28

Oakland, MD Homes for Sale under $100,000

Section Image Section Image
  • 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
  • Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    /16

    $40,000

    • Land
    • 0.6 Acre
    • $66,667 per Acre

    Lot 2 Cedar Ln, Oakland, MD 21550

    Cleared, perc approved and ready to build! Lot 2 Cedar Lane sits on a 0.6 acre level lot at the beginning of Cedar Lane which sits close to the community center, tennis courts, pavilion and only a short ride to Muddy Creek and the access to Youghiogheny River! Youghiogheny Mountain Resort offers over 50 miles of trails for riding ATV’s, side by sides, fishing at Muddy Creek and much more! The

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 594-8377

    Lot 2 Cedar Ln, Oakland, MD 21550
  • Lot 13 Dogwood Dr, Oakland, MD 21550
    Lot 13 Dogwood Dr, Oakland, MD 21550
    Lot 13 Dogwood Dr, Oakland, MD 21550
    /21

    $22,500

    • Land
    • 0.58 Acre
    • $38,793 per Acre

    Lot 13 Dogwood Dr, Oakland, MD 21550

    Discover the perfect blend of privacy and potential with these two adjoining lots located in the Youghiogheny Mountain Resort community. Lot 13 Dogwood Drive offers 0.58 wooded acres of mountain serenity. Lot 13 is approved for a sand mound septic system, making it an ideal site for your future mountain cabin or getaway retreat. The community offers gated access, over 50 miles of community roads

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-5545

    Lot 13 Dogwood Dr, 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
  • Lot 17 Birchwood Dr, Oakland, MD 21550
    Lot 17 Birchwood Dr, Oakland, MD 21550
    Lot 17 Birchwood Dr, Oakland, MD 21550
    /10

    $5,000

    • Land
    • 0.65 Acre
    • $7,692 per Acre

    Lot 17 Birchwood Dr, Oakland, MD 21550

    Lot 17 Birchwood Drive is a .65-acre wooded, NON-BUILDABLE membership lot located in the Youghiogheny Mountain Resort community in Oakland, MD. Nestled among mature trees, this lot's ownership offers full membership access to the community’s amenities, including over 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, and outdoor recreation. Ideal for outdoor

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 512-9707

    Lot 17 Birchwood Dr, Oakland, MD 21550
  • 0 N Hammond St, Oakland, MD 21550
    0 N Hammond St, Oakland, MD 21550
    /2

    $29,900

    • Land
    • 0.48 Acre
    • $62,292 per Acre

    0 N Hammond St, Oakland, MD 21550

    A practical, in‐town lot close to everything that quaint downtown Oakland has to offer. You are just minutes to local shops, schools, and restaurants. Public utilities are available and easy access to main roads, making the possibilities endless.

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 N Hammond St, Oakland, MD 21550
  • 809 N St, Oakland, MD 21550
    809 N St, Oakland, MD 21550
    809 N St, 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
  • Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
    Lot 55 Gallatin Dr Unit 55, 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
  • 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 Rhododendron Unit MDGA2010748, Oakland, MD 21550
    0 Rhododendron Unit MDGA2010748, 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
  • 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 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
  • Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    /11

    $5,000

    • Land
    • 0.96 Acre
    • $5,208 per Acre

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550

    Discover the perfect mountain getaway in Yough Mountain Resort, a gated community nestled in the scenic mountains of western Maryland, just minutes from Deep Creek Lake. This amenity-rich community offers an outdoor enthusiast’s dream with ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering and relaxing.

    Mike Kennedy Railey Realty, Inc.

    Lots 34 & 35 Fox Tail 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
    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
  • 60 Gorman St, Oakland, MD 21550
    60 Gorman St, Oakland, MD 21550
    60 Gorman St, 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
  • 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
  • 3501 George Washington Hwy, Oakland, MD 21550
    3501 George Washington Hwy, Oakland, MD 21550
    3501 George Washington Hwy, 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
  • Lot 54 Gallatin Spur Rd, Oakland, MD 21550
    Lot 54 Gallatin Spur Rd, Oakland, MD 21550
    Lot 54 Gallatin Spur 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
  • 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
  • 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
  • LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, Oakland, MD 21550
    /12

    $45,000

    • Land
    • 0.34 Acre
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, 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
  • Lot 40 W Big Piney Dr, Oakland, MD 21550
    Lot 40 W Big Piney Dr, Oakland, MD 21550
    Lot 40 W Big Piney Dr, Oakland, MD 21550
    /8

    $17,000

    • Land
    • 0.77 Acre
    • $22,078 per Acre

    Lot 40 W Big Piney Dr, Oakland, MD 21550

    Located in the Youghiogheny Mountain Resort community, this .77ac lot offers the ultimate gateway to peaceful surroundings, beautiful views, and abundant wildlife. Approved for a sand mound sewage system, this lot provides the perfect opportunity to build your future outdoor enthusiast retreat! Enjoy exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    Lot 40 W Big Piney Dr, Oakland, MD 21550
  • 0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    /4

    $51,000

    • Land
    • 7.02 Acres
    • $7,265 per Acre

    0 Bethlehem Rd, Oakland, MD 21550

    LOT B= 7.02 acre parcel, located off Bethlehem Rd, in Western Maryland! Adjoins lot A (8.73 acres) 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, shopping and

    Thomas Long Railey Realty, Inc.

    0 Bethlehem Rd, Oakland, MD 21550
  • LOT 2 Beaver Run Rd, Oakland, MD 21550
    LOT 2 Beaver Run Rd, Oakland, MD 21550
    LOT 2 Beaver Run Rd, Oakland, MD 21550
    /9

    $3,500

    • Land
    • 0.48 Acre
    • $7,292 per Acre

    LOT 2 Beaver Run Rd, Oakland, MD 21550

    Tucked away in the stunning mountains of Western Maryland, this unbuildable lot provides a serene escape into nature, offering breathtaking views and abundant wildlife. Located in the Youghiogheny Mountain Resort, this membership-only lot grants exclusive access to over 50 miles of private roads and trails, ideal for ATV and side-by-side adventures. Resort amenities include a community clubhouse,

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    LOT 2 Beaver Run Rd, 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 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
  • 1358 Crellin Underwood Rd, Oakland, MD 21550
    1358 Crellin Underwood Rd, Oakland, MD 21550
    1358 Crellin Underwood Rd, Oakland, MD 21550
    /37

    $85,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    1358 Crellin Underwood Rd, Oakland, MD 21550

    Charming 2-bedroom, 1-bath home offering a fantastic opportunity for buyers looking to add their own personal touch. Recent updates include a metal roof, 2 propane wall unit heaters, and a hot water heater. Enjoy the back covered deck overlooking the woods and the youghiogheny river below. This property needs a bit of TLC but is full of potential and character. Located in a highly desirable

    Lucas Muenchow Railey Realty, Inc.

    1358 Crellin Underwood Rd, Oakland, MD 21550
  • 3416 Broadford Rd, Oakland, MD 21550
    3416 Broadford Rd, Oakland, MD 21550
    3416 Broadford Rd, Oakland, MD 21550
    /23

    $85,000

    • 3 Beds
    • 1 Bath
    • 1,462 Sq Ft

    3416 Broadford Rd, Oakland, MD 21550

    Charming ranch-style cottage nestled in a beautiful, peaceful setting. This 3-bedroom, 1-bath home, situated on a 1.12-acre lot, features an enclosed porch, perfect for enjoying the surrounding nature year-round. A small natural run, Broadford Run, gently crosses the property, adding to the serene atmosphere. The property also offers a detached garage and a newer roof, providing a solid starting

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    3416 Broadford Rd, Oakland, MD 21550
Maryland Garrett County Oakland

Real Estate & Homes in Oakland, MD under $100,000

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 87 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 $450,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$450,000
Median Single Family Sale Price
$433,000
Median Townhouse Sale Price
$485,000
Median 2 Bedroom Sale Price
$324,000
Median 1 Bedroom Sale Price
$219,450
Average Price Per Sq Ft
$267
Number of Homes for Sale
43
Last 12 months Home Sales
135
Months of Supply
3.80
Median List Price
$442,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
13%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 28 homes for sale priced under $100,000, providing budget-friendly options for prospective buyers. Whether you're in search of houses for sale under 100k or other property types, there are opportunities to discover your ideal home within your budget in Oakland, MD. From cozy starter homes to properties awaiting your personal touch, these affordable residences offer an entry point into the housing market or an opportunity for real estate investment without stretching your finances.

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