Chester VT Homes for Sale

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Type:
Single Family
Sq.Ft.:
2,220
Status:
NEW LISTING
Beds:
4
Lot size:
0.2 Acres
Year built:
1860
Baths:
2.00
MLS#:
5027669

ADDITIONAL INFORMATION

This beautifully renovated farmhouse offers a perfect mix of classic charm and modern updates, located just a short distance from the historic town green, shopping, and dining. The home features a spacious living room and cozy family room, providing plenty of space for both relaxation and entertainment. A dining area off the modern kitchen is perfect for family meals or hosting guests. The wood stove in the kitchen provides warmth and ambience The main floor also includes a convenient first-floor bedroom, while the second level features three additional bedrooms, one of which is an excellent option for a home office. You'll also find a large laundry room and a second floor back porch providing access down. Recent updates include new hardwood floors, fresh interior paint, and updated bathrooms. Mini-split systems on both floors provide efficient air conditioning and additional heating for year-round comfort. Enjoy outdoor living with a private fenced in back courtyard, a back porch entry, and a fenced-in backyard. A 1-car garage barn adds extra storage. This home is a dream for outdoor enthusiasts, with major ski resorts including Okemo, Magic, Bromley, and Stratton just a short drive away. The town Recreation Center, pool, and VAST snowmobile trails offer year-round fun, with plenty of biking and hiking trails only a half mile away. Vermont living at its finestâ??right in town!

Type:
Single Family
Sq.Ft.:
1,005
Status:
Active
Beds:
2
Lot size:
2.2 Acres
Year built:
1988
Baths:
1.00
MLS#:
5025768

ADDITIONAL INFORMATION

Escape to this charming log cabin, tucked away on a quiet dead-end road. With an attached two-car garage and a small horse barn, this property is perfect for those seeking a blend of rustic charm and practicality. Inside, youâ??ll find a thoughtfully designed two-bedroom, one-bathroom layout with an airy open floor plan. The kitchen and living room flow seamlessly together, centered around a wood stove that creates a warm and inviting atmosphere during the winter months. The main living area features classic wide board pine flooring, while the bedrooms boast updated vinyl plank floors for a modern touch. A spacious entryway doubles as a den, providing versatility to suit your lifestyle. The full basement includes a finished bonus room for additional living space and offers potential for further expansion. Step outside to enjoy summer evenings on the covered front porch. This peaceful retreat is just minutes from Chesterâ??s charming village center, where youâ??ll find dining and shopping options. Plus, itâ??s a short drive to Okemo Mountain for year-round recreation. Whether youâ??re looking for a cozy home or a weekend getaway, this property has it all! Donâ??t miss your chance to own this log cabin in an ideal location within close proximity to ski mountains, lakes, shopping, and dining! Visit the Okemo real estate community today. Taxes are based on current town assessment.

Type:
Single Family
Sq.Ft.:
3,888
Status:
Active
Beds:
4
Lot size:
0.53 Acres
Year built:
1870
Baths:
5.00
MLS#:
5024631

ADDITIONAL INFORMATION

This spacious 1800's home is filled with Vermont charm and located in the heart of Chester. Filled with natural light from newly installed windows, the home boasts beautiful wood floors throughout and antique door handles that capture the essence of the era. Spacious bedrooms provide ample comfort, while smart thermostats ensure modern convenience. A newly built, covered front porch welcomes you into the home, and a deck off the kitchen leads to an open, level backyardâ??perfect for gardening or outdoor activities. One of the standout features of this property is the versatile studio space. Accessible via its own entrance from Main Street, this expansive area features vaulted ceilings and two half baths, offering endless possibilities. Whether you're looking to create a storefront, set up an at-home business, or convert the space into a private apartment, the potential is limitless. This property offers a unique opportunity to live in a quintessential Vermont town while having the flexibility to tailor the space to your needs. It's a must-see for anyone seeking a charming, functional home with potential for growth!

Type:
Single Family
Sq.Ft.:
1,304
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
1890
Baths:
2.00
MLS#:
5024539

ADDITIONAL INFORMATION

Step into the charm of yesteryear with all the comforts of today at 663 Depot Street. This completely renovated 3-bedroom, 2-bathroom home combines historic character with modern convenience. Since 2022, everything from the insulation, drywall, electrical, plumbing, & HVAC has been updated, including a new furnace, water heater, fixtures, countertops, cabinets & appliances. The only original feature left untouched is the flooring- beautifully refinished original wood. The owners thoughtfully chose period-appropriate paint colors & preserved unique touches like exposed beams & original woodwork. You'll love the Victorian martini pedestal sink in the upper bathroom! There is also a 2-story attached post-and-beam barnâ??larger than the house itselfâ??with a powered overhead door. Keep it as a garage or workshop, or explore the incredible potential to double your livable space by finishing it. Sited on 1 acre, the property has a sprawling lawn, fire pit for evenings under the stars & an unbeatable location near Chester's Stone Village, Grist Mill, Smitty's Market, & other local amenities. Just 15 min to Okemo Mtn & the lakes, 30 min to Bromley, & under an hr to Killington, Stratton, & Mt Snowâ??a prime spot for skiing, hiking, & year-round fun. Currently used as both a family getaway & a successful Airbnb, this property has serious income potential for those looking to maximize its use. Whether youâ??re searching for a primary home or an investment, this timeless home is not one to miss.

Type:
Single Family
Sq.Ft.:
1,990
Status:
Active
Beds:
4
Lot size:
0.12 Acres
Year built:
1895
Baths:
2.00
MLS#:
5024148

ADDITIONAL INFORMATION

A classic, easy maintenance four bedroom, two bath home in Chester village on .12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and elegant lighting, a country kitchen with marble tile flooring, first floor bath with tiled shower and an adjoining bedroom with a lovely reading/entertainment nook that connects with the dining room. The second floor has a large landing with two adjoining bedrooms, a full bath with radiant heat in the floor and a cool, private back bedroom. The basement has foam insulation and the windows, water heater and oil tank have been replaced. Ready for your enjoyment as primary, secondary or investment property. Close to Magic, Okemo, Bromley and Stratton Resorts, and year year-round recreational activities.

Type:
Single Family
Sq.Ft.:
2,960
Status:
Active
Beds:
3
Lot size:
0.7 Acres
Year built:
1844
Baths:
3.00
MLS#:
5023780

ADDITIONAL INFORMATION

The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village.

Type:
Single Family
Sq.Ft.:
2,941
Status:
Active
Beds:
3
Lot size:
53.16 Acres
Year built:
2008
Baths:
4.00
MLS#:
5017587

ADDITIONAL INFORMATION

Chase Brook Farm is at the end of a quiet country road, offering complete privacy on 53 acres and yet just 10 miles from Okemo Ski Resort, fine dining, and shopping. The views are punctuated by bucolic vistas of the Green Mtns including Steadman Hill, the highest peak in Chester. At the center of this property is a 2,941 s.f. farmhouse, built in 2008 and inspired by countless visits to Sturbridge Village. Thoughtfully designed to evoke the charm of a historic home, it features hand-planed boards, painted wide pine floors, wrought iron latches, and soapstone countertops while providing the comfort of modern amenities, including new mechanicals, updated wiring, and a large, dry basement. This property invites year-round enjoyment. In winter, sled down hills out back, or clear the pond for skating parties. Snowmobilers, skiers, and snowshoers will appreciate the room to roam and easy access to the VAST trail. After a day in the snow, warm up by one of the two cozy fireplaces or take a soak in the hot tub. In summer, enjoy a swim or cast a line in the stocked pond, or gather berries from the 80+ blueberry bushes and raspberry patch. The fall season brings apple picking and the land is suitable for livestock, offering versatility for a variety of uses. Chase Brook weaves in and out along the border to the East. Additional features include an attached 1-bay garage, a 3-bedroom caretakerâ??s house with a 3-bay garage, and fiber optic internet. Showings begin October 11.

Type:
Single Family
Sq.Ft.:
1,800
Status:
Active
Beds:
3
Lot size:
10.08 Acres
Year built:
1984
Baths:
2.00
MLS#:
5005884

ADDITIONAL INFORMATION

Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high ceilings and huge amount of work space will be appreciated. Set back from the road with plenty of parking area, there is room to add more outbuildings for business needs. The efficient house features a cozy living room, first floor bedroom, full bath and kitchen/dining that opens to the back deck overlooking the private pond. The second floor has a large common area adjoined by two bedrooms and a half bath with laundry. The whole house generator and Fiber Optic internet service will keep your systems and business running during power outages. Commutable to the Upper Valley, convenient to Springfield, skiing, shopping, Chester Village and all the area has to offer.

Type:
Single Family
Sq.Ft.:
3,779
Status:
Active
Beds:
4
Lot size:
193 Acres
Year built:
1972
Baths:
4.00
MLS#:
5002063

ADDITIONAL INFORMATION

Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside a wide-open main living area and great room overlooks the 10 foot deep swimming pond, and the nearby stream can be heard from the deck or kitchen with the windows open. Step into the luxurious primary suite, a sanctuary with large windows and a spa inspired bath with a free-standing tub that boasts one of the best views from the house. Enjoy the newly renovated lower level with additional bedrooms and expansive family room. This area is ready for your touch and enjoys walkout access to the yard and pond. The 2nd level of the barn is currently a wood shop with wood-stove and a 2nd access from the road allows for storing large pieces or equipment on this upper level. The ground level of the barn has traditional sliding barn doors and extensive parking in front. Underground power and water lines travel from the house to a nearby site where another barn or horse arena could be built. A unique home treasure and like its organic architectural design the land has its own special quality of character and beauty. 191 acres are in the VT Land Use program. There is a 6 bedroom septic.

Type:
Single Family
Sq.Ft.:
2,710
Status:
Active
Beds:
4
Lot size:
1.79 Acres
Year built:
1990
Baths:
4.00
MLS#:
5000203

ADDITIONAL INFORMATION

Nestled on a serene, quiet town maintained dirt road, this spacious home offers the perfect blend of tranquility and comfort. As you approach, you'll be captivated by the stunning long-range views that greet you from the expansive deck, a haven for relaxation and outdoor enjoyment. The deck overlooks a picturesque pond, not on the property but offering a beautiful, calming view that enhances the natural charm of the setting all the same. Step inside to discover a thoughtfully designed interior where ample space meets cozy. The large, finished basement is a true bonus, featuring a cozy and convientent propane stove and serving as an ideal games room or entertainment space for family and friends. Featureing 4 large bedrooms, 3.5 bathrooms, with large primary ensuite, large living room with views and that all enticing party or craft space in the below. This is equally a perfect vacation retreat or spacious family home. Conveniently located close to the popular ski areas of Okemo, Stratton, and Magic this home is perfect for winter sports enthusiasts. Whether you're seeking a peaceful year-round residence or a seasonal getaway, this property promises a lifestyle of serene beauty and endless recreational opportunities. Welcome home to your personal oasis.

Type:
Single Family
Sq.Ft.:
2,772
Status:
Active
Beds:
4
Lot size:
32.97 Acres
Year built:
1860
Baths:
3.00
MLS#:
5000207

ADDITIONAL INFORMATION

Welcome to this beautiful historic farm dating back to 1825. At one time known as the Thompson Farm, in 1995 it was purchased by the current owner who lovingly restored it to its former glory. In 1999 it became the "Jersey Girls Farm". Attention was given to retain all of the antique charm, including keeping the original slate roof on main house, all original doors and original wide board floors. The house was also modernized with conveniences such as a new heating system, new wiring, new windows (retaining the original design), and a full array of solar panels to make the house fully self-sufficient. You will find plenty of room and charm inside, beginning with the large country kitchen which includes a working antique Glenwood stove. There's a huge pantry which doubles as a laundry room. The dining room, living room, library, one bedroom, and spacious 1/2 bath complete the downstairs living area. On the second level are 3 large bedrooms and a full bath in the main structure. The expansive master suite even has a spa tub! This room has a 2nd stairway which leads you back to the kitchen. On almost 33 acres of open and wooded land, all of which sits at the end of a town-maintained road. There's a large pond for swimming, fishing, or even kayaking. 5 outbuildings including a nice 1800's 30 x 80 barn! Endless possibilities: small dairy or horse farm, Airbnb, or bed and breakfast. Just 5 minutes to Chester. Shopping, hospital, skiing at Okemo, I-91 - all within 15 - 20 minutes!

Type:
Single Family
Sq.Ft.:
2,356
Status:
Active
Beds:
4
Lot size:
1.3 Acres
Year built:
1989
Baths:
4.00
MLS#:
4996384

ADDITIONAL INFORMATION

Luxurious contemporary home in a naturalized setting. Beautiful mountain views from family room and expansive deck. This home is a unique blend of country charm and modern convenience. Everyone will gather round the large center island in this amazing kitchen designed for cooking and entertaining. Open concept floor plan flows from kitchen to dining area and into the family room where you can set and take in the mountain views beyond. Slider leads to the deck combining indoor and outdoor living space. A private den is connected to the family room with French doors and can be opened up for addition living space or closed off for a quiet retreat. Second floor has three generous sized bedrooms, two of which are en suites. There is also a bonus room on the second floor that can be used for crafts, or additional den, home office or playroom. Wired for generator as well. Currently used as a family getaway and Airbnb. Home is located within minutes from year-round outdoor fun. Chester Recreation Center has a beautiful pool and lots of play area too. There are also local swimming holes, lots of hiking trails with lots to do. Just 18 minutes to the ski lifts at Okemo.

Type:
Single Family
Sq.Ft.:
2,702
Status:
Active
Beds:
4
Lot size:
0.89 Acres
Year built:
1850
Baths:
2.00
MLS#:
4994539

ADDITIONAL INFORMATION

Fully furnished! This home on .89 acres is located in the beautiful area of Gassetts in Chester, Vermont. Zoning is versatile and provides a wide range of options for commercial, retail, residential, or industrial use. Whether you're seeking a year-round vacation home or a weekend getaway, this beautiful mountain retreat offers the ideal combination of luxury, location, and outdoor adventure. 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quarts countertops, new sheetrock and paint in the majority of the house, new sub flooring in the living room, laundry area, and mudroom, new window sills, new mini split, removal of all previous knob and tube wiring, replaced windows, new french door in the living room, new patio and fire pit area, freshly leveled and graveled driveway, two-car carport, refinished front deck, and freshly leveled backyard. This three bedroom, two bathroom home has an open concept. The three bedrooms are located on the second floor, with one bathroom being on the first floor as well as the second. Hiking, mountain biking, and snowmobiling trails surround the town, making this home ideal for anyone who enjoys the natural beauty of Vermont. High speed internet is available (currently VTEL).

Type:
Single Family
Sq.Ft.:
1,728
Status:
Active
Beds:
4
Lot size:
1.12 Acres
Year built:
1980
Baths:
2.00
MLS#:
4986618

ADDITIONAL INFORMATION

Looking for the perfect ready to move in home in Vermont? Look no further than this French Provincial meets Vermont cabin centrally located in the quiet town of Chester, Vermont on Route 103. Within an hour drive to 5+ great ski mountains, within 10 minutes to Okemo mountain. House features so many great amenities and improvements--new black/grey roof just installed June 2024, new egress windows, beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes and state parks, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today! Added bonus is owner is willing to offer financing with 30% down payment to approved buyer.

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Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067



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Chester Real Estate

The median home value in Chester, VT is $591,500. This is higher than the county median home value of $334,800. The national median home value is $338,100. The average price of homes sold in Chester, VT is $591,500. Approximately 55.38% of Chester homes are owned, compared to 14.63% rented, while 29.98% 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!

Chester, Vermont has a population of 3,010. Chester is less family-centric than the surrounding county with 24.13% of the households containing married families with children. The county average for households married with children is 26.01%.

The median household income in Chester, Vermont is $61,397. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Chester is 53.2 years.

Chester Weather

The average high temperature in July is 81.5 degrees, with an average low temperature in January of 7.4 degrees. The average rainfall is approximately 45.2 inches per year, with 67.6 inches of snow per year.

Chester Real Estate Market Conditions

  • Median sales price

    $591,500
    19.1% change since last quarter
  • # Active listings

    38
    30-day change

Chester Schools and Demographics

Education near Chester, VT

Metric City County
High School Graduates 96.52 94.16
College Degree - 2 year 6.97 8.49
College Degree - 4 year 40.18 40.21
Graduate Degree 11.68 12.49
Expenditures per Student 26,463 26,463
Students per Teacher 12.3 12.3

Elementary Schools near Chester, VT

School Grades Students P/T Ratio ZIP
Chester-Andover USD #29 PK - 06 261 13 05143
Elm Hill School PK - 02 415 17.7 05156
Flood Brook USD #301 PK - 08 322 11.1 05148
Grafton Elementary School PK - 06 103 13.7 05146
Ludlow Elementary School PK - 06 115 8 05149
Union School 03 - 05 256 10 05156

Middle Schools near Chester, VT

School Grades Students P/T Ratio ZIP
Riverside School 06 - 08 291 11.2 05156

High Schools near Chester, VT

School Grades Students P/T Ratio ZIP
Black River USD #39 07 - 12 172 8.6 05149
Green Mountain UHSD #35 07 - 12 336 10.2 05143
Springfield High School 09 - 12 433 11.9 05156

Ungraded Schools near Chester, VT

School Grades Students P/T Ratio ZIP
River Valley Technical Center UG - UG 0 05156

Demographics near Chester, VT

Metric City County
Neighborhood Type Small town
Population 3,010 57,593
Population Density 54 59
Median Age 53.2 47.8
People per Household 2.4 2.3
Median Household Income 61,397 63,787
Average Income per Capita 35,517 39,377