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.

465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$1,685,000

Est. Mortgage: $/month

MLS Number 4918189

  • Residential Single Family
  • Square Feet 4,444
  • Bedrooms 4
  • Construction Existing
  • Bathroom 5

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 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 a 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 private 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: 6.7% last updated on Sep 29, 2022
* 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

141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$924,000

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Area Near Skiing, Rural
  • Acreage 509.73
  • 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 509+/- acres has it all. Made up of 4 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. 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 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

345 Hill Top Road Andover VT 05143

Andover, VT345 Hill Top Road

Price$825,000

Est. Mortgage: $/month

MLS Number 4924888

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Square Feet 4,255
  • Bedrooms 4

Enter up a gently curving drive bordered with mature hydrangea trees to discover this handsome, privately sited post and beam with wraparound deck and Palladian windows to take in the spectacular mountain view. The 38+ acres are graced with wildflower gardens, a swimming pond and dock, a dream of a sledding hill, and woodland trails that run the extent of the property. The wide pine floors, three stone fireplaces, a new system of heating and air conditioning mini splits, and high-speed fiber optic internet speaks comfort and quality. The main level includes living, kitchen and dining rooms, a primary bedroom/den with fireplace and a full bath, a home office with custom cabinetry, a mudroom/laundry room, and a glassed-in hot tub for relaxing and stargazing. Upstairs you'll find a second primary with ensuite bath and two guest bedrooms, one with outdoor balcony, and a shared full bath. The finished basement expands your living space with a large, open family room and recreation room, a bonus room and 3/4 bath. Hill Top Road is a choice location with lovely homes and a historic farm, close to VAST Trails, Lowell Lake, and Magic Mountain, and convenient to Weston's theater and Vermont Country Store and to Ludlow's Okemo Mountain Resort and restaurants. A much-loved family retreat, this special home now awaits its next lucky owners. Property being sold "as is" and priced accordingly. Purchasers may do inspections for their own information. All measurements approximate.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

374 Richardson Road Chester VT 05143

Chester, VT374 Richardson Road

Price$699,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4908861

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,776
  • Bathroom 2
  • Bedrooms 3

Gracefully settled between the villages of Chester and Londonderry, sits a Vermont Farmhouse at road's end, sited on eleven+ acres of wood'n meadow. Dotted with old stone walls, a wildlife pond and enchanting views. The setting is magical. A wide country porch invites rocking chairs and visitors while the screened area encourages outdoor entertaining much of the year. The vintage flavor is apparent throughout the home- opening panel doors with antique latches or stepping foot on wide wood floors milled from indigenous trees from decades ago. This location is central to recreating: ski, hike, snowmobile, swim, or enjoy our local restaurants, theater and shopping. A center island kitchen with breakfast nook overlooks the rolling meadows and glass doors allows life to spill over onto the porch, deck or firepit area. A traditional dining room, adjacent to the intimate living room, awaits memorable dinner parties. The great room's remarkable soaring ceiling creates a central gathering spot and includes a cast iron wood burning stove to warm by when winter is settling in and snow abounds . The main floor bedroom would also make a delightful home office overlooking the fields to the rear. Upstairs you'll find additional bedrooms including a large “beamed ceiling” primary and a fun multi-functional den/game room. Two sets of farmhouse stairs give easy access. If quiet and open and vintage is your desire..Look no further. Showings begin Thursday, May 12th. Owner is a licensed Realtor.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Little Pond Road Andover VT 05143

Andover, VTLittle Pond Road

Price$698,000

Est. Mortgage: $/month

MLS Number 4919925

  • Land
  • Acreage 100
  • Area Near Skiing, Rural
  • Zoning Res. 2 acres

Sequestered in the rolling hills of Andover surrounding Cobble Hill and Lowell Lake State Park, this spectacular, secluded parcel of 100 +/- surveyed acres features unparalleled 180 degree panoramic Southwesterly views. Winding through woods and along glimpses of stone walls, the gentle approach of the driveway culminates in a magnificent place of solitude overlooking the distant, majestic mountains of Stratton and Bromley, a combination of views and privacy truly unrivaled and hard to find in this area. The cleared house site has an approved wastewater permit for up to 6 bedrooms and would accommodate a spectacular, dramatic showcase home. With a little more clearing to the East, it's possible to expand the view to include Magic and Haystack Mountain. Seller to bring power and driveway to the edge of the building site. VTel Fiberoptic internet is available for working remotely while enjoying the VT eateries and craft beer, Summer Theater at the Weston Playhouse, farmer's markets and skiing at Magic, Bromley, Stratton, Okemo or Killington Mountains. For the more adventurous, hike and snowshoe 100+/- acres of your own untouched wilderness!

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

166 North Street Chester VT 05143

Chester, VT166 North Street

Price$695,000

Est. Mortgage: $/month

MLS Number 4923376

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 3,744

Unique opportunity to own a piece of history. This six-bedroom, five and a half-bath home on .67 acres is nestled in the heart of the historic stone village. Chester's stone village is currently recognized by the United States Department of Interior as perhaps one of the only stone villages in the country. This two-story federal-style stone home offers many opportunities with its spacious floor plan. Enjoy flexibility with an accessory apartment above and fully renovated owner's quarters below. Walk the grounds to enjoy the patio with its own stone cottage that is currently used to make maple kettle corn. Cross the garden bridge on your way to the lily pond or enjoy the shade from one of the fruit trees. The property offers the best of both worlds with a sprawling backyard yet conveniently located to restaurants and shopping. Okemo Resort and the lakes region are just a quick 12 miles away. This location offers lots to do each season including festivals, the Weston Playhouse, concerts, and much much more. Taxes are based on current town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

Stage Road Chester VT 05143

Chester, VTStage Road

Price$622,650

Est. Mortgage: $/month

MLS Number 4931759

  • Land
  • Acreage 296.5
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning property has it all. Made up of 3 contiguous preexisting lots with a right of way via 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. 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 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

7 Pine View Drive Chester VT 05143

MLS Number 4908570

  • Commercial
  • Year Built 2006
  • Square Feet 3,164
  • Acreage 1.56

Excellent opportunity presents itself with this outstanding commercial property located on Route 103 Chester. High volume traffic and exposure gives this property unlimited potential for the entrepreneur buyer. This exceptional post and beam structure sits on 1.56 acres and was built in 2006. Currently used as office space, it had been a retail shop, gallery and cafe in the past. Mixed use zoning allows for a future residential possibility. Over 3,000 usable square feet, ample parking, radiant heat, gorgeous tile flooring, natural wood beams. Town water and septic hooked up to the town line. Bring your vision and energy and create your dream.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

12 Common Street Chester VT 05143

MLS Number 4928621

  • Commercial
  • 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! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2 bedroom 1 bathroom with much potential! Along with the many benefits of this properties location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added recently as well.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

95 Church Street Chester VT 05143

Chester, VT95 Church Street

Price$495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4927983

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Square Feet 2,794

Welcome to 95 Church St in the charming town of Chester. This 1800's home has seen many changes over the years including most recently a whole house renovation. This is a great property for someone that loves the charming features of an older home but in turn key condition. Renovations include but are definitely not limited to the kitchen, bathrooms, flooring, windows, heating systems including in floor radiant heat, siding, electrical, pex plumbing, spray foam insulation, and a new standing seam roof. The kitchen features beautiful hand made cherry cabinets with custom pantry cabinets as well. While we are talking about cabinets the walk-in closet features walnut shelving and drawers. The floors throughout most of the home are a beautiful hickory. In addition to the the two bathrooms there is an en suite bathroom that is ruffed in and waiting for your final touches. Sit back and enjoy the village location from the screened in porch or patio.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

498 Marcs Drive Chester VT 05143

Chester, VT498 Marcs Drive

Price$490,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4924119

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,564
  • Bathroom 3
  • Bedrooms 4

Welcome to Vermont living! This spacious, well-kept home has lots of room for your family, pets, and even an RV in the oversized garage! Situated on over 2.5 acres, there is plenty of privacy. The beautiful yard includes raised beds for veggies or flowers as well as a fenced in area for your animals to stay safe. Located just outside the village of Chester, this home is within 30 minutes to several ski areas. There is a hospital just 15 minutes away as well as grocery and restaurants. Access to VAST trail system right from Marcs Drive. The home is filled with lots of natural wood along with plenty of windows. Downstairs you'll find a large master with an en-suite bath and two closets. The master has a radiant heat floor. The laundry room is also conveniently located on the lower level. Upstairs the three bedrooms and a bath offer plenty of space for the family. Over the garage is an office, and in the basement there's a big bonus room with a walkout into the yard. High speed fiber internet is installed; perfect to work from home. Some of the recent improvements include: paving the driveway; installing a split pump (a/c - heat), staining the house, a new well pump, and installing a bay window. This home has three heating systems and is wired for and includes a portable generator. There isn't much to do here except move in!

Listed by Heather Gleim of Walnut Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

81 Main Street Chester VT 05143

Chester, VT81 Main Street

Price$479,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4929143

  • Residential Single Family
  • Bathroom 4
  • Construction Existing
  • Bedrooms 5
  • Square Feet 3,864

Welcome to 81 Main Street! Built in 1820 and located in the heart of the Chester village, this property is historically known as the Guy Earle House and has been a year round vacation home and short term rental property. This quintessential VT gem on .44 acres+/- features 5 bedrooms and 4 baths. Among it's many attractive features are a large living room with wood burning fireplace, formal dining room, two first floor bedrooms, one en suite and an additional bathroom. The 2nd floor includes a large living area, en suite bedrooms, a bonus game room with a handsome wet bar, hand-crafted from school benches. and a pellet stove. Additional Features include: first floor laundry, mudroom/workshop and unfinished attic space. The double lot has generous parking, an oversized 1 car detached garage with potential space to be finished and a separate shed for gardening in the large level yard. The 4 porches adorning the house offer outdoor covered gathering spaces. Stroll to the green for coffee and browse the shops. Close to 5 ski areas, recreational activities and year round fun!

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

3778 Trebo Road Chester VT 05142

Chester, VT3778 Trebo Road

Price$429,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4924795

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,456
  • Construction Existing

This immaculately maintained home was built in 2013 and is situated on over 23 acres with a pond and oversized 3-car garage! Enjoy privacy and solitude with plenty of room to garden, hike, cross country ski or snowshoe without ever leaving your own property. If motorized fun is more your style, there is ample indoor storage space for snowmobiles, boats or ATV's. When at full capacity the pond is 12 feet with a sandy "beach" area. Add a floating swim platform for summer fun or enjoy the peaceful spot with a fire in the large stone hearth pond side. The home itself is bright and cheery with open concept living spaces that open to either the front deck or back deck and patio spaces for a great indoor/outdoor flow. Primary suite with large full bath, double sinks, soaking tub, and additional shower. On the other end of the home are a guest bedroom and den with an additional full bath. Also on the main floor is a spacious and functional mud room with a utility sink and full laundry. If you need more space, the full basement is clean with large windows, high ceilings and could be finished to suit. Heated garage w/3 large bays, workshop space and full second floor for recreation, office space, or could be finished for more living area. If you do find yourself out and about there is plenty to do nearby. Okemo Resort is only 12 miles away and downtown Chester boasts many boutique shops, restaurants, yoga, and art studios, farmers' market and more! Showings begin Sunday Aug 14.

Listed by Jacki Murano of Southern Vermont Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1749 Middletown Road Andover VT 05143

Andover, VT1749 Middletown Road

Price$399,000

Est. Mortgage: $/month

MLS Number 4910880

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Square Feet 1,504
  • Acreage 31

This glorified camp on 31 gorgeous and secluded acres offers tons of natural light and is just waiting your finishing touches! Drive down the gently winding driveway that is hugged by both hard and soft woods to a spacious clearing where you will find the camp, firepit, outhouse, and stream running across the south side of the lot. The property has electric, forced air propane heat and a wood stove. There is no running water however there is an outhouse. The quintessential Vermont town of Weston is less than 4 miles away for dinner and the theater or shopping and a picnic on the green! 7 miles to Magic Mountain, 10 to Okemo, 15 to Bromley, and 20 to Stratton.

Listed by Carrie Mathews of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

32 VT Route 10 Chester VT 05143

MLS Number 4905205

  • Commercial
  • Year Built 1980
  • Square Feet 3,306
  • Acreage 9.4

Outstanding business location! This great 9.4 acre parcel has retail space, walk-in refrigerator and freezer, and a commercial kitchen at ground level, with residential space above for owner/operator or staff! The property is located at the intersection of two state highways - Route 10 and Route 103 which provides excellent access for motorists and tourists. Permitting allows seating for 22. Imagine your local farm to table eatery, a great burger place or maple creamery with activities in the field - perhaps even a 4-wheeler and snowmobile track. This property has amazing possibilities! Bring your passion and imagination when you come see this prime location. Schedule a showing today!

Listed by Suzanne Garvey and Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

289 Fletcher Hill Chester VT 05143

Chester, VT289 Fletcher Hill

Price$375,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4914836

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,848

This beautifully crafted salt- box style home features high ceilings, 3 large bedrooms, 2 bathrooms, spacious living room with Vermont casting stove, all located in a private rural neighborhood making this a great fulltime home or vacation retreat. Close to the welcoming village of Chester and 20 minutes to Okemo Mountain this is ideally situated close to I91 giving you easy access to all Vermont has to offer. Standing seam metal roof, large 2 car garage with direct entry via the newly added breezeway will make for easy living in the winter months. And the private deck off the kitchen is great for cooling off on a hot summer day. Open house is scheduled for Sunday June 12th from Noon to 3PM. Come see this beautiful home.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

312 North Street Chester VT 05143

Chester, VT312 North Street

Price$365,000

Est. Mortgage: $/month

MLS Number 4931626

  • Residential Single Family
  • Bathroom 1
  • Bedrooms 4
  • Square Feet 2,090
  • Construction Existing

This charming Greek revival located within the stone village of Chester, VT, has remained true to it's original in many ways. The yard is small but inviting. A beautiful view, an apple tree, raspberry bushes and white lilacs and a side patio off the kitchen are all yours! There are many closets as well as a larger enclosed area that could be used as a sewing or art room. The back stairway from the master leads you to to the kitchen where you'll find plenty of room, douglas fir flooring and exposed beams. Much of the house has pine flooring and many replacement windows. There is a detached 16x24 studio that's finished space which has electric and heat. Perfect for someone to have a small business or office on site. There is a large attached two bay garage with custom doors as well as another separate one bay detached garage, both with ample storage for cars, ATVs or snowmobiles. Chester is a vital local arts and music community that's close proximity to many VAST trails as well as 30 minutes from several major ski areas. A new propane furnace is being installed 11/21, along with a new water heater.

Listed by Heather Gleim of Walnut Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Grafton Road Chester VT 05143

Chester, VTGrafton Road

Price$360,000

Est. Mortgage: $/month

MLS Number 4903171

  • Land
  • Acreage 142.1
  • 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 142.1 +/- lot is made up of two separate but adjoining parcels, one in Chester comprising of 70.1 acres and 72 acres in Grafton. Each has road frontage on onto route 35 between Chester and Grafton. If you have conservation on your mind both parcels are enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded with small ponds on the Chester lot. There are also a network of logging trails throughout the property. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

3838 Trebo Road Chester VT 05142

Chester, VT3838 Trebo Road

Price$335,000

Est. Mortgage: $/month

MLS Number 4925816

  • Residential Single Family
  • Bedrooms 2
  • Construction Existing
  • Square Feet 1,236
  • Bathroom 2

Ever dreamed of getting away from it all? Here is your chance to own a secluded, mountain home in the woods! It offers the best of all worlds- privately tucked away on nearly 26 acres but only 12 miles to Okemo Mountain and minutes to the quaint town of Chester! The living room is the star of the show for this house with cathedral ceilings, ample picture windows and a large deck for entertaining or just watching the wildlife. There are two bedrooms on the main floor and a bonus lofted room with it's own balcony. The galley kitchen opens to the living room. Large unfinished walkout basement with sliding doors and a bathroom could be finished to provide another living area and has a pellet stove as an additional heating source. Okemo Mountain is less than 20 mins, Stratton and Killington Mountains less than 50 mins, close to VAST trail and less than 5 miles to Chester town center with dining and shopping. 2.5 hours to Boston

Listed by Mandolyn McIntyre of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

788 Farrar Road Chester VT 05143

Chester, VT788 Farrar Road

Price$325,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4922827

  • Residential Single Family
  • Square Feet 1,872
  • Bathroom 3
  • Bedrooms 5
  • Construction Existing

Tucked away in the serene town of Chester VT you will find yourself amongst some of the best views the town has to offer. Located on a dead end road you will find this well taken care of home nestled down the long private driveway. Enjoy the backyards breathtaking mountain views from the three season porch. The open kitchen, dining area and living room offers plenty of sunlight throughout the home. First floor living is achievable with both a bedroom and bathroom on the first level. Blueberry bushes are in the backyard ready to be picked and there is plenty of garden space for more to grow with the partially cleared oversized yard. Your tools and equipment are ready to be placed in the large sheds. Located on a quiet country road but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property is an ideal location to Okemo Mountain Resort (under 10 miles) as well as Magic Mountain (11 miles), Bromley Mountain (20 miles) and Stratton Mountain Resort (24 miles) where you can enjoy skiing and all of Vermonts seasonal activities alternating year round. Schedule your private showing today!

Listed by Taylor Medeiros-Batey of Keller Williams Coastal Realty/ Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

102 Church Street Chester VT 05143

Chester, VT102 Church Street

Price$325,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4927774

  • Residential Single Family
  • Construction Existing
  • Square Feet 1,990
  • Bedrooms 3
  • Bathroom 2

Chester Village Farmhouse with 3+ bedrooms, 2 baths and a welcoming front porch/gathering place! This home is in nice condition inside and out and has had thoughtful upgrades while maintaining the original character of the home. Large living room with connecting dining room creates a nice flow. A lovely sitting area leads to a back entrance and first floor bedroom with private bath with tiled shower which would make a nice primary suite. The functional kitchen has a tiled counter and first floor laundry. The second floor has 2 adjoining bedrooms, a fully renovated tiled bath with electric radiant heat and a study/office that can accommodate guest overflow. Upgrades throughout including roof, most windows, insulation and other utilities. Low maintenance on this charming lot. The .12+/- acres includes a lovely back patio and wrap-around garden with stone wall border. Perfect location close to skiing and recreation and walking distance to Chester Village Green.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

13 Logan Drive Chester VT 05143

Chester, VT13 Logan Drive

Price$299,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4923744

  • Residential Single Family
  • Square Feet 2,426
  • Bedrooms 6
  • Bathroom 3
  • Construction Existing

Beautiful New Englander in the quaint town of Chester, VT! This well-kept home is boasting with bright sunlight and gorgeous gardens ready for you. Five bedrooms, two full baths, two living rooms, an expansive kitchen with cathedral ceiling, large island and gorgeous exposed beams. Attached garage/shop with two bonus rooms above. The property includes apple and pear trees, herbs, perennials, a small horse barn, a patio and beautiful stonework. Finished in-law suite above garage, recent blown-in insulation in walls and attic, new support posts in basement, to name a few of the recent updates. Charming country setting less than 10 minutes from Chester and Springfield. Close to outdoor recreation, skiing, hiking and more.

Listed by Jamie Smith of BH&G - The Masiello Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

441 Markham Mountain Road Andover VT 05143

MLS Number 4931340

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Acreage 10.09
  • Stories 1.5

Looking for a Vermont retreat that everyone in your family will enjoy then look no further!!! This well constructed 4 season camp perched on a 10 acre mountainside parcel offers endless Vermont recreational activities on site and just down the road. There is hiking, biking, sledding, snowshoeing, snowmobiling, and hunting right out the front door, and in just a short drive you have Lowell Lake to kayak, fish, and hike, Stratton Mountain, Okemo Mountain, Bromley Mountain, and Magic Mountain ski resorts, the famous Vermont Country Store to shop and eat, the quintessential towns of Chester and Weston offering farmers markets and music. The property also has an abundance of tranquility and peace. It is located at the END of a town maintained road and borders the backside of a large neighboring parcel and town owned land. The parcel offers mountain views, moonlite and starry nights, an abundance of wildlife, streams, old stonewalls, and snowmobile vast trails located just at the base of the driveway. The parcel has many improvements including a long gravel driveway leading you up to a 28 x 36 camp that is fully insulated, many Andersen and Marvin windows and doors throughout, generator powered, a back bunk room that sleeps 7 or more, a cozy loft to make your own, and lets not forget the covered porch overlooking the ridge line mountain view. Don't miss out on this rare find with many options, keep it a camp, live off the grid, or make it your home.

Listed by Rachel Febbie of Bean Group / Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

441 Markham Mountain Road Andover VT 05143

MLS Number 4931347

  • Land
  • Acreage 10.09
  • Utilities None
  • Zoning residential

Looking for a Vermont retreat that everyone in your family will enjoy then look no further!!! This well constructed 4 season camp perched on a 10 acre mountainside parcel offers endless Vermont recreational activities on site and just down the road. There is hiking, biking, sledding, snowshoeing, snowmobiling, and hunting right out the front door, and in just a short drive you have Lowell Lake to kayak, fish, and hike, Stratton Mountain, Okemo Mountain, Bromley Mountain, and Magic Mountain ski resorts, the famous Vermont Country Store to shop and eat, the quintessential towns of Chester and Weston offering farmers markets and music. The property also has an abundance of tranquility and peace. It is located at the END of a town maintained road and borders the backside of a large neighboring parcel and town owned land. The parcel offers mountain views, moonlite and starry nights, an abundance of wildlife, streams, old stonewalls, and snowmobile vast trails located just at the base of the driveway. The parcel has many improvements including a long gravel driveway leading you up to a 28 x 36 camp that is fully insulated, many Andersen and Marvin windows and doors throughout, generator powered, a back bunk room that sleeps 7 or more, a loft to make your own, and lets not forget the covered porch overlooking the ridge line mountain view. Don't miss out on this rare find with many options, keep it a camp, live off the grid, or make it your home.

Listed by Rachel Febbie of Bean Group / Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

73 Maple Street Chester VT 05143

Chester, VT73 Maple Street

Price$290,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4923373

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Square Feet 2,382
  • Bathroom 2

This pristine Colonial is sure to impress! The home is situated perfectly in one of the best locations in town and only a short walk to The Chester Green. Come inside & find an updated country eat-in kitchen, with a center brick chimney as the focal point. New cabinets, large farmers sink and warm maple floors will welcome you to this fully functional yet great gathering space, where many memories will be made. The formal dining area is perfect for family get togethers and enjoys a large bay window, hardwood floors, and a large pellet stove. The inviting living room is the perfect place to unwind and allows access to the staircase which brings you to the upstairs landing. There you will find the laundry conveniently located around 3 bedrooms. A newly renovated 3/4 bathroom offers ample space and a full glass shower stall. The partially finished barn is the perfect workspace and offers office space along with ample room for extra guests to stay and feel separated from the main living space. The second story of the barn is perfect for dry storage. Relax in your back yard or enjoy no pesky bugs on the large screened-in porch with a lovely view of the well cared for yard. The 2 bay garage and third bay workspace in the barn, as well as triple-pane windows, and Peerless boiler all complete this magnificent village home. Come see for yourself!

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 September 30, 2022 11:54 PM EDT.