2,725

Windsor, VT Homes

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  • /44

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    663 Depot St, Chester, VT 05143

    Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

    Betsy Adamovich Real Broker LLC

    663 Depot St, Chester, VT 05143
  • /54

    $540,000 Sold May 23, 2025

    • 1,456 Sq Ft
    • $371/SF
    • 32 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    316 Little Pond Rd, Chester, VT 05143

    Charming Vermont Chalet for Sale in the township of Andover- 11.48 Private Acres near Ski Resorts & Lowell Lake State ParkExperience the best of rural character blended with the finest in modern amenities in this well-cared-for Vermont chalet. This charming retreat is ideal as a ski house, investment property, or full-time getaway.Inside, you’ll find an open-plan living space with vaulted

    Nick Sicard EXP Realty

    316 Little Pond Rd, Chester, VT 05143
    • /15

      Est $259,083 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft

      15 Breezy Ln, Chester, VT 05143

      15 Breezy Ln, Chester, VT 05143
  • /60

    $200,000

    • Land
    • 7 Acres
    • $30,166 per Acre

    00 Vermont 103, Andover, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Rachael Rogala Inc.

    00 Vermont 103, Andover, VT 05143
  • /60

    $400,000 Sold May 19, 2025

    • 2,960 Sq Ft
    • $135/SF
    • 166 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1844

    196 North St, Chester, VT 05143

    The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a

    Geralyn Donohue Engel & Völkers Okemo

    196 North St, Chester, VT 05143
    • /18

      Est $400,297 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,686 Sq Ft

      183 Pleasant St, Chester, VT 05143

      183 Pleasant St, Chester, VT 05143
  • /60

    $115,000

    • Land
    • 3.28 Acres
    • $35,061 per Acre

    00 Vt Route 103 N, Chester, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life.The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing.

    Rachael Rogala Rachael Rogala Inc.

    00 Vt Route 103 N, Chester, VT 05143
  • /40

    $640,000 Sold May 16, 2025

    • 2,752 Sq Ft
    • $233/SF
    • 113 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2024

    1873 Brockway Mills Rd, Chester, VT 05143

    This beautifully renovated 5-bedroom, 3-bathroom home offers a perfect blend of modern living and serene surroundings. Abuts over 2000 acres of undeveloped forest which offers direct access to the VAST trail system and unlimited hiking. With a large portion of the home newly built, it provides an expansive and updated interior featuring a spacious open-concept kitchen, dining, and living

    Heather Gleim CENTURY 21 North East

    1873 Brockway Mills Rd, Chester, VT 05143
    • /25

      Est $334,215 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,700 Sq Ft

      256 Depot St, Chester, VT 05143

      256 Depot St, Chester, VT 05143
  • /34

    $250,000

    • 1 Bed
    • 1 Bath
    • 617 Sq Ft

    413 Hidden Heights Rd, Chester, VT 05143

    Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

    Glenn Olney Barrett and Valley Associates Inc.

    413 Hidden Heights Rd, Chester, VT 05143
  • /48

    $412,000 Sold Apr 30, 2025

    • 1,990 Sq Ft
    • $207/SF
    • 142 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1895

    102 Church St, Chester, VT 05143

    A classic, easy maintenance four bedroom, two bath home in Chester village on .12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and

    Geralyn Donohue Engel & Völkers Okemo

    102 Church St, Chester, VT 05143
    • /26

      Est $391,688 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,382 Sq Ft

      73 Maple St, Chester, VT 05143

      73 Maple St, Chester, VT 05143
  • /60

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    442 Vermont 103, Chester, VT 05143

    Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

    Rachael Rogala Rachael Rogala Inc.

    442 Vermont 103, Chester, VT 05143
  • /52

    $1,850,000 Sold Apr 30, 2025

    • 3,779 Sq Ft
    • $490/SF
    • 220 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1972

    1328 Chandler Rd, Chester, VT 05143

    Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    1328 Chandler Rd, Chester, VT 05143
    • /36

      Est $541,108 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,664 Sq Ft

      191 Depot St, Chester, VT 05143

      191 Depot St, Chester, VT 05143
  • /19

    $379,900

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    302 Davidson Hill Rd, Chester, VT 05143

    This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

    Thaddeus Abare Barrett and Valley Associates Inc.

    302 Davidson Hill Rd, Chester, VT 05143
  • /43

    $400,000 Sold Apr 25, 2025

    • 1,800 Sq Ft
    • $222/SF
    • 106 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1984

    3057 Vermont 11, Chester, VT 05143

    Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high

    Geralyn Donohue Engel & Völkers Okemo

    3057 Vermont 11, Chester, VT 05143
    • /23

      Est $297,868 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,430 Sq Ft

      63 Highland Ct, Chester, VT 05143

      63 Highland Ct, Chester, VT 05143
  • /21

    $55,000

    • Land
    • 1.52 Acres
    • $36,184 per Acre

    0 Remington Rd Unit 5049900, Chester, VT 05143

    If you're dreaming of open skies, peaceful surroundings, and your own slice of Vermont, this property delivers. Just minutes from the charming Chester village green, this land offers the best of both worlds—seclusion and convenience. Step onto the property and take in the wide-open space surrounded by mature trees, offering privacy and natural beauty in every season. Whether you're envisioning

    Frank Provance Diamond Realty

    0 Remington Rd Unit 5049900, Chester, VT 05143
  • /2

    $330,000 Sold Apr 22, 2025

    • 2,008 Sq Ft
    • $164/SF
    • 318 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1850

    117 S Main St, Chester, VT 05143

    Opportunity awaits! This three-unit property has been very well maintained with 2 of the units being recently renovated and refreshed ready to be rented. The outside has recently been painted aswell and is ready to be owner occupied or rented out. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes

    Thaddeus Abare Barrett and Valley Associates Inc.

    117 S Main St, Chester, VT 05143
    • /30

      Est $379,848 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,442 Sq Ft

      64 Highland Ct, Chester, VT 05143

      64 Highland Ct, Chester, VT 05143
  • /20

    $85,000

    • Land
    • 1.82 Acres
    • $46,703 per Acre

    0 Remington Rd Unit 5049898, Chester, VT 05143

    Bring your plans and build your own piece of paradise! Just minutes from the iconic Chester town green, this scenic parcel offers the perfect blend of privacy, mountain views, and convenience. With a cleared, gently sloping build site already in place, this lot is ready for your imagination. Underground power is on site, and a well-crafted stone retaining wall, drilled well and septic components

    Frank Provance Diamond Realty

    0 Remington Rd Unit 5049898, Chester, VT 05143
  • /34

    $340,000 Sold Mar 27, 2025

    • 2,220 Sq Ft
    • $153/SF
    • 10 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1860

    489 Main St, Chester, VT 05143

    This beautifully renovated farmhouse offers a perfect mix of classic charm and modern updates, located just a short distance from the historic town green, shopping, and dining. The home features a spacious living room and cozy family room, providing plenty of space for both relaxation and entertainment. A dining area off the modern kitchen is perfect for family meals or hosting guests. The wood

    Gary Coger Four Seasons Sotheby's Int'l Realty

    489 Main St, Chester, VT 05143
    • /35

      Est $578,339 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,864 Sq Ft

      81 Main St, Chester, VT 05143

      81 Main St, Chester, VT 05143
  • /32

    $2,250,000

    • 2 Beds
    • 4 Baths
    • 2,410 Sq Ft

    611 Simmons Rd, Chester, VT 05143

    Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

    Dia Jenks LandVest, Inc/Woodstock

    611 Simmons Rd, Chester, VT 05143
  • /39

    $385,000 Sold Mar 20, 2025

    • 1,518 Sq Ft
    • $254/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    2240 Baltimore Rd, Chester, VT 05143

    Charming Vermont Retreat Near Okemo MountainNestled in the serene hills of Baltimore, Vermont, this welcoming property offers a perfect blend of privacy and proximity to outdoor adventure. Just a short drive to Okemo Mountain, this home is a nature lover’s dream.This well-maintained home features a thoughtful layout with a bedroom on each level, including a walkout basement that could serve as a

    Morriah Adams BHG Masiello Brattleboro

    2240 Baltimore Rd, Chester, VT 05143
    • /18

      Est $325,358 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,383 Sq Ft

      17 Orcutt Dr, Chester, VT 05143

      17 Orcutt Dr, Chester, VT 05143
  • /56

    $1,249,000

    • 4 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    157 Thompson Rd, Chester, VT 05143

    Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

    Joe Castaluccio Winhall Real Estate

    157 Thompson Rd, Chester, VT 05143
  • /26

    $270,000 Sold Feb 05, 2025

    • 1,005 Sq Ft
    • $269/SF
    • 0 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1988

    203 Marcs Dr, Chester, VT 05143

    Escape to this charming log cabin, tucked away on a quiet dead-end road. With an attached two-car garage and a small horse barn, this property is perfect for those seeking a blend of rustic charm and practicality. Inside, you’ll find a thoughtfully designed two-bedroom, one-bathroom layout with an airy open floor plan. The kitchen and living room flow seamlessly together, centered around a wood

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    203 Marcs Dr, Chester, VT 05143
    • /34

      Est $295,595 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,610 Sq Ft

      346 1st Ave, Chester, VT 05143

      346 1st Ave, Chester, VT 05143
  • /12

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    419 Coach Rd, Chester, VT 05143

    Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

    Amy Carson Lowe's Real Estate, LLC

    419 Coach Rd, Chester, VT 05143
  • /53

    $499,000 Sold Feb 03, 2025

    • 2,650 Sq Ft
    • $188/SF
    • 229 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1820

    566 Simonsville Rd, Chester, VT 05143

    The historic Jaquith House is located in the Andover settlement of Simonsville on Rte 11. This historical brick federal 3 bedroom, 2.5 bath home on 6.85 +/- acres has potential for either a vacation home with guest house, year round residence or investment property. The two story double-walled brick home has original features such as eyebrow windows and 3 chimneys and has been thoughtfully

    Geralyn Donohue Engel & Völkers Okemo

    566 Simonsville Rd, Chester, VT 05143
    • /28

      Est $253,457 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 943 Sq Ft

      386 1st Ave, Chester, VT 05143

      386 1st Ave, Chester, VT 05143
  • /26

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,327 Sq Ft

    160 Depot St, Chester, VT 05143

    Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

    Joshua Lemieux Remax Summit

    160 Depot St, Chester, VT 05143
  • /5

    $22,000 Sold Jan 31, 2025

    • Land
    • 3.28 Acres
    • $6,707 per Acre
    • 211 Days On Market

    0 Remington Rd Unit 9 4997325, Chester, VT 05143

    REUCDUED OVER $10,000.00, PRICED TO SELL! Lot #9 is one of the larger lots in the lower subdivision. It includes a pond that is maintained by the association with a fire hydrant to reduce insurance costs. Roughed in driveway and cleared building site make this a breeze to start construction. The lot is terraced with a nice buffer of trees for privacy. Come take a look today! PLEASE NOTE THERE

    Frank Provance Diamond Realty

    0 Remington Rd Unit 9 4997325, Chester, VT 05143
    • /40

      Est $470,108 Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 3,892 Sq Ft

      595 Main St, Chester, VT 05143

      595 Main St, Chester, VT 05143
  • /15

    $129,000

    • Land
    • 3.24 Acres
    • $39,815 per Acre

    Lot 3 Mattson Rd, Chester, VT 05143

    Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion.As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out

    Jessica Citera Cummings & Co

    Lot 3 Mattson Rd, Chester, VT 05143
  • /6

    $23,000 Sold Jan 31, 2025

    • Land
    • 1.64 Acres
    • $14,024 per Acre
    • 215 Days On Market

    0 Remington Rd Unit 8 4996410, Chester, VT 05143

    REUCDUED $10,000.00 PRICED TO SELL! Just a mile to the quintessential downtown of Chester is this beautiful lot in the Remington subdivision. This 1.64 acre lot has exceptional views! The terraced lot is ideal for a walk out lower level to a what could be a flat lush lawn with fire pit, swing set, horseshoe pits or all of the above! This is a great value with a million dollar view! Under

    Frank Provance Diamond Realty

    0 Remington Rd Unit 8 4996410, Chester, VT 05143
    • /24

      Est $567,630 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,622 Sq Ft

      548 Main St, Chester, VT 05143

      548 Main St, Chester, VT 05143
  • /30

    $650,000

    • 3 Beds
    • 3 Baths
    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, Chester, VT 05143

Showing Results 41 - 80, Page 2 of 18

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