Refine Search
Map
Sort by
$600,000
4 Beds ⋅ 2 Baths ⋅ 2031883 MLS ⋅ ACTIVE Status
Tucked in the Cherrywood neighborhood, this beautifully maintained home offers a peaceful setting on over half an acre, backing to green space & with access to a neighborhood path. Inside, the light-filled living room is open to the remodeled kitchen, creating an inviting space. The kitchen features custom cherrywood cabinets, a granite island, tile backsplash, & quartz counters, while the adjacent dining room leads to the deck. The spacious rec room with a wet bar provides even more room to gather, with a walkout to the backyard. Four spacious bedrooms provide plenty of room for everyone, while the remodeled bathrooms add a fresh, updated feel, including heated floors in the upstairs bathroom. Outside, there’s plenty to enjoy, including garden beds & a heated shed with electricity that offers a versatile space for a getaway or greenhouse use. A new 2025 roof adds even more peace of mind, while Middleton schools & a convenient west-side location make this an easy place to call home.

3663 Swoboda Rd, Middleton
$750,000
3 Beds ⋅ 4 Baths ⋅ 2031600 MLS ⋅ ACTIVE Status
This spectacular contemporary home has something for everyone. A gorgeous gourmet kitchen for those who love to cook and entertain. BIG sheltered porch and deck for outdoor entertaining. A huge rec room with a second kitchen area for sports or movie watching. Unparalleled location with nearby walking path where berries and mushrooms can be harvested for dinner. That GARAGE! What!? 974 square feet of pure bliss for the hobbyist who needs some room! All located on a beautiful 1+ acre parcel with more flower plantings from a hobbyist who made it her mission to have flowers blooming in all seasons!

3470 Leflore Ct, Middleton
$825,000
4 Beds ⋅ 3 Baths ⋅ 2029049 MLS ⋅ ACTIVE Status
Tucked in a beautiful wooded setting in Applewood Hills, this distinctive 4-bed, 2.5-bath home blends privacy, architectural character and thoughtful high-end updates. The light-filled main level showcases vaulted ceilings, exposed beams, wood floors and a dramatic floor-to-ceiling stone fireplace with built-in shelving. Expansive windows and patio doors bring the outdoors in and open to a spacious elevated deck overlooking the private, tree-lined yard. The updated kitchen features newer appliances, generous workspace and picturesque views. Major improvements include newer mechanicals, windows, and numerous quality updates throughout, offering comfort and peace of mind. Multiple living and dining spaces provide plenty of room to gather and entertain. Outside, enjoy mature trees, lush landscaping, a large lawn and fenced area creating a peaceful, park-like retreat. A truly unique Town of Middleton home with character, privacy and exceptional indoor-outdoor living!

7116 Applewood Dr, Middleton
$775,000
4 Beds ⋅ 4 Baths ⋅ 2031218 MLS ⋅ 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 Rd, Middleton
$700,000
4 Beds ⋅ 4 Baths ⋅ 2029095 MLS ⋅ ACTIVE UNDER CONTRACT Status
Showings start 7/31 @ 3:30pm. Some homes simply provide shelter. This one offers a place to put down roots. Nestled in the heart of Prairie Home Estates, this beautifully appointed two-story home is surrounded by the kind of neighborhood families dream about—where evening walks become tradition, kids ride bikes to the nearby tennis courts, soccer fields and baseball diamonds, and miles of scenic prairie trails are just steps from your front door. Inside, generous living spaces invite everything from holiday celebrations to cozy nights together, while large windows bring the outdoors in. Outside, the private backyard is framed by mature landscaping, colorful gardens, and a charming strawberry patch that has been lovingly cultivated through the years. Here you'll find more than a beautiful home—you'll find a welcoming community, lifelong friendships, and a place where the moments that matter most naturally unfold.

8437 Ellington Way, Middleton
$599,900
4 Beds ⋅ 3 Baths ⋅ 2028997 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home to this beautifully maintained 4-bedroom, 2.5-bath two-story in the sought-after Hickory Woods neighborhood! Situated on over half an acre, this home offers peaceful countryside views, breathtaking sunsets, and a spacious deck perfect for relaxing or entertaining. Enjoy a park across the street, nearby walking and biking trails, easy access to downtown Middleton and Madison, and award-winning Middleton schools. Inside, you’ll find bright living spaces, a spacious eat-in kitchen, and four bedrooms upstairs, including a private primary suite. The partially finished lower level offers additional living space and plenty of hidden storage. Major updates include a new roof (2018) and windows (2019). Thoughtful updates, scenic views, and an exceptional location make this home a must-see!

4507 Stonewood Dr, Middleton
$1,799,000
5 Beds ⋅ 7 Baths ⋅ 2027557 MLS ⋅ ACTIVE UNDER CONTRACT Status
Custom home w/ classic beauty + timeless elegance, perfectly suited on over 1.4 landscaped acres w/waling trails connecting to green space. Grand in scale + design, this thoughtfully crafted residence offers sweeping views, floor-to-ceiling windows, & open yet refined floor plan. Chef's kitchen offers Wolf appliances, Sub-Zero refrigeration, custom cabinetry, + exceptional workspace. Rich woodwork, crown molding, tray ceilings, nine-foot doors, + three stone gas fireplaces showcase impeccable craftsmanship. Luxurious primary features a spa-inspired bath w/ steam shower, body sprays, soaking tub, + expansive walk-in closet. 4 addtl ensuite bedrooms each include private baths + walk-in closets. Walkout LL w/ a spacious family room, Tuscan-inspired brickwork, wet bar + wine cellar. Amenities include exercise room, sunroom, patios, 4-car garage, central vac, programmable irrigation system + much more! A truly remarkable home offering luxury + exceptional attention to detail.

3952 Caribou Rd, Middleton
$589,000
3 Beds ⋅ 4 Baths ⋅ 2026641 MLS ⋅ 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 Ct, Middleton
$1,499,900
5 Beds ⋅ 5 Baths ⋅ 2026869 MLS ⋅ ACTIVE UNDER CONTRACT Status
Experience luxury living in Middleton’s coveted Summit Pass neighborhood, where breathtaking views, exceptional craftsmanship, and timeless elegance come together. The main level showcases a dramatic two-story great room with floor-to-ceiling windows, a striking fireplace, gourmet kitchen, wet bar, inviting outdoor entertaining space, and an expansive primary suite designed for comfort and privacy. Upstairs offers three spacious bedrooms, a flexible den, and two full baths. The finished lower level is an entertainer’s dream with a generous rec room, full bar, wine cellar, theater room, full bath, and fifth bedroom ideal for overnight guests. A stately home office, private fitness room, abundant storage, and oversized heated three-car garage complete this exceptional home at 4498 Nina Lane.

4498 Nina Ln, Middleton
$1,199,900
5 Beds ⋅ 5 Baths ⋅ 2023426 MLS ⋅ ACTIVE Status
Spectacular pre-inspected Modern Queen Anne-Style Victorian Home custom built by Blue Line Designs on a 2A lot in the Town of Middleton. This beautifully finished home features maple, walnut, and acacia hardwood floors, tile, and LVP. It offers 5 bedrooms & two bonus rooms (one is a bedroom), multiple office areas, and generous living space. The expansive 18ft great room is perfect for entertaining, while the large kitchen boasts an island, double oven, gas cooktop, newer dishwasher, and abundant storage. The dining room includes a 9-ft butler’s pantry counter for additional serving & storage space. Custom wet bar in lower level. Step outside to a backyard oasis: a lighted basketball court, custom granite firepit, Trex rear deck with hot tub connection, raised-bed garden, and a yard for soccer, volleyball, or croquet. A serene koi pond with waterfall attracts wildlife daily. Also: Roof 2018, backup gen, heated 5-car garage, 2 laundry areas, Radon system, TDS Fiber, & dual sumps.

7527 Fallen Oak Dr, Middleton
$2,699,000
6 Beds ⋅ 6 Baths ⋅ 2019981 MLS ⋅ ACTIVE Status
Located in the Town of Middleton with low taxes, on a breathtaking, mature, wooded, and private 1.5-acre lot, this extraordinary custom residence offers the high-end finishes, craftsmanship, quality, artistry, and natural privacy today’s luxury buyers demand. Situated in the desirable Glacier End neighborhood, this one-of-a-kind home showcases real cherry hardwood floors, custom cherry cabinetry, and premium granite throughout. Luxury features include a 4-car garage, 6 bedrooms with en-suite baths, two primary suites, two gourmet kitchens, including a chef’s kitchen with commercial-grade appliances, two laundry rooms, a main-floor office, Pella windows with built-in blinds, central vac, intercom, surround sound, and a Decra Villa Tile roof. The walkout lower level offers a wet bar, steam room, exercise room, theater, fireplace, and access to a lush, tree-lined backyard. Middleton Schools!

3319 Saracen Way, Middleton
$2,750,000
4 Beds ⋅ 5 Baths ⋅ 2014299 MLS ⋅ ACTIVE Status
This is an example of a luxurious home that can be built on this vacant lot. This home will be a completely custom new home in any size you want, built by Michael F. Simon Builders. Expected cost of the home is ~$2,750,000, depending on size and finishes. All photos are renderings, buyer will work with builder to design their dream home! This wooded 1.59 acre lot offers a full side and rear yard exposure walkout. Glacier’s Trail is a captivating new housing development designed to offer residents an idyllic country lifestyle with the conveniences of modern living. Enjoy miles of Middleton’s trails as well as the Ice Age Trail system. Only minutes from Middleton + Verona, this subdivision is ready for homes to start immediately..

Lot 13 Glacier Forest, Middleton

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.