Windsor Real Estate

Windsor Real Estate

Windsor, Missouri: A Hidden Gem in the Heart of the Midwest

Nestled in the heart of Missouri, the charming city of Windsor offers a peaceful and picturesque lifestyle for residents seeking a close-knit community atmosphere. Located in Henry County, this small town is known for its friendly locals, beautiful landscapes, and affordable real estate options.

Windsor boasts a rich history, dating back to the early 19th century. Originally a railroad town, it has since evolved into a thriving community with a strong sense of pride in its heritage. The city's historic downtown area is lined with well-preserved buildings, showcasing the architectural beauty of a bygone era.

For outdoor enthusiasts, Windsor is a paradise. The region is surrounded by stunning natural landscapes, including the scenic Truman Lake and the vast Katy Trail State Park. Whether you enjoy fishing, boating, hiking, or simply taking in the beauty of nature, Windsor provides ample opportunities for outdoor recreation.

When it comes to real estate, Windsor offers a diverse range of options to suit every budget and lifestyle. From charming historic homes to modern new builds, there is something for everyone. The cost of living in Windsor is also notably lower than in many larger cities, making it an attractive destination for those looking to invest in property or settle down.

In addition to its natural beauty and affordable housing, Windsor is also home to excellent schools, a tight-knit community, and a variety of local amenities. Residents can enjoy a range of dining options, boutique shopping, and community events throughout the year.

Whether you're a nature lover, history enthusiast, or simply seeking a peaceful place to call home, Windsor, Missouri, offers a unique blend of small-town charm and modern convenience. Come and discover the hidden gem that is Windsor, and find your perfect piece of real estate in this idyllic Midwest city.

Newest Listings in Windsor

$79,900
LOCATION! LOCATION! LOCATION! Discover endless possibilities with this versatile commercial storefront. Recently utilized as a salon and boutique, this property features a spacious layout including a large front room, private office, breakroom with kitchenette (plumbed for a shower), and a generous back room. Additional benefits include a full basement with 7-foot ceilings perfect for storage, and convenient off-street parking private parking in the back of the building ideal for owner use or convenient unloading. The building has been updated with new wiring, plumbing, sewer line, reinforced flooring, and the furnace is approx. 4-5 years old. Ideal for entrepreneurs seeking a turnkey space with great potential.

109 S Main Street, 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.
$135,500
2 Beds ⋅ 1 Baths
Investor special/ Equity builder! Solid 2 bed 1 bath home! This home would make a great rental or perfect starter home for someone looking to build some quick equity! It has a beautiful back yard, and lots of charm! The exterior has a new coat of paint! Schedule a showing today!

703 W Benton Street, Windsor

Listing courtesy of Kayla Rehkop of Rock Island Realty, LLC.
$100,500
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.
$70,000
Welcome to your forever home build site in the Knob Noster School District. This property has unobstructed countryside views in the Prairie Acres subdivision. Approx 5 miles to Whiteman AFB. Rural water and electric on site. Owner will sell connected property to total 9.32 acres if buyer desires more space to roam!

TBD SE 750 th Road, Windsor

Listing courtesy of Amanda Meyers of Optimum Realty Group LLC.
$70,000
Welcome to your forever home build site in the Knob Noster School District! This property has unobstructed views of the countryside on a corner lot in the Prairie Acres subdivision. Approx 5 miles from Whiteman AFB. Rural water and electric on site. Owner will sell connected property to total 9.32 acres if buyer desires more space to roam!

TBD SE 750TH Road, Windsor

Listing courtesy of Amanda Meyers of Optimum Realty Group LLC.
$599,900
This well-established tire and auto repair shop on large lot presents an excellent opportunity for an owner-operator mechanic seeking independence or an existing shop owner looking to expand with a proven second location. The business offers consistent cash flow, and established customer base and a turnkey operation with equipment already in place. The business and real estate are being sold together with an adjoining property that is currently used for storage. The additional property has potential for additional income source. The property includes 1232 sq ft main building and another 1512 sq ft in the building on the adjoining property. The combined lots are 12012 sq ft. Sale is subject to buyer due diligence. The location also offers close proximity to Clinton, Sedalia and Warrensburg, MO.

123 N Main Street, Windsor

Listing courtesy of Jennifer Ray of Platinum Realty LLC.
$164,900
3 Beds ⋅ 2 Baths
Cleaner-upper!!! Bring a little sweat equity and make this your storybook ranch on half an acre. Rare Find with that HUGE outbuilding/garage and apartment/office. The home hosts two bedrooms and a bath with hardwood floors, ample cabinet space in the open kitchen featuring a look through bar/window to living area and a gas stove and some updated systems. But wait, there is more, another bedroom and bath adjoin the garage, perfect for a private visitor stay, a teenage paradise or 2nd living space or income short term or long term rental. The half acre lot has been gardened with love and the home has been lovingly maintained over the years. There is an oversize two car garage and a huge shed (roughly the size of another two car garage) behind the garage. Bring the dog, the yard is fenced. Just blocks from the city park and lake and only a few minute drive to the quaint downtown Windsor, a must stop along the Katy Trail.

232 S County Line Road, Windsor

Listing courtesy of Brad Korn of EXP Realty LLC.
$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.
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