Chester VT Real Estate & Land for Sale

15 Properties Found

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Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5093908
Type:
Land
Subdivision:
Linden Way- 2026
Lot size:
5 Acres
Courtesy: Barrett and Valley Associates Inc.
View additional info

ADDITIONAL INFORMATION

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 primary residence or Vermont getaway without sacrificing proximity to local shops, restaurants, and community events. Power and fiber-optic internet are available, and a state-approved 4 Bedroom wastewater permit is already in place, helping streamline the path toward future development. The parcel also includes frontage along Route 35, providing an additional access option for future consideration. Ideally located for four-season recreation, the property is within easy driving distance of Okemo, Magic Mountain, Stratton, and Bromley ski areas, as well as hiking, biking, fishing, and countless outdoor adventures throughout Southern Vermont. Whether you're planning a year-round residence or a Vermont retreat, this property offers a rare combination of privacy, accessibility, and convenience in a sought-after Chester location.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5094246
Type:
Land
Lot size:
10.4 Acres
Courtesy: Four Seasons Sotheby's Int'l Realty
View additional info

ADDITIONAL INFORMATION

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 Mountain, Chester Village.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5090458
Type:
Land
Lot size:
4.7 Acres
Courtesy: EXP Realty
View additional info

ADDITIONAL INFORMATION

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 river, softened by a scattering of mature trees that add shade, character, and seasonal color. Set along gentle bends in the river, the property feels open yet intimateâ??an ideal setting for gardens, gatherings, or simply relaxing under the sky. Wildlife is abundant here: deer grazing at dusk, fox weaving through the meadow, and birdsong drifting from the forest edge. A 33-foot camper is already positioned on the designated house site outside the floodplain, allowing you to enjoy the property from day one. Powered by a solar-supported electric generator and a gas generator, it serves as the perfect basecamp while you plan your future buildâ??or as a ready-made retreat just as it is. An 8' x 8' storage unit provides convenient space for kayaks, fishing gear, a mower, or all the toys that come with Vermont living. The house siteâ??where the camper is locatedâ??sits entirely outside the floodplain and comes with an approved 4-bedroom wastewater permit and power at the road. While a portion of the land does lie within the floodplain, the property as a whole saw very little impact during the 2023 flood. This land offers a peacefulness thatâ??s hard to find and impossible to replicate.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5082636
Type:
Land
Lot size:
3.24 Acres
Courtesy: Cummings & Co
View additional info

ADDITIONAL INFORMATION

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 barnâ??ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifullyâ??creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5081034
Type:
Land
Lot size:
7.95 Acres
Courtesy: Barrett and Valley Associates Inc.
View additional info

ADDITIONAL INFORMATION

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 village below an ideal backdrop for your dream home or getaway retreat. Whether youâ??re looking to build, relax, or invest this property is sure to impress. Quiet, scenic, and full of Vermont character, this is a special piece of land where you can truly slow down and enjoy the surroundingsâ??yet still be just a short drive from the heart of Chester.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5079082
Type:
Land
Lot size:
12.51 Acres
Courtesy: Mary W. Davis Realtor & Assoc., Inc.
View additional info

ADDITIONAL INFORMATION

Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home. Located in an area identified for development, it offers both a wonderful building site and long-term investment potential. The septic design is complete, and a 50-foot right-of-way is shown on the survey and is ready to be roughed-in. Bring in electricity, water, and septic, then start building your Vermont dream. Properties like this are increasingly hard to find: private, scenic and close to the heart of the village.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5074848
Type:
Land
Lot size:
16.24 Acres
Courtesy: EXP Realty
View additional info

ADDITIONAL INFORMATION

Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5069927
Type:
Land
Lot size:
5 Acres
Courtesy: Brattleboro Area Realty
View additional info

ADDITIONAL INFORMATION

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 maintained road is easy access and power near by. It is the perfect time to escape, start a new beginning, or just take a weekend to breathe. Please call GMP and communications for availability and cost.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5061671
Type:
Land
Subdivision:
Chester Remington
Lot size:
15.5 Acres
Courtesy: Berkshire Hathaway HomeServices Stratton Home
View additional info

ADDITIONAL INFORMATION

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.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5058824
Type:
Land
Lot size:
75 Acres
Courtesy: BHG Masiello Keene
View additional info

ADDITIONAL INFORMATION

Discover the true meaning of "getting away from it all" at 1175 Quarry Road. This expansive 75 acre parcel is tucked away a full mile up a quiet, dead end dirt road in the desirable town of Chester. Mostly wooded with rising topography. Itâ??s an ideal canvas for a private homestead, a hunting camp, or a seasonal getaway. You get the peace of a dead end road with the convenience of being near four local ski mountains. Land of this scale and privacy is increasingly rare. Come explore and see the potential for yourself. Conveniently located 15 minutes to I-91, Under 30 minutes to Okemo, Bromley and Magic Mountain and under an hour to Stratton and Killington.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5053371
Type:
Land
Lot size:
6.63 Acres
Courtesy: Lange & Lange
View additional info

ADDITIONAL INFORMATION

Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been doneâ??now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether you're dreaming of a cozy cabin, amodern hideaway, or a base for four-season adventure, this property has the flexibility and setting to make it happen. Just minutes to Chester Village, and an easy drive to Okemo Mountain, local trails, and swimming holes, this location strikes the perfect balance between convenience and tranquility. There is also an option to purchase 1 of the two lots. This option is for two combined lots.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5052955
Type:
Land
Lot size:
3.35 Acres
Courtesy: Lange & Lange
View additional info

ADDITIONAL INFORMATION

Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been doneâ??now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether you're dreaming of a cozy cabin, a modern hideaway, or a base for four-season adventure, this property has the flexibility and setting to make it happen. Just minutes to Chester Village, and an easy drive to Okemo Mountain, local trails, and swimming holes, this location strikes the perfect balance between convenience and tranquility.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5052948
Type:
Land
Lot size:
3.28 Acres
Courtesy: Lange & Lange
View additional info

ADDITIONAL INFORMATION

Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been doneâ??now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether you're dreaming of a cozy cabin, a modern hideaway, or a base for four-season adventure, this property has the flexibility and setting to make it happen. Just minutes to Chester Village, and an easy drive to Okemo Mountain, local trails, and swimming holes, this location strikes the perfect balance between convenience and tranquility.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
5023272
Type:
Land
Lot size:
84 Acres
Courtesy: Barrett and Valley Associates Inc.
View additional info

ADDITIONAL INFORMATION

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 embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermontâ??s Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Donâ??t miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
4982433
Type:
Land
Lot size:
27.8 Acres
Courtesy: Engel & Volkers Okemo
View additional info

ADDITIONAL INFORMATION

Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary building site makes for easy access and immediate potential. A logging trail winds to a stunning ridge-top plateau, ideal for an off-the-grid cabin, artist studio, or peaceful sanctuary surrounded by breathtaking vistas. The land borders the Chester Town Forest, ensuring lasting privacy and a connection to nature. Outdoor enthusiasts will love the opportunity to hike, snowshoe, or mountain bike directly from the property. You can also cross-country ski in nearby Grafton or enjoy downhill skiing at Okemo, Magic, Stratton, or Bromley Mountains, all within easy reach. Conveniently located just minutes from Chester Village and close to I-91, this unique property combines natural beauty, accessibility, and investment potentialâ??only 3 hours from Boston and 4.5 hours from New York City. Embrace the best of Vermontâ??s four-season lifestyle and make this remarkable Chester VT property your own mountain retreat.

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Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


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. Data last updated {{last updated}}.




Chester Real Estate

Chester is located in Vermont. Chester, Vermont has a population of 3,010. Chester is less family-centric than the surrounding county with 24.13% of the households containing married families with children. The county average for households married with children is 26.01%.

The median household income in Chester, Vermont is $61,397. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Chester is 53.2 years.

Chester Weather

The average high temperature in July is 81.5 degrees, with an average low temperature in January of 7.4 degrees. The average rainfall is approximately 45.2 inches per year, with 67.6 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $359,000
    19.1%
    change since last quarter
  • # Active listings

    39
    30-day change

Chester Schools and Demographics

Education near Chester, VT

City County
High School Graduates 96.52 94.16
College Degree - 2 year 6.97 8.49
College Degree - 4 year 40.18 40.21
Graduate Degree 11.68 12.49
Expenditures per Student 26,463 26,463
Students per Teacher 12.3 12.3

Elementary Schools near Chester, VT

Grades Students P/T Ratio ZIP
Chester-Andover USD #29 PK - 06 261 13 05143
Elm Hill School PK - 02 415 17.7 05156
Flood Brook USD #301 PK - 08 322 11.1 05148
Grafton Elementary School PK - 06 103 13.7 05146
Ludlow Elementary School PK - 06 115 8 05149
Union School 03 - 05 256 10 05156

Middle Schools near Chester, VT

Grades Students P/T Ratio ZIP
Riverside School 06 - 08 291 11.2 05156

High Schools near Chester, VT

Grades Students P/T Ratio ZIP
Black River USD #39 07 - 12 172 8.6 05149
Green Mountain UHSD #35 07 - 12 336 10.2 05143
Springfield High School 09 - 12 433 11.9 05156

Ungraded Schools near Chester, VT

Grades Students P/T Ratio ZIP
River Valley Technical Center UG - UG 0 05156

Demographics near Chester, VT

City County
Neighborhood Type Small town
Population 3,010 57,593
Population Density 54 59
Median Age 53.2 47.8
People per Household 2.4 2.3
Median Household Income 61,397 63,787
Average Income per Capita 35,517 39,377

Real estate near Chester