22

Oakland, MD Homes for Sale under $700,000

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  • 55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    /45

    $585,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,280 Sq Ft

    55 Village Dr Unit 5, Oakland, MD 21550

    Tucked in the Yellowstone Village community at Deep Creek Lake, “Dan’s Mountain” is a charming log cabin retreat offering the perfect blend of mountain serenity and convenient access to the area’s top attractions. This 3-bedroom, 3-bathroom home comfortably accommodates guests spanning over 3 levels with a bonus enlcosed porch area. Warm wood interiors and a classic cabin feel welcome you inside,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    55 Village Dr Unit 5, Oakland, MD 21550
  • 256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    /65

    $464,900

    • 3 Beds
    • 3.5 Baths
    • 1,838 Sq Ft

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    Looking for a beautifully updated condo at Deep Creek Lake? Welcome to 256 Jeffrey Lane #28, a spacious 3-bedroom, 3.5-bath condo in the desirable Traders Landing community. Enjoy filtered lake views from this well-appointed home, conveniently located just across the street from the water and only minutes from Wisp Resort, restaurants, shopping, marinas, and other area attractions. With a

    Larry Smith Railey Realty, Inc.

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
  • 428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    /86

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,542 Sq Ft

    428 Sam Snead Cir, Oakland, MD 21550

    Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan

    Justin Liller Railey Realty, Inc.

    428 Sam Snead Cir, Oakland, MD 21550
  • 20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    /68

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550

    With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /134

    $545,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    328 Stool Rock Rd, Oakland, MD 21550

    Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, 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

    $499,900

    $30K PRICE DROP
    • 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
  • 4A Mystic Creek Trail, Oakland, MD 21550
    4A Mystic Creek Trail, Oakland, MD 21550
    4A Mystic Creek Trail, 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
  • 308 Winding Trail Ln Unit 11B, Oakland, MD 21550
    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
    /61

    $615,000

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550

    5BR, 4.5BA duplex with LAKE VIEWS! Enjoy 3300sf of living space in the heart of Deep Creek Lake. Features include 3 spacious suites, multiple stacked stone fireplaces and two living room areas, plus an impressive outdoor fire pit. You will love the open kitchen/dining area and the covered back deck. Other features include wood floors, granite, instant hot water, pool table and hot tub. Attached

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
  • 97 acres Lot C Garrett Rd, Oakland, MD 21550
    97 acres Lot C Garrett Rd, Oakland, MD 21550
    97 acres Lot C Garrett Rd, Oakland, MD 21550
    /21

    $599,000

    • Land
    • 97.57 Acres
    • $6,139 per Acre

    97 acres Lot C Garrett Rd, Oakland, MD 21550

    Lot C – 97.57 Acres barn & ponds. | Oakland, Maryland. Discover 97.57 breathtaking acres just 10 minutes from Deep Creek Lake. This exceptional property offers a rare combination of natural beauty, privacy, and convenience, making it an ideal setting for a private estate, recreational retreat, or investment opportunity. The landscape is highlighted by two natural spring-fed and creek-fed ponds,

    Rich Orr Railey Realty, Inc.

    97 acres Lot C Garrett Rd, Oakland, MD 21550
  • 0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, 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
  • 511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    /51

    $424,900

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft

    511 Hilltop Rd, Oakland, MD 21550

    Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunning 4-bedroom, 3-bathroom home is the kind of property you'll fall in love with the moment you arrive. Surrounded by the beauty and tranquility of the mountains and accessed by county-maintained roads, this impeccably maintained home showcases pride of ownership throughout. From the expansive Trex decking that

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    511 Hilltop Rd, Oakland, MD 21550
  • 355 Markwood Dr, Oakland, MD 21550
    355 Markwood Dr, Oakland, MD 21550
    355 Markwood Dr, Oakland, MD 21550
    /63

    $569,000

    • 3 Beds
    • 2.5 Baths
    • 1,654 Sq Ft

    355 Markwood Dr, Oakland, MD 21550

    Fall in love with the perfect blend of comfort, privacy, and outdoor adventure in this beautifully maintained home nestled on 3.67 wooded acres overlooking scenic Meadow Lake. Thoughtfully designed for easy living, this 3-bedroom, 2.5-bath home features an open floor plan where the spacious great room flows seamlessly into a beautifully updated kitchen complete with granite countertops, making it

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    355 Markwood Dr, Oakland, MD 21550
  • 718 Boy Scout Crosscut Rd, Oakland, MD 21550
    718 Boy Scout Crosscut Rd, Oakland, MD 21550
    718 Boy Scout Crosscut Rd, Oakland, MD 21550
    /58

    $459,900

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft

    718 Boy Scout Crosscut Rd, Oakland, MD 21550

    Assumable 2.75% VA loan may be available...contact listing agent for details. If peace and privacy are on your must-have list, this one delivers! Picture this: you pull into the driveway and the trees close in around you on three sides, like the forest itself is standing guard. Over an acre of land, and somehow it stays flat and usable instead of the steep terrain so common in this area. This is

    Jeremy Cunningham Railey Realty, Inc.

    718 Boy Scout Crosscut Rd, Oakland, MD 21550
  • 178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    /47

    $559,000

    $30K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
  • 231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    /38

    $629,000

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

    231 Santa fe Trail, Oakland, MD 21550

    Brand new roof July 2026!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

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    231 Santa fe Trail, 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

    • 3 Beds
    • 3.5 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
  • 170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    /69

    $699,000

    • 5 Beds
    • 3 Baths
    • 2,560 Sq Ft

    170 Cherrywood Dr, Oakland, MD 21550

    Private Mountain Retreat on 8+ Acres Near Oakland Discover the peace and beauty of Garrett County living on over 8 private wooded acres filled with mountain views, abundant wildlife, and endless opportunities to enjoy the outdoors. Deer, turkey, songbirds, and other native wildlife are frequent visitors, creating a true nature lover's paradise. Conveniently located just minutes from Oakland's

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    170 Cherrywood Dr, Oakland, MD 21550
  • 193 Red Run Rd Unit 1B3, Oakland, MD 21550
    193 Red Run Rd Unit 1B3, Oakland, MD 21550
    193 Red Run Rd Unit 1B3, Oakland, MD 21550
    /57

    $595,000

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    193 Red Run Rd Unit 1B3, Oakland, MD 21550

    Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a

    John McNamara RE/MAX Results

    193 Red Run Rd Unit 1B3, Oakland, MD 21550
  • 995 Betts Ln, Oakland, MD 21550
    995 Betts Ln, Oakland, MD 21550
    995 Betts Ln, Oakland, MD 21550
    /45

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    995 Betts Ln, Oakland, MD 21550

    4BR 2.5BA cabin in the woods! Over 12 wooded acres of privacy and seclusion, laced with trails and surrounded by low maintenance land. Centrally located - only a few miles to Deep Creek Lake, town of Oakland or Swallow Falls State Park. Open floor plan with vaulted ceilings, a wood burning stove and high end finishes throughout. Basement is partially finished. Spacious decking and a must-have

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    995 Betts Ln, Oakland, MD 21550
  • 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
  • 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
Maryland Garrett County

Real Estate & Homes in Oakland, MD under $700,000

Home Prices in Oakland, MD

The median home sale price in Oakland, MD is $405,000, up 1% year-over-year. Homes in Oakland sell in 98 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$405,000
Median Single Family Sale Price
$405,000
Median Townhouse Sale Price
$462,450
Median 2 Bedroom Sale Price
$285,000
Median 1 Bedroom Sale Price
$221,950
Average Price Per Sq Ft
$273
Number of Homes for Sale
65
Last 12 months Home Sales
142
Months of Supply
5.50
Median List Price
$422,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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