2,743

Chester, VT Homes

Section Image
  • /53

    $550,000

    Sold Oct 06, 2025

    1937 Green Mountain Turnpike, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 1,812 Sq Ft
    • Built 1864

    Last Sold Summary

    • 3% Below List Price
    • $304/SF
    • 6 Days On Market

    Current Estimated Value $557,790

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
    • /37

      Est $650,249

      Not Listed For Sale

      332 Marcs Dr, Chester, VT 05143

      • 4 Beds
      • 3.5 Baths
      • 2,795 Sq Ft
      • Built 1988
      332 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

  • /31

    $349,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    1397 Popple Dungeon Rd, Chester, VT 05143

    Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved

    Daire Gibney Barrett and Valley Associates Inc.

    1397 Popple Dungeon Rd, Chester, VT 05143
  • /2

    $421,833

    Sold Jul 10, 2025

    332 Hidden Heights Rd, Chester, VT 05143

    • 4 Beds
    • 2.5 Baths
    • 2,868 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $147/SF
    • 50 Days On Market

    Current Estimated Value $503,985

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    332 Hidden Heights Rd, Chester, VT 05143
    • /40

      Est $231,360

      Not Listed For Sale

      244 Main St, Chester, VT 05143

      • 7 Beds
      • 8 Baths
      • 4,475 Sq Ft
      • Built 1825
      244 Main St, Chester, VT 05143

      Last Sold Summary

      • 70 Days On Market

  • /14

    $87,500

    • Land
    • 10.4 Acres
    • $8,413 per Acre

    00 Snell Rd, Chester, VT 05143

    CHESTER 10.4+/- acre parcel of land offers offers 180 degree ridgeline views with clearing from an elevated plateau for either a house site or a camp site with a home closer to the town maintained road. A nice stream meanders through the property which is dotted with large rocks and stone walls. There is 245 ft. of frontage on Snell Road and utility pole at the road. Close to Okemo and Magic

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Snell Rd, Chester, VT 05143
  • /10

    $129,000

    Sold Feb 24, 2026

    469 Williams Rd, Chester, VT 05143

    • Land
    • 10.88 Acres
    • $11,857 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $129,687

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
    • /39

      Est $415,046

      Not Listed For Sale

      160 Peck Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,068 Sq Ft
      • Built 1925
      160 Peck Rd, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

  • /30

    $650,000

    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VT Discover 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 meticulously

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, Chester, VT 05143
  • /20

    $250,000

    Sold Jun 30, 2026

    202 Mountain View, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,140 Sq Ft
    • Built 1945

    Last Sold Summary

    • $219/SF
    • 5 Days On Market

    Current Estimated Value $246,118

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    202 Mountain View, Chester, VT 05143
    • /34

      Est $911,536

      Not Listed For Sale

      835 Quarry Rd, Chester, VT 05143

      • 3 Beds
      • 4 Baths
      • 2,221 Sq Ft
      • Built 1998
      835 Quarry Rd, Chester, VT 05143

      Last Sold Summary

      • 4 Days On Market

  • /32

    $153,000

    • Land
    • 4.7 Acres
    • $32,553 per Acre

    250 Fenton Rd, Chester, VT 05143

    Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the

    Rachel Febbie EXP Realty

    250 Fenton Rd, Chester, VT 05143
  • /16

    $205,000

    Sold Apr 10, 2026

    1876 Popple Dungeon Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $166/SF
    • 6 Days On Market

    Current Estimated Value $206,898

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1876 Popple Dungeon Rd, Chester, VT 05143
    • /59

      Est $561,752

      Not Listed For Sale

      50 Howard Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,728 Sq Ft
      • Built 1986
      50 Howard Rd, Chester, VT 05143

      Last Sold Summary

      • 27 Days On Market

  • /22

    $279,000

    • 5 Beds
    • 3 Baths
    • 1,812 Sq Ft

    2100 Baltimore Rd, Chester, VT 05143

    COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, & ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF

    Don Chabot Town and Country Realty

    2100 Baltimore Rd, Chester, VT 05143
  • /56

    $402,239

    Sold Nov 12, 2025

    4877 Vt Route 103 N, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1980

    Last Sold Summary

    • 10% Below List Price
    • $233/SF
    • 10 Days On Market

    Current Estimated Value $441,953

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
    • /33

      Est $643,046

      Not Listed For Sale

      50 Goldthwaite Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,214 Sq Ft
      • Built 1987
      50 Goldthwaite Rd, Chester, VT 05143

      Last Sold Summary

      • 27 Days On Market

  • /60

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,204 Sq Ft

    168 Chandler Rd, Chester, VT 05143

    Welcome to your private gated mini-estate—an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet

    Diane Rousseau Four Seasons Sotheby's Int'l Realty

    168 Chandler Rd, Chester, VT 05143
  • /48

    $825,000

    Sold Apr 09, 2026

    1269 Howard Hill Rd, Chester, VT 05143

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft
    • Built 2024

    Last Sold Summary

    • 8% Below List Price
    • $380/SF
    • 55 Days On Market

    Current Estimated Value $824,804

    Last Listing Agent Cheyanne Pugliese

    1269 Howard Hill Rd, Chester, VT 05143
    • /19

      Est $210,589

      Not Listed For Sale

      83 Potash Brook Rd, Chester, VT 05143

      • 2 Beds
      • 500 Sq Ft
      • Built 1970
      83 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 211 Days On Market

  • /53

    $1,490,000

    Open Sun 11AM - 2PM $200K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 5,400 Sq Ft

    1302 Popple Dungeon Rd, Chester, VT 05143

    Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details—wide-plank wood floors, paneled walls,

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1302 Popple Dungeon Rd, Chester, VT 05143
  • /47

    $1,375,000

    Sold Sep 30, 2025

    465 Pennell Rd, Chester, VT 05143

    • 4 Beds
    • 4.5 Baths
    • 5,700 Sq Ft
    • Built 1967

    Last Sold Summary

    • 8% Below List Price
    • $241/SF
    • 20 Days On Market

    Current Estimated Value $1,335,715

    Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty

    465 Pennell Rd, Chester, VT 05143
    • /26

      Est $343,841

      Not Listed For Sale

      154 Fletcher Hill Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft
      • Built 1979
      154 Fletcher Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 52 Days On Market

  • /60

    $495,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    3078 Vt Route 10, Chester, VT 05143

    This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached

    Tyleen Murray Kelley Real Estate, Inc.

    3078 Vt Route 10, Chester, VT 05143
  • /2

    $70,000

    Sold Oct 21, 2025

    Lot 2 Old Stage Rd, Chester, VT 05143

    • Land
    • 6.3 Acres
    • $11,111 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 35 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    Lot 2 Old Stage Rd, Chester, VT 05143
    • /43

      Est $404,103

      Not Listed For Sale

      3057 Vt Route 11 E, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,800 Sq Ft
      • Built 1984
      3057 Vt Route 11 E, Chester, VT 05143

      Last Sold Summary

      • 106 Days On Market

  • /60

    $549,000

    $40K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 2,016 Sq Ft

    35 Upper Bartonsville Rd, Chester, VT 05143

    Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

    Erin Kendall EXP Realty

    35 Upper Bartonsville Rd, Chester, VT 05143
  • /53

    $569,000

    Sold Jun 17, 2026

    147 Pleasantview Ln, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 2,966 Sq Ft
    • Built 1993

    Last Sold Summary

    • 4% Below List Price
    • $192/SF
    • 27 Days On Market

    Current Estimated Value $590,469

    Last Listing Agent Jay Farrar Four Seasons Sotheby's Int'l Realty

    147 Pleasantview Ln, Chester, VT 05143
    • /24

      Est $287,204

      Not Listed For Sale

      1369 Flamstead Rd, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,096 Sq Ft
      • Built 1973
      1369 Flamstead Rd, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

  • /20

    $449,000

    Under Contract
    • 5 Beds
    • 1 Bath
    • 2,856 Sq Ft

    127 Trombley Rd, Chester, VT 05143

    Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a

    Daire Gibney Barrett and Valley Associates Inc.

    127 Trombley Rd, Chester, VT 05143
  • /2

    $165,000

    Sold Oct 23, 2025

    1436 Route 103, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 1825

    Last Sold Summary

    • 4% Above List Price
    • $107/SF
    • 2 Days On Market

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1436 Route 103, Chester, VT 05143
    • /40

      Est $634,618

      Not Listed For Sale

      1573 Trebo Rd, Chester, VT 05143

      • 2 Beds
      • 2.5 Baths
      • 1,444 Sq Ft
      • Built 1988
      1573 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

  • /34

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft

    3208 Green Mountain Turnpike, Chester, VT 05143

    Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    3208 Green Mountain Turnpike, Chester, VT 05143
  • /36

    $425,000

    Sold Jul 30, 2025

    115 Orcutt Dr, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,360 Sq Ft
    • Built 1955

    Last Sold Summary

    • $312/SF
    • 26 Days On Market

    Current Estimated Value $439,039

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    115 Orcutt Dr, Chester, VT 05143
    • /13

      Not Listed For Sale

      28 Mineral Spring Rd, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 852 Sq Ft
      • Built 1993
      28 Mineral Spring Rd, Chester, VT 05143

      Last Sold Summary

      • 27 Days On Market

  • /12

    $120,000

    • Land
    • 3.24 Acres
    • $37,037 per Acre

    508 Mattson Rd, Chester, VT 05143

    This property offers so many possibilities! 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

    Jessica Citera Cummings & Co

    508 Mattson Rd, Chester, VT 05143
  • /60

    $815,000

    Sold Feb 13, 2026

    810 Quarry Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,466 Sq Ft
    • Built 2006

    Last Sold Summary

    • $330/SF
    • 4 Days On Market

    Current Estimated Value $822,334

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    810 Quarry Rd, Chester, VT 05143
    • /38

      Est $319,970

      Not Listed For Sale

      616 Mattson Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,349 Sq Ft
      • Built 1940
      616 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 119 Days On Market

  • /38

    $249,500

    • 4 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    3668 Vt Route 103 N, Chester, VT 05143

    Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

    Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

    3668 Vt Route 103 N, Chester, VT 05143
  • /2

    $350,000

    Sold Nov 09, 2025

    491 Farrar Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft
    • Built 1990

    Last Sold Summary

    • 12% Below List Price
    • $129/SF
    • 123 Days On Market

    Current Estimated Value $365,931

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143

Showing Results 81 - 120, Page 3 of 18

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