luxury houses for sale Windsor County, United States (page 3)

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 shade trees, and natural landscaping. The main floor of the Inn features the professional kitchen, tavern, and dining areas. The second and third floors offer private residential accommodation, including 5 bedrooms, 2 bathrooms, and a beautifully designed open-concept country kitchen that leads to a spacious deck with views of the surrounding hills and fields. The post-and-beam barn has been repurposed as an event venue and short-term rental, with a yoga studio. The main level of the former working barn is open to a height of 36’, overlooked by the expansive hay loft. The barn is large enough to host up to 60 guests for dinner and 100 for casual events. A 2-bedroom building site beside the spring-fed pond has been approved, with additional sites potentially available by reallocating the existing septic system. The location is ideal for ‘glamping’ with nearby Silver Lake, miles of trails, and outdoor recreational activities drawing tourists throughout the year.

Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout. An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors stepping out to a massive deck for entertaining. The kitchen is well suited with top quality appliances, granite counters and maple cabinetry. There is a primary bedroom ensuite, and a guest bedroom, and a study on the main level. Moving downstairs, the expansive spaces offer a variety of options as extended family space, or in-law accommodation. There's a family room with fireplace, a large area for home gym, or play space. Two additional rooms for guest accommodation, a cedar closet, full bathroom, potential for a second kitchen. Outdoors, the property is magical with terraced perennial beds, mature trees and shrubs all selected to attract birds and butterflies. The oversized barn has three bays, a heated workshop/studio with bathroom, and ample loft space for hay/storage. Commercial grade generator, solar array. Lovely trail network lacing through the property. Easy access to Interstate, Woodstock, Hanover NH, skiing, golf and recreation.

Located in the heart of Sheddsville-West Windsor's earliest settlement, this lovingly stewarded historic Greek Revival Farmhouse imbues the true character of the Vermont vernacular. Improved over the centuries to accommodate modern living, all while preserving the period detail and charm with original pine plank floors, 6/6 sash windows and hewn beams. The home was well built of solid and sound plank construction, providing insulation throughout. The beautiful Great Room addition is anchored by a handsome wood burning fireplace with custom cherry mantel and connects to the exterior spaces through French doors stepping out toa covered porch and a spacious deck overlooking a sweeping level lawn, mature maple trees, established perennial beds, and a firepit at the edge of a four-season stream. Open concepts eat in kitchen with farmer sink and butcher block counters, formal dining room, library- TV room, study with a half bathroom. Two mudrooms complete the main level. Moving upstairs, there's a generous primary bedroom ensuite with a wood stove, a laundry room, three additional bedrooms and a shared bathroom. Leased Tesla back up battery provides peace of mind in the event of a power outage. The ample three-bay barn can be used as parking, equipment storage, workshop, or for farm animals. Extensive dirt roads, and trail systems (ideal for equine interests, hiking, cycling) are just outside your door. Easy access to all recreation, Interstate, Woodstock, Hanover NH. 2.25 Hours to Boston. 4.5 hours to NYC.

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, and significant upgrades and improvements throughout.

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.

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5-bedroom, 4-bathroom extended cape styled home was renovated approximately 15 years ago with handsome hard wood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the French doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom bookshelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garages and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

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. Formal living spaces flow seamlessly into a richly appointed bar and billiards room and onward to a spectacular library, where exquisite millwork and tailored lighting create an atmosphere of quiet grandeur. Each bedroom suite is generously scaled and paired with indulgent ensuite baths. An extraordinary spa offers infrared and salt therapies and opens directly to a heated pool surrounded by nature. Modern systems ensure comfort and security, including radiant heat, central air, water purification, and a whole-house generator. The iconic red barn has been fully restored, with upper-level entertaining and fitness space and a beautifully appointed guest apartment below. Offered as a fully curated turnkey estate, Honey Hill includes exquisite custom furnishings thoughtfully selected to complement the home and setting, allowing for immediate enjoyment. Privately sited behind gates and shown by appointment only, Honey Hill Farm is a world unto itself and legacy in the making.

Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet reflection. Step inside to discover warm, curated interiors where a matching floor-to-ceiling indoor fireplace anchors a cozy great room...an ideal focal point for gatherings and quiet nights in. The custom kitchen is a chefs and designer's showcase making meal prep effortless and stylish. Cute, artful decor and exceptional millwork accentuate every room..every little detail has been considered and executed with eye-popping precision. Natural light pours through thoughtfully placed windows, highlighting textures, finishes, and curated vignettes around nearly every corner. In addition to the four private bedrooms, the special loft above the second-floor den offers a fun sleeping area and great retreat for the kids. Unique sightlines and charming nooks reveal something special at every turn.unexpected architectural details, refined accents, and cozy gathering spots create a home rich in personality and comfort. The floorplan flows intuitively while offering distinct spaces for entertaining and everyday living. Practicality meets luxury with a spacious second garage providing room for toys, workshop space, or secure storage perfect for multi-vehicle households or hobbyists. The gated setting ensures peace of mind and exclusivity, while the manicured wooded grounds offer a serene backdrop and a strong connection to nature. Come see how every corner captures your attention and inspires a sense of wonder at home. This mini-estate is only 10 miles from world-class skiing at Okemo and golf at Fox Run...then enjoy the 5 lakes of Okemo Valley and the nearby VAST trails!

This spacious, well-maintained Gambrel-style home is designed for gracious country living, with a post-and-beam frame that creates large gathering spaces accented by two fireplaces, thoughtful features, and abundant natural light. The private parcel, landscaped with perennials and flowering shrubs, is positioned on a rise overlooking the Barnard Valley towards Woodstock, a few miles south. The location offers a highly desirable balance of privacy and proximity to all resort amenities, shopping, schools, and services, all within a few minutes' drive. A versatile floor plan can be configured with 3 or 4 bedrooms, each capturing views of the surrounding countryside. The superb eat-in kitchen with a breakfast bar is central to the home, surrounded by a dining area and a family room with a well-equipped entertainment center. A separate living room connects to places for celebrating the seasons: a bluestone-paved patio in summer and a greenhouse addition with ideal solar exposure, providing a welcome source of warmth and light in winter. Highlights include updates focused on energy efficiency and modern living, such as high-speed fiber-optic service, an airtight wood stove, a gas fireplace, a heat pump water system, and Tesla batteries, which add resilience. Close to miles of trails, skiing, golf, fishing, and all of Vermont's outdoor attractions.

OPEN HOUSE SAT 13th Noon- 2! Set on 10 private wooded acres with mountain views and open lawn areas, this quality-built Vermont home combines traditional New England design with modern comfort and efficiency. Owned solar panels, radiant heat, a heat pump, fiber-optic internet, and an automatic standby generator contribute to year-round comfort, reliability, and low operating costs. Built in 2008, the home offers wide pine floors, many hand crafted built-ins, abundant natural light, and a warm, welcoming solid feel throughout. A gas fireplace flanked by bookcases anchors the living room, while the dining area opens to a three-season room with a wood stove, extending the summer season.The first floor includes a bedroom, full bath, and laundry, providing the choice of one-level living. The property is exceptionally equipped for hobbies, recreation, and storage, with an attached oversized two-car garage, insulated basement, detached heated studio/workshop, tractor and potting shed. The bonus spaces along with a four bedroom septic permit allow for future expansion. Established gardens and the homes thoughtful design layout create a private courtyard centered around a stone patio and fire pit. Covered porches provide sheltered vantage points for enjoying views, seasonal changes, and the quiet rhythms of country living. Located less than a mile from Weston Village Green, Weston Theater Company, Vermont Village store, and a new coffee shop/bakery in addition to miles of hiking trails in the Green Mountain National Forest. The property also offers convenient access to Bromley, Stratton, Magic, and Okemo ski areas and nearby access to VAST trails. A handsome Vermont property equally suited for year-round living, a Vermont getaway, or a work-from-home lifestyle. Video to come. All measurements approximate.

Constructed in 2025 and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic floating staircase leading to the loft area. Red oak flooring runs throughout. The open concept kitchen is suited with top quality appliances, and a center island with a rich walnut edged yellow birch countertop. The first level Primary ensuite has a dressing room with laundry, and bathroom with a walk-in shower and soaking tub. Up the stairs, there's a spacious area for TV Room, or office and a guest bedroom. The walk-out lower basement level is spacious with high ceilings- perfect opportunity for future expansion. The home connects seamlessly to exterior spaces with astone terrace and a screened porch, both situated to highlight the lovely pastoral views to Mt Ascutney, and beyond. State of the art mechanicals with central AC. Convenient to trail network, all recreation, Woodstock, Hanover NH and Interstate.

High Shelter Farm offers the ultimate Vermont lifestyle on 271 extraordinary acres of fields, forests, and breathtaking views. Once a working farm, this remarkable property features over six miles of professionally designed trails by John Morton of Morton Trails, providing year-round recreation for cross-country skiing, snowmobiling, ATV adventures, hiking, and exploration. Direct access to Vermont's VAST trail network makes this a true outdoor enthusiast's paradise.The meticulously maintained 4,500+ sq. ft. home is perfectly positioned to capture spectacular views of Mount Ascutney and the White Mountains of New Hampshire. Floor-to-ceiling windows fill the living room with natural light and showcase the surrounding landscape. Recent updates include, newly painted interior, beautifully renovated bathrooms and refinished hardwood floors. The home offers four bedrooms, a spacious eat-in kitchen, formal dining room, and inviting gathering spaces throughout. An owned, fully paid-for net-metered solar system transfers with the property, helping power the home while enhancing energy efficiency and long-term value.A permitted one-bedroom accessory apartment with private entrance and patio provides flexibility for guests, extended family, or rental income. Outside, an inground gunite pool and gazebo create the perfect setting for summer entertaining. The recently built barn, now an exceptional event space, has hosted family weddings and gatherings while honoring the property's agricultural heritage.Ideally located near Hanover, Dartmouth, Woodstock, Crown Point Country Club, area ski resorts, Hartness State Airport, and the Upper Valley, High Shelter Farm is a rare opportunity to own a property that truly embodies the best of Vermont livingwhere recreation, sustainability, privacy, and natural beauty come together in one extraordinary setting. Available w/ less acreage see MLS 5096180 OPEN HOUSE. SATURDAY JUNE 27TH 1PM-4-PM AND SUNDAY JUNE 28TH, 11AM TO 2PM.

High Shelter Farm offers the ultimate Vermont lifestyle on 64.64 extraordinary acres of fields, forests, and breathtaking views.. Direct access to Vermont's VAST trail network makes this a true outdoor enthusiast's paradise.The meticulously maintained 4,500+ sq. ft. home is perfectly positioned to capture spectacular views of Mount Ascutney and the White Mountains of New Hampshire. Floor-to-ceiling windows fill the living room with natural light and showcase the surrounding landscape. Recent updates include, newly painted interior, beautifully renovated bathrooms and refinished hardwood floors. The home offers four bedrooms, a spacious eat-in kitchen, formal dining room, and inviting gathering spaces throughout. An owned, fully paid-for net-metered solar system transfers with the property, helping power the home while enhancing energy efficiency and long-term value.A permitted one-bedroom accessory apartment with private entrance and patio provides flexibility for guests, extended family, or rental income. Outside, an inground gunite pool and gazebo create the perfect setting for summer entertaining. The recently built barn, now an exceptional event space, has hosted family weddings and gatherings while honoring the property's agricultural heritage.Ideally located near Hanover, Dartmouth, Woodstock, Crown Point Country Club, area ski resorts, Hartness State Airport, and the Upper Valley, High Shelter Farm is a rare opportunity to own a property that truly embodies the best of Vermont livingwhere recreation, sustainability, privacy, and natural beauty come together in one extraordinary setting.Available with more acreage see MLS 5096178.OPEN HOUSE. SATURDAY JUNE 27TH, 1-4PM AND SUNDAY JIUNE 28TH 11-2PM. ALL ARE WELCOME!

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.

Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details wide plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well suited for both everyday living and hosting. Originally operated as a bed and breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy.The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermonts changing seasons.A guest house and dedicated woodworking barn add to the propertys appeal, offering flexibility for hosting, hobbies, or creative pursuits.Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builders attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design.Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle.

You immediately become aware of the very special nature of this property the moment you turn onto the tree-lined driveway winding to the top of a mild grade where the home is perfectly sited. The barn garage section was built in 2010 and the main residence was added in 2019. The many features of this house make it a perfect primary residence or a welcoming vacation retreat. Open format kitchen-dining-living area with an artfully crafted stone wood-burning fireplace as the centerpiece of this main living area. An adjoining three season room off the dining area enhances the overall livability. Features almost too numerous to mention include: a main level primary bedroom suite with walk in closet and bath with a large fully tiled walk in shower; well-designed mudroom with crafted built-ins; there is a separate adjoining wing with two bedrooms, a large bright sleeping loft, a second full sized kitchen, a sitting area and a three-quarter bath; at ground level there is an expansive bright full walk out basement; a heated oversized two car garage; a stone patio and firepit overlooking a mountain view; an outside shower and an automatic propane generator. The location is perfect, being close to Barnard General Store and Silver Lake, a short drive to Woodstock and an even shorter drive to Saskadena Ski area and all the amenities of Teago.

Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake in scenic Barnard. The main residence features an airy great room with vaulted ceilings, warm wood accents, and expansive windows that invite natural light and frame peaceful views. Thoughtful design and quality finishes, including granite highlights, shine throughout.Enjoy outdoor living from the screened porch, covered porch, or open upper deck, ideal for entertaining or quiet moments. Each bedroom offers the privacy of an ensuite bath, including a serene suite located separately above the garage, perfect for guests, remote work, or added flexibility. A convenient powder room and strong rental history add further appeal.The Post and Beam barn/studio offers inspiring space for creative pursuits, a home business, or potential conversion to guest quarters or an accessory dwelling. Mature perennial gardens, open grounds, and ample parking enhance the charm. Steps from the Appalachian Trail and nestled along a scenic route, this unique offering blends Vermont tranquility with exceptional versatility.

Imagine living in an 1806 home on a Vermont green. Located in the heart of the Green Mountains in the quaint town of Rochester, along the scenic Route 100 corridor. The property is currently a classic Vermont Inn with a chef-owned restaurant and tavern with lovely accommodations. Easily refurnished for private use. The home sits atop the Rochester Green. The village features galleries, shops, and seasonal recreation venues all within walking distance. Prominently featured in the town is the Ridgeline Outdoor Collective which provides backcountry trail opportunities for skiers, hikers, and mountain bikers. As you walk out the front door of the home the first thing you see is the picturesque Rochester Green and gazebo which holds summer concerts and local farmers markets. The Huntington House consists of six eclectic decorated rooms with private baths. The in-law quarters are conveniently located on the second level with a large farmers porch to enjoy afternoon cocktails or your morning coffee gazing at the mountain vistas. Come and explore Rochester, Vermont and experience the lifestyle it has to offer and view this unique opportunity.

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation.This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway.A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons.This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

Spacious Hawk Resort Home with Scenic ViewsEnjoy the perfect blend of comfort, space, and mountain charm in this inviting Hawk home. Designed for family gatherings and entertaining, the generous open-concept living area features a beautiful fieldstone fireplace and updated greenhouse windows that bring in natural light and picturesque views.The primary suite offers a cozy fireplace, private bath with a whirlpool tub, and sliding glass doors leading to a private balcony. The second bedroom and bunk room share a full bath.The lower level provides even more living space, with a spacious family room that opens onto a deck with a hot tub, a full bath with a sauna, and an additional bedroom. Pine floors flow throughout the home, adding warmth and character.Located between Okemo and Killington and close to area lakes.