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Andover, VT Homes for Sale

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  • /42

    $3,150,000

    • Land
    • 506 Acres
    • $6,225 per Acre

    Markham Mountain, Andover, VT 05143

    Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

    Story Jenks LANDVEST

    Markham Mountain, Andover, VT 05143
  • /42

    $3,150,000

    • Land
    • 506 Acres
    • $6,225 per Acre

    00 Marsh Cross Rd, Andover, VT 05143

    Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

    Story Jenks LandVest, Inc/Woodstock

    00 Marsh Cross Rd, Andover, 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
  • /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
  • /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
  • /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
  • /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
  • /60

    $889,000

    • 3 Beds
    • 2 Baths
    • 3,310 Sq Ft

    201 Spruce Dr, Chester, VT 05143

    Situated on more than five acres of rolling Vermont hillside, this three bedroom, two bath home offers effortless access to Okemo, Stratton, Bromley, and Magic ski resorts and is being sold turnkey. Designed for those who value both comfort and connection to the outdoors, the home delivers updated living space surrounded by peaceful countryside. Nearby VAST trail access and a sweeping wraparound

    Mendi Michael Engel & Völkers Okemo

    201 Spruce Dr, Chester, VT 05143
  • /21

    $150,000

    • Land
    • 13.96 Acres
    • $10,745 per Acre

    0 Valley View Dr Unit 5009431, Andover, VT 05143

    Great Value in a great setting ! 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

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    0 Valley View Dr Unit 5009431, 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
  • /17

    $485,000

    • Land
    • 26.99 Acres
    • $17,970 per Acre

    00 Valley View Dr, Andover, VT 05143

    A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    00 Valley View Dr, 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
  • /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

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.

Frequently Asked Questions

What is the average home price in Andover, VT?
Homes for sale in Andover, VT have an average home price of $2,137,800.
Are home prices dropping in Andover?
Yes, home prices in Andover are down 47% in the last 12 months.
How many homes have sold over the last 12 months in Andover, VT?
4 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 $695,000. If you put a 20% down payment of $139,000 and had a 30-year fixed mortgage with an interest rate of 6.09%, your estimated principal and interest payment would be $3,370 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $144K 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

Housing Trends

Median Sale Price
$445,000
Median Single Family Sale Price
$600,000
Average Price Per Sq Ft
$349
Number of Homes for Sale
1
Last 12 months Home Sales
4
Months of Supply
3.00
Median List Price
$695,000
Median Change From 1st List Price
16%
Median Home Sale Price YoY Change
-54%
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