Windsor Homes under $500,000

Windsor Homes under $500,000

Welcome to Windsor, Wisconsin – a charming community nestled in the heart of Dane County, just a stone's throw away from the vibrant city of Madison. Known for its picturesque landscapes and friendly atmosphere, Windsor offers a perfect blend of small-town charm and modern convenience, making it an ideal place for families, retirees, and everyone in between.

Windsor boasts a rich history and a strong sense of community, with local events and festivals that bring residents together throughout the year. The area is surrounded by beautiful parks and recreational opportunities, including walking trails, lakes, and nature reserves, perfect for outdoor enthusiasts. With its highly-rated schools and family-friendly neighborhoods, Windsor is an excellent choice for those looking to plant roots in a welcoming environment.

For homebuyers seeking affordability without compromising on quality, Windsor presents an enticing selection of homes under $500,000. Whether you're in the market for a cozy starter home, a spacious family residence, or a charming ranch-style property, there’s something for everyone in this delightful community. These homes often feature modern amenities, ample yard space, and access to local parks and community resources.

With its ideal location, strong community spirit, and affordable housing options, Windsor, WI, is not just a place to live—it's a place to thrive. Discover the charm of Windsor today and find your dream home in this beautiful corner of Dane County!

Newest Windsor Homes under $500,000

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
6625 S Oak Ln, Windsor
$499,900
3 Beds ⋅ 3 Baths ⋅ 2034027 MLS ⋅ ACTIVE Status
Welcome to the Lake Windsor Neighborhood. Situated adjacent to the Lake Windsor Country Club Golf Course, this sprawling mid 70s ranch sits on almost an acre of manicured land, tucked in amongst beautiful oaks. The Yahara river flows gently through the back and the views from your deck are second to none. Inside the kitchen has been thoughtfully renovated. Newer stainless steel appliances, cherry cabinetry, quartz counters and a kitchen island. Hardwood floors throughout the main level. Formal dining space, wood burning fireplace in the living room, updated baths, generously sized bedrooms and screened in porch to enjoy the quiet. Walk out lower level features a 3rd bedroom as well as an additional room for your workout space, craft room or library. Massive amount of storage in the lower level, 2 car garage and DeForest Schools. Perfect place to host family for the upcoming holidays.

6625 S Oak Ln, Windsor
7134 S Hill Rd, Windsor
$469,900
3 Beds ⋅ 2 Baths ⋅ 2033052 MLS ⋅ ACTIVE Status
Schedule your showing today for this charming 3-bedroom, 1.5-bath home on a beautiful lot backing up to Oak Springs Park! Enjoy peaceful mornings on your front patio or overlooking the backyard and park from the screened porch or expansive deck. The outdoor space offers endless possibilities, featuring a spacious garden, raspberry bushes, a private firepit area, and mature trees. Inside, this traditional two-story home offers three generously sized bedrooms and a full bath on the second floor. The main level features a comfortable living room, formal dining room, kitchen, half bath and cozy den. The basement includes semi-finished space perfect for a media room, workout area, office, or hobby space along with plenty of additional storage. New windows updated 2023, new furnace 2025, remodeled lower level, and regular mantenance on the utilities. With its desirable park-side setting, spacious yard, and flexible living spaces, this home is ready to welcome its next owner.

7134 S Hill Rd, 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
4347 Windsor Rd, Windsor
$499,000
3 Beds ⋅ 2 Baths ⋅ 2032217 MLS ⋅ ACTIVE Status
This inviting 3-bedroom, 2-bath home offers plenty of space both inside and out! The fully finished basement features a large rec room, perfect for entertaining, relaxing, or creating a second living space. Cozy up by the wood-burning fireplace, or head outside to enjoy the above-ground pool and spacious backyard—a rare find for an in-town property! Conveniently located across from Windsor Elementary, this home combines space, comfort, and a great location.

4347 Windsor Rd, Windsor
4351 Windsor Rd, Windsor
$450,000
4 Beds ⋅ 3 Baths ⋅ 2030670 MLS ⋅ ACTIVE UNDER CONTRACT Status
Charming 4-Bedroom Home with Modern Updates – Sold As-Is Step into this spacious 4-bedroom, 2.5-bath home that blends recent upgrades with room for your personal touch. The remodeled kitchen, bathrooms, and finished basement offer a fresh, modern feel, while major mechanical updates provide peace of mind — new furnace (2024), water heater (2024), roof (2022), and windows (2025). Inside, you’ll find a functional layout perfect for both everyday living and entertaining. The home does need fresh paint, carpet cleaning or replacement, and a few minor fixture updates, making it an ideal opportunity to customize to your style. The seller is offering a $15,000 cosmetic update allowance, subject to the terms of an accepted offer and lender approval. This property is a fantastic find for buyers looking for value and potential.

4351 Windsor Rd, 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
6659 Ramshorn Dr, Windsor
$499,900
3 Beds ⋅ 2 Baths ⋅ 2027528 MLS ⋅ ACTIVE Status
Welcome to Lot 285 in Bear Tree Farms, featuring the newly built Topaz Plan! This 3-bedroom, 2-bath ranch offers over 1,900 sq ft of thoughtfully designed living space just minutes from Madison. Enjoy upscale finishes throughout, including open railings with black iron balusters, oversized 5" base trim, stainless steel appliances, granite countertops, soft-close cabinetry, 42" upper cabinets, a large center island, and beautifully tiled tub and shower surrounds. The open-concept living room features a gas fireplace with a stone surround. The unfinished lower level includes an egress window and bath rough-in, offering excellent potential for future living space. Exceptional quality and value, all for under $500,000! Some photos/plans may be of a similar model and may not depict the exact home. Some photos may be virtually staged or digitally edited.

6659 Ramshorn Dr, Windsor
Start Your Search

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.

How much is your home worth?

Get instant property value now!