Windsor, VT Homes in ZIP Code 05143

• 

  

  

  /29

  $875,000

  • Land
  • 67 Acres
  • $12,982 per Acre

  00 Markham Ln, Weston, VT 05161

  An exceptional Weston land parcel with panoramic views, this property has been family land for generations and is now being offered for sale. A long tree-lined private drive slopes through forest to a cleared, sunny 4-acre field prepared for a house site. The site's elevation at almost 1800 feet backs onto forest and reveals stunning four-season views of the Green Mountain range, rolling hills,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  00 Markham Ln, Weston, VT 05161
• 

  

  

  /29

  $543,000 Sold Jul 08, 2025

  • 2,185 Sq Ft
  • $249/SF
  • 38 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1969

  35 Markham Ln, Weston, VT 05161

  Tucked above the historic village of Weston, this charming Cape-style home offers a serene retreat on 3.5 private acres. Wood beams bring authentic charm to the newly renovated kitchen. The residence features a spacious Great Room with vaulted ceilings and a Jotul wood stove, perfect for entertaining or quiet nights at home. The main level includes two bedrooms and a full bath, while the upper

  Christiane Carroccio TPW Real Estate

  35 Markham Ln, Weston, VT 05161
• 

  

  

  /29

  Est $298,958 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,477 Sq Ft

  418 1st Ave, Chester, VT 05143

  418 1st Ave, Chester, VT 05143
• 

  

  

  /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
• 

  

  /2

  $350,000 Sold Jun 25, 2025

  • 1,584 Sq Ft
  • $221/SF
  • 82 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1987

  198 Coach Rd, Chester, VT 05143

  Imagine a home so inviting and comfortable, you'd never want to leave. Welcome to this practical and low-maintenance ranch-style home, perfectly designed for both relaxation and entertainment. Step inside and be greeted by the beautifully updated living room, bathed in natural light and warmed by a cozy wood stove—a haven during those chilly Vermont winters.This house isn't just a place to live;

  Daire Gibney Barrett and Valley Associates Inc.

  198 Coach Rd, Chester, VT 05143
• 

  

  /32

  Est $494,413 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  15 Markham Ln, Weston, VT 05161

  15 Markham Ln, Weston, VT 05161
• 

  

  /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
• 

  

  /59

  $280,000 Sold Jun 24, 2025

  • 1,134 Sq Ft
  • $247/SF
  • 473 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1983

  87 Trombley Rd, Andover, VT 05143

  Looking for privacy and a peaceful piece of Vermont, high on a hill, to call your own? Look no further than this 17+ beautiful acres at the dead end of a private road. Already in place is a 2 bedroom, 1 bathroom manufactured home with power, septic (it is already in place for a 3 bedroom house), and a drilled well. Live in the home already in place or just stay in it while you build your dream

  Erin Kendall EXP Realty

  87 Trombley Rd, Andover, VT 05143
• 

  

  /14

  Est $285,187 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  184 Kevadus Cir, Chester, VT 05143

  184 Kevadus Cir, 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
• 

  

  /13

  $80,000 Sold Jun 05, 2025

  • 556 Sq Ft
  • $144/SF
  • 166 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1940

  64 County Rd, North Springfield, VT 05150

  BACK ON THE MARKET AT NO FAULT OF THE PROPERTY. Older cottage in need of a total re-hab is waiting for you. Would make a great vacation home or seasonal home or a cute little home for one or two people. Standing seam roof, built on an accessible crawl space. There is an old barn on the property for storage as well. This home will NOT qualify for financing, so we are looking for a cash buyer

  Julie Buffum Buffum Realty

  64 County Rd, North Springfield, VT 05150
• 

  

  /40

  Est $227,760 Not Listed For Sale

  • 6 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  165 Vt Route 103 S, Chester, VT 05143

  165 Vt Route 103 S, Chester, VT 05143
• 

  

  /34

  $210,000

  • 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
• 

  /2

  $30,000 Sold Jun 04, 2025

  • Land
  • 0.50 Acre
  • $60,000 per Acre

  • 208 Days On Market

  206 Cummings Rd, Chester, VT 05143

  This Property features a mostly level lot with a cottage situated above the road in a private, yet easily accessed and convenient location. It is just walking distance from Chester Depot and the Chester Village Green.Currently there is no septic or well, it may appeal as a great camping spot in the beginning. It might just become the perfect location to develop, as a full time place to be!

  Thaddeus Abare Barrett and Valley Associates Inc.

  206 Cummings 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

  $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
• 

  

  /50

  $950,000 Sold May 30, 2025

  • 3,175 Sq Ft
  • $299/SF
  • 263 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1907

  218 Gunderson Rd, Chester, VT 05143

  This quintessential 4 bedroom (with a septic permit for up to 5 bedrooms)/2.5 bathroom farmhouse, fully renovated and absolutely gorgeous, is perched on a grassy knoll overlooking 32 acres of rolling meadow, hardwood forest and private pond. The modern touches that are essential for today's style of living pair perfectly with the warmth and charm of an old farmhouse. The house was renovated in

  Joseph Karl William Raveis Real Estate Vermont Properties

  218 Gunderson Rd, 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
• 

  

  /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
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  /26

  $311,688 Sold May 30, 2025

  • 2,702 Sq Ft
  • $115/SF
  • 387 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  3590 Vt 103, Chester, VT 05143

  Fully furnished! Thoughtfully upgraded home on .89 acres located in the beautiful area of Gassetts in Chester, Vermont. Easy access to I-91, 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. This three bedroom, two bathroom home has an open concept. Two bedrooms on the second floor and one bedroom

  Jessica Samples BHG Masiello Keene

  3590 Vt 103, 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
• 

  

  /25

  $359,000

  • 3 Beds
  • 1,504 Sq Ft

  1749 Middletown Rd, Andover, VT 05143

  Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1749 Middletown Rd, Andover, 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
• 

  

  /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
• 

  

  /15

  $94,500

  • Land
  • 4.05 Acres
  • $23,333 per Acre

  00 Hillcrest Dr, Andover, VT 05143

  Ready to Build in Southern Vermont!Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for

  Daire Gibney Barrett and Valley Associates Inc.

  00 Hillcrest Dr, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /37

  $600,000 Sold May 09, 2025

  • 2,076 Sq Ft
  • $289/SF
  • 575 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2008

  43 Lee Way, Andover, VT 05143

  Turn-key and Central to 4 ski areas, this beautifully renovated Cape sits on 10.5 acres with picturesque views. You'll enjoy the location just 20 minutes to Stratton, Okemo and Bromley. But most importantly, you'll appreciate the new fit and finish: new wood flooring, stone faced hearth, new Kitchenaid appliance package, interior painting and lighting. And it doesn't stop there, new gravel

  Britt Wohler Wohler Realty Group

  43 Lee Way, Andover, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /12

  $239,000

  • 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

Showing Results 41 - 80, Page 2 of 18