luxury houses for sale Chester, United States

Welcome to this well-cared-for 3-bedroom 1975 saltbox-style home, privately situated at the end of the road on 15 acres of level, mostly cleared land. Surrounded by open fields and perennial gardens, the property offers a peaceful setting with plenty of room to enjoy the outdoors and make it your own.The home features a two-car attached garage connected by a lovely sunroom, creating a bright and inviting transition between the house and garage. For those seeking additional space, the property offers a four-bay open structure ideal for equipment storage, workshop space, or additional vehicles. Two full horse stalls with direct access to a paddock provide an excellent opportunity for equestrian use.With its combination of open land, established gardens, versatile outbuildings, and private location, this property offers a rare opportunity to enjoy space and tranquility while remaining conveniently close to town, restaurants, and everyday amenities. Springfield Hospital and Route 91 are nearby, with skiing and a variety of outdoor recreational activities also within easy reach.Ready for its next chapter, this special property offers the space, privacy, and flexibility to create a peaceful year-round retreat.

A rare opportunity to own a remarkable piece of Vermont and literary history. Lovingly designed and restored by the creators of the beloved Llama Llama children's book series and the accompanying Netflix animated series, this extraordinary mini-estate is offered for the first time by the family.The meticulously restored and maintained five-bedroom, five-bath, 6,100+ square foot post-and-beam home seamlessly blends a late-1700s brick home, an 1820 clapboard addition, and thoughtfully designed post-and-beam additions completed in 2012. Historic character has been carefully preserved while incorporating modern construction, insulation, systems, a built-in generator, and today's amenities. Wide-plank hardwood floors, custom woodwork, vintage soapstone sinks with modern fixtures, antique hardware, and even a firepole reflect exceptional craftsmanship throughout.A soaring, light-filled studio where the bestselling books were created offers endless possibilities as a family room, entertaining space, creative studio, home office, gym, or home business. A rooftop deck overlooks the picturesque village of Lower Bartonsville and its iconic covered bridge. Above the detached two-car post-and-beam garage is a striking apartment or office with 20-foot ceilings and cork flooring.The 2.82-acre setting is equally extraordinary, with mature perennial gardens, remnants of an apple and pear orchard, whimsical stone stairways, and handcrafted stone walls built by renowned stonemason Dan Field. The property also overlooks an adjacent pond with ducks, herons and river otters.The centerpiece is the spectacular restored foundation of a 19th-century grist mill, reclaimed over 15 years and rising more than 60 feet in places. An adjacent 3.6-acre parcel with the historic mill dam is available separately.Minutes to I-91, The Vermont Country Store, Chester, and just 20 minutes to Okemo Mountain Resort. Showings start 8/3.

Welcome to a truly special Vermont property where craftsmanship, comfort, and the beauty of the outdoors come together. Offering over 3,000 square feet of beautifully renovated living space, this distinctive home is filled with custom features and exceptional woodworking throughout.The heart of the home is the custom kitchen, featuring rich cherry cabinetry and timeless soapstone countertops, complemented by numerous thoughtful updates. With four bedrooms, there is plenty of space for family and guests. The beautifully renovated primary bath offers a luxurious retreat with a stone and tile walk-in shower and a Jacuzzi soaking tub.Set on two picturesque acres, the property offers a peaceful Vermont setting complete with a babbling brook, mature perennial gardens, and ample space for additional gardening. Two fully functional workshops provide exceptional space for woodworking, hobbies, storage, or other creative pursuits.Located in a quiet neighborhood yet conveniently close to schools, the hospital, Route 91, and Okemo Mountain, this property puts year-round outdoor recreation and everything Vermont has to offer within easy reach. Whether you're looking for a beautifully crafted home, a gardener's haven, a workshop enthusiast's dream, or simply a peaceful place to call home, this one-of-a-kind property is ready to welcome you.

Grafton Lodge is a striking five-bedroom, four-bathroom timber frame retreat set on 72 acres of complete privacy, directly bordering the 146-acre Putnam State Forest. Built in 2022, this 4,000+ sq ft home blends timeless craftsmanship with modern comforts, featuring wide hemlock floors, exposed beams, and walls of windows that invite the natural surroundings inside.At the heart of the home is a dramatic two-story great room, offering panoramic forest views and anchored by a wood stove for cozy winter nights. Heat pumps ensure year-round climate control, while thoughtful design provides comfort across three spacious levels, including a game room, exercise area, and home office. A spiral staircase leads to a bonus loft space on the fourth floor--ideal as a studio, library, or creative escape.Step outside to your own private sanctuary: a stone patio outfitted with a sauna, hot tub, fire pit, and grill--perfect for relaxing or entertaining under the stars. The property includes a state-approved wastewater permit for a future 4-bedroom cabin, offering excellent potential for expansion or guest accommodations. Conveniently located just 3 miles from Grafton Village and within easy reach of Okemo, Magic Mountain, and Bromley for skiing, plus direct access to VAST snowmobile trails. Stay connected with fiber optic internet, and rest easy with a backup generator. The property is being offered fully furnished and enrolled in Vermont's Current Use program for tax benefits.

Write your Vermont story at this extraordinary 38-acre retreat just one mile from Grafton Village, set along the peaceful Saxtons River. Built in 2007, the seasonal one bedroom cottage with loft blends beautifully into the natural landscape and captures the very best of indoor and outdoor living. Perched above the waters edge, the cottage offers a screened porch, two sliding doors from the main living space to a deck overlooking the river, a new bathroom, and an outdoor shower with river views. From the bedroom, the sound of moving water creates the kind of quiet, restorative experience that defines this special place. A natural stone patio with built-in firepit creates another intimate outdoor space surrounded by the sights and sounds of the land. The new bath is being connected to an existing five bedroom state permitted wastewater system, with the cottage using one bedroom allotment and capacity remaining for a future separate three bedroom residence. The property is currently being served by a spring fed, shallow dug well. Designed for recreation and retreat, the property features a spring fed swimming pond, pond house with electricity, loft space, open gathering area, and a masonry patio at the waters edge. Additional outbuildings include a pavilion beside a fire pit in the field. Above the cottage, a beautiful meadow opens to the mountains and leads to a private trail ascending to an observation deck with sweeping views over the surrounding farms and the church steeples of Grafton Village. Close to VAST snowmobile trails and outdoor recreation at the Grafton Trails & Outdoor Center, this is a rare Southern Vermont offering that can be enjoyed immediately while planning an exceptional future estate.

Set among the rolling hills of Andover, this inviting three bedroom home captures the best of Vermont living with beautiful long range views, morning sunlight and a peaceful country road setting. Whether youre looking for a full-time home, weekend escape or four-season retreat, this property offers the space, flexibility and setting to settle in and truly enjoy it.Ideally positioned for year-round recreation, youre within easy reach of some of Vermonts most sought-after ski destinations, including Okemo, Magic, Bromley, Stratton, Mt. Snow, and Killington. Nearby Manchester, Chester and Ludlow add charming village centers, restaurants, shops and everyday amenities, making it easy to enjoy both adventure and convenience.Inside, natural light fills the main level, with large windows bringing the surrounding landscape into the living spaces. The remodeled kitchen features granite countertops and a center island with cooktop and dishwasher, while a wood cook stove creates a warm atmosphere. The finished lower level adds even more room to spread out, along with a half bath. Unfinished basement space could add additional living, relaxing, or play space.The three-bay garage is a standout feature, with substantial finished space above that includes a spacious great room, office, full bath and walk-in closet. Whether envisioned as guest quarters, a home office, creative studio, fitness space or additional living area, the possibilities are impressive.Outside, the Vermont lifestyle really comes alive. Gather around the firepit as the sun sets over the hills, or slip into the private covered hot tub tucked behind the house for a quiet evening under the stars. An additional carport provides convenient covered parking and storage.A versatile Vermont property with views, privacy, flexible living space and easy access to some of the regions best four-season recreation this is the kind of place that makes it easy to slow down, get outside and enjoy coming home.

Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare opportunity just 30 minutes to Hanover, NH, Dartmouth College, and Dartmouth Hitchcock Medical Center.For medical professionals relocating to the Upper Valley, this property provides privacy, acreage, and panoramic views at a value rarely found closer to Hanover or Lebanon. Easy access to I 91 allows a comfortable commute to Dartmouth Hitchcock Medical Center while enjoying a peaceful Vermont setting.The open concept layout offers a desirable main level living option and is well suited for multigenerational living or extended guest stays. Hardwood floors, tall ceilings, and expansive windows fill the home with natural light. The spacious kitchen is ideal for entertaining with granite countertops, high end cabinetry, built in refrigerator, wine fridge, and a generous island with prep sink. Both the living room and den feature fireplaces and custom built ins.Upstairs bedrooms offer comfort and privacy. The walkout lower level with tall ceilings and natural light provides excellent expansion potential for recreation space, gym, or media room.The three-car attached garage includes a separate bay with private entrance and direct access to unfinished space above, ideal for a future guest suite, studio, or in law apartment.Outside, enjoy a spacious deck, fire pit area, cleared yard, fenced pen, and spring fed pond. Convenient to Okemo Mountain Resort, Lake Sunapee, Crown Point Country Club, and Upper Valley amenities.Approximately 2 hours to Boston, MA and under 3 hours to Fairfield County, CT, offering strong appeal for both primary and second home buyers seeking Vermont lifestyle with New England accessibility.

Nestled along the Saxtons River, moments from historic Grafton, this beautifully restored Colonial farmhouse offers a rare blend of Vermont history, modern luxury, and exceptional curb appeal.Originally built circa 1820, the home has been meticulously reimagined and rebuilt with extraordinary attention to quality and architectural integrity. The renovation includes new plumbing, electrical, insulation, Marvin windows, restored foundation work, new siding, plaster walls and ceilings, and whole house central air conditioning a rare luxury in a 200 year old Vermont home. A newly built covered front porch and graceful wraparound driveway create a quintessential Vermont arrival.Inside, original details are complemented by refined finishes, including new wide plank floors on the first level matching refinished original floors upstairs. The chefs kitchen features custom cabinetry, quartz countertops, double dishwashers, and a 48 inch AGA dual fuel range. A second fully equipped kitchen serves the attached guest cottage, offering flexibility for guests, extended family, entertaining, or potential income use.The five bedroom residence offers multiple gathering spaces and an easy, gracious flow. Outdoors, the property captures the best of Vermont living, with more than five picturesque acres, river frontage, a crystal clear swimming pond, landscaped grounds, and a charming pool house. Along the river, a stone wall patio offers a peaceful place to gather, with steps to the waters edge.A classic former dairy barn adds character and possibilities for storage, hobbies, recreation, events, or creative use.Private yet convenient, the property is within walking distance of one of Vermonts most beloved villages, known for its historic architecture, village green, inn, galleries, recreation, and sense of community. A rare legacy property where historic charm, modern comfort, river frontage, pond, acreage, barn, village proximity, and storybook curb appeal come together.

At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an extraordinary lifestyle in one of Vermont's most picturesque communities.As you arrive you are welcomed by beautifully landscaped grounds, mature perennial gardens, and a private wooded setting that creates a true sense of seclusion. Despite its peaceful surroundings, the property is just minutes from Grafton Village and within 45 minutes of several premier Southern Vermont ski resorts, making it an ideal year-round residence, vacation home, or family retreat.Offering four bedrooms, four bathrooms, and numerous living and gathering spaces, the home is perfectly suited for hosting family and friends. The well-appointed chef's kitchen features an island with seating, abundant workspace, and easy access to the home's entertaining areas. A spacious family room with a stunning stone fireplace, private bath, and loft above serves as a centerpiece of the home, while three additional working fireplaces add warmth and character throughout. A second-floor den and game room provide flexible living space for relaxation, recreation, or remote work.Outdoor amenities are equally impressive. Enjoy summer days by the inground swimming pool, tend to the gardens, or explore the surrounding landscape. For horse enthusiasts, the property includes a four-stall barn and fenced pastures. Additional features include a two-car garage, clean and spacious basement, garden shed, and abundant storage throughout.Whether you're searching for a Vermont equestrian property, luxury country home, or four-season retreat near skiing and outdoor recreation, this remarkable Grafton estate offers you the very best.

Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience.Inside, warm hardwood floors, abundant natural light, and classic architectural details create a welcoming atmosphere. The spacious living room is anchored by a wood-burning fireplace, creating a warm and inviting gathering space for family and friends. Just beyond, the library/den offers a quiet retreat to unwind with a favorite book in front of the home's second wood-burning fireplace, making it one of the home's most inviting spaces.The kitchen blends timeless character with everyday functionality. Rich cabinetry, generous workspace and a spacious walk-in pantry that provides abundant storage along with additional prep space ideal for entertaining.The screened porch offers a peaceful place to enjoy morning coffee, summer dinners, or a quiet afternoon while overlooking the beautifully landscaped grounds. Protected from the elements yet open to the fresh Vermont air, it becomes a favorite gathering place throughout the warmer months.Each bedroom features its own private en-suite bath, providing exceptional comfort and privacy for family and guests. The primary suite serves as a relaxing retreat with hardwood floors, abundant natural light, and a well-appointed bath.Outside, perennial gardens frame the home with colorful blooms throughout the growing season, complementing the stone walkways and classic Vermont landscaping. An attached two-car garage provides convenience and additional storage. Located just minutes from the charming village of Grafton, you'll enjoy one of Vermont's most treasured communities.

Meticulously maintained and thoughtfully designed, this three-bedroom, three-bath home offers the perfect balance of comfort, functionality, and classic Vermont charm. Set on a picturesque parcel with stunning long-range views, the property is surrounded by mature trees, a small pond, established gardens, and simple, easy-to-maintain landscaping that enhances the natural beauty of the setting.Inside, inviting living spaces are filled with natural light, including a four-season sun room where you can enjoy peaceful mornings with a cup of coffee while taking in the changing landscape throughout the year. The thoughtfully designed floor plan provides comfortable gathering spaces that feel warm, welcoming, and perfectly suited for everyday living or entertaining.A two-car garage is complemented by a heated bonus room above, offering flexible space for additional guest accommodations, a home office, studio, or private getaway room. The custom heated barn is a truly unique feature of the property. Currently used as a woodworking shop, it also offers exceptional flexibility as an entertainment space, hobby barn, or additional guest sleeping area, making it ideal for hosting family and friends.As the day winds down, gather on the back patio and stone surrounded firepit to enjoy the sweeping views and spectacular Vermont sunsets, with simple perennial gardens creating a peaceful backdrop for relaxing or entertaining outdoors.Beyond the property itself, Grafton is one of Vermont's most treasured villages, known for its historic charm, welcoming community, and year-round recreation. Nearby Grafton Trails & Outdoor Center offers miles of hiking, cross-country skiing, snowshoeing, and skating trails, while the village is home to beloved destinations including MKT, Grafton Cheese Company and the historic Grafton Inn, all favorites for dining and spending time with friends and family.

Nestled in a postcard perfect riverfront setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Property is being offered furnished and turn key! Set on over two park like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, youll find a spacious eat in kitchen with abundant counter space and cabinetry perfect for gatherings and everyday living. Flexible living areas include multiple options for relaxing and entertaining, plus a second floor space ideal for TV viewing or a home office. A finished bonus room above the attached two-car garage provides excellent guest overflow or creative studio space. The partially finished basement features a comfortable family room for additional versatility.The home offers three bedrooms, including a convenient first-floor en suite primary. Step out onto the back deck and take in breathtaking views of the river as it gently flows below. A private walking trail winds along the riverbank to the far end of the property, enhancing the serene, retreat like feel.Additional highlights include a charming carriage house with many potential uses and the peace of mind of a whole house generator. Home is also being offered mostly furnished and ready for its new owners. Located just a short distance to town amenities, this remarkable property captures the very best of Vermont living. OPEN HOUSE SATURDAY AUGUST 15th 11-1pm

Set on 157 private acres with sweeping long-range views of the Connecticut River, this meticulously restored circa 1735 Cape offers a rare blend of historic character, refined comfort, and estate-scale amenities. Completely dismantled and rebuilt with care, the post-and-beam residence displays exposed beams, wide-board floors and sheathing, gunstock corner posts, and classic brick fireplaces alongside thoughtful modern upgrades. The inviting renovated kitchen features an oversized fireplace, high-end appliances, and expansive views of the swimming pond with distant views of the Connecticut River. Three en-suite bedrooms include a gracious first-floor primary suite enhanced by a 30-by-20-foot addition. A detached one-bedroom guest cottage with a four-bay garage, a separate utility barn, walking trails, and a 40-acre maintained hay field creates an exceptional private retreat. Mechanical upgrades, a concrete basement, and a whole-house generator provide ease and reliability, with convenient access to Interstate 91, all-season recreation, and Hartness State Airport approximately 20 minutes away. 4 hours to NYC, 2.5 hours to Boston.

Bringing generations together in a place that inspires connection, adventure, celebration, work and stewardship, Moosewalk Lane is a purpose built multigenerational family compound. Created over two decades and set on 384 private acres in Vermont's Green Mountains, Moosewalk Lane is offered fully furnished and equipped. Anchored by a 10,062 square foot timber frame home, guest house, writer's cabin, equipment barn, and miles of private trails, Moosewalk provides a true sense of place where comfort, privacy, and recreation exist in equal measure.Designed for year round living and entertaining, the compound comfortably accommodates extended family, friends, and guests with eight bedrooms, seven full baths, a dramatic two story great room, a chef's kitchen with Viking appliances and an Italian wood fired pizza oven, a library, media and game room, fitness space, six garage bays, and thoughtfully designed gathering places both inside and out.Just beyond the backyard, Broadway, the property's original logging road turned trailhead, provides direct access to the balance of the 384 acre property and four season recreation. Ride horses through open meadows, hike, snowshoe, or explore miles of private woodland trails, produce maple syrup from your own gravity fed sugarbush, enjoy direct access to Vermont's VAST trail system, or retreat to the writer's cabin overlooking the Connecticut River Valley. Historic stone walls, managed hardwood forests, abundant wildlife, and protected Current Use acreage reflect more than ownership, they reflect stewardship.Thoughtfully created for extended family, private retreats, entertaining, or simply escaping the pace of everyday life, Moosewalk offers something increasingly rare: a place where time slows, memories are made, meals are shared, and life is measured by moments well spent.

The smell of woodsmoke on a crisp alpine afternoon, the quiet crunch of fresh powder underfoot, and the sense that the rest of the world has dropped away, this is the reality waiting at the top of Powder Mill Ridge. Tucked into three acres of private Vermont forest, this contemporary retreat is designed less like a standard house and more like a basecamp for a life well lived.Winters mean stepping right out your door and onto local trails, spending the afternoon carving through fresh snow, and returning home with frozen cheeks to sink into the bubbling hot tub. In the summer, those same paths transform into a network of shaded hiking trails, where the only soundtrack is the wind through the hemlocks. Inside, the home strikes a balance between clean, contemporary lines and classic mountain warmth. The open-concept main floor encourages everyone to gather around the kitchen and dining spaces, sharing stories from the day's adventures while looking out at the mountain views. Downstairs, a fully finished walk out game room,complete with a pool table, rich pine ceilings, and a built in Sonos sound system offers the perfect space for rainy day tournaments or late-night movies.When the weather cooperates, the living space naturally flows outdoors. A newly constructed upper deck keeps you level with the treetops, while a clever dry-ceiling system protects the custom bluestone patio below. Walk to It is a place built for quiet mornings with a mug of coffee, lively weekend gatherings with friends, and immediate access to the best of Vermonts outdoors.Ready to Experience Powder Mill?Properties that offer this degree of privacy alongside direct trail access rarely stay quiet for long. Reach out today to schedule a private tour and see the views for yourself.

Historic Rowen Farm is an extraordinary Vermont country property, where the character of a circa-1812 Federal farmhouse has been preserved with exceptional care and paired with refined modern comfort on 77.68 private acres of reclaimed meadow, woodland and mountain views. Original wide-plank floors, exposed beams, doors, period details and four wood-burning fireplaces speak to the homes history, while the updated kitchen, baths and lighting by Teaselwood Designs provide a refined modern counterpoint.Inside, the home unfolds with an easy, welcoming flow. The renovated kitchen opens to breakfast, dining and living spaces, with abundant windows framing the landscape. Porches and decks overlook meadows and ridgeline views. Mudroom, ski/gear room, laundry and outdoor shower support four-season living.The four-bedroom, five-bath layout is equally suited to quiet weekends or a full house. A first-floor ensuite guest room offers privacy, while a library/office leads to a separate wing with bonus room, 3/4 bath and exterior entrance, creating exceptional flexibility and potential for a private first-floor suite.Outside, the land is as compelling as the house. Reclaimed meadows, restored stone walls, woodland trails, brooks and exposed rock ledge create a private setting for hiking, biking and quiet enjoyment. The meadows are maintained by a farmer, preserving the pastoral setting with ease. A barn/garage with loft and lean-to adds character and storage.A comprehensive 2003 restoration by skilled craftsmen included major system upgrades and a full basement excavated beneath the original house. The town road was relocated to create greater setback and privacy. A four-bedroom wastewater system was permitted in 2022 and a new shingle roof completed in 2026. High-speed fiber internet keeps you fully connected. Offered largely furnished with limited personal exclusions. Just 8 miles from Okemo, with convenient access to Woodstock, Killington and the Upper Valley.

Vermont Mountain Retreat where adventure meets the view.At the top of the mountain, where the air feels a little crisper and the pace of life slows down, this distinctive Vermont log home offers a setting that makes every season feel special. Expansive mountain views stretch beyond the trees and can be enjoyed from the large decks, lawn and nearly every gathering space.The architecture is authentically rustic, with handcrafted log walls, warm wood ceilings, a massive stone fireplace and natural materials throughout. The spacious great room is made for gathering, with soaring ceilings, walls of windows, a dramatic fireplace and direct access to the view-filled deck. A generous kitchen and dining area provide plenty of room for family and friends, while multiple outdoor spaces extend the living well beyond the walls.Outside, the setting feels natural yet cared for, with stonework, mature woods, open lawn and a screened gazebo tucked into the trees. A detached garage/barn adds flexibility and storage. This is a place for adventure without giving up comfort. Ski at Okemo, Stratton, Bromley or Magic Mountain, explore miles of hiking and snowshoeing, ride the VAST trail, or simply step outside and take in the quiet and beauty of the Vermont mountains. At day's end, gather around the fire and watch the sunset over the mountains.Despite the feeling of being away from it all, Weston Village is close by, offering restaurants, shops, theater and quintessential Vermont village life.Rustic, inviting, spacious and unmistakably Vermont, this is mountain living at its best.