131

Oakland, MD Homes for Sale

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  • 220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    /85

    $775,000

    • 5 Beds
    • 3 Baths
    • 2,660 Sq Ft

    220 Woodlands Hill Ln, Oakland, MD 21550

    Discover this spacious 5-bedroom, 3-bath chalet in The View community at Deep Creek Lake, offering three finished levels of comfortable living and a strong history as the well-known rental 'Divided Sky'. The foyer greets you with a beautiful built-in for hanging jackets, leave your ski boots on the convenient tile floor and proceed in to the main level, where two-story ceilings paneled in solid

    Ana Dubin RE/MAX Realty Group

    220 Woodlands Hill Ln, Oakland, MD 21550
  • 3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    /8

    $280,000

    • Land
    • 36.72 Acres
    • $7,625 per Acre

    3257 George Washington Hwy, Oakland, MD 21550

    Discover approximately 36.72 acres of beautiful 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. Located within a 30-minute drive of Deep Creek Lake and Wisp Resort, as well as sought-after West Virginia

    Justin Liller Railey Realty, Inc.

    3257 George Washington Hwy, 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
  • 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
  • 3.35 acres </> 4th St, Oakland, MD 21550
    3.35 acres </> 4th St, Oakland, MD 21550
    3.35 acres </> 4th St, Oakland, MD 21550
    /3

    $150,000

    • Land
    • 3.4 Acres
    • $44,118 per Acre

    3.35 acres </> 4th St, Oakland, MD 21550

    Just over three acres in a prime location in Oakland, Maryland. Property borders the south side of Wal-Mart property and has deeded access from the south entrance of Wal-Mart. Property is wooded but has several flat spots perfect for building. Owner has hired a civil engineer to draw plans for a restaurant, and an office building. Plans are available for review.

    Andrew Orr The KW Collective

    3.35 acres </> 4th St, Oakland, MD 21550
  • 141 Truesdale Rd, Oakland, MD 21550
    141 Truesdale Rd, Oakland, MD 21550
    141 Truesdale Rd, Oakland, MD 21550
    /7

    $185,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    141 Truesdale Rd, Oakland, MD 21550

    Bring your vision and put your own personal touch on this great starter home! This property has great bones and endless potential. Featuring three bedrooms, two and a half bathrooms, and a large/open family room; it’s ready for your creative touch. Offering a nice level yard on a dead-end lane, which feels very private. The attached 1-car garage and rear shed provide the perfect extra storage

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    141 Truesdale Rd, Oakland, MD 21550
  • 34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook Dr, Oakland, MD 21550
    34 Laurel Brook Dr, Oakland, MD 21550
    /34

    $299,500

    • 3 Beds
    • 3 Baths

    34 Laurel Brook Dr, Oakland, MD 21550

    Welcome to 34 Laurel Brook Drive! An impeccably remodeled townhome just moments from Deep Creek Lake and Oakland, Maryland. Renovated in 2019 and among the larger homes in the neighborhood, this property features 3 bedrooms, 3 full bathrooms, and over 2,000 sq ft of finished space. Highlights include stylish flooring, a modern kitchen, and recent upgrades such as new skylights and primary bedroom

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    34 Laurel Brook Dr, Oakland, MD 21550
  • 565 Glendale Rd Unit 204B, Oakland, MD 21550
    565 Glendale Rd Unit 204B, Oakland, MD 21550
    565 Glendale Rd Unit 204B, Oakland, MD 21550
    /51

    $195,000

    • 1 Bed
    • 1 Bath
    • 460 Sq Ft

    565 Glendale Rd Unit 204B, Oakland, MD 21550

    Don’t miss this opportunity to own a beautifully updated 1-bedroom unit at Silver Tree Suites on Deep Creek Lake! This turn-key condo features recent flooring upgrades and is truly turn key, making it an ideal vacation retreat or income-producing rental. This particular unit offers a unique L-shaped layout, providing extra square footage and a more spacious feel compared to other efficiency

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 204B, Oakland, MD 21550
  • 565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    /53

    $260,000

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites! This inviting one-bedroom layout features a gas fireplace, full bath with tub/shower, and a tidy kitchenette equipped with a microwave, dishwasher, and full-size refrigerator. Balcony doors open to fresh Deep Creek air and filtered lake views, with a private deck that is perfect for relaxing after a day on the water. Enjoy a variety of

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, 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
  • 170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    /12

    $129,900

    • Land
    • 1.38 Acres
    • $94,130 per Acre

    170 San Francisco St, Oakland, MD 21550

    NEW in the Deep Creek Lake and WISP Resort area: three lots at .46 acres each (total is 1.38 acres)! Whether you envision a cozy cabin or a luxury lodge, this parcel offers the ideal blend of seclusion and accessibility. Property Highlights: Private well water source already in place, 200 AMP electric service connection, Approved perc test suitable for a 4-5 bedroom home, Privacy with

    Hunter Shank Coldwell Banker Realty

    170 San Francisco St, 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
  • 157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    /21

    $305,000

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    Tastefully updated 2BR/1BA condo with sweeping Deep Creek Lake and mountain views and a rare expanded deck—larger than most along Jeffrey Lane—for standout outdoor living. Sun-filled, open-concept layout with abundant windows and seamless flow to the oversized deck. Centrally located to Wisp Resort, state parks, restaurants, and marinas. Offered fully furnished and turn-key. Seasonal boat slips

    James Matthews Taylor Made Deep Creek Vacations & Sales

    157 Jeffrey Ln Unit 21C, 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

    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 memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace,

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • 181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    /25

    $269,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
  • Lots 13/17 Dogwood Dr, Oakland, MD 21550
    Lots 13/17 Dogwood Dr, Oakland, MD 21550
    Lots 13/17 Dogwood Dr, Oakland, MD 21550
    /26

    $32,000

    • Land
    • 1.23 Acres
    • $26,016 per Acre

    Lots 13/17 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 and Lot 17 Birchwood Drive together offer 1.23 wooded acres of mountain serenity, with the rear property lines connected for an expansive feel and extra buffer from neighbors. Lot 13 is approved for a sand mound septic system, making it an

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-6552

    Lots 13/17 Dogwood Dr, 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
  • 123 Mountainview Ct, Oakland, MD 21550
    123 Mountainview Ct, Oakland, MD 21550
    123 Mountainview Ct, Oakland, MD 21550
    /20

    $221,000

    • Land
    • 1.69 Acres
    • $130,769 per Acre

    123 Mountainview Ct, Oakland, MD 21550

    One of the best lake view lots at Deep Creek Lake! Big mountain and water views from this 1.67 acre homesite in the private community of Mountainside. Lake access with public sewer available. This lot sits at the top of the ridge with quiet surroundings, yet still close to Wisp Resort, marinas, restaurants, and local establishments. Mountainside offers a private marina club, tennis and basketball

    Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
  • 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
  • 47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    /109

    $6,499,900

    • 8 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, Oakland, MD 21550
  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /29

    $315,000

    • 4 Beds
    • 2 Baths
    • 2,183 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Cozy, well maintained 4 bedroom, 2 bathroom ranch style home with full finished basement on a corner lot in Mountain Lake Park. Beautifully finished Hardwood flooring on main level, with a large kitchen/dining area, living room, three bedrooms, and a full bathroom. In the lower level, there is a large family room, full bathroom, a bedroom, and bonus room, that has been used for storage, an

    Andrew Orr The KW Collective

    127 S Oakhall Dr, 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
  • 63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    /60

    $179,900

    • 3 Beds
    • 1 Bath
    • 816 Sq Ft

    63 Wallman Rd, Oakland, MD 21550

    Remodeled Rancher Near the North Branch Potomac RiverThis charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep.A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot

    Rich Orr Railey Realty, Inc.

    63 Wallman Rd, Oakland, MD 21550
  • 18 Hoye Crest Rd, Oakland, MD 21550
    18 Hoye Crest Rd, Oakland, MD 21550
    18 Hoye Crest Rd, Oakland, MD 21550
    /9

    $29,900

    • Land
    • 7.51 Acres
    • $3,981 per Acre

    18 Hoye Crest Rd, Oakland, MD 21550

    Discover this beautifully wooded 7.51-acre lot located in a scenic mountain development featuring the highest point in Maryland. With an approved 5-bedroom perc, this property is ready for your dream home or mountain getaway. Enjoy the peace and privacy of nature while still being part of an established community. Exceptionally priced at just $29,900!

    Kellyann Green Railey Realty, Inc.

    18 Hoye Crest Rd, Oakland, MD 21550
  • 0 Meadow Ct Unit MDGA2010558, Oakland, MD 21550
    0 Meadow Ct Unit MDGA2010558, Oakland, MD 21550
    0 Meadow Ct Unit MDGA2010558, Oakland, MD 21550
    /13

    $99,900

    • Land
    • 1.7 Acres
    • $58,765 per Acre

    0 Meadow Ct Unit MDGA2010558, Oakland, MD 21550

    Ready to bring your Deep Creek Lake dream home to life? This beautiful 1.7-acre lot in the sought after community of Paradise Ridge offers the perfect blend of peace, privacy, and lake access. Spend your summer days down by the water, where owners enjoy access to one of the area’s best lakefront spots, complete with a sandy beach, picnic pavilions, and kayak or swimming areas. When the day winds

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    0 Meadow Ct Unit MDGA2010558, Oakland, MD 21550
  • 282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    /150

    $4,200,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 4,354 Sq Ft

    282 McComas Beach Terrace, Oakland, MD 21550

    Discover The Birch Bower, a rare architect-designed lakefront sanctuary offering 600 feet of private shoreline on Deep Creek Lake. Completed in 2021, this 6-bedroom, 5.5-bath residence exemplifies modern luxury, combining meticulous design, serene natural surroundings, and proven short-term rental performance. Offered turn-key and fully furnished, this extraordinary lakefront estate presents a

    Morgan Boyer Hunt Country Sotheby's International Realty

    282 McComas Beach Terrace, Oakland, MD 21550
  • 0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    /55

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft

    0 Crosby Dr Unit 64/65, Oakland, MD 21550

    TO BE BUILT on lots 64 & 65 Country Club Acres - 3BR, 2BA new construction with full walkout basement & attached 2 car garage fronting on hole #13 of the Oakland golf course. Impressive views from .61+/- acres of land, rare privacy and modern floor plan. 1,986 sf of finished living space on the first floor and 1,986 sq ft unfinished basement will have a full bath rough-in and can be finished

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Crosby Dr Unit 64/65, Oakland, MD 21550
  • 340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    /84

    $949,900

    • 6 Beds
    • 4 Baths
    • 2,536 Sq Ft

    340 Grandview Dr, Oakland, MD 21550

    Lake Access property overlooking Cherry Creek Cove in the coveted Mountainside community, at 2,536 square feet, this fully furnished retreat pairs modern comfort with timeless mountain style. Freshly updated from top to bottom, with a new roof and deck staining, every detail feels dialed in. A wall of glass and open layout connects bright gathering spaces with panoramic lake views that steal the

    Jon Bell Railey Realty, Inc.

    340 Grandview Dr, Oakland, MD 21550
  • 102 Roanoke Ave, Oakland, MD 21550
    102 Roanoke Ave, Oakland, MD 21550
    102 Roanoke Ave, Oakland, MD 21550
    /7

    $149,000

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    102 Roanoke Ave, Oakland, MD 21550

    4-bedroom, 1.5-bath home located on a spacious corner lot in Loch Lynn. This two-story property features generous living space and several recent updates, including a new furnace, roof, windows, and stove. A newer deck offers additional outdoor enjoyment. The home is conveniently located near the Loch Lynn soccer fields and just a few minutes from downtown Oakland. Solid structure with great

    Heather Homberg Taylor Made Deep Creek Vacations & Sales

    102 Roanoke Ave, Oakland, MD 21550
  • 77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, Oakland, MD 21550
    /65

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft

    77 Meadow Ct, Oakland, MD 21550

    Lake Access Chalet at Deep Creek Lake – Featured on HGTV’s Lakefront Bargain Hunt, this property is quietly tucked away on over half an acre on rolling mountain pasture in the sought after Paradise Ridge community, and pairs rustic comfort with clean, modern lines. Warm wood tones, vaulted ceilings, and a two-story stone fireplace anchor the main level. Open kitchen and dining area flow into a

    Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
  • 111 Knoll Crest Heights Dr, Oakland, MD 21550
    111 Knoll Crest Heights Dr, Oakland, MD 21550
    111 Knoll Crest Heights Dr, Oakland, MD 21550
    /33

    $189,900

    • 4 Beds
    • 2 Baths
    • 3,504 Sq Ft

    111 Knoll Crest Heights Dr, Oakland, MD 21550

    AS-IS Sale. Fix it up and make it your own or investment potential for renovation and sell. This large spacious home is just minutes from downtown Oakland’s shopping, dining, schools, and Garrett Regional Medical Center. Inside, you’ll find a comfortable and functional floor plan ready for your personal touch. The 2-car attached garage with a large unfinished space above for storage. Whether

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    111 Knoll Crest Heights Dr, Oakland, MD 21550
  • 329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    /81

    $750,000

    • 4 Beds
    • 3.5 Baths
    • 2,632 Sq Ft

    329 Lemley Dr, Oakland, MD 21550

    Lake View Chalet at Deep Creek Lake – This 4 Bedroom 3.5 Bath Mountain Home is privately seated on 1.72 acres of wooded land and features vaulted ceilings, an oversized loft, 2 gas fireplaces, and seasonal views of Deep Creek Lake! Open layout with hardwood floors and custom built-in bookshelves. Walk-out basement with 2nd living space and a pool table. Two stories of outdoor living with upper

    Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    5024 Cranesville Rd, Oakland, MD 21550

    Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1.68-acre hillside in a beautiful conservation area, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence.Inside, the main level features a spacious primary suite with a jetted tub, double vanity, and shower, a

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • 3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    /31

    $1,800,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    One of a kind 4 BR 4 BA brick Home. 5,100 sq. ft. + 3 car garage. Situated on 23.47 elevated acres with unbelievable panoramic views of Pleasant Valley and surrounding farming community. Living area on one level with full unfinished basement. Views from every room. Massive amount of closet space The opportunities are abundant with this property.

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, 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
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /50

    $379,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    961 Cedar Ln, Oakland, MD 21550
  • 1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    /82

    $865,000

    • 4 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    1909 Pysell Crosscut Rd, Oakland, MD 21550

    Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style.The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs,

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • 697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    /56

    $359,000

    • 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
  • 39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    /33

    $950,000

    • 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
  • 0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    /24

    $279,900

    • Land
    • 3.32 Acres
    • $84,307 per Acre

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550

    REMARKS: OAKLAND, MD – 3.318 UNRESTRICTED ACRES “READY TO BUILD” THAT VACATION HOME OR FULL TIME RESIDENCE. THE SUBJECT PROPERTY IS IN THE DEEP CREEK LAKE RESORT AREA. ALL AMENITIES ASSOCIATED WITH A MAJOR RESORT AREA ARE WITHIN A SHORT DRIVE OF THE SUBJECT PROPERTY. FULLY WOODED. MATURE HARDWOOD THRU-OUT. LEVEL TOPOGRAPHY. CLOSE PROXIMITY TO BOAT LAUNCH.

    Mike Haywood The Mike Haywood Group

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 4

Maryland Garrett County Oakland

Real Estate & Homes for Sale in Oakland, MD

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $557,983.
Are home prices dropping in Oakland?
Yes, home prices in Oakland are down 8% in the last 12 months.
How many homes have sold over the last 12 months in Oakland, MD?
134 homes have sold in Oakland, MD over the last 12 months.
What are the most popular zip codes in Oakland, MD?
The most popular zip codes in Oakland, MD include 21550, 26764, 21561, 21541 and 26705.
How much do you need to make to afford a house in Oakland?
The median home price in Oakland is $430,000. If you put a 20% down payment of $86,000 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $2,120 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $91K a year to afford the median home price in Oakland. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Oakland, MD?
Oakland, MD has highly rated public and private schools. Some of the best schools in Oakland based on Niche Grades are Swan Meadow School, Crellin Elementary School and Southern Middle School. Browse all the schools in Oakland, MD to learn more.

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 86 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 $435,000, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$435,000
Median Single Family Sale Price
$420,000
Median Townhouse Sale Price
$485,000
Median 2 Bedroom Sale Price
$326,000
Median 1 Bedroom Sale Price
$229,000
Average Price Per Sq Ft
$257
Number of Homes for Sale
50
Last 12 months Home Sales
134
Months of Supply
4.50
Median List Price
$430,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
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