16

Chester, VT Homes for Sale under $400,000

Section Image Section Image
  • /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

    Agent Photo

    Gail Beardmore

    Engel & Völkers Okemo

    0 Trebo 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

    Agent Photo

    John Napier

    TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /25

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    447 Elm St, Chester, VT 05143

    Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add

    Jim Bialowski BHG Masiello Keene

    447 Elm St, 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

    $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

    $250,000

    • 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
  • /19

    $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 potential long range views. Driveway has been cut and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Potential views from the plateau along the ridge accessed by an established logging road. Soil tests indicate a 3 bedroom home site is possible at the scenic viewpoint.

    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
  • /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
  • /32

    $125,000

    $28K PRICE DROP
    • Land
    • 4.7 Acres
    • $26,596 per Acre

    250 Fenton Rd, Chester, VT 05143

    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

    Rachel Febbie EXP Realty

    250 Fenton Rd, 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
  • /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
  • /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
  • /42

    $375,000

    • 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 path right 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. The attic

    Jessica Citera Cummings & Co

    96 Lower Bartonsville Rd, Chester, VT 05143

Home Price Trends

Median Sale Price
$369,500
Median Single Family Sale Price
$338,750
Median Townhouse Sale Price
$598,000
Median 2 Bedroom Sale Price
$330,000
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$259
Number of Homes for Sale
19
Last 12 months Home Sales
56
Months of Supply
4.10
Median List Price
$425,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-13%
How to Buy a Home How to Finance a Home How to Sell a Home