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Chester, VT Homes for Rent

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  • 3148 Popple Dungeon Rd, Chester, VT 05143
    3148 Popple Dungeon Rd, Chester, VT 05143
    /2

    $1,400 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    3148 Popple Dungeon Rd, Chester, VT 05143

    Single family ranch located a short distance from town. 2 bedrooms, livingroom, eat in kitchen and full bath with a covered walkway to a one car garage. Washer/dryer hookups. $1,400.00 per month plus utilities. Available October 1, 2026. References and credit check required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    3148 Popple Dungeon Rd, Chester, VT 05143
  • 659 Davidson Hill Rd Unit 1, Chester, VT 05143
    659 Davidson Hill Rd Unit 1, Chester, VT 05143
    659 Davidson Hill Rd Unit 1, Chester, VT 05143
    /18

    $1,795 Per Month

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    659 Davidson Hill Rd Unit 1, Chester, VT 05143

    CURRENTLY UNDER CONTRACTUpper floor apartment in a quiet split level between North Springfield, VT and Chester. Take advantage of a large yard in close proximity to many local employers or enjoy the nearby Springweather Dam and Nature Trails. This apartment has 2 good size bedrooms and 2 baths and is freshly painted with new flooring. It also features a spacious eat in

    659 Davidson Hill Rd Unit 1, Chester, VT 05143
Vermont Windsor County

Homes for Rent in Chester, VT

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

Frequently Asked Questions

How much does it cost to rent a home in Chester, VT?
The median rent for a home in Chester, VT is $1,597 per month, though prices vary by neighborhood, size, and property type. As of September 2026, condos tend to be the most affordable option while single-family homes are currently more expensive.
How much do you need to make to afford rent in Chester, VT?
To comfortably afford the median rent in Chester, VT, a household needs to earn roughly $63,880 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,597 per month in Chester, VT, renters typically need to show $4,791 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Chester, VT?
In Chester, VT, the price-to-rent ratio is 19.3, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Trends in Chester, VT

There are currently 2 homes available for rent in Chester, VT. The median rent is $1,597 per month, with single-family homes renting at $2,100 and condos at $1,448.

Rental Home Trends

Number of Homes for Rent
2
Median Rent
$1,597
Median Single Family Home Rent
$2,100
Median Condo Rent
$1,448
How to Rent a Home

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