19

Chester, VT Houses for Sale

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  • 31 Palmer Rd, Chester, VT 05143
    31 Palmer Rd, Chester, VT 05143
    31 Palmer Rd, Chester, VT 05143
    /59

    $669,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,605 Sq Ft

    31 Palmer Rd, Chester, VT 05143

    This is not your typical Vermont farmhouse—it’s far better. Surrounded by rolling fields and pastoral views, this beautifully updated home combines classic country charm with modern ease. Inside, you’ll find a warm, sunlit layout anchored by a stunning chef’s kitchen featuring high-end Viking appliances, granite counters, and custom cabinetry. The spacious primary suite is a luxurious retreat,

    Daire Gibney Barrett and Valley Associates Inc.

    31 Palmer Rd, Chester, VT 05143
  • 3236 Weston-Andover Rd, Chester, VT 05143
    3236 Weston-Andover Rd, Chester, VT 05143
    3236 Weston-Andover Rd, Chester, VT 05143
    /60

    $638,000

    • 4 Beds
    • 3 Baths
    • 2,456 Sq Ft

    3236 Weston-Andover Rd, Chester, VT 05143

    **Delayed showings until July 2nd** - Set on a stunning, level 7.38-acre parcel, this beautifully updated farmhouse is turnkey and full of character, comfort, and space! The convenient mudroom offers built-in shelving for your gear and leads into a lovely country kitchen featuring handmade cabinetry, granite countertops, a butcher block island, and a cozy breakfast bar. Step out to the charming

    Mendi Michael Engel & Völkers Okemo

    3236 Weston-Andover Rd, Chester, VT 05143
  • 157 Thompson Rd, Chester, VT 05143
    157 Thompson Rd, Chester, VT 05143
    157 Thompson Rd, Chester, VT 05143
    /58

    $1,249,000 Open Sat 10AM - 12PM

    • 4 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    157 Thompson Rd, Chester, VT 05143

    Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

    Joe Castaluccio Winhall Real Estate

    157 Thompson Rd, Chester, VT 05143
  • 725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    /58

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 2,744 Sq Ft

    725 Flamstead Rd, Chester, VT 05143

    Inspired by Frank Lloyd Wright’s “The Cottage,” where simplicity, warmth, and a deep connection to nature come together in perfect balance. Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    725 Flamstead Rd, Chester, VT 05143
  • 1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, Chester, VT 05143
    /20

    $1,175,000

    • 4 Beds
    • 4 Baths
    • 3,920 Sq Ft

    1847 Trebo Rd, Chester, VT 05143

    With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1847 Trebo Rd, Chester, VT 05143
  • 656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    /54

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    656 Main St, Chester, VT 05143

    Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass

    Geralyn Donohue Engel & Völkers Okemo

    656 Main St, Chester, VT 05143
  • 534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    /60

    $599,000

    • 7 Beds
    • 3.5 Baths
    • 3,850 Sq Ft

    534 Elm St, Chester, VT 05143

    Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal

    Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
  • 525 Route 103 N, Chester, VT 05143
    525 Route 103 N, Chester, VT 05143
    525 Route 103 N, Chester, VT 05143
    /60

    $595,000

    • 6 Beds
    • 1 Bath
    • 2,308 Sq Ft

    525 Route 103 N, Chester, VT 05143

    The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

    Glenn Olney Barrett and Valley Associates Inc.

    525 Route 103 N, Chester, VT 05143
  • 1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    /56

    $629,000

    • 5 Beds
    • 3.5 Baths
    • 3,470 Sq Ft

    1057 Quarry Rd, Chester, VT 05143

    Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    1057 Quarry Rd, Chester, VT 05143
  • 2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    /52

    $627,500

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft

    2510 E Hill Rd, Chester, VT 05143

    This home on East Hill Road commands one of the area's best views all the way to Stratton! It is one of those spots where the view is different every day & spectacular! The home sits on 14 acres & it overlooks land protected by the Vermont Land Trust and mountains beyond. From the moment you enter, you won't want to leave. It is immaculate and ready to go. A large mudroom with a slate floor &

    Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
  • 769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    /41

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    769 Davidson Hill Rd, Chester, VT 05143

    Simplify your life and reconnect with nature in this peaceful Chester home. Set on over 5 private acres, this 3-bedroom ranch offers easy, one-level living surrounded by Vermont’s natural beauty. Whether you're seeking a low-maintenance primary residence, a country getaway, or a downsizing opportunity, this home delivers comfort without complication. From the wheelchair-accessible ramp to the

    Frank Provance Diamond Realty

    769 Davidson Hill Rd, Chester, VT 05143
  • 465 Pennell Rd, Chester, VT 05143
    465 Pennell Rd, Chester, VT 05143
    465 Pennell Rd, Chester, VT 05143
    /47

    $1,500,000

    • 4 Beds
    • 4.5 Baths
    • 5,700 Sq Ft

    465 Pennell Rd, Chester, VT 05143

    Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options.The setting is nothing short of spectacular. Enjoy

    Gary Coger Four Seasons Sotheby's Int'l Realty

    465 Pennell Rd, Chester, VT 05143
  • 160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    /26

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,327 Sq Ft

    160 Depot St, Chester, VT 05143

    Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

    Joshua Lemieux Remax Summit

    160 Depot St, Chester, VT 05143
  • 491 Farrar Rd, Chester, VT 05143
    491 Farrar Rd, Chester, VT 05143
    491 Farrar Rd, Chester, VT 05143
    /29

    $399,000

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft

    491 Farrar Rd, Chester, VT 05143

    Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

    Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
  • 938 Stigers Rd, Chester, VT 05143
    938 Stigers Rd, Chester, VT 05143
    938 Stigers Rd, Chester, VT 05143
    /36

    $1,650,000

    • 3 Beds
    • 3.5 Baths
    • 2,614 Sq Ft

    938 Stigers Rd, Chester, VT 05143

    Welcome to 938 Stigers Road, a masterpiece in the mountains! Discover a stunning fusion of artistry and craftsmanship in this exquisite timber frame home, tucked away in the serene beauty of the mountains.This residence is the inspired creation of a visionary artist and a skilled builder, resulting in a one-of-a-kind retreat where design and nature are in perfect harmony.Fall in love with

    Liz Moore Four Seasons Sotheby's Int'l Realty

    938 Stigers Rd, Chester, VT 05143
  • 841 Farrar Rd, Chester, VT 05143
    841 Farrar Rd, Chester, VT 05143
    841 Farrar Rd, Chester, VT 05143
    /35

    $199,000

    • 3 Beds
    • 1 Bath
    • 1,322 Sq Ft

    841 Farrar Rd, Chester, VT 05143

    Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for

    Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

    841 Farrar Rd, Chester, VT 05143
  • 663 Depot St, Chester, VT 05143
    663 Depot St, Chester, VT 05143
    663 Depot St, Chester, VT 05143
    /44

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    663 Depot St, Chester, VT 05143

    Experience the warmth of history with the ease of modern living at 663 Depot Street. This fully renovated 3-bedroom, 2-bath home offers historic charm with today’s updates. Since 2022, insulation, drywall, electrical, plumbing, HVAC, furnace, water heater, fixtures, countertops, cabinets, and appliances have all been replaced. The home's original wood flooring has been carefully refinished to

    Betsy Adamovich Real Broker LLC

    663 Depot St, Chester, VT 05143
  • 515 Main St, Chester, VT 05143
    515 Main St, Chester, VT 05143
    515 Main St, Chester, VT 05143
    /43

    $189,000

    • 4 Beds
    • 4 Baths
    • 3,024 Sq Ft

    515 Main St, Chester, VT 05143

    Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture,

    John Tolosky Barrett and Valley Associates Inc.

    515 Main St, Chester, VT 05143
  • 4877 Vt Route 103 N, Chester, VT 05143
    4877 Vt Route 103 N, Chester, VT 05143
    4877 Vt Route 103 N, Chester, VT 05143
    /56

    $450,000

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    4877 Vt Route 103 N, Chester, VT 05143

    Tucked along the scenic curves of Route 103 & surrounded by the rolling beauty of Chester, Vermont, this unique French Provincial–meets–Vermont cabin is more than just a house—it’s an invitation to breathe deeper, slow down, & reconnect with the rhythm of nature. Wake each morning to the soothing sound of a nearby creek & the scent of fresh mountain air drifting through the trees. Step outside

    Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
Vermont Chester

Houses for Sale in Chester, VT

Why Live in Chester

Chester, a quaint neighborhood in central Vermont, offers a close-knit community with a small-town charm. Residents can choose between living near the town center, close to local businesses, or on the outskirts with expansive land. The housing options include older Cape Cods and colonials from the early- to mid-1900s, ranch-style homes from the late-1900s, and contemporary houses built in the last 25 years. Chester’s rustic identity is complemented by numerous dirt backroads. The town features several attractions, including popular local restaurants like Country Girl Diner, Pizza Stone VT, MacLaomainn's Scottish Pub, and Southern Pie Cafe. Newer dining spots like Maria’s Mexican restaurant add to the variety. Essential shopping can be done at Smitty's Chester Market and Dollar General, with more options available in nearby Ludlow and Springfield. Chester Festival on the Green, held every September, celebrates the town’s art and culture with craft vendors, live music, and family activities. Outdoor amenities along Lovers Lane Road include a municipal pool, skatepark, playground, basketball court, disc golf course, tennis courts, and baseball diamonds. Chester Town Forest offers hiking trails like Butternut Hill Trail and Lost Mine Loop. The neighborhood is safer than the national average, making it a practical choice for families. Commuting is car-dependent, with State Route 11 providing access to Springfield, 8 miles east, and State Route 103 leading to Ludlow, 13 miles north. The Springfield Hospital is just over 7 miles away, and Albany International Airport is 88 miles south. Mud season from March to June can affect road conditions due to Vermont’s unique climate.
Learn more about living in Chester

Home Trends in Chester, VT

On average, homes in Chester, VT sell after 89 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, VT over the last 12 months is $390,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$390,000
Median Single Family Sale Price
$399,500
Median Townhouse Sale Price
$906,500
Average Price Per Sq Ft
$255
Number of Homes for Sale
16
Last 12 months Home Sales
40
Months of Supply
4.80
Median List Price
$462,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
0%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 19 houses for sale, offering an array of options for potential buyers. With houses priced between $189,000 to $1,650,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $462,000, while the average sale price is $510,767, offering insights into the local housing market. On average, houses spend 89 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chester, VT and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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