luxury real estate for sale Windsor, United States

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 accommodations, or explored for its income-producing rental potential, the flexible layout adapts to a variety of lifestyles.Located in the heart of Brownsville. Just minutes from Mount Ascutney's trails and outdoor recreation, and within easy reach of Woodstock, Okemo, Killington, and the Upper Valley, this is a rare opportunity to own a true Vermont retreat where unforgettable memories are made all year long, with the added flexibility of potential rental income when you're away.

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.

An efficient 2-bedroom chalet located in the foothills of West Windsor. Over the years the sellers have completed a total gut renovation of the interior and exterior of the house. New windows, doors, hardwood flooring, built-ins, remodeled bathrooms and kitchen are just few upgrades to this charming home. A 2-cargarage was added with a large, heated bonus room above, which can be used as a game/exercise room, or converted into extra living space. The main level is an open-floor plan with living, dining, kitchen, primary bedroom and full bathroom. The lower level is outfitted with a walk-out basement along with the main entrance to the home. The finished basement includes a bedroom, full bathroom, laundry room, along with a family room which is heated by a woodstove. Both floors have mini splits for additional heat and air conditioning. The house comes with a full wrap around deck for access to the pool, front sitting deck, and back yard. The barn was originally used as a cider barn which was in disrepair but shored up, insulated and currently being used as a woodworking shop with a wood burning furnace for heat. The new 3-bedroom mound system was installed this year which allows for future growth. The yard around the house and barn are open although most of the 40 acres are wooded with internal trails. Minutes to Brownsville Butcher and Pantry, Ascutney Windsor Trails, 15 mins to Woodstock and I-91 for easy access to the upper valley.

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.

There is something timeless about classic New England character, and this beautifully situated Cape captures that feeling while offering the privacy and space to truly escape. Built in 1990 and set on 42 acres, the property unfolds through expansive fields, peaceful woods, and beautiful views, creating a private sanctuary just minutes from town.The winding driveway through the trees is the first hint of what awaits a sense of arrival and separation from the everyday hustle. Once home, the combination of open land, mature trees, and long-range views creates a setting that feels wonderfully removed, yet remains remarkably convenient.Inside, classic Cape style meets comfortable living, with a warm, elegant atmosphere that feels equally suited to quiet mornings and gatherings with friends. Outdoors, the possibilities are just as appealing. The fields provide room to roam, garden, play, or simply enjoy the changing seasons. A pond on the property was once used for winter skating and adds another layer of New England charm to this special setting.For those who need room for projects, hobbies, equipment, or simply more storage, the detached three bay garage includes a workshop, while an additional barn with traditional sliding doors offers even more covered space. Whether you're looking for a peaceful country retreat, room to pursue your passions, or simply a place where coming home feels like an escape, this property offers an uncommon combination of privacy, beauty, character, and convenience.Open house Saturday 9/5/2026. 1:00-3:00pm

This spacious, bright, impeccably maintained hilltop retreat checks all the boxes, with stunning long-range views to both the southeast and northwest. Open concept kitchen with granite counters, maple cabinetry, pantry, excellent quality stainless steel appliances, and mudroom entry. Private deck and porch for outdoor entertainment. The living room is anchored by a brick wood-burning fireplace, and French doors opening to a generous dining room with an expansive view to the east. Oak plank floors run throughout the main level. Primary bedroom ensuite with huge walk-in closet, and a private deck. There are two additional bedrooms on the main level. Heading downstairs, there’s a spacious media/family room with a wood burning stove, a tiled space ideal for home gym, yoga studio, potting room, laundry room, and utility room with a work bench, storage and state of the art mechanicals. The barn-garage has a lovely one-bedroom-in-law, or au-pair suite, parking for two, and plenty of room for hobbies. Mature flowering trees and shrubs established perennial beds, and a greenhouse. Solar array provides electricity at no cost. Owned Tesla storage batteries in the event of a power outage. Conveniently located within close proximity to Woodstock, Upper Valley, DHMC.

Exceptional opportunity to build in one of West Windsor's most scenic neighborhoods Located amongst some of the finest equine properties in the region with easy access to the extensive trail system for riding, hiking and recreation. The property is encompassed by ancient stone walls and has a beautiful inventory of mature hardwood. 1365' altitude at the height of land offering dramatic south-easterly view potential. Perfect as a horse farm, or a beautiful country home site. Existing storage shed on property. Easy access to Green Mountain Horse Assn, Ascutney Mountain, I-91, Woodstock, Hanover NH, skiing, restaurants, shopping.

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 living where recreation, sustainability, privacy, and natural beauty come together in one extraordinary setting.Available with more acreage see MLS 5096178.

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.

Rare opportunity to own one of the most unique compound properties in West Windsor. "The Dome" and The "Silo House" share a lovely 13.9 AC secluded and tranquil parcel fronting the Willow Brook in the desirable Rush Meadow region of West Windsor with rear access to the extensive local trail system. Beautiful established gardens, and mature plantings. Excellent rental investment potential. Both homes have been extensively renovated. Proximity to Woodstock, Hanover NH, Interstate, skiing and all recreation. "Silo House" is being offered for sale independently with two acres. See MLS #5109223

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.

The property is located on Town Farm Hill Rd, one of the most beautiful ridgeline Vermont roads with long range mountain views to the east and south. At certain times of the day the lighting brings out the true meaning of “purple mountain majesty”. Over the years the seller has acquired multiple parcels to create this beautiful sanctuary setting. The house is positioned to take in the mountain views, spring-fed swimming pond, meadows, and apple orchard. Beautiful rolling fields, stonewalls, acres of forest, and outbuildings are many features of the property. It is surrounded by horse, mountain biking, and hiking trails for recreation. This modest 3-bedroom, 2-bathroom, center chimney Cape with cedar clapboards on 74.83 acres has just been refurbished and is move-in ready. The house could be used as a primary home while building your Vermont dream house, then turned into a wonderful guest house or caretaker’s home. The main level has a spacious country kitchen with an easy flow to the dining and living rooms. Enjoy the views along with Mother Nature while having your morning coffee, evening cocktails or dining on the covered porch overlooking the orchard and pond. Upstairs you find the primary bedroom, full bathroom with laundry, along with two additional bedrooms. The walkout basement is outfitted with a family room, game room, and utility room for the mechanics. The 24’x40’ out building has been used as a workshop, although could be transformed into an animal barn if desired. There is an additional 12’x20’ storage building. Minutes to the village of Hartland, Woodstock, I-91 and the Upper Valley.

Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are plenty of spots for a homesite, a family retreat, or even a simple rustic getaway to relax, recharge, and dream about the future.

A magical Vermont setting, complete with a private pond and visits from a great blue heron. A tree-lined approach welcomes you to this wonderfully open and beautifully proportioned three-bedroom, two-bath log home with desirable southerly exposure.The main level features an expansive open kitchen and a spacious dining room that flows naturally into the family room, where exceptional natural light creates a bright and inviting atmosphere. The cathedral ceiling living room features a lovely bay window. A deck spanning the length of the home provides generous outdoor space from which to enjoy the peaceful surroundings.The lofted upper level includes a bedroom, full bath, and open workspace. The lower level offers a wonderfully private bedroom with direct exterior access. An expansive mudroom entry features a soapstone wood stove and laundry area, along with access to ample storage.Bright, updated baths with tile surrounds, a whole-house dehumidifier, a new roof, excellent stonework, lovely grounds, and an exceptional level of care further distinguish the property. A charming sugarhouse offers flexible space for garden equipment, a workshop, or a childrens playhouse, completing this truly special Vermont retreat.

Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in the early 1800’s. The rooms are spacious, bright and inviting with exposed hand- hewn beams and pine plank floors running throughout. The updated country kitchen with soapstone counters connects to a cozy reading room with bookshelves and wood stove, and a utility/mudroom with ¾ bath, and laundry. The formal dining room offers plenty of space for gatherings. The front to back Living Room is anchored by a woodburning fireplace, and steps out to a private sunroom, and a guest room/office. Moving upstairs, there are four bedrooms and a bathroom. The 18thcentury hip roofed, post and beam English bank barn has a huge, sweeping loft space ideal for parties and entertaining. The lower level can accommodate animals, hobbies or a home occupation. The barn is surrounded by lush green pastures, and rail fencing which lead you to a network of beautiful trails for hiking. A short stroll to The Kedron Valley Inn, KV Pond, The South Woodstock Store, and Green Mountain Horse Assn. A five-minute drive to the Woodstock Village Green. Easy access to Hanover, DHMC, skiing, golf, dining, shopping and recreation.

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms, 4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 10 acres comprise of lovely landscaping around the home and plenty of land for gardens and animals. The 18th century barn and corn crib lend much charm to the setting. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Located only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home!

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx. 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered with stone walls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first-floor primary suite with private bath, vaulted ceilings and new large walk-in closet. Kitchen features Thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertainment on the brick patio or the new east terrace. Enjoy a separate 3-bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

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.

Hart’s Crossing is a home and a haven featuring a custom 21st-century residence and a comprehensively restored Civil War-era guest house, set on418 acres of private land. The property provides a refuge in nature, with a kingdom-sized backyard to explore and adventures that change with the seasons. Located at the end of a town-maintained road, the property is a 10-minute drive from either Woodstock Village or the Upper Connecticut River Valley to access the conveniences and necessities of life, yet a century away from the inconveniences, in a peaceful sanctuary. The airy and light-filled 5-bedroom main residence sits on a plateau overlooking the Ottauquechee and White River Valleys to the east and north, with sweeping views to the south along the Connecticut River through walls of windows. The historic farmhouse has been reimagined as a comfortable 2-bedroom guest cottage, featuring exposed timber framing accented by a modern kitchen and bath, with a screened porch and wide deck alongside a refreshing, spring-fed swimming pond. Nearby is a multipurpose barn with a caretaker’s apartment for farm and recreational purposes. The property is enrolled in Vermont’s Current Use program, intended to help large landowners preserve the working landscape with a professional land management plan and a reduction in property taxes as consideration. There are miles of trails enabling access to the entire property for hiking, biking, snowmobiling, and simply wandering without a watch. At the end of Sugar House Road, you’ll discover the best of today, thoughtfully combined with the timeless values of yesterday.

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.

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 of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter.

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!

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.