2,599

Chester, VT Homes

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  • /12

    $149,000

    • Land
    • 17.7 Acres
    • $8,418 per Acre

    0 Trebo Rd, Chester, VT 05143

    Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont

    Agent Photo

    Gail Beardmore

    Engel & Völkers Okemo

    0 Trebo Rd, Chester, VT 05143
  • /17

    $3,000

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • House for Rent

    96 S Main St, Chester, VT 05143

    Spacious 4-Bedroom Home with Large Backyard in the Heart of Chester, VT.Welcome to 96 S Main St — a charming and well-appointed 4-bedroom, 2.5-bath home offering 2,215 square feet of comfortable living space in the very heart of Chester village.Inside, you’ll find a bright and generous living room and dining room perfect for relaxing or entertaining, a functional kitchen with all

    96 S Main St, Chester, VT 05143
  • /42

    $415,000

    Sold Mar 30, 2026

    1979 N Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $222/SF
    • 113 Days On Market

    Current Estimated Value $393,500

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    1979 N Hill Rd, Chester, VT 05143
    • /59

      Est $927,919

      Not Listed For Sale

      1502 Popple Dungeon Rd, Chester, VT 05143

      • 3 Beds
      • 4 Baths
      • 3,739 Sq Ft
      • Built 1989
      1502 Popple Dungeon Rd, Chester, VT 05143

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Betty McEnaney Diamond Realty

  • /43

    $419,900

    $5K PRICE DROP Under Contract
    • 5 Beds
    • 2 Baths
    • 1,982 Sq Ft

    176 Meadow Rd, Chester, VT 05143

    Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    176 Meadow Rd, Chester, VT 05143
  • /11

    $3,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • House for Rent

    735 Main St, Chester, VT 05143

    Lovely home within walking distance of Chester Village. Fully furnished, clean & comfortable. A great place to relax and enjoy all of what VT has to offer. All utilities except rubbish removal are paid by the owner. $3,000.00 per month plus deposit. Available August and September 2026. References and credit check required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    735 Main St, Chester, VT 05143
  • /34

    $269,000

    Sold Jun 15, 2026

    45 Dalrymple St, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • Built 1986

    Last Sold Summary

    • $230/SF
    • 6 Days On Market

    Current Estimated Value $270,457

    Last Listing Agent Julie Buffum Buffum Realty

    45 Dalrymple St, Chester, VT 05143
    • /36

      Est $1,297,063

      Not Listed For Sale

      938 Stigers Rd, Chester, VT 05143

      • 3 Beds
      • 3.5 Baths
      • 2,614 Sq Ft
      • Built 2011
      938 Stigers Rd, Chester, VT 05143

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Liz Moore Real Broker LLC

  • /17

    $75,000

    • 2 Beds
    • 1 Bath
    • 620 Sq Ft

    1144 Potash Brook Rd, Chester, VT 05143

    Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

    Agent Photo

    Julie Buffum

    Buffum Realty

    1144 Potash Brook Rd, Chester, VT 05143
  • /18

    $1,795 Per Month

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    659 Davidson Hill Rd Unit 1, Chester, VT 05143

    Upper floor apartment in a quiet split level between North Springfield, VT and Chester. Take advantage of a large yard in close proximity to many local employers or enjoy the nearby Springweather Dam and Nature Trails. This apartment has 2 good size bedrooms and 2 baths and is freshly painted with new flooring. It also features a spacious eat in kitchen, separate dining and living spaces

    659 Davidson Hill Rd Unit 1, Chester, VT 05143
  • /52

    $598,000

    Sold Oct 10, 2025

    2510 E Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $264/SF
    • 94 Days On Market

    Current Estimated Value $592,640

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
    • /60

      Est $486,858

      Not Listed For Sale

      472 Main St, Chester, VT 05143

      • 5 Beds
      • 7 Baths
      • 5,546 Sq Ft
      • Built 1850
      472 Main St, Chester, VT 05143

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  • /37

    $399,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    Agent Photo

    John Napier

    TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /14

    $289,000

    Sold Aug 14, 2026

    106 Contro Rd, Chester, VT 05143

    • 2 Beds
    • 2.5 Baths
    • 1,475 Sq Ft
    • Built 1985

    Last Sold Summary

    • $196/SF
    • 240 Days On Market

    Current Estimated Value $257,292

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    106 Contro Rd, Chester, VT 05143
    • /10

      Not Listed For Sale

      Lot 6 Jillie Ln, Chester, VT 05143

      Lot 6 Jillie Ln, Chester, VT 05143

      Last Sold Summary

      • 1,909 Days On Market

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

  • /60

    $469,000

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,676 Sq Ft

    64 Maple St, Chester, VT 05143

    Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area

    Betsy Adamovich Real Broker LLC

    64 Maple St, Chester, VT 05143
  • /15

    $80,000

    Sold Aug 17, 2026

    734 Gould Rd, Chester, VT 05143

    • Land
    • 3.85 Acres
    • $20,779 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    734 Gould Rd, Chester, VT 05143
    • /4

      Not Listed For Sale

      1599 Mattson Rd, Chester, VT 05143

      1599 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Amy Vashaw Twin State Realty LLC

  • /58

    $445,000

    $30K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,865 Sq Ft

    81 Main St, Chester, VT 05143

    Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

    Betsy Adamovich Real Broker LLC

    81 Main St, Chester, VT 05143
  • /55

    $605,000

    Sold Oct 02, 2025

    656 Main St, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 3,040 Sq Ft
    • Built 1904

    Last Sold Summary

    • 7% Below List Price
    • $199/SF
    • 47 Days On Market

    Current Estimated Value $598,571

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    656 Main St, Chester, VT 05143
    • /38

      Est $254,241

      Not Listed For Sale

      3089 Vt Route 11 W, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 1,732 Sq Ft
      • Built 1857
      3089 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  • /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

    Gary Coger Four Seasons Sotheby's Int'l Realty

    76 Goldthwaite Rd, Chester, VT 05143
  • /60

    $220,000

    Sold Nov 07, 2025

    442 Vermont 103, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft
    • Built 1941

    Last Sold Summary

    • 8% Below List Price
    • $215/SF
    • 70 Days On Market

    Current Estimated Value $235,321

    Last Listing Agent Rachael Lange Lange & Lange

    442 Vermont 103, Chester, VT 05143
    • /17

      Est $84,194

      Not Listed For Sale

      35 Depot St, Chester, VT 05143

      • 4 Beds
      • Built 1880
      35 Depot St, Chester, VT 05143

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Debra Staniscia Four Seasons Sotheby's Int'l Realty

  • /22

    $85,000

    • Land
    • 5 Acres
    • $17,000 per Acre

    0 Linden Way Unit 5093908, Chester, VT 05143

    Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

    Daire Gibney Barrett and Valley Associates Inc.

    0 Linden Way Unit 5093908, Chester, VT 05143
  • /21

    $227,000

    Sold Jan 30, 2026

    1374 Vt Route 103 N, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,222 Sq Ft
    • Built 1949

    Last Sold Summary

    • 5% Below List Price
    • $186/SF
    • 20 Days On Market

    Current Estimated Value $231,313

    Last Listing Agent Lisa Kelley Cummings & Co

    1374 Vt Route 103 N, Chester, VT 05143
    • /5

      Not Listed For Sale

      00 Trebo Rd, Chester, VT 05143

      00 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 349 Days On Market

      Last Listing Agent Brian Gehlich RE/MAX Four Seasons

  • /44

    $789,000

    $60K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 4,388 Sq Ft

    223 Coach Rd, Chester, VT 05143

    Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to

    Daire Gibney Barrett and Valley Associates Inc.

    223 Coach Rd, Chester, VT 05143
  • /58

    $475,000

    Sold Oct 10, 2025

    1923 N Hill Rd, Chester, VT 05143

    • 5 Beds
    • 3 Baths
    • 2,316 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 6 Days On Market

    Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
    • /18

      Est $330,385

      Not Listed For Sale

      3264 Trebo Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,487 Sq Ft
      • Built 1910
      3264 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 41 Days On Market

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

  • /25

    $289,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    447 Elm St, Chester, VT 05143

    Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add

    Jim Bialowski BHG Masiello Keene

    447 Elm St, Chester, VT 05143
  • /2

    $345,000

    Sold Oct 07, 2025

    154 Reed Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $308/SF
    • 10 Days On Market

    Current Estimated Value $296,455

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /6

      Not Listed For Sale

      00 Vt Route 11 W, Chester, VT 05143

      00 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 470 Days On Market

      Last Listing Agent Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  • /28

    $289,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,508 Sq Ft

    3713 Trebo Rd, Chester, VT 05143

    Extremely well maintained and thoughtfully updated, this spacious three bedroom, two and a half bath home is privately nestled on 2.6 acres on a quiet dead end. Offering the convenience of single level living, the property has been meticulously cared for over the years, with numerous improvements that make it comfortable, efficient, and move in ready. Inside you’ll find generously sized rooms

    Thaddeus Abare Barrett and Valley Associates Inc.

    3713 Trebo Rd, Chester, VT 05143
  • /13

    $275,000

    Sold Sep 10, 2025

    230 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 894 Sq Ft
    • Built 1970

    Last Sold Summary

    • $308/SF
    • 7 Days On Market

    Current Estimated Value $274,567

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • /4

      Est $550,679

      Not Listed For Sale

      1709 Potash Brook Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,688 Sq Ft
      • Built 2008
      1709 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 137 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /51

    $390,000

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

    663 Depot St, Chester, VT 05143

    Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates.

    Betsy Adamovich Real Broker LLC

    663 Depot St, Chester, VT 05143
  • /2

    $230,000

    Sold Nov 07, 2025

    2739 Route 11, Chester, VT 05143

    • 1 Bed
    • 1 Bath
    • 1,424 Sq Ft
    • Built 1987

    Last Sold Summary

    • 23% Below List Price
    • $162/SF
    • 13 Days On Market

    Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

    2739 Route 11, Chester, VT 05143
    • /29

      Est $355,903

      Not Listed For Sale

      201 Hill Top Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,137 Sq Ft
      • Built 1983
      201 Hill Top Rd, Chester, VT 05143

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /60

    $525,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,656 Sq Ft

    758 Weston-Andover Rd, Chester, VT 05143

    A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn, an

    Kevin Barnes William Raveis Real Estate Vermont Properties

    758 Weston-Andover Rd, Chester, VT 05143

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$360,000
Median Single Family Sale Price
$320,000
Median Townhouse Sale Price
$598,000
Median 2 Bedroom Sale Price
$330,000
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$263
Number of Homes for Sale
20
Last 12 months Home Sales
53
Months of Supply
4.50
Median List Price
$448,888
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-15%
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