Chester VT Real Estate & Homes for Sale

The median home value in Chester, VT is $192,100. This is lower than the county median home value of $200,500. The national median home value is $185,800. The average price of homes sold in Chester, VT is $192,100. Approximately 56.28% of Chester homes are owned, compared to 23.92% rented, while 19.8% 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.:
4,044
Status:
Active
Beds:
4
Lot size:
79.5 Acres
Year built:
1967
Baths:
5.00
MLS#:
4793511

ADDITIONAL INFORMATION

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 Vermont best ski areas which creates 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 with a sugarbush and 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.

Type:
Single Family
Sq.Ft.:
2,071
Status:
Active
Beds:
2
Lot size:
43.8 Acres
Year built:
2001
Baths:
2.00
MLS#:
4790047

ADDITIONAL INFORMATION

Privately sited among trees and open fields on 43.7 acres, this 2001 cape style home abuts 1,000âs of acres of forest. The house features two bedrooms (town records say 3 bedrooms), 2 baths, a fireplace, farmers porch overlooking the field, and an open deck off the back of the house. There is a two-car attached garage. The driveway runs along a 3-acre field to a second field where the house is located. Much of the property is forested with sugar maple, red oak, white pine and hemlock.

Type:
Single Family
Sq.Ft.:
440
Status:
Active
Beds:
1
Lot size:
0.25 Acres
Year built:
1987
Baths:
MLS#:
4789868

ADDITIONAL INFORMATION

A Glamper's dream property!! Charming, furnished 1 bedroom with sleeping loft, efficiency galley kitchen, living room and an outhouse built to state specs with elec. and heat on .25+\~ acres in prime hunting, skiing, snowmobiling, recreation area. Town maintained road, newly re~built wall furnace, covered porch and a brand new deck. The lot is open and the cabin is close to the road for easy access. There is a nice yard with stone walls and borrowed landscaping beyond. A great way to be close to skiing for those who don't mind roughing it a little. Half mile to snowmobile trail..

Type:
Single Family
Sq.Ft.:
670
Status:
Active
Beds:
1
Lot size:
30.5 Acres
Year built:
1978
Baths:
1.00
MLS#:
4786918

ADDITIONAL INFORMATION

Country Cabin in Chester with 30.5+/-acres. Is easily accessible off a town maintained road. This Log Home is a great opportunity to own a large Parcel of Land (in current use) to self sustain with mostly wooded acreage and a couple open acres for gardening or yard. A tidy home with screened porch, front deck and cozy interior with kitchen/dining area, bedroom 3/4 bath, livingroom with woodstove. Basement for additional storage.

Type:
Single Family
Sq.Ft.:
1,500
Status:
Active
Beds:
4
Lot size:
76.23 Acres
Year built:
1955
Baths:
2.00
MLS#:
4785615

ADDITIONAL INFORMATION

What was once a bustling campground known as Hidden Valley Campground to many locals, can now be your next investment or forever home! This 73+ acre lot with 4 bedroom, 2 bath home with attached 2 car garage is just the start! The property is also home to a 33 camp sites with power and water, a hidden cottage, full 4 unit bath house, lean-to and 2 ponds as well as a large gravel pit. The road frontage boasts a lovely pond on Mattson Road and another hidden swimming pond located behind the campground which is equipped with a dock. A septic permit for the two 1500 gallon septic tanks is already in place for the camping area. One potential idea is a Tiny house community with the right permitting! The land could be used for just about anything with 73+ acres for hunting, fishing, and enjoying all VT has to offer! The possibilities are endless for this great place that is so rich in history from the original Mattson family. Come explore!

Type:
Single Family
Sq.Ft.:
2,176
Status:
Active
Beds:
3
Lot size:
6.4 Acres
Year built:
2008
Baths:
3.00
MLS#:
4776357

ADDITIONAL INFORMATION

This impeccable property offers comfortable living with luxury finishes. Appreciate cooking in the beautiful open concept kitchen which is fully equipped with a Wolf five-burner downdraft cooktop, Wolf wall oven, granite countertops and custom hickory cabinets. Relax in the light filled living room which boasts vaulted ceilings, cherry beams and an energy efficient Gnome Pellet Stove. Take in the sunset from the marvelous three season insulated sun-room. The spacious master suite offers an oversized bathroom with his and her sinks and closets, a tiled walk-in shower, and granite countertops. There is ample parking and storage in the attached oversized two car garage. There is radiant heat throughout the kitchen, master bathroom and finished lower level. The two stall horse barn, with hayloft and tack room, is perfect for horse lovers and could be transitioned into four-stalls if needed. Take advantage of low energy costs with the Geothermal heating and cooling system. Enjoy privacy and convenience with this Lovers Lane property - just 5 minutes from the charming center of Chester and only 10 miles from Interstate 91.

Type:
Single Family
Sq.Ft.:
1,684
Status:
Active
Beds:
3
Lot size:
1.1 Acres
Year built:
1880
Baths:
2.00
MLS#:
4776191

ADDITIONAL INFORMATION

Classic old farmhouse in a very convenient location midway between Ludlow, Chester and Springfield. Three good sized bedrooms, 1.5 baths. Large barn/shed. Good commercial potential with plenty of visibility.

Type:
Single Family
Sq.Ft.:
5,482
Status:
Active
Beds:
9
Lot size:
10.25 Acres
Year built:
1861
Baths:
7.00
MLS#:
4776152

ADDITIONAL INFORMATION

Are you ready to live the ultimate dream of running your own business in Vermont? Once featured in Country Inns of New England this property could be yours! Current owner once operated a successful 24 seat restaurant that includes commercial kitchen, 6 nicely appointed rooms for guests (plus two additional rooms) and owner's quarters. What do you want to do? inn, bed and breakfast, retreat, events...you name it! Located conveniently to I91, Okemo Mountain (only a few minutes drive), several other ski resorts, the shopping in Manchester and villages of Chester, Weston and Cavendish you could not ask for a better spot to live and work in Southern Vermont. There is much to love about this antique farmhouse from the ornate woodwork to the hardwood floors this property feels like home. The barn offers a multitude of possibilities (woodworking shop, dance space, yoga space, events). The outdoor space speaks to country living with gardens, pond and level yard.

Type:
Single Family
Sq.Ft.:
2,296
Status:
Active
Beds:
3
Lot size:
2 Acres
Year built:
1780
Baths:
2.00
MLS#:
4775710

ADDITIONAL INFORMATION

Located on a long country road in the town of Chester is an antique cape well worth visiting. Perched just right on 2 acres, it offers a private rear yard and easy access to the village. This substantial home has spacious rooms including master on the main level, wide pine floors, updated bathroom and four bedrooms! A great workshop as well as a country covered porch and an incredible location all complete this property. Come and see what country living, yet a short drive to town, is all about!

Type:
Single Family
Sq.Ft.:
420
Status:
Active
Beds:
2
Lot size:
3 Acres
Year built:
1965
Baths:
1.00
MLS#:
4775255

ADDITIONAL INFORMATION

Here is your chance to have an inexpensive get- a- way. This mobile home could be fixed up and livable for a family of second home. You may want to use it as headquarters while you build. SKIERS AND SNOW MOBILERS TAKE NOTE: VAST TRAIL ACCESS. MINUTES TO OKEMO MOUNTAIN, AS WELL AS THREE OTHER NEARBY MAJOR SKI AREAS The woods are filtered with sunlight and could afford a nice quiet off road building site. Note the babbling brook across the way. There is a babbling brook across the way. Wymans Falls Road is dead end.

Type:
Single Family
Sq.Ft.:
2,967
Status:
Active
Beds:
5
Lot size:
10.19 Acres
Year built:
1880
Baths:
3.00
MLS#:
4773386

ADDITIONAL INFORMATION

This exquisite Vermont farmhouse property has under gone many changes and updates throughout the years. In excellent overall condition the home offers 5 bedrooms including a first floor master with bath and 4 good sized bedrooms on the second floor. Large country kitchen with 2 sinks, island and ample counter space is situated as the hub of the first floor. Living room features vaulted wood ceilings and gorgeous stone fireplace. Off the living room is bright and sunny reading area and casual eating space off the kitchen. You also have a formal dining room off the other side of the kitchen. Full bath, laundry room, mudroom great for ski storage and a screened in porch round out the home. The property features a large pool house with heated pool and hot tub for year round swimming and enjoyment. The 2,000 sq ft dairy barn is currently used as a 3 bay garage. It can be easily updated to accommodate horses or other animals. The 16.1 acres includes a separate 5.9 acre lot with frontage on Jillie lane that has its own waste water permit. Lot can be built on, sold separately or kept for privacy. The property has nice views, pond and some beautiful stonework and walls. With the tasteful character and a classic Vermont setting this could be the property you've been looking for. Centrally located near town, Rt 91 and several major ski areas.

Type:
Single Family
Sq.Ft.:
1,008
Status:
Active
Beds:
2
Lot size:
4.1 Acres
Year built:
1800
Baths:
1.00
MLS#:
4771039

ADDITIONAL INFORMATION

A good start. This classic cape style farmhouse offers a back porch, 2-3 bedrooms, eat-in kitchen, living room and a 3/4 bath. Located on a State Road the property has easy access. A bright and sunny location with barn and 4+/- acres offering a great opportunity for extensive gardens, lawn or pasture.

Type:
Single Family
Sq.Ft.:
1,176
Status:
Active
Beds:
3
Lot size:
2 Acres
Year built:
1977
Baths:
1.00
MLS#:
4770367

ADDITIONAL INFORMATION

Charming Chalet built in 1977 on 2 Acres with a babbling brook in back. Standing Seam Roof, bulk Head to Basement. Wrap around deck. Walk off deck into the entrance where the washer and dryer and coat closet are. Kitchen with plenty of counter space and cupboards. Dining area, Living Room with wood stove. 3 Bedrooms on main level and open bedroom with 4 beds on second floor. Master Bedroom has slider onto the deck. Full Bath. Dry basement, 200 Amp Box, Forced warm air heat. Hot water heater and Fiber optic. Artesian well and 1000 gal septic. Perfect for a second home as it is close to Okemo Ski Area, Crown Point Gulf Course and Snow Mobile Trails. 5 miles to Springfield Hospital and Medical Center. Near I-91 Exit 7.

Type:
Single Family
Sq.Ft.:
1,365
Status:
Active
Beds:
3
Lot size:
0.25 Acres
Year built:
1890
Baths:
2.00
MLS#:
4767332

ADDITIONAL INFORMATION

Price Reduced!! This property must be seen!! Stylishly remodeled 3 bedroom, 2 bath 1890`s farmhouse on .25 +/- acres in prime Chester village location. Fabulous newly designed kitchen with center island featuring beautiful, original hardwood maple flooring, stainless steel appliances, custom wood counter tops, recessed lighting, pantry closet- a great space to cook!! A large laundry/mudroom room adjoins the kitchen for convenience with separate entrance. The beautiful resurfaced large living room with period archway opens to a new deck where you can enjoy the shaded yard overlooking the brook. A full bathroom has been added to the first floor. Upstairs there are 3 bedrooms and a new 3/4 bath with walk-in tiled shower. Handsome refinished hardwood and softwood original flooring throughout most of the house. The full basement has been spray foamed and protected by a vapor barrier for energy efficiency. Original windows have all been cleaned, repainted and are operational. The yard has been enhanced by a wrought iron style fence and a paved parking pad is large enough for 2+ cars. So many subtle finishing details have been added to make this a special property!!!

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

Retail Opportunity! Awesome 2 story property featuring large retail space with large 2 bedroom apartment on 2.22 +/- acres. Great for either owner occupied business or investment property. Act 250 vetted for retail and/or deli, the property offers great exposure on Route 103 South in Chester and has been approved for 10 parking spaces. There is an additional 3/4 bath on the first floor for the business space. Other features include, full basement, new furnace, baseboard heat, flexible floor plan with high ceilings, hardwired smoke and co2 detectors. Whether you are looking for an investment or owner occupied business this property has much potential!

Type:
Single Family
Sq.Ft.:
4,866
Status:
Active
Beds:
4
Lot size:
158 Acres
Year built:
1860
Baths:
5.00
MLS#:
4763930

ADDITIONAL INFORMATION

Four season retreat with VAST Trail access and great skiing close by. This 158 acre estate provides all you would want in a VT country farm/wilderness property. Sited within itâs own three hilltops and at the end of a town maintained road, there is ultimate privacy. You will find open fields, wooded trails, a swimming pond and beaver ponds, a former soapstone quarry hidden within one of the peaks, a Morton Barn full of equipment and off road vehicles...even a dirt track to test your riding skills! The bldgs include a circa 1780 barn, an 1860 cape and a 1970âs addition. The barn is being re-done as a grand finished space. All of the original beams are exposed. It will be a perfect studio, family room or game room upon completion. MUST be seen! The owner has also done extensive renovations to the residence to increase energy efficiency and to merge the older charm with modern improvements. The cape wing of the residence has a stunning state of the art kitchen, an open dining area, a gracious living room with re-worked original floors and a second floor master bedroom. The 1970âs addition has been re-worked to enhance the bedroom spaces and the overall flow. A 2nd floor great-room boasts a massive fireplace and a great wrap-around deck to take in the beautiful views of your 158 ac acre estate. This property has been the dream project of its retired owner and this 5 year plan is coming to an end. This turnkey property awaits its next steward! Additional +/- 234 acres available.

Type:
Single Family
Sq.Ft.:
4,234
Status:
Active
Beds:
3
Lot size:
11.19 Acres
Year built:
2002
Baths:
3.00
MLS#:
4762698

ADDITIONAL INFORMATION

If you're looking for a beautiful home with lots of room, long range views from a wrap around porch with expansive deck, granite counter-tops, and room to expand...then look no further. This home boasts over 4200 square feet of living space and a separate 30â x 40â heated workshop/studio with its own bath and laundry hook ups. High ceiling basement in main house with walk out slider adds to the expansion possibilities. A radiant heating system with Munchkin high efficiency boiler coupled with a whole house Lifebreath air handler and insulated concrete foundation makes this an efficient and cost effective home to maintain. Hardwood and tile floors in the common areas adds to the beauty of this spacious home. Enjoy the huge game room that currently houses a pool table, foosball table, and ping pong table. Owner recently replace the roof, sheet rocked the garage, resurfaced driveway, and painted the deck and porch. This home is ready for the next owner to enjoy for years to come.

Type:
Single Family
Sq.Ft.:
3,445
Status:
Active
Beds:
4
Lot size:
26.4 Acres
Year built:
1989
Baths:
4.00
MLS#:
4762267

ADDITIONAL INFORMATION

Come fall in love! Just 3.5 miles from the green in Chester, is this stunning farmhouse built in 1989. A superb country location. The land is split onto both sides of the road providing permanent protection. Across the road from the house is a large, flat field that is perfect for horses. Over 1,300 feet of frontage along the South Branch of the Williams River. On the house side of the road, you will find multiple outbuildings & barns. Sheep & horses are currently at home here. Gardens, sheds, & a car barn with a huge studio above awaits craftspeople, writers, woodworkers, or exercise enthusiasts. Saving the best for last, the home is just stunning. Covered porches for quiet time. Enter through the front door to large foyer & hall. To the left is a formal parlor, & to the right, a large country kitchen with sitting room. The kitchen is every chef's dream from the appliances to the tile work. The dining room has a wall of windows overlooking the gardens & pasture. A mudroom & first-floor bedroom with bath & walk-in closet round out the first floor. Upstairs are three very generous bedrooms & two baths. The custom features throughout the home are fantastic -- tile work, painting, trim detail & more. The full, dry basement has loads of space. There is fiber optic internet, a generator, wood boiler, along with a traditional multi-zone oil boiler. This is a spot to call home for horse people, home business owners, artisans, families or retirees. Wait until you see it for yourself!

Type:
Single Family
Sq.Ft.:
4,912
Status:
Active
Beds:
4
Lot size:
60 Acres
Year built:
1978
Baths:
5.00
MLS#:
4757103

ADDITIONAL INFORMATION

Right outside the Village of Chester tucked away on a hillside, is this tastefully updated contemporary home. Terrific southern views. Totally private. With great separation of space, you will want to invite all your friends. There are four bedrooms each with their own bath including separate guest quarters with a private entrance. Delight in preparing a meal in the brand new kitchen. Dine in front of the stone fireplace. Sip a cocktail in the cozy living room. Snowshoe or mountain bike on the nearby trails. Kick your shoes off in the new slate mudroom. Relax on the outdoor patio in the summertime. So much to enjoy throughout all four seasons in Southern Vermont - close to golf and skiing at nearby Okemo Mountain Resort. This property is enrolled in Vermont's Current Use Plan to manage the forestry and generate tax benefits with additional acreage available for those who seek more land. A perfect Vermont retreat!

Type:
Single Family
Sq.Ft.:
2,176
Status:
Active
Beds:
3
Lot size:
11.01 Acres
Year built:
2008
Baths:
3.00
MLS#:
4752797

ADDITIONAL INFORMATION

This impeccable property offers comfortable living with luxury finishes. Appreciate cooking in the beautiful open concept kitchen which is fully equipped with a Wolf five-burner downdraft cooktop, Wolf wall oven, granite countertops and custom hickory cabinets. Relax in the light filled living room which boasts vaulted ceilings, cherry beams and an energy efficient Gnome Pellet Stove. Take in the sunset from the marvelous three season insulated sun-room. The spacious master suite offers an oversized bathroom with his and her sinks and closets, a tiled walk-in shower, and granite countertops. There is ample parking and storage in the attached oversized two car garage. There is radiant heat throughout the kitchen, master bathroom and finished lower level. The two stall horse barn, with hayloft and tack room, is perfect for horse lovers and could be transitioned into four-stalls if needed. Take advantage of low energy costs with the Geothermal heating and cooling system. Enjoy privacy and convenience with this Lovers Lane property - just 5 minutes from the charming center of Chester and only 10 miles from Interstate 91.

Type:
Single Family
Sq.Ft.:
3,516
Status:
Active
Beds:
3
Lot size:
10 Acres
Year built:
1998
Baths:
4.00
MLS#:
4748048

ADDITIONAL INFORMATION

Beautiful country estate in village setting. Welcome to 101 Stonehedge â located just above the historic Stone Village in the quaint town of Chester. You will be met with a beautiful stone walled entrance and a hedge lined drive. An oversized 3 car garage has plenty of room for your vehicles as well as room to expand above. The atrium welcomes you into the home that is bright with sun filled rooms and quality finishes throughout. The 2 story living room has a fireplace, discreet wet bar, and 2 sets of French doors that lead out to a large deck. A second living space and game room provides ample room for entertaining year-round. The first floor master bedroom wing also has French doors to the deck, a den, walk in closet, and well appointed bathroom. Views of Flamstead Mountain can be seen from most rooms, the deck, and the well designed, easy care, perennial gardens. Nice sprawling grounds with ornamental trees, an arbor, brick pathways and even a chicken coop make this a perfect private retreat. Being centrally located allows ease of access to several ski areas, lakes, hiking, biking, and shopping. Come see what this home has to offer.

Type:
Single Family
Sq.Ft.:
2,031
Status:
Active
Beds:
3
Lot size:
1.08 Acres
Year built:
1956
Baths:
3.00
MLS#:
4744957

ADDITIONAL INFORMATION

Perched on its 1 acre with lots of sunshine, this 3 bedroom home offers the convenience of Village lifestyle. One level living with wheel chair accessible elevator to a lower level garage and basement storage. Living and dining areas both with large windows and wood burning fireplaces. A sun room porch just off the remodeled kitchen. The large master suite has a gas stove for warmth and a handicap accessible bathroom. 2nd bedroom with a 1/4 bath and a 3rd bedroom with wonderful built-in shelves and desk that can also be used as a study. A landscaped yard with fruit trees, stone walls and a frog pond finish off this great home.

Type:
Single Family
Sq.Ft.:
4,328
Status:
Active
Beds:
3
Lot size:
0.52 Acres
Year built:
1870
Baths:
5.00
MLS#:
4744482

ADDITIONAL INFORMATION

This unique and beautiful property is ready to become your new home or perhaps a new business location. Located on the Main Street of picturesque Chester village the former Rectory has beautiful woodwork throughout as well as lovely french doors, fireplace and numerous built-ins. This home features two living rooms, the dining room with built-ins, an eat-in kitchen with a butler's pantry, three bedrooms as well as a den or office. The bonus room, formerly the Chapel, is open to numerous possibilities. A full basement and attic space and sitting on a newly sub-divided lot of .53 acre the property includes a detached garage and lovely wrap around porch.

Type:
Single Family
Sq.Ft.:
4,424
Status:
Active
Beds:
7
Lot size:
0.6 Acres
Year built:
1820
Baths:
8.00
MLS#:
4721840

ADDITIONAL INFORMATION

Built in Circa 1820 Victorian Inn is rich with history and located in the heart of Chester Village. Property offers an operating Inn with a gift shoppe, a beautiful Carriage House, flower gardens, chicken coop and peaceful lawn area separating a private cottage at the rear of the property. The Inn has beautiful details and many of its original features . Exquisite woodwork and large windows that allow for natural light. Offering six en-suite bedrooms and a small apartment space just above the gift shoppe. The common spaces include a dining area with a bay window, a cozy den with a gas fireplace and a gracious living room. The detached two-story Carriage House once offered home for horses and has a garage space for one vehicle. Both the Inn and Carriage House are registered on the National Historic Registry. The three bedroom cottage is full of character and offers privacy. Perfect for an owner, inn keeper quarters or an additional rental property. This property is a true gem with so many possibilities.

Type:
Single Family
Sq.Ft.:
640
Status:
Active
Beds:
2
Lot size:
2.5 Acres
Year built:
1952
Baths:
1.00
MLS#:
4704686

ADDITIONAL INFORMATION

PRICE REDUCTION: If you are looking for a Handy man's Special, that is ideally located in close proximity to fishing, golfing, kayaking, skiing & snowmobiling, then this may be the home & property for you. The sale includes the handy mans special home, plus a two bedroom mobile home with drilled well & septic system. Additionally, there are two dug wells & two additional septic systems, all on 2.5 acres. One could live in the mobile home, while rehabbing the existing framed home. If this sounds right for you, then schedule a time today to explore the possibilities.

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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 2020 New England Real Estate Network, Inc. All rights reserved.

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