156

Oakland, MD Homes for Sale

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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
  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /57

    $265,000

    $34K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,913 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    127 S Oakhall Dr, Oakland, MD 21550
  • Lot 24 Eastview Ct, Oakland, MD 21550
    Lot 24 Eastview Ct, Oakland, MD 21550
    Lot 24 Eastview Ct, Oakland, MD 21550
    /21

    $30,000

    $19K PRICE DROP
    • Land
    • 1.01 Acres
    • $29,703 per Acre

    Lot 24 Eastview Ct, Oakland, MD 21550

    The perfect setting for your Deep Creek Lake getaway! Lot 24 Eastview Place is a 1.01-acre homesite in the Overlook community, offering water access to Deep Creek Lake. Situated on a quiet cul-de-sac, this cleared lot is ready for your dream home with approval already in place for a 3-bedroom septic system. Enjoy the ideal blend of privacy and convenience, just minutes from local dining,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    Lot 24 Eastview Ct, Oakland, MD 21550
  • Lot 9 Woodlands Hill Ln, Oakland, MD 21550
    Lot 9 Woodlands Hill Ln, Oakland, MD 21550
    Lot 9 Woodlands Hill Ln, Oakland, MD 21550
    /13

    $95,000

    • Land
    • 2.08 Acres
    • $45,673 per Acre

    Lot 9 Woodlands Hill Ln, Oakland, MD 21550

    2.08 acre corner building lot in The View community at Deep Creek Lake! The lot is approved for up to a 6 bedroom septic system - a rare find which offers added flexibility for your future mountain or lake area home. Mostly wooded setting with convenient access off Lakeshore Drive and close proximity to Deep Creek Lake, Wisp Resort, restaurants, shopping, and local attractions. Lot 10 is also

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    Lot 9 Woodlands Hill Ln, 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.

    Lot 6 Hoye Crest Rd, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    /29

    $294,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

    Nestled in the charming Traders Landing community, this delightful end-of-row townhouse offers a perfect blend of comfort and convenience with one of the best unobstructed views of the lake in Traders Landing. This villa-style home features two cozy bedrooms and a full bathroom, ideal for relaxation and unwinding after a long day. The inviting living space is enhanced by a warm wood-burning

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • 0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    /5

    $250,000

    • Land
    • 6.89 Acres
    • $36,284 per Acre

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550

    6.89 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to all area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, 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
    • 28,314 Sq Ft
    • $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. While you cannot build on this lot, 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

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    Lot 17 Birchwood Dr, 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

    $85,000

    • Land
    • 1.08 Acres
    • $78,704 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.

    Lot 18 Laurel Ct, 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

    $125,000

    • Land
    • 1.38 Acres
    • $90,580 per Acre

    170 San Francisco St, Oakland, MD 21550

    1.38 acres in Deep Creek Lake and WISP Resort area! 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 convenience; close to main roads, yet tucked away for peace

    Agent Photo

    Hunter Shank

    Coldwell Banker Realty

    170 San Francisco St, Oakland, MD 21550
  • 565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    /20

    $175,000

    • 1 Bed
    • 1 Bath
    • 527 Sq Ft

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550

    Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western exposure centrally located to all area amenities. Unit 212A offers a one level floorpan with private bedroom on the second floor of building A which offers easy access to the lobby, elevator, gym, sauna, game room and patio area overlooking the lake. Condominium ownership at Silver Tree Suites offers ease of

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
  • 660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    /62

    $1,100,000

    $200K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,592 Sq Ft

    660 Glendale Rd, Oakland, MD 21550

    Welcome to 660 Glendale Road — a luxury, mountain-chalet log home in the heart of Deep Creek Lake. This well appointed 5-bedroom, 3-bath home offers nearly 2,600 square feet of thoughtfully upgraded living space designed for lake life at its best. Enjoy lake views with western exposure on the expansive wraparound decks on main and lower levels. Many recent upgrades including roof, decks, covered

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    660 Glendale Rd, Oakland, MD 21550
  • 211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    /99

    $1,350,000

    $145K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    211 High Point Ridge Rd, Oakland, MD 21550

    Once in a lifetime opportunity to own one of Maryland’s most distinctive homes. Built in 2019, this fully custom modern home is located on the highest elevation building lot in the state of Maryland, making it the highest elevation home in the state at over 3300 feet above sea level. Designed to take full advantage of the setting, the property offers incredible panoramic views stretching across

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    211 High Point Ridge Rd, Oakland, MD 21550
  • 0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    /3

    $200,000

    • Land
    • 3.15 Acres
    • $63,492 per Acre

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550

    3.15 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities. No HOA.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    /27

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    20160 Garrett Hwy Unit H706, 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

    $35,000

    $15K PRICE DROP
    • Land
    • 26,136 Sq Ft
    • $58,333 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.

    Lot 2 Cedar Ln, Oakland, MD 21550
  • 0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    /3

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    0 5 Acres Lake Shore Dr, Oakland, MD 21550

    5.0 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 5 Acres Lake Shore Dr, 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
    • 25,264 Sq Ft
    • $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.

    Lot 13 Dogwood Dr, Oakland, MD 21550
  • 122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    /56

    $1,200,000

    • 4 Beds
    • 4.5 Baths
    • 2,656 Sq Ft

    122 Woodlands Hill Ln, Oakland, MD 21550

    Outdoor lovers retreat! Wooded trails and hunting available with no HOA restrictions. Welcome to mountain and lake living at its finest. Nestled on 6.89 very private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings in the heart of Deep Creek Lake. This impressive 4-bedroom, 4.5-bath home features

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    122 Woodlands Hill Ln, Oakland, MD 21550
  • Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    /25

    $124,000

    $6K PRICE DROP
    • Land
    • 2.1 Acres
    • $59,048 per Acre

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550

    Lot 20 Paradise Ridge offers a mountaintop setting with exceptional lake and mountain views facing east toward Backbone Mountain. Enjoy relaxing morning sunrises, lake access at one of Deep Creek Lake's most premier water access points and a location that feels like you are truly away, yet only a few minutes to the most important amenities you come to enjoy here at the lake. Approved perc site on

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    Lot 20 Paradise Ridge Rd, 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
  • 163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    /60

    $279,000

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, Oakland, MD 21550
  • 101 Sobriety Way, Oakland, MD 21550
    101 Sobriety Way, Oakland, MD 21550
    101 Sobriety Way, Oakland, MD 21550
    /72

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    101 Sobriety Way, Oakland, MD 21550

    Wake up to breathtaking views of Deep Creek Lake every single day from this beautifully updated 3-bedroom home, complete with private lake access in a quiet, peaceful cove. Huge windows throughout invite in an abundance of natural light while framing the surrounding scenery, blurring the line between indoors and out. The open-concept kitchen features beautiful new quartz countertops and flows

    Brent Housley Railey Realty, Inc.

    101 Sobriety Way, Oakland, MD 21550
  • 941 Mountainview Dr, Oakland, MD 21550
    941 Mountainview Dr, Oakland, MD 21550
    941 Mountainview Dr, Oakland, MD 21550
    /71

    $737,500

    • 4 Beds
    • 3.5 Baths
    • 4,377 Sq Ft

    941 Mountainview Dr, Oakland, MD 21550

    Experience the best of Deep Creek Lake living in this thoughtfully designed 4 bedroom, 3.5 bath home located in the highly desirable Mountainside community. Combining quality craftsmanship with inviting living spaces, the well planned floor plan maximizes both comfort and functionality. Situated on over an acre, the expansive outdoor living area features a wrap around porch and private hot tub,

    Nicole Jackson Railey Realty, Inc.

    941 Mountainview Dr, Oakland, MD 21550
  • 943 Paradise Heights, Oakland, MD 21550
    943 Paradise Heights, Oakland, MD 21550
    943 Paradise Heights, Oakland, MD 21550
    /62

    $765,000

    • 5 Beds
    • 3 Baths
    • 2,200 Sq Ft

    943 Paradise Heights, Oakland, MD 21550

    Welcome to this stunning 5-bedroom, 3-bath home, completed in 2023 and designed for modern mountain living. Featuring two private ensuite bedrooms, spacious living areas, and a fresh, contemporary design, this home is ready for you to enjoy from day one. This home features a stylish modern kitchen with an open layout that is perfect for entertainment. In the winter months, cozy up by the wood

    Lucas Muenchow Railey Realty, Inc.

    943 Paradise Heights, Oakland, MD 21550
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /45

    $1,329,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, Oakland, MD 21550
  • 113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    /69

    $869,900

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,185 Sq Ft

    113 Jubb Meadows Ln, Oakland, MD 21550

    Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 acres. Offering 4,555 sq ft with vaulted ceilings, open concept living, and a rustic stacked stone fireplace. Modern gourmet kitchen with a large island and granite tops. Hardwood floors and timber frame accents throughout. Attached three-car garage. Full unfinished basement ready to add up to an additional

    Jon Bell Railey Realty, Inc.

    113 Jubb Meadows Ln, 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
  • 1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    /61

    $369,000

    $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Log cabin on 11 private acres. Located in the gated Timbers on the Yough community. The community features shared access to the Youghiogheny River. Home features include spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. Heart pine floors on main floor and stairs, reclaimed from RJ Reynolds tobacco factory built around 1900! The primary bath offers

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, 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
  • 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
  • 670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    /72

    $1,649,000

    $40K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,714 Sq Ft

    670 Woodlands Hill Ln, Oakland, MD 21550

    Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury

    Nina Beitzel Railey Realty, Inc.

    670 Woodlands Hill Ln, Oakland, MD 21550
  • 2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    /11

    $199,900

    $20K PRICE DROP
    • Land
    • 4,791 Sq Ft
    • $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
  • 3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    /31

    $1,650,000

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

    3898 Underwood Rd, Oakland, MD 21550

    Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • 0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
    /21

    $975,000

    $20K PRICE DROP
    • Land
    • 25,264 Sq Ft
    • $1,681,034 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
  • 222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    /59

    $729,000

    $50K PRICE DROP
    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lake cottage (5 Bedrooms) on large level lot with path to your own private class A dock & 25' of Lakefront, directly across the street. This comfy (one level living) cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, with 5 Bedrooms! Laundry room located off back of the home. Cute

    Julie Mead The KW Collective

    222 Skippers Point 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
  • 9.75 AC. Dennett Rd, Oakland, MD 21550
    9.75 AC. Dennett Rd, Oakland, MD 21550
    9.75 AC. Dennett Rd, Oakland, MD 21550
    /30

    $169,000

    • Land
    • 9.75 Acres
    • $17,333 per Acre

    9.75 AC. Dennett Rd, Oakland, MD 21550

    9.75 acres of prime land in a highly convenient Oakland location! This versatile property offers outstanding potential for development or the ideal setting for a private estate-sized homesite. Seller has already completed a proposed subdivision engineering plan, providing added value and future possibilities. Public water and sewer taps available per Oakland Town Administrator. Gently rolling

    Nina Beitzel Railey Realty, Inc.

    9.75 AC. Dennett Rd, Oakland, MD 21550
  • Lot 233 Cumberland Rd, Oakland, MD 21550
    Lot 233 Cumberland Rd, Oakland, MD 21550
    Lot 233 Cumberland Rd, Oakland, MD 21550
    /9

    $33,000

    $2K PRICE DROP
    • Land
    • 20,037 Sq Ft
    • $71,739 per Acre

    Lot 233 Cumberland Rd, Oakland, MD 21550

    This is the best priced lot at Deep Creek Lake! Seize the opportunity to own a beautiful parcel of land just minutes from Deep Creek Lake—one of the region’s most sought-after destinations for recreation and relaxation. This nearly half-acre property offers the rare combination of no HOA and no restrictions, giving you the freedom to bring your vision to life without limitations. Whether you're

    Sheila Howell Lake Homes Realty, LLC

    Lot 233 Cumberland Rd, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 4

Maryland Garrett County

Real Estate & Homes for Sale in Oakland, MD

Why Live in Oakland

Oakland, MD, located in the western part of the state, is known for its natural beauty and outdoor activities. The city is home to Deep Creek Lake, Maryland's largest freshwater lake, which offers nearly 70 miles of shoreline for boating, fishing, and swimming. Deep Creek Lake State Park provides public access with beaches, a boat launch, and extensive hiking and biking trails. Wisp Resort, the state's only ski resort, features 33 ski runs and year-round activities including hiking, disc golf, and golf courses. Oakland's downtown area showcases a variety of home styles, from vintage Victorians and Craftsmans to midcentury ranch-style houses. Lakefront properties often include A-frame cabins and Craftsman houses with private docks. Dining options in Oakland range from the casual Englanders diner, known for its buckwheat pancakes, to the upscale Stonecroft Manor steakhouse. Community events such as the Mountain Fresh Farmers Market and the Autumn Glory Festival foster a sense of local camaraderie. Students in Oakland attend Southern Garrett High School, which offers career and technical education programs. U.S. Route 219 runs through Oakland, connecting it to Interstate 68 and nearby cities like Cumberland, 50 miles away, and Morgantown, West Virginia, 55 miles away.

Learn more about living in Oakland

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $586,150.
How many homes have sold over the last 12 months in Oakland, MD?
143 homes have sold in Oakland, MD over the last 12 months.
What is the average household income in Oakland, MD?
The average household income in Oakland, MD is $73K.
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 $422,500. If you put a 20% down payment of $84,500 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $2,170 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $93K a year to afford the median home price in Oakland. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Oakland is $73K.
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 Prices in Oakland, MD

The median home sale price in Oakland, MD is $405,000, up 2% year-over-year. Homes in Oakland sell in 97 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
$276,000
Median 1 Bedroom Sale Price
$221,950
Average Price Per Sq Ft
$273
Number of Homes for Sale
64
Last 12 months Home Sales
143
Months of Supply
5.40
Median List Price
$422,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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