Chester Homes with ChesterAndover USD 29 School district

Welcome to Chester, Vermont – a charming town nestled in the heart of Windsor County, where picturesque landscapes and a tight-knit community come together to create a truly idyllic living experience. Known for its stunning natural beauty, Chester is surrounded by lush green mountains and rolling hills, making it a haven for outdoor enthusiasts. Whether you enjoy hiking, skiing, or simply taking in the breathtaking views, Chester offers an abundance of recreational opportunities year-round.

One of the standout features of this quaint town is its commitment to education, supported by the Chester-Andover USD 29 School District. Families looking to settle here will find a nurturing environment for their children, with schools that prioritize academic excellence and personal growth. The district fosters a sense of community, ensuring that students receive individualized attention and a well-rounded education.

The real estate market in Chester boasts a diverse range of homes, from charming historic properties to modern new builds, catering to various tastes and budgets. Each neighborhood reflects the town's unique character, providing residents with a sense of belonging and pride. The friendly atmosphere is complemented by local shops, delightful eateries, and vibrant community events that bring everyone together.

Living in Chester means embracing a lifestyle enriched by nature, community, and education. If you’re searching for a home in a town that values tradition, quality of life, and a strong sense of community, Chester, Vermont, is the perfect place to call home. Discover your dream home in this enchanting corner of the Green Mountain State today!

Newest Chester Homes with ChesterAndover USD 29 School district

$1,200,000

4 Beds ⋅ 3 Baths ⋅ 5088175 MLS

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the fire pit beneath star filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55’ x 40’ barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small town charm that make Vermont so special.

76 Goldthwaite Rd, Chester

$99,999

5082636 MLS

This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn, ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifully, creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.

508 Mattson Rd, Chester

$399,000

4 Beds ⋅ 3 Baths ⋅ 5073147 MLS

This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.

40 Fenton Rd, Chester

$169,000

1 Beds ⋅ 1 Baths ⋅ 5067929 MLS

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway. A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons. This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

3019 Popple Dungeon Rd, Chester

$650,000

5044879 MLS

Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic. In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use. Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, it is conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow. This versatile property allows for multiple avenues of income - whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless. Don't miss your chance to own a piece of this thriving community.

3630 Vt Route 103 N, Chester

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