Windsor Homes under $350,000

Welcome to Windsor, Missouri, a charming small town where community spirit thrives and the beauty of the Ozarks surrounds you. Nestled in the heart of Henry County, Windsor offers a perfect blend of rural charm and modern conveniences, making it an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Windsor is known for its friendly atmosphere, vibrant local culture, and a strong sense of community. With a population that values connection, you’ll find plenty of opportunities to engage with your neighbors at local events, farmers' markets, and seasonal celebrations. The town is also home to beautiful parks, recreational facilities, and scenic trails, perfect for outdoor enthusiasts and families looking to enjoy nature.

For those considering a move to Windsor, you’ll be delighted to discover a variety of charming homes available for under $350,000. Whether you’re searching for a cozy starter home, a spacious family residence, or a charming bungalow, Windsor has something to suit every taste and budget. The real estate market here is not only affordable but also offers the potential for growth, making it an attractive option for first-time buyers and seasoned investors alike.

With its affordable housing options, welcoming community, and picturesque surroundings, Windsor, MO, is a hidden gem waiting to be discovered. Come explore the possibilities and find your dream home in this delightful town where every day feels like a breath of fresh air!

Newest Windsor Homes under $350,000

$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.

$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.

$205,000

1 Beds ⋅ 2 Baths

This charming one bedroom, two- bathroom home on a huge corner lot is ready for your personal touches! This well maintained home offers beautiful hardwood floors, stainless steel appliances, and a newer roof! Full basement with tons of potential. The back yard is really the show stopper, completely fenced in, large mature trees, and 2 sheds makes it the perfect place for a gardener!

706 W Benton Street, Windsor

Listing courtesy of Kayla Rehkop of Rock Island Realty, LLC.

$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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