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

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.

Tucked away on a quiet road in Hawk Resort, this charming 3-bedroom, 2-bath mountain retreat offers privacy, warmth, and easy access to Vermont's best four-season recreation. Just under 1,300 square feet, the home is thoughtfully designed to make the most of its inviting spaces, with random-width pine floors, a classic fieldstone fireplace, and abundant windows that bring in natural light and views of the surrounding woods.The open living area flows to a spacious deck, creating the perfect setting for morning coffee, evening gatherings, or simply enjoying the peaceful natural surroundings.Ideally located halfway between Killington Resort and Okemo Mountain Resort, you'll enjoy convenient access to skiing, golf, hiking, mountain biking, and endless outdoor adventure. Nearby lakes offer swimming, kayaking, and fishing, while the charming village of Woodstock is just 30 minutes away for shopping, dining, and exploring.Showings start 8/4.

Enjoy one level living in this very well-maintained home. Part of the Quechee Lakes community with all its' amenities, the property is perfect as a second home or a primary residence. The lovely deck with surrounding perennial gardens is the perfect place for enjoying an afternoon drink or a morning coffee. Large windows and multiple access to the outdoors provide lots of light inside. The woodburning fireplace offers a cozy spot to relax on winter evenings. Situated within a short drive to the Upper Valley with everything it has to offer as well as being just minutes from the historic town of Woodstock Vt. 2 1/4 hours to Boston and 5 hours to NYC. Sold mostly furnished.

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

Welcome home to this serene piece of Vermont paradise! The property offers an escape to a privately sited cape home featuring 3 bedrooms, 2.5bathrooms with covered and open outdoor entertaining spaces both overlooking an exclusively owned, spring-fed, swimming pond and long-range pasture views - all enveloped by mixed forest land of hard- and softwood. Inside the home gleaming hardwood floors are throughout, a central wood stove provides cozy warmth in the colder seasons to the open cathedral dining and living space. A kitchen with granite countertops, ample storage, and a center island ensure prep space for large and small gatherings. The main level is outfitted with direct entry from the attached garage, a laundry room, powder room, living/dining room, kitchen, and primary ensuite with direct access to the yard. Upstairs 2 additional bedrooms, a full bathroom, cedar closet, and plenty of storage make primary or guest living convenient. The property is further benefitted by a separate, fully outfitted and compliant commercial kitchen which could be utilized for agricultural or other value-added product processing, or repurposed as a guest cabin, studio, or home office. An owned solar array and whole-house generator supply sustainability and reliability while the neighboring 500 acres surrounding the property add insulating privacy and tranquility.

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!

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.

Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication and functionality. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980’s, providing a great room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef’s kitchen, all located on the main level. There is an au pair suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and award winning gardens.

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 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.

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 mid-level includes the spacious primary suite with private balcony and a large bath with double vanity, jetted tub, and separate shower, along with a bunk room, additional bedroom, and full bath.The lower level offers another bedroom, two more bunk rooms, a fully renovated bath, laundry area, and a family room with wet bar and sliders leading to the hot tub deck. Fresh paint, updated lighting and fixtures, accent walls, and new furnishings throughout complete this move-in ready retreat, ideally located between Killington and Okemo.

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.

Nestled on a 3-acre private lot at Hawk Resort in Vermonts Lakes Region, this expansive custom residence offers an exceptional mountain retreat. Thoughtfully designed across four levels--each accessible by elevator--the home provides outstanding separation of space, perfect for hosting family and guests.Designed by architect Robert Carl Williams, the home showcases signature craftsmanship, including soaring windows that frame mountain views, a striking stone fireplace, custom built-ins, cedar closets, and classic pine floors.The residence features six generously sized bedrooms, each with its own sitting area. Five bedrooms offer private en-suite baths, while the sixth-designed as a bunk room-as convenient access to a full bath just across the hall.Ideal for entertaining, the home includes a spacious dining room with scenic views, a large living room, game room, and a lower-level family room--providing inviting spaces for relaxation and recreation.Perfect for gatherings and well-suited for rental opportunities, this remarkable property combines privacy, comfort, and timeless Vermont charm in an unbeatable mountain setting. Located halfway between Okemo and Killington in the lakes region.Roof is at end of life and will need replacement. Driveway in need of repair. Sold as is.

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, youll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study.The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the fire pit beneath star filled skies, surrounded by the natural beauty and privacy of the property.A standout feature is the remarkable multi-level 55 x 40 barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use.Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small town charm that make Vermont so special.

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.

Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic.In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use.Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, it is conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow.This versatile property allows for multiple avenues of income - whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless.Don't miss your chance to own a piece of this thriving community.