Windsor Homes under $300,000

Windsor Homes under $300,000

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 small-town charm and modern conveniences. With its close proximity to Madison, residents enjoy easy access to the vibrant cultural scene, dining, and shopping options, while still being able to retreat to the tranquility of suburban living.

Windsor is a family-friendly community, boasting excellent schools, beautiful parks, and numerous recreational activities. Whether you're exploring the scenic trails, enjoying a picnic at one of the local parks, or participating in community events, there’s always something to do in this welcoming town.

For those seeking affordable housing options, Windsor has an array of homes available for under $300,000. These properties are ideal for first-time homebuyers, young families, or anyone looking to invest in a growing community. You’ll find charming single-family homes, cozy townhouses, and well-maintained properties that offer great value without compromising on quality.

As the real estate market continues to thrive, now is the perfect time to explore your options in Windsor. With its affordable housing and strong sense of community, it’s no wonder that so many people are choosing to call this delightful town home. Whether you’re looking for a place to plant your roots or a smart investment opportunity, Windsor is a hidden gem waiting to be discovered. Come see for yourself why so many are falling in love with this vibrant community!

Newest Windsor Homes under $300,000

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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