Windsor Homes under $400,000

Windsor Homes under $400,000

Welcome to Windsor, Wisconsin—a charming community nestled in the heart of Dane County. Known for its picturesque landscapes and friendly atmosphere, Windsor offers a perfect blend of suburban tranquility and easy access to urban amenities. Just a short drive from the vibrant city of Madison, residents enjoy the best of both worlds: the peacefulness of small-town living with the excitement of city life right at their fingertips.

Windsor is a family-friendly area with excellent schools, lush parks, and a strong sense of community. Whether you're strolling through the scenic neighborhoods or enjoying a weekend at one of the local parks, you’ll quickly appreciate the welcoming spirit that defines this lovely town.

For those in search of a new home, Windsor boasts an impressive selection of properties priced under $400,000. This range offers an array of options, from charming single-family homes to modern townhouses, making it an ideal choice for first-time buyers, families, or anyone looking to invest in a vibrant community. With spacious yards, updated interiors, and proximity to local amenities, these homes provide a perfect setting for creating lasting memories.

The Windsor real estate market is thriving, and with properties at this price point, you can find a home that suits your lifestyle without breaking the bank. Discover the joys of living in Windsor, where community spirit flourishes, and your dream home awaits. Come explore what makes this delightful town a wonderful place to call home!

Newest Windsor Homes under $400,000

3976 Empire Dr, Windsor
$400,000
3 Beds ⋅ 2 Baths ⋅ 2035793 MLS ⋅ ACTIVE UNDER CONTRACT Status
Imagine stepping out into your own private oasis on over a half-acre of land. Complete with a fenced-in area perfect for morning fetch with the dog or weekend gatherings, this expansive outdoor space is built for a lifestyle of freedom and play. Inside, the home welcomes you with an open, airy main living area where the kitchen and great room boast dramatic vaulted ceilings, making the entire space feel bright and grand. The layout flows effortlessly into three main-level bedrooms, including a primary suite with private, direct access to the bath. As the weather cools down, your lifestyle extends to the walkout lower level, where a cozy fireplace anchors a spacious family room and a 3/4 bath—perfect for crisp autumn evenings. Incredible value with unlimited potential to add your personal touch and build equity.

3976 Empire Dr, Windsor
6661 Charlie Grimm Rd, Windsor
$349,500
3 Beds ⋅ 2 Baths ⋅ 2035112 MLS ⋅ ACTIVE Status
NOT YOUR COOKIE-CUTTER CONDO! This unique multi-level half-duplex offers character, style, and spacious living overlooking Lake Windsor Golf Course! Soaring vaulted ceilings and abundant natural light highlight the open living and dining areas, featuring a gas log brick fireplace. The versatile layout includes 3 bedrooms, a primary bedroom loft, generous dining room with deck access, and an eat-in kitchen with patio doors to a fenced backyard retreat. Enjoy the stamped concrete patio, fire pit, storage shed, and golf course views! Updates include stainless steel kitchen appliances, front-load stackable washer/dryer, vinyl plank flooring, carpeting, central air, windows, and patio doors. Features include first-floor laundry, a 2-car garage, Ring doorbell and security system. Conveniently located near Lake Windsor Country Club and Windsor Athletic Club, with easy access to Madison, I-39/90/94, and Dane County Regional Airport. Unique style and space make this home a must-see!

6661 Charlie Grimm Rd, Windsor
6661 Charlie Grimm Rd, Windsor
$349,500
3 Beds ⋅ 2 Baths ⋅ 2034794 MLS ⋅ ACTIVE Status
NOT YOUR COOKIE-CUTTER CONDO! This unique multi-level half-duplex offers character, style, and spacious living overlooking Lake Windsor Golf Course! Soaring vaulted ceilings and abundant natural light highlight the open living and dining areas, featuring a gas log brick fireplace. The versatile layout includes 3 bedrooms, a primary bedroom loft, generous dining room with deck access, and an eat-in kitchen with patio doors to a fenced backyard retreat. Enjoy the stamped concrete patio, fire pit, storage shed, and golf course views! Updates include stainless steel kitchen appliances, front-load stackable washer/dryer, vinyl plank flooring, carpeting, central air, windows, and patio doors. Features include first-floor laundry, a 2-car garage, Ring doorbell and security system. Conveniently located near Lake Windsor Country Club and Windsor Athletic Club, with easy access to Madison, I-39/90/94, and Dane County Regional Airport. Unique style and space make this home a must-see!

6661 Charlie Grimm Rd, Windsor
6835 Parkside Cir, Windsor
$215,000
2 Beds ⋅ 2 Baths ⋅ 2034599 MLS ⋅ ACTIVE Status
Join Parkside Village 55+ Retirement Community. Parkside Village offers Residents the opportunity to Purchase their unit through a Limited Life Estate Grant. Parkside Village offers numerous amenities: a clubhouse, library, fitness center, movie room, billiards room, common grilling station, on-site management and on-site maintenance, Common Area House Keeping. No property taxes! The monthly service fee is $720 and includes on-site management, on-site maintenance, snow removal, lawn care, Property Insurance, Phone, Internet, Cable, Water, Trash, cleaning of common areas, and a social fund for resident activities for an overall carefree, hands-off lifestyle!

6835 Parkside Cir, Windsor
6833 Parkside Cir, Windsor
$205,000
2 Beds ⋅ 2 Baths ⋅ 2032964 MLS ⋅ ACTIVE Status
Join Parkside Village 55+ Retirement Community. Parkside Village offers Residents the opportunity to Purchase their unit through a Limited Life Estate Grant. Parkside Village offers numerous amenities: a clubhouse, library, fitness center, movie room, billiards room, common grilling station, on-site management and on-site maintenance, Common Area House Keeping. No property taxes! The monthly service fee is $720 and includes on-site management, on-site maintenance, snow removal, lawn care, Property Insurance, Phone, Internet, Cable, Water, Trash, cleaning of common areas, and a social fund for resident activities for an overall carefree, hands-off lifestyle!

6833 Parkside Cir, Windsor
6823 Parkside Cir, Windsor
$215,000
2 Beds ⋅ 2 Baths ⋅ 2030119 MLS ⋅ ACTIVE Status
Join Parkside Village 55+ Retirement Community. Parkside Village offers Residents the opportunity to Purchase their unit through a Limited Life Estate Grant. Parkside Village offers numerous amenities: a clubhouse, library, fitness center, movie room, billiards room, common grilling station, on-site management and on-site maintenance, Common Area House Keeping. No property taxes! The monthly service fee is $720 and includes on-site management, on-site maintenance, snow removal, lawn care, Property Insurance, Phone, Internet, Cable, Water, Trash, cleaning of common areas, and a social fund for resident activities for an overall carefree, hands-off lifestyle!

6823 Parkside Cir, Windsor
6683 Charlie Grimm Rd, Windsor
$269,900
2 Beds ⋅ 1 Baths ⋅ 2028893 MLS ⋅ ACTIVE Status
Enjoy carefree living with no condo fees in this beautifully updated half-duplex overlooking picturesque Lake Windsor Country Club and the Yahara River. The bright, open-concept design features luxury flooring, fresh paint, and large windows that fill the home with natural light while showcasing peaceful golf course views. The remodeled kitchen offers granite countertops, subway tile backsplash, stainless steel appliances, abundant cabinetry, and a spacious breakfast bar that opens to the living and dining areas. Two generously sized bedrooms, an updated full bath, and a convenient main-level laundry room provide comfortable everyday living. Step through the patio doors to a private patio where you can relax and enjoy the scenic setting. Attached 1-car garage, mature landscaping, and an ideal Windsor location just minutes from Madison complete this exceptional property.

6683 Charlie Grimm Rd, Windsor
6801 Parkside Cir, Windsor
$215,000
2 Beds ⋅ 2 Baths ⋅ 2025442 MLS ⋅ ACTIVE UNDER CONTRACT Status
Join Parkside Village 55+ Retirement Community. Parkside Village offers Residents the opportunity to Purchase their unit through a Limited Life Estate Grant. Parkside Village offers numerous amenities: a clubhouse, library, fitness center, movie room, billiards room, common grilling station, on-site management and on-site maintenance, Common Area House Keeping. No property taxes! The monthly service fee is $720 and includes on-site management, on-site maintenance, snow removal, lawn care, Property Insurance, Phone, Internet, Cable, Water, Trash, cleaning of common areas, and a social fund for resident activities for an overall carefree, hands-off lifestyle!

6801 Parkside Cir, Windsor
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This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.

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