You are viewing Windsor VT Homes between $0 and $30000000 dollars.
$1,399,000 $350 per sq.ft. Windsor VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 4000 | Acres: 4.96Listed on Tuesday Jun 16, 2026
Description: "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dining room, with built-in cabinets and a second wood burning fireplace, connects to the kitchen which is open to the family room. A beautiful spindle staircase with oversized steps leads you upstairs to the four bedrooms, including the primary with an ensuite bath and an attached office. The main guest/children's bedroom features a magnificent turret style sunroom taking in views of the Connecticut River, and a second set of stairs leads back down to the mudroom. The full basement offers plenty of storage and all the utilities. The large 2 story garage offers room for 4 vehicles and plenty of storage on the 2nd floor. This unique property presents a rare opportunity to own a special homestead in the Windsor area, just minutes from downtown shopping and restaurants. See Listing Details & 50 images. Includes a Virtual Tour
$510,000 $103 per sq.ft. Windsor VT Home »
Price Change! Reduced by $25,000 down 5% on July 8th 2026
6 Beds | 4 Baths | Total Sq. Ft. 4933 | Acres: 0.48
Listed on Wednesday May 13, 2026
Description: Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch or enjoy the private yard and great living room that overlook the nearby pond providing a peaceful retreat at the end of a long day! See Listing Details & 36 images.
$442,999 $226 per sq.ft. Windsor VT Home »
Waterfront on Lake Runnenede3 Beds | 2 Baths | Total Sq. Ft. 1961 | Acres: 0.16
Listed on Friday Jul 17, 2026
Description: Open House Sunday July 26th 10a.m. - 12 p.m.! Single Family or Duplex! Live in it as a spacious 3 bedroom, 2 bath single family home, or take advantage of the current setup as two separate 1 bedroom units, each with its own utilities. That kind of flexibility is hard to find, whether you're thinking multigenerational living, rental income, or just extra breathing room. And then there's the view. Gorgeous lake views greet you from inside this home, the kind that make you stop and appreciate where you live every single day. This is a true Victorian, full of the character and detail that newer homes just can't replicate. The full basement includes a bonus room, perfect for a home office, workshop, or extra storage. A detached garage adds even more convenience for parking and yard equipment. Tucked into charming Windsor, you're close to 91 and just minutes from local shops and restaurants downtown. Homes with this much versatility and this kind of view don't come along often. See Listing Details & 45 images.
$229,000 $227 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1008 | Acres: 0.08Listed on Thursday Apr 23, 2026
Description: Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs. You are within walking distance to the Amtrak station and downtown, and our local Moover public transit service is ready to help. The community hospital is just a shore drive as well. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this new construction is a great choice. See Listing Details & 10 images.
$225,000 $205 per sq.ft. Windsor VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1095 | Acres: 0.14Listed on Wednesday Jul 8, 2026
Description: Looking for an affordable way into homeownership? This ranch features 3 bedrooms and 1 full bath, this single-level home is perfect for first-time buyers or downsizers. Cozy up in the living room next to the fireplace or relax on the covered porch with your morning coffee. The easy, one-floor layout means low-maintenance living at a price that's hard to beat. Located just minutes from downtown Windsor's shops, restaurants, K-12 school, and Kennedys Pond, this home offers small-town charm with everyday convenience. Priced to sell at $225,000: Schedule your showing today. See Listing Details & 14 images.
$110,000 $458 per sq.ft. Windsor VT Home »
Price Change! Reduced by $9,000 down 8% on June 20th 2026
1 Beds | 1 Baths | Total Sq. Ft. 240 | Acres:
Listed on Monday Mar 16, 2026
Description: 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 in to 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 Listing Details & 26 images.
New Listing!
$109,000 $216 per sq.ft. Windsor VT Home »
1 Beds | 1 Baths | Total Sq. Ft. 504 | Acres: 0.04Listed on Wednesday Jul 29, 2026
Description: Why keep paying rent when you can own? This one bedroom just makes sense. Nothing overwhelming to maintain. A comfortable living space, a kitchen that works, and a bedroom to relax in. Outside you've got a yard that's easy to keep up with, and just enough space to enjoy. And the location can't be beat. Near downtown Windsor, grab dinner or coffee nearby, hop on 91 in minutes, or take a stroll along the Connecticut River. This is Vermont living without the price tag or the headache. Homes like this at this price point don't sit around, so come see it before it's gone! See Listing Details & 10 images.
