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404 olive Street, Windsor
$390,000
4 Beds ⋅ 3.5 Baths
Space, comfort, and updates throughout! Situated on a one-acre lot, this 4,120-square-foot home offers four bedrooms, a nonconforming room with potential for a fifth bedroom, and three and a half bathrooms. A beautiful sunroom provides the perfect place to unwind, while the newly updated kitchen features granite countertops. Fresh paint throughout, new bathroom hardware, and abundant closet space add to the home’s appeal. Recent improvements include a new HVAC system, new water softener, two new water heaters, and new front windows. A new washer and dryer stay with the home! Outside, enjoy a large fenced backyard with plenty of room for outdoor activities, plus an in-ground sprinkler system. With generous living space and so many updates, this home has plenty to offer! (More pictures to come)

404 olive Street, Windsor

Listing courtesy of Johnele Mcbride of Signature RE Brokerage LLC.

423 Olive Street, Windsor
$175,000
2 Beds ⋅ 2 Baths
Welcome to 423 Olive Street! This beautifully updated 2-bedroom, 2-bathroom home offers comfortable living, modern improvements, and a desirable location on a wonderful street. The home has been thoughtfully renovated throughout, including a newly finished primary bathroom, flooring, paint, fixtures, and more. Major improvements include a newer roof, HVAC system, and water heater, providing peace of mind for the next owner. Situated on a generously sized lot, this property offers plenty of room to enjoy the outdoors while still being conveniently located next to all your town amenities. With its inviting curb appeal, extensive updates, and move-in ready feel, this home is a wonderful opportunity for anyone! Call today to schedule your showing!

423 Olive Street, Windsor

Listing courtesy of Danielle McQuillen of Platinum Realty LLC.

940 NE 981 Road, Windsor
$415,000
3 Beds ⋅ 2 Baths
Located in Henry County, Missouri, this 5-acre property combines country living, recreational opportunities, and a convenient location. Situated less than one mile from Highway 52 between Calhoun and Windsor, the property features a completely remodeled three-bedroom, two-bathroom farmhouse, a large metal outbuilding with stalls, established trails, mature walnut timber, and a wet-weather creek. The remodeled farmhouse offers comfortable rural living with spacious front and back porches overlooking the surrounding acreage. Whether enjoying a quiet evening outdoors or entertaining guests, the home provides a welcoming setting with room to enjoy the countryside. A large metal outbuilding with multiple stalls provides space for livestock, equipment storage, workshop activities, or other agricultural needs. The five acres offer opportunities for a small hobby farm, homesteading, or recreational use without the maintenance demands of a larger property. Established trails wind throughout the acreage, providing access to the wooded portions of the property. A wet-weather creek adds character to the landscape, while mature timber creates opportunities for outdoor recreation and wildlife activity. Numerous walnut trees are scattered throughout the property, offering potential future timber value depending on market conditions and tree quality. Despite its rural setting, the property provides convenient access to nearby communities. Windsor is approximately 10 minutes away, while Clinton is approximately 15 minutes away, offering shopping, dining, and additional amenities. With a remodeled farmhouse, functional outbuilding, mature walnut timber, trails, and a wet-weather creek, this Henry County acreage offers a combination of residential, agricultural, and recreational possibilities in west-central Missouri.

940 NE 981 Road, Windsor

Listing courtesy of Cajun Bradley of Whitetail Properties Real Esta.

225 S County Line Road, Windsor
$345,900
3 Beds ⋅ 3 Baths
Welcome home to this spacious, well-maintained, all-brick home situated on a rare 1.53-acre lot within walking distance to the city park! The main level boasts a formal living and dining combo, a generous family room with a cozy wood-burning fireplace, and an all-season sunroom perfect for relaxation. The kitchen features custom-built oak cabinets, additional built-in storage, granite countertops, stainless steel appliances, a gas stove, double oven, and built-in dishwasher. Enjoy the full, partially finished walk-out basement offering endless potential for expanded living space. Rare find with ample parking and storage—includes both a 2-car attached garage and a 2-car detached garage, plus a lawn/garden shed in the massive yard. A solid, quality-built home with space to stretch out inside and out! Short commute to Whiteman Air Force Base

225 S County Line Road, Windsor

Listing courtesy of Jo Johnson of Old Drum Real Estate.

109 S Main Street, Windsor
$79,900
LOCATION! LOCATION! LOCATION! Discover endless possibilities with this versatile commercial storefront. Recently utilized as a salon and boutique, this property features a spacious layout including a large front room, private office, breakroom with kitchenette (plumbed for a shower), and a generous back room. Additional benefits include a full basement with 7-foot ceilings perfect for storage, and convenient off-street parking private parking in the back of the building ideal for owner use or convenient unloading. The building has been updated with new wiring, plumbing, sewer line, reinforced flooring, and the furnace is approx. 4-5 years old. Ideal for entrepreneurs seeking a turnkey space with great potential.

109 S Main Street, Windsor

Listing courtesy of Jo Johnson of Old Drum Real Estate.

123 N Main Street, Windsor
$599,900
This well-established tire and auto repair shop on large lot presents an excellent opportunity for an owner-operator mechanic seeking independence or an existing shop owner looking to expand with a proven second location. The business offers consistent cash flow, and established customer base and a turnkey operation with equipment already in place. The business and real estate are being sold together with an adjoining property that is currently used for storage. The additional property has potential for additional income source. The property includes 1232 sq ft main building and another 1512 sq ft in the building on the adjoining property. The combined lots are 12012 sq ft. Sale is subject to buyer due diligence. The location also offers close proximity to Clinton, Sedalia and Warrensburg, MO.

123 N Main Street, Windsor

Listing courtesy of Jennifer Ray of Platinum Realty LLC.

709 W Benton Street, Windsor
$138,000
3 Beds ⋅ 1 Baths
Charming and well-maintained home situated on a spacious corner lot, offering a fantastic opportunity for homeowners or investors alike! This 3-bedroom, 1-bath residence features numerous updates, including a HVAC, electrical system, PEX plumbing, blown-in attic insulation, water heater, and installed gas line. Step inside to a freshly painted interior that creates a bright, clean, and move-in-ready feel. The living room showcases beautiful hardwood flooring, adding warmth and character, while all bedrooms feature luxury vinyl plank (LVP) flooring for a stylish and durable finish. The kitchen offers abundant cabinetry, delivering ample storage for all your cooking and organizational needs. Additional highlights include a detached garage located at the rear of the property, ideal for parking, storage, or a workshop. Previously a successful rental, this property presents excellent potential as an investment opportunity or a comfortable primary residence with versatile space.

709 W Benton Street, Windsor

Listing courtesy of Karen Godfrey of Keller Williams Platinum Prtnr.

300 E Florence Street, Windsor
$142,900
2 Beds ⋅ 1 Baths
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, the property offers plenty of room for outdoor living and gardening, giving you the perfect opportunity to create your own backyard oasis. Whether you’re a first-time buyer or looking to downsize, this delightful bungalow is move-in ready and brimming with potential. Don’t miss your chance to make 300 E Florence St your new address and turn your dreams into reality!

300 E Florence Street, Windsor

Listing courtesy of Jenna Kennedy of Re/Max United.

1193 SE 23 Highway, Windsor
$550,000
3 Beds ⋅ 3.5 Baths
Welcome to this beautifully custom built, partial earth contact home with 3-bed, 3.5-bathrooms filled with plenty of upgrades. Perfectly situated on 12 acres in Windsor, MO., this stunning residence boasts a variety of interior and exterior enhancements, offering modern comfort with timeless charm. Step inside to discover an inviting open floor plan with spacious ceilings throughout. The kitchen features granite countertops, custom cabinetry, a walk-in pantry, and stainless steel appliances, making it a perfect space for cooking and entertaining. The spacious living/dining area is filled with natural light, creating a warm and welcoming atmosphere with beautiful engineered hardwood flooring. The family room off the living area is so versatile, ideal for an office, mother in-law suite, or as a gameroom and sure to captivate your guests with endless entertainment. The master suite offers a private retreat with a spa-like en’suite bathroom featuring a walk-in shower, jacuzzi tub, and a generous walk-in closet. There is a laundry room and an additional bedroom on the main level. Upstairs you will find a sitting room, the 3rd bedroom, and another full bathroom. This bedroom walks out to a 2nd story deck. All bathrooms are custom tiled to enhance the theme throughout. Outside, you’ll find a wide-open yard, a covered front porch, and an open patio for outdoor entertaining or relaxing. Fenced pasture allows for your livestock of choice. The property also features a small pond and dock. Exterior home upgrades include a 50 year composition roof, James Hardie fiber cement siding, and energy-efficient fiberglass/wood windows, ensuring durability and curb appeal. Matching the main home is a 2 car detached garage added within the last 4 years. Also included is a 20x30 workshop with concrete floor and a 30x40 barn for all your equipment - both with ample electricity! Nestled back in a quiet part of the property, well off the main road, this home is just minutes from Whiteman AFB.

1193 SE 23 Highway, Windsor

Listing courtesy of Jo Johnson of Old Drum Real Estate.

The data relating to real estate displayed on this website comes in part from the Heartland Multiple Listing Service database compilation. The properties displayed on this website may not be all of the properties in the Heartland MLS database compilation, or all of the properties listed with other brokers participating in the Heartland MLS IDX program. Detailed information about the properties displayed on this website includes the name of the listing company.

The information displayed on this page is confidential, proprietary, and copyrighted information of Heartland Multiple Listing Service, Inc. (“Heartland MLS”). Copyright 2026, Heartland Multiple Listing Service, Inc. Heartland MLS and the company represented by this website do not make any warranty or representation concerning the timeliness or accuracy of the information displayed herein. In consideration for the receipt of the information on this page, the recipient agrees to use the information solely for the private noncommercial purpose of identifying a property in which the recipient has a good faith interest in acquiring. Data last updated . Terms of Use

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