$156,116Average Value$116Average Price per Sq Ft21Homes 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
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On average, homes in Windsor, MO sell after 65 days on the market compared to the national average of 58 days. The median sale price for homes in Windsor, MO over the last 12 months is $152,950, up 4% from the median home sale price over the previous 12 months.
Find your Forever Home in Windsor! This home which sits on a spacious corner lot within city limits of Windsor, has 2 bedrooms and 1 bath, a detached garage, walnut and patio peach trees, and plenty of possibilities at a reasonable price. The HVAC system inside and out are less than a year old. Washer and dryer will stay. Don't sleep on this one! Call and book your showing TODAY!
Welcome to this spacious, well-maintained home offering 4 bedrooms and 2 full bathrooms on an oversized lot. The motivated sellers have taken exceptional pride in this property and it shows. The open concept layout includes a fully remodeled en-suite bathroom in 2025. Outside you'll find an impressive detached shop with concrete floors, electricity, and an RV hook-up ideal hobbyist or anyone
Charming and move-in ready 3-bedroom, 1-bath home located on a quiet street! This well-maintained property features newer flooring throughout and a spacious living room highlighted by a large window that fills the space with natural light. The eat-in kitchen offers great functionality, newer wood top cabinets, and all appliances stay, including a refrigerator and dishwasher that are less than two
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
Beautiful 4 bed, 1.5 bath two-story home full of timeless character, ideally located just five blocks from downtown Windsor. Enjoy relaxing on the large wraparound covered front porch, perfect for morning coffee or evening unwinding. Inside, you’ll find huge new replacement windows that flood the home with natural light, highlighting the original window and baseboard trim that showcase its
Charming home with great updates and plenty of space to enjoy both inside and out! This property features new gutters and siding along with energy-efficient solar panels. The large yard offers endless possibilities for outdoor activities, gardening, and entertaining. Enjoy the added bonus of two insulated sheds with heating and cooling, perfect for hobbies, workspace, or storage. Additional
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,
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.
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.
Welcome to your dream property just 10 minutes South of Whiteman AFB! We are proud to offer multiple parcels ranging in size from 13.14 acres to 29.9 acres. Whether you’re wanting a property to fence for livestock, looking for a large lake, or just looking to build out in the country where its a little quieter and the pace is a little slower, we have a tract of land for you! You will be pleased
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!
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