628 properties for sale in Windsor County

Rustic character meets modern comfort at this tastefully appointed woodland retreat, built in 2025 and nestled among the trees on 12 private acres. Exposed beams, natural wood ceilings and floors create a warm, inviting interior, with plenty of windows that bring in natural light and views of the surrounding landscape. The open living and dining spaces offer a comfortable gathering place, complemented by a tastefully designed kitchen featuring deep green cabinetry, wood countertops, a tile backsplash, and a stainless steel farmhouse sink. Powered by solar with a whole-house generator backup, this off-grid cabin offers a distinctive opportunity to enjoy Vermont's quieter side. The Lyman Brook winds through the lower part of the land. There is direct access to the Vermont snowmobile trail network (VAST) with a two car garage to store all your toys. Enjoy cross-country skiing and hiking right outside your door, and five ski mountains within a short driving distance. The nearby villages of

Welcome to this beautiful 3-bedroom, 3-bathroom Gambrel in the picturesque Quechee Lakes Association. This house is filled with natural sunlight, beautiful wood floors throughout, and inviting living spaces. The home creates a sense of timeless charm and elegance. Thoughtfully designed for comfortable living and effortless entertaining, this home welcomes you from the moment you step inside. Upstairs, the spacious primary suite offers a relaxing, private retreat. Two additional bedrooms and a full bathroom upstairs offer comfort and flexibility for family, guests, or a home office. Mini-split systems throughout the bedrooms and living spaces provide year-round comfort, keeping the home cool in summer and warm in winter. The well-appointed kitchen is perfect for everything from quiet mornings with coffee to evening gatherings with family and friends. This space makes everyday living a pleasure, with a comfortable, practical layout for preparing meals and entertaining. A beautiful dining

Honey Hill Farm is a rare and distinguished Vermont estate encompassing 264.4 extraordinary acres of pastoral beauty, panoramic mountain views, and an unrivaled network of private trails, with an additional contiguous 42.6-acre parcel available for purchase. More than a luxury property, Honey Hill offers the experience of a private park, with nearly 10 miles of trails winding through forests, open meadows, cascading brooks, waterfalls, and around a spring-fed pond. Whether for hiking, cross-country skiing, horseback riding, mountain biking, or quiet exploration, the land offers a seldom-found level of privacy and recreation. The main residence has been masterfully reimagined through a full-scale renovation, blending timeless craftsmanship with modern luxury. At its heart lies an expansive gourmet kitchen with custom marble finishes and bespoke detailing. A four-season room with floor-to-ceiling glass doors dissolves the boundary between indoors and the breathtaking landscape beyond. Fo

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

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 highlight-offering 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 backdrop-an 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

Great opportunity to own a small cape in The Grove with the ability to expand. This is a 2 bedroom, 2-bath cottage all on one level with the second floor open and unfinished for the next owner to create their own personal space with endless possibilities. This is a low maintenance home with mini split air conditioning, a generator and perennial gardens. Open floor concept for ideal entertaining with an abundance of light throughout. Primary bedroom has an en-suite bathroom with soaking tub. Another guest bedroom with 3/4 bath also on the first floor. Quick walk to the Barnard General Store for breakfast or to Silver Lake for swimming and canoeing. This property does not have direct access to Silver Lake. Just 12 minutes to historic Woodstock for all amenities, shopping, dining, golf and skiing. This is a turn-key affordable home the premiere village of Barnard. Building inspection available

One-of-a-kind Lake Rescue sanctuary with 179 feet of shoreline, stone walls, perennial gardens, apple trees, and a sprawling flat lawn perfect for games and gatherings. Offering exceptional flexibility, this special setting on 4.35 acres has the potential to become a family compound, multi-generational retreat, or income-producing investment. A 3-bedroom septic permit is already in place, creating the opportunity to build an additional home along the water and establish a legacy for generations to come. Inside, pine floors run throughout the home, complemented by a chef's kitchen and a deck with hot tub just outside the sliding doors. Spend summer days swimming, boating, and relaxing by the dock, with a lakeside shed to store all your gear. The property also features a large barn with abundant storage and a one-bedroom apartment over the garage, ideal for guests, extended family, or rental income potential. A rare Lake Rescue retreat with endless possibilities, all just minutes from Ok

This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The soothing music of the water rose to a crescendo in

Enjoy the best of both worlds at this country home. So close to the slopes with the Okemo Shuttle yet privately tucked into a wooded, one-acre country setting. The heart of the home is a spacious, light-filled great room featuring soaring ceilings, skylights, hardwood floors, an open loft and an impressive floor-to-ceiling stone fireplace. The fully renovated kitchen offers abundant cabinetry, stainless steel appliances and an oversized island with plenty of room for gathering. Five bedrooms are comfortably arranged over three levels, including a main-level primary suite, two upper-level bedrooms connected by a new Jack-and-Jill bath, and two lower-level bedrooms with an additional new shared bath. The lower level also features a recreation room, providing plenty of space for family and guests. Outside, a generous deck surrounded by trees creates a private setting for relaxing and enjoying the hot tub. A separately accessed bonus area offers several possibilities as a workshop, home of

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Privately sited on 42 pastoral acres, this gracious Vermont country retreat offers approximately 4,000 square feet surrounded by expansive lawns, perennial gardens and two picturesque ponds. The four-bedroom, four-bath residence is ideal for comfortable living and entertaining, with red birch floors, nine-foot ceilings and wonderful connections to the outdoors through multiple screened porches, a sunny deck and covered porch. At the heart of the living room is an impressive wood-burning fireplace, handcrafted with stone gathered from the property and finished with a custom cherry mantel. Three additional gas fireplaces add warmth throughout the home. The spacious kitchen is ready for a crowd, with Vermont soapstone countertops, a butcher-block island, three sinks and three dishwashers. The main-level primary suite enjoys its own gas fireplace and screened porch. Upstairs are two additional bedrooms, two baths and a handsome library with built-in shelving, fireplace and access to a balc

Classic Alpine Chalet with Guest House and Amenities. Embrace the Vermont mountain lifestyle in this four-season retreat, where classic 1970's alpine design meets the beauty of its natural surroundings. More than a private retreat, this property is a gateway to the many pleasures of Southern Vermont, from skiing and snowshoeing in winter to hiking, tennis, gardening, farmers markets, antiquing, galleries, Manchester shopping, the Weston Playhouse and Northshire Bookstore throughout the year. Set on a picturesque property with a private pond, tennis court and delightful gardens, the estate offers peace, privacy and plenty of opportunities to enjoy the outdoors. The main residence was designed to bring the outdoors in, with dramatic cathedral ceilings and expansive walls of glass that fill the rooms with light and frame views of the mountains, gardens and woods. A cozy den with brick fireplace is a comfortable spot to unwind, while a game room offers space for entertaining. There are thr

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace

Perched above Weston's coveted Dale Road in a private woodland setting, this handsome expanded cape was designed by Raymond Austin, architect of the famed Weston Playhouse. The home exudes graciousness and attention to detail in a living space that offers both cozy warmth and a light and open feeling. Surrounded by country gardens and with a south facing deck and mountain views, the property is a slice of Vermont heaven both inside and out. The first floor has a welcoming mud room with laundry and powder room, a relaxed family room/kitchen with wood burning fireplace, walk-in pantry, and deck access, a formal dining room and spacious living room with gas fireplace, and a private bedroom with ensuite bath. The second floor includes 2 guest bedrooms, one currently used as a home office, sharing a full bath, plus a primary suite with a large bedroom, ensuite bath, and walk in closet. The full dry basement offers plenty of storage space, and the attached 2 car garage will be a special comf

The best of Quechee Lakes living, with room to gather, unwind, and enjoy Vermont in every season. This inviting three-bedroom contemporary offers a private wooded settings, generous indoor and outdoor living spaces, and access to the exceptional recreational and social amenities of the Quechee Club. Equally appealing as a year-round residence or Vermont getaway, the home features an open-concept main living area designed for gathering, with a covered porch and extensive decks that invite easy indoor-outdoor living. Ample lawn, surrounding woodland, and protected greenbelt space create a wonderful sense of privacy, while the hot tub is the perfect retreat after a day of skiing, golf, or exploring the trails. Three comfortable bedrooms are complemented by a newly finished lower-level bonus room, offering flexible space for overflow guests, a home office, playroom, or recreation. Recent improvements include a new roof and newly paved driveway, adding to the home's move-in-ready appeal. Ow

This unique one-of-a-kind property will inspire your creativity. The Silo House is located on a tranquil, private lot in the desirable Rush Meadow region of West Windsor with frontage on the Willow Brook and rear access to the local trail system. There are two bedrooms, a LR/DR combination and a large, shaded deck overlooking the brook. Perfect for full-time living, or a great second home opportunity. Shared ROW access to be re-routed upon sale

An irreplaceable 27-acre land holding on Okemo Mountain, offering one of the most unique ownership opportunities in southern Vermont. With direct access to the Mountain Road Trail, acreage bordering the Sidewinder Trail, and Coleman Brook defining the northern boundary, this extraordinary property occupies a setting that is virtually impossible to replicate. Selective clearing could reveal sweeping easterly mountain views. Whether your vision is a legacy family compound, an exceptional private mountain retreat, or a long-term investment, opportunities of this scale and location rarely become available. Think beyond the existing improvements and imagine what 27 trailside acres on Okemo Mountain could become. The residence offers three levels of living space plus a basement and includes five marble bathrooms. The home has been vacant, vandalized, and is in significant disrepair, requiring extensive restoration. The condition of all utilities and mechanical systems is unknown, and the pro

This lovely, updated Mill Run end unit offers two bedrooms, one and a half baths, and a warm, inviting setting surrounded by mature hardwood trees. Southeasterly exposure fills the home with natural light, while the wooded surroundings provide privacy, spectacular fall color, and seasonal views of the Ottauquechee River.The open and airy main level features an expansive cathedral-ceiling living and dining space with large windows and direct access to the deck. The upgraded kitchen opens naturally to the living area and includes a breakfast bar with seating for two, attractive pendant lighting, and abundant warmth and character.Both bedrooms enjoy peaceful wooded outlooks, and the primary bedroom opens directly to a private outdoor space. Meticulously cared for and comfortable throughout, this special end unit is just a short walk from the Quechee Covered Bridge, Simon Pearce, and the heart of Quechee Village

Located at the end of a private road, this tranquil oasis is the perfect escape suitable for full or part time living. The Classic Cape home imbues the idyllic Vermont vernacular farmhouse with a spacious wrap around porch seamlessly connecting interior with exterior spaces. The main level has the ideal footprint for entertaining or daily life. The country kitchen is well appointed, and spacious with plenty of workspace and cabinetry. The living room is centered by a beautiful antique cast iron woodstove, with separate spaces to gather. The heated sun porch has windows overlooking the fruit trees and berry patches. A 3/4 bath completes the main level. Moving upstairs there are three bedrooms and a shared bath. The bonus separate 2 bedroom in law suit is perfect for extended family, or as an income producing rental. One car garage, and a great old barn for hobbies or equipment storage, or to house farm animals. The 10 AC parcel is laced with trails for adventure. New standing seam roof,

Some homes just feel like magic! Set amid Vermont's picturesque rolling pastures and scenic walking trails; this exceptional property exists in perfect harmony with its natural surroundings. A private woodland trail invites peaceful strolls through the forest, while the soothing sound of the babbling brook winding through a historic 1817 stone sluiceway creates a truly enchanting setting. Mature trees and beautifully landscaped gardens provide a private outdoor sanctuary and a seamless connection to nature. Adding to the property's quintessential Vermont charm is a beautifully restored 1830's barn. Rich in history and character, the barn offers abundant space for storing vehicles ATVs recreational equipment, and more, while enhancing the estate's timeless country appeal. Large windows fill the home with natural light and framed tranquil views in every season. The inviting living room, anchored by a striking fireplace, is the perfect place to gather on crisp Vermont evenings. The though

Spacious Coach Road end-unit condominium offering exceptional privacy and outdoor space in a desirable location at the end of Coach Road on the western edge of Quechee Lakes. The open floor plan is flooded with natural light, while the fabulous kitchen layout flows easily into the dining and living areas. An expanded patio with direct access from the dining room creates a wonderful extension of the living space and an inviting setting for outdoor dining and entertaining. With three bedrooms, three and a half baths, and tile and laminate flooring throughout, the home offers plenty of room for family and guests. The one-car garage provides convenient parking along with additional storage. Overlooking the valley, the property enjoys expansive winter views across the entire valley while maintaining a wonderful sense of privacy. Conveniently located just above the Coach Road pool and tennis courts and within easy walking distance of the Quechee Club, this lovely Quechee Lakes condominium co

Mill Run 1 Condo- END UNIT being offered fully furnished and in very good condition. Excellent rental history for those looking for an investment property when they are not using this unit. The first floor boasts an open floor plan with cathedral ceilings anchored by a wood stove, wood floors and bathroom. Easy access to enjoy the deck with slider doors off the dining area. Extra sunlight with more windows. Lower level consists of 2 bedrooms with a shared bathroom and laundry area. Ready to go. This is a low maintenance unit and has easy access to the Quechee Club amenities, Simon Pearce and all of the Upper Valley amenities. Come take a look!

This spectacular Yankee Barn Post and Beam Home has stunning views from every angle! Custom built in 2006 of the finest materials, this warm and inviting home is in pristine condition. Spacious, sun-filled rooms with soaring cathedral ceilings are perfectly configured for a seamless flow, and plenty of room to sprawl. The great room is anchored by a fieldstone fireplace with a raised hearth of hand-picked local stone. Open concept kitchen with gleaming granite, top of the line Kenmore SS appliances, and a walk-in pantry. Step out of the sunny breakfast room to the Trex deck complete with a propane hookup for outdoor grilling, and a picture-perfect back drop of Ascutney Mountain. Huge 1st Floor Master bedroom with gas fireplace, ensuite bathroom complete with whirlpool tub and custom cherry cabinetry. Finished, walk -out lower level with plenty of room for expansion. Multi-zoned radiant heat and structural insulating panels provide efficient, even comfort. Three Mini splits to provide c

Fully renovated and tastefully appointed with Crate & Barrel furnishings, this turnkey Hawk Ledges condominium offers an easy-care Vermont getaway. Modest in size yet thoughtfully designed, it features two bedrooms, each with a private bath, a welcoming stone fireplace and convenient exterior storage. Explore Hawks extensive trail network right outside your door, swim at nearby Plymouth State Park, or enjoy skiing and golf at both Okemo and Killington. Just bring your hiking boots, swimsuit and skis; everything else is ready for you!

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Set on 18 private acres, Popple Fields is a very special Vermont property one that feels less like a house that was built and more like a home that was lovingly crafted.Built in 1989 by its owner, a true master craftsman, this Williamsburg saltbox reproduction reflects a lifelong appreciation for traditional architecture, fine woodworking, and the quiet beauty of things made by hand. The builder was a skilled Windsor chair maker whose work was featured in Yankee Magazine, and that same extraordinary attention to detail can be felt throughout the home.Inside, the craftsmanship is warm and beautifully understated. Wide plank wood floors, paneled walls, reclaimed beams, layered moldings, and custom woodwork give the rooms an authentic sense of age and character. The house has the gracious proportions and enduring appeal of an earlier era, while offering the comfort and livability of a thoughtfully designed modern home.Originally created as a bed and breakfast. There are inviting spaces fo

This sweet townhouse has a terrific location in Wilder, minutes from Dartmouth College campus, Dartmouth Hitchcock Medical Center, VA Hospital, restaurants, shopping, Advance Transit (The Green Route) and all that the Upper Valley has to offer. Main level is open featuring large living room, spacious kitchen/dining area, views of patio and woods. Appliances include electric range, dishwasher, microwave, refrigerator, washer and dryer. Two generous size bedrooms upstairs, large closets, full bath, and effortless no-step mudroom entry. Pet-friendly, access to nearby trails, facility with coin-operated laundry for oversized items, a meeting room and exercise area. You will love the convenient life style in this desirable Upper Valley community

Enjoy the best of Lake Rescue and the Okemo Valley from this inviting contemporary home with shared lake frontage just a short walk away. Shared with only one other property, the frontage is tucked into a quiet private cove with beautiful lake and mountain views and features a floating dock with deep-water access and room for a boat, along with a grassy beach area-an ideal setting for boating, swimming, or simply relaxing by the lake.Inside, the light-filled open living, dining, and kitchen areas are highlighted by soaring wood ceilings, a dramatic two-story brick fireplace, and a wall of windows that brings the surrounding Vermont landscape indoors. The kitchen features granite countertops and opens easily to the dining and living spaces. Three bedrooms include a spacious primary suite, while the finished daylight lower level provides additional room for family and guests. Recent improvements include new flooring, fresh paint, and an updated bath.Expansive decks wrap around the home,

With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone.The newer addition features an open concept kitchen, dining, and living area anchored by a custom stone fireplace and dramatic floor to ceiling windows framing the mountain views. A sun-filled deck invites morning coffee, summer entertaining, or cozy apr?s ski evenings. The primary suite is a private retreat with its own deck, ensuite bath, walk in closet, and dedicated office.The original wing offers four additional bedrooms, a kitchen, living area, and its own deck, creating an ideal space for guests or extended family. Whether enjoyed as one expansive residence, configured for private guest accommodation

This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic property to others, who can return it to private use or continue serving the community as a center of hospitality, helping to cover the costs of ownership. The Inn features original fireside dining rooms, complemented by a rustic tavern serving both classic and inventive 'pub' cuisine. The professional kitchen has undergone a thorough renovation, increased efficiency and enabling flexibility of culinary styles. Marketing opportunities are limited only by imagination, including the use of expansive lawns for weddings and events in both indoor and outdoor settings among flowering shrubs, mature shad