2,724

Windsor, VT Homes

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    • /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
  • /59

    $669,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,605 Sq Ft

    31 Palmer Rd, Chester, VT 05143

    This is not your typical Vermont farmhouse—it’s far better. Surrounded by rolling fields and pastoral views, this beautifully updated home combines classic country charm with modern ease. Inside, you’ll find a warm, sunlit layout anchored by a stunning chef’s kitchen featuring high-end Viking appliances, granite counters, and custom cabinetry. The spacious primary suite is a luxurious retreat,

    Daire Gibney Barrett and Valley Associates Inc.

    31 Palmer Rd, Chester, VT 05143
  • /18

    $295,000 Sold Nov 01, 2024

    • 1,487 Sq Ft
    • $198/SF
    • 41 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1910

    3264 Trebo Rd, Chester, VT 05143

    Discover the potential of this 1910 farmhouse, nestled on 15 picturesque acres at the corner of Trebo Rd and Crow Hill Rd. 5 of the acres are across the road featuring a large pond big enough for swimming and kayaking, this property offers a canvas for your vision. The Farmhouse is in need of extensive rehab but whether renovating the existing structure or building anew this property is ideal for

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3264 Trebo 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
  • /42

    $315,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft

    4150 Trebo Rd, Chester, VT 05143

    This lovingly maintained manufactured home is just waiting for its new owner to enjoy! Located less than 10 mins from North Springfield and just 20 mins to Ludlow on a quiet dirt road. Enter through the large multi-purpose room with views of the pond and perennial gardens. Laundry is conveniently located in the hallway off the kitchen. A wood stove in the living room adds charm and warmth.

    Alexandra Eatmon Kelley Real Estate, Inc.

    4150 Trebo Rd, Chester, VT 05143
  • /39

    $715,000 Sold Oct 26, 2024

    • 1,735 Sq Ft
    • $412/SF
    • 108 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2021

    276 Old Coach Rd, Chester, VT 05143

    This magnificent newly constructed home has it all! Located in the peaceful Popple Dungeon area of Chester, Vermont, you'll feel a million miles away from the world, nestled within 29 beautifully wooded acres along the South Branch of the Williams River. With just a short walk, you have over 1/4 mile of your very own stream to cool off in. There is no urban glow, little to no traffic, and the

    Daire Gibney Barrett and Valley Associates Inc.

    276 Old Coach 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
  • /47

    $1,500,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 4,400 Sq Ft

    465 Pennell Rd, Chester, VT 05143

    Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options.The setting is nothing short of spectacular. Enjoy

    Gary Coger Four Seasons Sotheby's Int'l Realty

    465 Pennell Rd, Chester, VT 05143
  • /12

    $124,000 Sold Oct 25, 2024

    • 630 Sq Ft
    • $197/SF
    • 6 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1940

    22 White Rd, Chester, VT 05143

    Priced below town assessment and just in time for hunting season, this cute cottage/camp is being sold "as is." This camp sits on 1.1 acres of land, septic tank installed 10 to 15 years ago. It features living room, kitchen, bedroom and a 3/4 bath on the main floor and a loft in part of the second floor. It also has a shed and an outhouse. Don't miss this opportunity!!!

    Darlene Conca Keller Williams Realty Metro-Keene

    22 White Rd, Chester, VT 05143
    • /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
  • /36

    $1,650,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 2,614 Sq Ft

    938 Stigers Rd, Chester, VT 05143

    Welcome to 938 Stigers Road, a masterpiece in the mountains! Discover a stunning fusion of artistry and craftsmanship in this exquisite timber frame home, tucked away in the serene beauty of the mountains.This residence is the inspired creation of a visionary artist and a skilled builder, resulting in a one-of-a-kind retreat where design and nature are in perfect harmony.Fall in love with

    Liz Moore Four Seasons Sotheby's Int'l Realty

    938 Stigers Rd, Chester, VT 05143
  • /37

    $255,000 Sold Oct 18, 2024

    • 960 Sq Ft
    • $266/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1940

    468 Vt Route 103 S, Chester, VT 05143

    Come check out this Main St., turn-key charmer, on a level corner lot, in the Village of Chester. A great neighborhood, walking distance to local shops, schools and in town amenities. You'll love the convenience of the attached (via breezeway) one car garage. This home boasts new paint in every room, updated floors, kitchen and bath, with new furnishings and mattresses. The lighting in the

    Frank Provance Diamond Realty

    468 Vt Route 103 S, Chester, VT 05143
    • /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
  • /27

    $185,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 616 Sq Ft

    501 Gates Rd, Chester, VT 05143

    If you're looking for a smaller footprint, or tiny home living, this is a great option! One bedroom, one bath mobile home in an absolutely gorgeous setting! Sitting on it's own 2+ acres, you'll a large yard with a firepit to enjoy the summer evenings while you gaze out over stone walls to a beautiful view. This property is quiet and peaceful, but not far from several ski areas and state parks

    Rebecca Seymour Brattleboro Area Realty

    501 Gates Rd, Chester, VT 05143
  • /38

    $680,000 Sold Oct 17, 2024

    • 1,171 Sq Ft
    • $581/SF
    • 53 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1990

    2253 White Rd, Chester, VT 05143

    Stunning acreage surrounds this charming home in Windham, Vermont.110 acres of curated land with trails throughout. Lots of places to explore and enjoy, all on your own land! A quintessential get-away with a large screened-in porch overlooking the waterfall and pond. Follow the bridge across the pond to the meadow and trails. The extensive trail network is well maintained, meandering throughout

    Alison Cummings Cummings & Co

    2253 White 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
  • /53

    $450,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    4877 Vt Route 103 N, Chester, VT 05143

    Tucked along the scenic curves of Route 103 & surrounded by the rolling beauty of Chester, Vermont, this unique French Provincial–meets–Vermont cabin is more than just a house—it’s an invitation to breathe deeper, slow down, & reconnect with the rhythm of nature. Wake each morning to the soothing sound of a nearby creek & the scent of fresh mountain air drifting through the trees. Step outside

    Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
  • /16

    $257,000 Sold Oct 11, 2024

    • 1,227 Sq Ft
    • $209/SF
    • 6 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1983

    192 Kevadus Cir, Chester, VT 05143

    This Ranch-style home is tucked away in the back of the Kevadus Circle neighborhood and is ready for its next owner! The main level features three bedrooms, 1 bathroom with a classic ranch layout giving ample space for both the kitchen and living room. There are two additional bonus rooms that could serve as an office, playroom, or even extra storage both of which include closets and below-grade

    Thaddeus Abare Barrett and Valley Associates Inc.

    192 Kevadus Cir, 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
  • /4

    $106,000 Sold Oct 07, 2024

    • Land
    • 10 Acres
    • $10,495 per Acre
    • 82 Days On Market

    1599 Mattson Rd, Chester, VT 05143

    Experience the tranquility of country living with this stunning 10.1-acre property. Enjoy breathtaking views, a fully functional septic system, and a drilled well. The property features a solid structure and 2.5 acres of maintained land, complete with a chicken coop, an apple tree, and blueberry bushes. Located in a quiet neighborhood, this land offers peace and privacy. Additionally, over 7

    Amy Vashaw Twin State Realty LLC

    1599 Mattson 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
  • /29

    $325,000 Sold Oct 04, 2024

    • 1,137 Sq Ft
    • $286/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1983

    201 Hill Top Rd, Chester, VT 05143

    Located just outside of Chester is this three bedroom log home that is close to several resorts. Expansive decks and room for your garden on over five acres. Two out buildings and a nearby seasonal stream. Interior has a cathedral ceiling spanning to the second floor bedroom. Living room has a unique pellet stove to help keep you warm during winter. Kronaspan Rocko flooring on the main floor

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    201 Hill Top Rd, 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
  • /29

    $277,500 Sold Oct 01, 2024

    • 910 Sq Ft
    • $305/SF
    • 57 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1950

    3483 Popple Dungeon Rd, Chester, VT 05143

    This well maintained home is located on a country road in Chester that meanders along a brook. One level living with high ceilings and tasteful upgrades throughout. A wood stove warms the living space in the cooler months. A wood shed and patio area located off the main living area, perfect to enjoy outdoor dining. A heated two car garage with a second floor that would be perfect to finish off

    Jessica Citera Cummings & Co

    3483 Popple Dungeon Rd, Chester, 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
  • /9

    $137,500 Sold Sep 23, 2024

    • Land
    • 13 Acres
    • $10,991 per Acre
    • 355 Days On Market

    00 Coach Rd, Chester, VT 05143

    This beautiful 12.51 acre in town lot is one of the last of it's kind! This lot features long range Views, extremely easy access to downtown Chester being only 3 minutes from the Chester green, and a pond that could make this property the perfect Vermont get-away. The owners have subdivided this parcel from their larger parcel and have agreed to allow for a 50 foot wide right-of-way for a

    Thaddeus Abare Barrett and Valley Associates Inc.

    00 Coach Rd, Chester, VT 05143
    • /24

      Est $267,501 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,096 Sq Ft

      1369 Flamstead Rd, Chester, VT 05143

      1369 Flamstead Rd, Chester, VT 05143
  • /38

    $750,000 Sold Sep 20, 2024

    • 2,722 Sq Ft
    • $276/SF
    • 67 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1990

    2401 N Hill Rd, Chester, VT 05143

    With an excellent layout, special features and prime location, this four bedroom, two and a half bath cape in Andover is a must see! It sits on 4+ acres of manicured grounds with a babbling brook running through the property. Situated between quintessential Weston and the action of Ludlow, it is easy to access, a peaceful setting surrounded by a natural Vermont landscape. The area is host to

    Alison Cummings Cummings & Co

    2401 N Hill Rd, Chester, VT 05143
    • /40

      Est $514,064 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,264 Sq Ft

      1187 Potash Brook Rd, Chester, VT 05143

      1187 Potash Brook Rd, Chester, VT 05143
  • /39

    $355,000 Sold Aug 29, 2024

    • 2,085 Sq Ft
    • $170/SF
    • 19 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1993

    43 Northfield Dr, North Springfield, VT 05150

    Nestled in a quiet neighborhood, this center stair cape has so many features that it should check all your boxes. Main level living features an open concept kitchen, living and dining room. A bedroom/office is situated on the main floor as well as a half bath. The four-season porch with large windows will become the favorite room in the house! Upstairs you'll find two bedrooms, full bath and a

    Joseph Karl William Raveis Real Estate Vermont Properties

    43 Northfield Dr, North Springfield, VT 05150
    • /40

      Est $750,483 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,166 Sq Ft

      1573 Trebo Rd, Chester, VT 05143

      1573 Trebo Rd, Chester, VT 05143
  • /34

    $570,000 Sold Aug 21, 2024

    • 1,856 Sq Ft
    • $307/SF
    • 28 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1967

    405 Church St, Chester, VT 05143

    The warmth and charm of this beautifully renovated cape will capture your heart! Extensive renovations of the interior design and exterior, with energy efficiency in mind, have been aesthetically designed and laid out. A lovely back entry covered porch with Mahagony decking greets you as you enter the main level to the kitchen with handsome custom cabinetry detailed with butcherblock counters and

    Mary Mayhew Snyder Donegan Real Estate Group

    405 Church St, Chester, VT 05143
    • /13

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 852 Sq Ft

      28 Mineral Spring Rd, Chester, VT 05143

      28 Mineral Spring Rd, Chester, VT 05143
  • /40

    $562,725 Sold Aug 15, 2024

    • 1,908 Sq Ft
    • $295/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1992

    1716 Brockway Mills Rd, Chester, VT 05143

    This quintessential Vermont property offers 8.9 acres with gorgeous fields, stunning long range views and wonderful privacy. The owned solar array provides for all of the properties electrical usage. A small greenhouse is ready to help you with the substantial gardens and raised beds! Located a short drive off of RT 91 in close proximity to Chester, Grafton and Springfield VT. 45 min to Hanover

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    1716 Brockway Mills Rd, Chester, VT 05143
    • /38

      Est $352,275 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,349 Sq Ft

      616 Mattson Rd, Chester, VT 05143

      616 Mattson Rd, Chester, VT 05143
  • /40

    $499,000 Sold Aug 09, 2024

    • 2,210 Sq Ft
    • $226/SF
    • 21 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1976

    215 Lower Bartonsville Rd, Chester, VT 05143

    A gem of a home and a gardener's delight await you at this splendid property located in Lower Bartonsville. This contemporary, 3-bedroom and 2.5 bath home sits on 15.2 acres of combined expansive open fields, wooded land with trails and landscaped grounds. Enter through a bright sunroom with custom designed woodwork. The home’s exposed beams and tasteful wood accents add character and warmth

    Laura D'Angelo Berkley & Veller Greenwood Country

    215 Lower Bartonsville Rd, Chester, VT 05143
    • /36

      Est $456,428 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,665 Sq Ft

      231 Snell Rd, Chester, VT 05143

      231 Snell Rd, Chester, VT 05143
  • /26

    $100,000 Sold Aug 09, 2024

    • Land
    • 2.30 Acres
    • $43,478 per Acre
    • 8 Days On Market

    505 Hidden Heights Rd, Chester, VT 05143

    Discover the perfect blend of tranquility and convenience with this 2.3-acre country building lot, nestled in a well-established neighborhood outside the beautiful village of Chester, Vermont. This idyllic parcel boasts a cleared building site, complete with a newly installed drilled well and a state-approved wastewater system designed for a 4-bedroom home. Enjoy this wonderful location on a

    Daire Gibney Barrett and Valley Associates Inc.

    505 Hidden Heights Rd, Chester, VT 05143
    • /25

      Est $292,802 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      242 Mattson Rd, Chester, VT 05143

      242 Mattson Rd, Chester, VT 05143
  • /35

    $110,000 Sold Aug 09, 2024

    • 704 Sq Ft
    • $156/SF
    • 10 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1960

    1291 Potash Brook Rd, Chester, VT 05143

    Situated on the babbling Potash Brook is this wonderful open concept camp. With over 300 feet of brook frontage to enjoy, you feel like you're in the middle of the woods. Step into the spacious entry/mudroom where you'll also see the water system, a large closet and full bath with an incinerating toilet. The water is heated by a propane fired Rinnai water heater. You'll love the openness of

    Frank Provance Diamond Realty

    1291 Potash Brook Rd, Chester, VT 05143

Showing Results 121 - 160, Page 4 of 18

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