Windsor Vermont Real Estate

Spacious and affordable 3-story dwelling in Windsor. Buy it as a starter home, or take the opportunity for renovation and rental or resale. Pleasant stone landscaping in the yard. A kitchenette is found in the 3rd floor apartment (perhaps a rental unit or an in-law suite?) There's proximity to shopping (including a fine glass store, brewery, distillery, and jam shop), Amtrak, Mount Ascutney Hospital, and across the street from the Connecticut River!

Amazing opportunity to easily convert this 6 bedroom duplex into a single family home! Or, have a perfect in-law apartment. Great location across the street from Windsor High School and backing to Lake Runnemede! The yard has mature shade trees. With a little clearing, you may be able to have views of Lake Runnemede which is just down the hill from the house. There is a narrow strip of park land between the house and the lake. This home has strong bones, feels solid, and has level flooring which is rare for homes of this age. It is a tremendous value with so much potential - it just needs some cosmetic work to bring it up to date. There are hardwood floors under all carpeting with the exception of the 17' bedroom over the garage which is an addition. Deeded access to shared driveway. Downtown shops and restaurants are just a short .3 mile walk on sidewalks. Convenient location just 20 miles to both Lebanon and Hanover, NH. Mt. Ascutney Hospital is less than a mile. Nature enthusiasts will love easy access to the 5 miles of trails at Paradise Park just a half mile away. Neighboring Lake Runnemede is a birding hotspot with over 215 species of birds sighted and beautiful Mill Pond is just 1 mile. So many amenities for such a low price!

Come check out this very cute diamond in the rough! This home offers 2 good sized bedrooms with huge closets and a primary with a deck off the bedroom, as well as potential for a en suite bathroom....Several possibilities for the downstairs as well....Along with a 2 car garage with possible furnace hook up and its own electrical panel. This property is convenient to in town amenities and all that Windsor has to offer!

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the years, the house was purchased by Historic Windsor, Inc. in 2008. Recognizing its historic significance along with much original fabric intact, Historic Windsor, Inc. engaged in a massive cleanup, extensive documentation and a complete paint job with some sections reroofed with standing seam. The residence is now ready for the next phase of its life as a single family residence, up to 4 residential apartments, owner occupied business or a cultural center. All of the necessary as built architectural plans, documentation of existing materials and fabric and proposed Feasibility Plans are available. The project will require all new systems and rehab working with the extensive original fabric including interior shutters, period flooring and window and door detailing. Many original doors. The residences rich history with Stephen Jacob and its architectural significance will regain its prominence in Historic Windsor upon completion.

Step into this beautifully taken care of vintage charmer, where classic Vermont character meets modern comfort. The home's original features are intact, including stunning maple hardwood floors and a striking tiger eye maple staircase that captures the essence of timeless elegance. The kitchen is a perfect blank canvas to add in your own personal touches. Enjoy the serenity of the seasons on your inviting front porch, perfect for relaxation. The property also includes a double garage and two spacious barns, offering endless possibilities for hobbies, collectibles, or even a home business. Located just 17 miles from the Upper Valley, this home offers a convenient commute while allowing you to immerse yourself in the welcoming Windsor community. With mixed-use zoning, your imagination is the limit—whether you're looking to create a cozy family home or explore entrepreneurial ventures. This is more than just a house; it's a home that's been cherished and loved. Don’t miss out on this unique opportunity!

Completely Remodeled! This stunning home has undergone a total makeover, emerging as a beautiful, clean, and charming retreat in a lovely neighborhood. With nothing left to do but move in and enjoy, this 3+ bedroom residence boasts a brand-new kitchen, updated bathroom, and a newly restored mudroom entry and deck with laundry and 1/2 bath. Sunlight fills every corner, creating a bright and inviting atmosphere. The backyard is perfect for summer BBQs, while the covered front porch offers a cozy spot to relax and watch the world go by. The home is packed with extras, including gleaming hardwood floors, vinyl siding, updated wiring, a newer boiler, and granite countertops. A full basement and a two-car garage provide ample storage and convenience. Come see us Sunday 9/8/24 for an OPEN HOUSE 10-12

Charming Cape with a spacious L addition and attached barn with storage above. Features include 3 bedrooms and a full bath upstairs, and a bedroom with a half bath on the first floor (just needs a door). Enjoy a 22x12 front living room with beautiful old wood floors, a remodeled kitchen with newer stainless appliances and a walk-in pantry, and a sunny dining room with built-ins. The private, large fenced-in backyard is perfect for entertaining with a patio and gazebo. Beautiful plantings surround the home. Cedar shake siding, a roof updated in 2015, hot air heat, and a new hot water heater from last year. Delayed showing until Friday 9th, Open house Saturday from 10:00 to 12:30

Don’t scroll past this listing without flipping through all the pictures! This turn-key 1988 ranch with a full concrete basement and attached garage in a quiet cul-de-sac neighborhood located in Windsor, Vermont is calling your name! Move right in with ease as the property is available now. Live comfortably on the main level with three bedrooms and two full bathrooms, plus the downstairs has high ceilings and represents a lot of potential future finished living space, if you need room to grow. Brand new appliances in the kitchen still have the tags on them. The private back deck leads to a side entrance to the garage and through to the basement, which conveniently connects back up to the main level. Primary suite with private bathroom. Plenty of parking for your guests. Recent upgrades include new bathroom vanities, toilets, flooring and fresh paint. Close to Interstate 91 and 15 minute commute to White River and West Lebanon where you can run errands. Easy access to the highway to zip down to Boston and New York City. Dartmouth Hitchcock Hospital with a trauma center is within 30 minutes. Close to many dining options, retail shopping, outdoor adventures on the Connecticut River, a historic downtown area, colleges, airports, breweries, distilleries, dispensaries, country clubs, golf courses, Mt. Ascutney, and all the things! Don't delay, set up a viewing today.

This property is the perfect fit if you are new to home ownership and would like to have a portion of your mortgage paid monthly. The main home is 3 bedrooms, 3 bathrooms, new deck, spacious yard, and updated appliances. The 1 bedroom unit has a nice enclosed porch, adding seasonal living space, and has been renovated. There is also storage space above that could be added to this unit. In the last 10 years, the roof, windows, and heating system were all updated. In the last 2 years, a new hot water heater, appliances and gutters have been done. This is as move in ready as any home could be! And, let's not forget the additional lawn mower /toy garage and detached oversized 1 car garage. Easy Route 5 access to I-91.

Built in 1796, the historic Trask House is located on beautiful Main St. in the heart of downtown Windsor. The center hall Federal sits on just under 1/2 acre and has an attached barn/garage in the back with plenty of storage. There is a private brick patio surrounded by a white picket fence and lovely landscaping. Inside, you are greeted by large open rooms with hardwood floors, high ceilings, and multiple fireplaces. The updated kitchen is open to the dining room with a wood burning stove centered between the two rooms. The dining room leads to the stunning living room with picturesque alcoves and original Federal style millwork and mantels. Across the hall are the family room and a quaint library which ultimately connects back to the kitchen. A grand center hall stair case leads upstairs to 4 good sized bedrooms, a full bath and the laundry room. The Trask House is in an ideal location just minutes from Lake Runnemede, restaurants and stores, and Mt. Ascutney Hospital. Woodstock, Hanover, and the Upper Valley are approximately 25 minutes away. The Trask House is in the National Registry of Historic Homes and has been featured in numerous books on historic homes of New England. Come take a look!

Welcome to this exquisite four-bedroom, two-bathroom Colonial home, built in 1801, nestled on a sprawling 10.4-acre lot in Windsor, Vermont. This charming residence boasts maple and bamboo floors as well as original wide pine flooring, spacious bedrooms, and tiled bathrooms. The property includes a two-bedroom, one-bathroom ADU, perfect for generating rental income or accommodating guests. Enjoy the serene rural setting with level land ideal for animals, fenced pastures, and extensive perennial gardens. Outdoor amenities include a glamping site over the barn, RV hookups, an in-ground pool, and a tranquil majestic pond surround by natural iris that bloom every spring. Recent updates blend historic charm with modern appointments, maintaining the home beautifully for 30 years under the same owner. Located close to local amenities, this home offers both seclusion and convenience. Additional features include outbuildings and an animal barn, providing ample storage and versatile use. Don't miss this unique opportunity to own a piece of Vermont history with endless potential.

Fox Penny Farm, an established horse farm on 62 acres of open fields, trails, and woods on the Windsor/West Windsor line with westerly views of Mt Ascutney, is now offered for sale. Offering an expansive 3-bedroom 2.5 baths colonial with light-filled spaces, hardwood floors, spacious kitchen, dining room & propane fireplaced living room. Upstairs provides three large bedrooms with a primary ensuite. The lower level offers a partially finished living area with a wood stove and French doors leading to a private deck. Complete with 36x50 5-stall barn, 1000 bale hay storage heated tack room, and wash stall. Multiple run-in sheds, fenced paddocks, 100’ x 200 outdoor arena, equipment shed, and workshop with woodstove, all on open flat land. Fully wired generator servicing the house, barn, and outbuildings. Easily adaptable for farming pursuits. Prime location for hiking, biking, and skiing. Easily accessible to Woodstock & the Upper Valley. A special property that must be seen to appreciate all the possibilities.