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.

358 Andover Ridge Road Andover VT 05143

Andover, VT358 Andover Ridge Road

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4864436

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 7,589

Tucked away on Andover Ridge Rd you will find one of the most spectacular properties in Southern VT. This remarkable log home features 7 bedrooms and over 7,000 sq ft of finished living space. The main floor is an open floor plan that features, a large kitchen with granite counters, custom cabinetry, top end appliances and an full length of kitchen island. The kitchen opens up to the dining area and a living room that boasts a custom stone wood burning fireplace, vaulted ceilings and floor to ceiling windows that give you breathtaking westerly views for picturesque sunsets and year round enjoyment of all the changing seasons. The main floor also features a den study and an owners en suite bedroom with gas fireplace. The main floor includes multiple accesses to the large wrap around deck looking down to the pond and property. On the second floor you'll find a game room loft and 3 more bedrooms including another en suite master. Down below the finished basement has a large family/ rec room for gathering, 3 more bedrooms with another en-suite master. The lower floor is a walkout to the stone patio that leads down to the amazing lined pond surrounded by incredible stone work, walls and perennial gardens giving you a truly breathtaking setting. The pond even features a waterfall incorporated into the stone work. 72.8 acres with accessible road frontage on Weston-Andover Rd. Possible future development. Just a short distance to Weston, several ski resorts, and VAST trails.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 4837125

  • Commercial
  • Acreage 13.42

Rare opportunity with commercial/industrial zoning. 13+ acres of fully permitted subdividable lots. Property can be used in its entirety, or use what you need and market the permitted land parcels to others. Currently there are 6 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, and rail siding; 7544 sq ft open span, no ceilings, storage building; 3 additional storage buildings. 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. Large former ore shed with 7544 sq ft of open span. Multiple doors to access the building. Survey and permits in place for 7 lot subdivision of the industrial park. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Also offered separately (building lot, ore shed building, or garage/office/storage buildings). Video attached to the MLS.

Listed by Annie Bessette and Andy Paluch of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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1085 Steinle Road Andover VT 05143

Andover, VT1085 Steinle Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 4870084

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,366

At the end of a quiet country road is a two bedroom c1830s brick cape on 251 acres. The property has been called Green Acres since the mid-1800s. The land was farmed for over a hundred years until it was taken over by the Civilian Conservation Corp (CCC) in the 1930s as a forestry camp. Later, it was a retreat for a family who enjoyed summering on the property before there was electricity and modern plumbing. For the last 34 years, it's been stewarded by the current owners who renovated the farmhouse and loved to invite friends and family to share in their slice of heaven. In 1990, a 3 bedroom guest cottage was added to house an overflow of enthusiastic friends and a dog kennel for furry companions as well. They played tennis, kept horses, and loved to ride out on a network of trails. Part of the day was spent swimming and paddling in the clear waters of a 3-4 acre pond, fed by cold mountain springs. The landscape includes perennial gardens and 100 apple trees. There are endless sightings of wildlife including turkeys, beavers, bears, moose, coyotes, deer, and great blue herons. The trails are suitable for biking, cross-country skiing, and hiking. There is a conservation easement, excluding 52 acres. Easements: There is a road easement (right of way to another property) and Velco easement (electric). Showings for the property will begin on July 10th

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$1,135,000

Est. Mortgage: $/month

MLS Number 4869423

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,044

This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to many of Vermonts best ski areas which create an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands including a sugarbush with state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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445 Trebo Road Chester VT 05143

Chester, VT445 Trebo Road

Price$1,075,000

Est. Mortgage: $/month

MLS Number 4860366

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,818

This custom one-of-a-kind timber frame home on 10.6 +/- acres, located just outside of Chester, offers stunning craftsmanship, beautiful scenery, and superior quality. The open layout consists of kitchen, dining, and a great room with vaulted ceilings, and radiant heat maple floors throughout. The first floor extends to an en suite primary bedroom, guest room and guest bath, and an office/study built for two. A separate entrance from the heated two-car garage, complete with interior hose hookups and two floor drains, opens into a mudroom/laundry room with exquisite slate flooring. The modern kitchen includes a built-in grill and stainless steel Energy-Star appliances. Interior solar shades grace the majority of 44 windows on the first floor and finished lower level, also with radiant heat flooring. The second floor incorporates an open loft area overlooking the great room and surrounded by three bedrooms and a full bath. The pastoral grounds accented by stone walls nurture pear trees in front of the home. A hillside backyard is highly favorable for solar panel placements that would remain largely out of view. This idyllic property, close to Okemo Mountain Resort and many exemplary golf courses, is two 5 +/- acre parcels being sold as one, with the second completely wooded for added privacy. Words alone cannot describe the fulfillment of living in this classic Vermont home.

Listed by Suzanne Garvey and Michael Normyle of Mary W. Davis Realtor & Assoc., Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$999,000

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Acreage 548
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 543 +/- acres has it all. Made up of 5 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots as well as a 20.1 acre lot with permitted 1 acre +/- Mica Schist stone quarry. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds throughout offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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753 East Hill Road Andover VT 05143

Andover, VT753 East Hill Road

Price$975,000

Est. Mortgage: $/month

MLS Number 4871985

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 6
  • Square Feet 5,605

Welcome to Alta Vista - Your tranquil and private getaway! This beautifully updated home sits on 19+ acres and is nicely located near Okemo Mountain, the Ludlow Village, Chester, and Weston. If you are looking for that VT farmhouse feel but want modern conveniences and low maintenance, look no further. This meticulous smart home makes it easy for you to turn up the heat while driving to VT or to remotely turn off any lights that you may have left on. The farmhouse is nicely furnished and boasts long-range views, an oversized yard, and a sunken-in hot tub on the deck. The recently built barn acts as a two-car garage with ample storage space for your toys, including your snowmobiles and ATVs as you have access to the VAST trail system from the property. The interior of the home features nine bedrooms plus an office, den, family room, and six baths. While this space is superb for large gatherings, it still feels cozy and comfortable thanks to the genius layout. The home is separated into two different wings with separate staircases but with shared spaces in between. You will find unique details throughout like the original wood ceilings and beams to make this feel like a true Vermont home. You will love the surround sound throughout the house and the automated lights! Of course, the master ensuite bath awaits you to call this place home. Lastly, the home features many updates such as all new mechanicals, windows, insulation, and Hardi plank siding.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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816 Popple Dungeon Road Chester VT 05143

Chester, VT816 Popple Dungeon Road

Price$850,000

Est. Mortgage: $/month

MLS Number 4848206

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,676

Welcome to Deer Valley Farm also known as the Williams Homestead. This is the first time the property has been offered for sale in over 60 years! The home has been lovingly cared for with lots of improvements over the decades of ownership. Outside: The barn has undergone major work which insures its stability for years to come and includes a wine cellar. It measures 45x105 with plenty of room for cars, toys or animals. Other improvements include stonework, tennis court and pool with pool house and gardens. The walking bridge over the Williams River includes 4 staircases to the river and built in lights. The home is styled with Italian tile throughout and offers cozy antique charm with 3 fireplaces. The home does need updating but will be well worth the effort. The structure itself has been well maintained. The large acreage easily lends itself to a few other incredible homesites. Located just outside the town of Chester less than 4 hours to NYC and 2.5 hours to Boston. Minutes to all of Southern Vermont amenities including Okemo, Stratton, Killington, Vermont Country Store, Weston Playhouse, world-class golf and the shops in Manchester. This property will not disappoint.

Listed by Lisa Kelley of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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162 North Hill Road Andover VT 05143

Andover, VT162 North Hill Road

Price$829,000

Est. Mortgage: $/month

MLS Number 4871646

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,723

Beautifully crafted 4-bedroom, three full bath log home situated on 10 acres of rolling meadows with lovely Green Mountain views that extend beyond into New Hampshire. Surrounded by treelined rock walls, and a beautiful ¾ acre stocked pond with a floating swim dock. Just minutes from Weston, Chester, and Ludlow town centers, each offering a variety of restaurants, theater, arts, and shopping. Okemo, Bromley, and Magic Mountains are a quick 15-minute drive, and Stratton is a mere 30 minutes. Short distance to VAST trails. Property consists of 2 deeded parcels with ability to subdivide. The coThe cozy, rustic pine interior contains huge hand-hewn beams, high ceilings and abundant windows with amazing views. The 3-level layout includes a TV/game room on the ground level along with 1 bedroom and full bath. The open concept main floor offers a warm kitchen and living area with high ceilings, and wood burning stove. The spacious loft and master bedroom suite offer ample space for a home office or reading area. Large wrap around deck is perfect for entertaining, grilling or just enjoying the amazing views. The property's 10 acres of usable land offers endless options for campfires, fishing, yard games, sledding or simply enjoying the peaceful tranquility and abundant wildlife. The house is backed up by a new 11kw standby generator. All heating and water systems have been serviced regularly and well maintained. High speed internet is available. Two car garage with plenty of storage.

Listed by Jason Saphire of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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698 VT ROUTE 11 West Chester VT 05143

MLS Number 4820670

  • Commercial
  • Year Built 1810
  • Acreage 5.63

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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698 Vermont RT 11 Chester VT 05143

Chester, VT698 Vermont RT 11

Price$650,000

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 12
  • Square Feet 6,848

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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2172 North Hill Road Andover VT 05143

Andover, VT2172 North Hill Road

Price$595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4854484

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,745

This well maintained three bedroom home plus bonus room boasts a private location set back off a country road where the present owners have cleared some land to open up a spectacular hill top view and bring in the morning sun. Located in the heart of the southern Vermont Green Mountains, it has easy access to Okemo Mountain to the north, Stratton, Bromley and Magic ski resorts to the south. The VAST snowmobile trail network is right outside your door. When the snow melts and the Green Mountains turn green again, the Weston Playhouse, various local lakes and ponds with public access and an abundance of hiking and biking trails await you.

Listed by Suzanne Garvey and Boris Lavanovich of Mary W. Davis Realtor & Assoc., Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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266 Main Street Chester VT 05143

MLS Number 4837044

  • Commercial
  • Year Built 1780
  • Acreage 0.75

This circa 1780's stunning, country inn is located in the heart of Chester and southern Vermont, the ideal setting for a hospitality business. Owned and operated with care, this home and it's owners have provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. This well established business is ready for you to put your mark on the hospitality for the long list of returning guests! The 7 guest rooms and common areas are fully furnished. The newly renovated owners quarters, including two spacious bedrooms, will be unfurnished allowing your own personal décor. Enjoy a comfortable lifestyle in Vermont, in concert with your guests! The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax. The central village location allows easy access to the surrounding community on foot!. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney and Joan Morey of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$579,000

Est. Mortgage: $/month

MLS Number 4845016

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Acreage 0.75

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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38 Vt Rte 11 West Chester VT 05143
Active With Contract

MLS Number 4851883

  • Commercial
  • Year Built 1904
  • Acreage 0.87

The Historic Wylie House on .87 +/- acres with 12 bedrooms and 5 baths would lend itself to many commercial uses such as office/professional space, bed and breakfast, mutli-units, air b&b rentals, a retreat or a ski house. An owner occupied therapeutic retreat for many years, the property would also convert to a 3 unit or as owner occupied with a 2 unit rental that would be easily leased, rentals are in demand! A large 2 story addition with radiant heat would make a wonderful professional meeting space, yoga/exercise space or alternative school. The adjoining barn with efficiency kitchen, 3 bedrooms and bath could be an event space or separate apartment. The yard has multiple, customized sheds including a sauna, an office/studio with heat and water, a work shop, garden shed, potting shed and gazebo. A whole house propane generator and outdoor wood boiler provide back up and alternative heat. The yard adjoins the town park in the back which offers skating, disc golf, skateboard park, outdoor pool, tennis courts and a sledding hill.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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38 Vt Rte 11 West Chester VT 05143

Chester, VT38 Vt Rte 11 West

Price$550,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4850599

  • Residential Single Family
  • Construction Existing
  • Bedrooms 12
  • Bathroom 5
  • Square Feet 5,976

Welcome to the Wylie House, a historic 12 bedroom, 5 bath home on .87 acres with many original details such as Victorian gingerbread, stained glass, an elegant period stairway and a rustic, original 2 story barn. The updated kitchen has attractive tile flooring, crown moldings, center island and a lovely eat-in area with a nook to enjoy morning coffee/tea. The living room has a brick hearth for a wood or pellet stove and built-ins for a great study/home office. The main bedroom features a lovely picture window overlooking the garden & a full bath w/clawfoot tub. An additional front bedroom could also serve as living area. Upstairs there are 2 baths, 5 bedrooms and a finished 3rd floor w/full bath, common area and two additional bedrooms. A 2004 addition adds a spacious gathering room that opens to the large rear deck. A huge, light and bright bonus space w/cathedral ceilings on the 2nd floor is perfect for yoga, a home theater, craft room or professional space. The attached rustic 2-story barn is an amazing space w/an efficiency kitchen, woodstove, full bath, laundry area and large picture window. A custom detailed stairway leads to 3 bedrooms on the 2nd floor. The yard has been lovingly cultivated with perennial gardens and features a garden cottage shed, outdoor sauna, workshop, studio/office wood storage and gazebo. An auto generator keeps things running smoothly and an outdoor wood boiler is a great alternative for heat! Next to town rec area & walkable to town.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 4837151

  • Commercial
  • Acreage 2.49

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. Also available separately (building lots, ore shed building, or the entire parcel-see MLS 4837125). Video attached to the MLS.

Listed by Annie Bessette and Andy Paluch of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 Dorman Road Andover VT 05143

Andover, VT663 Dorman Road

Price$449,000

Est. Mortgage: $/month

MLS Number 4871500

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,472

What is the value of 7,466 acres of State forest connected to your property? This unique property has been nurtured by it's owner for many years. It has been a place of quiet and calming features with abounding wildlife. The grounds have been manicured. The tiny A-frame has been enlarged to a comfortable country sanctuary! Experience a completely open kitchen, living, and dining room with a winding staircase to the loft and large windows, allowing plenty of light and vision of the beautiful outside! This type of property is so hard to find! A visit is the best way to recognize the incredible features. The property is completely furnished down to the tools and tractor!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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Little Pond Road Andover VT 05143

Andover, VTLittle Pond Road

Price$425,000

Est. Mortgage: $/month

MLS Number 4788146

  • Land
  • Acreage 100
  • Area Rural
  • Utilities None
  • Zoning Res

This exceptional 100-acre parcel is privately sited with spectacular 180-degree views of the Green Mountains and Stratton Mtn. Located within five miles of Weston and Londonderry, the property is in good company of other substantial parcels. The private driveway leads to the house site on a prominent knoll providing the advantage of an amphitheater with privacy on all sides. A waste water permit is in place for 6 bedrooms. Bring your own builder or the owner will help with build-to-suit. Within 12 miles of Bromley Mtn., and 16 miles of Stratton Mtn.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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693 Lovers Lane Road Chester VT 05143

Chester, VT693 Lovers Lane Road

Price$425,000

Est. Mortgage: $/month

MLS Number 4875140

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,613

On one of the best locations in town you will find this well cared for 3 Bedroom saltbox home on 5.5 private acres just 1 mile from the village. The home is full of charm and many highlights. You'll find a large country kitchen with a ton of counter and cabinet space with an eat in breakfast area that opens up to the side yard deck. The kitchen has a pass through opening to the dining room which has a slider door to a private 10X20 deck ideal for relaxing. The first floor also boasts a good sized living room with woodburning stove, big den that has multiple uses, 1/2 bath and laundry/pantry/coat room off kitchen. The second floor gives you 3 good sized bedrooms including an owners bedroom with private bath and an office perfect for working at home with fiber optic internet available. Hardwood floors are found throughout the first 2 floors. The basement features a huge rec room with a walkout to the backyard. The property itself is exceptional. 5.5 acres, much of it open featuring a side yard along the road hidden by a privacy fence. The other side of the house features the deck where you can sit and listen to the bordering Lover Lane Brook. The backyard slopes down to the firepit and an open field that will make you feel like you are away from it all even though your only a mile from town. The location is perfect!. Just a 20 minute drive to Okemo and close proximity to the VAST trials. The Chester Town Recreation center is just down the street. A must see!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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225 Pleasant Street Chester VT 05143

Chester, VT225 Pleasant Street

Price$374,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4826630

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Square Feet 5,788

Don't miss this comfortable Victorian home, having been a successful Inn for many years, will also be a wonderful location for the life style of your family, be it a business or a residence. With 9 bedrooms and 8 bathrooms plus parking for 8-10 vehicles there is ample space to run an Airbnb or host a large family retreat. With several ski resorts all under 30 minutes away this is an ideal property for a ski/recreational club house. There is plenty of room to entertain with a large dining room, living rooms and the old tavern with a large deck for lounging, after a day of exploring the area. The property has been lovingly maintained and it shows. Just moments from the quaint Village of Chester and quick access to I-91, it is conveniently situated to access all the wonders Vermont has to offer. This is without doubt a special place with the value you are seeking! Come, look, see for yourself!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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1923 North Hill Road Andover VT 05143

Andover, VT1923 North Hill Road

Price$359,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4866402

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,316

Peace and quiet can be yours in this 1980s chalet on 13+ acres. A super country location, set back from the road in a park-like setting, yet easy access to all area amenities. Three levels of living space with three bedrooms and three baths. Relax on the deck with a book in the summertime or take a dip in the pond. In wintertime you can warm up in front of the main level or lower level fireplace. Lots of knotty pine walls and trim provide a true Vermont rustic ambiance. Beautifully landscaped with carefree perennials and flowering shrubs. If you would like more land the abutting 13 acre lot is also available to purchase for a total of 27.30 acres (see MLS 4866868). Be it skiing at nearby Okemo, snowmobiling from the VAST trail network or hiking on nearby trails this residence can be a year-round home or vacation retreat.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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99 Pettengill Road Andover VT 05143

Andover, VT99 Pettengill Road

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4857137

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,150

What a charming place to escape to! This updated farmhouse has excellent use of space and a great layout! Plenty of room for toys or animals, use the outbuildings as you please! There are several rich garden spaces, berry bushes, perennial gardens and a stone terrace with a fire pit for sitting back and enjoying life. Fiber optic internet allows for the ideal work from home opportunity. There is master bedroom on the main floor, 2 additional bedrooms above and a large bedroom or office space over the garage. The horse barn has 3 stalls, a tack room and hot/cold running water and a tractor shed, the second vintage barn has endless potential. Pettengill Road is centrally located in Andover, within an easy drive to Okemo, Magic, Stratton and Bromley as well as the town of Chester and Londonderry for groceries. Just a quick trip over the hill to Weston and the Weston Playhouse. This sweet home is move in ready with many recent improvements. This spot will be a wonderful location to call home!Showings begin April 24, 2021.

Listed by Alison Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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90 Common Street Chester VT 05143

MLS Number 4872901

  • Commercial
  • Year Built 1880
  • Acreage 0.16

A fantastic business and investment opportunity on the Chester Common. One of the towns Victorian crown jewels is ready for it's new owners. The first floor commercial space has been the long time home of successful restaurant ventures over many years. The property is completely set up and ready to go with a fully loaded commercial kitchen that was redone new in 2014. 65 seat facility with enclosed front porch seating with windows looking out over the common. Also features an inviting bar area as you walk in. Basement is set up for storage and has a large walk in refrigerator. Many recent updates including electric, plumbing and foam insulation. Upstairs you will find a second floor front office overlooking the common as well as a spacious 2,100 sq ft 2 bedroom apartment with back living room with deck access, full kitchen, dining room, laundry room and extra finished living space on the third floor. This property is ideal for a chef-owner who would like to live and work in a beautiful town setting. Also great extra income potential using the upstairs apartment as a rental. Located in an area of Vermont that is vibrant in all seasons. Near several major ski areas, all town amenities and convenient access to route 91. Come and take a look.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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90 Common Street Chester VT 05143

Chester, VT90 Common Street

Price$349,000

Est. Mortgage: $/month

MLS Number 4872902

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 4,026

One of the towns Victorian crown jewels is ready for it's new owners. Two Bedroom apartment with over 2,000 sq ft of living space located right on the chester common. Apartment boasts a large living room with a gas fireplace, deck of the entry. Good sized kitchen with large dining room and an extra 400 sq ft of living space on the finished third floor. The first floor commercial space has been the long time home of successful restaurant ventures over many years. The property is completely set up and ready to go with a fully loaded commercial kitchen that was redone new in 2014. 65 seat facility with enclosed front porch seating with windows looking out over the common. Also features an inviting bar area as you walk in. Basement is set up for storage and has a large walk in refrigerator. Many recent updates including electric, plumbing and foam insulation. This property is ideal for a chef-owner who would like to live and work in a beautiful town setting. Also great extra income potential using the upstairs apartment as a rental. Located in an area of Vermont that is vibrant in all seasons. Near several major ski areas, all town amenities and convenient access to route 91. Come and take a look.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 July 31, 2021.