Windham County, VT Homes

• 

  

  

  /56

  $350,000 Sold Oct 08, 2025

  • 1,004 Sq Ft
  • $349/SF
  • 5 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1967

  1077 Grassy Brook Rd, Brookline, VT 05345

  Nestled in the woods on a double lot totaling 10 acres along Grassy Brook Road, this charming one-bedroom, one-bathroom cabin offers the perfect blend of rustic comfort and natural beauty. Inside, the open living space is anchored by a Hearthstone woodstove, creating a warm and inviting atmosphere throughout the seasons. Enjoy the soothing sound of the brook just outside your door. Whether

  Claire Renaud Berkley & Veller Greenwood Country

  1077 Grassy Brook Rd, Brookline, VT 05345
• 

  

  

  /44

  Est $298,596 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  556 Stratton Arlington Rd, West Wardsboro, VT 05360

  556 Stratton Arlington Rd, West Wardsboro, VT 05360
• 

  

  

  /36

  $529,000

  • 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
• 

  

  /2

  $345,000 Sold Oct 07, 2025

  • 1,120 Sq Ft
  • $308/SF
  • 10 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1986

  154 Reed Rd, Chester, VT 05143

  Nature surrounds this charming cabin-style home, tucked into the woods and overlooking a peaceful pond. Privately situated, the home features an open-concept living area with a vaulted ceiling, inviting in natural light and offering views of the water. Step outside to a brand-new deck that extends your living space outdoors. The cozy kitchen is both functional and full of character, with

  Jessica Landers Barrett and Valley Associates Inc.

  154 Reed Rd, Chester, VT 05143
• 

  

  

  /35

  Est $195,459 Not Listed For Sale

  • 5 Beds
  • 1.5 Baths
  • 2,751 Sq Ft

  3 Granger St, Bellows Falls, VT 05101

  3 Granger St, Bellows Falls, VT 05101
• 

  

  /11

  $795,000

  • 4 Beds
  • 3 Baths
  • 3,409 Sq Ft

  633-635 Vermont Route 100, Stratton, VT 05360

  Great family compound or use one and rent the other. There are 2 homes on this property with direct access to VAST and the National Forest and `1.6 miles to the North entrance of Mt. Snow. Great opportunity with an excellent rental history. Both houses have full walk-out daylight lower levels, 2 decks and a hot tub at each home. Both homes were remodeled in 2014 including new roofs, windows and

  Ginny Read Read Realty LTD

  633-635 Vermont Route 100, Stratton, VT 05360
• 

  

  /15

  $190,000 Sold Oct 07, 2025

  • 802 Sq Ft
  • $237/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1980

  84 Signal Pine Rd, Putney, VT 05346

  Located just outside the Village of Putney, this privately sited home features 7.70 +/- acres of trees and meadow along with a pond area that's currently overgrown but could potentially be reclaimed for your enjoyment or just appreciating nature. The structure itself needs rehab as it's been stripped down to studs and needs attention inside and outside. However the location is great being close

  A.J. Bellville Bellville Realty

  84 Signal Pine Rd, Putney, VT 05346
• 

  

  /40

  Est $384,040 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,206 Sq Ft

  6 Hapgood St, Bellows Falls, VT 05101

  6 Hapgood St, Bellows Falls, VT 05101
• 

  

  /59

  $275,000

  • 2 Beds
  • 1 Bath
  • 715 Sq Ft

  81 Parish Hill Rd, Newfane, VT 05345

  Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

  Chad Bruyette Whitetail Properties Real Estate, LLC

  81 Parish Hill Rd, Newfane, VT 05345
• 

  

  /27

  $950,000 Sold Oct 07, 2025

  • 3,000 Sq Ft
  • $317/SF
  • 49 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2006

  6B Foliage Ln, Dover, VT 05356

  Stunning renovated Kingswood townhome located conveniently between Mount Snow and the Hermitage Club Resorts in Southern VT. This beautifully updated 4 bedroom, 3.5 bath townhome was built in 2006 and renovated to a bold contemporary style in 2020 by the current owners. No expense was spared at making this a true dream getaway. Upon entry you are greeted by a large, functional mudroom complete

  Adam Palmiter Berkley & Veller Greenwood/Dover

  6B Foliage Ln, Dover, VT 05356
• 

  

  /10

  Est $175,256 Not Listed For Sale

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

  14 Front St, Bellows Falls, VT 05101

  14 Front St, Bellows Falls, VT 05101
• 

  

  /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
• 

  

  /23

  $400,000 Sold Oct 07, 2025

  • 1,750 Sq Ft
  • $229/SF
  • 357 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  43 1st Ln Unit 28, Wilmington, VT 05363

  Beautiful updated condo overlooking the 1st green at the Haystack Golf Club, as well as the mountains and sunsets beyond. This lovely private unit sits right on one of the best courses in New England, and is a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. The interior features a large open living space with vaulted ceilings, updated vinyl

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43 1st Ln Unit 28, Wilmington, VT 05363
• 

  

  /40

  Est $255,967 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,804 Sq Ft

  16 Atkinson St, Bellows Falls, VT 05101

  16 Atkinson St, Bellows Falls, VT 05101
• 

  

  /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
• 

  

  /50

  $260,000 Sold Oct 07, 2025

  • Land
  • 0.7 Acre
  • $371,429 per Acre

  • 19 Days On Market

  184 W Lake Rd, Wilmington, VT 05363

  Rare Lake Raponda Gem – Private Dock, Fire Pit, and More!Welcome to your dream lakefront playground on beautiful Lake Raponda!Private Dock – Enjoy swimming, kayaking, and boating.Fire Pit on the Deck – Perfect for cozy evenings with lake viewsBoat house.Private & Peaceful Setting – Nestled in nature with year-round access.

  Rich Caplan Deerfield Valley Real Estate

  184 W Lake Rd, Wilmington, VT 05363
• 

  

  /39

  Est $198,017 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,023 Sq Ft

  3 Forest St, Bellows Falls, VT 05101

  3 Forest St, Bellows Falls, VT 05101
• 

  

  /44

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
• 

  /2

  $305,000 Sold Oct 06, 2025

  • 1,917 Sq Ft
  • $159/SF
  • 89 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1841

  152 Main St, Grafton, VT 05146

  Motivated Seller! This charming home in Grafton is ready for its next chapter! Centrally located next to the MKT market, offering easy access to the post office, town offices, library, school, inn, church, and local shops. With spacious and bright rooms, the home welcomes you into a main foyer that features a living room and study as its two front rooms. A dining room adjoins the living room and

  Jessica Landers Barrett and Valley Associates Inc.

  152 Main St, Grafton, VT 05146
• 

  

  /40

  Est $308,427 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,245 Sq Ft

  8 Williams Terrace, Bellows Falls, VT 05101

  8 Williams Terrace, Bellows Falls, VT 05101
• 

  

  /45

  $449,000

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

  52A Suntec Loop, Dover, VT 05356

  Introducing the 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

  Prema Fitzpatrick Skihome Realty

  52A Suntec Loop, Dover, VT 05356
• 

  /2

  $266,000 Sold Oct 06, 2025

  • 1,440 Sq Ft
  • $185/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  637 Wiswall Hill Rd, Townshend, VT 05353

  Discover your perfect Vermont escape in this cozy two-story cabin nestled on a sweet, level acre. Whether you're looking for a weekend getaway or a full-time residence, this home offers the ideal blend of rustic charm and everyday functionality. The lower level welcomes you into an open-concept guest or living space, with convenient access to utilities and a fenced-in shaded area—perfect for pets

  Jessica Landers Barrett and Valley Associates Inc.

  637 Wiswall Hill Rd, Townshend, VT 05353
• 

  

  /36

  Est $304,073 Not Listed For Sale

  • Studio
  • 3 Baths
  • 3,368 Sq Ft

  11 Burt St, Bellows Falls, VT 05101

  11 Burt St, Bellows Falls, VT 05101
• 

  

  /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
• 

  

  /26

  $714,000 Sold Oct 06, 2025

  • 4,932 Sq Ft
  • $145/SF
  • 135 Days On Market

  • 18 Beds
  • 8 Baths
  • Built 1900

  29 Canal St, Brattleboro, VT 05301

  High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1br A new owner can step into to this

  Michael Gilman 3GEN Real Estate Inc

  29 Canal St, Brattleboro, VT 05301
• 

  

  /38

  Est $242,991 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,178 Sq Ft

  52 Green St, Bellows Falls, VT 05101

  52 Green St, Bellows Falls, VT 05101
• 

  

  /56

  $475,000

  • 6 Beds
  • 3 Baths
  • 3,954 Sq Ft

  430 Huckle Hill Rd, Vernon, VT 05354

  NEW PRICE!! LOTS OF OPTIONS!! This quality built home can be enjoyed as spacious one floor living. Inside, the main level features gleaming hardwood floors with radiant floor heat and an open-concept layout with vaulted ceilings. The bright kitchen offers granite countertops, stainless steel appliances, a breakfast bar, and space for a kitchen table. The adjoining dining area easily accommodates

  Carol Slocum Keller Williams Realty Metro-Keene

  430 Huckle Hill Rd, Vernon, VT 05354
• 

  

  /55

  $396,500 Sold Oct 06, 2025

  • 1,958 Sq Ft
  • $203/SF
  • 177 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1980

  112 Breezy Acres Dr, Vernon, VT 05354

  Set on a beautifully sunlit, spacious lot, this classic Vermont home offers the perfect balance of comfort, functionality, and charm. Tucked in a quiet neighborhood, the property features a generous layout with thoughtful updates throughout. Inside, enjoy fresh new carpet and paint, brand new energy-efficient windows, a new dishwasher and electric range, enhancing both aesthetics and

  Kristen Ziter Taylor Brattleboro Area Realty

  112 Breezy Acres Dr, Vernon, VT 05354
• 

  

  /36

  Est $243,019 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,638 Sq Ft

  36 Green St, Bellows Falls, VT 05101

  36 Green St, Bellows Falls, VT 05101
• 

  

  /29

  $465,000

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

  132 Pratt Bridge Rd, Jamaica, VT 05343

  Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /28

  $350,000 Sold Oct 06, 2025

  • 1,768 Sq Ft
  • $198/SF
  • 31 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1950

  177 Fairview St, Brattleboro, VT 05301

  Ta Da! This is it! This diamond in the rough was built for the owner in 1950 and has been in the family ever since! The kitchen is huge, large enough for the traditional kitchen table, or a new kitchen island. True, it is vintage, but lots of cabinets and countertop for cooking and open to both living and dining for great parties. The living room is 26 ft long and room for everyone with big

  Christine Lewis Brattleboro Area Realty

  177 Fairview St, Brattleboro, VT 05301
• 

  

  /39

  Est $347,939 Not Listed For Sale

  • 7 Beds
  • 3 Baths
  • 3,780 Sq Ft

  3 Green St, Bellows Falls, VT 05101

  3 Green St, Bellows Falls, VT 05101
• 

  

  /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
• 

  

  /22

  $69,000 Sold Oct 03, 2025

  • Land
  • 10.01 Acres
  • $6,893 per Acre

  • 3 Days On Market

  1051 Maple Hill Ln, Whitingham, VT 05342

  Escape to your own private retreat with this 10-acre wooded lot. This property features a 2018 trailer already on site, making it the perfect base camp for outdoor adventures in every season. Enjoy fishing and boating at the nearby Lake Whitingham and Lake Sadawga in summer both less than 4 miles away, and nearby snowmobile trails for winter fun- check out the VAST trail maps for accessibility.

  Kelly Agrillo Southern Vermont Realty Group

  1051 Maple Hill Ln, Whitingham, VT 05342
• 

  

  /40

  Est $304,924 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 5,404 Sq Ft

  35 School St, Bellows Falls, VT 05101

  35 School St, Bellows Falls, VT 05101
• 

  

  /18

  $220,000

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  5362 Us Route 5, Westminster, VT 05158

  Welcome to this move-in ready home, ideally situated in the heart of picturesque Westminster. This 3-bedroom, 1-bath home offers the perfect blend of charm, comfort and convenience. Step inside from the sunny, porch into a bright and functional kitchen featuring new countertops and easy access to the first-floor laundry area and recently renovated full bath. The layout flows seamlessly into the

  Karen Hoppe Berkley & Veller Greenwood Country

  5362 Us Route 5, Westminster, VT 05158
• 

  

  /26

  $401,000 Sold Oct 03, 2025

  • 2,989 Sq Ft
  • $134/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1967

  215 Old Town Rd, Wilmington, VT 05363

  Utter and complete privacy, and gorgeous ski trail and mountain views, from this hillside retreat, not far from the village of Wilmington and Mount Snow ski resort. Nestled on a private 4+ acres this lovely location has easy access off a town road, tremendous exposure and sunset views to the west and south. The open concept contemporary style is befitting a unique and fun home away from home,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  215 Old Town Rd, Wilmington, VT 05363
• 

  

  /37

  Est $314,831 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,684 Sq Ft

  29 School St, Bellows Falls, VT 05101

  29 School St, Bellows Falls, VT 05101
• 

  

  /20

  $469,000

  • 4 Beds
  • 2 Baths
  • 2,219 Sq Ft

  45 Dover Hill Rd, East Dover, VT 05341

  Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Dover Hill Rd, East Dover, VT 05341
• 

  

  /60

  $625,000 Sold Oct 03, 2025

  • 2,731 Sq Ft
  • $229/SF
  • 65 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1880

  49 Tyler St, Brattleboro, VT 05301

  Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

  Karen Hoppe Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301

Showing Results 481 - 520, Page 13 of 18