2,599

Chester, VT Homes

Section Image
    • /60

      Est $443,595

      Not Listed For Sale

      196 North St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,960 Sq Ft
      • Built 1844
      196 North St, Chester, VT 05143

      Last Sold Summary

      • 166 Days On Market

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

  • /31

    $299,000

    $150K PRICE DROP Under Contract
    • 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
  • /60

    $460,000

    Sold Jul 09, 2026

    547 Williams Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $348/SF
    • 45 Days On Market

    Current Estimated Value $471,416

    Last Listing Agent Terri Edgerley Edge Realty Vermont

    547 Williams Rd, Chester, VT 05143
    • /28

      Est $375,999

      Not Listed For Sale

      250 North St, Chester, VT 05143

      • 5 Beds
      • 2 Baths
      • 2,152 Sq Ft
      • Built 1844
      250 North St, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

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

  • /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
  • /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 $401,597

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
    • /58

      Est $400,670

      Not Listed For Sale

      270 North St, Chester, VT 05143

      • 4 Beds
      • 1.5 Baths
      • 2,919 Sq Ft
      • Built 1810
      270 North St, Chester, VT 05143

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /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
  • /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 $825,660

    Last Listing Agent Cheyanne Pugliese

    1269 Howard Hill Rd, Chester, VT 05143
    • /40

      Est $217,394

      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

      Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  • /32

    $125,000

    $28K PRICE DROP
    • Land
    • 4.7 Acres
    • $26,596 per Acre

    250 Fenton Rd, Chester, VT 05143

    PRICE DROP!!!! 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

    Rachel Febbie EXP Realty

    250 Fenton 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 $1,240,404

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

    465 Pennell Rd, Chester, VT 05143
    • /39

      Est $432,450

      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

      Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

  • /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
  • /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
    • /34

      Est $870,522

      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

      Last Listing Agent Alison Cummings Cummings & Co

  • /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

    Diane Rousseau Four Seasons Sotheby's Int'l Realty

    168 Chandler 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 $571,730

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

    147 Pleasantview Ln, Chester, VT 05143
    • /59

      Est $528,115

      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

      Last Listing Agent Jeremy Collins Ridgeline Real Estate

  • /53

    $1,490,000

    $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
  • /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
    • /33

      Est $693,406

      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

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

  • /60

    $995,000

    • 3 Beds
    • 3 Baths
    • 2,167 Sq Ft

    979 Andover Ridge Rd, Chester, VT 05143

    Up a serene mountain road above the clouds in the quiet town of Andover, you’ll discover a special mountain property. This home has been distinctively renovated for carefree enjoyment. This retreat is surrounded by natural beauty with unprecedented long-range views to the west of the Green Mountain ridgeline. This highly efficient, low-maintenance home has wonderful natural light with views from

    Joseph Karl William Raveis Real Estate Vermont Properties

    979 Andover Ridge 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 $831,365

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    810 Quarry Rd, Chester, VT 05143
    • /19

      Est $229,514

      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

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /40

    $354,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    302 Davidson Hill Rd, Chester, VT 05143

    If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad

    Tyler Buswell Vermont Real Estate Company

    302 Davidson Hill Rd, Chester, VT 05143
  • /22

    $190,000

    Sold Aug 10, 2026

    1372 Potash Brook Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 732 Sq Ft
    • Built 1960

    Last Sold Summary

    • 5% Below List Price
    • $260/SF
    • 6 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    1372 Potash Brook Rd, Chester, VT 05143
    • /26

      Est $338,960

      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

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

  • /33

    $479,000

    $10K PRICE DROP
    • 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
  • /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 $364,957

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
    • /43

      Est $388,789

      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

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

  • /12

    $99,999

    $20K PRICE DROP
    • Land
    • 3.24 Acres
    • $30,864 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
  • /2

    $229,000

    Sold Aug 29, 2025

    87 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Above List Price
    • $273/SF
    • 2 Days On Market

    Current Estimated Value $237,801

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, Chester, VT 05143
    • /24

      Est $281,950

      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

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /60

    $1,600,000

    • 5 Beds
    • 5 Baths
    • 6,118 Sq Ft

    3 Eldredge Rd, Chester, VT 05143

    A rare opportunity to own a remarkable piece of Vermont and literary history. Lovingly designed and restored by the creators of the beloved Llama Llama children's book series and the accompanying Netflix animated series, this extraordinary mini-estate is offered for the first time by the family.The meticulously restored and maintained five-bedroom, five-bath, 6,100+ square foot post-and-beam

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    3 Eldredge Rd, Chester, VT 05143
  • /21

    $320,000

    Sold Dec 18, 2025

    870 Cummings Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,525 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 30 Days On Market

    Current Estimated Value $324,707

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143
    • /31

      Not Listed For Sale

      350 Farrar Rd, Chester, VT 05143

      • 4 Beds
      • 2.5 Baths
      • 2,747 Sq Ft
      • Built 1998
      350 Farrar Rd, Chester, VT 05143

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Linda Benoit Highland Realty

  • /47

    $549,000

    $20K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    3341 Trebo Rd, Chester, VT 05143

    Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a

    Daire Gibney Barrett and Valley Associates Inc.

    3341 Trebo Rd, Chester, VT 05143
  • /41

    $275,000

    Sold Aug 06, 2026

    397 River St, Chester, VT 05143

    • 4 Beds
    • 3 Baths
    • 3,332 Sq Ft
    • Built 1854

    Last Sold Summary

    • 21% Below List Price
    • $83/SF
    • 46 Days On Market

    Current Estimated Value $331,608

    Last Listing Agent Lisa Kelley Cummings & Co

    397 River St, Chester, VT 05143
    • /40

      Est $602,488

      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

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

Showing Results 81 - 120, Page 3 of 18

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