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$750,000
4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Parade-quality custom construction that has been meticulously maintained & still shows like new! Located in the highly desirable Community of Bishops Bay, this impressive home offers a thoughtful floor plan, high-quality finishes & exceptional condition throughout. The main level features beautiful wood floors, a spacious kitchen with custom cabinetry, granite countertops, large island & hidden walk-in pantry, all opening to a bright hearth room with gas fireplace. A dedicated office, mudroom & first-floor laundry add everyday functionality. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet & private bath with tiled shower and dual vanity, plus three additional bedrooms. The finished lower level adds outstanding entertaining space with a family room, wet bar, theater & exercise room. Outside, enjoy the covered front porch, Trex deck, patio and established landscaping. City of Middleton with Waunakee schools - don't miss this quality, well-cared for home.

4420 Back Nine Drive, Middleton

Listing courtesy of Stark Company, REALTORS.

$480,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Move right into this beautiful 3 bedroom home conveniently located on Middleton's NE side. Home has had numerous updates over the last 7 years including furnace/AC, siding, windows, roof and remodeled kitchen. Spacious living room with gas fireplace conversion and LVP flooring. Enjoy the weather, but not the bugs in your screened-in porch. Fenced backyard includes a small brick patio area and a storage shed. Centrally located with easy access to East Madison, Waunakee, plenty of shopping and dining, Lake Mendota and Pheasant Branch Conservancy.

5713 Highland Way, Middleton

Listing courtesy of Realty Executives Capital City.

$775,000
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Welcome to this classic two-story Colonial in the desirable Cherrywood neighborhood! Nestled on a beautiful wooded lot, you'll enjoy peaceful country living with the convenience of nearby shopping, dining, and amenities. Take quiet walks, relax on the deck, and enjoy the deer, birds, and other wildlife right in your own backyard. The main level offers a spacious family room with a fireplace, formal living room with a second fireplace, formal dining room, and a private study, perfect for working from home. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite with a private sitting area and large ensuite bath. The walk-out lower level provides additional living space and endless possibilities for future finishing or recreation. Home is being sold AS-IS

3534 Swoboda Road, Middleton

Listing courtesy of Berkshire Hathaway HomeServices True Realty.

$1,400,000
5 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
Welcome to this gorgeous home set on 1.5 acres in the highly sought-after Middleton School District. Offering the perfect blend of space, privacy, and thoughtful updates, this property has been meticulously improved for comfortable, worry-free living through the whole home. Main level primary en suite. Recent upgrades include new garage doors, an upgraded roof, new 6" gutters, newly insulated garage, updated garage flooring, along with other improvements you will have to see. The lower-level workroom is an incredible bonus, an ideal space for tuning skis, working on bikes, tackling projects, or enjoying your favorite hobby with access to the back yard. Outside, the expansive yard offers plenty of room to relax, entertain, garden, and enjoy the peaceful surroundings. A rare opportunity to enjoy country-like space while remaining conveniently close to Verona, Middleton, Madison, shopping, dining, and everyday amenities. Beautifully maintained, extensively updated, and ready to enjoy!

7744 Pamela Circle, Middleton

Listing courtesy of Sprinkman Real Estate.

$800,000
5 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Welcome home to this immaculate and beautifully maintained 5-bedroom home in the desirable Northlake neighborhood, offering an impressive combination of space, style, and privacy. With no neighbors directly behind, this home provides a peaceful setting and a backyard designed for relaxing and entertaining.The main floor offers an exceptional amount of living space with a formal living room, formal dining room, family room, powder room, laundry room, and a bright sunroom filled with natural light. Whether you?re hosting a holiday dinner, enjoying a quiet morning in the sunroom, or relaxing at the end of the day, there?s a space for every occasion.The finished lower level adds even more usable living space and is ready for fun! Enjoy a family room, workout area, and an additional fifth bedroom featuring a convenient Murphy bed?perfect for overnight guests while still allowing the room to serve multiple purposes. Ultimate home warranty included.

5502 Upland Trail, Middleton

Listing courtesy of First Weber Inc.

$1,450,000
6 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Some homes simply check the boxes. Others become the place where memories are made. Nestled in the Back Nine of the Community of Bishops Bay, this custom-built Acker home was designed for gathering, celebrating, & enjoying the moments that matter most. Morning coffee on the screened porch, holidays around the impressive stone fireplace, movie nights in the rec room, & summer evenings around the fire pit in your private yard all become part of everyday life. Beautiful architectural details, soaring ceilings, custom millwork, an impressive Chef's kitchen & thoughtfully designed living spaces create warmth & elegance throughout. Set within one of Dane County's most sought-after communities with a neighborhood pool, clubhouse, fitness enter, parks, trails, & top-rated Waunakee Schools, this is a home you'll never want to leave. Adjacent to renowned private Bishops Bay Golf & Country Club. See attached feature sheet for all upgrades.

4830 Breakers Rock Road, Middleton

Listing courtesy of Pinnacle Real Estate Group LLC.

$1,590,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status
Exceptional custom home offering luxurious finishes & thoughtful design throughout. The stunning great room features a floor-to-ceiling fireplace flanked by custom built-in shelving. A chef's kitchen boasts a large center island, 6-burner range w/ griddle, expansive walk-in pantry, & seamless flow into the dinette, complete w/ a wine bar, beverage refrigerator drawers, & wine cooler. Enjoy year-round entertaining on the screened porch w/ a fireplace & adjoining maintenance-free deck. The main level includes a private office w/ French doors & built-in cabinetry, plus a second office or flex room. Upstairs, the spacious primary suite offers a double vanity, soaking tub, & tiled shower, along w/ convenient second-floor laundry. Two bedrooms share a Jack-and-Jill bath, the third bedroom features private baths. The finished walkout lower level includes family room, a wet bar, bedroom, full bath, & access to the backyard. Completing the home is an oversized 3-car. Overlooks Pioneer Pointe.

7616 Tumbledown Trail, Middleton

Listing courtesy of Collective Real Estate Group.

$589,000
3 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Enjoy peaceful living on a quiet cul-de-sac set on nearly an acre! Charming curb appeal and a welcoming covered front porch create a warm first impression. Inside is tons of space for both everyday living and entertaining. The formal dining room opens to a large screened porch, providing a perfect spot to relax or dine. The kitchen offers abundant cabinet storage and generous counter space. A 2nd living room with a fireplace opens onto a deck overlooking the expansive fenced yard. Upstairs are 3 beds and 2 full baths, including a primary with a private bath. Brand-new carpet on the stairs and upper level adds a fresh touch. The walk-out lower level offers even more space with a large rec room, a 3rd full bath, and 2 versatile flex rooms ideal for an office, gym, hobbies, or guests. Conveniently located just minutes from Middleton, Epic, shopping, dining, and parks. It also offers easy access to the Ice Age Trail for hiking and year-round outdoor recreation. See the 3D tour!

7824 Caribou Court, Middleton

Listing courtesy of Spencer Real Estate Group.

$1,450,000
5 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
Nestled in the prestigious Blackhawk neighborhood and located in the highly sought-after Middleton School District, this former Parade of Homes residence showcases timeless elegance, exceptional craftsmanship, and high-end finishes throughout. A dramatic two-story foyer with a handcrafted curved staircase welcomes you into a light-filled interior featuring soaring cathedral ceilings, rich hardwood floors, arched doorways, and five fireplaces. The gourmet kitchen offers premium appliances, expansive prep space, a large island, and butler?s pantry leading to the formal dining room. Each bedroom features its own ensuite bath, while the main-level office offers flexibility as an additional bedroom. Floor-to-ceiling windows highlight the stunning living room, and the luxurious primary suite includes a private fireplace and spa-like bath. The walkout lower level features a theater room, recreation space, and fifth bedroom.

9715 Red Sky Drive, Middleton

Listing courtesy of Bunbury & Assoc, REALTORS.

Copyright 2026 WIREX Multiple Listing Service. 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 prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.

Copyright 2026 WIREX Multiple Listing Service. 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 prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.