Windham County VT Homes for Sale

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  /14

  $120,000

  • Land
  • 2.07 Acres
  • $57,971 per Acre

  191 Pingree Park Ln, Londonderry, VT 05148

  Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

  

  Alison Cummings

  Cummings & Co

  (802) 848-6904

  191 Pingree Park Ln, Londonderry, VT 05148
• 

  

  

  /18

  $130,000

  • Land
  • 2.19 Acres
  • $59,361 per Acre

  192 Pingree Park Ln, Londonderry, VT 05148

  Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

  

  Alison Cummings

  Cummings & Co

  (802) 444-8158

  192 Pingree Park Ln, Londonderry, VT 05148
• 

  

  

  /16

  $235,000

  • Land
  • 4.26 Acres
  • $55,164 per Acre

  190 &192 Pingree Park Ln, Londonderry, VT 05148

  Quiet and pristine, this 4 + acre parcel is a prime location for your new home. At the end of a private road and within an easy distance to the grocery store, this is truly the best of both worlds. With babbling Utley Brook as the boundary on the East side, across the river is protected by a conservation district, insuring riverfront privacy. This nicely wooded parcel already has a road into the

  

  Alison Cummings

  Cummings & Co

  (802) 523-3683

  190 &192 Pingree Park Ln, Londonderry, VT 05148
• 

  

  

  /22

  $1,000,000

  • Land
  • 67 Acres
  • $14,925 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
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  /30

  $125,000

  • 1,968 Sq Ft

  10 Taylor St, Town of Rockingham, VT 05101

  INVESTER SPECIAL! This 2-unit property has separate utilities, 2-3 bedroom units on each floor depending on how the layout is set up. Rooms are generously sized, front and side porches for each unit, full basement and attic.This would make a nice generational or family home or a great starter home with rental potential.

  

  Julie Buffum

  Buffum Realty

  (802) 347-9139

  10 Taylor St, Town of Rockingham, VT 05101
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  /56

  $350,000

  • 6 Beds
  • 4.5 Baths
  • 3,042 Sq Ft

  2072 N Main St, Londonderry, VT 05148

  Rare Mixed-Use Opportunity in Downtown Londonderry, VT – Live, Work, or Invest! Unlock the full potential of this versatile and beautifully situated property in the heart of Londonderry’s vibrant downtown district. With major West River frontage, expansive lawn space, and prime visibility on North Main Street, this unique listing offers endless possibilities — perfect for residential, commercial,

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 441-6058

  2072 N Main St, Londonderry, VT 05148
• 

  

  /10

  $185,000

  • Land
  • 8 Acres
  • $23,125 per Acre

  4441 Vt Route 30, Jamaica, VT 05343

  Discover the potential of this serene and wooded 8.0± acre parcel, offering a peaceful setting and natural beauty just minutes from the heart of Jamaica Village. Currently being subdivided from a larger tract, the lot features a 5 Bedroom Wastewater Permit pending state approval and a survey in progress to finalize boundaries—laying the foundation for your future plans. An existing electric

  

  Trent Stephens

  Wohler Realty Group

  (802) 808-6056

  4441 Vt Route 30, Jamaica, VT 05343
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  /41

  $8,950,000

  • 6 Beds
  • 10 Baths
  • 13,393 Sq Ft

  370 Fischer Ln, Jamaica, VT 05343

  Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

  Dia Jenks LandVest, Inc/Woodstock

  370 Fischer Ln, Jamaica, VT 05343
• 

  

  /60

  $599,000

  • 3 Beds
  • 2 Baths
  • 3,000 Sq Ft

  121 Dover Hill Rd, Dover, VT 05341

  Highly motivated sellers. Ideal for remote workers or second-home buyers, this Vermont retreat offers fiber-optic internet, energy-efficient systems, no water or sewer bills, and some of the state's lowest property taxes. Set on 5 private acres just minutes from Mount Snow and Grout Pond, this move-in ready home supports low-cost living with high quality of life.The updated kitchen

  Nick Sicard EXP Realty

  121 Dover Hill Rd, Dover, VT 05341
• 

  

  /15

  $775,000

  • Land
  • 51.93 Acres
  • $14,924 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

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /11

  $595,000

  • Land
  • 68.89 Acres
  • $8,637 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

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  /8

  $320,000

  • Land
  • 34.53 Acres
  • $9,267 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

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /7

  $235,000

  • Land
  • 15.27 Acres
  • $15,390 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
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  /47

  $550,000

  • 4 Beds
  • 4 Baths
  • 2,372 Sq Ft

  187 Hillwinds Rd, Brattleboro, VT 05301

  Welcome home! Four bedroom, 4-bathroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A

  Claire Renaud Berkley & Veller Greenwood Country

  187 Hillwinds Rd, Brattleboro, VT 05301
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  /3

  $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
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  /3

  $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
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  /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
• 

  

  /35

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,044 Sq Ft

  11 Dutchman Ln Unit 4A, Wilmington, VT 05363

  This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  11 Dutchman Ln Unit 4A, Wilmington, VT 05363
• 

  

  /3

  $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
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  /60

  $599,000

  • 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 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 board, and

  Erica Reynolds Southern Vermont Realty Group

  794 White Rd, Windham, VT 05359
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  /43

  $615,000

  • 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
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  /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
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  /49

  $725,000

  • 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
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  /60

  $625,000

  • 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
• 

  

  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
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  /10

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft

  85 E Birch Rd Unit 15, Stratton, VT 05360

  Neighboring the Stratton Training and Fitness Center, Vantage Point offers two bedroom, two bath condominiums coveted for their convenience and southern exposure. Complete with large windows, wood burning fireplaces, full kitchens, and ample closet space, these units are perfect for growing families and couples who like to entertain. Residents enjoy private parking and complimentary shuttle to

  Edwin Kevil Stratton Real Estate

  85 E Birch Rd Unit 15, Stratton, VT 05360
• 

  

  /51

  $845,000

  • 4 Beds
  • 4 Baths
  • 3,987 Sq Ft

  6235 Grafton Rd, Grafton, VT 05146

  1820 sunny farmhouse on 53 acres with comfortable additions, energy saving updates, and long frontage on Stiles Brook, running through the property. Recent first floor bedroom has handicap accessible adjoining bathroom (walk-in shower and clawfoot tub). Many windows have been replaced and full insulation added. One recent addition is the south-facing "sun room" - warm in the winter with its

  Judy Dickison Barrett & Valley Assoc. Inc

  6235 Grafton Rd, Grafton, VT 05146
• 

  

  /19

  $150,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  59 Brookside Dr Unit 8, Brattleboro, VT 05301

  Low maintenance, affordable and desirable ground floor unit. Perched up high in Brookside development sits this cute efficient one bedroom condo. Inviting flow with a pass thru from the kitchen into the dining and the spacious living room has a great brand new slider out to your spacious level yard. Get creative and build a terrace to enjoy your summer evenings. The large bedroom with double

  Angela Sherman Brattleboro Area Realty

  59 Brookside Dr Unit 8, Brattleboro, VT 05301
• 

  

  /35

  $649,000

  • 3 Beds
  • 3 Baths
  • 2,939 Sq Ft

  282 Melendy Hill Rd, South Londonderry, VT 05155

  Perfectly situated in the heart of Southern Vermont, this immaculate country Cape in South Londonderry offers the best of four-season living. Just minutes to Stratton, Magic, and Bromley Mountains, the property provides effortless access to skiing and snowboarding in winter. In summer, enjoy kayaking at Lowell Lake, golf at Stratton, or live theater at the Weston Playhouse. Everyday conveniences

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  282 Melendy Hill Rd, South Londonderry, VT 05155
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  /60

  $655,000

  • 4 Beds
  • 3 Baths
  • 2,344 Sq Ft

  879 Glebe Mountain Rd, West Townshend, VT 05359

  SOARING GLASS, SOARING SPIRITS, SKIING DELIGHTCome see this architecturally dramatic contemporary four bedroom, three bath home replete with glass to the sky, cathedral ceilings, gorgeous mountain views, wood burning fireplace and end of road privacy on almost ten acres. Perched square in the middle of ski country and close to the three charming towns of Londonderry, Grafton and Chester, you

  Zachary Zupan EXP Realty

  879 Glebe Mountain Rd, West Townshend, VT 05359
• 

  

  /32

  $559,000

  • 3 Beds
  • 3 Baths
  • 2,080 Sq Ft

  9 Greer Ct, Wilmington, VT 05363

  Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Greer Ct, Wilmington, VT 05363
• 

  

  /47

  $570,000

  • 4 Beds
  • 2 Baths
  • 1,937 Sq Ft

  149 Dix Ln, Whitingham, VT 05361

  Open House Saturday September 13, noon to 2:00 - Tucked away on a quiet, town-maintained dead end road this Vermont country homestead offers the perfect blend of charm, privacy, and practicality. Set on 34+ acres, this property has woodlands, pasture and hay fields that have supported a working farm with livestock for the past 5 years. This property is well suited for those seeking a working

  Sandy Reavill Real Broker LLC

  149 Dix Ln, Whitingham, VT 05361
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  /58

  $568,000

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  192 Western Ave, Brattleboro, VT 05301

  Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

  Claire Renaud Berkley & Veller Greenwood Country

  192 Western Ave, Brattleboro, VT 05301
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  /60

  $539,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  16 Nutmeg Ln, West Dover, VT 05356

  Step into this warm, inviting home, and you may never want to leave. Tucked away on a private road just three minutes from Mount Snow's north entrance, this sunny retreat offers winter views of the mountain and a lifestyle that feels both relaxed and rejuvenating. Situated on 3.7 combined acres (2.75 in Dover, 0.95 in Stratton), there's plenty of open lawn space for kids and pets to run free.

  Richard Caplan Deerfield Valley Real Estate

  16 Nutmeg Ln, West Dover, VT 05356
• 

  

  /60

  $565,000

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft

  7 Grassy Brook Rd, Brookline, VT 05345

  Incredible Opportunity! This fully renovated, move-in ready retreat is perfectly situated on the picturesque West River—not in a flood zone (see disclosures). Enjoy your own private beach and waterfront lifestyle at its finest. Whether you’re seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the

  Flex Realty Group Flex Realty

  7 Grassy Brook Rd, Brookline, VT 05345
• 

  

  /31

  $556,000

  • 3 Beds
  • 2 Baths
  • 1,522 Sq Ft

  174 Whites Hill Rd, Dover, VT 05356

  Nestled amidst over 20 acres of pristine land, this Moosehead log home offers the perfect blend of privacy and breathtaking views. Imagine living without the burden of an electric bill, as this property is equipped with a complete solar power system and a backup generator, ensuring you have all the modern conveniences while embracing a sustainable lifestyle.Whether you're working remotely

  Regina Perrotto Skihome Realty

  174 Whites Hill Rd, Dover, VT 05356
• 

  

  /50

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,761 Sq Ft

  532 Sherwood Forest, Londonderry, VT 05148

  Relax and Reconnect in the Heart of Vermonts Green Mountains.Tucked into a peaceful woodland setting, this warm and welcoming mountain retreat is all about comfort, character, and calm. Surrounded by trees and bathed in filtered natural light, the home blends into its serene landscape with expansive windows, cathedral ceilings, and glowing wood interiors throughout. At its heart, a striking

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  532 Sherwood Forest, Londonderry, VT 05148
• 

  

  /41

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

  152 Our Rd, Putney, VT 05346

  Delayed Showings - OPEN HOUSE Sat 9/20 from 10am to noon. Log Home Retreat on 4.7 Acres in Putney, VTTucked back on a quiet road, is welcoming 2-bedroom, 2-bath log home set on 4.7 private acres. A circular driveway brings you to the home, where a broad front porch invites you to slow down and take in the surroundings.Inside, you’ll find new flooring throughout the lower

  Morriah Adams BHG Masiello Brattleboro

  152 Our Rd, Putney, VT 05346
• 

  

  /60

  $2,900,000

  • 5 Beds
  • 7 Baths
  • 5,018 Sq Ft

  15 Mcgovern Ln, Wilmington, VT 05363

  Custom Mountain Retreat Adjacent to The Hermitage Club on 2.76 AcresThis five-bedroom, seven-bathroom mountain retreat is a true work of art, seamlessly blending modern sophistication with Vermont’s rustic charm. Designed by acclaimed architect Ken Pursley and thoughtfully curated by interior designer Bronwyn Ford, this residence offers a unique blend of clean architectural lines, natural

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  15 Mcgovern Ln, Wilmington, VT 05363

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