The agencies at Chester
These agencies offer a selection of luxury properties vente at Chester. Feel free to contact them for personalized assistance.
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, youll 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.
…By Four Seasons Sotheby's International Realty
Privately sited on 42 pastoral acres, this gracious Vermont country retreat offers approximately 4,000 square feet surrounded by expansive lawns, perennial gardens and two picturesque ponds. The four-bedroom, four-bath residence is ideal for comfortable living and entertaining, with red birch floors, nine-foot ceilings and wonderful connections to the outdoors through multiple screened porches, a sunny deck and covered porch. At the heart of the living room is an impressive wood-burning fireplace, handcrafted with stone gathered from the property and finished with a custom cherry mantel. Three additional gas fireplaces add warmth throughout the home. The spacious kitchen is ready for a crowd, with Vermont soapstone countertops, a butcher-block island, three sinks and three dishwashers. The main-level primary suite enjoys its own gas fireplace and screened porch. Upstairs are two additional bedrooms, two baths and a handsome library with built-in shelving, fireplace and access to a balcony overlooking the landscape. Multi-zone radiant heat and central air provide year-round comfort, while the full basement includes a wine cellar, play area and generous storage. Outdoors, enjoy a heated 16' x 32' saltwater pool, two ponds, blueberry and raspberry bushes, beautiful gardens and stone walls. A detached 1,500-square-foot barn offers workshop and storage areas plus a guest suite with bedroom, bath and kitchenette. Tucked away in a peaceful setting yet just minutes from Ludlow Village and Okemo Mountain Resort, this is a wonderful place to experience the best of Vermont in every season.
…By Four Seasons Sotheby's International Realty
This light-filled contemporary home offers end-of-road peace and quiet privacy yet within walking distance to Ludlow Village shops and restaurants. Enjoy Okemo Mountain views from the great room with vaulted ceilings, cherrywood floors, a floor-to-ceiling brick chimney with wood stove, and walls of glass open to the spacious outside deck. The kitchen offers a granite island with seating that flows into the dining room making it ideal for entertaining. The main-level primary suite provides easy one-level living, while the upper level includes two additional bedrooms, a bath, and a bright loft-style family room with mountain vistas. The lower level includes an attached garage, laundry area and bonus space. Envision yourself having morning coffee on the deck, gathering around the fire after a day of skiing and enough separate space for family and guests to spread out. Quality construction throughout, this home is perfect for those seeking an easy keeper!
…By Four Seasons Sotheby's International Realty
Sunday 8/16 Open House is being CANCELED! Experience the very best of Vermont living in the charming village of Weston, where every season offers something to enjoy. Spend winter days skiing at nearby Stratton, Magic, Bromley, or Okemo, and warmer months hiking scenic trails, horseback riding, swimming in lakes and ponds, or taking in a performance at the Weston Theater Company. Explore local shops, galleries, and restaurants while enjoying the beauty of one of Southern Vermont's most beloved communities. Whether you're seeking outdoor adventure, a vibrant arts community, or simply the peace and beauty of Vermont, this exceptional property places it all within easy reach.Thoughtfully built and impeccably maintained, this 4 bedroom, 3 bath home reflects exceptional pride of ownership with thoughtful upgrades throughout. Set on a beautifully landscaped property with a private swimming pond, it offers the perfect balance of comfort, privacy, and year round recreation.Designed for gathering, the home features a spacious open kitchen and dining area, inviting living and family rooms, and a generous mudroom ready for skis, hiking boots, and outdoor gear. A first floor den with an adjacent full bath offers flexibility as a guest room or first floor bedroom.Upstairs are four comfortable bedrooms, a dedicated office, and a spacious laundry room. The primary suite is a true retreat with a large walk in closet, oversized bath, soaking tub, and mountain views.A full basement with bulkhead access provides excellent storage and endless potential for a fitness room, workshop, or future finished space.Outside, mature perennial gardens frame the home, while a covered front porch and sun-filled back deck with a hot tub provide the perfect setting to relax and enjoy the mountain views. The private swimming pond completes this exceptional Vermont retreat.
…By Four Seasons Sotheby's International Realty
Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations.Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace anchors the living space. The kitchen with premium appliances flows into the dining and living areas, creating an inviting setting for entertaining and everyday living.The main residence features three ensuite bedrooms, including a lower-level suite and an upper-level suite that could each serve as a primary bedroom, depending on how the home is used. Additional living spaces provide flexibility for guests, recreation, remote work, or additional sleeping accommodations. A separate one-bedroom guest cottage offers added privacy and versatility.Designed for both gathering and retreat, the property includes multiple decks, a covered porch, open meadow, and expansive fenced acreage. A three-car garage and solar power system further enhance functionality and efficiency.Conveniently located near Stratton, Bromley, Magic, and Okemo Mountains, as well as Lowell Lake, Manchester, Weston, Londonderry, and South Londonderry, the property provides easy access to skiing, hiking, cycling, fishing, golf, shopping, dining, and cultural attractions throughout the region.224 Cobble Ridge Road presents a rare opportunity to own a private Southern Vermont retreat combining quality craftsmanship, flexible living spaces, and exceptional access to the region's four-season amenities.
…By Four Seasons Sotheby's International Realty
This Weston gem, expanded and rebuilt by the seller in 2003, has been loved and cared for and is now ready for its next lucky owner. Set on a south facing hill on a quiet country road, it promises sunlight and mountain views all year long. Protected on 10 wooded acres, it borders the National Forest while benefitting from a rolling lawn, small pond and decorative gardens. Designed for one floor living, the home has a surprising amount of space, from the open concept kitchen, dining room and living room with wood burning fireplace to the 2 bedrooms and baths, a year round sunroom with wet bar, and a home office. A welcoming mudroom, a large front deck with a retractable awning, and a lower level garage and abundant basement storage complete the picture. Suitable for year-round living yet easily maintained for seasonal use, the property is convenient to the vibrant village of Weston with its Vermont Country Store, Weston Theater, and fine cafes, and a short drive to Okemo, Bromley, Magic and Stratton. Hike the back roads and hills, enjoy recreation at nearby Hapgood Pond, Lowell Lake, and the Weston Recreation Area, then return to relax in your cozy Green Mountain retreat. The house is empty; select photos have been virtually staged. Property being sold As Is.
…By Four Seasons Sotheby's International Realty
One-of-a-kind Lake Rescue sanctuary with 179 feet of shoreline, stone walls, perennial gardens, apple trees, and a sprawling flat lawn perfect for games and gatherings. Offering exceptional flexibility, this special setting on 4.35 acres has the potential to become a family compound, multi-generational retreat, or income-producing investment. A 3-bedroom septic permit is already in place, creating the opportunity to build an additional home along the water and establish a legacy for generations to come. Inside, pine floors run throughout the home, complemented by a chef's kitchen and a deck with hot tub just outside the sliding doors. Spend summer days swimming, boating, and relaxing by the dock, with a lakeside shed to store all your gear. The property also features a large barn with abundant storage and a one-bedroom apartment over the garage, ideal for guests, extended family, or rental income potential. A rare Lake Rescue retreat with endless possibilities, all just minutes from Okemo. Come enjoy the very best of lakefront and mountain living.
…By Four Seasons Sotheby's International Realty
With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone.The newer addition features an open concept kitchen, dining, and living area anchored by a custom stone fireplace and dramatic floor to ceiling windows framing the mountain views. A sun-filled deck invites morning coffee, summer entertaining, or cozy apr?s ski evenings. The primary suite is a private retreat with its own deck, ensuite bath, walk in closet, and dedicated office.The original wing offers four additional bedrooms, a kitchen, living area, and its own deck, creating an ideal space for guests or extended family. Whether enjoyed as one expansive residence, configured for private guest accommodations, or explored for its income-producing rental potential, the flexible layout adapts to a variety of lifestyles.Located in the heart of Brownsville. Just minutes from Mount Ascutney's trails and outdoor recreation, and within easy reach of Woodstock, Okemo, Killington, and the Upper Valley, this is a rare opportunity to own a true Vermont retreat where unforgettable memories are made all year long, with the added flexibility of potential rental income when you're away.
…By Four Seasons Sotheby's International Realty
Welcome to this beautifully updated Hawk home with expansive westerly mountain and valley views. Recent improvements throughout give the home a fresh, inviting feel while keeping its warm Vermont character. The renovated mudroom features custom live-edge maple walnut benches, shiplap walls, new lighting, shelving, and plenty of space for all your gear. The redesigned kitchen has granite counters, cherry cabinetry, stainless appliances including a 6-burner commercial stove and double wall ovens, plus an updated bar area with new sink, fixtures, and shiplap accents.The living room is bright and welcoming with cathedral ceilings, built-ins, refinished floors, and a dramatic stone fireplace. Sliders from both the dining area and living room open to the large covered deck, where recently cleared trees now reveal unobstructed mountain views.Upstairs, the loft has been completely renovated with new flooring, ceiling, and a remodeled staircase, creating a great hangout space to play pool. The mid-level includes the spacious primary suite with private balcony and a large bath with double vanity, jetted tub, and separate shower, along with a bunk room, additional bedroom, and full bath.The lower level offers another bedroom, two more bunk rooms, a fully renovated bath, laundry area, and a family room with wet bar and sliders leading to the hot tub deck. Fresh paint, updated lighting and fixtures, accent walls, and new furnishings throughout complete this move-in ready retreat, ideally located between Killington and Okemo.
…By Four Seasons Sotheby's International Realty
Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions provide 13 extra bedrooms, library, game room, and a vintage bar/lounge area. The Grounds: Woods, trails, 2 ponds, and a 2 bay outbuilding workshop and equipment storage. The Potential: 875 sq. ft. of bonus space ready for your finishing touches, possibly a theater or a gym? This is the ultimate gathering place for creating memories that last a lifetime. Don't just visit Vermont, own a piece of its history. All measurements approximate. Listed commercially as well, MLS#5075319
…By Four Seasons Sotheby's International Realty
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These agencies offer a selection of luxury properties vente at Chester. Feel free to contact them for personalized assistance.