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1501 N Windsor Ave Unit 201, Cottage Grove
$285,000
3 Beds ⋅ 2 Baths ⋅ 2034181 MLS ⋅ ACTIVE Status
The Setting of this condo sets it apart from others. Spacious 1092 Sq ft, end unit garden condo. This Condo features 3 bedrooms and 2 full baths. Enjoy an open and inviting layout with so much natural light and the privacy of an end-unit location. Relax on the patio overlooking peaceful green space, with an abundance of wildlife. Perfectly situated for morning coffee or evening sunsets. This Condo Features all of the high quality details you'd expect in newer construction. Quartz countertops, SS appliances, spacious kitchen w/walk-in pantry, breakfast bar, open floor plan, LVP flooring through out. Spacious Primary Bedroom with, private bath, double vanity, Quartz tops, and Large walk in closet. Laundry in unit. High-efficiency Mitsubishi HVAC. Convenient location, near I-94 with quick access to Madison. Keyless entry, 1 heated, underground parking space & storage unit all included.

1501 N Windsor Ave Unit 201, Cottage Grove

719 Weald Bridge Rd, Cottage Grove
$580,000
4 Beds ⋅ 3 Baths ⋅ 2033907 MLS ⋅ ACTIVE Status
Welcome home to this wonderful ranch in highly desirable Southlawn Estates! The open concept main level features gleaming solid hickory hardwood floors and vaulted ceilings throughout the living, kitchen, family and dining rooms. The spacious eat-in kitchen offers granite counters and a pantry. Relax in the four season sunroom with Mitsubishi mini split heat/AC, opening to a paved patio. The large primary suite boasts a walk-in closet and jetted tub. 4 beds, 3 full baths, natural gas fireplace and central vac. The lower level offers 8+ ft ceilings, wetbar, a theater room and in-wall speakers, a flex/exercise room remodeled in 2026, and additional space with great potential. Oversized 3 car garage with extra storage. Keypad entry on a 0.31 acre level lot with invisible pet fence. Recent updates include 2025 architectural roof and gutters, 2024 Bosch fridge, 2023 water softener, 2026 hvac/dryer duct cleaning and 2023 LG washer/dryer, keyless entry, plus no HOA. Nearby parks & Top Schools

719 Weald Bridge Rd, Cottage Grove

400 Michelle Ln Unit 65, Cottage Grove
$635,000
5 Beds ⋅ 3 Baths ⋅ 2033897 MLS ⋅ ACTIVE Status
Move-In Ready!! Welcome to The Reagan, a meticulously designed new home that perfectly balances elegance and practicality. This spacious 2,166 sq ft two-story residence features 5 bedrooms, 2.5 bathrooms, and a 3-car garage, making it an ideal choice for those seeking both comfort and style. As you enter the Reagan, you'll be greeted by a grand foyer that leads to an open-concept living area. The expansive kitchen, complete with modern appliances, ample cabinetry, and a large island, seamlessly flows into the dining and family rooms, creating a perfect space for entertaining and everyday living. Main floor office/bedroom & 4 bedrooms on upper level Virtual tour shown are of a similar completed model with the same plan. Seller is a licensed real estate company.

400 Michelle Ln Unit 65, Cottage Grove

1942 County Road Bb, Cottage Grove
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 2033730 MLS ⋅ ACTIVE Status
A rare opportunity to own an extraordinary 25+ acre country estate where privacy, history & natural beauty come together. Ideal for equestrian enthusiasts, hobby farmers or those seeking a peaceful country retreat. Picturesque grounds offer open fields, a pond, riding/walking trails, plus a charming 1860s log cabin. Equestrian amenities include paddock w/shelters, outdoor driving arena & impressive 60'x40' historic barn w/3 stalls, beautiful upper barn for storage or more and Approx.2 acres permanent pasture & 9 acres established grass hay. Classic Home boasts, hardwood floors that lead to a beautifully remodeled kitchen. Home features kitchen w/custom Cherrywood cabinetry handcrafted from trees harvested on the property. A substantial addition provides a spacious great room, 2 bedrooms, additional baths, laundry, basement & garage. Greenhouse, gazebo & sheds complete this remarkable property. Adistinctive blend of craftsmanship, history, recreation & country living.

1942 County Road Bb, Cottage Grove

510 Nightingale Ln, Cottage Grove
$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

4550 Sundance Ct, Cottage Grove
$579,900
3 Beds ⋅ 3 Baths ⋅ 2033293 MLS ⋅ ACTIVE Status
Space, privacy and versatility come together at 4550 Sundance Ct! This spacious 3-bedroom, 2.5-bath ranch offers over 3,200 finished sq. ft. on a beautiful 0.67-acre lot tucked into a quiet cul-de-sac. Inside, hardwood floors flow through an open, inviting layout featuring a well-appointed kitchen with granite counters, stainless appliances, and a large breakfast bar. Multiple living spaces include a sun-filled great room surrounded by windows, warm wood walls, and one of the home's two fireplaces. Step outside to the large, private yard and new maintenance-free deck, perfect for entertaining or simply enjoying the peaceful setting. The finished lower level adds a large rec room plus two oversized workshops, offering incredible space for hobbies, projects, and storage. Main-level laundry, 2-car attached garage, and plenty of room to spread out make this one worth seeing!

4550 Sundance Ct, Cottage Grove

213 Yarrow Hill Dr, Cottage Grove
$549,900
3 Beds ⋅ 4 Baths ⋅ 2033267 MLS ⋅ ACTIVE Status
Welcome home to 213 Yarrow Hill, where thoughtful updates, generous living space + a private wooded backdrop come together on over a half-acre in the heart of Cottage Grove. The comfortable, functional layout flows effortlessly from one space to the next, offering versatility for everyday living + entertaining. The kitchen features granite countertops, a large center island, abundant cabinetry + storage and all-new stainless steel appliances (2026). A light-filled sunroom opens to a large stamped concrete patio overlooking the peaceful wooded setting. The finished lower level adds a spacious rec room, versatile flex room + full bath. The 3-car garage provides plenty of additional space. Major updates include a new roof (2025), furnace + A/C (2024) and LeafGuard gutters. Just steps from the Glacial Drumlin State Trail + neighborhood park, with The Oaks Golf Course nearby. Move-in ready with the big-ticket improvements already complete!

213 Yarrow Hill Dr, Cottage Grove

118 Clark St, 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

824 N Clover Ln, Cottage Grove
$650,000
2032582 MLS ⋅ ACTIVE Status
BRAND NEW roof, siding, & garage doors. Seize the chance to own & live in a side-by-side duplex in Cottage Grove, WI, while earning rental income! Both units are mirrored images and have similar updates in last 10 years. LVT flooring throughout, new tile in bathrooms, quartz countertops in kitchen, new furnaces, newer kitchen appliances & much more (see docs for full list of updates); Both sides currently rented: Unit A, 2,050, until 4/30/27 & Unit B, $1,875 until 2/28/27. Located in top-rated school district, merely two blocks from K-2 school, this duplex promises both comfort & convenience. 1 pet allowed, and both units provide a large, private backyard and deck. Some other features to highlight open concept living, primary bedroom en-suite, & 2 car garage. Not interested in owner-occupancy? Hold it as an investment property. Long term tenant on left side and currently leased under market value!

824 N Clover Ln, Cottage Grove

209-215 School Rd, Cottage Grove
$899,900
2032541 MLS ⋅ ACTIVE Status
Fantastic 4 Unit Investment Opportunity in Cottage Grove! Well maintained and located in the Monona Grove School District, this property offers spacious 2 bedroom, 1 bath units with the features today’s renters want! Each unit includes in unit laundry, a gas fireplace, generous living space, and a private garage. Strong rental appeal combined with room to increase rents, making this an excellent opportunity to improve cash flow and long-term investment value. Convenient Cottage Grove location and a property that has been well cared for make this a standout addition to any portfolio. Another 4 unit property immediately next door is also available for sale—an excellent opportunity to expand your portfolio with 8 total units!

209-215 School Rd, Cottage Grove

201-207 School Rd, Cottage Grove
$899,900
2032505 MLS ⋅ ACTIVE Status
Fantastic 4 Unit Investment Opportunity in Cottage Grove! Well maintained and located in the Monona Grove School District, this property offers spacious 2 bedroom, 1 bath units with the features today’s renters want! Each unit includes in unit laundry, a gas fireplace, generous living space, and a private garage. Strong rental appeal combined with room to increase rents, making this an excellent opportunity to improve cash flow and long-term investment value. Convenient Cottage Grove location and a property that has been well cared for make this a standout addition to any portfolio. Another 4 unit property immediately next door is also available for sale—an excellent opportunity to expand your portfolio with 8 total units!

201-207 School Rd, Cottage Grove

436 Connie 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

308 Southing Grange, Cottage Grove
$749,900
5 Beds ⋅ 3 Baths ⋅ 2031817 MLS ⋅ ACTIVE Status
Exceptional 5 bedroom plus office, 3 bath custom ranch in Cottage Grove! Offering 4,717 sq. ft. of finished living space on a private .80 acre lot with large yard and perennial garden backing onto creek. The main level features a formal living room, a family room, primary bedroom and two additional bedrooms. The lower level boasts a 420 sq. ft. dance floor, rec room, two more bedrooms and plenty of space for entertainment, guests, hobbies, or multi-generational living. This custom home is built with ICF construction (insulated concrete forms), steel stud framing and fiber cement siding offering exceptional strength, energy efficiency and quiet comfort. The spacious floor plan includes multiple gathering areas, formal and casual dining spaces, a beautiful kitchen overlooking a lovely natural setting and a 3-car garage with an additional 300 sq. ft. of attic storage above!

308 Southing Grange, Cottage Grove

312 Tanglewood Ct, Cottage Grove
$449,000
4 Beds ⋅ 3 Baths ⋅ 2031436 MLS ⋅ ACTIVE Status
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

390 Progress, Cottage Grove
$985,000
2031425 MLS ⋅ ACTIVE Status
Dippin' Dog Daycare, a thriving 5-star rated dog daycare in the Madison WI MSA, offered with the real estate included. This owner-operated facility features a 60'x40' indoor play area, indoor swim pool/deck, wash station, and welcoming office — steps from surrounding neighborhoods and next to a children's daycare, driving convenient dual drop-off traffic. Sale includes the business, equipment, inventory, proprietary systems, customer database (200+ active app members), website, and booking software. A loyal local customer base and a new subdivision under construction nearby support strong upside. Untapped potential in overnight boarding, grooming, training, and retail — services the current owner-operator hasn't had bandwidth to pursue. A rare chance to acquire a gem of an opportunity in the thriving pet-care business with the real estate in a growing Madison-area community. Check's all the boxes

390 Progress, Cottage Grove

4346 Damascus Trl, 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

305 Michelle Ln, Cottage Grove
$619,507
5 Beds ⋅ 3 Baths ⋅ 2031147 MLS ⋅ ACTIVE UNDER CONTRACT Status
New construction underway with estimated completion in December 26. Welcome to The Reagan, a meticulously designed new home that perfectly balances elegance and practicality. This spacious 2,161 sq ft two-story residence features 5 bedrooms, 2.5 bathrooms, and a 3-car garage, making it an ideal choice for those seeking both comfort and style. As you enter the Reagan, you'll be greeted by a grand foyer that leads to an open-concept living area. The expansive kitchen offers modern appliances, custom maple cabinetry, quartz countertops and a large island. The basement includes framed walls for future bedroom, full bathroom, and large rec room. Basement is also roughed in for full bathroom. Photos are of a similar completed model. Seller is a licensed real estate company.

305 Michelle Ln, Cottage Grove

909 N Clover Ln Unit D, Cottage Grove
$299,000
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

4552 Falcon Ct, 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

3673 Graham Paige Rd, Cottage Grove
$724,900
5 Beds ⋅ 4 Baths ⋅ 2029186 MLS ⋅ ACTIVE Status
Discover country living without sacrificing convenience! Set on over an acre, this custom-built 5-bed, 3.5 bath home offers generous living space, an expansive yard, and plenty of room to enjoy the outdoors. Whether you're relaxing on the patio beneath the pergola or in the hot tub in the screened porch, or practicing your putting on the private green, there's something for everyone to enjoy. Inside, the open main level boasts a large kitchen w/island, great room, formal dining room, den & 1/2 bath. Upstairs has 4 bedrooms, incl. the spacious primary suite w/updated bath & w/in closet, plus a full bath and laundry. The finished LL features a rec area w/impressive wet bar, pool table, 5th bedroom, & full bath. Brand new roof and garage doors, newer HVAC, and SS kitchen appliances. Plus a 3-car garage! Located in the desirable Monona Grove School District w/easy access to the Beltline, I39 & I94, and Madison, this property offers the perfect blend of privacy, space, and accessibility.

3673 Graham Paige Rd, Cottage Grove

752 Westlawn Dr, 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

237 N Main St, 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

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.