Windsor VT
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| Windsor Vermont Homes Special Searches | | | Windsor VT Other Property Listings For Sale |
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Under Contract
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$94,900 | $144 per sq.ft.
16 Day Street
2 Beds | 1 Baths | Total Sq. Ft. 660 | Acres: 0.18
"Highest & Best Offer" deadline for submission is 10am EDT, Friday 5/23. This property is eligible under the Freddie Mac First Look Initiative through 06/15/2025. This property is offered 'as is'. Seller has not occupied property therefore there are no 'disclosures' offered. Interior ceiling damage(s) caused by roof 'failure' but half of roof was covered with corrugated metal by previous owner. Mold/damaged sheetrock & insulation already removed. House 'froze' & was defrosted, no water damage, winterized & that is current condition of plumbing/HVAC. Garage is salvageable but will require framing/etc. repairs. See
MLS Property & Listing Details & 26 images.
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$139,000 | $579 per sq.ft.
505 Back Mountain Road
1 Beds | 1 Baths | Total Sq. Ft. 240 | Acres:
This beautifully crafted 2024 "Incredible Tiny Home," built by Amish artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built deck--perfect for converting into a sunroom--as well as a screened gazebo and a storage shed included in the sale. Located in a small, quiet park just 4 miles from I-91, this property offers both charm and convenience. If you've ever dreamed of owning a Tiny Home, this is your opportunity! See
MLS Property & Listing Details & 36 images.
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$195,000 | $49 per sq.ft.
70-74 State Street
5 Beds | 4 Baths | Total Sq. Ft. 4011 | Acres: 0.34
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. See
MLS Property & Listing Details & 4 images.
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Under Contract
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$256,500 | $208 per sq.ft.
21 Bavier Avenue
3 Beds | 1 Baths | Total Sq. Ft. 1232 | Acres: 0.13
Located near the end of a dead end street and also near Mill Pond, this home is convenient to where you need to go! There's a nice covered front porch as well as a detached 1 car garage. The interior features 3 bedrooms, formal dining room, a nicely sized living room and character and charm throughout. This property is definitely worth checking out! See
MLS Property & Listing Details & 26 images.
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Under Contract
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$269,000 | $204 per sq.ft.
10 McKenzie Drive
3 Beds | 2 Baths | Total Sq. Ft. 1320 | Acres: 0.13
Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charming entryway that opens to a cozy living room, perfect for relaxing evenings or entertaining guests. Gleaming hardwood floors flow through the entry and dining areas, adding warmth and character throughout. The spacious dining room connects seamlessly to a well-appointed kitchen, offering both functionality and charm. A conveniently located half bath on the main floor includes an integrated washer and dryer for added ease. From the dining area, step out to the back patio and take in serene views of the expansive backyard, ideal for outdoor gatherings, gardening, or summer barbecues. Upstairs, you'll find three comfortable bedrooms and a full bath, providing plenty of space for family or guests. Perfectly positioned between Mill Pond, Lake Runnenede, and the Connecticut River, this home offers a unique blend of tranquility and convenience. Enjoy a leisurely 15-minute walk to Main Street, where local shops and restaurants create a vibrant small-town atmosphere. Combining vintage charm with thoughtful updates, this Olde Windsor gem is ready to welcome its next chapter. See
MLS Property & Listing Details & 33 images.
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$325,000 | $133 per sq.ft.
358 US Route 5
4 Beds | 2 Baths | Total Sq. Ft. 2452 | Acres: 0.75
Charming Duplex in the Heart of Windsor - Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income--or a savvy investor seeking solid returns--this well-maintained property offers both comfort and cash flow. Each unit features 2 spacious bedrooms, 1 full bathroom, a bright living area, and a spacious kitchen, making it ideal for tenants or personal use. Separate utilities ensure ease of management and straightforward billing, while continued thoughtful maintenance enhances long-term value and efficiency. Just minutes from local shops, dining, and schools, this property offers small-town charm with big investment potential. Enjoy easy access to I-91 and nearby recreational opportunities including hiking, skiing, and kayaking/fishing. Whether you choose to live in one unit and let the other help pay your mortgage, or fully rent both for reliable income, this duplex is a rare find in a desirable location. Don't miss your chance to own this flexible and financially smart property in one of Vermont's most charming towns. Schedule your showing today! See
MLS Property & Listing Details & 36 images.
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Under Contract
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$329,000 | $200 per sq.ft.
1 Dorrance Street
2 Beds | 2 Baths | Total Sq. Ft. 1649 | Acres: 0.18
Open House 10/4/1025 11Am-1Pm. This lovingly maintained Cape-style home, perfectly set on a 0.18-acre corner lot. With 2 bedrooms, 1.5 bathrooms, a welcoming covered porch, and spacious basement, this home blends classic Vermont character with everyday comfort. The home has a standing seam roof and a brand new boiler, with timeless features such as built-in cabinetry, hardwood floors, and ample closet space. Bonus rooms on each floor add to its charm and flexibility. The two-car garage with attic storage offers plenty of room for vehicles, tools, and more. Inside, the traditional layout provides a functional, warm, and inviting flow but leaves room for adding your own personal touches. Enjoy the convenience of being within walking distance to local amenities like Kennedy's Pond and the Windsor Fairgrounds all while savoring the peace and space of your corner lot, ideal for gardening, play, or quiet relaxation. See
MLS Property & Listing Details & 41 images.
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Under Contract
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$399,900 | $238 per sq.ft.
58 Morningside Drive
3 Beds | 2 Baths | Total Sq. Ft. 1680 | Acres: 0.96
Welcome to this well-kept ranch home in the heart of Windsor, VT. Offering 3 bedrooms and 1.5 baths, this home provides a comfortable layout, perfect for everyday living. The spacious living room is bright and inviting, opening easily into the eat-in kitchen where there's plenty of room for family and friends to gather. This is what a true turnkey home looks like; new roof, windows, siding, decking, electrical, flooring, whole house generator, and beautiful new baths and kitchen complete with granite countertops. Boiler was replaced just before these owners purchased in 2016. Even the basement has potential to be fully finished if you need more living space or to have a workshop or home studio. Enjoy the convenience of a 2-car garage and a level lot that's ideal for gardening, pets, or outdoor entertaining. Single-level living makes this property easy to maintain, while the location offers quick access to Windsor's shops, restaurants, and local amenities. Whether you're looking for your first home, a place to downsize, or a Vermont getaway, this ranch is full of potential and ready for its next chapter. See
MLS Property & Listing Details & 28 images.
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$409,000 | $180 per sq.ft.
Price Change! reduced by $50,000 down 12% on October 11th 2025
96 Dairy Lane
4 Beds | 3 Baths | Total Sq. Ft. 2272 | Acres: 1.34
OWNERS SAY SELL before Winter. Check out the new PRICE! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont's natural beauty while being just minutes from town amenities, schools, and I-91. Inside, you'll find a traditional floor plan with spacious living and dining areas, a well-appointed kitchen, and plenty of natural light throughout. With this flexible layout, you can configure bedrooms on 1 or both levels. The basement is dry, and has ample finished space for an extra playroom or family room, including 1/2 bathroom. The expansive yard is ideal for gardening, play, or simply taking in the peaceful surroundings. With room to grow, work from home, or create the lifestyle you've been dreaming of, this Windsor gem is ready to welcome its next chapter. See
MLS Property & Listing Details & 38 images.
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$499,000 | $344 per sq.ft.
Price Change! reduced by $136,000 down 27% on October 7th 2025
3361 County Road
3 Beds | 3 Baths | Total Sq. Ft. 1452 | Acres: 10.18
Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen features custom oak cabinetry, granite counters and updated appliances. The living room has sweeping cathedral ceilings, hardwood walls, oversized windows, and a wood burning fireplace. There is a primary Bedroom ensuite, and a guest powder room off of the foyer mudroom complete with slate floors. Step out to a private iron balcony with Trex decking and spiral stairway accessing a stone terrace below complete with fire pit, water feature and screened gazebo. Upper level has a spacious loft area, and a second bedroom. The walk out lower level includes a third bedroom, studio/rec room (could accommodate overflow guests) and laundry, plus a wine or root cellar. Oversized two car garage with plenty of storage above. Located just minutes from I 91. Easy access to Upper Valley, DHMC, Woodstock, skiing and all recreation. See
MLS Property & Listing Details & 39 images.
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