Chester, VT homes for sale & real estate

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ABOUT THIS HOME
Chester, VT Homes for Sale
Bring Your Vision to Life in Beautiful Chester, Vermont! Discover the potential of this partially constructed A-frame home nestled on approximately 2 acres along VT Route 11 in scenic Chester, Vermont. Offering approximately 980 square feet of planned living space, this 3-bedroom, 2-bathroom property presents an exciting opportunity for investors, builders, contractors, or buyers looking to create a personalized Vermont retreat. The renovation is awaiting a complete build-out, including windows, doors, and all interior and exterior finish materials, allowing the next owner to take the project from its current stage to a finished home tailored to their vision. With its distinctive A-frame d

$114,900

3 beds2 baths980 sq ft

4351 Vermont Route 11 W, Chester, VT 05143

2 acre lot • Built 1968 • Listed 20 days

ABOUT THIS HOME
Chester, VT Homes for Sale
MOVE-IN READY! Chester, VT, One-Level Living, 0.25 Acre Level Yard, Amazing Outdoor Space! Enjoy easy, comfortable one-level living on a quiet circle in charming Chester, Vermont! This inviting home features a bright living room with a large picture window, an eat-in kitchen with abundant cabinet and counter space, and a well-built front deck. The fabulous front and back decks provide wonderful spaces for outdoor entertaining, relaxing, and enjoying the sunshine! The spacious lower-level recreation area offers endless possibilities, complete with a workshop, laundry area, and abundant storage. Additional features include public water and sewer, newer oil tank, paved driveway, a sunny, lev

$240,000

2 beds1 bath912 sq ft

148 Kevadus Cir, Chester, VT 05143

Level yard • Front deck • Back decks

ABOUT THIS HOME
Chester, VT Homes for Sale
This cozy home presents so many opportunities-Live here, vacation here, rental property, renovate as you want and flip, ski home! Offering 2 bedrooms, 1 full bathroom, eat in kitchen/dining room, and living room. Outside is a great 1 car garage with plenty of space for all your tools, lawnmower, etc. Set right in the town of Chester in short walking distance to stores or the town green with wonderful coffee shops and other great shops! Close to ski areas, hospital, schools, and much more, whatever you are looking for this single floor home could check all your boxes! Or would make a great investment property with a little work! Call for your appointment today.

$129,900

2 beds1 bath756 sq ft

473 Elm St, Chester, VT 05143

Eat in kitchen • Investment property • 1 car garage

$549,000

4 beds2 baths2,190 sq ft

204 Fletcher Rd, Chester, VT 05143

2.03 acre lot • 2 garage spots • Built 1977

ABOUT THIS HOME
Chester, VT Homes for Sale
Welcome to this comfortable Cape-style home in Chester, Vermont, offering a wonderful combination of classic charm, practical features, and flexible living space. Whether you’re looking for a place to call home or a property with room to make your own, this home has plenty to offer! The property features a durable standing seam metal roof, double-pane vinyl windows, and beautiful hardwood floors throughout most of the main level. The inviting layout provides comfortable everyday living, while the level lot offers usable outdoor space for gardening, relaxing, entertaining, or enjoying the seasons in Vermont. An oversized one car garage provides convenient parking along with additional

$269,000

4 beds1 bath1,324 sq ft

426 Vermont Route 103, Chester, VT 05143

Usable yard • Level lot • Finished office

Property at 1065 Hill Top Rd, Andover, VT 05143, 3 beds, 2.5 baths

$499,000

3 beds2.5 baths2,636 sq ft

1065 Hill Top Rd, Andover, VT 05143

Property at 470 Middletown Rd, Andover, VT 05143, 4 beds, 2 baths

$1,300,000

4 beds2 baths2,360 sq ft

470 Middletown Rd, Andover, VT 05143

Property at 979 Andover Ridge Rd, Andover, VT 05143, 3 beds, 3 baths

$990,000

3 beds3 baths2,167 sq ft

979 Andover Ridge Rd, Andover, VT 05143

Property at 3208 Green Mountain Tpke, Chester, VT 05143, 3 beds, 2 baths

$425,000

3 beds2 baths1,626 sq ft

3208 Green Mountain Tpke, Chester, VT 05143

Property at 3319 E Hill Rd, Ludlow, VT 05149, 4 beds, 3.5 baths

$649,900

4 beds3.5 baths2,576 sq ft

3319 E Hill Rd, Ludlow, VT 05149

Property at 296 North St, Chester, VT 05143, 3 beds, 2 baths

$575,000

3 beds2 baths1,788 sq ft

296 North St, Chester, VT 05143

Property at 168 Chandler Rd, Chester, VT 05143, 3 beds, 2 baths

$627,000

3 beds2 baths2,204 sq ft

168 Chandler Rd, Chester, VT 05143

Property at 96 Lower Bartonsville Rd, Chester, VT 05143, 3 beds, 2 baths

$360,000

3 beds2 baths1,312 sq ft

96 Lower Bartonsville Rd, Chester, VT 05143

Property at 3800 Weston Andover Rd, Andover, VT 05143, 8 beds, 7.5 baths

$4,150,000

8 beds7.5 baths10,062 sq ft

3800 Weston Andover Rd, Andover, VT 05143

Property at 3537 Popple Dungeon Rd, Chester, VT 05143, 2 beds, 1 bath

$225,000

2 beds1 bath930 sq ft

3537 Popple Dungeon Rd, Chester, VT 05143

Property at 548 Crow Hill Rd, Chester, VT 05143, 4 beds, 2 baths

$599,000

4 beds2 baths1,908 sq ft

548 Crow Hill Rd, Chester, VT 05143

Property at 23 School St, Chester, VT 05143

$649,000

— beds— baths13,788 sq ft

23 School St, Chester, VT 05143

Property at 3019 Popple Dungeon Rd, Chester, VT 05143, 1 bed, 1 bath

$169,000

1 bed1 bath200 sq ft

3019 Popple Dungeon Rd, Chester, VT 05143

Property at 3 Eldredge Rd, Chester, VT 05143, 5 beds, 5 baths

$1,600,000

5 beds5 baths6,118 sq ft

3 Eldredge Rd, Chester, VT 05143

Property at 81 Main St, Chester, VT 05143, 5 beds, 4 baths

$445,000

5 beds4 baths3,865 sq ft

81 Main St, Chester, VT 05143

Property at 3781 Flamstead Rd, Chester, VT 05143, 3 beds, 2 baths

$225,000

3 beds2 baths1,500 sq ft

3781 Flamstead Rd, Chester, VT 05143

Property at 758 Weston Andover Rd, Andover, VT 05143, 4 beds, 3.5 baths

$495,000

4 beds3.5 baths2,656 sq ft

758 Weston Andover Rd, Andover, VT 05143

Property at 1302 Popple Dungeon Rd, Chester, VT 05143, 5 beds, 5 baths

$1,349,000

5 beds5 baths5,400 sq ft

1302 Popple Dungeon Rd, Chester, VT 05143

Property at 1144 Potash Brook Rd, Chester, VT 05143, 2 beds, 1 bath

$75,000

2 beds1 bath620 sq ft

1144 Potash Brook Rd, Chester, VT 05143

Property at 76 Goldthwaite Rd, Chester, VT 05143, 4 beds, 3 baths

$1,200,000

4 beds3 baths3,308 sq ft

76 Goldthwaite Rd, Chester, VT 05143

Property at 40 Fenton Rd, Chester, VT 05143, 4 beds, 2.5 baths

$399,000

4 beds2.5 baths2,148 sq ft

40 Fenton Rd, Chester, VT 05143

Property at 201 Spruce Dr, Andover, VT 05143, 3 beds, 2 baths

$879,999

3 beds2 baths3,310 sq ft

201 Spruce Dr, Andover, VT 05143

Property at 3630 Vt Route 103 N, Chester, VT 05143, 3 beds, 3 baths

$650,000

3 beds3 baths4,324 sq ft

3630 Vt Route 103 N, Chester, VT 05143

Property at 0 Remington Rd, Chester, VT 05143

$55,000

Land1.52 acres (lot)

0 Remington Rd, Chester, VT 05143

Property at VT Route 103 Lot 4, Chester, VT 05143

$105,000

Land3.35 acres (lot)

VT Route 103 Lot 4, Chester, VT 05143

Property at VT Route 103 Lot 3, Andover, VT 05143

$105,000

Land3.28 acres (lot)

VT Route 103 Lot 3, Andover, VT 05143

Property at 1992 Andover Ridge Rd, Andover, VT 05143, 3 beds, 2 baths

$325,000

Land24.50 acres (lot)

1992 Andover Ridge Rd, Andover, VT 05143

Property at 1475 Brockways Mill Rd, Athens, VT 05143

$299,000

Land74.79 acres (lot)

1475 Brockways Mill Rd, Athens, VT 05143

Property at 00 Simonsville Rd, Andover, VT 05143

$85,000

Land3.99 acres (lot)

00 Simonsville Rd, Andover, VT 05143

Property at 0 Linden Way, Chester, VT 05143

$79,000

Land5.00 acres (lot)

0 Linden Way, Chester, VT 05143

Property at 00 Quarry Rd, Chester, VT 01543

$229,000

Land27.80 acres (lot)

00 Quarry Rd, Chester, VT 01543

Property at 00 Snell Rd, Chester, VT 05143

$87,500

Land10.40 acres (lot)

00 Snell Rd, Chester, VT 05143

Property at 000 Green Mountain Tpke, Chester, VT 05143

$220,000

Land84.00 acres (lot)

000 Green Mountain Tpke, Chester, VT 05143

Property at 00 Little Pond Rd, Andover, VT 05143

$630,000

Land10.03 acres (lot)

00 Little Pond Rd, Andover, VT 05143

Property at TBD Farrar Rd, Chester, VT 05143

$74,500

Land16.24 acres (lot)

TBD Farrar Rd, Chester, VT 05143

Property at 427 Depot St, Chester, VT 05143, 5 beds, 1.5 baths

$100,000

Land0.55 acre (lot)

427 Depot St, Chester, VT 05143

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Average home prices near Chester, VT

Cities

Cavendish homes for sale
$692,000
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$670,000
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$852,000
North Springfield homes for sale
$299,900
Bellows Falls homes for sale
$232,000
Springfield homes for sale
$254,950
Perkinsville homes for sale
Walpole homes for sale
$642,450
Jamaica homes for sale
$425,000
Westminster homes for sale
$427,000
South Londonderry homes for sale
$499,000
Ludlow homes for sale
$599,000
Claremont homes for sale
$344,950
Windsor homes for sale
$400,000

Zip Codes
Minor Civil Divisions

05143 homes for sale
$524,000

Chester, VT real estate trends

$449K

Sale price

+20.5%
since last year

$172

Sale $/sq ft

+40.4%
since last year

Over list price

0.1%

Days on market

Down payment

—

Total homes sold

See more Chester, VT market insights

More to explore in Chester, VT

How to buy a house in Chester, VT

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First-time homebuyer's guide

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Middlebury homes for sale
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Bennington homes for sale
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Norwich homes for sale
$939,000

Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Fri Nov 06 2026 on the search page

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