Real Estate Management Services Logo

Cummings & Co.

Forging Relationships Throughout Vermont

Chester

339 Richardson Road Chester VT 05143

Chester, VT339 Richardson Road

Price$1,349,000

Est. Mortgage: $/month

Pending

MLS Number 4842176

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 5
  • Square Feet 4,326

This home with over 207 accessible acres in both Chester and Andover is perfect for a large family or group. 9 bedrooms including master suite on first floor, 5 full baths, large public spaces, and an oversized 3 bay heated garage with full finished storage room overhead. Privately set between Chester, Londonderry and Weston with soufthern and western views. Top quality, recent construction and all amenities: granite counters, double ovens, central AC, radiant and baseboard heating, large stone fireplace, full house automatic generator, shining wood floors, and comfortable dining seating for 15-20. Sled, ski or snowmobile through the front yard, meadows or wooded trails. Small pond in view from front porch. The land is enrolled in VT Current Use and VT Land Trust for tax reduction and land conservation. Most house furnishings are included - list available.

Listed by Judy Dickison of Barrett & Valley Associates, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

816 Popple Dungeon Road Chester VT 05143

Chester, VT816 Popple Dungeon Road

Price$850,000

Est. Mortgage: $/month

Active With Contract

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 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

514 First Street Chester VT 05143

Chester, VT514 First Street

Price$379,000

Est. Mortgage: $/month

Pending

MLS Number 4861178

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 3,800

Great location ! exceptional Chester village home on 4.8 acres. Handsome brick home offering 5 bedrooms, 3 baths with wide plank floors, 2 car carriage barn. Large barn with horse stalls and chicken coop. Included across the street 3 acre meadow with river frontage . Nice country feel with village amenities , walk to town green. Included is a 1 bedroom 2 bath apartment with separate entrance and parking spot. All season location, 15 minutes to Okemo ski and golf.

Listed by Frank Ellison and Karen Wilson of Coldwell Banker LIFESTYLES - Ludlow

$
$
%
$/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

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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

3057 Route 11 Chester VT 05143

Chester, VT3057 Route 11

Price$339,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4846044

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,700

This fine 3 bedroom 1 1/2 bath home enjoys southern solar gain, beautiful gardens, stone work and a sweet pond. Reclaim the old hiking trails in the forest behind the house and enjoy the 10 acres of land. The property also includes a large garage that has housed an automotive and auto body business for over 30 years. Not a mechanic? The garage may be perfect for a car collector, woodworker, or artist. Fantastic opportunity for many applications! This versatile property is set midway between Chester and Springfield with easy access to Okemo Mountain Resort, Springfield Hospital and Dartmouth Hitchcock. A great property that offers a multitude of possibilities! Call with your ideas today!

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity

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 August 1, 2021.

 

Skiing In Vermont?

Find Your Mountain Home