Windham County VT Homes for Sale

• 

  

  

  /22

  $850,000

  • Land
  • 67 Acres
  • $12,687 per Acre

  00 S Pine Banks Rd, Putney, VT 05346

  Unleash the potential of this exceptional 60+ acre Vermont property, a rare offering brimming with diverse landscapes and endless possibilities. A well-maintained gravel driveway leads you into the heart of the land, complete with readily available power. Discover multiple potential building sites, each offering breathtaking views or secluded privacy, tailored to your preference. A charming

  

  Ross Doody

  Century 21 Highview Realty

  (802) 499-2391

  00 S Pine Banks Rd, Putney, VT 05346
• 

  

  

  /40

  $379,000

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

  254 Boynton Rd Unit 3, Londonderry, VT 05148

  Riverside Farm condominiums are uniquely designed and situated in a rural setting along a country road in Londonderry, VT, close to some of the area's best attractions. Quiet and serene with a view of the West River and surrounding countryside, these residences provide the Vermont lifestyle with the convenience of shared maintenance and amenities. This attractively renovated unit in the lower

  

  Beth Vickers

  Vermont Real Estate Company

  (802) 330-8072

  254 Boynton Rd Unit 3, Londonderry, VT 05148
• 

  

  

  /34

  $369,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  410 Tallwood Cir, Londonderry, VT 05148

  This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

  

  Alison Cummings

  Cummings & Co

  (802) 392-0721

  410 Tallwood Cir, Londonderry, VT 05148
• 

  

  

  /43

  $565,000

  • 4 Beds
  • 2.5 Baths
  • 2,149 Sq Ft

  66 Hilltop Rd, Londonderry, VT 05155

  This great home is a must see! Fully renovated in the past 8 months, from floor to ceilings, every inch has been updated. Brand new kitchen and baths, all new fixtures and appliances, this 4 bedroom 3 bath home is waiting for new owners to enjoy it! Great proximity to skiing, recreation, groceries and dining, yet private and set back from the road. Sold furnished with a pleasing neutral palate,

  

  Alison Cummings

  Cummings & Co

  (802) 553-3290

  66 Hilltop Rd, Londonderry, VT 05155
• 

  

  

  /18

  $120,000

  • Land
  • 2.84 Acres
  • $42,254 per Acre

  111 Gib Lockerby Rd, Grafton, VT 05146

  Nestled in the rolling hills of southern Vermont, just minutes above the charming center of Grafton, this professionally developed parcel of land beckons you to build your Vermont dream home. This open and sunny lot, complete with its own small apple orchard is surrounded by timeless stone walls and lovely woodlands. Choose the best building site for you; the cleared front acre, formerly a

  

  Christopher Cummings

  Cummings & Co

  (802) 424-8491

  111 Gib Lockerby Rd, Grafton, VT 05146
• 

  

  /35

  $2,399,000

  • 4 Beds
  • 4.5 Baths
  • 3,569 Sq Ft

  662 Howe Farm Rd, Jamaica, VT 05343

  Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  662 Howe Farm Rd, Jamaica, VT 05343
• 

  

  /79

  $275,000

  • Land
  • 22.32 Acres
  • $12,321 per Acre

  81 Parish Hill Rd Unit 26, Newfane, VT 05345

  Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

  Chad Bruyette Whitetail Properties Real Estate

  81 Parish Hill Rd Unit 26, Newfane, VT 05345
• 

  

  /12

  $999,000

  • Land
  • 12.2 Acres
  • $81,885 per Acre

  Higley Hill Rd, Wilmington, VT 05363

  Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

  Community Lands Community Lands

  Higley Hill Rd, Wilmington, VT 05363
• 

  

  /36

  $210,000

  • Land
  • 30.1 Acres
  • $6,977 per Acre

  184 Schoolhouse Rd, Jamaica, VT 05343

  Jamaica, Vermont's hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

  Curtis Trousdale

  184 Schoolhouse Rd, Jamaica, VT 05343
• 

  

  /8

  $275,000

  • Land
  • 34.53 Acres
  • $7,964 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  /11

  $495,000

  • Land
  • 68.89 Acres
  • $7,185 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  /7

  $195,000

  • Land
  • 15.27 Acres
  • $12,770 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  /15

  $650,000

  • Land
  • 51.93 Acres
  • $12,517 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  /28

  $799,000

  • 5 Beds
  • 3.5 Baths
  • 5,187 Sq Ft

  14 Stone Ridge Loop, Dover, VT 05356

  Beautiful architect designed home in the prestigious Village at Sawmill Farms, just a short drive from the Mount Snow ski resort. This Rod Williams contemporary farmhouse design is incredibly functional and unique, and has been completely renovated to be turn key for immediate enjoyment. The interior boasts a large great room with soaring windows, great natural light, and a wood burning

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14 Stone Ridge Loop, Dover, VT 05356
• 

  

  /42

  $574,900

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  Welcome to your dream home in the heart of Southern Vermont. This brand-new construction 3-bedroom, 2-bath residence seamlessly blends modern comfort with classic Vermont charm, perfect for year-round living or a weekend escape. Enjoy a spacious, open-concept layout filled with natural light, enhanced by high-quality Anderson windows and doors. The kitchen boasts brand new appliances, while the

  Flex Realty Group Flex Realty

  555 Vermont 9, Wilmington, VT 05363
• 

  

  /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
• 

  

  /41

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,091 Sq Ft

  798 Vermont Route 100, Wilmington, VT 05363

  Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  798 Vermont Route 100, Wilmington, VT 05363
• 

  

  /39

  $312,000

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  15 Mountain Village Unit 234, West Dover, VT 05356

  Welcome to your mountain getaway! This 2-bedroom, 2-bath condo is perfectly situated at the base of Mount Snow. Enjoy your morning coffee or après-ski beverage on the private balcony while taking in the mountain air and breath taking views. Cozy up by the wood-burning fireplace, perfect for relaxing after a day on the mountain. Recent updates include new windows, slider doors, balcony, flooring

  Jillian Wimmelman Deerfield Valley Real Estate

  15 Mountain Village Unit 234, West Dover, VT 05356
• 

  

  /31

  $735,000

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

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

  Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

  Timothy Mich Doddridge Stratton Real Estate

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
• 

  

  /42

  $798,000

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

  Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  619 Stratton Arlington Rd, West Wardsboro, VT 05360
• 

  

  /44

  $599,000

  • 4 Beds
  • 4 Baths
  • 4,060 Sq Ft

  141 Piney Brook Way, Brattleboro, VT 05301

  Set on 12 acres of wooded privacy in desirable Marlboro, this spacious and versatile property offers comfort, flexibility, and stunning natural surroundings. The main home features 3 bedrooms, a large family room and first-floor laundry, offering plenty of room for a growing household, guests, or multi-generational living. Cozy up by the wood stove on chilly evenings, and enjoy the peace of mind

  Desiree Stango Berkley & Veller Greenwood Country

  141 Piney Brook Way, Brattleboro, VT 05301
• 

  

  /40

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  4448 Route 100, Wardsboro, VT 05355

  This four-bedroom, three-bathroom home with office, family room with woodburning fireplace, den, formal dining room with large eat in kitchen with tile flooring is set back off the main road. Private pond with a large sprawling yard. The two car attached garage with access to basement and storage space above is very convenient for winter! Cedar exterior with a Brazilian rosewood oil finish,

  Julie Lowe Lowe's Real Estate, LLC

  4448 Route 100, Wardsboro, VT 05355
• 

  

  /51

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
• 

  

  /35

  $579,000

  • 4 Beds
  • 1 Bath
  • 1,560 Sq Ft

  104 Karen Day Rd, Halifax, VT 05342

  1860's Colonial/Farmhouse situated on nearly 37 acres of gorgeous land. This location, exposure, access and overall site characteristics is truly one of a kind. Ultimate privacy due to the town-maintained road (Karen Day Road) running from Larrabee Road all the way to the house and compound with no other houses along the road or in sight whatsoever. The land is remarkable with level open fields,

  Chris Long BHG Masiello Brattleboro

  104 Karen Day Rd, Halifax, VT 05342
• 

  

  /45

  $644,000

  • 3 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  774 Stratton Arlington Rd, Stratton, VT 05360

  Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  774 Stratton Arlington Rd, Stratton, VT 05360
• 

  

  /60

  $645,000

  • 3 Beds
  • 3.5 Baths
  • 2,472 Sq Ft

  38 Greenspring Rd, Dover, VT 05356

  Welcome to Greensprings one of Mount Snow’s most sought-after communities offering the perfect blend of mountain convenience and Vermont charm. This spacious 3 bedroom, 4 bath townhome features stunning mountain views and an inviting open-concept living area with vaulted wood ceilings, a dramatic wall of windows, and a floor-to-ceiling wood-burning fireplace.The main level is ideal for

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  38 Greenspring Rd, Dover, VT 05356
• 

  

  /38

  $639,000

  • 3 Beds
  • 2.5 Baths
  • 3,113 Sq Ft

  1382 Grassy Brook Rd, Brookline, VT 05345

  Beautiful Brookline! Lovingly developed by the current owners over the past 40 years, this remarkable property offers a rare opportunity—ideal for a builder, contractor, skier, snowmobiler, or anyone seeking space for equipment storage. Arrive by crossing a charming stream and following a gentle rise to the main home, which includes a one-car attached garage in the basement. Inside, the finished

  Thomas Dahlin Berkley & Veller Greenwood Country

  1382 Grassy Brook Rd, Brookline, VT 05345
• 

  

  /29

  $649,000

  • 5 Beds
  • 3.5 Baths
  • 2,706 Sq Ft

  916 Wiswall Hill Rd, Townshend, VT 05353

  Escape to the peace and beauty of Townshend, Vermont, where this spacious 5-bedroom home offers the perfect blend of privacy, comfort, and craftsmanship. Located on a publicly maintained dead-end road, the property enjoys a quiet, secluded country setting while still providing the reassurance of year-round access. Thoughtfully designed and well-built, the home welcomes you with warmth and

  Mike Masters Four Seasons Sotheby's Int'l Realty

  916 Wiswall Hill Rd, Townshend, VT 05353
• 

  

  /32

  $560,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  162 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /34

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  24 Dogwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  24 Dogwood Dr, Brattleboro, VT 05301
• 

  

  /32

  $675,000

  • 3 Beds
  • 3 Baths
  • 2,216 Sq Ft

  12 Three Streams Way, Wilmington, VT 05363

  Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  12 Three Streams Way, Wilmington, VT 05363
• 

  

  /32

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  161 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  161 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /39

  $625,000

  • 5 Beds
  • 4 Baths
  • 3,748 Sq Ft

  58 Oak St, Brattleboro, VT 05301

  Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

  Rebecca Seymour Brattleboro Area Realty

  58 Oak St, Brattleboro, VT 05301
• 

  

  /60

  $579,000

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft

  794 White Rd, Windham, VT 05359

  Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

  Erica Reynolds Southern Vermont Realty Group

  794 White Rd, Windham, VT 05359
• 

  

  /43

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,720 Sq Ft

  58 Buckboard Dr, Dover, VT 05356

  58 Buckboard | Dover, VermontSet on 1.46 private acres with sweeping mountain views, this beautifully updated 3 bedroom, 3 bath home offers a perfect blend of modern style and Vermont warmth.Inside, the heart of the home is the newly renovated kitchen, featuring a center island with quartz countertops, stainless steel appliances, and open shelving. The kitchen flows seamlessly into the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  58 Buckboard Dr, Dover, VT 05356
• 

  

  /26

  $649,000

  • 3 Beds
  • 3 Baths
  • 2,170 Sq Ft

  14 Johnson Hill Rd, Dover, VT 05356

  Unique contemporary chalet just a short drive from the Mount Snow Ski Resort and village Wilmington, and with direct snowmobile trail access. This very cool open concept home has been completely renovated and upgraded, and sits on a on a private lot in the Dover Hills with beautiful lawn space and cul de sac driveway. Walk in through the spacious mudroom with plenty of room for gear, and head up

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14 Johnson Hill Rd, Dover, VT 05356
• 

  

  /49

  $695,000

  • 4 Beds
  • 2.5 Baths
  • 3,104 Sq Ft

  153 Westminster Rd, Putney, VT 05346

  Combining the charm of an 1820's fully restored historic home, with a 1,600 sq. ft. addition (built in 2016), this fabulous property, close to the Putney Village, offers the best of both worlds. Wide pine flooring and exposed beams in the restored front half blend beautifully with the newly built addition, featuring 9’ ceilings, hardwood floors and a handsome stone fireplace. The expansive

  Heidi Bernier Berkley & Veller Greenwood Country

  153 Westminster Rd, Putney, VT 05346
• 

  

  /59

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,782 Sq Ft

  628 Townshend Rd, Grafton, VT 05146

  One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

  Jessica Landers Barrett and Valley Associates Inc.

  628 Townshend Rd, Grafton, VT 05146
• 

  

  /25

  $239,000

  • 4 Beds
  • 1.5 Baths
  • 1,690 Sq Ft

  7511 Westminster West Rd, Putney, VT 05346

  This property has so much potential! Located just 3 minutes from the village of Saxtons River home to the Vermont Academy School this property finds itself nestled in the countryside. The Home has some great features like a finished basement, a screened in porch plus a large deck, a primary bedroom with a bathroom and so much more! There is some TLC needed but the potential is endless. The

  Thaddeus Abare Barrett and Valley Associates Inc.

  7511 Westminster West Rd, Putney, VT 05346
• 

  

  /57

  $1,345,000

  • 3 Beds
  • 2 Baths
  • 2,546 Sq Ft

  135 Fred Houghton Rd, Putney, VT 05346

  This one-of-a-kind Vermont property offers three dwellings on 5.6 acres - each blending elevated aesthetics, thoughtful design, and a true connection to nature. The 2011 main house features an open layout and handcrafted finishes throughout. The kitchen boasts soapstone countertops and custom cherry cabinetry. A very special wood-fired masonry heater anchors the living space and a spacious

  Benjamin Cote EXP Realty

  135 Fred Houghton Rd, Putney, VT 05346

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