Windsor Vermont Real Estate

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.

OFFER DEADLINE: MONDAY 4/21/25 6pm Ready to start your real estate investment journey? This 3-bedroom home is the perfect opportunity for someone eager to build equity and willing to add their own personal touch. Upstairs, you’ll find three spacious bedrooms and a convenient half bath—ideal for families or future tenants. The eat-in kitchen is ready for your updates, offering a blank canvas to create the heart of the home. Picture cozy evenings gathered around the woodstove, a feature that not only adds warmth and ambiance but can also boost your property’s value and appeal, especially in Vermont’s colder months. The practical mudroom is a must-have for Vermont living, keeping the outdoors where it belongs and making daily life a breeze. Outside, the older garage still gets the job done, and there’s plenty of space for gardening or simply enjoying the fresh air. A picturesque stream runs along the property, adding a peaceful, natural touch. Outdoor enthusiasts will love being close to the Mt. Ascutney trails, while commuters will appreciate the easy access to I-91—making this location as convenient as it is scenic. Whether you’re looking for your first rental, a fix-and-flip, or a place to call home while you build sweat equity, this property offers endless potential. Don’t miss your chance to invest in a home with character, charm, and room to grow! Being sold as-is.

Ready for the next generation is this lovingly cared for New Englander. Nestled on a quiet side street in the heart of Windsor, VT, this classic 2-bedroom, 2-bath home offers both character and warmth. The inviting front porch welcomes you into a sunlit living space featuring hardwood floors, original woodwork, and large windows that let in plenty of natural light. The spacious kitchen boasts ample cabinet space, and a cozy dining area, perfect for gatherings. Upstairs, you’ll find two generously sized bedrooms and another full bath, providing comfort and privacy. Outside, the backyard offers a peaceful retreat with room for gardens, outdoor entertaining, or simply enjoying the Vermont seasons. Conveniently located near local shops, schools, and recreational opportunities, this home is just minutes from I-91 for easy commuting.

With fabulous curb appeal and a welcoming covered porch, this turn-key circa 1940 New England home beautifully blends timeless design with modern comfort. The open-concept kitchen and dining area flow seamlessly into spacious living areas, creating a warm and inviting atmosphere. Elegant features such as French doors, a fireplace with a classic brick hearth, and bay windows add character and sophistication throughout. Enjoy breathtaking eastern views that bring a sense of calm to your everyday routine—your morning coffee spot just got an upgrade. Conveniently located just 5 minutes from the interstate, this home offers an easy commute to the Upper Valley while providing a peaceful retreat to come home to.

Great Location! Well-Maintained! 4BR's Cape Full Basement with work bench, Many recent updates in the last three years, Rear deck, Garden area and Private backyard.

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 2nd floor has more ensuite bedoom options, a second living room and even a wet bar, or send your food up in the dumbwaiter. 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. Or...let's consider the potential for a home business or commercial opportunity with a change of use permit. 6 additional spaces in the back, add ample parking. 2-3 office spaces and a 1/2 on main level and excellent street visibility. Property is located in the CENTRAL BUSINESS DISTRICT. Come make this one your own!