Chester VT Real Estate

Chester town is located in Windsor County, Vermont with a population of 3154. The town covers a total area of 55.9 square miles, of which 55.7 square miles is land and 0.3 square miles is water. Nearby towns are Andover, Baltimore, and Springfield. Okemo Mountain Resort is one of the best places for skiing near Chester, VT. Students go to Green Mountain Union High School for study.

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New Listing - 3 days online
$675,000
3
BEDS
3
TOTAL BATHS
2,221
SQFT
835 Quarry Road Chester, VT 05143
Single Family Home For Sale
- Active

If you are searching for the perfect Vermont setting for year round living and enjoyment look no further than "Hidden Meadow". Situated on a very private 23.52 acres you will find a home and property that has been lovingly cared for by its original

Listing courtesy of Gary Coger of Four Seasons Sotheby's Int'l Realty: 802-228-4537
New Listing - 3 days online
$749,000
3
BEDS
2
TOTAL BATHS
2,776
SQFT
374 Richardson Road Chester, VT 05143
Single Family Home For Sale
- Active

Gracefully settled between the villages of Chester and Londonderry, sits a Vermont Farmhouse at road's end, sited on eleven+ acres of wood'n meadow. Dotted with old stone walls, a wildlife pond and enchanting views. The setting is magical. A wide cou

Listing courtesy of Lavinia Lee Brown of Four Seasons Sotheby's Int'l Realty: 802-297-8000
New Listing - a week online
$529,000
9
BEDS
9
TOTAL BATHS
5,242
SQFT
266 Main Street Chester, VT 05143
Single Family Home For Sale
- Active

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welco

Listing courtesy of Daire Gibney of Barrett and Valley Associates Inc.: 802-875-2323
New Listing - 2 weeks online
$249,000
2
BEDS
2
TOTAL BATHS
1,828
SQFT
125 and 61 Trebo Road Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

How sweet it is!!!....this home is perfect for those looking for full time or part time use. The main house is being offered furnished and will be ready to enjoy! Situated close to Route 103 for easy access to downtown Chester and short drives to 4 m

Listing courtesy of Lisa Kelley of Cummings & Co: 802-874-7081
$90,000
7.76
ACRES
WINDSOR
COUNTY
Lot 7 Jillie Lane #7 Chester, VT 05143
Land For Sale
- Active

Beautiful, wooded, and private! Located just outside of downtown Chester, on a private road with a maintenance agreement in place. Underground electric on site. Septic plans for a 3 bedroom single family home.

Listing courtesy of Thaddeus Abare of Barrett and Valley Associates Inc.: 802-875-2323
$485,000
3
BEDS
3
TOTAL BATHS
3,223
SQFT
74 Cobleigh Street Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

One of the true gems of Chester. This circa 1850 home has been transformed over the years. It has the charm of the original farmhouse yet has the functionality of a newer home. You enter into a lovely enclosed screened in porch with newer windows wh

Listing courtesy of Gary Coger of Four Seasons Sotheby's Int'l Realty: 802-228-4537
$360,000
142.1
ACRES
WINDSOR
COUNTY
000 Grafton Road Chester, VT 05143
Land For Sale
- Active

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 142.1 +/- lot is made up of two separate but adjoining parcels, one in Chester c

Listing courtesy of Daire Gibney of Barrett and Valley Associates Inc.: 802-875-2323
$65,000
6
ACRES
WINDSOR
COUNTY
Howard Road Chester, VT 05143
Land For Sale
- Active

Beautiful, quiet 6 acre wooded lot located just 2.5 miles from the center of lovely Chester, VT. Undeveloped land is becoming harder to find so don't miss out on the opportunity to build your Southern Vermont dream home and enjoy all this sweet spot

Listing courtesy of Christopher Cummings of Cummings & Co: 802-874-7081
$399,000
3
BEDS
2
TOTAL BATHS
1,800
SQFT
3078 VT Rt 10 Chester, VT 05143
Single Family Home For Sale
- Pending

Beautiful cape home on level country lot bordered by stone walls. Mature landscaping, above ground pool, screened gazebo, large back deck, 2-car attached garage along with attached utility shed, additional single car garage, walk out basement, first

Listing courtesy of Julie Buffum of Buffum Realty: 802-885-3000
Foreclosure
$214,500
3
BEDS
2
TOTAL BATHS
2,748
SQFT
5032 Vt Route 103 N Chester, VT 05143
Single Family Home For Sale
- Pending

This three bedroom, 1.5 bath home is just minutes to Ludlow and Okemo Mtn. ski resort. There is a large 4 car detached garage with office space and finished space above offering plenty of room for your hobbies and storage for all of your "toys". Lar

Listing courtesy of Judith Thompson of Walnut Hill Realty: 802-228-5544
$375,000
4
BEDS
2
TOTAL BATHS
2,528
SQFT
17 River Street Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

Wait until you see this home....large village lot with spectacular landscaping... the summer pictures are stunning. The convenience of this location is tremendous. Located on a quiet street that allows you to walk to the village without traffic. T

Listing courtesy of Betty Mcenaney of Bean Group / Vermont: 800-450-7784
$329,500
3
BEDS
2
TOTAL BATHS
2,576
SQFT
3074 VT Route 10 Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

Set back from the main road, is a very well-maintained 3 BR / 2 BA home with attached 2-car garage. Lovely and sun-lit living room. Eat-in kitchen is fully applianced with many cabinets and counterspace. Off of the kitchen is a deck. Master bedroo

Listing courtesy of Amy Messina of Town and Country Realty: 802-674-6311
$369,000
2
BEDS
2
TOTAL BATHS
2,240
SQFT
369 Logan Drive Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

COUNTRY COMFORT.....This home and detached heated garage/shop enjoys a peaceful setting on 14+ acres. The homes interior has been recently and tastefully updated consisting of 2 bedrooms, 2 baths and an open living/dining/kitchen floor plan. The cust

Listing courtesy of Roger Danyew of Diamond Realty: 802-228-1234
$239,000
3
BEDS
2
TOTAL BATHS
1,700
SQFT
981 Cavendish Road Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

Short drive down a country road, takes you home. Only 8 miles to Okemo Vail resort. This wonderful property offers everything you have been looking for. Open concept main level with kitchen, dining and living room. Mudroom with space for cubbies and

Listing courtesy of Lisa Kelley of Cummings & Co: 802-874-7081
$375,000
3
BEDS
3
TOTAL BATHS
1,602
SQFT
1698 Dean Brook Road Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

Looking for that quintessential log home in VT near Okemo Mountain? This is the first time that this home has ever been on the market. This house sits on 10 +/- acres and has been lovingly maintained and shines with character from the stone to ceili

Listing courtesy of Katherine Burns of William Raveis Vermont Properties: 802-228-8877
$325,000
1,824
SQFT
17 Grafton Street Chester, VT 05143
Multi-Family For Sale
- Active

Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a two unit apartment, it's top floor consists of a two b

Listing courtesy of Katherine Burns of William Raveis Vermont Properties: 802-228-8877
$429,000
2
BEDS
2
TOTAL BATHS
1,212
SQFT
1824 Vt Route 11 East Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

Grow, Play and Ski! Presenting the ideal property for a versatile home business. This completely remodeled 2 bedroom, 2 bath Chester country cape on 2 +/- acres awaits your entrepreneurial talents! The current owners had a seasonal, established Nurse

Listing courtesy of Geralyn Donohue of Engel & Volkers Okemo-Woodstock: 802-975-0338
$175,000
3
BEDS
1
TOTAL BATH
2,090
SQFT
3590 Vermont Route 103 North Chester, VT 05143
Single Family Home For Sale
- Active Under Contract

Affordable Chester home back on the market after many substantive upgrades and repairs, including, but not limited to: replaced and reinforced sills, replaced building supports, new shower fixtures, knob and tube removal, new sheetrock and primer, ne

Listing courtesy of Kristen Fehrenbach of Engel & Volkers Okemo-Woodstock: 802-975-0338
$389,000
85.07
ACRES
WINDSOR
COUNTY
1260 C Grafton Road #15.6 Chester, VT 05143
Land For Sale
- Pending

This stunning 85 +/- acre lot features a magnificent pond that is almost 300' across and hosts a large octagonal dock. There are any number of possible home sites around the pond, or nearby, for you to choose from. The parcel is 90% forested with v

Listing courtesy of Daire Gibney of Barrett and Valley Associates Inc.: 802-875-2323
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