5

Andover, VT Houses for Sale

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  • 2029 N Hill Rd, Chester, VT 05143
    2029 N Hill Rd, Chester, VT 05143
    2029 N Hill Rd, Chester, VT 05143
    /36

    $369,000

    • 5 Beds
    • 1 Bath
    • 2,243 Sq Ft

    2029 N Hill Rd, Chester, VT 05143

    Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the

    Daire Gibney Barrett and Valley Associates Inc.

    2029 N Hill Rd, Chester, VT 05143
  • 127 Trombley Rd, Chester, VT 05143
    127 Trombley Rd, Chester, VT 05143
    127 Trombley Rd, Chester, VT 05143
    /20

    $449,000

    • 5 Beds
    • 1 Bath
    • 2,856 Sq Ft

    127 Trombley Rd, Chester, VT 05143

    Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a

    Daire Gibney Barrett and Valley Associates Inc.

    127 Trombley Rd, Chester, VT 05143
  • 1979 N Hill Rd, Chester, VT 05143
    1979 N Hill Rd, Chester, VT 05143
    1979 N Hill Rd, Chester, VT 05143
    /42

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    1979 N Hill Rd, Chester, VT 05143

    Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

    Geralyn Donohue Engel & Völkers Okemo

    1979 N Hill Rd, Chester, VT 05143
  • 3800 Weston-Andover Rd, Andover, VT 05143
    3800 Weston-Andover Rd, Andover, VT 05143
    3800 Weston-Andover Rd, Andover, VT 05143
    /41

    $5,950,000

    • 8 Beds
    • 7.5 Baths
    • 10,062 Sq Ft

    3800 Weston-Andover Rd, Andover, VT 05143

    The ultimate family compound, award nominated video tour. This fully furnished and equipped luxury property is located in Andover, Vermont, set on 384 acres in the iconic Green Mountains, offering a rare blend of nature’s bounty, seclusion, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • 4351 Vermont 11, Chester, VT 05143
    4351 Vermont 11, Chester, VT 05143
    4351 Vermont 11, Chester, VT 05143
    /20

    $149,900

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    4351 Vermont 11, Chester, VT 05143

    Almost there! This owner has taken this property to a new level...had the septic discovered and has a report, upgraded the electric entrance and added an EV station, laid flooring, opened up a wall for a much nicer open concept, cleaned and made into a little cottage for skiing, nature loving or just plain home. There are rain barrels for water, let nature fill them up or hire the local water

    Christine Lewis Brattleboro Area Realty

    4351 Vermont 11, Chester, VT 05143
Vermont Windsor County Andover

Houses for Sale in Andover, VT

Why Live in Andover

Andover, VT, offers a rural lifestyle in the Green Mountains, characterized by winding country roads through dense forests and farmland. With a population of less than 1,000, homes in Andover are typically traditional-style, built from the mid-1900s to contemporary houses from the past 25 years. Properties often sit on expansive lots ranging from 2 to over 100 acres, providing a quiet retreat. The area is car-dependent, with State Route 11 serving as the main thoroughfare connecting Andover to Springfield. Vermont’s mud season from March to June can make the dirt roads challenging, with potential hazardous conditions and road closures. Outdoor attractions are found in neighboring towns, such as Chester Town Forest with its hiking trails, Lowell Lake State Park in Londonderry for boating and fishing, and Okemo Mountain Resort, 10 miles north, offering extensive skiing and snowboarding trails. For shopping and dining, residents travel to Ludlow, 10 miles north, or Springfield, 15 miles east, where they can find grocery stores, local restaurants, and retail outlets. The Chester Fall Festival, held each September in nearby Chester, celebrates local art and culture with craft vendors, live music, and family activities.

Learn more about living in Andover

Home Trends in Andover, VT

On average, homes in Andover, VT sell after 148 days on the market compared to the national average of 53 days. The median sale price for homes in Andover, VT over the last 12 months is $722,500, down 23% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$722,500
Median Single Family Sale Price
$845,000
Average Price Per Sq Ft
$380
Number of Homes for Sale
1
Last 12 months Home Sales
4
Months of Supply
3.00
Median List Price
$950,000
Median Change From 1st List Price
12%
Median Home Sale Price YoY Change
-23%
How to Buy a Home How to Finance a Home How to Sell a Home

In Andover, there are currently 5 houses for sale, offering an array of options for potential buyers. With houses priced between $149,900 to $5,950,000, there's a range to accomodate every budget. As of December, 2025 the median home price in Andover is $950,000, while the average sale price is $675,000, offering insights into the local housing market. On average, houses spend 148 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 Andover, VT and find the perfect place to call home.

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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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