Chester, VT Homes for Sale

/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

Julie Buffum

Buffum Realty

1144 Potash Brook Rd, Chester, VT 05143
/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

Gail Beardmore

Engel & Völkers Okemo

0 Trebo 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

Jessica Citera

Cummings & Co

508 Mattson Rd, Chester, VT 05143
/43
$360,000

$15K PRICE DROP
- 3 Beds
- 2 Baths
- 1,312 Sq Ft
96 Lower Bartonsville Rd, Chester, VT 05143

This tastefully updated ranch-style home is set on a unique one-acre parcel with a convenient location to the Williams River. Three bedrooms and two baths, thoughtfully updated interior with inviting living spaces and the convenience of one level living. A full basement provides valuable additional space and could be finished to create a family room, home office, recreation area, or even a gym.

Jessica Citera

Cummings & Co

96 Lower Bartonsville 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

John Napier

TPW Real Estate

40 Fenton Rd, 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
/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
$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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/60
$879,999

$9K PRICE DROP
- 3 Beds
- 2 Baths
- 3,310 Sq Ft
201 Spruce Dr, Chester, VT 05143

Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermont’s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, it’s an ideal basecamp for

Mendi Michael Engel & Völkers Okemo

201 Spruce Dr, 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
/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
/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
/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
/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
/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
/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
$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
/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
/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
/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
/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
/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
/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

Why Live in Chester

Chester, Vermont, is a small-town community known for its quiet charm and close-knit atmosphere. Homebuyers can choose from a variety of home styles, including older Cape Cods and colonials, ranch-style homes, and contemporary houses, with options ranging from tightly arranged homes in the town center to sprawling properties on the outskirts. Chester's local dining scene features favorites like Country Girl Diner, Pizza Stone VT, and MacLaomainn's Scottish Pub, while Southern Pie Cafe offers delightful desserts. Residents enjoy recreational amenities along Lovers Lane Road, including a municipal pool, skatepark, and hiking trails in Chester Town Forest. The annual Chester Festival on the Green in September celebrates local art and culture with craft vendors and live performances. While Chester is car-dependent, commuters can access nearby towns via State Route 11 and 103, with Springfield Hospital 7 miles away and Albany International Airport 88 miles south. The area experiences a unique mud season from March to June, affecting travel on the numerous dirt roads. Chester's schools have average ratings, with Green Mountain Union High offering a low student-teacher ratio.

Learn more about living in Chester

Chester, VT Home Prices

	Chester, VT
Median Home Price	$449,000
Median Sale Price	$369,500 -13% YoY
Avg. Price per Square Foot	$266
Median Single Family Price	$359,000
Median Townhouse Price	$560,000
Total Active Listings	33 listings
Market Conditions	5 Months of Supply Balanced Market

Frequently Asked Questions

What is the average home price in Chester, VT?

Homes for sale in Chester, VT have an average home price of $550,606.

Are home prices dropping in Chester?

Yes, home prices in Chester are down 21% in the last 12 months.

How many homes have sold over the last 12 months in Chester, VT?

50 homes have sold in Chester, VT over the last 12 months.

What is the average household income in Chester, VT?

The average household income in Chester, VT is $92K.

What are the most popular zip codes in Chester, VT?

The most popular zip codes in Chester, VT include 05143, 05156, 05150, 05149 and 05146.

How much do you need to make to afford a house in Chester?

The median home price in Chester is $449,000. If you put a 20% down payment of $89,800 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $2,380 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $102K 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.

How are the schools in Chester, VT?

Chester, VT has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Cavendish Town Elementary School, Grafton Elementary School and Ludlow Elementary School. Browse all the schools in Chester, VT to learn more.

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