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Newest Homes for Sale in Andover, VT

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  • 1269 Howard Hill Rd, Chester, VT 05143
    1269 Howard Hill Rd, Chester, VT 05143
    1269 Howard Hill Rd, Chester, VT 05143
    /48

    $899,000

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft

    1269 Howard Hill Rd, Chester, VT 05143

    Discover a truly one-of-a-kind Vermont retreat set on 10 acres of peaceful woodland and open meadow. Originally built as a family-run maple sugar shack, this architect-designed home has been thoughtfully reimagined and newly completed, seamlessly blending rustic charm with contemporary comfort to create a warm and inviting hideaway unlike anything else on the market. Post-and-beam construction,

    Cheyanne Pugliese

    1269 Howard Hill Rd, Chester, VT 05143
  • 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
  • 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
  • 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
  • 00 Vermont 103, Andover, VT 05143
    00 Vermont 103, Andover, VT 05143
    00 Vermont 103, Andover, VT 05143
    /60

    $200,000

    • Land
    • 6.63 Acres
    • $30,166 per Acre

    00 Vermont 103, Andover, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Lange & Lange

    00 Vermont 103, Andover, VT 05143
  • 00 Hillcrest Dr, Andover, VT 05143
    00 Hillcrest Dr, Andover, VT 05143
    00 Hillcrest Dr, Andover, VT 05143
    /15

    $85,000

    • Land
    • 4.05 Acres
    • $20,988 per Acre

    00 Hillcrest Dr, Andover, VT 05143

    Ready to Build in Southern Vermont! Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for remote work

    Daire Gibney Barrett and Valley Associates Inc.

    00 Hillcrest Dr, Andover, VT 05143
  • 00 E Hill Rd, Andover, VT 05143
    00 E Hill Rd, Andover, VT 05143
    00 E Hill Rd, Andover, VT 05143
    /11

    $85,000

    • Land
    • 15.68 Acres
    • $5,421 per Acre

    00 E Hill Rd, Andover, VT 05143

    Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

    Daire Gibney Barrett and Valley Associates Inc.

    00 E Hill Rd, Andover, 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
  • 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
  • 0 Valley View Dr Unit 5009431, Andover, VT 05143
    0 Valley View Dr Unit 5009431, Andover, VT 05143
    0 Valley View Dr Unit 5009431, Andover, VT 05143
    /21

    $170,000

    • Land
    • 13.96 Acres
    • $12,178 per Acre

    0 Valley View Dr Unit 5009431, Andover, VT 05143

    Set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes a state-approved wastewater permit and access to a community leach field,

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    0 Valley View Dr Unit 5009431, Andover, VT 05143
Vermont Windsor County Andover

Newest Listings for Sale in Andover, VT

Frequently Asked Questions

What is the average home price in Andover, VT?
Homes for sale in Andover, VT have an average home price of $1,944,000.
Are home prices dropping in Andover?
Yes, home prices in Andover are down 37% in the last 12 months.
How many homes have sold over the last 12 months in Andover, VT?
5 homes have sold in Andover, VT over the last 12 months.
What are the most popular zip codes in Andover, VT?
The most popular zip codes in Andover, VT include 05143, 05149, 05161, 05148 and 05155.
How much do you need to make to afford a house in Andover?
The median home price in Andover is $822,500. If you put a 20% down payment of $164,500 and had a 30-year fixed mortgage with an interest rate of 6.16%, your estimated principal and interest payment would be $4,010 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $172K a year to afford the median home price in Andover. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Andover, VT?
Andover, VT has highly rated public and private schools. Some of the best schools in Andover based on Niche Grades are Ludlow Elementary School, Flood Brook School and Green Mountain Union High School. Browse all the schools in Andover, VT to learn more.

Home Trends in Andover, VT

On average, homes in Andover, VT sell after 230 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 $600,000, down 36% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$600,000
Median Single Family Sale Price
$722,500
Average Price Per Sq Ft
$335
Number of Homes for Sale
1
Last 12 months Home Sales
5
Months of Supply
2.40
Median List Price
$822,500
Median Change From 1st List Price
14%
Median Home Sale Price YoY Change
-36%
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