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Chester Homes for Sale

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  • 1144 Potash Brook Rd, Chester, VT 05143
    1144 Potash Brook Rd, Chester, VT 05143
    1144 Potash Brook Rd, Chester, VT 05143
    /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
  • 508 Mattson Rd, Chester, VT 05143
    508 Mattson Rd, Chester, VT 05143
    508 Mattson Rd, Chester, VT 05143
    /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

    Agent Photo

    Jessica Citera

    Cummings & Co

    508 Mattson Rd, Chester, VT 05143
  • 40 Fenton Rd, Chester, VT 05143
    40 Fenton Rd, Chester, VT 05143
    40 Fenton Rd, Chester, VT 05143
    /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
  • 81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    /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
  • 76 Goldthwaite Rd, Chester, VT 05143
    76 Goldthwaite Rd, Chester, VT 05143
    76 Goldthwaite Rd, Chester, VT 05143
    /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
  • 1470 Popple Dungeon Rd, Chester, VT 05143
    1470 Popple Dungeon Rd, Chester, VT 05143
    1470 Popple Dungeon Rd, Chester, VT 05143
    /58

    $879,900

    $45K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    1470 Popple Dungeon Rd, Chester, VT 05143

    Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic

    Joseph Karl William Raveis Real Estate Vermont Properties

    1470 Popple Dungeon Rd, Chester, VT 05143
  • 548 Crow Hill Rd, Chester, VT 05143
    548 Crow Hill Rd, Chester, VT 05143
    548 Crow Hill Rd, Chester, VT 05143
    /47

    $599,000

    $11K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    548 Crow Hill Rd, Chester, VT 05143

    Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for.Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide

    Jay Farrar Four Seasons Sotheby's Int'l Realty

    548 Crow Hill Rd, Chester, VT 05143
  • 0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    /9

    $119,000

    $10K PRICE DROP
    • Land
    • 7.95 Acres
    • $14,969 per Acre

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

    Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

    Thaddeus Abare Barrett and Valley Associates Inc.

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
  • 3019 Popple Dungeon Rd, Chester, VT 05143
    3019 Popple Dungeon Rd, Chester, VT 05143
    3019 Popple Dungeon Rd, Chester, VT 05143
    /20

    $169,000

    • 1 Bed
    • 1 Bath
    • 200 Sq Ft

    3019 Popple Dungeon Rd, Chester, VT 05143

    Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3019 Popple Dungeon Rd, Chester, VT 05143
  • 3537 Popple Dungeon Rd, Chester, VT 05143
    3537 Popple Dungeon Rd, Chester, VT 05143
    3537 Popple Dungeon Rd, Chester, VT 05143
    /22

    $249,900

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft

    3537 Popple Dungeon Rd, Chester, VT 05143

    Enjoy the beauty and charm of Vermont with this mobile home set on approximately 1 acre in Chester. Located across the road from a peaceful river, this property offers a wonderful setting for enjoying the outdoors and the natural beauty of the area. The property features an oversized 2 car garage with plenty of room for vehicles, recreational equipment, tools, and hobbies. Above the garage is

    Thaddeus Abare Barrett and Valley Associates Inc.

    3537 Popple Dungeon Rd, Chester, VT 05143
  • 427 Depot St, Chester, VT 05143
    427 Depot St, Chester, VT 05143
    427 Depot St, Chester, VT 05143
    /22

    $100,000

    • Land
    • 23,958 Sq Ft
    • $181,818 per Acre

    427 Depot St, Chester, VT 05143

    Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are available at the

    Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

    427 Depot St, Chester, VT 05143
  • 3781 Flamstead Rd, Chester, VT 05143
    3781 Flamstead Rd, Chester, VT 05143
    3781 Flamstead Rd, Chester, VT 05143
    /60

    $225,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    3781 Flamstead Rd, Chester, VT 05143

    Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An

    Amy Hill EXP Realty

    3781 Flamstead Rd, Chester, VT 05143
  • 00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    /25

    $229,000

    • Land
    • 27.8 Acres
    • $8,237 per Acre

    00 Quarry Rd, Chester, VT 05143

    27.8 +/- acre wooded parcel close to Chester Village with beautiful views. Driveway is roughed in and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Newly opened views from the plateau along the ridge accessed by an established logging road are a must see. Soil tests indicate a 3 bedroom home site is possible at the scenic

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Quarry Rd, Chester, VT 05143
  • 3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    /38

    $249,500

    • 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
  • 00 Contro Rd, Chester, VT 05143
    00 Contro Rd, Chester, VT 05143
    00 Contro Rd, Chester, VT 05143
    /3

    $159,000

    • Land
    • 5 Acres
    • $31,800 per Acre

    00 Contro Rd, Chester, VT 05143

    There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town

    Christine Lewis Brattleboro Area Realty

    00 Contro Rd, Chester, VT 05143
  • 00 Remington Rd, Chester, VT 05143
    00 Remington Rd, Chester, VT 05143
    00 Remington Rd, Chester, VT 05143
    /14

    $74,000

    • Land
    • 15.5 Acres
    • $4,774 per Acre

    00 Remington Rd, Chester, VT 05143

    Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    00 Remington Rd, Chester, VT 05143
  • 000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    /22

    $249,000

    $50K PRICE DROP
    • Land
    • 84 Acres
    • $2,964 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property

    Daire Gibney Barrett and Valley Associates Inc.

    000 Green Mountain Turnpike, Andover, VT 05143
  • 00 Hillcrest Rd, Andover, VT 05143
    00 Hillcrest Rd, Andover, VT 05143
    /2

    $90,000

    • Land
    • 4.05 Acres
    • $22,222 per Acre

    00 Hillcrest Rd, Andover, VT 05143

    Build your dream home or secluded retreat on this 4.05 acre wooded parcel on a quiet country lane close to shopping, skiing, snowmobiling, lakes and more. A wastewater permit is in place for a 5 bedroom home, and electricity is right at the street. It's less than 30 minutes to Magic Mountain or Bromley, or 35 to Stratton or Okemo. Charming Chester is 15 minutes away, and shopping in Londonderry

    Deborah Hanst

    00 Hillcrest Rd, Andover, VT 05143
  • 00 Snell Rd, Chester, VT 05143
    00 Snell Rd, Chester, VT 05143
    00 Snell Rd, Chester, VT 05143
    /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
  • 3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    /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
  • 168 Chandler Rd, Chester, VT 05143
    168 Chandler Rd, Chester, VT 05143
    168 Chandler Rd, Chester, VT 05143
    /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
  • 1302 Popple Dungeon Rd, Chester, VT 05143
    1302 Popple Dungeon Rd, Chester, VT 05143
    1302 Popple Dungeon Rd, Chester, VT 05143
    /53

    $1,349,000

    $341K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 5,400 Sq Ft

    1302 Popple Dungeon Rd, Chester, VT 05143

    Set on 18 private acres, Popple Fields is a very special Vermont property one that feels less like a house that was built and more like a home that was lovingly crafted.Built in 1989 by its owner, a true master craftsman, this Williamsburg saltbox reproduction reflects a lifelong appreciation for traditional architecture, fine woodworking, and the quiet beauty of things made by hand. The

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1302 Popple Dungeon Rd, Chester, VT 05143
  • 302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill Rd, Chester, VT 05143
    /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
  • 3208 Green Mountain Turnpike, Chester, VT 05143
    3208 Green Mountain Turnpike, Chester, VT 05143
    3208 Green Mountain Turnpike, Chester, VT 05143
    /33

    $449,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft

    3208 Green Mountain Turnpike, Chester, VT 05143

    Located on the edge of the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove enhancing an inviting open-concept living space. The kitchen/dining has butcher block counters, attractive

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    3208 Green Mountain Turnpike, Chester, VT 05143
  • 3341 Trebo Rd, Chester, VT 05143
    3341 Trebo Rd, Chester, VT 05143
    3341 Trebo Rd, Chester, VT 05143
    /47

    $549,000

    $20K PRICE DROP
    • 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

    Daire Gibney Barrett and Valley Associates Inc.

    3341 Trebo Rd, Chester, VT 05143
  • 1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    /25

    $270,000

    $30K PRICE DROP
    • Land
    • 75 Acres
    • $3,600 per Acre

    1175 Quarry Rd, Chester, VT 05143

    A private Vermont retreat with room to make it your own. Tucked approximately one mile up a quiet, dead-end dirt road in Chester, this expansive parcel offers the kind of space and seclusion that can be hard to find. Mostly wooded with varied, rising terrain, the property offers plenty to explore and possibilities for recreation, a private homestead, hunting camp, or seasonal getaway.Now

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
Vermont Windsor County Chester

Real Estate & Homes for Sale in Chester, Chester

Chester, VT, VT Home Prices vs. Nearby Neighborhoods

Chester Cavendish Rockingham
Median Home Price
$399,000
$460,000
$375,000
Median Sale Price
$350,000
-13% YoY
$397,500
+34% YoY
$351,000
+38% YoY
Avg. Price per Square Foot
$253
$261
$230
Median Single Family Price
$320,000
$330,000
$345,000
Median Townhouse Price
$510,000
$604,500
--
Total Active Listings
26 listings
23 listings
4 listings
Market Conditions
4 Months of Supply
Seller's Market
8 Months of Supply
Buyer's Market
3 Months of Supply
Seller's Market

Frequently Asked Questions Why Live in Chester

Is Chester a good place to live?
Chester is a good place to live. Chester is considered very car-dependent and somewhat bikeable. Chester has 2 parks for recreational activities.It has a median age of 50. The average household income is $92,179 which is below the national average. College graduates make up 40% of residents. A majority of residents in Chester are home owners, with 25% of residents renting and 75% of residents owning their home. A local real estate agent serving Chester can help you decide if this neighborhood is the right one for you. Learn more on our Chester neighborhood guide.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $399,000. If you put a 20% down payment of $79,800 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $2,110 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $90K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chester is $92K.
What are the best public schools in Chester?
The best public schools that serve Chester are:
What are the most popular zip codes in Chester, Chester, VT?
The most popular zip codes in Chester, Chester, VT include 05143, 05156, 05150, 05146 and 05149.
What are the most popular neighborhoods near Chester, Chester, VT?
The most popular neighborhoods near Chester, Chester, VT are West Claremont and South End.
Are home prices dropping in Chester?
Yes, home prices in Chester are down 25% in the last 12 months.
Learn more about living in Chester
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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