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Newest Homes for Sale in Chester, VT

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  • 548 Crow Hill Rd, Chester, VT 05143
    548 Crow Hill Rd, Chester, VT 05143
    548 Crow Hill Rd, Chester, VT 05143
    /47

    $610,000

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    548 Crow Hill Rd, Chester, VT 05143

    Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for.Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide

    Jay Farrar Four Seasons Sotheby's Int'l Realty

    548 Crow Hill Rd, Chester, VT 05143
  • 979 Andover Ridge Rd, Chester, VT 05143
    979 Andover Ridge Rd, Chester, VT 05143
    979 Andover Ridge Rd, Chester, VT 05143
    /60

    $995,000

    • 3 Beds
    • 3 Baths
    • 2,167 Sq Ft

    979 Andover Ridge Rd, Chester, VT 05143

    Up a serene mountain road above the clouds in the quiet town of Andover, you’ll discover a special mountain property. This home has been distinctively renovated for carefree enjoyment. This retreat is surrounded by natural beauty with unprecedented long-range views to the west of the Green Mountain ridgeline. This highly efficient, low-maintenance home has wonderful natural light with views from

    Joseph Karl William Raveis Real Estate Vermont Properties

    979 Andover Ridge Rd, Chester, VT 05143
  • 159 Lower Bartonsville Rd, Chester, VT 05143
    159 Lower Bartonsville Rd, Chester, VT 05143
    159 Lower Bartonsville Rd, Chester, VT 05143
    /23

    $255,000

    Open Sat 11AM - 1PM Coming Soon
    • 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
  • 3713 Trebo Rd, Chester, VT 05143
    3713 Trebo Rd, Chester, VT 05143
    3713 Trebo Rd, Chester, VT 05143
    /28

    $289,900

    • 3 Beds
    • 2.5 Baths
    • 1,508 Sq Ft

    3713 Trebo Rd, Chester, VT 05143

    Extremely well maintained and thoughtfully updated, this spacious three bedroom, two and a half bath home is privately nestled on 2.6 acres on a quiet dead end. Offering the convenience of single level living, the property has been meticulously cared for over the years, with numerous improvements that make it comfortable, efficient, and move in ready. Inside you’ll find generously sized rooms

    Thaddeus Abare Barrett and Valley Associates Inc.

    3713 Trebo Rd, Chester, VT 05143
  • 96 Lower Bartonsville Rd, Chester, VT 05143
    96 Lower Bartonsville Rd, Chester, VT 05143
    96 Lower Bartonsville Rd, Chester, VT 05143
    /43

    $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 convenient location 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.

    Jessica Citera Cummings & Co

    96 Lower Bartonsville Rd, Chester, VT 05143
  • 0 Trebo Rd, Chester, VT 05143
    0 Trebo Rd, Chester, VT 05143
    0 Trebo 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
  • 302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill 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
  • 3781 Flamstead Rd, Chester, VT 05143
    3781 Flamstead Rd, Chester, VT 05143
    3781 Flamstead Rd, 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
  • 3 Eldredge Rd, Chester, VT 05143
    3 Eldredge Rd, Chester, VT 05143
    3 Eldredge Rd, Chester, VT 05143
    /60

    $1,600,000

    • 5 Beds
    • 5 Baths
    • 6,118 Sq Ft

    3 Eldredge Rd, Chester, VT 05143

    A rare opportunity to own a remarkable piece of Vermont and literary history. Lovingly designed and restored by the creators of the beloved Llama Llama children's book series and the accompanying Netflix animated series, this extraordinary mini-estate is offered for the first time by the family.The meticulously restored and maintained five-bedroom, five-bath, 6,100+ square foot post-and-beam

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    3 Eldredge Rd, Chester, VT 05143
  • 427 Depot St, Chester, VT 05143
    427 Depot St, Chester, VT 05143
    427 Depot St, 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
  • 1470 Popple Dungeon Rd, Chester, VT 05143
    1470 Popple Dungeon Rd, Chester, VT 05143
    1470 Popple Dungeon Rd, Chester, VT 05143
    /58

    $900,000

    $25K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    1470 Popple Dungeon Rd, Chester, VT 05143

    Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic

    Joseph Karl William Raveis Real Estate Vermont Properties

    1470 Popple Dungeon Rd, Chester, VT 05143
  • 00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    00 Quarry 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
  • 168 Chandler Rd, Chester, VT 05143
    168 Chandler Rd, Chester, VT 05143
    168 Chandler Rd, Chester, VT 05143
    /60

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,204 Sq Ft

    168 Chandler Rd, Chester, VT 05143

    Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and

    Diane Rousseau Four Seasons Sotheby's Int'l Realty

    168 Chandler Rd, Chester, VT 05143
  • 3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, 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
  • 223 Coach Rd, Chester, VT 05143
    223 Coach Rd, Chester, VT 05143
    223 Coach Rd, Chester, VT 05143
    /44

    $789,000

    $60K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 4,388 Sq Ft

    223 Coach Rd, Chester, VT 05143

    Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to

    Daire Gibney Barrett and Valley Associates Inc.

    223 Coach Rd, Chester, VT 05143
  • 758 Weston-Andover Rd, Chester, VT 05143
    758 Weston-Andover Rd, Chester, VT 05143
    758 Weston-Andover Rd, Chester, VT 05143
    /60

    $525,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,656 Sq Ft

    758 Weston-Andover Rd, Chester, VT 05143

    A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn, an

    Kevin Barnes William Raveis Real Estate Vermont Properties

    758 Weston-Andover Rd, Chester, VT 05143
  • 81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    /58

    $445,000

    $30K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,865 Sq Ft

    81 Main St, Chester, VT 05143

    Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

    Betsy Adamovich Real Broker LLC

    81 Main St, Chester, VT 05143
  • 3208 Green Mountain Turnpike, Chester, VT 05143
    3208 Green Mountain Turnpike, Chester, VT 05143
    3208 Green Mountain Turnpike, Chester, VT 05143
    /33

    $479,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft

    3208 Green Mountain Turnpike, Chester, VT 05143

    Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    3208 Green Mountain Turnpike, Chester, VT 05143
  • 00 Snell Rd, Chester, VT 05143
    00 Snell Rd, Chester, VT 05143
    00 Snell Rd, Chester, 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
  • 0 Linden Way Unit 5093908, Chester, VT 05143
    0 Linden Way Unit 5093908, Chester, VT 05143
    0 Linden Way Unit 5093908, 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
  • 1144 Potash Brook Rd, Chester, VT 05143
    1144 Potash Brook Rd, Chester, VT 05143
    1144 Potash Brook Rd, Chester, VT 05143
    /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
  • 250 Fenton Rd, Chester, VT 05143
    250 Fenton Rd, Chester, VT 05143
    250 Fenton 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
  • 76 Goldthwaite Rd, Chester, VT 05143
    76 Goldthwaite Rd, Chester, VT 05143
    76 Goldthwaite Rd, Chester, VT 05143
    /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

    Gary Coger Four Seasons Sotheby's Int'l Realty

    76 Goldthwaite Rd, Chester, VT 05143
  • 1302 Popple Dungeon Rd, Chester, VT 05143
    1302 Popple Dungeon Rd, Chester, VT 05143
    1302 Popple Dungeon Rd, Chester, VT 05143
    /53

    $1,490,000

    $200K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 5,400 Sq Ft

    1302 Popple Dungeon Rd, Chester, VT 05143

    Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details wide plank wood floors, paneled walls,

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1302 Popple Dungeon Rd, Chester, VT 05143
  • 508 Mattson Rd, Chester, VT 05143
    508 Mattson Rd, Chester, VT 05143
    508 Mattson 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
  • 0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    0 Green Mountain Turnpike Unit 5081034, 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
  • 2100 Baltimore Rd, Chester, VT 05143
    2100 Baltimore Rd, Chester, VT 05143
    2100 Baltimore 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
  • 201 Spruce Dr, Chester, VT 05143
    201 Spruce Dr, Chester, VT 05143
    201 Spruce Dr, Chester, VT 05143
    /60

    $879,999

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,310 Sq Ft

    201 Spruce Dr, Chester, VT 05143

    Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermont’s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, it’s an ideal basecamp for

    Mendi Michael Engel & Völkers Okemo

    201 Spruce Dr, Chester, VT 05143
  • 40 Fenton Rd, Chester, VT 05143
    40 Fenton Rd, Chester, VT 05143
    40 Fenton 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
  • 00 Contro Rd, Chester, VT 05143
    00 Contro Rd, Chester, VT 05143
    00 Contro Rd, 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
  • 3019 Popple Dungeon Rd, Chester, VT 05143
    3019 Popple Dungeon Rd, Chester, VT 05143
    3019 Popple Dungeon Rd, 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
  • 00 Remington Rd, Chester, VT 05143
    00 Remington Rd, Chester, VT 05143
    00 Remington 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
  • 1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    1175 Quarry 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
  • 3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    /30

    $650,000

    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, Chester, VT 05143
  • 000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, 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
Vermont Windsor County

Newest Listings for Sale in Chester, VT

Frequently Asked Questions

What is the average home price in Chester, VT?
Homes for sale in Chester, VT have an average home price of $561,022.
Are home prices dropping in Chester?
Yes, home prices in Chester are down 16% in the last 12 months.
How many homes have sold over the last 12 months in Chester, VT?
54 homes have sold in Chester, VT over the last 12 months.
What is the average household income in Chester, VT?
The average household income in Chester, VT is $92K.
What are the most popular zip codes in Chester, VT?
The most popular zip codes in Chester, VT include 05143, 05156, 05149, 05150 and 05146.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $436,944. If you put a 20% down payment of $87,400 and had a 30-year fixed mortgage with an interest rate of 6.65%, your estimated principal and interest payment would be $2,240 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $96K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chester is $92K.
How are the schools in Chester, VT?
Chester, VT has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Cavendish Town Elementary School, Grafton Elementary School and Ludlow Elementary School. Browse all the schools in Chester, VT to learn more.

Home Prices in Chester, VT

The median home sale price in Chester, VT is $369,500, down 11% year-over-year. Homes in Chester sell in 53 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$369,500
Median Single Family Sale Price
$320,000
Median Townhouse Sale Price
$579,000
Median 2 Bedroom Sale Price
$330,000
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$258
Number of Homes for Sale
20
Last 12 months Home Sales
54
Months of Supply
4.40
Median List Price
$436,944
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-11%
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