43

Homes for Sale near Chester-Andover Elementary School

Section Image
  • 688 Hidden Heights Rd, Chester, VT 05143
    688 Hidden Heights Rd, Chester, VT 05143
    688 Hidden Heights Rd, Chester, VT 05143
    /59

    $685,000

    • 3 Beds
    • 2 Baths
    • 2,205 Sq Ft

    688 Hidden Heights Rd, Chester, VT 05143

    Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of

    Joseph Karl William Raveis Real Estate Vermont Properties

    688 Hidden Heights Rd, Chester, VT 05143
  • 95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    /52

    $667,500

    • 4 Beds
    • 3 Baths
    • 2,794 Sq Ft

    95 Church St, Chester, VT 05143

    Charming Renovated Farmhouse in the Heart of ChesterThis beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway.Inside, enjoy a spacious kitchen with custom

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    95 Church St, Chester, VT 05143
  • 2904 E Hill Rd, Andover, VT 05143
    2904 E Hill Rd, Andover, VT 05143
    2904 E Hill Rd, Andover, VT 05143
    /40

    $950,000

    • 4 Beds
    • 4 Baths
    • 3,278 Sq Ft

    2904 E Hill Rd, Andover, VT 05143

    Perched on 60 acres with views of Okemo Mountain from its second floor, this custom designed contemporary is hitting the market for the first time. Built by an international journalist and his writer wife as a retreat for their family and high profile friends, it now awaits its next lucky stewards. Filled with natural light, the rambling home was inspired by a friend's classic Vermont

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    2904 E Hill Rd, Andover, VT 05143
  • 725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    /58

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 2,544 Sq Ft

    725 Flamstead Rd, Chester, VT 05143

    Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    725 Flamstead Rd, Chester, VT 05143
  • 1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, Chester, VT 05143
    /49

    $1,100,000

    • 4 Beds
    • 4 Baths
    • 3,920 Sq Ft

    1847 Trebo Rd, Chester, VT 05143

    With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1847 Trebo Rd, Chester, VT 05143
  • 525 Route 103 N, Chester, VT 05143
    525 Route 103 N, Chester, VT 05143
    525 Route 103 N, Chester, VT 05143
    /60

    $495,000

    • 6 Beds
    • 1 Bath
    • 2,308 Sq Ft

    525 Route 103 N, Chester, VT 05143

    The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

    Glenn Olney Barrett and Valley Associates Inc.

    525 Route 103 N, Chester, VT 05143
  • 1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    /56

    $599,999

    • 5 Beds
    • 3.5 Baths
    • 2,443 Sq Ft

    1057 Quarry Rd, Chester, VT 05143

    Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    1057 Quarry Rd, Chester, VT 05143
  • 2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    /52

    $627,500

    • 3 Beds
    • 2.5 Baths
    • 1,868 Sq Ft

    2510 E Hill Rd, Chester, VT 05143

    This home on East Hill Road commands one of the area's best views all the way to Stratton! It is one of those spots where the view is different every day & spectacular! The home sits on 14 acres & it overlooks land protected by the Vermont Land Trust and mountains beyond. From the moment you enter, you won't want to leave. It is immaculate and ready to go. A large mudroom with a slate floor &

    Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
  • 231 Richardson Rd, Chester, VT 05143
    231 Richardson Rd, Chester, VT 05143
    231 Richardson Rd, Chester, VT 05143
    /35

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 1,304 Sq Ft

    231 Richardson Rd, Chester, VT 05143

    This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also

    Thaddeus Abare Barrett and Valley Associates Inc.

    231 Richardson Rd, Chester, VT 05143
  • 1809 Marsh Hill Rd, Andover, VT 05143
    1809 Marsh Hill Rd, Andover, VT 05143
    1809 Marsh Hill Rd, Andover, VT 05143
    /28

    $485,000

    • Land
    • 57 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
  • 663 Depot St, Chester, VT 05143
    663 Depot St, Chester, VT 05143
    663 Depot St, Chester, VT 05143
    /44

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    663 Depot St, Chester, VT 05143

    Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

    Betsy Adamovich Real Broker LLC

    663 Depot St, 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
    • 7 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
  • 00 Vt Route 103 N, Chester, VT 05143
    00 Vt Route 103 N, Chester, VT 05143
    00 Vt Route 103 N, Chester, VT 05143
    /60

    $115,000

    • Land
    • 3.28 Acres
    • $35,061 per Acre

    00 Vt Route 103 N, Chester, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed 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 offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing.

    Rachael Rogala Rachael Rogala Inc.

    00 Vt Route 103 N, Chester, VT 05143
  • 413 Hidden Heights Rd, Chester, VT 05143
    413 Hidden Heights Rd, Chester, VT 05143
    413 Hidden Heights Rd, Chester, VT 05143
    /34

    $210,000

    • 1 Bed
    • 1 Bath
    • 617 Sq Ft

    413 Hidden Heights Rd, Chester, VT 05143

    Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

    Glenn Olney Barrett and Valley Associates Inc.

    413 Hidden Heights Rd, Chester, VT 05143
  • 442 Vermont 103, Chester, VT 05143
    442 Vermont 103, Chester, VT 05143
    442 Vermont 103, Chester, VT 05143
    /60

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    442 Vermont 103, Chester, VT 05143

    Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

    Rachael Rogala Rachael Rogala Inc.

    442 Vermont 103, Chester, VT 05143
  • 302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill Rd, Chester, VT 05143
    /19

    $379,900

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    302 Davidson Hill Rd, Chester, VT 05143

    This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

    Thaddeus Abare Barrett and Valley Associates Inc.

    302 Davidson Hill Rd, Chester, VT 05143
  • 1749 Middletown Rd, Andover, VT 05143
    1749 Middletown Rd, Andover, VT 05143
    1749 Middletown Rd, Andover, 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
  • 00 Hillcrest Dr, Andover, VT 05143
    00 Hillcrest Dr, Andover, VT 05143
    00 Hillcrest Dr, Andover, VT 05143
    /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
  • 0 Remington Rd Unit 5049900, Chester, VT 05143
    0 Remington Rd Unit 5049900, Chester, VT 05143
    0 Remington Rd Unit 5049900, Chester, VT 05143
    /21

    $55,000

    • Land
    • 1.52 Acres
    • $36,184 per Acre

    0 Remington Rd Unit 5049900, Chester, VT 05143

    If you're dreaming of open skies, peaceful surroundings, and your own slice of Vermont, this property delivers. Just minutes from the charming Chester village green, this land offers the best of both worlds—seclusion and convenience. Step onto the property and take in the wide-open space surrounded by mature trees, offering privacy and natural beauty in every season. Whether you're envisioning

    Frank Provance Diamond Realty

    0 Remington Rd Unit 5049900, Chester, VT 05143
  • 0 Remington Rd Unit 5049898, Chester, VT 05143
    0 Remington Rd Unit 5049898, Chester, VT 05143
    0 Remington Rd Unit 5049898, Chester, VT 05143
    /20

    $85,000

    • Land
    • 1.82 Acres
    • $46,703 per Acre

    0 Remington Rd Unit 5049898, Chester, VT 05143

    Bring your plans and build your own piece of paradise! Just minutes from the iconic Chester town green, this scenic parcel offers the perfect blend of privacy, mountain views, and convenience. With a cleared, gently sloping build site already in place, this lot is ready for your imagination. Underground power is on site, and a well-crafted stone retaining wall, drilled well and septic components

    Frank Provance Diamond Realty

    0 Remington Rd Unit 5049898, Chester, VT 05143
  • 611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    /32

    $2,250,000

    • 2 Beds
    • 4 Baths
    • 2,410 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
  • 157 Thompson Rd, Chester, VT 05143
    157 Thompson Rd, Chester, VT 05143
    157 Thompson Rd, Chester, VT 05143
    /56

    $1,249,000

    • 4 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    157 Thompson Rd, Chester, VT 05143

    Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

    Joe Castaluccio Winhall Real Estate

    157 Thompson Rd, Chester, VT 05143
  • 419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    /12

    $239,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    419 Coach Rd, Chester, VT 05143

    Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

    Amy Carson Lowe's Real Estate, LLC

    419 Coach Rd, Chester, VT 05143
  • 00 Simonsville Rd, Andover, VT 05143
    00 Simonsville Rd, Andover, VT 05143
    00 Simonsville Rd, Andover, 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
  • 160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    /26

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,327 Sq Ft

    160 Depot St, Chester, VT 05143

    Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

    Joshua Lemieux Remax Summit

    160 Depot St, Chester, VT 05143
  • 81 Trombley Rd, Andover, VT 05143
    81 Trombley Rd, Andover, VT 05143
    81 Trombley Rd, Andover, 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
  • Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson Rd, Chester, VT 05143
    /15

    $129,000

    • Land
    • 3.24 Acres
    • $39,815 per Acre

    Lot 3 Mattson Rd, Chester, VT 05143

    Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion.As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out

    Jessica Citera Cummings & Co

    Lot 3 Mattson Rd, Chester, VT 05143
  • 3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    /30

    $650,000

    • 3 Beds
    • 3 Baths
    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, Chester, VT 05143
  • 491 Farrar Rd, Chester, VT 05143
    491 Farrar Rd, Chester, VT 05143
    491 Farrar Rd, Chester, VT 05143
    /29

    $399,000

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft

    491 Farrar Rd, Chester, VT 05143

    Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

    Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
  • 00 E Hill Rd, Andover, VT 05143
    00 E Hill Rd, Andover, VT 05143
    00 E Hill Rd, Andover, VT 05143
    /11

    $119,000

    • Land
    • 16 Acres
    • $7,589 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
  • 00 N Hill Rd, Andover, VT 05143
    00 N Hill Rd, Andover, VT 05143
    00 N Hill Rd, Andover, VT 05143
    /5

    $80,000

    • Land
    • 4.30 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
  • 847 Simonsville Rd, Andover, VT 05143
    847 Simonsville Rd, Andover, VT 05143
    847 Simonsville Rd, Andover, VT 05143
    /34

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    847 Simonsville Rd, Andover, VT 05143

    Come find your own peaceful piece of the Vermont countryside in the beautiful town of Andover. Look no further than this move in ready homestead on 51.2 rolling acres with two large paddocks fenced and ready waiting for your animals, complete with two spacious sheds, and a chicken coop ready to house them. Established asparagus patch, blueberry bushes, apple trees, and even your own cranberry bog

    Erin Kendall EXP Realty

    847 Simonsville Rd, Andover, VT 05143
  • 224 Arrau Rd, Andover, VT 05143
    224 Arrau Rd, Andover, VT 05143
    224 Arrau Rd, Andover, VT 05143
    /14

    $259,000

    • Land
    • 9 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
  • 58 Remington Rd, Chester, VT 05143
    58 Remington Rd, Chester, VT 05143
    58 Remington Rd, Chester, VT 05143
    /23

    $69,000

    • Land
    • 2.86 Acres
    • $24,126 per Acre

    58 Remington Rd, Chester, VT 05143

    Building lot with driveway and culverts in place, lot has preliminary site work complete including level grass land area, electrical transformer and 100 amp electrical power plus VTel fiber internet on lot for your new Vermont home. Home must be a minimun of 1,800 square feet of finished living space. Wastewater design and permits in place. A 16' x 25' garage/shed on lot for storage while

    John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
  • 423 Main St, Chester, VT 05143
    423 Main St, Chester, VT 05143
    423 Main St, Chester, VT 05143
    /36

    $575,000

    • 6 Beds
    • 5 Baths
    • 3,217 Sq Ft

    423 Main St, Chester, VT 05143

    Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing

    Betty McEnaney Diamond Realty

    423 Main St, Chester, VT 05143
  • 26 Dorman Rd, Andover, VT 05143
    26 Dorman Rd, Andover, VT 05143
    26 Dorman Rd, Andover, VT 05143
    /18

    $325,000

    • 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
  • 00 Hill Top Rd, Andover, VT 05143
    00 Hill Top Rd, Andover, VT 05143
    00 Hill Top Rd, Andover, VT 05143
    /10

    $135,000

    • Land
    • 13 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
  • 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

    $6,950,000

    • 8 Beds
    • 7.5 Baths
    • 8,262 Sq Ft

    3800 Weston-Andover Rd, Andover, VT 05143

    Escape to Moosewalk Lane, a fully furnished and equipped luxury estate in Andover, Vermont, set on 384 acres in the iconic Green Mountains. This one of a kind property offers a rare blend of seclusion, natural beauty, 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 construction, the

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • 1377 Vermont 103, Chester, VT 05143
    1377 Vermont 103, Chester, VT 05143
    1377 Vermont 103, Chester, VT 05143
    /40

    $495,000

    • 2,280 Sq Ft

    1377 Vermont 103, Chester, VT 05143

    Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business. There are 2 separate buildings. One needs to be finished, main building 3 floor could be finished for more living space.

    Mike England Michael England Real Estate

    1377 Vermont 103, Chester, VT 05143

Showing Results 1 - 40, Page 1 of 2

Vermont Windsor County Chester Chester-Andover Elementary School

Real Estate & Homes for Sale near Chester-Andover Elementary School

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group