Chester, VT Homes for Sale under $300,000

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

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

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.

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 done—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

Rachael Lange Lange & Lange

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.

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 done—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

Rachael Lange Lange & Lange

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

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

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.

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

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

Rachel Febbie EXP Realty

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

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.It’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

Jessica Samples BHG Masiello Keene