Windsor Homes under $500,000

Windsor Homes under $500,000

Welcome to Windsor, Missouri – a charming gem nestled in the heart of the Midwest! Known for its friendly atmosphere and rich history, Windsor offers a delightful blend of small-town charm and modern conveniences. With a population that values community spirit, you’ll find local events, parks, and recreational activities that bring residents together.

Windsor is strategically located just a short drive from larger cities, making it an ideal spot for those who appreciate the tranquility of rural living while still having access to urban amenities. The town boasts a variety of local shops, eateries, and recreational facilities that cater to all ages, ensuring there's always something to do.

When it comes to real estate, Windsor shines brightly with its diverse housing options, particularly for those seeking homes under $500,000. Whether you're a first-time homebuyer, looking to downsize, or searching for a family-friendly abode, Windsor has something for everyone. From cozy bungalows to spacious family homes, the real estate market here is both affordable and appealing. Many properties feature beautiful yards, modern amenities, and are situated in peaceful neighborhoods.

Investing in a home in Windsor not only means securing a wonderful place to live but also becoming part of a vibrant community. The combination of affordability, a welcoming environment, and the charm of small-town life makes Windsor, Missouri, an excellent choice for your next home. Explore the possibilities today and discover why so many are proud to call Windsor home!

Newest Windsor Homes under $500,000

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.
12101 NE J Highway, Windsor
$450,000
4 Beds ⋅ 3 Baths
Seller financing offered! Bring your elbow grease and make your move today to this humble 9.6 acre slice of paradise! This all-brick ranch-style home offers plenty of space for you, while the two detached shops have plenty to offer for storage and work! Inside you'll find a generous kitchen with counters and cabinets to spare, a coffee bar and barstools, and even a beautiful planter window to bring nature right into the home. The brick fireplace flanks the dining area and ties it to the comfortable living room. Upstairs you have the master suite and 2 more bedrooms with a main bath, while downstairs offers a family room, utility room, and one more bedroom and bathroom, plus a secret storage space behind the murphy-door bookcase! Outside, the driveway wraps past the ~4 acre pond and connects the home to both shops! The front ~40x60 building was build just a year ago and features 14ft ceilings, 12ft doors on the ends, and two 10ft doors on the side. The back ~18x35 shop is only 11 years old, is powered, and has a 10ft door. Both have full metal siding and roofing and a concrete floor! Financing offered at seller's discretion. Contact agent for more details.

12101 NE J Highway, Windsor

Listing courtesy of Justin Dean of 1st Class Real Estate KC.
405 E Colt Street, Windsor
$79,900
3 Beds ⋅ 1.5 Baths
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 backyard with a concrete patio and convenient rear entry into the home. An attached front-facing 1-car garage adds everyday convenience to this well-maintained property.

405 E Colt Street, Windsor

Listing courtesy of Julie Newton of Elite Realty.
603 W Florence N/A, Windsor
$155,000
2 Beds ⋅ 1 Baths
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 additional rental potential. Located in a convenient area with easy access to town, this property has strong potential for steady income or future appreciation.

603 W Florence N/A, Windsor

Listing courtesy of Michelle Hoskins of Old Drum Real Estate.
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.
104 E Colt Street, Windsor
$111,000
4 Beds ⋅ 2 Baths
Charming 4 bedroom home with so many possibilities. This large home is perfect for a growing family who is looking for space for everyone. It would also make a great investment property, great for a rental or a flip opportunity. This 2 story home has all the charm, its just looking for a family or an investor to put a personal touch on it. Close to downtown Windsor and not far from WAFB.

104 E Colt Street, Windsor

Listing courtesy of Michelle Hoskins of Old Drum Real Estate.
200 N Mill Street, Windsor
$55,000
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 Of Dreams "If you build it.. they will come".

200 N Mill Street, Windsor

Listing courtesy of Jo Johnson of Old Drum Real Estate.
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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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