Browse All Windsor MO Single Family Properties for Sale

Don't miss this great opportunity to own an affordable 3 bedroom home in the charming community of Windsor. This well maintained home offers comfortable on level living with hardwood and tile flooring throughout for a modern look and easy maintenance. The home also features a newer water heater, an attached garage and functional floor plan that's perfect for first time home buyers, downsizes, or anyone looking for an affordable place to call home. Enjoy small town living with the convenience of nearby schools, parks and local amenities.

307 Phelps Street, Windsor

Listing courtesy of Michelle Hoskins 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.

$118,000

3 Beds ⋅ 2 Baths

Welcome to this charming and affordable home. Amazing large lot complete with a single car garage. This well-maintained single-wide offers a comfortable and functional layout with 3 bedrooms and 2 full bathrooms. Roof has been recently replaced and the HVAC is newer as well! Enjoy peace of mind with a whole-house water filtration system. The property also features a single-car garage, adding convenience for parking, storage, or a workshop space. Inside, you’ll find a practical floor plan with a spacious living area, a cozy kitchen with ample cabinetry, and a private primary suite complete with its own bathroom. The additional bedrooms offer flexibility for guests, a home office, or hobbies. Situated in a quiet area near the high school with easy access to local amenities, this home is a fantastic opportunity to own at an affordable price point. Don’t miss your chance to make it yours! Home is being sold as an inheritance and as such will be AS-IS. Buyer to verify all measurements and claims.

309 N North Street, Windsor

Listing courtesy of Kerrie Shumate of Midwest Realty & Auction.

$189,900

3 Beds ⋅ 1 Baths

This could be it!! Updated Windsor home packed with value and ready for it's new owner. New siding, gutters, and even added insulation for improved efficiency!! Fresh interior updates including flooring, paint, and even some refreshed updates to the kitchen and bathroom! The primary bedroom offers brand new carpet for added comfort. Whether you’re a first-time buyer or looking to downsize,this home checks the boxes with some modern updates and small-town charm! Backs up to a Elementary School. Buyer or buyer's agent to verify sq ft, taxes and school information. Selling AS IS!

207 Phelps Street, Windsor

Listing courtesy of Logan Krogh of Realty ONE Group Esteem.

$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.

$205,000

4 Beds ⋅ 2 Baths

Step into this spacious 4 Bed, 2 Bath, split-entry home. A large covered front porch welcomes you in—perfect for relaxing mornings or evening unwinding. Inside, you’ll find a spacious eat-in kitchen with patio doors conveniently located to walk right out onto the back deck for entertaining or BBQing. The home boasts a HUGE master suite on the lower level, complete with a generous bedroom, full bathroom, and walk-in closet, accented by beautiful stained barn doors. This space could easily double as a rec room, second living area, or private retreat. Major updates bring peace of mind, including a brand new HVAC system and a roof that’s only 2 years old. Outside, the property truly shines with a HUGE backyard, a small fenced-in area perfect for pets, and even a chicken coop for those looking to enjoy a little country living. A large detached garage adds extra storage and workspace options. Conveniently located right across the street from the high school and a short commute to Whiteman Air Force Base.

305 North Street, Windsor

Listing courtesy of Jo Johnson of Old Drum Real Estate.

$160,000

3 Beds ⋅ 2 Baths

So much to love about this charming story and a half home located on a corner not. You will feel at home the minute you move in. There are two bedrooms and one bath on the main level and an amazing master suite on the upper level boasting, large closets, and plenty of room for a king size bed. Also, on the upper level is a bonus area perfect for an office, TV room, playroom…..the possibilities are endless. On the main level there’s plenty of room for your family to enjoy dinners in the large dining room and cooked together in the spacious kitchen. You will love how cozy the home feels with hardwood floors throughout. There’s plenty of storage in the basement with the potential of adding a third bathroom, which is already been started. You will love spending time outside, it will be hard to choose between spending time on the front porch or hanging out in the fenced in backyard around the fire pit. Definitely a house you won’t want to miss out.

401 E Jackson Street, Windsor

Listing courtesy of Michelle Hoskins of Old Drum Real Estate.

$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.

$550,000

3 Beds ⋅ 3.5 Baths

Welcome to this beautifully custom built, partial earth contact home with 3-bed, 3.5-bathrooms filled with plenty of upgrades. Perfectly situated on 12 acres in Windsor, MO., this stunning residence boasts a variety of interior and exterior enhancements, offering modern comfort with timeless charm. Step inside to discover an inviting open floor plan with spacious ceilings throughout. The kitchen features granite countertops, custom cabinetry, a walk-in pantry, and stainless steel appliances, making it a perfect space for cooking and entertaining. The spacious living/dining area is filled with natural light, creating a warm and welcoming atmosphere with beautiful engineered hardwood flooring. The family room off the living area is so versatile, ideal for an office, mother in-law suite, or as a gameroom and sure to captivate your guests with endless entertainment. The master suite offers a private retreat with a spa-like en’suite bathroom featuring a walk-in shower, jacuzzi tub, and a generous walk-in closet. There is a laundry room and an additional bedroom on the main level. Upstairs you will find a sitting room, the 3rd bedroom, and another full bathroom. This bedroom walks out to a 2nd story deck. All bathrooms are custom tiled to enhance the theme throughout. Outside, you’ll find a wide-open yard, a covered front porch, and an open patio for outdoor entertaining or relaxing. Fenced pasture allows for your livestock of choice. The property also features a small pond and dock. Exterior home upgrades include a 50 year composition roof, James Hardie fiber cement siding, and energy-efficient fiberglass/wood windows, ensuring durability and curb appeal. Matching the main home is a 2 car detached garage added within the last 4 years. Also included is a 20x30 workshop with concrete floor and a 30x40 barn for all your equipment - both with ample electricity! Nestled back in a quiet part of the property, well off the main road, this home is just minutes from Whiteman AFB.

1193 SE 23 Highway, Windsor

Listing courtesy of Jo Johnson of Old Drum Real Estate.

$325,000

3 Beds ⋅ 2 Baths

Custom built home, modern comfort meets country charm! Welcome home to this beautifully custom-built 3-bedroom, 2-bath residence perfectly situated on 1 peaceful acre. Designed for comfort and convenience, this all electric home offers a thoughtful, step-free layout-ideal for anyone seeking single-level living. Step inside and be greeted by an open-concept floor plan that flows effortlessly from the spacious living area to the custom kitchen featuring soft-close cabinetry, granite countertops, stainless steel appliances, a large pantry, lazy Susan and pull-out cabinets for ultimate functionality. The primary suite boasts a stunning custom tile shower, while both bathrooms are designed with quality finishes and attention to detail. Enjoy your mornings and evenings on the covered porch , overlooking a yard with plenty of space for a garden, pets and outdoor entertaining. The over sized 3 car garage (32x36) with painted floors provides ample room for vehicles, tools and storage. With no steps steps throughout the entire property, this home offers accessibility and ease of living, all while maintaining a beautiful, modern aesthetic. This is more than a house, it's a home built for comfort style and lasting quality.

106 W Lake Shore Drive, 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

Windsor Single Family Real Estate

Our website features the best real estate search for single family properties available in Windsor and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!