3,370

Windsor, VT Homes in ZIP Code 05143

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    • /40

      Est $224,424 Not Listed For Sale

      • 7 Beds
      • 8 Baths
      • 4,475 Sq Ft

      244 Main St, Chester, VT 05143

      244 Main St, Chester, VT 05143
  • /18

    $196,000

    • Land
    • 32 Acres
    • $6,125 per Acre

    100 Stagecoach Rd, Town of Rockingham, VT 05156

    A very cool cabin on a beautiful, ultimate private 32 +/- acres. The cabin is 400 square feet with a spacious loft. The deck faces east to very pretty CT River Valley Views. There is no water or power, only an outhouse and woodstove for Vermont getaways, a hunting camp or snowmobile extremists. Seller has invested roughly $30,000 into improving Stagecoach Rd. Property is enrolled in the current

    Kristen Ziter Taylor Brattleboro Area Realty

    100 Stagecoach Rd, Town of Rockingham, VT 05156
  • /10

    $35,500 Sold Jan 17, 2025

    • Land
    • 9 Acres
    • $4,057 per Acre
    • 17 Days On Market

    0 Gould Rd Unit 5023598, Chester, VT 05143

    Escape to your own private sanctuary in southern Vermont! This 8.75-acre wooded lot offers the perfect retreat, with Beaver Meadow Brook gently running through it, creating a serene and tranquil atmosphere. Whether you're looking for a peaceful off-grid living experience or a scenic camping spot, this property is ideally suited for both. Accessed by an approximately 1/4 mile right-of-way, you'll

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    0 Gould Rd Unit 5023598, Chester, VT 05143
    • /39

      Est $407,157 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,068 Sq Ft

      160 Peck Rd, Chester, VT 05143

      160 Peck Rd, Chester, VT 05143
  • /36

    $575,000

    • 6 Beds
    • 5 Baths
    • 3,217 Sq Ft

    423 Main St, Chester, VT 05143

    Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing

    Betty McEnaney Diamond Realty

    423 Main St, Chester, VT 05143
  • /59

    $608,000 Sold Dec 27, 2024

    • 2,512 Sq Ft
    • $242/SF
    • 27 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    50 Howard Rd, Chester, VT 05143

    Discover your private sanctuary in Chester, Vermont! This beautifully upgraded 1986 post-and-beam Saltbox is set on 5 serene, wooded acres, offering 3 bedrooms, 2.5 bathrooms, and a versatile living space. Recent updates, totaling over $100k, include a renovated kitchen with new flooring, countertops, sink, faucet, and backsplash and updated bathrooms on 1st and 2nd floors. A new skylight will be

    Jeremy Collins Ridgeline Real Estate

    50 Howard Rd, Chester, VT 05143
    • /40

      Est $476,632 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,812 Sq Ft

      1937 Green Mountain Turnpike, Chester, VT 05143

      1937 Green Mountain Turnpike, Chester, VT 05143
  • /18

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,248 Sq Ft

    26 Dorman Rd, Andover, VT 05143

    Prepare for an exhilarating mountain getaway at this enchanting four-bedroom chalet, nestled on a lush 2.1-acre estate in the heart of Andover. 2025 Ski season has been epic so far! Envision yourself minutes away from four renowned ski resorts, making this the perfect launchpad for your winter adventures. Immerse yourself in the local charm with easy access to the VAST trail network, offering a

    Daire Gibney Barrett and Valley Associates Inc.

    26 Dorman Rd, Andover, VT 05143
  • /25

    $107,000 Sold Dec 27, 2024

    • Land
    • 8 Acres
    • $13,375 per Acre
    • 206 Days On Market

    0 Brookside Dr Unit 4994316, Chester, VT 05143

    Brookside Dr. Chester. Eight acres high on a hill side, a cross valley view with a little clearing, possible down the valley too. Property is partially wooded, has a small stream and has a field are that will need to be reclaimed for a nice house site. Survey shows a spring. State permit WW-2-2138 for a 5 bedroom too Own your piece of Vermont.

    Mike England Michael England Real Estate

    0 Brookside Dr Unit 4994316, Chester, VT 05143
    • /34

      Est $983,093 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,221 Sq Ft

      835 Quarry Rd, Chester, VT 05143

      835 Quarry Rd, Chester, VT 05143
  • /10

    $135,000

    • Land
    • 13 Acres
    • $10,120 per Acre

    00 Hill Top Rd, Andover, VT 05143

    If you're searching for the perfect lot to build your dream home, this 13+ acre property could be just what you've been looking for! Nestled on a peaceful road, this expansive lot offers a prime opportunity to create your ideal home while staying close to top local attractions, including the stunning mountains of Okemo, Stratton, Magic, and Bromley. With permits already in place for a

    Flex Realty Group Flex Realty

    00 Hill Top Rd, Andover, VT 05143
  • /13

    $125,000 Sold Dec 19, 2024

    • Land
    • 3.32 Acres
    • $37,651 per Acre
    • 254 Days On Market

    Lot 49 Andover Ridge Rd Unit 49, Andover, VT 05143

    Newly cleared mountaintop land in Andover Vermont! This lovely lot has both sunrise and sunset as well as gorgeous long range mountain vistas from all angles, not to be missed. Andover Ridge Road is a stunning community with beautiful homes angled to catch the terrific panoramic views. This property has a small natural pond at the roadside as well as a cleared site and still plenty of hardwood

    Erica Reynolds Southern Vermont Realty Group

    Lot 49 Andover Ridge Rd Unit 49, Andover, VT 05143
    • /27

      Est $420,656 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,412 Sq Ft

      837 Vt Route 11 W, Chester, VT 05143

      837 Vt Route 11 W, Chester, VT 05143
  • /22

    $275,000

    • Land
    • 91 Acres
    • $3,022 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this

    Daire Gibney Barrett and Valley Associates Inc.

    000 Green Mountain Turnpike, Andover, VT 05143
  • /36

    $925,000 Sold Dec 13, 2024

    • 2,916 Sq Ft
    • $317/SF
    • 169 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1850

    2181 White Rd, Chester, VT 05143

    Nestled along a serene country road, this enchanting home exudes rustic charm and timeless elegance. The “Twin Brooks” that flank the property and private pond round out the much desired water features. Hand hewn beamed ceilings welcome you into a cozy haven where every detail tells a story. Adorned with captivating features, the interior boasts a marble-faced fireplace, a soapstone stove

    Lee Brown Four Seasons Sotheby's Int'l Realty

    2181 White Rd, Chester, VT 05143
    • /33

      Est $737,784 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,214 Sq Ft

      50 Goldthwaite Rd, Chester, VT 05143

      50 Goldthwaite Rd, Chester, VT 05143
  • /41

    $6,950,000

    • 8 Beds
    • 7.5 Baths
    • 8,262 Sq Ft

    3800 Weston-Andover Rd, Andover, VT 05143

    Escape to Moosewalk Lane, a fully furnished and equipped luxury estate in Andover, Vermont, set on 384 acres in the iconic Green Mountains. This one of a kind property offers a rare blend of seclusion, natural beauty, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame construction, the

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • /31

    $1,900,000 Sold Dec 10, 2024

    • 4,729 Sq Ft
    • $402/SF
    • 38 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1980

    231 Christmas Tree Farm Rd, Chester, VT 05143

    The Cabin is a private retreat on 245 acres with sweeping views of the Green Mountains. Rebuilt in 2024, the home blends modern amenities with the rustic charm of a log cabin. A long drive follows a mountain brook to the cabin. Inside, a bright, airy space features a spacious kitchen flowing into the dining and living area, centered around a stone fireplace and floor-to-ceiling windows. The

    Dia Jenks LandVest, Inc/Woodstock

    231 Christmas Tree Farm Rd, Chester, VT 05143
    • /39

      Est $886,428 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,308 Sq Ft

      76 Goldthwaite Rd, Chester, VT 05143

      76 Goldthwaite Rd, Chester, VT 05143
  • /40

    $495,000

    • 2,280 Sq Ft

    1377 Vermont 103, Chester, VT 05143

    Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business. There are 2 separate buildings. One needs to be finished, main building 3 floor could be finished for more living space.

    Mike England Michael England Real Estate

    1377 Vermont 103, Chester, VT 05143
  • /14

    $185,000 Sold Dec 09, 2024

    • Land
    • 36 Acres
    • $5,103 per Acre
    • 115 Days On Market

    173 Horsenail Hill Rd, Windham, VT 05359

    Over 35 acres with more than 2,500 feet of PRIME ROAD FRONTAGE on Vermont Route 11, a major east west corridor from Springfiled to Manchester. This open level lot is a perfect spot for your business starting from the ground up. With great exposure and easy access to Route 91 and Vermont Route 7 this ultimate location is waiting for you and your ideas.

    Frank Provance Diamond Realty

    173 Horsenail Hill Rd, Windham, VT 05359
    • /30

      Est $1,189,881 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,192 Sq Ft

      308 Adams Rd, Chester, VT 05143

      308 Adams Rd, Chester, VT 05143
  • /21

    $185,000

    • Land
    • 14 Acres
    • $13,252 per Acre

    0 Valley View Dr Unit 5009431, Andover, VT 05143

    This piece of land offers a unique combination of privacy and expansive long-range views at an elevation of 2000+ feet, making it an ideal location for your dream home in Southern Vermont. Nestled within a serene community of fine homes, this lot is one of the few remaining opportunities to build in this desirable area. The land has a waste water permit and comes with a community leach field

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    0 Valley View Dr Unit 5009431, Andover, VT 05143
  • /10

    $160,000 Sold Dec 06, 2024

    • Land
    • 9 Acres
    • $18,391 per Acre
    • 37 Days On Market

    33 Green Mountain Turnpike, Town of Rockingham, VT

    Possibilities abound on this property which has over 8 acres of land with more than 1600’ of road frontage on 2 roads! There is an existing single wide home, garage and small animal shed on the property. The property also has an existing well and septic. There is a secluded feel while still being convenient to amenities such as: half an hour to Okemo, 45 minutes to Stratton, 6.5 miles to 91. Come

    Jennifer Andrus R.H. Thackston & Company

    33 Green Mountain Turnpike, Town of Rockingham, VT
    • /19

      Est $224,645 Not Listed For Sale

      • 2 Beds
      • 500 Sq Ft

      83 Potash Brook Rd, Chester, VT 05143

      83 Potash Brook Rd, Chester, VT 05143
  • /43

    $169,000

    • 4 Beds
    • 4 Baths
    • 3,024 Sq Ft

    515 Main St, Chester, VT 05143

    Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture,

    John Tolosky Barrett and Valley Associates Inc.

    515 Main St, Chester, VT 05143
  • /40

    $635,000 Sold Dec 06, 2024

    • 1,876 Sq Ft
    • $338/SF
    • 89 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2012

    994 Dodge Rd, Chester, VT 05143

    Discover this extraordinary property, available for the first time! Nestled on 26 pristine, private acres at the end of a serene road, this 3-bedroom contemporary home is a true gem. Impeccably maintained by its original owners, every detail of this residence has been thoughtfully designed. The home features a welcoming entryway mudroom, a cozy sitting area leading into the dining space, and a

    Gary Coger Four Seasons Sotheby's Int'l Realty

    994 Dodge Rd, Chester, VT 05143
    • /3

      Est $256,781 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,746 Sq Ft

      146 Logan Dr, Chester, VT 05143

      146 Logan Dr, Chester, VT 05143
  • /24

    $95,000

    • Land
    • 10 Acres
    • $9,135 per Acre

    0 Snell Rd, Chester, VT 05143

    This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Utility pole is at the road

    Geralyn Donohue Engel & Völkers Okemo

    0 Snell Rd, Chester, VT 05143
  • /34

    $1,250,000 Sold Dec 05, 2024

    • 2,466 Sq Ft
    • $507/SF
    • 27 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2004

    209 Ingraham Hill Rd, Chester, VT 05143

    Large acreage and vast views. The cabin on Steadman Hill is a newly finished off-grid home on 477 acres. With breathtaking south-facing views of a large meadow and the Green Mtns, this retreat offers an inspiring setting to write the great American novel, create art, or simply enjoy the peacefulness in nature. The mature woodlands are filled with towering oak, maple and beech trees. The land is

    Dia Jenks LandVest, Inc/Woodstock

    209 Ingraham Hill Rd, Chester, VT 05143
    • /19

      Est $365,493 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,551 Sq Ft

      100 Fletcher Hill Rd, Chester, VT 05143

      100 Fletcher Hill Rd, Chester, VT 05143
  • /26

    $219,000

    • Land
    • 28 Acres
    • $7,878 per Acre

    00 Quarry Rd, Chester, VT 05143

    Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel

    Geralyn Donohue Engel & Völkers Okemo

    00 Quarry Rd, Chester, VT 05143
  • /24

    $310,000 Sold Dec 03, 2024

    • 1,293 Sq Ft
    • $240/SF
    • 116 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1988

    1767 Rockingham Rd, Chester, VT 05143

    This beautiful turnkey Log home is the perfect weekend getaway or a convenient and tasteful primary residence. Located less than 30 minutes from both Okemo and Magic Mountain, it offers plenty of opportunities for mountain adventures. Whether you're into skiing, hiking, or simply enjoying the stunning landscapes, you'll find it all within easy reach. The home has recently received numerous

    Thaddeus Abare Barrett and Valley Associates Inc.

    1767 Rockingham Rd, Chester, VT 05143
    • /26

      Est $340,158 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,500 Sq Ft

      154 Fletcher Hill Rd, Chester, VT 05143

      154 Fletcher Hill Rd, Chester, VT 05143
  • /13

    $274,900 Pending

    • 3 Beds
    • 1 Bath
    • 894 Sq Ft

    230 Kevadus Cir, Chester, VT 05143

    This lovely raised ranch is a sight to behold. Impeccably maintained by its current owners, this property is truly in move in condition. New architectural shingles and chimney work in 2016 along with a new furnace, and bathroom remodel in 2023, all you will have to do is sit back and relax on your private back deck enjoying nature. Nicely proportioned living room off the kitchen for easy

    Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
  • /12

    $19,000 Sold Nov 29, 2024

    • Land
    • 6 Acres
    • $3,448 per Acre
    • 183 Days On Market

    0 Remington Rd Unit 12 5001944, Chester, VT 05143

    REUCDUED $18,000.00, PRICED TO SELL! One of the larger lots in the lower Remington subdivision. This private lot has underground power at the lot and the permitted septic is an inground system. Bring your plans and your builder or have the seller build your dream home! PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.

    Frank Provance Diamond Realty

    0 Remington Rd Unit 12 5001944, Chester, VT 05143
    • /21

      Est $427,165 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,848 Sq Ft

      289 Fletcher Hill Rd, Chester, VT 05143

      289 Fletcher Hill Rd, Chester, VT 05143
  • /59

    $1,125,000 Pending

    • 3 Beds
    • 4 Baths
    • 3,739 Sq Ft

    1502 Popple Dungeon Rd, Chester, VT 05143

    Welcome to paradise! Enjoy all four seasons in this handsome, 1989 colonial-style home with modern amenities. From the covered porch, relax and take in views of the front gardens and your land across the road with apple trees and brook frontage. A large solar array is tucked out of sight producing all the power you would need. Behind the house is a fenced-in garden and greenhouse, a couple of

    Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
  • /30

    $685,000 Sold Nov 22, 2024

    • 1,978 Sq Ft
    • $346/SF
    • 88 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1976

    3011 A East Hill Rd, Andover, VT 05143

    Price Adjustment! This gracious country contemporary, on the market for the first time, was designed and finished by its longtime owners, an industrial designer and an interior designer. Beautifully sited in a landscaped setting on a quiet country road, it enjoys distant mountain views and is protected on all sides by woods with nature trails. The 3 bed/3 bath interior is light and airy with

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3011 A East Hill Rd, Andover, VT 05143
    • /38

      Est $331,858 Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 2,426 Sq Ft

      13 Logan Dr, Chester, VT 05143

      13 Logan Dr, Chester, VT 05143

Showing Results 121 - 160, Page 4 of 18

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