Windsor County, VT homes for sale & real estate

Windsor County, VT Homes for Sale

This property offers significant potential with a partially completed renovation project to expand its layout to 4 bedrooms and 3 baths. Located near Okemo, it presents an excellent opportunity for a vacation home, rental investment, or full-time residence. Key systems, including plumbing and electrical, are roughed in and ready for finishing. While some structural and heating system work remains, included materials such as the tankless water heater and kitchen cabinets provide a head start. This home is perfect for buyers looking to complete a custom renovation in a charming Vermont location. The sale of this property being listed is contingent upon the proposed Seller (or "Owner&quo

Windsor County, VT Homes for Sale

Welcome to this charming 2-bedroom, 2-bathroom Cape-style home, offering a perfect blend of comfort and functionality. As you enter, you’ll be greeted by a warm, inviting living area with a pellet stove that leads to the kitchen, ideal for preparing family meals and entertaining guests. The main level features a full bathroom, while the second level boasts the two official bedrooms and the additional bathroom for privacy and convenience. In addition to the two bedrooms, this home offers two versatile bonus rooms, perfect for a home office, playroom, or additional living space. The large backyard provides ample room for outdoor activities, gardening, or simply relaxing in a peaceful se

Windsor County, VT Homes for Sale

A classic, easy maintenance four bedroom, two bath home in Chester village on . 12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and elegant lighting, a country kitchen with marble tile flooring, first floor bath with tiled shower and an adjoining bedroom with a lovely reading/entertainment nook that connects with the dining room. The second floor has a large landing with two adjoining bedrooms, a full bath with radiant heat in th

Windsor County, VT Homes for Sale

Bixby House 647. What a location!! Unique and Slopeside, 2BR, 2BA, ski to and from the deck!! Primary bedroom has a king-sized bed and ensuite bathroom with double sinks and jacuzzi tub. Second bedroom has two queen sized beds with large second bathroom. Mudroom with washer and dryer. Nice open dining/living/kitchen concept with lots of windows bringing light and nature inside. Large pantry off of the kitchen and sleeper sofa in the living room. Enjoy convenient slopeside location at Bixby House, combined with the luxury amenities including an onsite owners' lounge, business center, private underground heated parking and access to the Spring House fitness center, heated indoor and outdoor

Windsor County, VT Homes for Sale

Nestled on over an acre of serene countryside, this 3-bedroom, 2-bathroom home offers endless potential for those seeking a peaceful retreat with room to make it their own. Enjoy the beauty of nature with direct river frontage, perfect for fishing, kayaking, or simply relaxing to the soothing sounds of the water. The home features a spacious layout with abundant natural light, offering a cozy living room, a spacious kitchen ready for updates, two bathrooms, and three bedrooms. While the interior is ready for updates, it provides a blank canvas to customize to your taste and create the home of your dreams. Outside, the expansive lot is ideal for gardening, outdoor activities, or even future

Windsor County, VT Homes for Sale

14 Ridgeway is newly renovated inside from floor to ceiling! The sellers recently installed a new hot air furnace, a new water heater, spray foam insulation throughout by SEVCA, new laminate flooring, a remodeled bathroom to include new plumbing, updated light fixtures in all the rooms, and in the kitchen you'll find a new sink and cabinets. This property has no yard to maintain, but there is a great playground just a short walk up the street which has a basketball court, play structure, and sledding hill! Come take a look.

Windsor County, VT Homes for Sale

This Totally Renovated 3 BR 2 Bath Cape On a Quiet Dead End Street Has Everything You Want. Newly Modernized Kitchen with Granite Counters and Tons of Cabinets, Awesome Dining Room With Lots of Windows and Spacious Living Room with Electric Fireplace and Beautiful Hardwood Floors Throughout Most of the Home. Plus Both Gorgeous Bathrooms were Just Redone. Spacious Lower Level Family Room with Woodstove for Heating Efficiency and Charm and Slider to Walk Out to Your Level Back Yard With Frontage On and View of the Black River. Nothing Needed Here Except For You!!

Windsor County, VT Homes for Sale

Welcome to 1062 Andover Ridge where you can buy a million-dollar view and get a gorgeous log home to go with it. The views are breathtaking and can be enjoyed from almost every room as well as the deck from either in or out of the 6-person hot tub. The recently renovated exterior and kitchen make this a perfect Vermont dream home. High-end stainless appliances, soapstone kitchen island, massive wood-burning stone fireplace, second living room, great mudroom, and primary bedroom en suite check off most people's boxes. This 3 bedroom plus/3 bath home can entertain large families or group of friends with a great open floor plan that allows easy flow from the kitchen through the dining room and

Windsor County, VT Homes for Sale

10 FAIRBANKS TURN- Elegant and spacious home in ideal central Quechee location with easy access to downtown Woodstock and Hanover. Sited on a large 1.4-acre beautifully landscaped lot with flat lawns and a variety of plantings and garden beds, the property is just minutes from the Quechee Club and its two championship 18-hole golf courses. The house features an open floor plan with high ceilings and warm natural light and a central great room on the main level anchored by a fireplace, built-ins, and more intimate spaces for gathering that flank the area. A well-appointed large chef's kitchen has an adjoining eat-in space, while a lovely sunroom to the east side adjoins a private garden prov

Windsor County, VT Homes for Sale

This gorgeous high quality three-bedroom house with over 2100 of finished living space is situated on two beautifully landscaped acres in the special town of Weston. Located in the heart of ski country with four ski areas close by, this home has much to offer. The house has a wonderful feel of relaxation and welcoming. As a four-season destination, Weston and the surrounding area has much to offer from skiing to hiking to fishing to golfing to swimming to "leaf peeping" and to just relaxing. A beautiful home is in a desirable location to live fulltime or enjoy as a vacation home; either way this house is a must see sooner than later. The property also has an impressive, heated bar

Windsor County, VT Homes for Sale

The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer

Windsor County, VT Homes for Sale

This charming 4 bedroom/1 bathroom home offers 1,802 square feet of comfortable living space on a large 0.16 acre lot. The interior features a blend of wood and tile floors. The home offers a large living room leading into a formal dining room, an additional fenced-in area for gardens, a spacious eat-in kitchen with ample wood cabinets, and second-floor bedrooms, including one with a walk-in closet. A comfortable reading room/study or office is located at the end of the hallway. A cozy front porch and a delightful backyard gazebo provide perfect outdoor retreats. Conveniently located in the outskirts of downtown Springfield, this home is close to shopping, banking, and restaurants. A s

Windsor County, VT Homes for Sale

Investment Opportunity! This fully leased 2 unit multifamily property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an onsite owner to occupy one unit and let the extra additional rents help pay for your housing. Fully leased with long term tenants. The property is well maintained with many updates over the years which include new windows, roof, insulation, some appliances, and interior updates. Inside you will find spacious rooms, generously sized kitchen spaces and beautiful original wood trims. Sited on . 13 +/- acre in town lot is walking distance to local library, public transit and Kilowatt Park. Minutes to downtown White Rive

Windsor County, VT Homes for Sale

Strong Cash Flow! Profitable Investment Opportunity! This fully leased four unit multifamily property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an onsite owner to occupy one unit and let the extra additional rents help pay for your housing. A low maintenance property with many updates over the years which include windows, separate electrical meters and interior updates of the units. Inside you will find spacious rooms, generously sized kitchen spaces and wonderful wood trims. Located on a generous . 30 +/- acre in town lot this Maple Street property is within walking distance to the vibrant and transformed downtown White River

Windsor County, VT Homes for Sale

Strong Cash Flow! Profitable Investment Opportunity! This four unit multifamily property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an on site owner occupancy and the extra rents to pay for your housing. Located in charming Wilder village on a generous . 25 +/- acre in town lot. The units consist of three bedroom, two bedrooms and a studio, separate entrances, electrical meters, hot water tanks , porches and parking areas. Updates over the years include some new roofing, kitchens, flooring and windows. Conveniently located near shopping, public transportation, Downtown White River Junction Arts and Theatre district, CO-OP food st

Windsor County, VT Homes for Sale

Excellent opportunity to own a Wilder village / Frost Park area duplex! This single family conversion home features a wonderful, level, spacious in town neighborhood lot, convenient location, possibility of single level living, and income potential all make this home a rare find! This multi-family home has 2 units, each with 1 bedroom and 1 bath. The kitchen, dining & living room areas have a mostly open concept design which give it a spacious feel. Both units have their own driveways / parking areas & entries. Move-in to one and rent out the other unit for the income, make the investment and rent out both units or the property could easily be converted back to a single family h

Windsor County, VT Homes for Sale

A picture perfect setting awaits you! Just imagine a home on a town maintained country road that is less than a mile from Route 131, yet is walking distance to Proctor Piper State Forest for hiking & biking. Those who snowmobile, the trail is about a 1/4 mile away. The home has classic lines from the 1800's. All summer long there is something in bloom-lilacs, iris, hosta, day lillies & more. Very private yard with a gazebo beside your very own pond. Just gorgeous & wait until you see the waterfall! The home is simple yet full of warmth. It has been in the same family since 1960 when it was purchased from the Densmores. The family is still in the area and owns the surroundi

Windsor County, VT Homes for Sale

Attractive 3 BR 3 BA walk up condominium in the Windsor Building at Ascutney Mountain home of Ascutney Outdoors! Open fireplaced LR/Dining opens to Deck overlooking the Tubing Hill. Enjoy all the action right out your door! * Covenants & Right of First Refusal. The Mountain offers inexpensive skiing on natural snow. Mountain biking, hiking, cross country skiing, snow shoeing. Approx. 1300 acre playground. Woodstock, Ludlow, Okemo are all about 30 minutes away. Killington, Bromley, Magic a little more. The Green Mountain Horse Asso. is about 20 min. away. Boston and Hartford about 2.5 hrs depending on traffic. Great outdoor recreation with a good restaurant at the Hotel a short walk

Windsor County, VT Homes for Sale

Luxury properties of this caliber don’t come on the market often, so if you are seeking the ultimate getaway retreat, you need to experience this one for yourself. Designed by famed Vermont Architect Robert Carl Williams and exquisitely crafted by Moore Construction, this Vermont Masterpiece features the finest finishes and most thoughtful details at every turn. Floor to vaulted-ceiling windows offer incredible mountain views. And with custom stonework surrounding three separate fireplaces on the main floor, and radiant floor heat throughout, you won’t find a cozier place to relax and recharge. The open concept main floor combines kitchen, dining and living areas - perfect for e

Windsor County, VT Homes for Sale

This inviting 5-bedroom, 4-bath home is located in Hawk Resort, offering both privacy and convenience. The bright, open main floor features soaring cathedral ceilings, large windows, and beautiful wide pine floors. A striking gas-fired stone fireplace serves as the focal point of the living area. The dining room opens to a spacious deck, ideal for outdoor dining or relaxation. The main level also includes a bedroom, a bunk room, and a full bath. Upstairs, two en-suite bedrooms each have their own private balcony. The lower level offers additional living space with a cozy family room, wet bar, another bunk room (no windows), full bath, and extra storage. Sliders from the family room lead to

Windsor County, VT Homes for Sale

INVESTMENT PROPERTY, with two 4 BR's apts. and one 1 BR's apt. Walk to town locations. Gross rent, $43,140.00, total expenses $19,992.00, net $23,140.00. Current cap rate is 12.5. Requires a minimum of 48-hour notice to show.

Windsor County, VT Homes for Sale

A wonderful opportunity to own a condo right on Okemo Mountain! This property has been lovingly maintained for over 50 years by the same owners. It's location is perfect for skiing, as it sits in the Trailside community and is a short walk to the Sachem Trail. This home boasts 3 bedrooms, 2 bathrooms and a loft with a skylight. The living, dining and kitchen area is an open concept plan. There is a wood burning fireplace in the living room for cold winter nights. There is also a den with a deck right off it, to enjoy mountain views. This property comes fully furnished, with the exception of art work. Amenities include a seasonal swimming pool and tennis courts, with additional parking for f

Windsor County, VT Homes for Sale

This sprawling house sits in the corner of a stunning park-like lawn, hidden from the world but easily accessible and near town conveniences. Close to The Barnard General store, Silver Lake, quintessential Woodstock and charming Bethel. There is plenty of room outside for play. Enjoy the yard with its ponds, rock walls, and gardens from the deck or the covered porch. First-floor living includes a sun-filled kitchen and dining room, a large living room, and 3 bedrooms, each with a walk-in closet, and 2.5 baths. The office could become a 4th bedroom. Downstairs, in the mostly finished basement, you will find a bedroom with a full bath and a walk-in closet. There are two large rooms, a kitchen

Windsor County, VT Homes for Sale

Absolutely turnkey Woodstock. Totally renovated in 2019.Gorgeous open concept cape cotemporary. Move right in. You should see this gem abuts Woodstock Middle and High School. Open concept 3 bedrooms 1/2 l bath one renovated next to the primary bedroom over a month ago. The backyard is wonderful private. Lower level is totally a cool playroom. Brand new kitchen. New roof. Come see, a must see to appreciate this Woodstock property. A gem! Zoned Residential and Commercial.

Windsor County, VT Homes for Sale

Discover Your Mountain Retreat Nestled in the heart of the sought-after Mountains Edge community, this condo offers the perfect blend of adventure, comfort, and connection. Once a ski-in/ski-out gem, it has transformed into a mountain biker’s paradise with an abundance of trails while still embracing its winter sports legacy. Whether you’re carving turns on the Ascutney Mountain rope tow and T-bar or exploring serene backcountry trails, this vibrant community has something for everyone. After a day of outdoor fun, swing by the Brownsville Butcher & Pantry to grab a local treat and connect with friendly neighbors. The condo itself is a haven of modern mountain living: 3 B

Windsor County, VT Homes for Sale

This charming 3-bedroom, 1-bath mobile home sits on a generous 1.25-acre lot, offering the perfect balance of privacy and convenience. The home has been thoughtfully updated, featuring modern finishes and upgrades throughout. Whether you're a first-time homebuyer or looking for an affordable property with room to grow, this home is a fantastic opportunity! The home features a spacious living area, 3 cozy bedrooms, and a full bath. The home has a block foundation that sits atop a poured concrete pad with tie-downs for added stability. There's plenty of room for outdoor activities, gardening, or even expanding the home or adding outbuildings, making it ideal for those who enjoy a rural lifes

Windsor County, VT Homes for Sale

This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a covered breezeway is a large 2 car garage, gorgeous horse barn with hay loft and a cozy studio apartment, making this the perfect spot for a variety of uses. Equally comfortable as a part-time or full-time home, this property is conveniently located on the western side of Woodstock, just twenty minutes fr

Windsor County, VT Homes for Sale

An exciting opportunity to own a new 3-bedroom, 2-bath double-wide home in Hartland, VT Open Concept Living: Bright family area with built-in storage. Stylish Kitchen & Dining: Includes a wall electric fireplace, large island, coffee bar, and a walk-in corner pantry. Luxurious Primary Suite: Enjoy a walk-in shower, private commode, double sinks, and a massive walk-in closet. Additionally two more Bedrooms at the end of the hall, perfect for family or guests. Convenient Laundry Area: Spacious and functional. This home is on a slab with insulated skirting, meets VT energy standards, and is just 5 miles from the VA Hospital. The home is brand new, move-in ready, and available for immedia

Windsor County, VT Homes for Sale

This is a dream come true for someone who is seeking a Vermont nature retreat. Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two add ons! In addition to this classic home, you will have 40+ acres of beautiful land. Only one other house can be seen from the property & you have to know where to look! The views of Mother Nature & Vermont's wildlife are truly special. The back yard has lawn area with room for games, gardens or pets. When you are peering out any of the windows toward the back of the house you overlook a giant pond and wetland-home to a terrific assortment of wildlife. Head out

Windsor County, VT Homes for Sale

Enjoy all the conveniences of Village life, with a tranquil view of rolling green horse pastures right from your window. This absolutely-charming antique New Englander has one of the best locations in town. Just outside your back door you'll enter the 200 AC Paradise Park nature trail network, complete with ponds, waterfalls, vernal pools and wildlife. The house is tidy, efficient, and lovingly stewarded. Enter the rear mudroom with direct access to the bright kitchen and open concept dining room, with sliders to the spacious deck overlooking established perennial beds, fruit trees, mature plantings, and a huge flat yard for gardening and recreation. Livingroom, one bedroom and bathroom fu

Windsor County, VT Homes for Sale

Are your favorite things skiing, views, sunshine, family time, gathering with friends, or enjoying a cozy fire? If so, this "Treehouse" could be your perfect retreat. Located in the desirable West Village area, this home offers deeded ski access to Okemo's Sachem Trail—just carry your skis to the end of the loop and hit the trail. After a morning on the slopes, ski back for lunch and enjoy a short, easy walk home. With a prime location and breathtaking sunrise views, this property is ideal for creating lasting memories. Crossing the private footbridge to the house, you’ll enter a mudroom with ample storage space for ski gear. From there, stairs lead up to the main livi

Windsor County, VT Homes for Sale

This immaculate Ridge condo located in the highlands of the Quechee Lakes community has sweeping views of the Ottaquechee Valley, the ski mountain and championship golf courses—with western exposure it is a perfect for sunset lovers! This bright interior unit offers an updated kitchen flowing into a sunlit living and dining area with cathedral ceilings, wood floors, and a wood burning fireplace. The main level features a convenient bedroom and updated full bath. An open loft with views completes the top level and downstairs, the primary suite includes a private deck. There is an additional bedroom, 3/4 bath, and flexible bonus space with a sauna that is ideal for a spa, playroom, or e

Windsor County, VT Homes for Sale

Are you looking for versatile living space. This large home has many options. Currently set up as a two unit but occupied as one family it would be a great space for a multi-generational home. Even the basement has finished space. Covered wrap around porch lends to lots of outdoor living. Finished living space on four floors, five parking spots, green space on two sides and the back yard. This is a solid home. Take a look soon!