Windsor Homes under $500,000

Welcome to Windsor, Missouri, a charming town that perfectly blends small-town warmth with modern amenities, making it a fantastic place to call home. One of the standout features of this community is its highly regarded school district, which is dedicated to providing quality education and fostering a supportive learning environment for students of all ages. The Windsor School District boasts a range of programs designed to cultivate academic excellence, promote extracurricular involvement, and encourage personal growth. With dedicated educators and a strong community focus, parents can feel confident that their children are receiving a top-notch education.

As you explore the housing market in Windsor, you'll find an impressive selection of homes available for under $500,000. This makes it an ideal area for families, first-time homebuyers, or anyone looking to invest in a welcoming community without breaking the bank. From charming single-family homes with spacious yards to modern townhouses that offer low-maintenance living, there’s something for everyone in Windsor.

Living in Windsor means enjoying a peaceful lifestyle while remaining close to the conveniences of urban life. With local parks, recreational facilities, and a friendly downtown area, residents can enjoy outdoor activities and community events year-round.

If you're searching for a place that combines excellent educational opportunities with affordable housing, Windsor, Missouri, is the perfect destination. Come discover your dream home in this delightful town, where community spirit and quality living await you!

Newest Windsor 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.

$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.

$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.

$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.

$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.

Start Your Search

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