$157,351Average Value$118Average Price per Sq Ft18Homes For Sale
Hiking, the Amish and Air Force base proximity define Windsor
Windsor has been a rural crossroads since the mid-1800s, when the railroad was built. Though the railroad no longer operates, the tracks now form the intersection of the Rock Island Trail and the Katy Trail. “Those are part of the longest rail-to-trail project in the country, so a few active people who move here every year,” says Robin Burtchett, a lifelong Windsor local and the owner-broker of Windsor Realty. Home to roughly 3,000 residents, the community lies about 16 miles south of Whiteman Air Force Base and is surrounded by farmland, much of which is owned by a small Amish population. This convenient and peaceful location brings military families and base employees to town. “We get a lot of relocators looking for a nice small town outside the base, and that’s exactly what Windsor is,” Burtchett says. “Besides a few annual community events, not much happens here.”
Katy Trail State Park stretches over 240 miles across central Missouri.
Whiteman Air Force Base is a major employer located north of Windsor.
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Homes line gridded streets and rural roads
Housing includes cottages, ranch styles and New Traditionals. Oak and cedar trees typically shade lawns, with the median lot size at a little over a quarter acre. Roads near the center of town follow a grid pattern, and some streets on the outskirts are gravel. Smaller homes and fixer-uppers can go for $25,000 to $140,000, while larger homes typically fall between $150,000 and $300,000. Properties with more land can start at around $540,000 and reach up to $800,000. The median single-family home price is around $156,000, significantly lower than the national median. Tornadoes can impact the area, and sirens are tested on the first Wednesday of each month.
Older homes occupy spacious lots in Windsor.
New traditional homes can be found in parts of Windsor.
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Hikers and bikers sometimes stay the night in Windsor
The 47-mile Rock Island Trail links with the 240-mile Katy Trail near the heart of Windsor. Both gravel paths follow former railroad corridors, with the Katy Trail stretching from Clinton to Machens. Hikers and bicyclists often rest at cabins, campgrounds and motels in town. “Every once in a while, we get a huge group that passes through,” Burtchett says. “They usually only stay for a night, but it’s always fun to hear their stories if you run into them at a local restaurant.” A reservoir built to fuel steam trains now anchors Farrington Park, Windsor’s largest green space. Today, people visit to fish off the shoreline and use the waterfront disc golf course. It also hosts community events, like the Fourth of July fireworks show and the Christmas light display. Harry S. Truman State Park, about 26 miles south, has boat launches, a beach and a marina on Truman Lake.
A tree carving pays tribute to the area's native history at Farrington City Park.
Farrington City Park is centered around a small lake.
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The Amish operate bulk stores and a produce auction nearby
Brothers Market is a grocery store near Windsor’s core, but locals often choose to shop at the Amish markets on the outskirts of town. “Honestly, they have a better selection of stuff sometimes,” Burtchett says. Spices, beans and honey stock the shelves at places like Kuntry Bulk Grocery and Lilac Lane Bulk Foods. The Amish also operate the Four County Produce Auction between April and October. “It’s wholesale produce, so people will go to stock up on things they want to can or pickle,” Burtchett says. A post office and a few locally owned restaurants fill Windsor’s small downtown district. Furniture, glassware and books are on sale at The Pour Poet, an antique store and coffee shop. Pickled Possum is a dive bar regularly hosting Chiefs watch parties and pool tournaments.
Lilac Lane Bulk Foods offers a variety of products and homewares north of Windsor.
Windsor residents can buy, sell or trade produce at the 4-County Produce Auction.
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Windsor schools offer support for military families
Henry County R-I School District serves Windsor. Kids can attend Windsor Elementary from prekindergarten through sixth grade before continuing to Windsor High for seventh through 12th grade. Both schools earn C grades from Niche. The district supports military families with special liaisons and a transition program to help new students adjust.
Windsor Elementary School is part of the Henry County Public School District.
Windsor High School has an average enrollment of around 330 students.
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Cars may share the road with horse-and-buggies
Windsor is convenient for hikers, bikers and drivers, though they may share the road with Amish people traveling by horse-and-buggy. State Route 23 reaches Whiteman AFB, which employs around 8,000 people. Flight paths do go over Windsor, and locals sometimes hear routine aircraft training. A 26-mile drive northeast on state Route 52 and U.S. Route 65 leads to Sedalia, home to more stores, restaurants and the Bothwell Regional Health Center. Kansas City International Airport is about 90 miles northwest.
Windsor revolves around SeptemberFest on Labor Day weekend
The Miss Windsor Pageant kicks off SeptemberFest every Labor Day weekend. “All of Windsor basically revolves around the festival from Thursday to Sunday,” Burtchett says. The town’s fairground has a carnival with a Ferris wheel, a fun house and face painting booths. Veterans, firefighters and Windsor High alums participate in the parade through downtown. First Christian Church offers miniature train rides, and musicians perform outside Pickled Possum some nights. There’s also a 5K on Rock Island Trail, a cornhole tournament and a tractor pull.
Written By
Meghan Baker
Photography Contributed By
Kenyon Gerbrandt
Video By
Chris Freeman
Interested in learning more about homes in this area?
Reach out to
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an experienced agent in this area.
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On average, homes in Windsor, MO sell after 68 days on the market compared to the national average of 57 days. The median sale price for homes in Windsor, MO over the last 12 months is $155,000, up 10% from the median home sale price over the previous 12 months.
Charming single-family home situated on a spacious city lot in the heart of Windsor. This inviting property offers 3 bedrooms, 1.5 bathrooms, and a comfortable layout featuring a bright living and dining area with a large picture window. The oversized kitchen provides plenty of space for cooking and gathering, while the family room offers additional room to relax or entertain. Enjoy the fenced
Charming single-family home situated on a spacious city lot in the heart of Windsor. This inviting property offers 3 bedrooms, 1.5 bathrooms, and a comfortable layout featuring a bright living and dining area with a large picture window. The oversized kitchen provides plenty of space for cooking and gathering, while the family room offers additional room to relax or entertain. Enjoy the fenced
So much to love about this charming story and a half home located on a corner not. You will feel at home the minute you move in. There are two bedrooms and one bath on the main level and an amazing master suite on the upper level boasting, large closets, and plenty of room for a king size bed. Also, on the upper level is a bonus area perfect for an office, TV room, playroom.....the possibilities
Investment Opportunity~Great chance to own a well maintained 2 bedroom, 1 bathroom home perfect for rental income. Looking to build investment portfolio, this one is for you. This property features a functional layout, solid construction and has been well cared for over the years. The highlight of the property is the 30x30 shop, offering plenty of space for storage, workshop use, hobbies or
This is the newest subdivision in Windsor, There is a private lake for owners to fish, boating, and walking trail around the lake. We have several lots to choose from, you can have a lake view or lake front.
Storage outbuilding. Handicap ramp not included. Potential RV hookup area and parking, Room for a garden. Space for chickens. Workshop potential. Small-town living. Low traffic.
This charming one-bedroom, one-bath ranch is conveniently located near downtown Windsor for easy access. It’s wheelchair accessible, with ramps at both the front and back entrances. Recent updates include new electrical, plumbing, siding, roof, water heater, HVAC, and flooring. Situated on a spacious corner lot with mature trees, the home stays comfortable year-round thanks to an efficient
Don't miss this great opportunity to own an affordable 3 bedroom home in the charming community of Windsor. This well maintained home offers comfortable on level living with hardwood and tile flooring throughout for a modern look and easy maintenance. The home also features a newer water heater, an attached garage and functional floor plan that's perfect for first time home buyers, downsizes, or
Welcome to your forever home build site in the Knob Noster School District! This property has unobstructed views of the countryside on a corner lot in the Prairie Acres subdivision. Approx 5 miles from Whiteman AFB. Rural water and electric on site. Owner will sell connected property to total 9.32 acres if buyer desires more space to roam!
Welcome to 300 E Florence St, Windsor! This beautifully renovated 2-bedroom, 1-bath bungalow is the perfect place to call home. Completely updated in 2025, this charming residence features over 1,100 sq ft of comfortable living space. Enjoy cooking in a modern kitchen with elegant granite countertops, and relax in freshly painted, sunlit rooms that radiate warmth and style. Set on a spacious lot,
LOCATION! LOCATION! LOCATION! A little piece of land with BIG OPPORTUNITY for an entrepreneur with a vision or a dream! This lot borders the parking lot of the Katy Trail in Windsor and has 2 grain bins located on the property. The Katy Trail & The Rock Island Trail intersect in Windsor. Lots of Bike traffic and opportunity to create your dream business. I think of the saying from the movie Field
Amish-built 4 bedroom, 2 bath home on 3± fenced acres with excellent potential for customization. Property includes a 40×50 fully insulated, concrete-floored shop ideal for woodworking, equipment storage, or conversion to other uses. Additional features include a chicken coop, garden space, and fruit orchard. Home currently has no electricity or HVAC, offering a blank slate for buyers wanting to
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