628 properties for sale in Windsor County

Experience the best of mountain living at this exceptional custom residence in Hawk Resort, offered fully furnished for a turnkey opportunity. Set on 1.33 private acres with seasonal views of Lake Amherst and Okemo Mountain, this impeccably maintained home offers over 3,500 square feet of thoughtfully designed living space between Okemo's Jackson Gore Base and Killington's Skyship Gondola. Built with an uncompromising commitment to quality, craftsmanship, and energy efficiency, where exceptional construction extends beyond what meets the eye. Carefully engineered for Vermont's climate, every detail was carefully considered, from its superior mechanical systems and premium materials to the care and improvements that have kept the property in exceptional condition. The kitchen, dining area, and great room flow effortlessly together, making it the heart of the home and creating an inviting space where family and friends gather together. The home features soaring cathedral ceilings, expans

Discover classic Vermont living at 74 Moses Pond Road in Weston, set on 11.4 beautiful acres along a quintessential Vermont country road. This warm and inviting three-bedroom home offers a wonderful combination of privacy, character, and convenience in one of southern Vermont's most desirable locations. The property features an oversized barn/garage, providing exceptional space for vehicles, recreational equipment, a workshop, studio, or additional storage. Surrounded by the natural beauty of the Vermont countryside, the setting offers plenty of room to enjoy the outdoors while remaining close to the cultural and recreational attractions that make Weston so special. Enjoy convenient access to the renowned Weston Theater and Kinhaven Music School, along with charming village amenities and year-round activities. Outdoor enthusiasts will appreciate being within easy reach of some of Vermont's premier ski destinations, including Okemo, Killington, Stratton, Magic Mountain, and Bromley. Whe

Quietly sited off a private secluded road, sits a finely hand-crafted family compound featuring 2 buildings on 10.27 acres. The lot features an open yard, gardens, stone walls, woodland trails and nearby brooks. The main house features post and beam construction with sweeping cathedral ceilings, 2 bedrooms, 1.5 baths, a loft, finished lower level, and many custom-built features. The kitchen is well appointed with custom cabinetry and stone counters. A stand-out bonus feature comprises a large detached shop with 2 bedroom in-law or rental apartment above an 1150 sq. foot office/woodworking shop prefect for hobbies or a commercial home business. This property is perfectly sited in close proximity to State Forest for hiking, biking trails on Mt Ascutney, easy access to Interstate 91, Woodstock VT, Hanover NH, Dartmouth, and all recreation

A rare piece of Vermont architectural history, this distinctive chalet was the inaugural home built in the Great Hawk Community. Designed by the renowned architect Robert Carl Williams, this property served as his original model home and office, welcoming prospective buyers and showcasing his vision for the custom homes that were later built on Hawk Mountain. Williams held the property in particularly high regard and chose it to exemplify his signature design style in several architectural books. True to his vision, this home was designed to be one of a kind, with its footings poured directly into the mountain itself. Since 2024, the home has been owned by a New York marketing and advertising executive who undertook an extensive modernization, transforming this architectural gem into a luxurious mountain retreat while honoring its original character. Notable upgrades include radiant heated flooring, a custom designed built-in spiral staircase, all new European-style kitchen, custom Hin

Steeped in history and timeless elegance, this extraordinary circa-1860 Georgian Colonial estate offers over 8,000 square feet of refined living space where classic architecture meets remarkable craftsmanship. From the moment you enter, you are greeted by stunning period details including exquisite crown moldings, grand proportions, soaring ceilings, and beautifully preserved finishes that showcase the home's rich character and sophistication. Designed with both elegance and comfort in mind, the spacious floor plan offers an unparalleled sense of scale and flow, creating exceptional spaces for entertaining, gathering, and everyday living. Every room reflects the quality and artistry of a bygone era while providing the versatility desired for modern lifestyles. Set atop a picturesque 2-acre retreat, the property is complemented by a three-car garage, a charming 1930s greenhouse filled with vintage appeal, and an additional storage building offering endless possibilities. Surrounded by m

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is tru

Well maintained Ski on/off Kingswood Condo. 2 bedrooms, 1.5 bathroom PLUS a sleeping loft area that has a legal egress window so it is fully compliant with National and State fire safety codes. Really great price to get on the ski hill and into Quechee Lakes 4 Season Resort Community. This condo association completed a major top to bottom capital expenditure project several years ago. Enjoy as a family vacation retreat or rent it out from time to time to offset carrying costs. This condo is permitted for rentals, is ski on/ski off, being sold fully turn key and has a motivated seller

Fabulous Dartmouth Place townhouse located in the heart of the Quechee Lakes Community. Within a short walk, bike ride or golf cart to Lake Pinneo or the Quechee Clubhouse. A finer location will be hard to find! This Townhouse is located very close to the Highland golf course with beautiful views. Part of a duplex with wrap around deck, vaulted ceilings and wonderful glass and skylights that brighten every room.The large living and dining area is kept cozy with the wood burning fireplace. Three bedrooms with newly renovated primary bedroom and bathroom suite with walk in shower and double vanity on main level. Upper level is a loft for an office space or additional sleeping or sitting area. Lower level consists of two spacious bedrooms,private deck, laundry area, large bath with shower and sauna. This offering includes all the furniture including the Golf Cart. Some of the many recent updates to the condo include: High end Serpentine granite kitchen countertops, Hubbardton Forge dining

Recently renovated, 2 bedroom / 2.5 bath Birchwood Condo in Quechee Lakes. Offering 3 levels of living, this condo gets lots of light and has a great setting. On the main floor, there is a brand new kitchen featuring stainless steel appliances, gorgeous wide pine floors, propane stove, half bath as well as a 22' x 6' deck off the living room overlooking a park-like setting below. Upstairs there are two bedrooms each sharing the full bath off the hallway. In addition to being freshly painted, each bedroom has brand new windows and new carpeting. For those wanting attic access, there is a pull down located in the upstairs hallway. In the lower level, you will find additional living space, three quarter bath and sliders out to the patio. Use as a family room or even a place for visiting family and guests, this space offers lots of privacy. Nicely updated, this condo is in drop your bags move in condition offering new lighting, new hardware and even new wall mounted heaters found on both t

Open House Sunday 10/18 2:00-4:00. A renovated home with character, flexibility, and a neighborhood that welcomes you with open arms. Purchased in 2022 and thoughtfully renovated throughout by the seller, a licensed real estate professional. The kitchen and dining area, once divided by a half wall, have been opened into an inviting gathering space with vinyl plank flooring and a classic farmhouse sink. New appliances, windows, furnace, hot water heater, and bathroom fixtures bring modern comfort throughout. A welcoming mudroom with built-in storage bench opens to the kitchen and dining area, while the first floor also offers a bright laundry room, bedroom, half bath, and a former bedroom now transformed into a comfortable sitting room. The original 1940s staircase leads upstairs to two bedrooms with built-in closet features and a full bath with a charming clawfoot tub. The sitting room could easily be converted back to a fourth bedroom. Outside, the enormous expanded deck wraps around

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef's kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with he

Tucked away on a picturesque 3-acre lot, this classic three-bedroom expanded Cape offers privacy, seclusion, and wonderful views in a beautiful Rochester valley setting. Set nearly 700 feet back from the road and bordering the Green Mountain National Forest, the property enjoys a tranquil natural backdrop where a scenic pond at the edge of the land attracts birds and wildlife. The main level features a comfortable living room with a woodstove, an open kitchen and dining area, a cozy keeping room connecting to the attached two-car garage, a half bath, and a screened porch for enjoying summer evenings. Upstairs, you'll find three bedrooms and a full bath, including a spacious primary bedroom with vaulted ceilings, exposed beams, and a private balcony overlooking the landscape. With new carpet and flooring and a fresh interior paint job just completed, this property has all the makings of a truly special retreat - ideal as a quiet primary home or peaceful mountain getaway

A rare opportunity to acquire a fully occupied, well-maintained mixed-use property in one of Chester's most recognizable village locations. The front portion of the building is leased as professional office space for $5,000 per month, with the commercial tenant responsible for heat and electricity. The tenant has expressed interest in entering into a significantly longer-term lease, with the lease length and additional terms to be negotiated directly with the next owner. The property includes four additional residential units, all currently rented, including one leased by the commercial tenant for employee housing. Detailed income, expense, and lease information is available through your agent. Carefully maintained over the years, the building requires no known major upgrades or repairs and is ready for its next owner. More than sufficient parking is available on both sides of the building, along with abundant storage throughout the property, including basement garage space. Its locati

Set high in Vermont's green hills, this contemporary estate blends architectural sophistication with complete privacy on 20 pristine acres. Southern-facing glass, 18-foot timber-beamed ceilings, and frame-worthy views fill the home with natural light year-round. The sun-drenched great room features cathedral ceilings, rich wood accents, and a sleek Rais wood stove set on slate floors that store passive solar warmth. The open living and dining areas flow to a fully appointed kitchen with down-draft cooktop and direct deck access for effortless indoor-outdoor entertaining. The main-level primary suite offers vaulted ceilings, a dedicated wood stove, and a spa-like bath with whirlpool tub. Above, a dramatic loft walkway under skylights and a 32-foot illuminated cupola connects two serene bedrooms and a full bath. The finished lower level adds a flexible media lounge, office or 5th bedroom, half bath, laundry, and mudroom. Outdoor living shines with a 40-foot screened porch and sundeck ove

Owned waterfront on the Connecticut River! This solid 2 bedroom, 1 bath home sits on a 0.94 acre lot with direct river frontage and hill views across to New Hampshire. Built in 1947, the house shows the quality craftsmanship of its era, with original woodwork, arched doorways, and handy built ins throughout. The spacious living room features a fireplace, and the dining area looks out over the open, park like yard straight to the river. The first floor offers a bedroom and a full bathroom. The entire second floor is a long primary bedroom with plenty of room to spread out. Out back, enjoy the large deck with space for a hot tub and more great water views. A breezeway connects the house to the attached one car garage. This riverfront property offers character, privacy, and a great location. A short drive gets you to the grocery store, and Interstate 91 with Exit 8 or 9 just a few miles away for easy commuting. A rare chance to own a home right on the Connecticut River in Windsor, Vermont

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

Tucked into the hills of South Woodstock, this charming Cape-style home offers privacy, mountain views, and a wonderful setting on 4.6 acres of lawn and woodland. Built in 1988 and thoughtfully remodeled in 2014, the home combines classic Vermont character with inviting, updated living spaces across three levels. The heart of the house is an open kitchen, dining, and gathering area with wide-plank wood floors, exposed timber accents, natural wood cabinetry, granite countertops, a professional-style gas range, and a breakfast bar. A woodstove set against a striking stone surround adds warmth to the gathering room, while generous windows bring the outdoors in. A separate living room provides a comfortable place to unwind. Upstairs, two bedrooms feature charming rooflines and wood floors, while a beautifully appointed bath offers a clawfoot soaking tub, separate tiled shower, and beadboard detailing. The walkout lower level features a spacious third bedroom, a three-quarter bath, and attr

This wonderful home in a quiet convenient location may be a perfect fit for you! It has been lovingly well maintained with freshly painted interior, gorgeous refinished hardwood flooring, and new brand new carpet upstairs. The many upgrades such as replacement windows and the 2 mini splits offer efficiency and versatility and the standing seam roof and vinyl siding mean low maintainance costs for you. Great back deck for outside enjoyment overlooks the level back yard which offers nice area for playspace for young or old. The large primary bedroom was previously 2 bedrooms and could easily be put back to that. This Fine Home is in Easy Walking Distance to the School, Downtown Shops and Restaurants, the Town Beach at Kennedy Pond and Miles of Trails in Paradise Park

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

Ledges 8 at Hawk Resort offers the ultimate Vermont mountain retreat, featuring sweeping westerly views and year-round recreation. This spacious 4-bedroom, 3-bath end-unit townhouse spans three levels and is filled with natural light throughout. After a day on the slopes or trails, relax by the striking stone fireplace or unwind on the deck while taking in the mountain scenery. Start and end each day with inspiring views from this peaceful alpine setting. Ideally located halfway between Killington Resort and Okemo Mountain Resort, the property offers easy access to skiing, golfing, mountain biking, hiking, and a full range of four-season activities. Hiking trails are right outside your door, making it simple to enjoy Vermont's natural beauty in every season

This well situated and very private home enjoys 10.4 acres of enjoyment to view wildlife, recreate and get a good nights sleep. Generator and Fiber Optic internet ready. Living room with fireplace opens up to an enclosed porch. Traditional dining room. This home is offered furnished. Four bedrooms and a couple outbuildings provides room for everyone and their gear

This unique fixer-upper is back on the market! Nestled on 0.64 acres is a beautiful barn with many uses and the old farmhouse that has been gutted and ready for it's next chapter. Adjacent to the house stands the red barn, exuding rustic charm with its original wood. This iconic structure promises versatility and character, presenting an opportunity to create a one-of-a-kind living or workspace. Situated mere steps from the North Branch Ottauquechee River, and a short 5-minute drive from the renowned Long Trail Brewing Company, this property epitomizes the quintessential Vermont lifestyle. Downtown Woodstock is just 10 miles away, while the slopes of Killington Resort beckon from 8.5 miles, offering endless recreational opportunities including skiing and hiking trails that surround the area. Backup septic plan already permitted and no zoning in Bridgewater. Whether you're an investor seeking a lucrative opportunity or envisioning this property as your forever home, this is your chance

# Revised Public Remarks Set on 109.75 acres in the hills of Stockbridge, this well cared for Vermont property offers privacy, mountain views, open land, woods, a private pond, and the kind of setting that is increasingly hard to find. The three bedroom, two bath home blends warmth and character with practical country living. Inside, natural wood finishes, exposed beams, a striking stone fireplace, generous windows, and comfortable gathering spaces create an inviting atmosphere, while the kitchen, dining area, and bedrooms are ready to enjoy from day one. Outside, the property opens to sweeping views across the surrounding mountains, maintained lawn and field areas, mature woods, and a picturesque pond. The wooded acreage may also offer potential for selective timber harvesting, providing an opportunity to improve forest health while realizing possible timber value. A large attached garage offers two overhead doors with room for up to four vehicles, along with extensive workshop space,

They say land remembers. On Rush Meadow Road-where rolling fields meet the quiet rhythm of the seasons-there is a place that has been held, cared for, and passed down for over a century. This 103-acre estate is not something that was assembled. It was lived. Worked. Protected. For generations, it operated as a dairy farm, and the land still reflects that stewardship-lush hayfields, a ready-to-tap sugarbush, rich soil for gardening and beautiful solar exposure across every acre. It's the kind of property that continues to give, year after year. At its heart sits a classic Vermont farmhouse with 3 bedrooms and 1.5 baths, grounded by its traditional woodshed ell and surrounded by substantial garage and equipment space. It's practical, authentic, and full of quiet character, equally suited as a full-time residence or a welcoming guest house. To the west, the land opens into sweeping fields with one of the most compelling building sites in the region with long-range views stretching to Mt.

A great value! An affordable village home, located on a pleasant grassy lot, with the desirable amenities of connection to both municipal sewer and municipal water! The attractive covered front porch presents room for outside seating as well as practical protection from inclement weather. When entering the home from this porch a central hallway opens to an inviting living room, to the left. Proceeding straight down the hallway leads to a full width bright kitchen, with ample floor space for a dining area. Completing the ground floor is a half bath, off the hallway. A front staircase leads up to three second floor bedrooms. Full dormers, on either side of the home, provide these bedrooms with good useable floor space. A bathroom with a claw foot tub completes the second floor. A full size cement basement provides good interior storage. The oil furnace has been annually serviced and the electrical and plumbing have been upgraded.This traditional floor plan, with two levels of fully useab

If you've been waiting for a home that feels fresh, comfortable, and ready for its next chapter, this might be the one you've been looking for. Tucked into a welcoming Windsor neighborhood, this charming 3 bedroom, 1 bath home has had the updates you want and the everyday convenience you need. The kitchen is brand new, the windows have been updated, the roof is newer, and everything has been freshly painted, giving you a home that feels clean, bright, and ready to enjoy from day one. And then there's the enclosed porch. With direct entry from the carport, it is the perfect spot to kick off your shoes, drop the groceries, enjoy your morning coffee, or settle in with a good book. It is one of those spaces that quickly becomes everyone's favorite. The neighborhood is another reason to fall in love with this home. Think evening walks, bike rides with the kids, friendly neighbors, and the kind of neighborhood that feels connected and comfortable. Three bedrooms give you room for family, gue

Experience the charm and beauty of Vermont living in this lovingly maintained, single-owner home nestled in the highly sought-after Quechee Lakes community just off Baker Turn Road. Thoughtfully cared for over the years, this spacious home offers the perfect blend of comfort, quality, and opportunity. A brand-new roof and solid construction provide peace of mind, while the generous floor plan offers room to enjoy today and the flexibility to make it your own over time. Move in and enjoy immediately, then update at your own pace to reflect your personal style while adding future value. Property Highlights: Wonderful screened porch, perfect for relaxing on rainy evenings or bug-free summer nights. Four spacious bedrooms with the potential for a fifth bedroom or a main-level primary suite. Expansive living spaces designed for entertaining family and friends. Meticulously maintained by its original owner, reflecting years of pride in ownership. Exceptional value with an attractive price pe

Set on 3.4 private acres, this 3-bedroom, 3-bathroom Lindal Cedar home offers the rare combination of quiet mountain views and a location just a short walk from the heart of Weston Village. Inside, the living room is anchored by a cathedral ceiling and large windows that overlook Andover Ridge, bringing in ample natural light. The layout also includes a partially finished walk-out lower level, providing extra living area that can easily be tailored into a game room, home office, or completed as a separate suite. Outside, you can take in the scenery from the expansive deck. Recent improvements include a brand-new roof and skylights. This property is rounded out by a classic post and beam barn, offering excellent space for a workshop or extra storage. A beautifully sited home that perfectly balances Vermont privacy with village convenience

Tucked away along a long driveway on 5.6 wooded acres, this 3-bedroom, 2-bath split-level home offers the privacy, space, and peaceful Vermont setting you've been looking for. Located on a private road in West Windsor, the property is surrounded by natural beauty, creating a wonderful sense of seclusion while still being within reach of nearby amenities and recreation. Whether you're looking for a quiet place to unwind, room to explore the outdoors, or a property with space for your hobbies and interests, there's plenty to appreciate here. Inside, the home offers a comfortable and welcoming atmosphere, with a woodstove adding warmth and character during Vermont's cooler months. The sunroom provides an inviting place to enjoy your morning coffee, settle in with a good book, or simply take in the changing seasons. One of the property's most impressive features is the expansive deck, offering an incredible amount of outdoor living space. From summer barbecues and gatherings with friends t

Classic New Englander, ideally set in town on an easy-to-maintain lot. The inviting porch adds to curb appeal. The manageable yard means less time on upkeep and more time enjoying all that in-town living has to offer, with shops, dining, and amenities close by. Inside, the home offers 3 bedrooms and 1 full bath, a layout with character throughout. A detached shed provides extra storage for tools, seasonal gear, or outdoor equipment. It's all close to downtown Windsor, with easy access to I-91, Route 5 and the Upper Valley. A great fit for first-time buyers or anyone looking for character without the big project