Windsor Homes under $500,000

Windsor Homes under $500,000

Welcome to Windsor, Wisconsin – a hidden gem nestled in the scenic Dane County, just a stone's throw from the vibrant city of Madison. Known for its charming neighborhoods, lush green spaces, and a strong sense of community, Windsor offers the perfect blend of suburban tranquility and urban accessibility. With a population that values both family and nature, this delightful city is ideal for those looking to settle down in a friendly environment.

Windsor is characterized by its picturesque landscapes, featuring beautiful parks, walking trails, and recreational areas that encourage outdoor activities year-round. Residents enjoy a rich tapestry of community events, local farmers' markets, and seasonal festivities that foster a strong community spirit. With top-rated schools and a variety of local amenities, Windsor is an excellent choice for families and professionals alike.

If you're in the market for a new home, Windsor boasts a fantastic selection of properties under $500,000. Whether you're searching for a cozy single-family home, a modern townhome, or a spacious property with room to grow, you'll find a diverse array of options to suit your lifestyle and budget. These homes often feature contemporary designs, ample outdoor space, and convenient access to local amenities, making them an attractive choice for first-time buyers and those looking to downsize.

Discover the charm and warmth of Windsor, WI, where your dream home awaits amidst a welcoming community and beautiful surroundings. Let us guide you on your journey to find the perfect home in this enchanting city!

Newest Windsor Homes under $500,000

6661 Charlie Grimm Road, Windsor
$349,500
3 Beds ⋅ 2 Baths ⋅ 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 Road, Windsor

Listing courtesy of First Weber Inc.

6661 Charlie Grimm Road, Windsor
$349,500
3 Beds ⋅ 2 Baths ⋅ 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 Road, Windsor

Listing courtesy of First Weber Inc.

6835 Parkside Circle, Windsor
$215,000
2 Beds ⋅ 2 Baths ⋅ 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 Circle, Windsor

Listing courtesy of Madison Commercial Real Estate LLC.

4466 Gray Road, Windsor
$299,900
2 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status
Enjoy peaceful nature views with the convenience of condo living in this charming 2-bedroom, 1.5-bath townhouse in Windsor! The open floor plan offers a welcoming space to relax or entertain, with peaceful private deck overlooking wetlands, a tranquil pond, and abundant wildlife. Inside, you?ll find two generously sized bedrooms, granite countertops, hardwood and tile flooring, and convenient main-floor laundry. An attached one-car garage provides added storage, while a finished bonus room off the garage offers flexible space for hobbies, workouts, or a cozy retreat. Close to walking and biking trails, with easy access to Madison and Sun Prairie, this condo pairs a scenic setting with everyday convenience.

4466 Gray Road, Windsor

Listing courtesy of Real Broker LLC.

6539 Cortland Park Drive, Windsor
$489,000
3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Welcome home to easy condo living in Windsor! This spacious 3-bedroom, 2.5-bath condo offers a functional layout with the convenience of a main-floor primary suite and main-floor laundry. The kitchen features granite countertops, stainless steel appliances and plenty of workspace. Cozy up around the gas fireplace or enjoy the large screened porch. An attached 2-car garage provides plenty of room for vehicles and storage. With comfortable spaces, quality finishes and a layout designed for everyday living, this condo is ready to welcome you home!

6539 Cortland Park Drive, Windsor

Listing courtesy of First Weber Inc.

7134 S Hill Road, Windsor
$469,900
3 Beds ⋅ 1.5 Baths ⋅ 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 Road, Windsor

Listing courtesy of Restaino & Associates.

6833 Parkside Circle, Windsor
$215,000
2 Beds ⋅ 2 Baths ⋅ 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 Circle, Windsor

Listing courtesy of Madison Commercial Real Estate LLC.

4347 Windsor Road, Windsor
$499,000
3 Beds ⋅ 1.5 Baths ⋅ 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 Road, Windsor

Listing courtesy of First Weber Inc.

4351 Windsor Road, Windsor
$450,000
4 Beds ⋅ 2.5 Baths ⋅ ACTIVE 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 Road, Windsor

Listing courtesy of Realty of America, LLC.

6823 Parkside Circle, Windsor
$215,000
2 Beds ⋅ 2 Baths ⋅ 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 Circle, Windsor

Listing courtesy of Madison Commercial Real Estate LLC.

6683 Charlie Grimm Road, Windsor
$269,900
2 Beds ⋅ 1 Baths ⋅ 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 Road, Windsor

Listing courtesy of Investment Realty Services LLC.

6659 Ramshorn Drive, Windsor
$499,900
3 Beds ⋅ 2 Baths ⋅ 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 Drive, Windsor

Listing courtesy of Best Realty of Edgerton.

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