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: 6.96% last updated on Jan 23, 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: 6.96% last updated on Jan 23, 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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0 Howard Hill Road Andover VT 05143

Andover, VT0 Howard Hill Road

Price$1,999,500

Est. Mortgage: $/month

MLS Number 4990472

  • Land
  • Address 0 Howard Hill Road
  • Acreage 297.52
  • Area VT-Windsor
  • PricePerSqFt 6720.56

You've got creative visions - We've got your canvas Immerse yourself in the tranquility of nature as you explore the mature maples,ponds, meadows, stone walls and vista views of this remarkable 200.27-acre property. Whether you're seeking a private retreat, an investment opportunity, or your dream home, this property offers the perfect blend of natural beauty, seclusion, and potential. The possibilities are endless. Don't miss your chanceto own a piece of Vermont's pristine landscape. Schedule a viewing today and let your imagination take flight!

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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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1328 Chandler Road Chester VT 05143

Chester, VT1328 Chandler Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 5002063

  • Residential Single Family
  • Full Bath 2
  • Address 1328 Chandler Road
  • Construction Existing
  • Bedrooms 4

Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside a wide-open main living area and great room overlooks the 10 foot deep swimming pond, and the nearby stream can be heard from the deck or kitchen with the windows open. Step into the luxurious primary suite, a sanctuary with large windows and a spa inspired bath with a free-standing tub that boasts one of the best views from the house. Enjoy the newly renovated lower level with additional bedrooms and expansive family room. This area is ready for your touch and enjoys walkout access to the yard and pond. The 2nd level of the barn is currently a wood shop with wood-stove and a 2nd access from the road allows for storing large pieces or equipment on this upper level. The ground level of the barn has traditional sliding barn doors and extensive parking in front. Underground power and water lines travel from the house to a nearby site where another barn or horse arena could be built. A unique home treasure and like its organic architectural design the land has its own special quality of character and beauty. 191 acres are in the VT Land Use program. There is a 6 bedroom septic.

Listed by Suzanne Garvey and Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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: 6.96% last updated on Jan 23, 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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Howard Hill Road Andover VT 05143

Andover, VTHoward Hill Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 4990111

  • Land
  • Address Howard Hill Road
  • Acreage 111
  • Area VT-Windsor
  • PricePerSqFt 10810.81

You've got creative visions - We've got your canvas Immerse yourself in the tranquility of nature as you explore the mature maples, ponds, meadows, stone walls and vista views of this remarkable property. Whether you're seeking a private retreat, an investment opportunity, or your dream home, this property offers the perfect blend of natural beauty, seclusion, and potential. The possibilities are endless. Don't miss your chance to own a piece of Vermont's pristine landscape. Schedule a viewing today and let your imagination take flight!

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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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354 Miner Road Chester VT 05143

Chester, VT354 Miner Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 5017587

  • Residential Single Family
  • Full Bath 2
  • Address 354 Miner Road
  • Construction Existing
  • Bedrooms 3

Chase Brook Farm is at the end of a quiet country road, offering complete privacy on 53 acres and yet just 10 miles from Okemo Ski Resort, fine dining, and shopping. The views are punctuated by bucolic vistas of the Green Mtns including Steadman Hill, the highest peak in Chester. At the center of this property is a 2,941 s.f. farmhouse, built in 2008 and inspired by countless visits to Sturbridge Village. Thoughtfully designed to evoke the charm of a historic home, it features hand-planed boards, painted wide pine floors, wrought iron latches, and soapstone countertops while providing the comfort of modern amenities, including new mechanicals, updated wiring, and a large, dry basement. This property invites year-round enjoyment. In winter, sled down hills out back, or clear the pond for skating parties. Snowmobilers, skiers, and snowshoers will appreciate the room to roam and easy access to the VAST trail. After a day in the snow, warm up by one of the two cozy fireplaces or take a soak in the hot tub. In summer, enjoy a swim or cast a line in the stocked pond, or gather berries from the 80+ blueberry bushes and raspberry patch. The fall season brings apple picking and the land is suitable for livestock, offering versatility for a variety of uses. Chase Brook weaves in and out along the border to the East. Additional features include an attached 1-bay garage, a 3-bedroom caretaker's house with a 3-bay garage, and fiber optic internet. Showings begin October 11.

Listed by Dia Jenks and T Story Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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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157 Thompson Road Chester VT 05143

Chester, VT157 Thompson Road

Price$995,000

Est. Mortgage: $/month

MLS Number 5000207

  • Residential Single Family
  • Full Bath 2
  • Address 157 Thompson Road
  • Construction Existing
  • Bedrooms 4

Welcome to this beautiful historic farm dating back to 1825. At one time known as the Thompson Farm, in 1995 it was purchased by the current owner who lovingly restored it to its former glory. In 1999 it became the "Jersey Girls Farm". Attention was given to retain all of the antique charm, including keeping the original slate roof on main house, all original doors and original wide board floors. The house was also modernized with conveniences such as a new heating system, new wiring, new windows (retaining the original design), and a full array of solar panels to make the house fully self-sufficient. You will find plenty of room and charm inside, beginning with the large country kitchen which includes a working antique Glenwood stove. There's a huge pantry which doubles as a laundry room. The dining room, living room, library, one bedroom, and spacious 1/2 bath complete the downstairs living area. On the second level are 3 large bedrooms and a full bath in the main structure. The expansive master suite even has a spa tub! This room has a 2nd stairway which leads you back to the kitchen. On almost 33 acres of open and wooded land, all of which sits at the end of a town-maintained road. There's a large pond for swimming, fishing, or even kayaking. 5 outbuildings including a nice 1800's 30 x 80 barn! Endless possibilities: small dairy or horse farm, Airbnb, or bed and breakfast. Just 5 minutes to Chester. Shopping, hospital, skiing at Okemo, I-91 - all within 15 - 20 minutes!

Listed by Glenn Olney and Chelsea Cary of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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$699,000

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: 6.96% last updated on Jan 23, 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: 6.96% last updated on Jan 23, 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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2510 East Hill Road Andover VT 05143

Andover, VT2510 East Hill Road

Price$649,500

Est. Mortgage: $/month

MLS Number 5025605

  • Residential Single Family
  • Full Bath 1
  • Address 2510 East Hill Road
  • Construction Existing
  • Bedrooms 3

This home on East Hill Road commands one of the area's best views. 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 for you. A large mudroom with a slate floor & lots of cubbies is the perfect entry. Off to the right is the woodshed where you can gather your wood without having to go outside! The living room is a large front to back room with a woodburning fireplace on one end & the mountain view on the other. The dining & kitchen are gorgeous with excellent cabinetry & appliances. The primary bedroom/bath are located on the first floor where you enjoy the long-range views before you are even out of bed. Upstairs are two lovely bedrooms & bath. The natural light throughout the house is just terrific. On the lower level you will find up to date mechanicals & a super room for fun with a small bar & pool table! This home was built in 1978 & expanded with the architect designed addition in 2018. The quality is evident throughout. Between the quality, the setting, deck & the views, you will want to call this home forever. Fiber optic internet will let you work from home so you might as well stay put! Less than 8 miles to either Okemo or the Weston Playhouse. So many activities nearby. Skiing, hiking, golf, cycling, snowmobiling, the lakes. This is your spot to call home!

Listed by Betty McEnaney of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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

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: 6.96% last updated on Jan 23, 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$598,000

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! Added bonus is owner is willing to offer financing with 30% down payment to approved buyer.

Listed by Erin Kendall of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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: 6.96% last updated on Jan 23, 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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686 Green Mountain Turnpike Chester VT 05143

MLS Number 4995602

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2

This charming home in Chester combines Vermont's rural charm with modern amenities. Surrounded by the serene beauty of Fox Chair Mountain, it offers an enchanting escape from daily life's hustle and bustle. Within the home, you'll find cozy spaces perfect for relaxation. From the inviting great room that opens onto a beautiful stone patio to the tranquil library, or the large private deck off the primary suite, and even the attached horse barn, there are several private areas to unwind and rejuvenate in this retreat. With two fireplaces and a wood stove, this home ensures comfort year-round. The modern kitchen is central to the flowing home and the porches and stone patio make gathering with friends and family a breeze whether it be an intimate dinner or a large crowd. The home's southern exposure over a stunning alpine valley provides endless opportunities to appreciate Vermont's natural beauty. With a rich history as a working farm, this property is ready for its next chapter. Additionally, beyond the 3-acre home site being offered is the opportunity to own a further 90+/- acres of stunning land with an outdoor riding arena, and perhaps an opportunity to create additional building lots. Whichever you choose you will find yourself poised for the enriching experience of living in this captivating haven. Don't miss the chance to create your sanctuary in Vermont. Schedule a viewing today and explore the possibilities of this pastoral paradise.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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: 6.96% last updated on Jan 23, 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$509,000

Est. Mortgage: $/month

MLS Number 5024539

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

Step into the charm of yesteryear with all the comforts of today at 663 Depot Street. This completely renovated 3-bedroom, 2-bathroom home combines historic character with modern convenience. Since 2022, everything from the insulation, drywall, electrical, plumbing, & HVAC has been updated, including a new furnace, water heater, fixtures, countertops, cabinets & appliances. The only original feature left untouched is the flooring- beautifully refinished original wood. The owners thoughtfully chose period-appropriate paint colors & preserved unique touches like exposed beams & original woodwork. You'll love the Victorian martini pedestal sink in the upper bathroom! There is also a 2-story attached post-and-beam barn-larger than the house itself-with a powered overhead door. Keep it as a garage or workshop, or explore the incredible potential to double your livable space by finishing it. Sited on 1 acre, the property has a sprawling lawn, fire pit for evenings under the stars & an unbeatable location near Chester's Stone Village, Grist Mill, Smitty's Market, & other local amenities. Just 15 min to Okemo Mtn & the lakes, 30 min to Bromley, & under an hr to Killington, Stratton, & Mt Snow-a prime spot for skiing, hiking, & year-round fun. Currently used as both a family getaway & a successful Airbnb, this property has serious income potential for those looking to maximize its use. Whether you're searching for a primary home or an investment, this timeless home is not one to miss.

Listed by Betsy Adamovich of Real Broker LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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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566 Simonsville Road Andover VT 05143

Andover, VT566 Simonsville Road

Price$499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4994070

  • Residential Single Family
  • Full Bath 1
  • Address 566 Simonsville Road
  • Construction Existing
  • Bedrooms 3

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 updated with modern amenities such as first floor radiant heat, central air and chef's kitchen with a professional 48" Dacor range with double ovens, ensconced in an arched, brick hearth complimented by cherry cabinets, walk-in pantry and attractive island and curly maple counters. Period details have been carefully attended to with custom interior shutters, replacement windows, a Monson slate roof, preserved softwood pine floors, clawfoot tub, custom copper top vanities/sinks and three fireplaces. A walk-up attic offers storage or additional space to finish. A recently added detached two bay post and beam garage adds both character and utility with oversized doors for RV use. The "kissing bridge" serves as a woodshed and an auto generator adds peace of mind. A screen house nestled by the river is great for cookouts. Two barns, original mill stones and a historic logging road reflect the property's history along the Williams River for over 200 years. Convenient to skiing. 6.85 acres includes a 3.49+/- acre lot w/state approved wastewater permit for 4 bedroom home. Easy access to skiing.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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

$
$
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$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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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12 Common Street Chester VT 05143
Active With Contract

MLS Number 5005505

  • Commercial
  • Address 12 Common Street
  • Year Built 1820
  • Square Feet 4,060
  • Acreage 0.25

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential for more units. The first being the business store front with great road visibility and rustic features like the two sided fireplace chimney, the second is a space in the back which could easily be turned into a long term rental with a kitchen and separate bathroom, the third is a second floor 2bedroom 1 bathroom which has recently been updated and rented with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's location comes parking right on the Green and behind the building with an owned park area. Some recent updates are the back portion on the building has a new roof and $80,000.00 worth of solar was added to the whole building making the electric bill extremely low.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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: 6.96% last updated on Jan 23, 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: 6.96% last updated on Jan 23, 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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491 Farrar Road Chester VT 05143

Chester, VT491 Farrar Road

Price$439,000

Est. Mortgage: $/month

MLS Number 5000203

  • Residential Single Family
  • Full Bath 2
  • Address 491 Farrar Road
  • Construction Existing
  • Bedrooms 4

Nestled on a serene, quiet town maintained dirt road, this spacious home offers the perfect blend of tranquility and comfort. As you approach, you'll be captivated by the stunning long-range views that greet you from the expansive deck, a haven for relaxation and outdoor enjoyment. The deck overlooks a picturesque pond, not on the property but offering a beautiful, calming view that enhances the natural charm of the setting all the same. Step inside to discover a thoughtfully designed interior where ample space meets cozy. The large, finished basement is a true bonus, featuring a cozy and convientent propane stove and serving as an ideal games room or entertainment space for family and friends. Featureing 4 large bedrooms, 3.5 bathrooms, with large primary ensuite, large living room with views and that all enticing party or craft space in the below. This is equally a perfect vacation retreat or spacious family home. Conveniently located close to the popular ski areas of Okemo, Stratton, and Magic this home is perfect for winter sports enthusiasts. Whether you're seeking a peaceful year-round residence or a seasonal getaway, this property promises a lifestyle of serene beauty and endless recreational opportunities. Welcome home to your personal oasis.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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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102 Church Street Chester VT 05143

Chester, VT102 Church Street

Price$439,000

Est. Mortgage: $/month

MLS Number 5024148

  • Residential Single Family
  • Full Bath 1
  • Address 102 Church Street
  • Construction Existing
  • Bedrooms 4

A classic, easy maintenance four bedroom, two bath home in Chester village on .12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and elegant lighting, a country kitchen with marble tile flooring, first floor bath with tiled shower and an adjoining bedroom with a lovely reading/entertainment nook that connects with the dining room. The second floor has a large landing with two adjoining bedrooms, a full bath with radiant heat in the floor and a cool, private back bedroom. The basement has foam insulation and the windows, water heater and oil tank have been replaced. Ready for your enjoyment as primary, secondary or investment property. Close to Magic, Okemo, Bromley and Stratton Resorts, and year year-round recreational activities.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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 Andy Paluch of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 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 January 25, 2025 10:53 AM EST