87

Oakland, MD Homes for Sale with Acreage

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  • /64

    $1,249,000

    • 4 Beds
    • 3.5 Baths
    • 3,071 Sq Ft

    590 S Blakeslee Rd, Oakland, MD 21550

    Nestled in the much sought after Blakeslee community you will find this lovely mountain retreat with lake access and exceptional amenities. This contemporary-style home is designed for both relaxation and entertainment, featuring a spacious open-concept layout, multiple family rooms, a large loft, and a well-appointed kitchen. Offering three levels of living space, hardwood flooring, quartz

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    590 S Blakeslee Rd, Oakland, MD 21550
  • /39

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft

    501 Christophers Way, Oakland, MD 21550

    Check out this opportunity to own your own mountain top chalet getaway complete with 3 bedrooms and 2 bathrooms and situated on 3 acres. A peaceful setting amongst mature trees and abundant wildlife with views of the surrounding mountains. Backbone Ridge community borders the highest point in Maryland and is conveniently located to several ski resorts, state parks, national forest & entertainment

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    501 Christophers Way, Oakland, MD 21550
  • /18

    $248,900

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft

    2571 Shady Dell Rd, Oakland, MD 21550

    They call it Pleasant Valley for a reason! The property features a 2+ acre wooded area, a serene stream, several berry plants, 2 sheds, chicken coop, and a rear deck. Front porch and a fenced-in front yard. Inside, there is a large, bright living room, an updated kitchen with plenty of cabinet space, appliances, and sliding glass doors leading to the deck. The bathrooms have been updated. Full

    Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
  • /10

    $175,000

    • Land
    • 3.04 Acres
    • $57,566 per Acre

    132 &132A Tarn Dr, Oakland, MD 21550

    3+ Acre Lake Access Homesite in Mountainside CommunityLots 132 & 132A offer a rare opportunity to own 3.04 acres of lake access property in the highly desirable Mountainside Community. Located at the end of a quiet cul-de-sac on Tarn Drive, these combined lots are officially recorded as one building site—providing ultimate privacy and a perfect setting to build your dream home. Public water &

    Rich Orr Railey Realty, Inc.

    132 &132A Tarn Dr, Oakland, MD 21550
  • /31

    $165,000

    • Land
    • 13 Acres
    • $12,741 per Acre

    0 Mayhew Inn Rd Unit MDGA2009662, Oakland, MD 21550

    Almost 13 acres of beautiful land in the Deep Creek Lake area. Build your dream home or vacation rental masterpiece! 2 lots featuring beautiful mature trees, a clearing to build on, and just minutes to all of Deep Creek Lake's recreation, shopping, restaurants, and amenities.

    Justin Liller Railey Realty, Inc.

    0 Mayhew Inn Rd Unit MDGA2009662, Oakland, MD 21550
  • /46

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    1737 King Wildesen Rd, Oakland, MD 21550

    Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland.This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP)

    Justin Liller Railey Realty, Inc.

    1737 King Wildesen Rd, Oakland, MD 21550
  • /29

    $239,000

    • 1 Bed
    • 1 Bath

    206 Mayhew Inn Rd, Oakland, MD 21550

    Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate

    Jay Quinn Taylor Made Deep Creek Vacations & Sales

    206 Mayhew Inn Rd, Oakland, MD 21550
  • /49

    $345,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    254 Little Mountain Rd, Oakland, MD 21550

    Welcome to 254 Little Mountain Road, a serene mountain escape nestled on nearly 5 acres in the Backbone Ridge community. The community borders the highest point in MD. This beautifully maintained 4-bed, 2-bath home is surrounded by natural beauty. Spacious and inviting layout featuring exposed beams, and a wood-burning fireplace that creates the perfect atmosphere for mountain living.

    Amy Skipper Railey Realty, Inc.

    254 Little Mountain Rd, Oakland, MD 21550
  • /42

    $185,000

    • Land
    • 21 Acres
    • $8,621 per Acre

    0 Sanders Ln Unit MDGA2009314, Oakland, MD 21550

    Tucked along scenic Sanders Lane just 4 miles from Oakland, MD, this picturesque 21.46-acre pastoral lot offers the perfect blend of open space, gentle rolling fields, and peaceful countryside charm. Surrounded by open spaces, in a sought-after neighborhood, this property is ideal for building your dream estate, hobby farm, or private retreat. Enjoy wide-open skies, room to roam, and the serenity

    Susan Bell Railey Realty, Inc.

    0 Sanders Ln Unit MDGA2009314, Oakland, MD 21550
  • /86

    $1,199,999

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft

    216 Tarn Dr, Oakland, MD 21550

    Breathtaking turn-key home located in the well-established Mountainside community. This newer home is simply stunning from the moment you enter. The cathedral ceilings, granite countertops, luxury vinyl flooring, sunroom with hot tub, and bonus room above the garage checks off all the boxes. The attention to detail is felt throughout this home, from the first level laundry room to the office/den,

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    216 Tarn Dr, Oakland, MD 21550
  • /3

    $279,900

    • Land
    • 18 Acres
    • $15,550 per Acre

    0 Bear Run Rd, Oakland, MD 21550

    UNRESTRICTED RAW LAND, DIRECTLY BORDERS STATE LAND (OVER 2000 ACS - MD DEPT OF NATURAL RESOURCES), FULLY WOODED & MARKETABLE TIMBER (RECENT TIMBER EVALUATED BETWEEN $100K-120K IN 2024), TROPHY BUCK HUNTING (INCLUDES CUSTOM BUILT HUNTING BLIND), SHORT DRIVE TO DEEP CREEK LAKE, STONES THROW TO YOUGHIOGHENY RIVER, OVERLOOKS DEEP CREEK LAKE VALLEY.

    Mike Haywood The Mike Haywood Group

    0 Bear Run Rd, Oakland, MD 21550
  • /5

    $79,000

    • Land
    • 9 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
  • /4

    $51,000

    • Land
    • 7 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
  • /58

    $439,900

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    3930 Mayhew Inn Rd, Oakland, MD 21550

    2 for 1 on 3.43 acres! Remodeled 2BR 2BA cottage with auxiliary building that has an oversized garage, multiple workshop areas and 1BR 1BA apartment on the second level. Cabin boasts high end finishes and open living space with a cozy wood burning stove. Recent upgrades include: heat pump + AC, appliances, modern kitchen, granite tops, bathrooms, some window & doors, as well as spacious decking.

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • /12

    $55,000

    • Land
    • 1.58 Acres
    • $34,810 per Acre

    0 Oakland Sang Run Rd Unit MDGA2009116, Oakland, MD 21550

    Rare opportunity! Impressive views of the Oakland golf course, pond and scenic vista! 5 lots in Country Club Acres Section 2, lots 66, 67, 68, 69 and 70, totaling 1.58+/- acres of land, all fronting on hole #13. Private driveway access already in place off Oakland Sang Run Rd. Public sewer nearby via Crosby Drive. Well water. One home can be built in total and there is flexibility on where you

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Oakland Sang Run Rd Unit MDGA2009116, Oakland, MD 21550
  • /29

    $219,900

    • Land
    • 1.10 Acres
    • $199,909 per Acre

    47 Ridgewood Dr, Oakland, MD 21550

    Prime Lake Access Lot in Mountainside – Perfect for Your Dream Home! Nestled on a one-acre wooded lot in the sought-after Mountainside community, this homesite offers breathtaking views of Deep Creek Lake and the ideal slope for a walk-out basement. Enjoy the best of four-season living with easy access to community lake privileges, state parks, restaurants, and WISP Resort. Plus, take advantage

    Michael Fenton Railey Realty, Inc.

    47 Ridgewood Dr, Oakland, MD 21550
  • /3

    $249,900

    • Land
    • 24 Acres
    • $10,412 per Acre

    0 Bear Run Rd, Oakland, MD 21550

    UNRESTRICTED RAW LAND, DIRECTLY BORDERS STATE LAND (OVER 2000 ACS - MD DEPT OF NATURAL RESOURCES), FULLY WOODED & MARKETABLE TIMBER (RECENT TIMBER EVALUATED BETWEEN $100K-120K IN 2024), TROPHY BUCK HUNTING (INCLUDES CUSTOM BUILT HUNTING BLIND), SHORT DRIVE TO DEEP CREEK LAKE, STONES THROW TO YOUGHIOGHENY RIVER, OVERLOOKS DEEP CREEK LAKE VALLEY.

    Mike Haywood The Mike Haywood Group

    0 Bear Run Rd, Oakland, MD 21550
  • /73

    $899,000

    • 5 Beds
    • 4.5 Baths
    • 2,846 Sq Ft

    139 Overlook Ridge Dr, Oakland, MD 21550

    Perched atop Holiday Hill on a 1.5-acre site, you will find this contemporary home with beautiful views of Deep Creek Lake! Offering over 3,200 SF with an open floorplan and an abundance of windows, making this home feel warm and inviting while offering plenty of room to enjoy family and friends. Boasting four bedrooms, 3.5 baths, three levels of living space, hardwood flooring, two stone propane

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    139 Overlook Ridge Dr, Oakland, MD 21550
  • /57

    $1,199,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log home located in the centrally located Paradise Cove community. This home offers three levels of living space, an open floorplan and three bedrooms. Recent upgrades in the past five years which include renovated kitchen, granite countertops, upgraded baths and floors, new wrap around deck, some new windows, new appliances, new roof, and new garage doors and

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    127 Paradise Heights, Oakland, MD 21550
  • /10

    $325,000

    • Land
    • 2.07 Acres
    • $157,005 per Acre

    Lot G Randall Way, Oakland, MD 21550

    Pergin Farm lake access lot with 2 acres and one boat slip. A private wooded setting in one of Deep Creeks most desirable, warm, and inviting locations.

    Russell Bounds Railey Realty, Inc.

    Lot G Randall Way, Oakland, MD 21550
  • /21

    $165,000

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft

    607 K St, Oakland, MD 21550

    Estate sale. 4 bedroom, 2 bath home on 8 Town lots, totaling 1.1+ acres in Mountain Lake Park. Its possible to subdivide several lots off to re-sell. Partially remodeled, updated bathroom with custom tile, potential for multiple heat sources. Disconnected wood stove. House set up for one level living. One block from Veterans Park & pickleball courts, close to schools & Broadford Park. Sold AS IS.

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    607 K St, Oakland, MD 21550
  • /6

    $129,000

    • Land
    • 3.05 Acres
    • $42,295 per Acre

    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 28 located in a subdivision called the view, it lives up to the name and offers 3.05 Acres. Prime location for a vacation rental, second home, or primary residence with filtered lake and mountain views. Northwestern orientation offers a chance for beautiful sunset views. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 28 Briarwood Ln Unit MDGA2008896, Oakland, MD 21550
  • /6

    $129,000

    • Land
    • 3.10 Acres
    • $41,613 per Acre

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 29 is located in a subdivision called the View, and it lives up to the name! Offering a generous 3.10 Acres with possible lake views this attractive location is close to lake amenities while giving a sense of privacy. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
  • /15

    $42,000

    • Land
    • 3.03 Acres
    • $13,861 per Acre

    Lot 1 Cherrywood Dr, Oakland, MD 21550

    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. Underground electric in place

    Amy Skipper Railey Realty, Inc.

    Lot 1 Cherrywood Dr, Oakland, MD 21550
  • /6

    $184,000

    • Land
    • 48 Acres
    • $3,833 per Acre

    0 Garrett Rd Unit MDGA2008796, Oakland, MD 21550

    Located just a short distance from Oakland and Deer Park, this 48 +/- acre parcel offers a beautiful mix of open pasture and wooded land. A small brook winds through part of the property, and you’ll find some cherry timber scattered throughout. The second pasture boasts sweeping views, perfect for soaking in the surrounding countryside. With easy access off Garrett Road, this land offers a

    Nicole Jackson Railey Realty, Inc.

    0 Garrett Rd Unit MDGA2008796, Oakland, MD 21550
  • /20

    $57,900

    • Land
    • 1.00 Acre
    • $57,900 per Acre

    111 Tarn Dr, Oakland, MD 21550

    Can't find the home you're looking for? Buy land and build it your way at Deep Creek Lake! This 1 acre parcel is in the lake access community Mountainside and is centrally located to Wisp Resort, State Parks and local Restaurants. Community offers Marina Club, tennis, hiking and biking. Great vacation rental potential. Public water and sewer hook-ups are available. Enjoy what Deep Creek Lake has

    Amy Grubby AEK Real Estate, LLC

    111 Tarn Dr, Oakland, MD 21550
  • /33

    $200,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is located on the southwest corner of Maryland Highway, State Route 135 and Main Street, Deer Park. It is 2.5 acres, more or less, which is part of Parcel 0069 Map 0073, containing 32.20 acres, more or less. The remaining 30.00 acres on the northwest side of Route 135 is not included. The 2.5 acres is an estimate of area and is subject to a survey for

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • /25

    $980,000

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

    340 Grandview Dr, Oakland, MD 21550

    Major renovations on the interior have been completed. The roof, deck staining will be complete in two weeks. This home has been inspected and items addressed. Summer rentals are booking fastDramatic Price Reduction – Motivated Seller – Turnkey Vacation Rental with the most incredible views of Cherry Creek CoveDon’t miss this incredible opportunity to own a fully-furnished home in the desirable

    Michael Cumerlato Jason Mitchell Group

    340 Grandview Dr, 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
  • /137

    $1,950,000

    • 4 Beds
    • 3.5 Baths
    • 5,576 Sq Ft

    2829 Shady Dell Rd, Oakland, MD 21550

    Experience your own slice of paradise in the highly desirable Pleasant Valley area of Garrett County. This scenic 3-bedroom log home overlooks a serene private pond, nestled on 22 breathtaking acres that blend open pasture with peaceful wooded areas, all with stunning mountain views. The property boasts a 2-car detached garage and an impressive, upscale barn with a spacious workshop, offering

    Jon Bell Railey Realty, Inc.

    2829 Shady Dell Rd, Oakland, MD 21550
  • /15

    $175,000

    • Land
    • 1.60 Acres
    • $109,375 per Acre

    1 Lowes Dr, Oakland, MD 21550

    Lot #1. is 1.6 Acre Cleared Commercial Site in Lowe's Subdivision. Public Utilities and Natural gas to the site. Paved street access and High Traffic Zone. Plat available.

    Rich Orr Railey Realty, Inc.

    1 Lowes Dr, Oakland, MD 21550
  • /5

    $67,500

    • Land
    • 1.02 Acres
    • $66,176 per Acre

    Lot 20 Maple Del Ln, Oakland, MD 21550

    Land Listing: Prime 1-Acre Lot Near Deep Creek LakeDiscover the perfect opportunity to build your dream retreat in the desirable Maple Del community.This 1-acre lot is ideally situated across the street from the stunning Deep Creek Lake, offering convenient access to outdoor activities and beautiful views.Property Features:• Location: Maple Del Community, across from Deep Creek

    Michael Cumerlato Jason Mitchell Group

    Lot 20 Maple Del Ln, Oakland, MD 21550
  • /108

    $2,750,000

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built timber frame home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. The log home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled

    Shelia McCracken Taylor Made Deep Creek Vacations & Sales

    2725 Stockslager Rd, Oakland, MD 21550
  • /26

    $699,000

    • Land
    • 34 Acres
    • $20,601 per Acre

    0 Memorial Dr Unit MDGA2007836, 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 MDGA2007836, Oakland, MD 21550
  • /3

    $170,000

    • Land
    • 1.00 Acre
    • $170,000 per Acre

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550

    Centrally located 1-acre lake access homesite with a dock slip! This property has endless possibilities to build, and depending on where you decide to position your new home, there could be potential for lake views. Offering public sewer and no HOA fees. The only decision left to be made is what style home you will build. Just minutes to the DCL State Park, several restaurants, convenience store,

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
  • /32

    $30,000

    • Land
    • 2.10 Acres
    • $14,286 per Acre

    14 Yough View Dr, Oakland, MD 21550

    Motivated Seller. Bring an offer!!!!! Build your dream home fronting on the Youghiogheny River!!! This 2 acre lot fronts to the community access area, so you are an easy walk to the river's edge. Perc approved for a 3 bedroom home. The Timbers on the Yough gated community features access to the river as well as hiking trails. Close to the town of Oakland, local parks, and unlimited outdoor

    Rachel Bruch Railey Realty, Inc.

    14 Yough View Dr, Oakland, MD 21550
  • /22

    $115,000

    • Land
    • 2.86 Acres
    • $40,210 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
  • /13

    $29,900

    • Land
    • 1.18 Acres
    • $25,339 per Acre

    Lot 15 Overlook Dr, Oakland, MD 21550

    Affordable lake access building lot! Approved perc for a 4 bedroom dwelling, walkable access to Deep Creek Lake, and located in a gorgeous setting surrounded by beautiful homes and landscape. No short term vacation rentals in this community. Close to all area amenities such as Wisp Resort, Swallow Falls, Deep Creek Lake State Park, & more!

    Nina Beitzel Railey Realty, Inc.

    Lot 15 Overlook Dr, Oakland, MD 21550
  • /38

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft

    637 Betts Ln, Oakland, MD 21550

    Are you looking for a private setting on over 7 acres of land? You will love this quiet, peaceful location while still being close to Deep Creek Lake and Oakland Maryland. This home features 3 bedrooms, 2 baths, a nice sized basement ready for your finishing touches, and a large attached 2 car garage! Enjoy relaxing moments on the covered front porch or watching for wildlife on the back deck!

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    637 Betts Ln, Oakland, MD 21550
  • /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA133598, 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 MDGA133598, Oakland, MD 21550

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