Windsor Vermont MLS Listings Homes For Sale with 4 or more Bedrooms

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You are viewing Windsor VT Homes with 4 or more Bedrooms between $0 and $30000000 dollars.

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WINDSOR VT Home for sale $$195,000 | $49 per sq.ft.

$195,000 | $49 per sq.ft. WINDSOR VT HOME FOR SALE

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.


WINDSOR VT Home for sale $$325,000 | $133 per sq.ft.

$325,000 | $133 per sq.ft. WINDSOR VT HOME FOR SALE

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.


WINDSOR VT Home for sale $$409,000 | $180 per sq.ft.

$409,000 | $180 per sq.ft. WINDSOR VT HOME FOR SALE
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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