65360 Homes under $500,000

Welcome to Windsor, Missouri, a charming town located in the heart of the Show-Me State, with the zip code 65360. Known for its friendly community and picturesque landscapes, Windsor offers a perfect blend of small-town charm and modern conveniences. Whether you’re a first-time homebuyer or looking to downsize, Windsor has an array of beautiful homes available under $500,000, making it an ideal destination for those seeking affordable living without compromising on quality.

Windsor is rich in history and community spirit, boasting a variety of local amenities, including parks, shops, and dining options that cater to all tastes. The town is surrounded by stunning natural beauty, offering plenty of outdoor recreational activities such as fishing, hiking, and picnicking, perfect for families and nature lovers alike.

The housing market in Windsor is diverse, featuring cozy single-family homes, spacious ranch-style properties, and charming bungalows, all priced below $500,000. Many of these homes come with generous lots, allowing for outdoor space that is perfect for gardening, entertaining, or simply enjoying the serene environment.

With excellent schools and a strong sense of community, Windsor is not just a place to live; it’s a place to thrive. If you’re looking to invest in a home that offers both value and a welcoming atmosphere, Windsor, MO, with its affordable housing options, is the perfect place to call home. Discover your dream home in this delightful town today!

Newest 65360 Homes under $500,000

$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.

$147,250

2 Beds ⋅ 1 Baths

Welcome to 102 Center St in Windsor! This beautifully updated 2-bedroom, 1-bath home offers 1,081 sq ft of completely refreshed, move-in-ready living space. With an extensive top-to-bottom remodel already completed, you can move in and enjoy the home without worrying about a long list of projects. Updates include fresh interior and exterior paint, new luxury vinyl plank flooring throughout, new light fixtures, new appliances, granite countertops, new cabinets, new tiled backsplashes and bathroom features. The kitchen feels fresh and modern while still offering a practical layout for everyday living. Outside, the durable metal roof and all brand new windows add another layer of worry-free ownership, while the large attached carport provides plenty of covered parking and includes an attached storage room for tools, lawn equipment, or additional storage. If you're looking for an affordable, low-maintenance, completely remodeled home that's truly ready to go, this one deserves a look!

102 Center Street, Windsor

Listing courtesy of Logan Kirchhoff of Re/Max United.

$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.

$95,500

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.

$89,900

1 Beds ⋅ 1 Baths

This charming one-bedroom, one-bath ranch is conveniently located near downtown Windsor for easy access. It’s wheelchair accessible, with ramps at both the front and back entrances. Recent updates include new electrical, plumbing, siding, roof, water heater, HVAC, and flooring. Situated on a spacious corner lot with mature trees, the home stays comfortable year-round thanks to an efficient all-electric mini split system.

105 E Colorado Street, Windsor

Listing courtesy of Karen Godfrey of Keller Williams Platinum Prtnr.

$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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