luxury houses for sale Chester, United States

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.

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.

Nestled in a postcard-perfect setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. 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 cabinetryperfect 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.

Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct access to the VAST snowmobile system. The 10,062 sq ft timber frame main house is anchored by a soaring two story great room with a dramatic stone fireplace and an open chefs kitchen featuring double appliances, a Viking 60 inch cooktop and a wood fired pizza oven. A cozy loft and a library provide serene reading nooks. The main level includes a distinctive 2 bed, 2 bath primary suite, plus six additional bedrooms and five baths for family and guests. Onsite amenities include a home gym, media and game room, outdoor art installations, paved driveways and six garage bays. The multi building compound consists of a guesthouse with private office, a heated writers cabin with panoramic view of the Connecticut River Valley, an equipment barn and woodshed - everything needed for comfortable year round living, family retreats, or events. Enjoy hiking, snowshoeing, wildlife viewing and a gravity fed 50 tap maple syrup operation all in a private setting to share with family and friends. Watch the award nominated video tour to see why Moosewalk Lane delivers the quintessential Vermont experience.

Set in the highly desirable South Hill Estates, this exceptional property pairs privacy with an unbeatable location just minutes from Okemo Mountain. Surrounded by nearly five acres, the home enjoys sweeping mountain views and a beautifully open landscape that invites year-round enjoyment.The yard is a true highlightoffering plenty of space to relax, entertain, and play. A picturesque pond becomes the centerpiece in every season, perfect for summer afternoons by the water or winter skating and hockey under the open sky. As the day winds down, take in stunning sunsets over the pond with Okemo Mountain as your backdropan everyday experience that never gets old. A large deck overlooks the scenery, while a patio with a hot tub creates the perfect spot to unwind after a day on the slopes or trails. With access to nearby snowmobile trails and only a short drive to the mountain, this setting is ideal for outdoor enthusiasts.Inside, the fully furnished home features over 4,000 square feet of thoughtfully designed living space. The main level showcases rich cherry hardwood floors, a well-appointed kitchen with premium stainless steel appliances, granite countertops, and custom cabinetry, along with inviting spaces for gathering and entertaining. Upstairs, the generous primary suite and additional bedrooms provide comfort and flexibility, while the lower level offers a dedicated home theater for relaxing after a day outside.An oversized attached garage provides ample room for vehicles, gear, and recreational toys, adding more convenience to this four-season retreat. The large Amish shed provides even more storage. This location and setting can't be beat. Don't miss out!

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!

If you are a skier, this is your hop-on-the shuttle to Okemo location. If you want to park your car and walk to restaurants and shops, this is a great home base to scoot out from. If you want to generate rental income, this is a property that can allow you to have your cake and eat it too. An easy keeper, without a lot of landscape to take care of, this large residence has hardwood floors and handsome antique details. The main and second floor each offer three bedrooms, two baths, kitchen, and, if needed, separate entrances. Recent improvements include a large enclosed hot tub room and a new heating system. The third floor features a play room, another bath and tons of bonus space. Lots of flexibility for buyers who seek generous space for extended family, guests or rental income. A great locale for your next mountain get-away!

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.

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.

Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly spacious rooms perfect for entertaining and family gatherings. Wide pine floors, antique fireplaces, and original glazed windows add warmth and charm throughout. The main level features a large primary bedroom suite, while four additional bedrooms and a full bath upstairs provide plenty of space for guests. A cozy recreation room with a grand fireplace or the sauna is perfect for apres-ski evenings, and a separate dining building offers a private space ideal for hosting dinners or working from home as a dedicated office or studio. Outdoors, enjoy peaceful walks through the forest along an old logging road, fish or relax by your own large private pond, and take in the serene beauty of the countryside. A detached 3-car garage adds extra convenience and storage for outdoor gear or snowmobiles. Just a short drive from top ski resorts and year-round activities including hiking, biking, and nearby lakes, this Vermont farmhouse is the perfect mountain retreat.

This impeccably orchestrated cottage style contemporary home was crafted by Ennis Builders in 2006 with an eye to meticulous detail. The sweeping cherry spiral staircase, beautiful stonework and superior fit and finish imbue a quality of workmanship that reflects throughout the home. The main level features an open-concept kitchen with maple butcher block counters, and quality stainless steel appliances, a dining area with a bank of Pella windows providing plenty of natural light throughout the day. The living room is anchored by a fieldstone fireplace designed and built by master stonemason, Hector Santos flanked by custom cabinetry. There isa guest bedroom/office, and ¾ bathroom. Moving upstairs, the generous primary suite has a walk-in closet and luxury spa bathroom. Watch sunsets from the west facing Juliet balcony. The basement level has laundry/utility room with excellent quality Viessmann boiler and heated two car garages. Central vacuum, radiant and baseboard heat. Mini split to cool those hot summer days. Bamboo floors run throughout main floor, and cherry on second level. Tranquil, private end of road location with sweeping westerly views over an expansive open field. Proximity to State Forest for hiking, 35 miles of biking trails on Mt Ascutney. Easy access to Interstate, Woodstock, and Hanover NH, and all recreation

Charming Vermont Ranch on 3.6 Acres with Stunning Mountain Views.Welcome to your peaceful retreat on desirable Holden Hill Road in Weston, Vermont. This beautifully maintained 3-bedroom, 2-bathroom ranch-style furnished home offers 1,809 square feet of thoughtfully designed living space, perfectly situated on 3.6 scenic acres with breathtaking mountain views.Built in 2019 with exceptional attention to detail, this home has been meticulously cared for and feels like new. The open-concept layout provides a warm and inviting atmosphere, ideal for both everyday living and entertaining. A cozy gas fireplace anchors the living area, creating the perfect spot to relax and unwind while enjoying the natural beauty just outside your windows.The spacious kitchen flows seamlessly into the dining and living spaces, while large windows bring in abundant natural light and showcase the surrounding landscape. The primary suite offers comfort and privacy, complemented by two additional bedrooms perfect for guests, family, or a home office.Attached to the house is a finished, insulated and heated garage, so no more clearing ice or snow off your car.Step outside to enjoy your expansive propertywhether you're taking in the mountain views, gardening, or simply enjoying the tranquility of Vermont living, this property offers endless possibilities. Property also includes a whole house back up generator, heat pump split systems provinding heat and A/C (in addition to the baseboard heating)

Views of Mt. Ascutney from this well cared for contemporary home that has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy flow. The charming kitchen leads into a spacious dining room with fireplace. The living room with stunning fireplace leads out to a large deck for outdoor dining. Off the living room the cozy family room features a wall of built-in bookcases. The downstairs bedroom complete with private bath opens onto the spacious screened in porch. The primary bedroom is upstairs. It features a built-in king-sized bed with drawers for extra storage, walk in closets ,and full bath. also on the second floor is another bedroom and bath with walk in shower. The grounds of mature gardens, antique apple trees , blueberry, raspberry bushes ,and original stone walls that border the north and east boundaries create a magical setting. There is ample land to add a garage. Easy access to the Upper Valley with all of the amenities including shopping , Dartmouth College , and world class Dartmouth Medical Center. Woodstock, named by many magazines one of the prettiest small towns in America is less than 25 minutes away.5 hrs. to NYC 2 hrs. to Boston.

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!

Privately sited at the end of a quiet dead end road on beautiful Mt. Ascutney, this cozy 2 BR, 2 BA Chalet style home is an ideal-low maintenance vacation home, or an efficient starter. LR/DR with cathedral ceiling anchored by a sweeping fieldstone fireplace, with woodstove insert; and a spiral staircase leading to aloft perfect for your home office. Kitchen with built ins, and updated appliances. A 3/4 BA further completes the main level. Two bedrooms, full bath and laundry on walkout lower level. Miles of trails for hiking and biking just outside your door, and a short stroll to the year-round recreation and festivities at Ascutney Outdoors. This sweet Chalet is a great opportunity! Most furnishings are available, with a few exceptions. Off peak electric radiators provide heat. Subject to standard ROFR.

Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views.Upstairs, you'll find two bedrooms and a separate office, sharing a full bath. The property also includes a two-car garage with a convenient studio apartment and private bath, ideal for guests. Enjoy direct access to the water with a unique floating dock, perfect for kayaks, paddle-boards, and simply taking in the magnificent scenery.This home is designed to accommodate a life of both leisure and adventure.

Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection.Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chefs kitchen, sun-filled all-season room, and a cellar tavern and game room create spaces that feel welcoming in every season. The separate two-bedroom guesthouse offers additional flexibility for hosting family and friends after long days spent exploring the mountains and surrounding countryside.From winter mornings skiing Stratton, Bromley, Magic, or Okemo to summer afternoons at Lowell Lake, nearby trails, swimming holes, galleries, farmers markets, and outdoor concerts, life here naturally follows the rhythm of Vermonts changing seasons. Evenings return home beside the fire, gathering over dinner, sharing stories, and settling into the quiet beauty of the Green Mountains.Set along scenic Route 11 near the Catamount Trail and just a short drive to Manchester and Weston, this is more than a home. It is a place to create traditions, welcome generations, and experience Vermont at its most timeless and authentic.Floor plans and video tours available online. All measurements approximate.

Prominently and privately sited overlooking the desirable Bible Hill region of West Windsor, this exceptional, meticulous Davis Timber Frame contemporary home has a panoramic view of Mt Ascutney and sweeping views of the New Hampshire hillside and down the CT River Valley. Masterfully crafted with superior fit and finish, the home is anchored by a 36’ cathedral ceiling with floor to ceiling windows, and a commanding fieldstone fireplace. Gourmet chef’s kitchen with excellent quality appliances, custom Alder Wood cabinetry, soapstone counters and hammered copper farm sink. Luxury primary suite on main level with renovated bathroom and walk in closet. Three additional bedrooms on the second level. The finished walk out lower level featuring a billiards room, media room with pellet stove, a wet bar, steps out to a stone terrace with hot tub, tearoom, outdoor shower. Entertain and wow your guests in your very own heated, covered pizza pavilion. The well-appointed post and beam barn has two stalls with direct turn-out and a 3-bay utility garage. Saddle up, or hop on your bike, and ride into the extensive dirt road and trail systems of West Windsor. Easy access to Interstate, Woodstock and Hanover NH.

Perched on a private hilltop and surrounded by nature, this stunning recently renovated home offers over 141 acres of open and wooded land enrolled in Vermont’s Current Use Forestry Program. Thoughtfully designed by Beilman Design, the residence features gracious living spaces filled with natural light and an exceptional floor plan ideal for entertaining. The handsome chef’s kitchen is appointed with high-end stainless-steel appliances, beautiful countertops, and an exquisite walk-in pantry dedicated to preparation and storage. A spacious guest suite includes two bedrooms and a comfortable sitting area, while the finished lower level offers an additional recreation room with a fireplace. The luxurious primary suite features oversized walk-in closets and a gas fireplace that adds warmth and ambiance. Enjoy the peaceful surroundings from the lovely, screened porch or the expansive covered porch overlooking the sweeping lawn and natural landscape. Offering three levels of refined living, the property also includes a large, oversized barn for storage, a generator, and a driveway alarm system. Conveniently located with easy access to GMHA, skiing, championship golf, and exceptional fishing, this private retreat presents outstanding potential for a family compound or countryside getaway. Landscaping plans are available.

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities.This property is subject to an Act 250 permit and enrolled in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

The Hutchinson House, a historic home on the National Register of Historic Places, is a rare find. This beautiful home combines the symmetrical balance of Federal style with the elegant proportion of Georgian design. Featuring authentic Moses Eaton Jr. stenciling, this 1805 home has a rich history and classic New England charm. The property includes over 4,200 square feet of well preserved living space, an attached two car garage with a large heated second story workshop, a striking two-story Victorian horse barn, as well as a screened-in porch and landscaped grounds. The home features beautiful historic details, such as wide pine flooring, period woodwork, and original mantels. The floor plan includes a formal dining room and library, perfect for entertaining, as well as a country kitchen and multiple cozy living spaces for everyday life. Each of the 3 bedrooms has ample light and views of the surrounding land. This property offers a peaceful retreat in a quiet rural setting, just minutes from trails, lakes and nearby village centers. Dont miss this unique property!