Cottage Grove Homes under $500,000

Welcome to Cottage Grove, Wisconsin – a charming community nestled in the heart of Dane County! With its picturesque landscapes and friendly atmosphere, Cottage Grove is the perfect place for families, young professionals, and retirees alike. Just a stone's throw away from the bustling city of Madison, residents enjoy the best of both worlds: a serene suburban lifestyle paired with easy access to urban amenities.

Cottage Grove boasts a rich history, vibrant local culture, and a strong sense of community. Enjoy the numerous parks, walking trails, and recreational opportunities that make this city a haven for outdoor enthusiasts. From the beautiful Glacial Drumlin State Trail to the serene parks like Bakken Park, there’s no shortage of space to unwind and enjoy nature.

For those looking to settle down in Cottage Grove, the real estate market offers an impressive array of homes priced under $500,000. Whether you're searching for a cozy single-family home, a contemporary townhome, or a charming bungalow, you’ll find options that suit every taste and budget. With its affordable housing market, Cottage Grove is an attractive choice for first-time homebuyers and families looking to grow.

In addition to its affordable homes, Cottage Grove is known for its excellent schools and community programs, making it an ideal location for families. With a variety of local shops, restaurants, and community events, Cottage Grove is a place where neighbors become friends and lifelong memories are made. Explore the opportunity to call this delightful city home, and discover the charm of Cottage Grove, Wisconsin!

Newest Cottage Grove Homes under $500,000

$419,900

3 Beds ⋅ 4 Baths ⋅ 2033575 MLS ⋅ ACTIVE Status

Welcome to 510 Nightingale Ln in Cottage Grove! This spacious 3-bedroom home offers 2 full baths, 2 half baths and 2,208 sq ft of finished living space in a desirable zero lot line setting on a corner lot. The bright functional layout features a gas fireplace, all appliances and convenient second-floor laundry with a large-capacity washer and dryer located near the bedrooms. The vaulted primary suite includes double closets and a private bath with jetted tub. The finished walkout lower level adds a comfortable family room plus flexible space for relaxing, entertaining, a home office or workout area. Outside, enjoy exceptional yard space, a composite deck added in 2021, refinished patio and wonderful views of the town fireworks. Major updates include a new roof in May 2026. An attached 2-car garage provides additional storage and everyday convenience. A great combination of space, updates, outdoor living and location, ready for its next owner! Close to parks, trails and local amenities.

510 Nightingale Ln, Cottage Grove

$330,000

3 Beds ⋅ 1 Baths ⋅ 2032817 MLS ⋅ ACTIVE Status

Showings Start 9/25. 1920s character on a rare double lot in the heart of Cottage Grove! This 3-bed home offers nearly 1,800 sq. ft. w/ original maple wood floors, a large dining room w/ natural light, main-floor den/office with privacy doors & plenty of original charm. At the heart of the home, the kitchen walks out to a large fenced-in yard with a massive concrete patio & plenty of space to entertain, garden, play or simply enjoy the extra room that comes with the lot. Grab your warm beverage & head out to the classic front porch to enjoy the charm of the neighborhood. The location is hard to beat: a short stroll to Main St. for coffee & dining, Fireman’s Park and the Glacial Drumlin Trail, with Phoebe Bakken Memorial Park nearby, too. Take advantage of community events & everything Cottage Grove has to offer. Updates include fridge (2021), front fence (2018), light fixtures, front door & 9 windows. UHP Ultimate Home Warranty Plan offered for peace of mind.

118 Clark St, Cottage Grove

$475,900

3 Beds ⋅ 3 Baths ⋅ 2032636 MLS ⋅ ACTIVE Status

Brand new 3 bedroom 3 bath ranch style zero-lot-line half duplex in popular Westlawn Estates. Open concept floor plan has vaulted great room with electric fireplace, quartz countertops throughout the home, LVP flooring in main living areas, and LVT flooring in all bathrooms. Split bedroom design. Large primary bedroom suite has private full bath with dual vanity and large walk-in closet. Finished exposed lower level rec/media room, bedroom, full bath and storage space. Two car attached garage with laundry/mud room. Walking distance to Taylor Prairie and Granite Ridge Elementary School and close to Glacial Drumlin Middle School.

1127 Parkview St, Cottage Grove

$405,000

3 Beds ⋅ 2 Baths ⋅ 2032322 MLS ⋅ ACTIVE UNDER CONTRACT Status

Welcome home to this move-in ready 3-bedroom ranch in desirable Cottage Grove! Offering the perfect combination of comfort, convenience, and location, this home is ready for you to settle in and make it your own. Recent updates including a new roof and new windows provide peace of mind and a fresh start for its next owner. The single-level ranch layout offers easy, everyday living with plenty of potential to make the space uniquely yours. Ideally located close to schools, shopping, dining, parks, and everyday amenities. Commuters will love the easy access to the interstate and Beltline, making trips to Madison and surrounding communities a breeze. Whether you're a first-time buyer, downsizing, or simply looking for a home in a fantastic location, this Cottage Grove gem checks all the boxes. Move-in ready, ideally located, and waiting for its next chapter!

436 Connie St, Cottage Grove

$455,000

4 Beds ⋅ 3 Baths ⋅ 2031436 MLS ⋅ ACTIVE Status

Showings start at Open House Sunday 9/27/26 from 10-12. Discover this well-cared-for, single-owner home offering 4 bedrooms, 2.5 baths, and over 2,400 sq. ft of finished living space. The main level features an open layout with a spacious eat-in kitchen, updated countertops, sink, and appliances, large pantry, flowing seamlessly into a large family room with a cozy fireplace and large windows for lots of natural light. A versatile main level bonus room provides the perfect space for a home office, playroom, or formal sitting area. Upstairs, the primary suite includes a private bath and walk-in closet & 3 more bedrooms. The lower level offers a second family room along with an abundant unfinished storage area. Recent updates include newer carpet and luxury vinyl tile, a roof approximately 10 years old, a furnace and air conditioner replaced in 2021, and fresh interior paint.

312 Tanglewood Ct, Cottage Grove

$467,000

4 Beds ⋅ 2 Baths ⋅ 2030280 MLS ⋅ ACTIVE UNDER CONTRACT Status

Welcome to this charming 4-bedrm, 2 bath home in Cottage Grove, situated on a beautifully maintained 0.50-acre lot. The home offers comfortable living spaces, a 2-car garage, and a wood-burning fireplace that provides a warm & inviting focal point for relaxing or gathering. Step outside and enjoy multiple outdoor living spaces, including a deck just off the main-level patio door & a lower-level patio accessible through a patio door, creating additional opportunities to enjoy the outdoors. The spacious yard is beautifully landscaped with established perennial gardens, offering seasonal color & natural beauty throughout the year. A book of seasonal photos will be available inside the home, allowing you to see how the landscaping & perennial gardens transform throughout the seasons. With its generous half-acre lot, multiple outdoor spaces, established landscaping, and inviting interior features, this Cottage Grove home offers plenty to enjoy.

4346 Damascus Trl, Cottage Grove

$469,000

5 Beds ⋅ 4 Baths ⋅ 2030892 MLS ⋅ ACTIVE Status

It's time to move into this spectacular, established neighborhood and create the home you've been dreaming of! Butterflies and hummingbirds abound in the lovely landscape. The fully redone lower level features 2 bedrooms, kitchen area, built in surround sound speakers for movie and gaming fun. Main level has a cozy fireplace room off the kitchen. Lovely kitchen and dining area that looks out over the back green space. Garage has an EV charging station. No condo fees, no hidden costs, no shared walls. Its been a well loved home and only needs you to put your paint and flooring ideas in there and your next chapter will be ready to go!

200 Dentaria Dr, Cottage Grove

$315,000

3 Beds ⋅ 2 Baths ⋅ 2029547 MLS ⋅ ACTIVE Status

Come visit this exceptional private-entry end-unit condo! Completely remodeled in 2019 w/premium finishes & quality craftsmanship throughout, this move-in-ready home stands above the rest. Hickory hardwood floors, custom oak cabinetry & trim, solid 6 panel doors, quartz countertops, & all-new appliances & mechanicals create a timeless, upscale feel. The chef-inspired kitchen offers abundant storage, expansive prep space, a breakfast bar, and room for a large dining table—perfect for entertaining. The spacious dining area opens to a private deck overlooking a peaceful setting. Upstairs are 3 bedrooms & a beautifully updated full bath. The lower level features a lg laundry room w/custom storage, an oversized storage area, & access to the attached oversized 1 car garage, plus 2 designated exterior parking spaces. Tucked away on a quiet dead-end street with quick access to Hwy N, I-94, shopping, & restaurants, this is low-maintenance living w/out compromising on quality.

909 N Clover Ln Unit D, Cottage Grove

1501 N Windsor Ave Unit 305, Cottage Grove

$279,900

2 Beds ⋅ 2 Baths ⋅ 2030029 MLS ⋅ ACTIVE UNDER CONTRACT Status

Enjoy top-floor, corner-unit living, beautiful pond views and thoughtful upgrades in this 2-bedroom, 2-bath plus den Cottage Grove condo! Seasonally occupied since new, with less than 2 years total occupancy and never rented. Bright, open-concept living features custom upgrades including quartz countertops, tile backsplash, under-cabinet lighting, kitchen faucet and updated fixtures. The spacious kitchen offers a large island, stainless appliances and walk-in pantry, opening to the dining and sun-filled living areas. Oversized patio doors lead to a composite balcony with glass railing, perfect for relaxing while enjoying peaceful pond and nature views. The primary suite features a large walk-in closet with pocket door and private bath with glass-door shower. In-unit laundry, energy-efficient HVAC system, elevator, heated underground parking, private storage area and off-street parking. Easy interstate access and walkable to local restaurants!

1501 N Windsor Ave Unit 305, Cottage Grove

$475,000

4 Beds ⋅ 3 Baths ⋅ 2029997 MLS ⋅ ACTIVE Status

Tucked away at the end of a quiet cul-de-sac in the Town of Cottage Grove, this sprawling two-story home offers the perfect blend of space, comfort, and convenience. Set on a generous lot, the expansive backyard features a play area and plenty of room to create the garden you've always wanted. Inside, the spacious kitchen serves as the heart of the home, flowing seamlessly into the dining area, family and living room, and walkout to inviting screened porch & deck—ideal for everyday living and effortless entertaining. All four generously sized bedrooms are located upstairs, including a private primary suite with its own bath. The finished lower level provides flexible space for a rec room, home theater, office, or hobbies, plus abundant storage. Recent updates include a brand-new roof and replacement siding in 2026, offering added peace of mind. Conveniently located within walking distance to schools, parks, and local amenities. Don't miss out!

4552 Falcon Ct, Cottage Grove

$444,900

3 Beds ⋅ 3 Baths ⋅ 2028690 MLS ⋅ ACTIVE Status

SPACIOUS MAIN FLOOR LIVING! WALK TO THE PARK, SCHOOL & MORE! Set on a spacious corner lot, this 2,300+ sq ft, 3 bedroom, 3 bath home features an open layout, vaulted ceilings, two fireplaces, and a finished lower level. Walk to Northlawn Park and Taylor Prairie Elementary in the Monona Grove School District, with quick access to Hwy 12/18 and Madison. The main level offers vaulted ceilings and a wood burning fireplace, updated large back deck, and laundry. The master bedroom includes a walk-in closet and en-suite bath, while two additional bedrooms are located at the opposite end for added privacy. Downstairs, the finished lower level adds a spacious multi-purpose room with a gas fireplace, a full bathroom, and plenty of flexible space for relaxing, entertaining, working from home, or hosting guests. A large utility and storage area provides additional room for seasonal items and household needs. Updates- furnace and gutters: 2023; stove and refrigerator: 2024; egress window: 2025

752 Westlawn Dr, Cottage Grove

$399,000

2 Beds ⋅ 1 Baths ⋅ 2028627 MLS ⋅ ACTIVE Status

Rare opportunities like this don't come along often! Nestled on an incredible 1.6-acre lot in the heart of Cottage Grove, this charming 2-bedroom, 1-bath ranch offers a property that's nearly impossible to find within village limits. Whether you've dreamed of creating your own backyard oasis, adding gardens, hosting gatherings, or simply enjoying wide-open green space, this expansive lot provides endless room to make it your own. Inside, you'll find a cozy, inviting home, while outside you'll enjoy the privacy and freedom that only a property of this size can offer. All this, just minutes from parks, shopping, restaurants, and with convenient access to major highways for an easy commute. Experience the perfect balance of in-town convenience and the spacious feel of country living—properties like this are truly one of a kind!

237 N Main St, Cottage Grove

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