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Windham County VT Homes for Sale

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  • /2

    $1,400,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,844 Sq Ft

    286 Coldbrook Rd, Wilmington, VT 05363

    This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf

    Melissa Nebelski Real Broker LLC

    286 Coldbrook Rd, Wilmington, VT 05363
  • /20

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    1 Frog Hollow, Wilmington, VT 05363

    Charming Rustic Country Saltbox on Lower Chimney HillNestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful brick fireplace, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will love the easy access to snowmobile and hiking trails,

    Rich Caplan Deerfield Valley Real Estate

    1 Frog Hollow, Wilmington, VT 05363
  • /54

    $325,000

    • 5 Beds
    • 2 Baths
    • 1,944 Sq Ft

    2015 Vermont 30, Townshend, VT 05353

    Perfectly situated on the scenic road to Stratton Mountain—just 25 minutes from the slopes—this charming turn-of-the-century mixed-use property offers endless potential. Step inside to discover original period woodwork, gleaming hardwood floors, and classic details that give this roomy home its timeless character.The property also boasts a large two-story post-and-beam barn, lovingly restored

    Craig Ruggless EXP Realty

    2015 Vermont 30, Townshend, VT 05353
  • /12

    $125,000

    • Land
    • 15.6 Acres
    • $8,013 per Acre

    0 Thayer Rd, Westminster, VT 05158

    Rural 15.6 acre lot located at the end of Thayer Rd off Davidson Hill Rd in Westminster. This land is located in a quiet rural community on a gravel road about 10 minutes drive from Saxtons River Village and Bellows Falls Village. The lot consist of 3 lots of record all serviced by a common Right of Way. The ROW is also shared with a abutter to the north. The ROW provides ready to use access to

    Steve Schoppmeyer BHG Masiello Brattleboro

    0 Thayer Rd, Westminster, VT 05158
  • /38

    $475,000

    • Land
    • 133.1 Acres
    • $3,569 per Acre

    40 E Putney Brook Rd, Putney, VT 05346

    Awesome 133± Acre Country Parcel in Putney, Vermont. A rare opportunity to own 133± acres of picturesque Vermont land in highly desirable Putney. This large country parcel offers multiple access points, including generous frontage on a major road as well as two unpaved roads. Existing logging roads weave through the property, leading to several clearings ideal for building, recreation, or

    Geralyn Donohue Engel & Völkers Okemo

    40 E Putney Brook Rd, Putney, VT 05346
  • /23

    $685,000

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft

    457 Ray Hill Rd, Wilmington, VT 05363

    Lovely expanded farmhouse just up from the village of Wilmington and with mountain views and gorgeous exposure on 2.7 acres of private open land. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access despite it's private location. The home sits on a pastoral lot with gorgeous westerly views over Haystack Mountain for

    Adam Palmiter Berkley & Veller Greenwood/Dover

    457 Ray Hill Rd, Wilmington, VT 05363
  • /20

    $99,500

    • Land
    • 10.27 Acres
    • $9,688 per Acre

    0 Theresa Ln, Wilmington, VT 05363

    This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

    Lisa Mirando Deerfield Valley Real Estate

    0 Theresa Ln, Wilmington, VT 05363
  • /2

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft

    109 Central St, Brattleboro, VT 05301

    Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

    Christine Lewis Brattleboro Area Realty

    109 Central St, Brattleboro, VT 05301
  • /44

    $1,400,000

    • 5 Beds
    • 4 Baths
    • 4,099 Sq Ft

    314 Putnam State Forest Rd, Grafton, VT 05146

    Grafton Lodge is a striking five-bedroom, four-bathroom timber frame retreat set on 72 acres of complete privacy, directly bordering the 146-acre Putnam State Forest. Built in 2022, this 4,000+ sq ft home blends timeless craftsmanship with modern comforts, featuring wide hemlock floors, exposed beams, and walls of windows that invite the natural surroundings inside.At the heart of the home is

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    314 Putnam State Forest Rd, Grafton, VT 05146
  • /54

    $3,750,000

    • 6 Beds
    • 6.5 Baths
    • 5,660 Sq Ft

    168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360

    Experience true mountain luxury in this stunning six bedroom six bathroom slope side single family home, perfectly positioned for effortless access to world-class skiing and snowboarding at the Stratton Mountain Resort. Designed with comfort and style in mind, this residence combines refined alpine architecture with modern amenities including a gym, steam shower, pool table that doubles as table

    Timothy Mich Doddridge Stratton Real Estate

    168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360
  • /21

    $389,000

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    5E Polar Bear N, Dover, VT 05356

    Two-bedroom, one sleeping space loft, three-bath townhome in Bears Crossing, located minutes from Mount Snow. This unit includes access to a private Ski Home trail from the slopes and a seasonal shuttle to the mountain. The layout features a ground-level mudroom with bench seating and storage, two bedrooms—including a main-level bedroom with an en suite bath—and an additional full bath. The upper

    Erica Reynolds Southern Vermont Realty Group

    5E Polar Bear N, Dover, VT 05356
  • /44

    $425,000

    • 4 Beds
    • 3 Baths
    • 3,314 Sq Ft

    76 Spruce St, Brattleboro, VT 05301

    Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

    Christine Lewis Brattleboro Area Realty

    76 Spruce St, Brattleboro, VT 05301
  • /30

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,703 Sq Ft

    1089 Marlboro Rd, Brattleboro, VT 05301

    The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

    Christine Lewis Brattleboro Area Realty

    1089 Marlboro Rd, Brattleboro, VT 05301
  • /32

    $98,999 New Construction

    • 2 Beds
    • 2 Baths
    • 825 Sq Ft

    160 Shady Pines, Westminster, VT 05158

    Welcome to 160 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. (14 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    160 Shady Pines, Westminster, VT 05158
  • /16

    $235,000

    • Land
    • 33.48 Acres
    • $7,019 per Acre

    0 Vt Route 100 Unit 5072614, Londonderry, VT 05155

    Beautiful 33.48 acre building lot in Londonderry. Some views possible and some clearing has been done. There are some wetlands on property but various choices for building sites exist. South East Facing

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    0 Vt Route 100 Unit 5072614, Londonderry, VT 05155
  • /20

    $475,000

    • Land
    • 136.9 Acres
    • $3,470 per Acre

    0 Taft Rd Unit 5064573, Townshend, VT 05353

    In the late 1790's, General Samuel Fletcher gave a large parcel of land to young Benjamin Murdock, whose father had died from smallpox while serving in the Revolutionary War. Benjamin built a cabin and then a house, cleared and plowed the land, and with his wife raised 8 children. That land is now known as Murdock Mountain. Entering the property is like stepping into the past. The deep stone

    Bill Hickok Berkley & Veller Greenwood Country

    0 Taft Rd Unit 5064573, Townshend, VT 05353
  • /43

    $619,900

    • 3 Beds
    • 3.5 Baths
    • 2,250 Sq Ft

    883 Smead Rd, Wardsboro, VT 05355

    Enjoy Vermont living in this bright and inviting 3-bedroom, 4-bathroom home, ideally located 7 minutes from Mount Snow and just under 20 minutes from Stratton. The open-concept kitchen (completely renovated in 2021) and dining area are perfect for gatherings, with natural light enhancing the home’s warm and welcoming feel.A new heating system for efficient year-round comfort is complemented by a

    Samantha Decker Deerfield Valley Real Estate

    883 Smead Rd, Wardsboro, VT 05355
  • /48

    $1,550,000 Open Sat 3PM - 5PM

    • 4 Beds
    • 3.5 Baths
    • 3,666 Sq Ft

    3 Overbrook Dr Unit The Outlook at Mount, Dover, VT 05356

    STUNNING NEW CONSTRUCTION, SPECTACULAR VIEWS, GREAT LOCATION! Set against the backdrop of Mount Snow, this just completed luxury single-family home offers the perfect blend of modern design, spacious living.Located just minutes from the ski mountain, The Outlook at Mount Snow offers the perfect blend of mountain modern luxury and the ultimate convenience. This home features an open concept

    John Redd Skihome Realty

    3 Overbrook Dr Unit The Outlook at Mount, Dover, VT 05356
  • /60

    $798,000

    • 3 Beds
    • 3 Baths
    • 2,757 Sq Ft

    1909 Pine Banks Rd, Putney, VT 05346

    Sweetwood Farm circa 1894, this beautifully maintained extended Cape encompasses 60 serene acres of rolling meadows, shaded woodlands, and a peaceful, cascading brook. If you've been dreaming of a home that offers a convenient location, charm, and connection to the land, this is it. Inside, you'll find warm wide-pine floors, handcrafted cherry cabinets, and cozy living spaces filled with

    Heidi Bernier Berkley & Veller Greenwood Country

    1909 Pine Banks Rd, Putney, VT 05346
  • /27

    $33,000

    • 1 Bed
    • 2 Baths
    • 771 Sq Ft

    235/237, QTR 1 89 Grand Summit Way, Dover, VT 05356

    Own Where You Play! One-of-a-kind sleep eight quartershare, featuring a gas fireplace and gorgeous mountain views, this is a rare find in the Grand Summit Resort Hotel! This comfortable condo has two full baths and a lockout feature, with an adjoining door within the unit, so you can use it, rent it, or trade it for a timeshare vacation simultaneously! Overlooking the Grand Summit pool and the

    Patricia Fitzpatrick Skihome Realty

    235/237, QTR 1 89 Grand Summit Way, Dover, VT 05356
  • /42

    $447,000

    • 3 Beds
    • 3 Baths
    • 1,768 Sq Ft

    52A Suntec Loop, Dover, VT 05356

    New and improved Suntec units, with brand NEW building exterior, windows, doors! Welcome to this beautifully maintained, bright & spacious 3 bedroom, 3 bath, plus loft townhome, offering the perfect blend of space, comfort, and convenience just minutes from Mount Snow’s main base lodge, Carinthia Lodge, and the Hermitage Club. This home features three large bedrooms with high ceilings, a

    Prema Fitzpatrick Real Broker LLC

    52A Suntec Loop, Dover, VT 05356
  • /38

    $569,000

    • 4 Beds
    • 2.5 Baths
    • 2,062 Sq Ft

    96 Big Bend Loop, Wilmington, VT 05363

    Stunning updated contemporary chalet just a short drive out of the village of Wilmington with a tremendous rental history. This home sits privately on a wooded lot, nestled in the Chimney Hill community with easy access to the amenities building, as well as nearby access to Mount Snow and Lake Whitingham. The home has been fully renovated and features a gorgeous vaulted living room with exposed

    Adam Palmiter Berkley & Veller Greenwood/Dover

    96 Big Bend Loop, Wilmington, VT 05363
  • /41

    $725,000

    • 3 Beds
    • 3.5 Baths
    • 4,219 Sq Ft

    5 N Main St, Wilmington, VT 05363

    Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

    Morriah Adams BHG Masiello Brattleboro

    5 N Main St, Wilmington, VT 05363
  • /58

    $32,000

    • 1 Bed
    • 2 Baths
    • 771 Sq Ft

    123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356

    Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious mountain-side lockout unit, the closest unit to the back door to the slopes, comfortably sleeps 8. Unit 123 is a hotel room with 2

    Donna Brown Skihome Realty

    123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356
  • /25

    $349,000

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft

    337 Handle (Snow Tree Pines K) Rd Unit Pines K, Dover, VT 05356

    Welcome to this beautifully updated two bedroom, two-bathroom condo in the desirable upper Snow Tree community. The home is perfectly positioned to capture incredible mountain views and the true essence of Mount Snow base area living. Step inside to find a bright, inviting interior featuring new efficient windows, a cozy gas fireplace, and beautiful cathedral ceiling that enhances the spacious

    Melissa Ellis Southern Vermont Realty Group

    337 Handle (Snow Tree Pines K) Rd Unit Pines K, Dover, VT 05356
  • /29

    $25,000

    • Land
    • 0.6 Acre
    • $41,667 per Acre

    26 Upper Howes Way, Wilmington, VT 05363

    BUILD your dream home in this Lot in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse

    Sigrid Pickering Chimney Hill Realty

    26 Upper Howes Way, Wilmington, VT 05363
  • /24

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    115 Country Hill, Brattleboro, VT 05301

    This lovely West Brattleboro cape is located on a quiet cul-de-sac right on the outskirts of town. Built in 2002 with a spacious design, you enter through the oversized two-car garage into a contemporary kitchen. Features include granite countertops, tile floors, an elegant backsplash, and a door leading to a private terrace, ideal for family gatherings or entertaining. The first floor has

    Kristen Ziter Taylor Brattleboro Area Realty

    115 Country Hill, Brattleboro, VT 05301
  • /2

    $249,000

    • Land
    • 1.29 Acres
    • $193,023 per Acre

    350 Route 100, Dover, VT 05356

    Amazing opportunity to have a building lot near Mount Snow with huge view potential, no HOA restrictions, and easy access off a main paved road. This unique site is being offered for the first time in a long time and could be the ideal spot to build your dream Vermont home.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    350 Route 100, Dover, VT 05356
  • /60

    $1,350,000

    • 5 Beds
    • 3.5 Baths
    • 3,516 Sq Ft

    732 Under the Mountain Rd, South Londonderry, VT 05155

    Welcome to "Fairmount," a beautiful historic home with unrivaled panoramic views and an extraordinary blend of history, grace, and quintessential Vermont living on 42 acres. Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse seamlessly merges historic charm with modern sensibility. Exposed beams, wide plank floors, and architectural character remain, while the thoughtful

    Claudia Harris Mary Mitchell Miller Real Estate

    732 Under the Mountain Rd, South Londonderry, VT 05155
  • /28

    $195,000

    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft

    274/76Qtr.1-4 Grand Summit Way, Dover, VT 05356

    FULL ownership of this sleep 10 condo comprises of two units. Unit 276 has a private bedroom with a queen bed, queen sleeper sofa and queen murphy bed in the living area. Kitchenet and a full bath with an extra large covered balcony. Adjoining room 274 has 2 king beds and a full bath. Units are located on the base area side of the hotel. Wake up to the Grand Summit Express and the Bluebird lifts

    Kelly Agrillo Southern Vermont Realty Group

    274/76Qtr.1-4 Grand Summit Way, Dover, VT 05356
  • /11

    $75,000

    • Land
    • 1.8 Acres
    • $41,667 per Acre

    L40 Boardman Loop, Wardsboro, VT 05360

    Nestled in the desirable Snow Mountain Farms West community, this 1.8-acre wooded lot offers the perfect setting to build your Vermont dream home or getaway. Gently sloping and bordered by the serene Wardsboro Brook (outside the FEMA flood zone), the property combines natural beauty with practical readiness. A state-issued wastewater permit for a 3 bedroom single family home and an individual

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    L40 Boardman Loop, Wardsboro, VT 05360
  • /49

    $2,099,000

    • 5 Beds
    • 5.5 Baths
    • 5,235 Sq Ft

    6 Trail View Ln, Dover, VT 05356

    Enjoy stunning views, privacy, and luxury, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, tennis courts, game room, on site management company, and direct shuttle service between your

    Adam Palmiter Berkley & Veller Greenwood/Dover

    6 Trail View Ln, Dover, VT 05356
  • /39

    $25,000

    • Land
    • 0.5 Acre
    • $50,000 per Acre

    30 Upper Howes Way, Wilmington, VT 05363

    Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA.

    Sigrid Pickering Chimney Hill Realty

    30 Upper Howes Way, Wilmington, VT 05363
  • /35

    $749,000

    • 4 Beds
    • 5 Baths
    • 3,129 Sq Ft

    20 Ray Hill Rd, Wilmington, VT 05363

    Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen

    Adam Palmiter Berkley & Veller Greenwood/Dover

    20 Ray Hill Rd, Wilmington, VT 05363
  • /6

    $239,000

    • Land
    • 1.57 Acres
    • $152,229 per Acre

    2 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Find

    Andrew King Stratton Real Estate

    2 Gold Medal Cir, Stratton, VT 05343
  • /26

    $89,499 New Construction

    • 2 Beds
    • 1 Bath
    • 746 Sq Ft

    204 Shady Pines, Westminster, VT 05158

    Welcome to 204 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Polo model manufactured home offers 2 bedrooms, 1 bathroom, and 746 sq. ft. (14 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    204 Shady Pines, Westminster, VT 05158
  • /55

    $640,000

    • 3 Beds
    • 2.5 Baths
    • 1,808 Sq Ft

    15 Haymaker Ln Unit 6B, Wilmington, VT 05363

    A Wonderfully well built and maintained spacious Townhome in Desired Powderhorn Condo Association! Nestled in the heart of Vermont’s breathtaking Green Mountains, this beautifully maintained 3-bedroom, 2.5-bathroom condo is your dream getaway. Located just moments from mountain biking, skiing, snowmobiling including VAST trails. Two minutes from 2 world class golf courses and the stunning

    Steve Goldfarb Deerfield Valley Real Estate

    15 Haymaker Ln Unit 6B, Wilmington, VT 05363
  • /24

    $309,000

    • 3 Beds
    • 2 Baths
    • 1,388 Sq Ft

    96 Oak Hill Rd, Wardsboro, VT 05355

    Charming and woodsy chalet on a very private 1.2 acre parcel in the Snow Mountain Farms community, located conveniently between Mount Snow and Stratton Ski Resorts. This home is just down the street from the indoor pool and tennis court which afford nice amenities at a very reasonable cost. The lot has a sloping lawn up to the large entertaining deck. Inside you are treated to a large vaulted

    Adam Palmiter Berkley & Veller Greenwood/Dover

    96 Oak Hill Rd, Wardsboro, VT 05355
  • /5

    $270,000

    • 6 Beds
    • 2 Baths
    • 2,112 Sq Ft

    556 S Main St, Brattleboro, VT 05301

    What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit ofpressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

    Christine Lewis Brattleboro Area Realty

    556 S Main St, Brattleboro, VT 05301
  • /39

    $925,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    9D Dover Springs Ln, Dover, VT 05356

    Stunning updated Greenspring unit, just across the street from the Mount Snow ski resort with stunning direct views of the ski trails. This 4 bedroom, 4 bath unit features extensive upgrades, new furnishings, and immaculate condition, to ensure turn key enjoyment. Features include an open concept great room with vaulted ceiling and wood burning two sided fireplace, sunny exposure and sunset/ski

    Adam Palmiter Berkley & Veller Greenwood/Dover

    9D Dover Springs Ln, Dover, VT 05356

Showing Results 241 - 280, Page 7 of 10

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