18

Chester, VT Homes for Sale under $300,000

Section Image Section Image
  • /17

    $75,000

    • 2 Beds
    • 1 Bath
    • 620 Sq Ft

    1144 Potash Brook Rd, Chester, VT 05143

    Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

    Agent Photo

    Julie Buffum

    Buffum Realty

    1144 Potash Brook Rd, Chester, VT 05143
  • /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
  • /22

    $85,000

    • Land
    • 5 Acres
    • $17,000 per Acre

    0 Linden Way Unit 5093908, Chester, VT 05143

    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.

    0 Linden Way Unit 5093908, 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
  • /25

    $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 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

    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
  • /14

    $74,000

    • Land
    • 15.5 Acres
    • $4,774 per Acre

    00 Remington Rd, Chester, VT 05143

    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

    00 Remington 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
  • /14

    $87,500

    • Land
    • 10.4 Acres
    • $8,413 per Acre

    00 Snell Rd, Chester, VT 05143

    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

    00 Snell Rd, Chester, 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
  • /12

    $99,999

    $20K PRICE DROP
    • Land
    • 3.24 Acres
    • $30,864 per Acre

    508 Mattson Rd, Chester, VT 05143

    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

    508 Mattson Rd, Chester, VT 05143
  • /23

    $255,000

    • 3 Beds
    • 1.5 Baths
    • 1,683 Sq Ft

    159 Lower Bartonsville Rd, Chester, VT 05143

    Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly

    Abby Gerbick Century 21 Highview Realty

    159 Lower Bartonsville 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

Home Price Trends

Median Sale Price
$369,500
Median Single Family Sale Price
$350,000
Median Townhouse Sale Price
$560,000
Median 2 Bedroom Sale Price
$330,000
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$266
Number of Homes for Sale
19
Last 12 months Home Sales
52
Months of Supply
4.40
Median List Price
$448,888
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