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!

Opportunity Knocks! This home is ideal for a builder, investor or new homeowner who can qualify for a conventional or construction loan. Sales prices includes a variety of building materials. The home appears structurally sound with a 3 zone hot water heating system, drilled well and public sewer. This property features an attached 1 car garage, 3 BR's, 1.5 baths, office, fireplaced LR /with hardwood floors, fully applianced kitchen, Shed and deck with gorgeous views of Mt Ascutney. Property is located 2 miles east of the Village of Brownsville - Home to "Ascutney Outdoors" Trails and Outdoor Center, Mt Ascutney Resort and the famous Butcher and Pantry Store. Immediate Occupancy.

Nicely located just walking distance to the school and town amenities. Nice level lot with home just waiting for you to make it your own. Three bedrooms and spacious main level.

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!

Nestled just off the main road, this charming split-level home offers the perfect blend of privacy and convenience. Located just moments from town, you'll enjoy the peaceful setting without sacrificing easy access to local amenities. The inviting living room features a large picture window, filling the space with natural light. The adjacent kitchen includes a cozy dining area, ideal for family meals. Just a few steps up, you’ll find three comfortably sized bedrooms and a full bath. The partially finished basement presents an excellent opportunity for a future rec room, home office, or gym. Outdoors, the home boasts spacious front and side yards, perfect for gardening, entertaining, or simply relaxing in your own serene environment. Whether you're starting a new chapter or looking to expand, this home offers the potential to customize and make it your own. Don't miss out on this perfect blend of privacy and proximity!

Step into the timeless charm of this well-maintained 1920s single-family home, nestled in the heart of Olde Windsor. As you enter through the welcoming front patio, you're greeted by a classic entryway that leads seamlessly into a cozy living room, perfect for relaxing or entertaining. There are beautiful hardwood floors in both the entryway and the dining room, creating a warm and inviting atmosphere. Continue through the living room into the dining area to discover a well-appointed kitchen. Conveniently located on the main floor, a half bath features an integrated washer and dryer for added functionality. Just off the dining room, step out onto the back patio, where you'll enjoy serene views of the expansive backyard—an excellent space for outdoor activities and summer barbecues. Venture upstairs to find three generously sized bedrooms and a full bath. Located centrally between Mill Pond, Lake Runnenede, and the Connecticut River, this residence offers a perfect blend of tranquility and accessibility. Enjoy a short 15-minute stroll to Main Street, where a vibrant array of local restaurants awaits. This home is a rare find, combining vintage charm with modern convenience in a sought-after neighborhood. Don’t miss the opportunity to make this enchanting property your own!

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 beautifully updated 4-bedroom, 2-bath New England Colonial, nestled in a friendly neighborhood, combines classic charm with modern convenience. Step inside to discover a warm and inviting oversized mudroom, seamlessly flowing into a bright kitchen featuring a custom island and an abundance of cabinetry for all your storage needs. Just off the kitchen, the graciously sized dining room is perfect for hosting large dinners and holiday gatherings. The main floor also includes a full bath and a laundry room. Upstairs, you'll find three bedrooms and 3/4 bath. A finished attic space includes an additional bedroom. Enjoy outdoor living on the newly expanded deck, perfect for summer barbecues or morning coffee. The paved driveway leads to a detached 2-car garage, ensuring plenty of parking. Located less than a mile from downtown Windsor and just steps away from the scenic Lake Runnenede and the trails of Paradise Park, this home offers the perfect blend of space and convenience. Don't miss your chance to own this delightful piece of history with modern updates. Schedule a tour today!

Step into timeless elegance with this grand Victorian home, beautifully situated on a charming in-town lot. This stately residence showcases stunning hardwood floors throughout, preserving its classic heritage while offering modern comforts. The spacious first-floor bedroom features an en suite bath, providing both luxury and convenience. A cozy fireplace adds warmth and character to the main living space, perfect for relaxing evenings. The home boasts a generously-sized walk-in pantry, ideal for storage and organization. An added bonus is the potential separate apartment, offering endless possibilities for rental income, guest accommodations, or an in-law suite. Completing the property is a two-car detached garage, providing ample storage and parking. This house will suit a buyer who hopes to fill it's halls, expand, or be a welcome haven for a family compound. Minutes into downtown Windsor, an easy jaunt to the K-12 school, and a stones throw away from the Recreation Center makes for flexibility if transportation is an issue. Come make this one your own!

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!