2,724

Windsor, VT Homes

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  • /5

    $20,000 Sold Jan 30, 2025

    • Land
    • 1.34 Acres
    • $14,925 per Acre
    • 207 Days On Market

    0 Remington Rd Unit 6 4996522, Chester, VT 05143

    REUCDUED ALMOST $10,000.00, PRICED TO SELL! This affordable lot has under ground power and a permitted inground septic design. Ready for you and your home plans. Just minutes to the Chester Green and an array of outdoor activities to include world class skiing at several different ski areas. PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.

    Frank Provance Diamond Realty

    0 Remington Rd Unit 6 4996522, Chester, VT 05143
    • /40

      Est $1,253,821 Not Listed For Sale

      • 7 Beds
      • 6 Baths
      • 5,566 Sq Ft

      683 Church St, Chester, VT 05143

      683 Church St, Chester, VT 05143
  • /29

    $399,000

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft

    491 Farrar Rd, Chester, VT 05143

    Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

    Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
  • /33

    $210,000 Sold Jan 21, 2025

    • 2,736 Sq Ft
    • $77/SF
    • 47 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2022

    110 Shady Grove Ln, Chester, VT 05143

    Located on private road on Shady Grove Lane, this newly constructed 2.5 story 2 bedroom, 2 bath home on 5.12 +/- acres has been framed. The first floor layout includes a large kitchen/living area with a bedroom and full bath. The second floor includes a full bath with large bedroom. This beautiful home includes a walkout basement. All building materials on site are included with the sale. This

    Rob Weltz Barrett & Valley Assoc. Inc

    110 Shady Grove Ln, Chester, VT 05143
    • /40

      Est $683,388 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,099 Sq Ft

      604 Church St, Chester, VT 05143

      604 Church St, Chester, VT 05143
  • /35

    $199,000

    • 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
  • /6

    $60,000 Sold Jan 21, 2025

    • Land
    • 14 Acres
    • $4,383 per Acre
    • 98 Days On Market

    0 Whitmore Brook Rd, Chester, VT 05143

    This four lot subdivision is a builders dream. The abutting house took two of the lots for a buffer. Two remaining subdivided lots come complete with state permits for waste water and septic designs. Come take a look and bring your plans. These lots average less than $35k per lot.

    Frank Provance Diamond Realty

    0 Whitmore Brook Rd, Chester, VT 05143
    • /19

      Est $249,958 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft

      45 Dalrymple St, Chester, VT 05143

      45 Dalrymple St, Chester, VT 05143
  • /23

    $69,000

    • Land
    • 2.86 Acres
    • $24,126 per Acre

    58 Remington Rd, Chester, VT 05143

    Building lot with driveway and culverts in place, lot has preliminary site work complete including level grass land area, electrical transformer and 100 amp electrical power plus VTel fiber internet on lot for your new Vermont home. Home must be a minimun of 1,800 square feet of finished living space. Wastewater design and permits in place. A 16' x 25' garage/shed on lot for storage while

    John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
  • /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 $374,834 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,990 Sq Ft

      401 North St, Chester, VT 05143

      401 North St, 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
    • /28

      Est $413,274 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,152 Sq Ft

      250 North St, Chester, VT 05143

      250 North St, 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
  • /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
    • /39

      Est $371,430 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 2,090 Sq Ft

      312 North St, Chester, VT 05143

      312 North St, 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
  • /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
    • /37

      Est $679,415 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,325 Sq Ft

      332 Marcs Dr, Chester, VT 05143

      332 Marcs Dr, 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
  • /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
    • /40

      Est $597,625 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,564 Sq Ft

      498 Marcs Dr, Chester, VT 05143

      498 Marcs 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
  • /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
    • /10

      Est $353,044 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,214 Sq Ft

      784 Vt Route 103 N, Chester, VT 05143

      784 Vt Route 103 N, 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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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

Showing Results 81 - 120, Page 3 of 18

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