658 properties for sale in Windsor County

Set among the rolling hills of Andover, this inviting three bedroom home captures the best of Vermont living with beautiful long range views, morning sunlight and a peaceful country road setting. Whether youre looking for a full-time home, weekend escape or four-season retreat, this property offers the space, flexibility and setting to settle in and truly enjoy it.Ideally positioned for year-round recreation, youre within easy reach of some of Vermonts most sought-after ski destinations, including Okemo, Magic, Bromley, Stratton, Mt. Snow, and Killington. Nearby Manchester, Chester and Ludlow add charming village centers, restaurants, shops and everyday amenities, making it easy to enjoy both adventure and convenience.Inside, natural light fills the main level, with large windows bringing the surrounding landscape into the living spaces. The remodeled kitchen features granite countertops and a center island with cooktop and dishwasher, while a wood cook stove creates a warm atmosphere.

Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4-bedroom, 2-bathroom home offers the character of a traditional New England property with comfortable, move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace-perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean, inviting feel while preserving the home’s classic farmhouse charm. An attached barn/garage offers excellent storage and flexible space for outdoor gear, a workshop, or hobby area- ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full-time residence or a Vermont getaway, this property offers an excellent opportunity to enjoy one of Vermont’s most desira

Set at the end of a quiet country road in Barnard, this distinctive Vermont retreat offers an exceptional combination of privacy, acreage and sweeping long-range mountain views. Surrounded by mature woodland, open meadow and expansive sky, the setting feels wonderfully removed while remaining within reach of Barnard Village, Woodstock and the Upper Valley.The home was designed to take full advantage of its surroundings. Expansive windows and glass doors bring the landscape into the main living spaces, where hardwood floors, natural woodwork and a fireplace create a warm and inviting atmosphere. The living, dining and sitting areas flow comfortably together and open onto a generous deck overlooking the meadow, forest and distant ridgelines.The kitchen is substantial and well suited for entertaining, with extensive cabinetry and counter space, a large center island, farmhouse sink and professional-style Viking range. Flexible rooms on the main level can accommodate guests, office space,

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 t

SERENA LODGE is a one-of-a-kind private mountain estate where timeless architecture, natural beauty, and the Vermont lifestyle come together to create an extraordinary legacy retreat. Inspired by Rockefeller's famed Adirondack Great Camp, The Point, this nearly 9,000-square-foot residence is nestled on over two acres overlooking a crystal-clear brook, with the gentle sound of cascading waterfalls flowing year-round. Serena Lodge combines the privacy and scale of a standalone mountain estate with the convenience of being part of the established Hawk Mountain Resort community. Through the association, owners benefit from road maintenance, snow removal, emergency services, and property management, making ownership easier and more turnkey, particularly for those enjoying Serena Lodge as a second home.Perfectly positioned for four-season recreation, Serena Lodge is approximately 20 minutes from both Killington and Okemo Resorts, about 30 minutes from the quintessential New England village o

Set at the end of a quiet country road and surrounded by 45 private acres, this quintessential Vermont farmhouse offers a rare combination of history, space, and natural beauty. Built in 1750 and lovingly held by the same family for the past 40 years, this charming four-bedroom, one and a half bath residence encompasses 2,620 square feet with inviting living spaces, natural light, wood floors, and the timeless character only a historic home can provide. The thoughtfully arranged main level features a primary suite, along with a second bedroom that offers excellent flexibility as a nursery, home office, or guest space. A formal living room with hearth and fireplace provides a warm gathering place, while the inviting dining area features a picture window framing views of the Green Mountains and peaceful surrounding landscape. The second level offers two additional bedrooms and a versatile den, providing comfortable space for family, guests, work, or hobbies. A separate studio with beauti

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

Welcome to Quechee Hollow 2C, nestled in the picturesque town of Quechee, Vermont. This newly renovated two bedroom, one bath condominium offers a perfect blend of mountain comfort and convenience. The inviting and very cozy living room features a wood-burning fireplace, creating the perfect setting to relax, and warm up after a day on the slopes, or enjoying the outdoors. The upstairs includes two generously sized bedrooms with beautiful hardwood floors. Ownership in Quechee Lakes, includes access to The Quechee Club which is only a five minute drive, or ten minute bike ride along the scenic Ottauquechee River. In the spring, summer and fall months enjoy two championship golf courses, and in the winter months take advantage of groomed Nordic skiing. The Club also offer amenities such as tennis, paddle, pickleball, skiing, swimming and access to Lake Pinneo. The Main Club House offers multiple dining options and a state-of-the-art fitness facility with indoor and outdoor pools, perfect

Fully furnished condo nestled in a small quiet community just 5 minutes from Historic Woodstock. Super location! This unit is in very good condition- first floor is comprised of a den/bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom are perfect size for guests. Lower level has a walk out patio with new slider doors, large family room with a small kitchen and eat-in area, spacious laundry and 3/4 bathroom. Newer Buderus boiler. Pets are allowed- Offered furnished with all new custom curtains. Come take a look at this turnkey property

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 whi

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 conveni

Nestled in the heart of historic Woodstock. This 1875 colonial abuts Mt. Peg with direct access to the trail system. A large shed in the backyard could be used as a workshop and/or storage, ample space for gardening and very private backyard for entertaining. The house had some upgrades to the kitchen and bathrooms and still boasts some of the original features including hardwood floors in the bedrooms upstairs. First floor has a mudroom, large, oversized kitchen with cherry cabinets, stainless steel appliances and stone countertops anchored with an island and opens to the dining area. There is a handsome set of French doors that walk out onto a stone patio. The living room is spacious with a wood-burning fireplace and a small room that could be used as an office. The second floor has 3bedrooms and a full bath. The primary bedroom has ample space to add a separate bathroom. This home has a newer heating system. It's a great project for a buyer wanting to put in some sweat equity and re

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 fo

Stunning Deck House perfectly designed for light, views, and easy Vermont living. Soaring floor-to-ceiling glass in the entryway and stairwell connects all levels and creates a warm, treehouse-like feel, drenched in natural light. Honey-colored hardwood floors warm the main level, while wall-to-wall carpet and tile finish the rest of the spaces. The main level also features a striking stone fireplace, the architectural centerpiece of the expansive living room, complemented by a cozy propane stove and an intimate den with an electric fireplace. Step onto the deck, where new Pella sliders capture a framed summer view and expansive seasonal vistas, with a hot tub for year-round enjoyment.The primary suite includes a shower and peaceful outlook, while the superior guest suite showcases floor-to-ceiling glass, an en suite shower, and sunrise views. The lower level offers two spacious bedrooms sharing a double-vanity bath; ideal for family or guests. Thoughtful upgrades include a tidy laundr

This 1885 antique story and a half cape have been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional Livingroom and dining room with the more casual lifestyle of today. The open concept Vermont country kitchen-dining and family room flow into a south facing sunroom overlooking the Ottauquechee River with a terraced yard providing direct access to the water. The home is midway between the resort communities of Woodstock and Killington 5 and 9 miles away. A public park and the Bridgewater Mill showcasing nationally and internationally recognized handmade furniture and pottery of Charles Shackelton and Miranda Thomas, respectively, in addition to a popular restaurant with live entertainment all within walking distance. Ideally sited offering an array of amenities at an attractive price

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

Lovingly cared for by the same family for decades, this inviting three-bedroom, two-and-a-half-bath condominium enjoys a lovely setting with easterly views in a particularly appealing spot within Salt Box Village. Parking just steps from the front door makes coming and going easy, while Quechee Village and Simon Pearce are within walking distance.The open-concept main level offers ample room to gather with family and friends, with a wood-burning fireplace bringing warmth and charm to the living space. The lovely deck extends your living space outdoors. a welcoming spot for morning coffee, dining, or simply enjoying the peaceful surroundings. Steps lead directly to the lawn, creating an easy connection to the grounds. Upstairs, the spacious primary bedroom suite captures morning light and easterly views.All windows and sliding doors have been replaced with Andersen windows and sliders, and a new roof installation is planned for this fall. Exterior storage and a first-floor half bath add

Opportunity awaits in the heart of Rochester Village! Located just off the Village Green, this versatile property offers exceptional income-producing potential. The existing second-floor apartment, complete with its own bedroom and full bath, is ideal for rental income, guest accommodations, employee housing, or multi-generational living. With its generous layout and village location, the property also offers the potential for up to three residential units or business use, subject to local zoning and municipal approvals.The main home features 6 bedrooms, 1 full bath, 1 three-quarter bath, and 1 half bath, providing abundant space for a large household or live/work lifestyle. Combined with the separate apartment, this is a rare opportunity for homeowners and investors alike.The fenced 0.25-acre lot includes a garden area and plenty of room for pets, outdoor entertaining, or simply enjoying village life.Enjoy an easy stroll to local shops, caf?s, restaurants, galleries, and community eve

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

If privacy and a magical setting is what you are looking for you need to look no further Auger Hole is what you are searching for. Hidden away at the end of a town-maintained road one will find the historic stone cape that was built for Vermont Senator Delano in 1815 by the well-known Wardner family of Boston. Senator Delano wanted a stone cape built with European style details. The two fireplaces on each end of the large great room with exposed beams are examples of this early style. The site was chosen for the view of Mt. Ascutney and the protection of the surrounding hills. The 36.5 acres are comprised of mature woodlands and open meadows. The large spring fed pond is perfect for swimming on hot summer days and ice skating in the winter. In recent years a modern 2-bedroom house was added to the grounds. Large windows were used to bring the magnificent outside in. The downstairs open-air floor plan and spacious bedrooms upstairs create a comfortable, easy, lifestyle. The lovey perenn

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

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

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 attrac

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

Discover the possibilities of this spacious Weston retreat, offering over 5,400 square feet of finished living space and a remarkably flexible layout just 8 miles from Okemo Mountain Resort. Designed with two complete living levels, each featuring its own kitchen, primary ensuite, living and dining areas, laundry, screened porch and separate exterior entrances, the home offers exceptional versatility for extended stays, remote work, recreation and gatherings.The main level is highlighted by a dramatic great room with soaring ceilings, exposed timber trusses, warm wood floors and a loft overlooking the living space. The spacious kitchen features granite countertops, a center island, gas range and pantry. The walkout lower level offers its own complete living areas, additional flex rooms and radiant floor heat, providing comfortable, independent spaces within the home.An attached two-car garage includes workshop and storage areas, with finished bonus space above. Outside, enjoy landscape

Lovely views overlooking the Pomfret hillside and lush meadows on a private, dead-end road in North Pomfret. Quiet and peaceful. This ranch style home has many upgrades, with a 2-bay attached garage for easy access to the dwelling. It features all one floor living with 3 bedrooms, spacious living room, dining area with new kitchen - views and an abundance of natural light throughout. The basement could be finished for an additional 800+ square feet or turned into a workshop- ample storage. Generator on site, large deck expanding the back of the house overlooking meadows and view. New systems. Easy access to Upper Valley, Dartmouth or historic Woodstock- skiing, fly fishing and shopping within 15 minutes. Come take a look!

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three luxurious residences in the heart of the Village.Unit B occupies the top two floors and offers over 3,200 square feet of beautifully appointed living space with the feel of a private home. The main level features gracious living and dining rooms with a wood-burning fireplace, a spacious family room, and an en-suite study or guest bedroom with its own fireplace. The kitchen opens to the family room and is filled with southern light. A built-in bar near the dining area leads to a private balcony overlooking the Village and landscaped grounds, perfect for morning coffee or evening entertaining.The upper l

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

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

An exceptional 13.1-acre equestrian property with direct access to the GMHA trail system in sought-after West Windsor. This Lindal Cedar home features expansive windows, vaulted ceilings, and wide decks overlooking grassy pastures and distant views of Mt. Ascutney. The newly designed kitchen includes Crownpoint cabinetry, granite countertops, and stainless-steel appliances. Upstairs, the primary bedroom has a wood-burning fireplace, while the ensuite bathroom offers a soaking tub and tiled shower. Two additional bedrooms on the main level, each with a bathroom. First-floor laundry / powder room. Mudroom with custom cabinetry and direct access to a 2-car garage. Automatic generator. The stone patio includes a fire pit, and the property has electric dog fencing. A custom two-story barn offers five stalls with direct access, heated tack room, automatic heated waterers, large, fenced grass paddocks, an oversized riding ring and round pen, All-season recreational opportunities with easy acc