Windsor Homes under $200,000

Welcome to Windsor, Missouri, a charming small town nestled in the heart of Henry County. Known for its friendly community and picturesque landscapes, Windsor offers a unique blend of rural charm and modern conveniences. With a population of just over 2,500 residents, this quaint city is the perfect place for those seeking a peaceful lifestyle without sacrificing access to essential amenities.

Windsor boasts a rich history and a tight-knit community atmosphere, making it an ideal location for families and individuals alike. The town is surrounded by beautiful parks and recreational opportunities, including the nearby Truman Lake, which is perfect for fishing, boating, and enjoying the great outdoors. With its vibrant local shops, cozy cafes, and community events, Windsor provides a warm and welcoming environment for all who call it home.

For prospective homeowners, Windsor is an excellent choice, especially for those looking for affordable housing options. The real estate market here features a variety of charming homes priced under $200,000. Whether you’re a first-time buyer or looking to downsize, you’ll find an array of options that cater to your needs. From cozy bungalows to spacious family homes, there’s something for everyone in this lovely town.

With its affordable housing, friendly community, and stunning natural surroundings, Windsor, MO, truly embodies the essence of small-town living. Come discover your dream home in Windsor, where comfort and community await you!

Newest Windsor Homes under $200,000

$180,000

3 Beds ⋅ 1 Baths

Move-in ready and well-maintained 3 Bed / 1 Bath home! Beautiful hardwood flooring runs throughout the living room and bedrooms. All kitchen appliances stay. Washer/Dryer stay. Home boasts a brand NEW roof and newer energy-efficient windows. Relax on the covered patio overlooking the large, spacious yard. The full, unfinished basement is already stubbed for a bathroom, offering immediate potential to add finished square footage and equity! Short commute to Whiteman Air Force Base.

305 Hillcrest Drive, Windsor

Listing courtesy of Jo Johnson of Old Drum Real Estate.

$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.

$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.

$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.

$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.

$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.

$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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