Chester, VT Multifamily Homes & Duplexes for Sale

/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
/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
/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
/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

Vermont Windsor County Chester

Why Live in Chester

Chester, Vermont, is a small-town community known for its quiet charm and close-knit atmosphere. Homebuyers can choose from a variety of home styles, including older Cape Cods and colonials, ranch-style homes, and contemporary houses, with options ranging from tightly arranged homes in the town center to sprawling properties on the outskirts. Chester's local dining scene features favorites like Country Girl Diner, Pizza Stone VT, and MacLaomainn's Scottish Pub, while Southern Pie Cafe offers delightful desserts. Residents enjoy recreational amenities along Lovers Lane Road, including a municipal pool, skatepark, and hiking trails in Chester Town Forest. The annual Chester Festival on the Green in September celebrates local art and culture with craft vendors and live performances. While Chester is car-dependent, commuters can access nearby towns via State Route 11 and 103, with Springfield Hospital 7 miles away and Albany International Airport 88 miles south. The area experiences a unique mud season from March to June, affecting travel on the numerous dirt roads. Chester's schools have average ratings, with Green Mountain Union High offering a low student-teacher ratio.

Learn more about living in Chester

Home Trends in Chester, VT

On average, homes in Chester, VT sell after 65 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, VT over the last 12 months is $295,000, down 51% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$295,000

Median Single Family Sale Price

$517,500

Average Price Per Sq Ft

$266

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.00

Median List Price

$595,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-51%

How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 4 multi-family homes for sale, providing an appealing investment opportunity for buyers. With multi-family homes priced between $189,000 to $650,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $595,000, while the average sale price is $428,125, offering insights into the local housing market. On average, multi-family homes spend 65 days listed before being sold. Multi-family homes include a variety of property types, from duplexes, triplexes, and fourplexes, to apartment complexes, all within a single building divided to accommodate multiple families living separately. These multi-family properties for sale offer investors the chance to generate rental income. Whether you're considering a duplex for a beginner investment or an apartment complex for a more substantial venture, there are investment properties available to meet your requirements. Explore the range of multi-family homes for sale in Chester, VT.

Chester Types of Homes for Sale

Chester Homes for Sale

More About Living in Chester

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

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.