area with beautiful wood T&G accents, and a great view balcony. The primary suite is on the upper level and features a

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    58 Bright Passage Rd Unit 6B, McHenry, MD 21541
  • Lot 4A Shingle Camp Rd, Sang Run, MD 21541
    Lot 4A Shingle Camp Rd, Sang Run, MD 21541
    Lot 4A Shingle Camp Rd, Sang Run, MD 21541
    /14

    $625,000

    • Land
    • 1.38 Acres
    • $452,899 per Acre

    Lot 4A Shingle Camp Rd, Sang Run, MD 21541

    Don’t miss your opportunity to own a prime split lakefront homesite with a coveted Type A dock permit and 20’ of waterfront on Deep Creek Lake, offering the perfect blend of convenience and recreation. The lot boasts a two-story garage with a finished room above it. Enjoy breathtaking lake views and easy water access for boating, kayaking, and year-round enjoyment. Ideally located just minutes

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    Lot 4A Shingle Camp Rd, Sang Run, MD 21541

Showing Results 201 - 220, Page 6 of 6

Maryland Garrett County Oakland

Real Estate & Homes for Sale in 21550

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group