Chester Land for Sale

Welcome to Chester, a picturesque city that beautifully marries history with modern living. Nestled in the heart of Cheshire, England, Chester boasts a rich heritage that dates back to Roman times, evident in its well-preserved city walls, stunning amphitheater, and iconic black-and-white timbered buildings. The charming cobbled streets are lined with boutique shops, delightful cafes, and vibrant restaurants, making Chester not just a place to live, but a lifestyle choice that many dream of.

For those looking to invest in their future, we are excited to present a selection of prime land for sale in and around Chester. This area offers a unique opportunity to build your dream home or develop a property in a sought-after location. With its scenic views, proximity to the River Dee, and easy access to both the bustling city center and the serene countryside, this land is perfect for those who desire a tranquil yet convenient lifestyle.

Chester is well-connected, with excellent transport links to major cities such as Liverpool and Manchester, making it an ideal location for commuters. The community is vibrant and welcoming, with a range of schools, parks, and recreational facilities that cater to families and individuals alike.

Investing in land in Chester means becoming part of a thriving community rich in culture and opportunity. Whether you envision a bespoke family residence or a contemporary development, the possibilities are endless in this enchanting city. Don’t miss your chance to secure a piece of Chester’s charm—explore our available land for sale today!

Newest Chester Land for Sale

$149,000

5102503 MLS

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 Wastewater Permit for a five-bedroom residence. With zoning requiring a minimum of three acres and 200 feet of road frontage, the property presents an excellent opportunity for subdivision. One building site has already been identified as suitable, while the extensive road frontage provides the flexibility to explore additional potential home sites. A rare opportunity to create a private estate, family compound, or thoughtfully planned development in a quintessential Vermont setting. The location makes it easy to participate in all of the Chester Community events. Just a short drive to Okemo Mountain Resort for all of your outdoor adventures.

Trebo Rd, Chester

$250,000

5102143 MLS

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 existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102142.

3781 Flamstead Rd, Chester

$100,000

5100755 MLS

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 street, adding convenience for development. A gravel driveway provides easy access from First Avenue, and a recent survey is available. An existing foundation remains on the property and may offer the potential to be repurposed for a garage, shed, or other accessory structure. Buyers should perform their own due diligence and consult with a qualified contractor regarding its condition and suitability, as no representations or guarantees are being made. Enjoy a convenient location just 0.6 miles from the Chester Farmers Market and The Common shopping plaza, where you'll find local shops and cafés. The nearest hospital is approximately 10 minutes away, and Boston MA is 2.5 hours away, making this an ideal location for a primary residence, vacation home, or investment opportunity. Whether you're looking to build now or invest for the future, this well-located lot combines accessibility, utilities, and small-town Vermont charm.

427 Depot St, Chester

$229,000

5098347 MLS

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 viewpoint. Property has old stone walls and gorgeous rocks and stone on site for landscaping. Possible to subdivide. Adjoins town forest along the back property line. The 27.8 acres meets the minimum requirement for enrollment in the VT Current Use Forestry program for tax savings. Close to the charming village of Grafton for x-country skiing and dining at the historic Grafton Tavern. Okemo, Magic and Bromley Mountains are within easy reach. 15 min. to I91. Whether you are a summer recreational enthusiast, enjoy winter sports, or just want to chill in a small village atmosphere, this property is ready for your building plans!

00 Quarry Rd, Chester

$87,500

5094246 MLS

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.

00 Snell Rd, Chester

$85,000

5093908 MLS

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.

Linden Way, Chester

$579,900

5090837 MLS

This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

197a Chester St, Chester

$125,000

5090458 MLS

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 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 intimate, 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, sleeps multiple people with a queen bed in the bedroom, 3 bunks in the bunkroom, and a couch and dining booth that convert to beds as well, and there is an inside and an OUTSIDE kitchen! It serves as the perfect basecamp while you plan your future build, 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 site, where the camper is located, 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 that’s hard to find and impossible to replicate. All measurements approximate

250 Fenton Rd, Chester

$99,999

5082636 MLS

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 hillside that levels out beautifully, creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.

508 Mattson Rd, Chester

$119,000

5081034 MLS

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 you’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 surroundings—yet still be just a short drive from the heart of Chester.

Green Mountain Tpke, Chester

$74,500

5074848 MLS

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!

Tbd Farrar Rd, Chester

$159,000

5069927 MLS

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.

00 Contro Rd, Chester

Start Your Search

board logo 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, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .