Andover/Chester

The Town of Andover lies just east of Weston and the story goes that Weston was once actually a part of Andover ( the "west town") and what is now Andover and Weston were separated by the bad roads and steep hills of Terrible Mountain. Terrible Mountain is now home to Andover Ridge Road and the mountain's ridge line spans the territory between Andover, Weston and Ludlow. Andover sits almost equidistant between the towns of Chester, Ludlow and Londonderry and residents and visitors can easily enjoy, explore and utilize services in any of those towns.

 

Chester is one of Vermont's quintessential small towns with a beautiful Town Green in the center of town, surrounded by small shops, galleries and a few restaurants. From it's website: " Chester is a quaint New England town with a population of 3,144, centrally located, and in close proximity to several ski areas including Okemo, Stratton, and Killington. Chester offers a community of great restaurants, comfortable B & Bs, and interesting shops, including authentic antique stores and lovely art galleries. Whether you are looking for a quiet respite, or just adventuring off the beaten path..... Here, you can enjoy a tranquil and charming atmosphere. Chester is also a wonderful place to live!"

 

Outdoor activities in the area range from skiing at Okemo Mountain or Magic Mountain in nearby Londonderry, or spending time on the lakes north of Ludlow. Andover residents will attend Chester-Andover Elementary and Green Mountain Union High School.

 

Properties are listed by price in order from high to low. You may change your sort order below, and you can refine your search by checking or unchecking the search criteria (or sliding the criteria bar) along the right side of this page.

326 Goodrich Road Chester VT 05143

MLS Number 4963698

  • Commercial
  • Address 326 Goodrich Road
  • Year Built 2019
  • Square Feet 1,760
  • Acreage 25.99

This is a first class stone quarry operation which pumps out a beautiful stream of high grade gneiss stone, so indispensable for the building trades in constructing patios, steps, walls, chimneys, and every place beautifully ad naturally colored building stones are needed. The next owner of this business will of course be buying a highly profitable and proven going concern. However, the next owner will have seen the monumental opportunity in the $168,000,000, in unmined, and yet very minable stone as attested to by the attached professionally prepared geological report. Complete with $1.5 M worth of meticulously maintained equipment and an immaculate stone cutting shop, this offering spells opportunity writ large. While the Owner believes the next owner will be someone already in the industry, and he may be correct, I also believe that it could be anyone who sees the brilliance of buying assets for pennies on the currently shrinking and inflated dollar along with a proven and successful method for extracting same. But what do I know? I'm just a Realtor. But an entrepreurial MBA Realtor nonetheless who will be happy to show you this opportunity in person.

Listed by Lawrence Zupan of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3800 Weston Andover Road Andover VT 05143

Andover, VT3800 Weston Andover Road

Price$8,300,000

Est. Mortgage: $/month

MLS Number 5015743

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 8
  • Bathroom 8

A magnificent 10,062 SF family compound. Custom built, it comes fully furnished and equipped for immediate occupancy, featuring 7BR, 8BA, a separate 1BR guesthouse and office, a furnished and heated writers cabin overlooking the Connecticut River Valley, and an equipment barn, all situated on 384 acres of pristine hardwood forest, accessed by an 1800' paved driveway. Anchored by miles of woodland trails and located in Andover, Vermont, the offering includes outdoor sculpture and artwork, historic rock walls, open fields and building ruins from early settlers, along with direct access to the VAST trail system for winter trail riding. The main house features a soaring 2-story fireplace, post and beam timber frame construction, and a chef's kitchen with double appliances, Viking 60” cooktop and wood-fired interior pizza oven, while a reading loft and library add a calming vibe to the outdoor view. The primary suite has a 2BR, 2BA configuration on the main floor with 5 additional bedrooms with en suite baths. There are 6 garage bays supplied with commercial sinks, a 21' x 35' open design gym and exercise suite, and a media room with custom pool table and walkout to the ground floor. Designed for 4-season recreation, privacy and small batch maple syrup production, the hardwood forest, mountain trails, open fields, and additional access from another town road offer unlimited possibilities for the discerning buyer looking for a lifestyle in Vermont's iconic Green Mountains.

Listed by Steve Stettler and Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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40 The Common Chester VT 05143

MLS Number 5008052

  • Commercial
  • Address 40 The Common
  • Year Built 1920
  • Square Feet 18,896
  • Acreage 2.28

Introducing the cultural and commercial centerpiece of one of Vermont's classic small towns: The Fullerton Inn of Chester! In addition to being the anchor go-to Bar & 120-seat Restaurant for locals & tourists (be it indoor or outdoor dining), the venerable, well established Inn boasts 20 guest suites & rooms. Heated outdoor tables on back patio extend the season & Village camaraderie as does the classic front Porch overlooking the Town Green and Gazebo. More Meeting & Event rooms along w/ versatile room/suite configurations open the event venue market for weddings & more amid year-round attractions within ski country, fall foliage, etc... As a nicely profitable going concern, the Fullerton Inn beckons its next owner to seize the reins & fulfill their dreams of operating a country Inn, or adding it to their hospitality portfolio. Professionally managed & maintained, the Inn offers seamless transfer w/ transition assistance, dedicated Executive Chef & staff. Additional features & equipment: large fully equipped 20' x 40' professional kitchen w/ walk-in cooler-kitchen freezer-large utility space-convection oven and fryer-2 double coolers-ice machine-fully sprinklered whole building-2 owner apartments (1 is 1200')-5YO Peerless furnace w/ backup furnace in full basement w/ separate heating & cooling for bar-basement chillers-bank vault-workshop-laundry room-paint room-delivery access. Stroll to the Inn's flower gardens, 2 outbuildings & river flowing behind 2.4 flat usable acres.

Listed by Zachary Zupan and Lawrence Zupan of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1502 Popple Dungeon Road Chester VT 05143

Chester, VT1502 Popple Dungeon Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 5034215

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4

Welcome to paradise! Enjoy all four seasons in this handsome colonial-style home with modern amenities. From the covered porch, relax and take in views of the front gardens and your land across the road with apple trees and brook frontage. A large solar array is tucked out of sight producing all the power you would need. Behind the house is a fenced-in garden and greenhouse, a couple of useful sheds and a large, fenced pasture bordered by a brook. Off to the side are two livestock barns and a new 24' x 48' equipment shed. If you have use for a large studio space, you are in luck. Above the 2-car garage is a suite outfitted with a kitchen, ¾ bath, and a large open room with fiber internet, perfect for working, writing, creating art, or exercising. Saving the best for last, the home is just lovely. The dream country kitchen with high end appliances and custom tile is open to the sitting room with fireplace. The dining room enjoys the wall of windows overlooking the back acreage. There is a den with closets and ¾ bath, and second living room with French doors to the porch. There is a large, functional mudroom for all your gear. Upstairs is the primary suite with steam shower and two very generous bedrooms and another renovated bath. Located 3.5 from the town green on a paved road, and close to 3 ski resorts, this unique property provides a wonderful place for living, working, or vacationing. View the video tour and look at the attachments for all the recent improvements.

Listed by Betty McEnaney of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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31 Palmer Road Chester VT 05143

Chester, VT31 Palmer Road

Price$750,000

Est. Mortgage: $/month

MLS Number 5029353

  • Residential Single Family
  • Full Bath 2
  • Address 31 Palmer Road
  • Construction Existing
  • Bedrooms 3

Rivers Edge Farm is an absolutely diverse agricultural property which serves bovine, equine and many other farm animals currently and in its past history. 22+ organic acres of rich river bottom land yields a robust crop of haylage, corn or hay or whatever suits your needs. The buildings are mixed use for the owners. Some are animal occupied and feed storage and one is a large garage/workshop that any mechanic would covet. The home is as warm and welcoming as you can get with an updated kitchen, wood floors and a foyer with individual cubbies for occupants to claim as their own. 3 large bedrooms on the second floor and an option for a first floor bedroom vs a playroom exists. Keep the weather and earth outdoors with your covered porches surrounding most sides of the home. Enjoy the river with a seasonal swimming hole under the railroad bridge and there's even a tiny house for those city folk who want a taste of country life. The current owners also sell meats and eggs. Lots of income generation can be gained at Rivers Edge Farm. Come see the potential for yourself!

Listed by Leila Tarantelli of KW Coastal and Lakes & Mountains Realty/Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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31 Palmer Road Chester VT 05143

MLS Number 5031821

  • Commercial
  • Address 31 Palmer Road
  • Year Built 1980
  • Square Feet 3,249
  • Acreage 22.8

Rivers Edge Farm is an absolutely diverse agricultural property which serves bovine, equine and many other farm animals currently and in its past history. 22+ organic acres of rich river bottom land yields a robust crop of haylage, corn or hay or whatever suits your needs. The buildings are mixed use for the owners. Some are animal occupied and feed storage and one is a large garage/workshop that any mechanic would covet. The home is as warm and welcoming as you can get with an updated kitchen, wood floors and a foyer with individual cubbies for occupants to claim as their own. 3 large bedrooms on the second floor and an option for a first floor bedroom vs a playroom exists. Keep the weather and earth outdoors with your covered porches surrounding most sides of the home. Enjoy the river with a seasonal swimming hole under the railroad bridge and there's even a tiny house for those city folk who want a taste of country life. The current owners also sell meats and eggs. Lots of income generation can be gained at Rivers Edge Farm. Come see the potential for yourself!

Listed by Leila Tarantelli of KW Coastal and Lakes & Mountains Realty/Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23 School Street Chester VT 05143

MLS Number 5023262

  • Commercial
  • Address 23 School Street
  • Year Built 1880
  • Square Feet 6,894
  • Acreage 0.5

Unlock the potential of this exceptional mixed-use property, offering a solid income stream and tremendous future upside. Ideally situated in the heart of town, this well-maintained building spans over 6,800 sq. ft. and is currently home to 5 residential units and 6 office units, with potential for retail conversion. Located in the center of town, providing excellent visibility and foot traffic, with easy access to amenities, and major roadways. The property currently generates solid monthly rental income from the residential and office units, with significant potential for increased rents after updates and improvements. The 5 residential units are in good condition but could benefit from updates, offering an opportunity to increase rental rates and enhance value through renovations. The 6 office units offer flexibility for a variety of businesses, with the added benefit of retail potential on the ground floor. Spanning over 6,800 sq. ft., this property offers ample space for both residential and commercial tenants, with room for potential expansion or redevelopment.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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43 Lee Way Andover VT 05143

Andover, VT43 Lee Way

Price$629,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4973994

  • Residential Single Family
  • Full Bath 3
  • Address 43 Lee Way
  • Construction Existing
  • Bedrooms 3

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 driveway, newly stained decks and covered porch, and new exterior drainage. The house is situated to maximize your southern exposure and the three bedroom/3 bath floor plan is open, spacious and includes an en-suite primary. The large finished bonus room is just that - a BONUS and maximizes the lifestyle options whether you are a weekend warrior and second home owner or plan to make this a full time residence! A full unfinished basement offers the opportunity for finishing. Updated systems include the Buderus furnace and fiber optic VTel provides high speed internet. The double attached heated garage opens to a mudroom.It is not often, that a property is move-in ready. The winter ski season is around the corner and you can be settled in with a cozy and welcoming residence. Showing appointments begin on Saturday.

Listed by Britt Wohler and Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Depot Street Chester VT 05143

MLS Number 5005895

  • Commercial
  • Address 15 Depot Street
  • Year Built 1880
  • Square Feet 4,493
  • Area VT-Windsor

Come and invest in Main Street America with this exceptional village center location! Are you seeking a state-of-the-art building with excellent revenue opportunities? Look no further. This property has been meticulously updated from top to bottom, offering a prime investment opportunity. The first floor features an expansive open space, formerly an art and presentation gallery, equipped with a portable stage, media room, fully equipped kitchen, LED lighting, skylights, decorative walls, and black walnut flooring. The second floor includes two fully renovated apartments: a one-bedroom and a two-bedroom, both generating approximately $2,800/month . The lower level is climate-controlled with artist stalls, providing additional storage options. Outside, you'll find a handicap ramp for accessibility and and ADA bathrooms; additionally, a large 1850 barn currently used for storage, adds unique character and potential for further utilization. This one-of-a-kind property is a must-see for investors looking to capitalize on a versatile and modern space with substantial income potential.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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559 Davidson Hill Road Chester VT 05143

Chester, VT559 Davidson Hill Road

Price$589,000

Est. Mortgage: $/month

MLS Number 4996384

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Luxurious contemporary home in a naturalized setting. Beautiful mountain views from family room and expansive deck. This home is a unique blend of country charm and modern convenience. Everyone will gather round the large center island in this amazing kitchen designed for cooking and entertaining. Open concept floor plan flows from kitchen to dining area and into the family room where you can set and take in the mountain views beyond. Slider leads to the deck combining indoor and outdoor living space. A private den is connected to the family room with French doors and can be opened up for addition living space or closed off for a quiet retreat. Second floor has three generous sized bedrooms, two of which are en suites. There is also a bonus room on the second floor that can be used for crafts, or additional den, home office or playroom. Wired for generator as well. Currently used as a family getaway and Airbnb. Home is located within minutes from year-round outdoor fun. Chester Recreation Center has a beautiful pool and lots of play area too. There are also local swimming holes, lots of hiking trails with lots to do. Just 18 minutes to the ski lifts at Okemo.

Listed by Julie Buffum of Buffum Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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643 Route 103 South Chester VT 05143

MLS Number 5002938

  • Commercial
  • Address 643 Route 103 South
  • Year Built 1979
  • Square Feet 2,504
  • Acreage 1.75

OPPORTUNITY KNOCKS! This full-scale restaurant is a deli and bakery with catering business with 20 years cliental of loyal patronage. This is a turn-key operation that comes fully equipped and has a beer & wine license for the restaurant and an outside under the tent. Sales includes real estate with 1.8 acres with frontage on Rte. 103 which is the second busiest tourist route in Vermont,

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4877 Vt Route 103 Chester VT 05143

Chester, VT4877 Vt Route 103

Price$500,000

Est. Mortgage: $/month

MLS Number 4986618

  • Residential Single Family
  • Full Bath 2
  • Address 4877 Vt Route 103
  • Construction Existing
  • Bedrooms 4

Looking for the perfect ready to move in home in Vermont? Look no further than this French Provincial meets Vermont cabin centrally located in the quiet town of Chester, Vermont on Route 103. Within an hour drive to 5+ great ski mountains, within 10 minutes to Okemo mountain. House features so many great amenities and improvements--new black/grey roof just installed June 2024, new egress windows, beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes and state parks, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today!

Listed by Erin Kendall of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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663 Depot Street Chester VT 05143

Chester, VT663 Depot Street

Price$489,000

Est. Mortgage: $/month

MLS Number 5038088

  • Residential Single Family
  • Address 663 Depot Street
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Experience the warmth of history with the ease of modern living at 663 Depot Street. This fully renovated 3-bedroom, 2-bath home offers historic charm with today's updates. Since 2022, insulation, drywall, electrical, plumbing, HVAC, furnace, water heater, fixtures, countertops, cabinets, and appliances have all been replaced. The home's original wood flooring has been carefully refinished to honor its roots. Period-appropriate paint colors and thoughtful details like exposed beams and original woodwork add to the timeless feel. The attached 2-story post-and-beam barn-larger than the house-offers incredible potential to expand your living space or create a dream workshop. Set on 1 acre with a sprawling lawn, fire pit, and a prime location near Chester's Stone Village, Grist Mill, Smitty's Market, and more. Just 15 min to Okemo and the lakes, 30 min to Bromley, and under an hour to Killington, Stratton, and Mount Snow, it's ideal for year-round fun. Currently enjoyed as both a family getaway and a successful Airbnb, it offers strong income potential. Whether you're looking for a primary home or investment, this timeless property is not to be missed.

Listed by Betsy Adamovich of Real Broker LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Spectacular Andover Property with Views, Pond, Power to Site & More

1809 Marsh Hill Road Andover VT 05143

Andover, VT1809 Marsh Hill Road

Price$485,000

Est. Mortgage: $/month

MLS Number 4959138

  • Land
  • Address 1809 Marsh Hill Road
  • Acreage 57.2
  • Area VT-Windsor
  • PricePerSqFt 8479.02

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 seclusion and complete quiet (other than the birds composing Mother Nature's own music). A long, private driveway is already in place and subtly drops you from Marsh Hill Road through the upper wooded section to a beautiful, cleared building site. Electricity is installed and buried the length of the driveway to the building site and approximately 5 acres are cleared and just waiting to be built on. A VT wastewater permit for a total of 6 bedrooms will permit you to build to suit your needs: one spacious home, or perhaps a main house (4-5 BR) and guest house (1-2BR). Spend your summers lazing in the pond, hiking around your hillside, attending Broadway-caliber live theater and music at the nearby Weston Theater Company, picking out the freshest ingredients for your meals at the Londonderry Farmer's Market, and exploring the Green Mountains. In the winter, you can hunker down and enjoy your Vermont home and, for the more active among you, there are four major ski resorts within a 10-35 minutes-drive, Nordic skiing nearby and lots of cozy restaurants to try. Come take a look!

Listed by Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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00 Valley View Drive Andover VT 05143

Andover, VT00 Valley View Drive

Price$485,000

Est. Mortgage: $/month

MLS Number 5027492

  • Land
  • Address 00 Valley View Drive
  • Acreage 26.99
  • Area VT-Windsor
  • PricePerSqFt 17969.62

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 guest house. Come build your dream home in the quiet upscale community of Summit Ridge.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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96 S. Main Street Chester VT 05161

Chester, VT96 S. Main Street

Price$469,000

Est. Mortgage: $/month

MLS Number 5024631

  • Residential Single Family
  • Full Bath 1
  • Address 96 S. Main Street
  • Construction Existing
  • Bedrooms 4

This spacious 1800's home is filled with Vermont charm and located in the heart of Chester. Filled with natural light from newly installed windows, the home boasts beautiful wood floors throughout and antique door handles that capture the essence of the era. Spacious bedrooms provide ample comfort, while smart thermostats ensure modern convenience. A newly built, covered front porch welcomes you into the home, and a deck off the kitchen leads to an open, level backyard-perfect for gardening or outdoor activities. One of the standout features of this property is the versatile studio space. Accessible via its own entrance from Main Street, this expansive area features vaulted ceilings and two half baths, offering endless possibilities. Whether you're looking to create a storefront, set up an at-home business, or convert the space into a private apartment, the potential is limitless. This property offers a unique opportunity to live in a quintessential Vermont town while having the flexibility to tailor the space to your needs. It's a must-see for anyone seeking a charming, functional home with potential for growth!

Listed by Jessica Citera of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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332 Hidden Heights Road Chester VT 05143

Chester, VT332 Hidden Heights Road

Price$450,000

Est. Mortgage: $/month

MLS Number 5037126

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3

This charming multi-level home provides 4 bedrooms and a variety of places to find private space for quiet. Also a large open recreation room which includes a full size pool table/table tennis table and dry bar. Located just 3 miles from the charming Town of Chester. An easy drive to Bromley Mt, Magic Mt and Okemo, this makes a great home for an active family. Beautiful views from the deck provide a great place for morning coffee and an evening watching the stars. There is plenty of space for gardens and outdoor activities as well as wooded land to spend relaxing time in. House has automatic whole house propane generator. There are two firemen that live on the road, so it is always well plowed and maintained.

Listed by John Tolosky of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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134 Gold River Extension Chester VT 05143

MLS Number 4952929

  • Commercial
  • Square Feet 6,656
  • Acreage 2.49
  • Area VT-Windsor
  • PricePerSqFt 63.85

Rare opportunity with commercial/industrial zoning. 2.49 acres that is fully permitted. Property can be used as one business spot, or share the office building with another business. Currently there are 3 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, office, and rail siding; plus an additional 1500 sq ft storage building. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Video attached to the MLS.

Listed by Paul William Carroccio and Marek Kovac of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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196 North Street Chester VT 05143

Chester, VT196 North Street

Price$425,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5023780

  • Residential Single Family
  • Full Bath 3
  • Address 196 North Street
  • Construction Existing
  • Bedrooms 3

The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26 Dorman Road Andover VT 05143

Andover, VT26 Dorman Road

Price$359,000

Est. Mortgage: $/month

MLS Number 5029533

  • Residential Single Family
  • Address 26 Dorman Road
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

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 plethora of entry points nearby. This alpine retreat has been a cherished sanctuary for over 40 years, lovingly maintained by its owners and their dedicated local caretakers. Offering a seamless blend of comfort and convenience, this home is sold fully furnished, ready for you to step in and relish its homely charm "as is." The layout features two cozy bedrooms on each floor, ensuring ample space for family and guests alike. Step inside to discover a welcoming front porch at the entry level, and ascend to the top floor to unwind on the deck with south-eastern views. The heart of the chalet hosts the kitchen and dining areas on the first floor, while the main living and family rooms upstairs provide a spacious haven for relaxation and entertainment. Enhanced by high-speed fiber optics internet from VTel, stay connected and productive in your serene mountain escape. Positioned ideally for those passionate about skiing and outdoor activities, choose from Magic, Stratton, Okemo, and Bromley ski areas, or indulge in hiking, fishing, biking, golfing, and swimming in the vibrant surroundings.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1749 Middletown Road Andover VT 05143

Andover, VT1749 Middletown Road

Price$359,000

Est. Mortgage: $/month

MLS Number 4995283

  • Land
  • Address 1749 Middletown Road
  • Acreage 31
  • Area VT-Windsor
  • Utilities Gas - LP/Bottle

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 mostly wooded acreage. The long driveway approach gives you a true sense of a cabin in the woods retreat. The addition of a septic system and well, could make this potentially a year round home. Fantastic location on Middletown Rd. Just minutes to center of Weston where you'll find the Vermont Country Store, excellent dining and the historic Weston Playhouse. Near several major ski resorts, Okemo, Magic, Stratton and Bromley Mountain. This is truly a find that offers the best of the Vermont experience. 3 Bedroom WW permit is available.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1749 Middletown Road Andover VT 05143

Andover, VT1749 Middletown Road

Price$359,000

Est. Mortgage: $/month

MLS Number 4995277

  • Residential Single Family
  • Address 1749 Middletown Road
  • Construction Existing
  • Bedrooms 3
  • Square Feet 1,504

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 mostly wooded acreage. The long driveway approach gives you a true sense of a cabin in the woods retreat. A recently done septic Design and Wastewater permit make this a year round home possibility. Fantastic location on Middletown Rd. Just minutes to center of Weston where you'll find the Vermont Country Store, excellent dining and the historic Weston Playhouse. Near several major ski resorts, Okemo, Magic, Stratton and Bromley Mountain. This is truly a find that offers the best of the Vermont experience. State approved WW permit available

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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198 Coach Road Chester VT 05143

Chester, VT198 Coach Road

Price$329,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5034709

  • Residential Single Family
  • Full Bath 1
  • Address 198 Coach Road
  • Construction Existing
  • Bedrooms 4

Imagine a home so inviting and comfortable, you'd never want to leave. Welcome to this practical and low-maintenance ranch-style home, perfectly designed for both relaxation and entertainment. Step inside and be greeted by the beautifully updated living room, bathed in natural light and warmed by a cozy wood stove-a haven during those chilly Vermont winters.This house isn't just a place to live; it's a space to thrive. The open concept kitchen and dining area, complete with a breakfast bar and ample cabinet space, serves as the heart of the home. Whether you're whipping up a family meal or hosting a casual brunch, this kitchen handles it all with ease.The practicality continues with three comfortable bedrooms on the main level alongside a full bathroom and primary ensuite. Venture downstairs to the fully finished basement, a dynamic space featuring an additional bedroom, a 1/2 bathroom, a media room, and a sizable office space currently set up as a gym. There is so much space you imagination can run wild with ideas for new uses.Maintenance is a breeze both inside and out, letting you spend more time enjoying your home and less on upkeep. The yard is just as manageable, ideal for those who appreciate outdoor space without the hassle.This clean, streamlined home is ready for you to make it your own. Don't miss out on this charming, expansive ranch-call today to schedule your viewing and start imagining your life here, where every day feels like a retreat.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3590 Vt 103 North Chester VT 05143

Chester, VT3590 Vt 103 North

Price$319,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4994539

  • Residential Single Family
  • Full Bath 2
  • Address 3590 Vt 103 North
  • Construction Existing
  • Bedrooms 4

Fully furnished! Thoughtfully upgraded home on .89 acres located in the beautiful area of Gassetts in Chester, Vermont. Easy access to I-91, 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. This three bedroom, two bathroom home has an open concept. Two bedrooms on the second floor and one bedroom on the third floor. One bedroom on the second floor is a primary bedroom with a full bathroom. Large open area kitchen and dining room with plenty of room for storage, cooking and entertaining. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quartz countertops, new sheetrock and paint throughout, new sub flooring in the living room, laundry area, and mudroom, new window sills, new mini split, removal of all previous knob and tube wiring, replaced windows, new french door in the living room, new patio and fire pit area, freshly leveled and graveled driveway, two-car carport, refinished front deck, and freshly leveled backyard. Hiking, mountain biking, and snowmobiling trails surround the town, making this home ideal for anyone who enjoys the natural beauty of Vermont. High speed internet is available (currently VTEL).

Listed by Jessica Samples of BHG Masiello Keene

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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87 Trombley Road Andover VT 05143

Andover, VT87 Trombley Road

Price$299,900

Est. Mortgage: $/month

MLS Number 4987366

  • Residential Single Family
  • Full Bath 1
  • Address 87 Trombley Road
  • Construction Existing
  • Bedrooms 2

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 Vermont home overlooking the wonderful stocked ponds! The options are endless--build cabins to use as rentals, great place to homestead as well, massive garden plot already in place.. barn, sheds, and chicken coop ready for animals or for storage of atvs, snowmobiles, or tractors. Plenty of firewood on the property to heat the house! Close access to Vast trails and close to Magic, Okemo, Stratton, and Bromley Mountain for skiing. Several state parks close by for summer swimming, hiking, or kayaking. Manchester, VT is also nearby with lots of shops and restaurants as well! Close enough to town, but far enough out to have plenty of privacy and peace and quiet. Call today for a showing! Agent owned Property.

Listed by Erin Kendall of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.81% last updated on Apr 24, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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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. Data last updated April 30, 2025 6:54 PM EDT