3,370

Windsor, VT Homes in ZIP Code 05143

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  • /60

    $638,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,456 Sq Ft

    3236 Weston-Andover Rd, Chester, VT 05143

    Set on a stunning, level 7.38-acre parcel, this beautifully updated farmhouse is turnkey and full of character, comfort, and space! The convenient mudroom offers built-in shelving for your gear and leads into a lovely country kitchen featuring handmade cabinetry, granite countertops, a butcher block island, and a cozy breakfast bar. Step out to the charming front porch to enjoy your morning

    Mendi Michael Engel & Völkers Okemo

    3236 Weston-Andover Rd, Chester, VT 05143
  • /41

    $410,000 Sold Nov 08, 2024

    • 1,410 Sq Ft
    • $291/SF
    • 44 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    56 Hidden Newton Rd, Chester, VT 05143

    This log home in Windham includes a large yard with fruit trees, room for gardening and recreation, privately situated on a quiet dead-end street. Enjoy the peace and quiet of the natural surroundings with a small pond, apple trees and large deck to relax on. This 3 bedroom , 2 bath home has a nice interior flow with an open kitchen/living/dining floor plan. Enter through the large mudroom and

    Alison Cummings Cummings & Co

    56 Hidden Newton 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
  • /19

    $485,000 Pending

    • Studio
    • 2 Baths
    • 4,060 Sq Ft

    12 Common St, Chester, VT 05143

    Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily

    Thaddeus Abare Barrett and Valley Associates Inc.

    12 Common St, Chester, VT 05143
  • /40

    $595,000 Sold Nov 08, 2024

    • 2,080 Sq Ft
    • $286/SF
    • 55 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 2004

    2656 Weston-Andover Rd, Chester, VT 05143

    One of a kind! If you wanted to be 100% off the grid, but in a home that looks & functions like a traditional home, then look no further. This is a special home-from the quiet spot on the Ox Bow with long brook frontage to the handsome architecture & interior detail. No other house will ever be visible, your privacy is protected, but you are minutes from Weston, Chester & Ludlow. The floorplan is

    Betty McEnaney Diamond Realty

    2656 Weston-Andover 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
  • /20

    $215,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 840 Sq Ft

    87 Kevadus Cir, Chester, VT 05143

    This property features an open extended lot with a large private covered deck and expansive backyard. The interior of this home has just been painted Aswell as new carpet throughout. The oversized 1 car garage is great for extra storage or a small work shop. This turn key home could be perfect for someone looking to downsize or a starter home.

    Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, 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
    • /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
  • /41

    $335,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    769 Davidson Hill Rd, Chester, VT 05143

    Simplify your life and reconnect with nature in this peaceful Chester home. Set on over 5 private acres, this 3-bedroom ranch offers easy, one-level living surrounded by Vermont’s natural beauty. Whether you're seeking a low-maintenance primary residence, a country getaway, or a downsizing opportunity, this home delivers comfort without complication. From the wheelchair-accessible ramp to the

    Frank Provance Diamond Realty

    769 Davidson Hill 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
    • /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
  • /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
  • /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
    • /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
  • /55

    $629,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    656 Main St, Chester, VT 05143

    Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass

    Geralyn Donohue Engel & Völkers Okemo

    656 Main St, 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
    • /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
  • /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
  • /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
    • /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
  • /41

    $395,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft

    3091 Route 121, Windham, VT 05359

    Slow down and take time to soak up the charm and character of this sweet house in the beautiful town of Windham! The c. 1860 antique Country Cape is a true testament to the enduring appeal of fine craftsmanship and a life well-lived. The house sits on 12 acres, with a stream and flower-filled meadows beyond, and one of the best front porches in Windham – relax, enjoy the view, and watch the world

    Claudia Harris Mary Mitchell Miller Real Estate

    3091 Route 121, Windham, VT 05359
  • /31

    $1,200,000 Sold Oct 16, 2024

    • 4,804 Sq Ft
    • $250/SF
    • 61 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2003

    1337 Andover Ridge Rd, Andover, VT 05143

    Meticulous and spacious home that has been thoughtfully and lovingly updated on the prestigious Andover Ridge Road. Overlooking the Green Mountain National Forest and the village of Weston, this beautiful custom-built 4800+sf log home exudes privacy, warmth, comfort and charm. The kitchen has heated stone flooring, abundant light and breathtaking views. There are two spacious living areas

    Liz Moore Four Seasons Sotheby's Int'l Realty

    1337 Andover Ridge Rd, Andover, VT 05143
    • /31

      Est $384,763 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,492 Sq Ft

      199 Maple Ridge Rd, Chester, VT 05143

      199 Maple Ridge 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
  • /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
    • /32

      Est $306,414 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,664 Sq Ft

      739 Gould Rd, Chester, VT 05143

      739 Gould Rd, Chester, VT 05143
  • /35

    $199,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,322 Sq Ft

    841 Farrar Rd, Chester, VT 05143

    Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for

    Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

    841 Farrar 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
    • /8

      Est $226,476 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft

      5051 Vt Route 103 N, Chester, VT 05143

      5051 Vt Route 103 N, Chester, VT 05143
  • /20

    $195,000 Under Contract

    • Land
    • 54 Acres
    • $3,615 per Acre

    563 Simonsville Rd, Andover, VT 05143

    Looking for a blank canvas to make your own? Look no further than this beautiful 53+ acres in the quiet town of Andover. The property boasts several potential house seats (close to the road but also some tucked up away in the trees), a pond, high above the river, and convenient road frontages on two publicly maintained roads. Minutes from downtown Chester or Londonderry Vermont. Within 30 minutes

    Erin Kendall EXP Realty

    563 Simonsville Rd, Andover, 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
    • /20

      Est $362,110 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      247 Cavendish Rd, Chester, VT 05143

      247 Cavendish 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
  • /16

    $230,000 Sold Oct 03, 2024

    • 400 Sq Ft
    • $575/SF
    • 7 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 2017

    288 Graves Rd, Baltimore, VT 05143

    Northeastern Log Homes off-grid white pine cabin ( Trailside Model ) situated at the base of Hawks Mountain on 49.7 acres in Baltimore/Weathersfield, Vermont; 400 square feet; well water, both hot and cold, to kitchen area and bathroom; 1000 gallon tank septic system; inside electrical outlets; outside hose faucet; Anderson windows with screens; Vermont Castings wood stove. Power by generator.

    Jason Saphire www.HomeZu.com

    288 Graves Rd, Baltimore, VT 05143
    • /23

      Est $499,215 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,900 Sq Ft

      538 Clemons Rd, Chester, VT 05143

      538 Clemons Rd, 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
  • /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
    • /26

      Est $585,229 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,665 Sq Ft

      529 Nudist Camp Rd, Chester, VT 05143

      529 Nudist Camp Rd, 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

Showing Results 161 - 200, Page 5 of 18

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