Andover, VT Homes

• 

  

  

  /37

  $459,000

  • 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
• 

  

  

  /36

  $1,400,000 Sold Aug 27, 2025

  • 2,614 Sq Ft
  • $536/SF
  • 42 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2011

  938 Stigers Rd, Chester, VT 05143

  Welcome to 938 Stigers Road, a masterpiece in the mountains! Discover a stunning fusion of artistry and craftsmanship in this exquisite timber frame home, tucked away in the serene beauty of the mountains.This residence is the inspired creation of a visionary artist and a skilled builder, resulting in a one-of-a-kind retreat where design and nature are in perfect harmony.Fall in love with

  Liz Moore Four Seasons Sotheby's Int'l Realty

  938 Stigers Rd, Chester, VT 05143
• 

  

  

  /8

  Not Listed For Sale

  • 3 Beds

  0 Hillcrest Dr, Chester, VT 05143

  0 Hillcrest Dr, Chester, VT 05143
• 

  

  

  /28

  $485,000

  • Land
  • 57.2 Acres
  • $8,479 per Acre

  1809 Marsh Hill Rd, Andover, VT 05143

  This is a one-of-a-kind legacy property, off the beaten path and accessible to everything that makes Southern Vermont an incredible place to call home. The 57.2 acres offer the perfect mix with hardwoods (maples and more), pine groves, open meadows, a pond spanning apprx 1/4-acre, and spectacular southern views and all-day sunlight. Come build your Vermont dream house and be assured of total

  Claudia Harris Mary Mitchell Miller Real Estate

  1809 Marsh Hill Rd, Andover, VT 05143
• 

  

  

  /60

  $677,000 Sold Aug 15, 2025

  • 2,456 Sq Ft
  • $276/SF
  • 6 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1878

  3236 Weston-Andover Rd, Chester, VT 05143

  Set on a stunning, level 7.38-acre parcel, this beautifully updated farmhouse is turnkey and full of character, comfort, and space! The convenient mudroom offers built-in shelving for your gear and leads into a lovely country kitchen featuring handmade cabinetry, granite countertops, a butcher block island, and a cozy breakfast bar. Step out to the charming front porch to enjoy your morning

  Mendi Michael Engel & Völkers Okemo

  3236 Weston-Andover Rd, Chester, VT 05143
• 

  

  /40

  Est $686,475 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,040 Sq Ft

  201 Spruce Dr, Chester, VT 05143

  201 Spruce Dr, Chester, 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 Rachael Rogala Inc.

  00 Vermont 103, Andover, VT 05143
• 

  

  /57

  $399,000 Sold Jul 31, 2025

  • 1,402 Sq Ft
  • $285/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  387 Weston-Andover Rd, Chester, VT 05143

  Nestled on a peaceful hillside in the town of Andover, this well-maintained home offers the soothing sounds of the Andover Branch River as your daily backdrop. Enjoy the ease of one-level living with three bedrooms, a full bathroom, and a comfortable main living space perfect for relaxing or entertaining.The walkout basement adds even more potential. Already underway is a second full

  Jessica Citera Cummings & Co

  387 Weston-Andover Rd, Chester, VT 05143
• 

  

  /40

  Est $360,656 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,087 Sq Ft

  42 Cobb Rd, Chester, VT 05143

  42 Cobb Rd, Chester, VT 05143
• 

  

  /25

  $359,000

  • 3 Beds
  • 1,504 Sq Ft

  1749 Middletown Rd, Andover, VT 05143

  Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1749 Middletown Rd, Andover, VT 05143
• 

  

  /60

  $40,000 Sold Jul 11, 2025

  • Land
  • 5 Acres
  • $8,000 per Acre

  • 77 Days On Market

  00 Boone Rd, Andover, VT 05143

  Rustic Vermont Getaway | Off-Grid Land on Snowmobile TrailEscape to the peace and quiet of rural Vermont with this unique parcel of off-grid land, perfect for a seasonal retreat or outdoor adventure basecamp. It is located off a Class 4 road, this remote property offers an authentic back-to-nature experience—accessible only in the summer months and nestled directly on a maintained

  Rachael Rogala Rachael Rogala Inc.

  00 Boone Rd, Andover, VT 05143
• 

  

  /35

  Est $439,972 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,171 Sq Ft

  351 Lovejoy Brook Rd, Ludlow, VT 05149

  351 Lovejoy Brook Rd, Ludlow, VT 05149
• 

  

  /15

  $94,500

  • Land
  • 4.05 Acres
  • $23,333 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

  Daire Gibney Barrett and Valley Associates Inc.

  00 Hillcrest Dr, Andover, VT 05143
• 

  

  /59

  $280,000 Sold Jun 24, 2025

  • 1,134 Sq Ft
  • $247/SF
  • 473 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1983

  87 Trombley Rd, Andover, VT 05143

  Looking for privacy and a peaceful piece of Vermont, high on a hill, to call your own? Look no further than this 17+ beautiful acres at the dead end of a private road. Already in place is a 2 bedroom, 1 bathroom manufactured home with power, septic (it is already in place for a 3 bedroom house), and a drilled well. Live in the home already in place or just stay in it while you build your dream

  Erin Kendall EXP Realty

  87 Trombley Rd, Andover, VT 05143
• 

  

  /39

  Est $844,349 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,592 Sq Ft

  898 N Hill Rd, Andover, VT 05143

  898 N Hill Rd, Andover, VT 05143
• 

  

  /32

  $2,250,000

  • 2 Beds
  • 4 Baths
  • 3,514 Sq Ft

  611 Simmons Rd, Chester, VT 05143

  Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

  Dia Jenks LandVest, Inc/Woodstock

  611 Simmons Rd, Chester, VT 05143
• 

  

  /54

  $540,000 Sold May 23, 2025

  • 1,456 Sq Ft
  • $371/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  316 Little Pond Rd, Chester, VT 05143

  Charming Vermont Chalet for Sale in the township of Andover- 11.48 Private Acres near Ski Resorts & Lowell Lake State ParkExperience the best of rural character blended with the finest in modern amenities in this well-cared-for Vermont chalet. This charming retreat is ideal as a ski house, investment property, or full-time getaway.Inside, you’ll find an open-plan living space with vaulted

  Nick Sicard EXP Realty

  316 Little Pond Rd, Chester, VT 05143
• 

  

  /39

  Est $509,333 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft

  2358 N Hill Rd, Chester, VT 05143

  2358 N Hill Rd, Chester, VT 05143
• 

  

  /23

  $80,000

  • Land
  • 3.99 Acres
  • $20,050 per Acre

  00 Simonsville Rd, Andover, VT 05143

  3.99 +/- acres in Andover close to year round recreation of surrounding towns. This lot was approved by Vt ww dept. in 2008 for a 4 bedroom home and has being updated with a new survey and a revised engineered plan with relocation of the proposed leach field is in process. Located along almost 1000' of the Williams River, after two major storm events, this lot has not lost much ground. A driveway

  Geralyn Donohue Engel & Völkers Okemo

  00 Simonsville Rd, Andover, VT 05143
• 

  

  /37

  $600,000 Sold May 09, 2025

  • 2,076 Sq Ft
  • $289/SF
  • 575 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2008

  43 Lee Way, Andover, VT 05143

  Turn-key and Central to 4 ski areas, this beautifully renovated Cape sits on 10.5 acres with picturesque views. You'll enjoy the location just 20 minutes to Stratton, Okemo and Bromley. But most importantly, you'll appreciate the new fit and finish: new wood flooring, stone faced hearth, new Kitchenaid appliance package, interior painting and lighting. And it doesn't stop there, new gravel

  Britt Wohler

  43 Lee Way, Andover, VT 05143
• 

  

  /38

  Est $735,619 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  2401 N Hill Rd, Chester, VT 05143

  2401 N Hill Rd, Chester, VT 05143
• 

  

  /29

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  81 Trombley Rd, Andover, VT 05143

  This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready and just waiting for your finishing touches! It has a wonderful level yard with plenty of space for gardens, room to play, or put in a camp fire to sit around on a lovely Vermont evening. There is an additional gravel pad in place that you could put a tiny home as a rental opportunity or a guest house when

  Erin Kendall EXP Realty

  81 Trombley Rd, Andover, VT 05143
• 

  

  /10

  $150,000 Sold Mar 07, 2025

  • Land
  • 10.18 Acres
  • $14,735 per Acre

  • 468 Days On Market

  0 Spruce Dr Unit 4973323, Andover, VT 05143

  Nestled in the picturesque town of Andover, Vermont, this remarkable 10+ acre parcel of land offers an unparalleled opportunity to create your dream retreat amidst the tranquility of nature. Located on a quiet country road, this parcel is a blank canvas for your vision of a rustic escape. An easy commute to the towns of Chester, Ludlow, and Londonderry for shopping, restaurants, and exploring,

  Alan DeAngelo Element Real Estate

  0 Spruce Dr Unit 4973323, Andover, VT 05143
• 

  

  /26

  Est $489,158 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  331 Chauncey Rd, Andover, VT 05149

  331 Chauncey Rd, Andover, VT 05149
• 

  

  /11

  $99,000

  • Land
  • 15.68 Acres
  • $6,314 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
• 

  

  /53

  $499,000 Sold Feb 03, 2025

  • 2,650 Sq Ft
  • $188/SF
  • 229 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1820

  566 Simonsville Rd, Chester, VT 05143

  The historic Jaquith House is located in the Andover settlement of Simonsville on Rte 11. This historical brick federal 3 bedroom, 2.5 bath home on 6.85 +/- acres has potential for either a vacation home with guest house, year round residence or investment property. The two story double-walled brick home has original features such as eyebrow windows and 3 chimneys and has been thoughtfully

  Geralyn Donohue Engel & Völkers Okemo

  566 Simonsville Rd, Chester, VT 05143
• 

  

  /18

  Est $129,158 Not Listed For Sale

  2267 N Hill Rd, Andover, VT 05143

  2267 N Hill Rd, Andover, VT 05143
• 

  

  /5

  $80,000

  • Land
  • 4.3 Acres
  • $18,605 per Acre

  00 N Hill Rd, Andover, VT 05143

  The first step in building your Vermont Dream home is finding the perfect piece of land. Look no further! Situated on quiet country road of North Hill this parcel offers great building site, quiet location, easy access to skiing at Vail/Okemo resort (only minutes away), VAST access, close to Weston village with the Vermont Country Store and the Weston Playhouse. Soil tests were conducted years

  Lisa Kelley Cummings & Co

  00 N Hill Rd, Andover, VT 05143
• 

  

  /60

  $975,000 Sold Jan 24, 2025

  • 2,272 Sq Ft
  • $429/SF
  • 8 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2004

  1062 Andover Ridge Rd, Andover, VT 05143

  Welcome to 1062 Andover Ridge where you can buy a million-dollar view and get a gorgeous log home to go with it. The views are breathtaking and can be enjoyed from almost every room as well as the deck from either in or out of the 6-person hot tub. The recently renovated exterior and kitchen make this a perfect Vermont dream home. High-end stainless appliances, soapstone kitchen island, massive

  Kevin Barnes William Raveis Real Estate Vermont Properties

  1062 Andover Ridge Rd, Andover, VT 05143
• 

  

  /6

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,927 Sq Ft

  1002 Williams Dr, Middletown, PA 17057

  1002 Williams Dr, Middletown, PA 17057
• 

  

  /14

  $259,000

  • Land
  • 8.53 Acres
  • $30,363 per Acre

  224 Arrau Rd, Andover, VT 05143

  If you're searching for a slice of paradise, look no further than this Hidden Gem. Nestled in the heart of Vermont’s picturesque Green Mountains, this Andover lot offers everything you’ve been dreaming of. With the perfect blend of privacy and convenience, you’ll find peace and quiet paired with a short drive from the charming towns of Ludlow, Weston, Chester, and Londonderry. Spanning 8.53

  Thaddeus Abare Barrett and Valley Associates Inc.

  224 Arrau Rd, Andover, VT 05143
• 

  

  /13

  $125,000 Sold Dec 19, 2024

  • Land
  • 3.32 Acres
  • $37,651 per Acre

  • 254 Days On Market

  Lot 49 Andover Ridge Rd Unit 49, Andover, VT 05143

  Newly cleared mountaintop land in Andover Vermont! This lovely lot has both sunrise and sunset as well as gorgeous long range mountain vistas from all angles, not to be missed. Andover Ridge Road is a stunning community with beautiful homes angled to catch the terrific panoramic views. This property has a small natural pond at the roadside as well as a cleared site and still plenty of hardwood

  Erica Reynolds Southern Vermont Realty Group

  Lot 49 Andover Ridge Rd Unit 49, Andover, VT 05143
• 

  

  /39

  Est $637,340 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,359 Sq Ft

  424 Marsh Hill Rd, Andover, VT 05143

  424 Marsh Hill Rd, Andover, VT 05143
• 

  

  /18

  $299,000

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft

  26 Dorman Rd, Andover, VT 05143

  Prepare for an exhilarating mountain getaway at this enchanting four-bedroom chalet, nestled on a lush 2.1-acre estate in the heart of Andover. 2025 Ski season has been epic so far! Envision yourself minutes away from four renowned ski resorts, making this the perfect launchpad for your winter adventures. Immerse yourself in the local charm with easy access to the VAST trail network, offering a

  Daire Gibney Barrett and Valley Associates Inc.

  26 Dorman Rd, Andover, VT 05143
• 

  

  /31

  $465,000 Sold Nov 22, 2024

  • 2,311 Sq Ft
  • $201/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  345 Lovejoy Brook Rd, Ludlow, VT 05149

  Come discover this charming, well-maintained 3-bedroom, 2-bath home, nestled on a peaceful 4-acre lot in the heart of the Green Mountains in Andover, Vermont. Perfect for those seeking serenity, the property offers a blend of natural beauty and modern comfort. The home has seen several recent updates, including brand-new carpeting in the lower-level family room, where a cozy wood-burning stove

  Gary Coger Four Seasons Sotheby's Int'l Realty

  345 Lovejoy Brook Rd, Ludlow, VT 05149
• 

  

  /38

  Est $690,896 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,039 Sq Ft

  207 Spruce Dr, Andover, VT 05143

  207 Spruce Dr, Andover, VT 05143
• 

  

  /21

  $135,000

  • Land
  • 13.34 Acres
  • $10,120 per Acre

  00 Hill Top Rd, Andover, VT 05143

  If you're searching for the perfect lot to build your dream home, this 13+ acre property could be just what you've been looking for! Nestled on a peaceful road, this expansive lot offers a prime opportunity to create your ideal home while staying close to top local attractions, including the stunning mountains of Okemo, Stratton, Magic, and Bromley. With permits already in place for a

  Flex Realty Group Flex Realty

  00 Hill Top Rd, Andover, VT 05143
• 

  

  /30

  $685,000 Sold Nov 22, 2024

  • 1,504 Sq Ft
  • $455/SF
  • 88 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1976

  3011 A East Hill Rd, Andover, VT 05143

  Price Adjustment! This gracious country contemporary, on the market for the first time, was designed and finished by its longtime owners, an industrial designer and an interior designer. Beautifully sited in a landscaped setting on a quiet country road, it enjoys distant mountain views and is protected on all sides by woods with nature trails. The 3 bed/3 bath interior is light and airy with

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3011 A East Hill Rd, Andover, VT 05143
• 

  

  /29

  Est $592,001 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  4088 Weston-Andover Rd, Andover, VT 05143

  4088 Weston-Andover Rd, 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

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