luxury real estate 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 the heart of Vermonts scenic countryside, this beautiful 27.2-acre parcel offers the perfect setting to build your dream home or mountain retreat. Mostly wooded with over 800 feet of road frontage, the property combines privacy, natural beauty, and easy access to some of Southern Vermonts most desirable destinations.Enjoy mountain and scenic views that provide ideal building sites surrounded by mature trees and peaceful landscapes. Whether you envision a cozy getaway, year-round residence, or recreational escape, this property captures the classic Vermont lifestyle quiet mornings, vibrant fall foliage, outdoor adventure, and four-season beauty.Conveniently located near Okemo Mountain Resort and just a short drive to the charming towns of Ludlow, Chester, and Weston, youll enjoy skiing, hiking, dining, shopping, and quintessential New England charm all within reach. A rare opportunity to own a slice of Vermonts natural beauty.

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.

Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared home-site ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom wastewater permit is already in place, and the driveway has been roughed in, making it easy to bring your vision to life. Whether you're planning a full-time residence or a seasonal retreat, this property is ready for your dream build. Outdoor enthusiasts will love the proximity to the VAST Trails, with access nearby on Dorman Road, while skiers and snowboarders are just 15 minutes from Okemo Mountain Resort. Enjoy easy drives to the charming and historic towns of Weston and Chester, known for their quintessential Vermont character, dining, and shopping. Andover is a truly special place, offering scenic beauty, tranquility, and a sense of escape yet still close to everything that makes southern Vermont so desirable.An ideal setting for your Vermont getaway or year-round home.

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.

UNBELIEVABLE VALUE in a great setting ! Bordering the Ludlow line and set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes a state-approved wastewater permit and access to a community leach field, making it ready for building your dream home. Enjoy convenient access to year-round recreation, including skiing and golf at Okemo Mountain Resort just three miles away. A rare opportunity to create a private mountain retreat surrounded by natural beauty.

A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom guest house. Come build your dream home in the quiet upscale community of Summit Ridge. If you are looking for a premium spot to build with amazing views, come see this parcel!

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!

Lot 9 - This 12.2-acre wooded lot offers potential for long-range mountain views with clearing. Easy access from a town-maintained gravel road.Located just 5 minutes from Ludlow and Okemo Mountain Resort, this property offers both privacy and proximity to year-round recreation and amenities.Lot 9 is accessible via a right of way and abuts the Okemo State Forest.Vermont State Wastewater Permit is needed.

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.

Long-range views of Stratton and Bromley define this 4.86 +/- acre offering in Londonderry, where elevation, privacy, and natural beauty come together in a compelling Southern Vermont setting. The access road and future building site are already roughed in, creating a strong foundation for a thoughtfully designed Vermont retreat.Supported by a State of Vermont wastewater permit for a five-bedroom single-family residence, the property offers the flexibility to create a private home connected to the regions four-season lifestyle. Mountain views, surrounding woodland, and the quiet of the Green Mountains create a setting that feels both peaceful and connected to outdoor recreation throughout the year.Picture mornings with changing mountain light in the distance, winter days spent skiing nearby, and evenings returning to the calm of your own Vermont retreat. The property is positioned just minutes from Magic Mountain Ski Area and the Londonderry Marketplace, with convenient access to Stratton, Bromley, and Okemo Mountain Resorts.Whether envisioned as a modern mountain residence or a timeless Vermont escape, this is an opportunity to create a home shaped by privacy, landscape, and connection to one of Southern Vermonts most desirable year-round destinations.

Top-floor, two-bedroom condo in the desirable Winterplace community with direct slope access and trail views.The open living area features hardwood floors, gas fireplace, a wall of windows overlooking the slopes and a cathedral ceiling that adds light and space. Functional layout with two bedrooms, two baths, and a tiled mudroom entry, AND the ability to add loft space above the bedrooms. Private ski locker.The K Building location is the standout: step outside for immediate trail access and short walk to all community amenities. Winterplace offers a year-round indoor pool with hot tubs and locker rooms, plus seasonal tennis courts, basketball, and a BBQ areamaking this an easy choice for both winter use and summer getaways.

Morning light spills across the meadow, the pond reflects the changing sky, and the Green Mountains rise in the distance. Set on 10.2 acres along a quiet country road near Weston Village, this exceptional parcel offers the rare opportunity to create a Vermont home deeply connected to both landscape and lifestyle.Much of the groundwork has already been completed, including a state-approved five-bedroom septic design, a newly created four-acre meadow, and a spring-fed pond that brings natural beauty and a sense of calm to the property throughout the seasons. Southern exposure, mountain views, and multiple building sites offer flexibility for designing a retreat that feels both private and open to the surrounding scenery. Architectural renderings are also available to help inspire the vision ahead.Adventure and recreation are woven into daily life here. Spend winter days skiing at Okemo, Bromley, Stratton, or Magic, then return home beneath clear mountain skies. Warmer months invite hiking, mountain biking, paddling, and exploration within the nearby Green Mountain National Forest, with snowmobile and cross-country ski trails also close by.Just over a mile away, Weston Village offers a timeless Vermont atmosphere with local dining, the Vermont Country Store, Weston Theater Company performances, and gathering places that give the area its enduring character and sense of connection.Rarely does a ready-to-build parcel combine natural beauty, recreation, and proximity to one of Southern Vermonts most beloved villages so effortlessly. A remarkable setting to shape something truly personal.

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!