Chester VT Real Estate & Homes for Sale

The median home value in Chester, VT is $265,000. This is higher than the county median home value of $198,200. The national median home value is $219,700. The average price of homes sold in Chester, VT is $265,000. Approximately 54.87% of Chester homes are owned, compared to 20.2% rented, while 24.93% are vacant. Chester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chester real estate agent to arrange a tour today!


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Type:
Single Family
Sq.Ft.:
1,214
Status:
NEW LISTING
Beds:
3
Lot size:
1 Acres
Year built:
1890
Baths:
1.00
MLS#:
4855601
Subdivision:
Stone Village

ADDITIONAL INFORMATION

1890's Farmhouse with attached 2-story post & beam barn on 1 acre +/- in the heart of Chester Village. This 3 bedroom, 1 bath home already has a standing seam roof and replacement windows. Now the interior with its high ceilings and generously sized rooms awaits your ideas. Covered front porch and walkout basement with full windows and separate workshop space. Impressive two story barn has 1 garage bay with overhead door. With imagination and creativity, this would make an affordable second home or primary residence. Excellent potential for a home business and en route to Okemo. Short walk to Smitty's Chester Market, a great meat market and small grocery store. Continue down the side walk to the town green to visit the local shopping area, then the town pool/park!

Type:
Single Family
Sq.Ft.:
1,356
Status:
Active
Beds:
3
Lot size:
4.98 Acres
Year built:
1908
Baths:
2.00
MLS#:
4855072

ADDITIONAL INFORMATION

Nestled along the banks of the south branch of the Williams River this classic 1908 home awaits you. Just a mile from the center of Chester this welcoming home will be ideal as a full time family home or vacation getaway. With a new septic system installed in 2019, and open and bright 4.98+/- acre lot with large barn, river frontage and easy access to all Vermont has to offer this property has tremendous potential and charm.

Type:
Single Family
Sq.Ft.:
5,976
Status:
Active
Beds:
12
Lot size:
0.87 Acres
Year built:
1904
Baths:
5.00
MLS#:
4850599

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
3,444
Status:
Active
Beds:
3
Lot size:
0.17 Acres
Year built:
1880
Baths:
4.00
MLS#:
4850594

ADDITIONAL INFORMATION

Very cool property on the Chester Green! 26 The Common has been infused with new energy & exudes a fun vibe helping to revitalize the Chester village. The 1st floor retail space has been incubating as the template of a play-based school and demonstrates how versatile the floor plan can be. With Central air, high ceilings, a pellet stove and a back room that would make a great café/serving space, there is also a 1/2 bath and a full basement with built in storage. A separate entrance, complete with doorbell and air-lock vestibule, leads to the 2nd floor, a totally roomy living space with a double living room that can alternate as a bedroom with closet space and an outdoor balcony. The spacious kitchen w/breakfast bar is open to the laundry area and a 3/4 bath. A dining room/bedroom and a second kitchen w/full bath & laundry hookups could easily be a mother-in-law apt. The third floor has been brilliantly renovated to add 2 more bedrooms and a luxurious bathroom with soaking tub and interesting tiered crown moldings. Each floor has access to exterior decking and stairways: a top deck perfect for growing plants off the 3rd floor bedroom, a covered porch with 2 entrances to the 2nd floor and a lower deck that could easily accommodate a hot tub. A fenced yard is a plus for pets and a detached 2 car garage provides extra storage. The back property line adjoins the town's Cobleigh field- an amazing resource to have in your backyard!

Type:
Single Family
Sq.Ft.:
2,676
Status:
Active
Beds:
4
Lot size:
118 Acres
Year built:
1840
Baths:
4.00
MLS#:
4848206

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
1,344
Status:
Active
Beds:
2
Lot size:
0.33 Acres
Year built:
1860
Baths:
1.00
MLS#:
4846683

ADDITIONAL INFORMATION

Here's your opportunity to live in a sweet Vermont town just minutes from Okemo and short ride to Stratton and Bromley with pastoral views and a short walk to the village market. This 1800's farmhouse is ready for you to bring your ideas and renovate into your dream home. Enclosed sun porch, kitchen has already been demoed and ready to put done as you like. THIS IS A CASH ONLY PURCHASE. LISTING AGENT IS RELATED TO SELLER

Type:
Single Family
Sq.Ft.:
1,700
Status:
Active
Beds:
3
Lot size:
10 Acres
Year built:
1984
Baths:
2.00
MLS#:
4846044

ADDITIONAL INFORMATION

Fantastic opportunity! Although a business is not being sold, this property includes a large garage that has housed an automotive and auto body business for over 30 years. The land also previously supported a used car sales lot. Set above the garage is a fine 3 bedroom 1 1/2 bath home that 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. Not a mechanic? How about car collector, woodworker, or artist? 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!

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
9
Lot size:
0.75 Acres
Year built:
1780
Baths:
9.00
MLS#:
4845016

ADDITIONAL INFORMATION

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. ÂThe main floor is easily accessible with first floor accommodations for those needing to avoid stairs. ÂGracious 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!

Type:
Single Family
Sq.Ft.:
4,326
Status:
Active
Beds:
9
Lot size:
207 Acres
Year built:
2005
Baths:
5.00
MLS#:
4842176

ADDITIONAL INFORMATION

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 game room overhead. Privately set between Chester, Londonderry and Weston with southern 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.

Type:
Single Family
Sq.Ft.:
1,822
Status:
Active
Beds:
3
Lot size:
4 Acres
Year built:
1979
Baths:
3.00
MLS#:
4839272

ADDITIONAL INFORMATION

Rural Living with all the extras. This three bedroom contemporary offers two floors of living space with walk-in first floor entry with 2+ car garage, mudroom, family room with woodstove, den and 3/4 bath. The upgraded main floor offers a bright, functional kitchen with island and wine fridge, open concept to the dining/living area (with access to the large new deck and patio), master bedroom with walk in closet and bath, office, two more bedrooms and a laundry/bath. Screened porch with hot tub, 4+/- acres with woods, garden space, mini apple grove and a shed for storage.

Type:
Single Family
Sq.Ft.:
864
Status:
Active
Beds:
2
Lot size:
0.28 Acres
Year built:
1967
Baths:
1.00
MLS#:
4837679

ADDITIONAL INFORMATION

Single level living with large two bay garage. This house is located an equal distance to Chester and Ludlow via VT RT 103, both offer small town shopping and dining. Ludlow is home to Okemo Mountain Ski Resort and is a short 10 minute drive. Bring your imagination with you when you view this property, the possibilities are endless.

Type:
Mobile Home
Sq.Ft.:
858
Status:
Active
Beds:
2
Lot size:
4.68 Acres
Year built:
1980
Baths:
1.00
MLS#:
4830453

ADDITIONAL INFORMATION

Type:
Single Family
Sq.Ft.:
2,195
Status:
Active
Beds:
3
Lot size:
0.5 Acres
Year built:
1900
Baths:
3.00
MLS#:
4828399

ADDITIONAL INFORMATION

Located in the heart of the village, just a short distance from the historic Chester Green you will find this absolute gem of a home and property. This is a wonderfully cared for 3 bedroom, 3 bathroom family home that boasts refinished hardwood floors and freshly painted rooms. The first floor has a large kitchen with tons of counter space and cabinets as well as a brand new gas range. You'll find a lovely formal dining room with a built in china cabinet. Off the dining room is a den ideal for a home office or study. The living room features and abundance windows facing the front yard that allows for great sunlight all throughout the day. You will also find a full bath and laundry room on the first floor as well as a four season sky lit sunroom off the kitchen that opens out to the back wrap around deck. The second floor features a large primary bedroom with new flooring and its own private bath with walk in closet and a soaking tub. You'll also have fantastic view of the beautiful pastures of neighboring Buttonwood farm. There are two other good sized bedrooms and an additional bathroom rounding out the second floor. All on a level village lot with a classic New England front porch to relax and watch the world go by. Property also boasts a one car garage and a nice private back yard. Conveniently located close to 4 major ski resorts and a short distance to all town amenities. This sweet village home is move in ready and waiting for it's next chapter.

Type:
Mobile Home
Sq.Ft.:
924
Status:
Active
Beds:
2
Lot size:
5 Acres
Year built:
1996
Baths:
1.00
MLS#:
4827417

ADDITIONAL INFORMATION

This picturesque lot commands a stunning view from its lofty perch overlooking Stage Road in Chester. The lotÂis a mix of open field and forest. This would be perfect for your new dream home, gentleman's farm or simply a great getaway location. This location has so much potential for expansion and will be easily developable. Just insert your imagination.

Type:
Mobile Home
Sq.Ft.:
952
Status:
Active
Beds:
1
Lot size:
3.78 Acres
Year built:
1987
Baths:
1.00
MLS#:
4826249

ADDITIONAL INFORMATION

This is a fantastic location just minutes to the Village of Chester. This lot and the adjacent lot, which is also available, are separated by a lovely pond making this a wonderful location for a family compound. These are also ideal sites to build your dream house and have an investment property right next door!ÂSee MLS 4826247

Type:
Mobile Home
Sq.Ft.:
952
Status:
Active
Beds:
2
Lot size:
3.83 Acres
Year built:
1995
Baths:
2.00
MLS#:
4826247

ADDITIONAL INFORMATION

This is a fantastic location just minutes to the Village of Chester. This lot and the adjacent one, which is also available, are separated by a lovely pond making this a wonderful location for a family compound. These are also ideal sites to build your dream house and have an investment property right next door!ÂSee MLS 4826249

Type:
Single Family
Sq.Ft.:
5,546
Status:
Active
Beds:
5
Lot size:
1 Acres
Year built:
1850
Baths:
7.00
MLS#:
4822226

ADDITIONAL INFORMATION

This is one of a kind! Whether you are looking for a home for your family and guests, or something you can use for a home business, this one is for you. It isn't often you find a house in this condition - just look at that porch. Located just a short distance to the village green, shops and eateries. In the other direction you will find the Chester recreation area for pool, tennis, and hiking. You have your choice of ski mountains with Okemo, Magic, Bromley and Stratton all a short drive away... golf, fishing, hiking, biking and so much more that Vermont has to offer. The home is lovely. There is a large kitchen, dining room and living room for formal relaxation. An office and first floor bedroom and full bath, too. Upstairs are 4 more bedrooms and 3 more baths. There is a back staircase off the kitchen. The back end of the house is where fun can happen. There is a bar and sitting area along with two rec rooms, currently with ping-pong, air hockey, billiards and poker tables! In addition, there is a large multipurpose room... exercise, shop, studio, rental space.... you decide! The fiber optic internet means you can stay in touch with work or take in your favorite movies. The landscaping is very attractive. Off the back of the house, there is a private deck that overlooks the huge, flat back yard. Every inch of it is usable for play or gardens! There is much to love here and in Chester. Offered mostly furnished. Be sure to take in the video to see all there is to offer.

Type:
Single Family
Sq.Ft.:
6,848
Status:
Active
Beds:
10
Lot size:
5.63 Acres
Year built:
1810
Baths:
12.00
MLS#:
4820671

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
7,610
Status:
Active
Beds:
2
Lot size:
3.5 Acres
Year built:
1997
Baths:
4.00
MLS#:
4818070

ADDITIONAL INFORMATION

Built and operated as a successful retail/eat-in bakery/cafe for 20 years, this fascinating structure on 3.5+/- level acres offers possibility for use as a full time residence with a home business, or, with further modification, a unique and spectacular full time home. The amazing cathedral like structure was built in 1997 on an old homestead and attached to the barn which dates back to 1850s. The entire interior is connected and finished as one seamless space. There is a 4-flu chimney which could be made into a beautiful stone fireplace. The open floor plan could be redesigned for living space. The possibilities are endless. 4 bathroom spaces are in place with two half baths to code for public use and two more bath areas with a walk-in tiled shower. A home business such as a dance studio, music space, or any form of retail business would work very well with flexible options as to where the business entrance would be. Walking distance to town, adjoins town rec area.

Type:
Single Family
Sq.Ft.:
2,688
Status:
Active
Beds:
2
Lot size:
2.22 Acres
Year built:
1973
Baths:
2.00
MLS#:
4766090

ADDITIONAL INFORMATION

A swan in the making!! Business..Residential Opportunity! This 2 story property features large partially renovated 1st floor retail space with a large 2 bedroom apartment on the 2nd floor. Enjoy 2.22 +/- acres with easy in and out access. A great "owner occupied" business or investment property. Act 250 permitted for retail and/or deli with exposure on Route 103 South in Chester. Approved for 10 parking spaces. A 3/4 bath is on the first floor for the business space. Additional features include, full basement, new furnace, baseboard heat, flexible floor plan with high ceilings, hardwired smoke and CO detectors. This property has so much potential! Put in some work and bring it's activity back! It's ready!

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Andrea D. Conner, License 71221, Xome Inc., License 68390, AndreaD.Conner@xome.com, 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


The data relating to real estate displayed 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, This information is deemed reliable, but not guaranteed. Copyright 2021 New England Real Estate Network, Inc. All rights reserved.

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