27

Chester, VT Homes 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
  • Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson Rd, Chester, VT 05143
    /13

    $129,000

    • Land
    • 3.24 Acres
    • $39,815 per Acre

    Lot 3 Mattson Rd, Chester, VT 05143

    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 hillside that levels out

    Jessica Citera Cummings & Co

    Lot 3 Mattson 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

    • 3 Beds
    • 3 Baths
    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VTDiscover 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

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, 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
  • 423 Main St, Chester, VT 05143
    423 Main St, Chester, VT 05143
    423 Main St, Chester, VT 05143
    /36

    $575,000

    • 6 Beds
    • 5 Baths
    • 3,217 Sq Ft

    423 Main St, Chester, VT 05143

    Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing

    Betty McEnaney Diamond Realty

    423 Main St, 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

    $275,000

    • Land
    • 91 Acres
    • $3,022 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre 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

    Daire Gibney Barrett and Valley Associates Inc.

    000 Green Mountain Turnpike, Andover, VT 05143
  • 1377 Vermont 103, Chester, VT 05143
    1377 Vermont 103, Chester, VT 05143
    1377 Vermont 103, Chester, VT 05143
    /40

    $495,000

    • 2,280 Sq Ft

    1377 Vermont 103, Chester, VT 05143

    Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business. There are 2 separate buildings. One needs to be finished, main building 3 floor could be finished for more living space.

    Mike England Michael England Real Estate

    1377 Vermont 103, Chester, VT 05143
  • 515 Main St, Chester, VT 05143
    515 Main St, Chester, VT 05143
    515 Main St, Chester, VT 05143
    /14

    $189,000

    • 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 with one 2 bedroom apartment, one 1 bedroom apartment and two studio apartments. The house is in need of renovation however, the style and location would lend well to that investment.

    John Tolosky Barrett and Valley Associates Inc.

    515 Main St, Chester, VT 05143
  • 0 Snell Rd, Chester, VT 05143
    0 Snell Rd, Chester, VT 05143
    0 Snell Rd, Chester, VT 05143
    /24

    $95,000

    • Land
    • 10 Acres
    • $9,135 per Acre

    0 Snell Rd, Chester, VT 05143

    This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Utility pole is at the road

    Geralyn Donohue Engel & Völkers Okemo

    0 Snell Rd, 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
  • 00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    /26

    $229,000

    • Land
    • 28 Acres
    • $8,237 per Acre

    00 Quarry Rd, Chester, VT 05143

    Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel

    Geralyn Donohue Engel & Völkers Okemo

    00 Quarry Rd, Chester, VT 05143
  • 419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    /12

    $259,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    419 Coach Rd, Chester, VT 05143

    Amy Carson Lowe's Real Estate, LLC

    419 Coach Rd, Chester, VT 05143
Vermont Chester

Real Estate & Homes 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

Frequently Asked Questions

What is the average home price in Chester, VT?
Homes for sale in Chester, VT have an average home price of $626,382.
How many homes have sold over the last 12 months in Chester, VT?
38 homes have sold in Chester, VT over the last 12 months.
What are the most popular zip codes in Chester, VT?
The most popular zip codes in Chester, VT include 05149, 03743, 05143, 05156 and 05343.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $484,000. If you put a 20% down payment of $96,800 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $2,520 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $108K a year to afford the median home price in Chester.
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 Trends in Chester, VT

On average, homes in Chester, VT sell after 91 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 $397,500, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$397,500
Median Single Family Sale Price
$400,000
Median Townhouse Sale Price
$906,500
Average Price Per Sq Ft
$253
Number of Homes for Sale
18
Last 12 months Home Sales
38
Months of Supply
5.70
Median List Price
$484,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-5%
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