The agencies at Chester
These agencies offer a selection of luxury properties vente at Chester. Feel free to contact them for personalized assistance.
Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive.The heartbeat of the home comes from a bright and inviting great room that opens through sliding doors to an expansive deck where mornings begin with coffee and birdsong, and evenings end with the sound of rushing water under the stars. The flowing layout offers spaces that adapt beautifully to modern living a dedicated office for remote work, room for a home gym, studio, creative retreat, media lounge, or whatever your lifestyle calls for next.The dining room is ready for gatherings both large and small, while the attached 2-bay garage and generous outdoor space make everyday living feel effortless. Whether you're hosting friends, growing a garden, creating art, working from home, or simply looking for a peaceful place to recharge, this property offers the flexibility to make it your own.Private yet convenient, peaceful yet connected this home delivers a lifestyle thats increasingly hard to find.
…By Four Seasons Sotheby's International Realty
Wild Trails Farm presents a rare opportunity to own 224 acres of private, contiguous land defined by rolling fields, mature woods, and expansive southern views. The setting feels secluded and serene, yet its fully equipped for comfortable, year-round living.At the heart of the property, the 5,600+ sq ft lodge is thoughtfully designed for both everyday life and entertaining. A spacious kitchen with dual dining areas anchors the home, complemented by multiple living spaces that offer flexibility for gathering or quiet retreat. Six bedrooms and 4.5 baths provide ample room for family and guests. Energy-efficient solar and geothermal systems support modern living, while the sauna adds a simple, restorative touch. The two-car garage, currently used as a yoga studio, can easily be returned to its original use. A screened porch and stone patio create seamless connections to the surrounding landscape in every season.The land itself is a standout feature224 acres of privacy, beauty, and usability. A network of private trails begins just outside the door, ideal for hiking, biking, snowshoeing, and cross-country skiing. Established gardens, fruit-bearing plantings, and peaceful ponds add to the propertys sense of place and seasonal enjoyment.Complementing the main residence, several additional structures enhance the propertys versatility: a beautifully restored circa-1800s barn with a two-bedroom apartment, a charming one-bedroom post-and-beam residence, a stable, equipment barn, and a greenhouse. Each building is well integrated, offering function and flexibility without excess.Whether envisioned as a private retreat, a multigenerational compound, or a property with income potential, this offering delivers a compelling combination of infrastructure, acreage, and settingready to be enjoyed and adapted to a variety of uses. Additional acreage available.
…By Four Seasons Sotheby's International Realty
Wild Trails Farm is the kind of property buyers wait years to find312 private acres of rolling fields, woods, and sweeping southern views, with a setting that feels completely removed yet remains incredibly livable.The 5,600+ sq ft lodge strikes an ideal balance between scale and comfort. Designed for everyday living, it features a welcoming kitchen with dual dining areas, multiple spaces to gather or spread out, and six bedrooms with 4.5 baths to accommodate family and guests with ease. Solar and geothermal systems provide efficiency without sacrificing comfort, while the sauna adds a touch of everyday luxury. The two-car garage is currently used as a yoga studio but can be easily converted back. A screened porch and stone patio make it easy to enjoy the landscape in every season.What truly sets this property apart is everything beyond the main home. The land itself is a defining asset312 acres of privacy and possibility. Miles of private trails begin at your door, ideal for hiking, biking, snowshoeing, or cross-country skiing. Wander through curated gardens, pick fruit in season, or spend quiet afternoons by the ponds.The additional buildings offer flexibility without feeling overwhelming: a beautifully restored circa-1800s barn with a two-bedroom apartment, a charming one-bedroom post-and-beam residence, a stable, equipment barn, greenhouse, and more. There is also a separate off-grid cabin and a treehouse tucked into the woodssimple, peaceful spaces to unplug and retreat.This is a property that works on multiple levels: a private estate, a multigenerational compound, or an income-producing retreat. The infrastructure is in place, the land is exceptional, and the setting is increasingly hard to replicate.Opportunities like this are rare. There is also the option to expand with additional acreage for those seeking even greater privacy and long-term value.
…By Four Seasons Sotheby's International Realty
Designed both as a peaceful retreat and a comfortable home for entertaining, 28 Plumley Ridge offers the best of both worlds. The location is private yet central. Ludlow Village is within walking distance and Okemo Mountain is just over a mile away. This quality constructed home is thoughtfully designed for both contentment and convenience. The wide wrap-around deck provides year round vistas of Okemo. From the hot tub, you can watch the skiers by day and the twinkling lights of the groomers at night, all while listening to the tranquil sounds of the Jewell Brook below. A covered porch with plenty of storage was added in 2024. The mudroom has custom-built shelves to maximize storage, stone floors and radiant heat. Inside, warm cherry floors and a roaring wood fireplace provide the setting for cozy enjoyment. The open floor plan and floor-to-ceiling windows welcome south-western light to flood the home. The kitchen features granite countertops, newer stainless-steel appliances and a peninsula that is perfect for casual dining. The first-floor primary bathroom has radiant heat, along with a steam shower, in-ceiling speakers and a towel warmer. The second floor offers two bedrooms, a bonus room and an updated full-bath complete with a linen closet, stone flooring and walls, and a custom wood vanity. The carpeting throughout the second floor and lower level is all new as of 2024. The lower level family room provides plenty of room for a ping-pong table or a movie screening, along with generous storage. Turnkey, clean and ready to go!
…By Four Seasons Sotheby's International Realty
Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete the interior, with plenty of potential to update and make it your own. Recent improvements include a new metal roof and a newly drilled well, both completed within the past year, giving peace of mind for years to come.Located on Route 100, the property offers easy access to nearby towns. You are just minutes from the historic Weston Playhouse, the Vermont Country Store, and the village green, as well as a short drive to Okemo, Stratton, Bromley, and Magic Mountain for year-round recreation.The level lot provides space for a garden, patio, or simple outdoor enjoyment without the burden of extensive upkeep. Whether you are seeking a full-time residence or a vacation getaway, this home presents an affordable opportunity to own in one of Vermont's most desirable mountain towns where you can enjoy arts, dining, skiing, hiking, and the small-town charm that makes Weston so special.
…By Four Seasons Sotheby's International Realty
Set in the heart of Vermonts four season playground, this impeccably maintained 4 bedroom, 3 bath home with a private swimming pond offers the perfect balance of comfort, space and outdoor living. Thoughtfully built by the previous owners and meticulously maintained by the current owners, the property reflects care, pride, and attention to detail, with many thoughtful upgrades and improvements made. The location is hard to beat - just minutes to four premier ski areas: Okemo Mtn, Magic Mtn, Stratton Mtn, and Bromley Mtn. Conveniently located near shopping, dining, and amenities in Rutland, Weston, and Manchester, with nearby ponds and lakes adding to the endless year round recreation opportunities. Designed for gathering and relaxing, the home features a spacious open kitchen and dining area, inviting family room and living room, and a large mudroom ready for all your gear after a day of skiing, hiking, snowmobiling, or lake adventures. A first floor den with an attached bath offers wonderful flexibility and could easily serve as a first-floor bedroom for guests or those seeking single level living options. The spacious second floor includes four comfortable bedrooms, a dedicated office, and large laundry. The primary suite is a true retreat with a generous walk in closet, oversized bath, soaking tub w/ mountain views. A full basement with bulkhead access offers endless possibilities - ideal for storage, a workout area, workshop space, or future finished living space. Outside, mature perennial gardens surround the home, a covered front porch and sun drenched back deck with hot tub create the perfect setting to take in the mountain views and quiet surroundings. The stunning swimming pond completes this private Vermont oasis. Whether youre looking for a year-round residence or the ultimate Vermont getaway, this exceptional property offers the very best of Vermont living in every season.
…By Four Seasons Sotheby's International Realty
Enjoy year-round sunsets from this premier Lake Rescue location. With direct lake access, swim from your dock or launch your boat for a day on the lake. The sprawling flat yard is ideal for lakeside living, whether kicking a ball with the kids, playing badminton or for summer gatherings by the water. Recent improvements include a new 5-bedroom septic system, freshly painted exterior and main level interior, new kitchen counters and stove, new flooring, updated exterior deck railing and a bank of trees along the north border for added privacy. Mini splits provide air conditioning for warm summer days. Super close to Okemo Mountain Resort for skiing and golf. A rare opportunity to acquire one of the best spots on Lake Rescue!
…By Four Seasons Sotheby's International Realty
Set against sweeping views of Mount Ascutney, this distinctive property offers the kind of Vermont escape buyers rarely findprivate, spacious, and designed for gathering. Thoughtfully expanded over time, the home seamlessly blends two living spaces, creating an ideal setting for hosting extended family and friends while still offering comfort and privacy for all.The newer portion of the home is centered around light and connection, with an open-concept living, dining, and kitchen area anchored by a custom stone fireplace and framed by floor-to-ceiling windows that capture the mountain views. Step out onto the sun-drenched deckperfect for morning coffee, apr?s-ski evenings, or summer entertaining. The primary suite offers a peaceful retreat with its own private deck, ensuite bath, walk-in closet, and dedicated office space.The original wing of the home provides additional room for guests, featuring four bedrooms, kitchen and its own living area, as well as direct access to a second deck overlooking the surrounding landscapecreating a natural separation that makes hosting effortless.Whether used as a single expansive home or configured to offer private guest accommodations, the layout supports a range of lifestylesfrom weekend retreats to extended stays.Located in the heart of Brownsville, just moments from the trails and outdoor recreation of Mount Ascutney, this property offers four-season appeal. Enjoy easy access to the charm of nearby Woodstock, as well as skiing at Okemo and Killington, and the cultural and dining destinations of the Upper Valley.A rare opportunity to create a true Vermont getawaydesigned for connection, relaxation, and year-round enjoyment.
…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
Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening.With two distinct living areas, you'll find the ideal spaces for intimate gatherings during spring blooms or lively celebrations as summer stretches into long, lazy evenings. Step outside onto the deck, where a bubbling hot tub invites you to unwind under the stars, no matter the season.The spacious kitchen is ready for your culinary explorations, from summer barbecues to winter comfort food, making it the heart of your home in every season. Whether you're savoring the vibrant colors of fall, the fresh green of spring, or the serene snowfalls of winter, this Vermont home offers a sanctuary for all seasons.Don't miss your chance to own this four-season gem. Embrace the beauty of Vermont and create memories that will last a lifetime, no matter the time of year!
…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.