2,724

Windsor, VT Homes

Section Image
  • 95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    /52

    $667,500

    • 4 Beds
    • 3 Baths
    • 2,794 Sq Ft

    95 Church St, Chester, VT 05143

    Charming Renovated Farmhouse in the Heart of ChesterThis beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway.Inside, enjoy a spacious kitchen with custom

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    95 Church St, Chester, VT 05143
  • 2940 Vt Rt 10, Chester, VT 05143
    2940 Vt Rt 10, Chester, VT 05143
    2940 Vt Rt 10, Chester, VT 05143
    /13

    $1,600 per month

    • 2 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Apartment for Rent

    2940 Vt Rt 10, Chester, VT 05143

    Completely renovated country living whole house apartment. Livingroom, kitchen with step up dining area, bonus room for office/craft area and a full bath with washer/dryer all on the first floor. Master bedroom with walk in closet and 2nd bedroom on the upper floor. $1,600.00 per month plus all utilities. Application, references, and credit check required for approval. One year lease agreement

    Team BVA Rentals Barrett and Valley Associates Inc.

    2940 Vt Rt 10, Chester, VT 05143
  • 358 Maple Ridge Rd, Chester, VT 05143
    358 Maple Ridge Rd, Chester, VT 05143
    358 Maple Ridge Rd, Chester, VT 05143
    /16

    $285,000 Sold Jul 31, 2025

    • 988 Sq Ft
    • $288/SF
    • 2 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1989

    358 Maple Ridge Rd, Chester, VT 05143

    This two-bedroom, plus children's loft, is located on 2.1, open and wooded, acres on a dead-end road. It blends seclusion and privacy and is only fifteen minutes to the resort town of Ludlow. House, also, features vinyl siding with a separate, insulated two-car garage. This is a MUST SEE!!

    Gale Alger Alger Real Estate Agency

    358 Maple Ridge Rd, Chester, VT 05143
    • Lot 6 Jillie Ln, Chester, VT 05143
      Lot 6 Jillie Ln, Chester, VT 05143
      Lot 6 Jillie Ln, Chester, VT 05143
      /10

      Not Listed For Sale

      Lot 6 Jillie Ln, Chester, VT 05143

      Lot 6 Jillie Ln, Chester, VT 05143
  • 725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    /58

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 2,544 Sq Ft

    725 Flamstead Rd, Chester, VT 05143

    Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities

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

    725 Flamstead Rd, Chester, VT 05143
  • 2940 Vt Route 10 Unit B, Chester, VT 05143
    2940 Vt Route 10 Unit B, Chester, VT 05143
    2940 Vt Route 10 Unit B, Chester, VT 05143
    /3

    $950 per month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Apartment for Rent

    2940 Vt Route 10 Unit B, Chester, VT 05143

    Cozy second floor one bedroom / full bath apartment available. Tenant pays heat, electric and wifi. Landlord pays lawncare, plowing and rubbish removal.$950.00 per month. Application, references, and credit check required for approval. One year lease agreement with 1st, last and security deposit required before move in.

    Team BVA Rentals Barrett and Valley Associates Inc.

    2940 Vt Route 10 Unit B, Chester, VT 05143
  • 387 Weston-Andover Rd, Chester, VT 05143
    387 Weston-Andover Rd, Chester, VT 05143
    387 Weston-Andover Rd, Chester, VT 05143
    /57

    $399,000 Sold Jul 31, 2025

    • 1,080 Sq Ft
    • $369/SF
    • 77 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    387 Weston-Andover Rd, Chester, VT 05143

    Nestled on a peaceful hillside in the town of Andover, this well-maintained home offers the soothing sounds of the Andover Branch River as your daily backdrop. Enjoy the ease of one-level living with three bedrooms, a full bathroom, and a comfortable main living space perfect for relaxing or entertaining.The walkout basement adds even more potential. Already underway is a second full

    Jessica Citera Cummings & Co

    387 Weston-Andover Rd, Chester, VT 05143
    • 0 Hillcrest Dr, Chester, VT 05143
      0 Hillcrest Dr, Chester, VT 05143
      0 Hillcrest Dr, Chester, VT 05143
      /8

      Not Listed For Sale

      • 3 Beds

      0 Hillcrest Dr, Chester, VT 05143

      0 Hillcrest Dr, Chester, VT 05143
  • 656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    /55

    $649,000

    • 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
  • 117 S Main St Unit 3, Chester, VT 05143
    117 S Main St Unit 3, Chester, VT 05143
    117 S Main St Unit 3, Chester, VT 05143
    /7

    $1,200 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    117 S Main St Unit 3, Chester, VT 05143

    This 2nd floor roomy apartment is nicely updated. Enjoy the spacious kitchen and dining room combination. A living room, bedroom, bath and plenty of storage within the apartment completing the space. A coin-op washer/dryer on site for tenant use. Plenty of off street parking. The apartment is within walking distance to most town conveniences. Heat, water/sewer, rubbish removal, plowing and mowing

    Team BVA Rentals Barrett and Valley Associates Inc.

    117 S Main St Unit 3, Chester, VT 05143
  • 442 Elm St, Chester, VT 05143
    442 Elm St, Chester, VT 05143
    442 Elm St, Chester, VT 05143
    /27

    $259,000 Sold Jul 31, 2025

    • 1,488 Sq Ft
    • $174/SF
    • 126 Days On Market
    • Built 1950

    442 Elm St, Chester, VT 05143

    Terrific in town property is being offered! Two units in one building! One unit offers one bedroom and 3/4 bath open concept living and kitchen area. Second unit offers two bedrooms, living room, 3/4 bath and updated kitchen! Walk to amenities in Chester Depot including of course the train, Smitty's market and salon! Chester village less than one mile away as well.

    Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
    • 3089 Vt Route 11 W, Chester, VT 05143
      3089 Vt Route 11 W, Chester, VT 05143
      3089 Vt Route 11 W, Chester, VT 05143
      /38

      Est $232,588 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,732 Sq Ft

      3089 Vt Route 11 W, Chester, VT 05143

      3089 Vt Route 11 W, Chester, VT 05143
  • 525 Route 103 N, Chester, VT 05143
    525 Route 103 N, Chester, VT 05143
    525 Route 103 N, Chester, VT 05143
    /60

    $495,000

    • 6 Beds
    • 1 Bath
    • 2,308 Sq Ft

    525 Route 103 N, Chester, VT 05143

    The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

    Glenn Olney Barrett and Valley Associates Inc.

    525 Route 103 N, Chester, VT 05143
  • 479 Main St, Chester, VT 05143
    479 Main St, Chester, VT 05143
    479 Main St, Chester, VT 05143
    /7

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Apartment for Rent

    479 Main St, Chester, VT 05143

    UNIQUE SEASONAL RENTAL!!Located in the village of Chester. A short distance to several ski resorts and all conveniences. This beautiful apartment has a cozy cottage feel with its post and beam look and airy vaulted ceiling. Livingroom/Diningroom combo, Kitchen, Bedroom, Loft and 2 baths. All inclusive for $2,800.00 per month. Credit check and references required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    479 Main St, Chester, VT 05143
  • 115 Orcutt Dr, Chester, VT 05143
    115 Orcutt Dr, Chester, VT 05143
    115 Orcutt Dr, Chester, VT 05143
    /36

    $425,000 Sold Jul 30, 2025

    • 1,360 Sq Ft
    • $312/SF
    • 26 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    115 Orcutt Dr, Chester, VT 05143

    This charming village home in Chester, located on a peaceful dead-end street, offers a fantastic blend of comfort and convenience. The house has been meticulously maintained both inside and out. It boasts a spacious double lot with beautiful gardens and fruit trees. Inside, you'll find two bedrooms plus a versatile den, providing ample living space. The kitchen has been doubled in size with walls

    Joseph Karl William Raveis Real Estate Vermont Properties

    115 Orcutt Dr, Chester, VT 05143
    • 35 Depot St, Chester, VT 05143
      35 Depot St, Chester, VT 05143
      35 Depot St, Chester, VT 05143
      /17

      Est $80,894 Not Listed For Sale

      • 4 Beds

      35 Depot St, Chester, VT 05143

      35 Depot St, Chester, VT 05143
  • 1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    /56

    $599,999

    • 5 Beds
    • 3.5 Baths
    • 2,443 Sq Ft

    1057 Quarry Rd, Chester, VT 05143

    Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

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

    1057 Quarry Rd, Chester, VT 05143
  • 186 Mountain View, Chester, VT 05143
    186 Mountain View, Chester, VT 05143
    /2

    $250,000 Sold Jul 16, 2025

    • 966 Sq Ft
    • $259/SF
    • 40 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1942

    186 Mountain View, Chester, VT 05143

    This Charming, well appointed home has much to offer! This turn key home is tucked away in a great location and neighborhood in walking distance to shops, food options and schools. The home itself has been updated and features many positives like almost all double pane windows, a recently redone paved driveway, an updated mudroom area, a metal standing seam roof, and much more. With a good size

    Thaddeus Abare Barrett and Valley Associates Inc.

    186 Mountain View, Chester, VT 05143
    • 141 Stage, Chester, VT 05143
      141 Stage, Chester, VT 05143
      141 Stage, Chester, VT 05143
      /36

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 924 Sq Ft

      141 Stage, Chester, VT 05143

      141 Stage, Chester, VT 05143
  • 2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    /52

    $627,500

    • 3 Beds
    • 2.5 Baths
    • 1,868 Sq Ft

    2510 E Hill Rd, Chester, VT 05143

    This home on East Hill Road commands one of the area's best views all the way to Stratton! It is one of those spots where the view is different every day & spectacular! The home sits on 14 acres & it overlooks land protected by the Vermont Land Trust and mountains beyond. From the moment you enter, you won't want to leave. It is immaculate and ready to go. A large mudroom with a slate floor &

    Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
  • 0 Hall Rd, Chester, VT 05143
    0 Hall Rd, Chester, VT 05143
    0 Hall Rd, Chester, VT 05143
    /19

    $85,000 Sold Jul 16, 2025

    • Land
    • 47 Acres
    • $1,817 per Acre
    • 195 Days On Market

    0 Hall Rd, Chester, VT 05143

    Private and secluded 46.77 acre wooded lot in Chester, VT.Property is in the current use program.The east side of the property runs along the Chester/Springfield line.15 minutes to I-91 and within driving distance to Okemo, Stratton, Magic & Bromley Ski Mountains.There is a slight view on the north east side of the property. There is a deeded ROW that is not maintained. This lot

    Jessica Samples BHG Masiello Keene

    0 Hall Rd, Chester, VT 05143
    • 00 Trebo Rd, Chester, VT 05143
      00 Trebo Rd, Chester, VT 05143
      00 Trebo Rd, Chester, VT 05143
      /5

      Not Listed For Sale

      00 Trebo Rd, Chester, VT 05143

      00 Trebo Rd, Chester, VT 05143
  • 350 Farrar Rd, Chester, VT 05143
    350 Farrar Rd, Chester, VT 05143
    350 Farrar Rd, Chester, VT 05143
    /31

    $599,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    350 Farrar Rd, Chester, VT 05143

    ~Price correction~ Looking for a peaceful escape with plenty of space to spread out? This inviting home sits on a quiet dirt road, just minutes from the heart of Chester Village and close to all the best things Vermont has to offer—skiing, hiking, swimming, and more. This property is perfect as a Primary home, vacation home or can be used as a short-term rental.Inside, there’s tons of

    Linda Benoit Highland Realty

    350 Farrar Rd, Chester, VT 05143
  • 270 North St, Chester, VT 05143
    270 North St, Chester, VT 05143
    270 North St, Chester, VT 05143
    /58

    $373,000 Sold Jul 10, 2025

    • 2,919 Sq Ft
    • $128/SF
    • 61 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1810

    270 North St, Chester, VT 05143

    Nestled in one of Vermont’s historic locations, Chester’s Stone Village offers timeless charm and rich character. This classic Federal-style home—featuring brick ends and a clapboard front—could be your next residence or vacation retreat. While this brick sided inviting 4-bedroom, 2-bath home isn’t built of stone, it belongs to a rare collection of nine homes and a church constructed in the 1830s

    Joseph Karl William Raveis Real Estate Vermont Properties

    270 North St, Chester, VT 05143
    • 00 Vt Route 11 W, Chester, VT 05143
      00 Vt Route 11 W, Chester, VT 05143
      00 Vt Route 11 W, Chester, VT 05143
      /6

      Not Listed For Sale

      00 Vt Route 11 W, Chester, VT 05143

      00 Vt Route 11 W, Chester, VT 05143
  • 1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon Rd, Chester, VT 05143
    /59

    $1,125,000 Pending

    • 3 Beds
    • 4 Baths
    • 3,739 Sq Ft

    1502 Popple Dungeon Rd, Chester, VT 05143

    Welcome to paradise! Enjoy all four seasons in this handsome, 1989 colonial-style home with modern amenities. From the covered porch, relax and take in views of the front gardens and your land across the road with apple trees and brook frontage. A large solar array is tucked out of sight producing all the power you would need. Behind the house is a fenced-in garden and greenhouse, a couple of

    Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
  • 332 Hidden Heights Rd, Chester, VT 05143
    332 Hidden Heights Rd, Chester, VT 05143
    /2

    $421,833 Sold Jul 10, 2025

    • 2,068 Sq Ft
    • $204/SF
    • 50 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    332 Hidden Heights Rd, Chester, VT 05143

    This charming multi-level home provides 4 bedrooms and a variety of places to find private space for quiet. Also a large open recreation room which includes a full size pool table/table tennis table and dry bar. Located just 3 miles from the charming Town of Chester. An easy drive to Bromley Mt, Magic Mt and Okemo, this makes a great home for an active family. Beautiful views from the deck

    John Tolosky Barrett and Valley Associates Inc.

    332 Hidden Heights Rd, Chester, VT 05143
    • 1709 Potash Brook Rd, Chester, VT 05143
      1709 Potash Brook Rd, Chester, VT 05143
      1709 Potash Brook Rd, Chester, VT 05143
      /4

      Est $565,204 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,688 Sq Ft

      1709 Potash Brook Rd, Chester, VT 05143

      1709 Potash Brook Rd, Chester, VT 05143
  • 3236 Weston-Andover Rd, Chester, VT 05143
    3236 Weston-Andover Rd, Chester, VT 05143
    3236 Weston-Andover Rd, Chester, VT 05143
    /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
  • 198 Coach Rd, Chester, VT 05143
    198 Coach Rd, 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
    • 201 Spruce Dr, Chester, VT 05143
      201 Spruce Dr, Chester, VT 05143
      201 Spruce Dr, Chester, VT 05143
      /40

      Est $713,843 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,670 Sq Ft

      201 Spruce Dr, Chester, VT 05143

      201 Spruce Dr, Chester, VT 05143
  • 31 Palmer Rd, Chester, VT 05143
    31 Palmer Rd, Chester, VT 05143
    31 Palmer 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
  • 206 Cummings Rd, Chester, VT 05143
    206 Cummings 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
    • 418 1st Ave, Chester, VT 05143
      418 1st Ave, Chester, VT 05143
      418 1st Ave, Chester, VT 05143
      /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
  • 534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    /60

    $599,000 Under Contract

    • 7 Beds
    • 3.5 Baths
    • 3,850 Sq Ft

    534 Elm St, Chester, VT 05143

    Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal

    Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
  • 218 Gunderson Rd, Chester, VT 05143
    218 Gunderson Rd, Chester, VT 05143
    218 Gunderson Rd, 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
    • 184 Kevadus Cir, Chester, VT 05143
      184 Kevadus Cir, Chester, VT 05143
      184 Kevadus Cir, Chester, VT 05143
      /14

      Est $262,211 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      184 Kevadus Cir, Chester, VT 05143

      184 Kevadus Cir, Chester, VT 05143
  • 472 Main St, Chester, VT 05143
    472 Main St, Chester, VT 05143
    472 Main St, Chester, VT 05143
    /60

    $499,000 Under Contract

    • 5 Beds
    • 7 Baths
    • 5,546 Sq Ft

    472 Main St, Chester, VT 05143

    The Laurin Whiting House, circa 1850, is a Greek Revival style home with 5 bedrooms and 7 baths on 1 +/- acre. The curved, multi-bay veranda wraps around the front of the house with neo-classical columns and an oculus that punctuates the front gable end. A light-filled living room has French doors that open to the lovely porch and adjoin a large bedroom and full bath. The formal dining room

    Geralyn Donohue Engel & Völkers Okemo

    472 Main St, Chester, VT 05143
  • 3590 Vt 103, Chester, VT 05143
    3590 Vt 103, Chester, VT 05143
    3590 Vt 103, Chester, VT 05143
    /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
    • 165 Vt Route 103 S, Chester, VT 05143
      165 Vt Route 103 S, Chester, VT 05143
      165 Vt Route 103 S, Chester, VT 05143
      /40

      Est $219,614 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

Showing Results 1 - 40, Page 1 of 18

Vermont Windsor County Chester

Real Estate & Homes

Home Trends in Chester, VT

On average, homes in Chester, VT sell after 65 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, VT over the last 12 months is $295,000, down 51% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$295,000
Median Single Family Sale Price
$495,000
Average Price Per Sq Ft
$260
Number of Homes for Sale
3
Last 12 months Home Sales
24
Months of Supply
1.50
Median List Price
$595,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-51%
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