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$775,000
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Perched atop one of the highest points in the subdivision, at the end of a quiet cul-de-sac, this exceptional home offers a rare blend of privacy, luxury, and natural beauty. Set on over half an acre, this home borders an incredible network of conservancy land, parks, and walking trails. Every season paints a different view. Inside, you'll find over 3,500 sq. ft. with soaring ceilings, expansive windows that bring the outdoors in, multiple living spaces, a dedicated office, and a stunning cedar four-season sunroom. The spacious primary suite, finished lower level with Brazilian teak hardwood floors and surround sound, composite deck, and numerous major updates?including furnace, A/C, and new carpet throughout complete this exceptional home in the highly sought-after Middleton School District

7473 Meadowrue Circle, Middleton

Listing courtesy of First Weber Inc.

$899,900
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Welcome to this fabulous Middleton Hills home. Classic layout offers main floor living with gleaming wood floors throughout, 3 BRs up, and a 4th in the L.L. The chef will love the large, open kitchen with hickory cabinets, adjacent to the living room w/fireplace and built-ins, dining area and office with wall of built in cabinetry & desk. Formal dining could also act as den or office. Oversize 3-car garage w. built in storage and zero steps into rear foyer, adjacent to large laundry room and pantry. Primary BR suite and 2 additional BRs upstairs. 4th BR, Family Room with FP, and an office/craft room in LL. Large front porch and a back deck for great outdoor living! Home is like new. Everything top-to-bottom, inside and out has been refreshed. New roof; exterior and interior paint; refinished wood floors; all new carpeting; New range/oven & dishwasher. Simply perfect! Includes ULTIMATE UHP Home Warranty.

6713 Gaylord Nelson Road, Middleton

Listing courtesy of Collective Real Estate Group.

$750,000
3 Beds ⋅ 2.5 Baths ⋅ 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 Court, Middleton

Listing courtesy of Real Broker LLC.

$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.

$619,900
4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Under construction; estimated completion 12/1/26. Welcome to Redtail Ridge?featuring Middleton Schools! Cook?s kitchen with quartz countertops, granite sink, ceramic tile backsplash, stainless steel appliances, and walk-in pantry. Great room features gas fireplace with ceramic surround & reeded wall accent. Dining area includes walkout to 6x12' patio. Main floor flex room with double glass doors for office, playroom, etc. Primary bedroom suite features two closets?one standard and one walk-in!?and private bath with tile shower & dual sinks. Convenient upper level laundry room and separate mudroom with built-in wood cubbies off garage. Garage features bonus 15? deep 3rd car space. Basement is stubbed for bathroom & includes egress window for future expansion. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos are of a similar model. Plans & design selections available upon request.

6648 Redpoll Road, Middleton

Listing courtesy of Encore Real Estate Services, I.

$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.

$624,900
4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Welcome home to this beautiful 4-bedroom home in the highly sought-after Middleton School District! A charming covered front porch welcomes you into a bright, open-concept floor plan designed for comfortable everyday living and entertaining. The great room features a cozy fireplace and flows seamlessly into the kitchen with a spacious island. Enjoy the convenience of a main-floor primary suite complete with a private en suite featuring a tiled shower and double vanity. Main-floor laundry and a 3-car garage add functionality and storage. Upstairs, you?ll find three additional bedrooms, a full bathroom, and a versatile flex room?perfect for a home office, playroom, den, craft room, or whatever fits your lifestyle. With a thoughtful layout, flexible living spaces, and a desirable location close to shopping and nature, this home has so much to offer! October completion

6659 Linnet Lane, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$634,900
4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Energy Efficient New Construction located in the highly sought after Middleton School District. Tim O'Brien Homes Abbott plan welcomes you from the covered front porch inviting you into an open living space where the bright sunny Great Room features a cozy fireplace & is open to a spacious Kitchen and dining area. The quartz counters & ample cabinetry make this kitchen a chef's dream. A Flex Room is located off the main living & provides a quiet area perfect for an office or formal dining. In the expansive upper level find 4 bedrooms including the impressive Primary Suite w/ box tray ceiling, a large walk-in closet & luxurious bath w/ tile shower and bench. An additional flex room on the upper level offers endless possibilities. An egress window in the lower level allows for future potential finished basement. Plenty of room in the 3 car garage. Don't miss this Middleton gem! December completion

6610 Linnet Lane, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$642,900
3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Energy Efficient New Construction located in the highly sought after Middleton School District. Tim O'Brien Homes Abbott plan welcomes you from the covered front porch inviting you into an open living space where the bright sunny Great Room features a cozy fireplace & is open to a spacious Kitchen and dining area. The quartz counters & ample cabinetry make this kitchen a chef's dream. A Flex Room is located off the main living & provides a quiet area perfect for an office or formal dining. In the expansive upper level find 3 bedrooms including the impressive Primary Suite w/ box tray ceiling, a large walk-in closet & luxurious bath w/ tile shower and bench. An egress window in the lower level allows for future potential finished basement. Plenty of room in the extra wide 2 car garage. Don't miss this Middleton gem! November completion

6622 Linnet Lane, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$750,000
3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Spacious, updated ranch-style condo in Bishop's Bay with a main-level primary suite and a new roof. The open-concept kitchen and living room feature bamboo flooring and a gas fireplace, while the eat-in kitchen offers solid surface counters, a gas range with hood vent, and abundant storage. Step outside to the private, covered composite deck ? perfect for grilling or fresh air. The large primary suite impresses with custom built-ins, a walk-in shower, jetted tub, and an oversized walk-in closet. Downstairs, brand-new carpet runs throughout the expansive walk-out living space, complete with a second gas fireplace and a concrete patio. Two additional bedrooms, a full bath, and a private office round out the lower level. Recent updates include a new furnace, A/C, and water heater ('23) and new lower-level flooring('26). Topping it all off is a rare, oversized 4 car garage ? plenty of room for cars, boats, and all your toys. There's simply too much to list ? schedule your showing

5021 Prairie Rose Court, Middleton

Listing courtesy of Restaino & Associates.

$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.

$999,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status
What sets this incredible property apart is clear before you even step inside. This contemporary home is surrounded by carefully tended prairie and woods, a thriving habitat for birds, pollinators, and wildlife. Architect Bruce Nichols designed this home with one intention: to bring the outside in. Floor to ceiling windows and skylights draw natural light deep into the heart of the home. The open kitchen w/pantry and lg island flows easily into the family room and sunny bfast nook, w/hardwood floors throughout. Guest bed + bath on main level w/primary suite + 2 beds/bath up. Glass railing overlooks the 2-story great room w/gas FP. Primary suite is a sanctuary of its own w/gas FP, oversized WIC, and bath w/shower and whirlpool tub. Solar panels, whole house fan, and updated mechanicals. Middleton schools w/low Town of Middleton taxes and nearly 2 acres of seclusion combine to create a package that rarely comes to market. If you?ve been waiting for something truly different, this is it.

8685 Airport Road, Middleton

Listing courtesy of Mode Realty Network.

$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.

$3,750,000
4 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
15+ breathtaking acres create one of the most impressive private estates in the Town of Middleton. Rolling countryside views, beautiful white fencing, and a true park-like setting surround this extraordinary equestrian property. Perched high above the estate, the custom-built home overlooks the entire property and offers hardwood floors, 3 fireplaces, 2 full kitchens, 2 laundry areas, and a walkout lower level with seamless access directly to the pool deck. Outside, enjoy a resort-style retreat with an inground pool, waterslide, overflowing hot tub, pool house, and outdoor shower. Equestrian center built for year-round use, the approximately 20,000 sq ft heated complex features indoor and outdoor riding arenas, oversized garage doors, multiple barns and outbuildings, automatic waterers, offices, kitchens, 2 septic systems, hay storage, five fenced pastures, a lower barn with walk-in/out animal access, and a private basketball court.

3440 Meadow Road, Middleton

Listing courtesy of First Weber Inc.

$626,900
3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Located in the heart of the highly sought-after Middleton School District, this stunning 3-bedroom, 2.5-bathroom home offers the perfect blend of comfort, space & functionality. Step in from the large covered front porch to a welcoming spacious living area w/ charming fireplace perfect for relaxing evenings. The open layout flows seamlessly into the kitchen w/ ample counter space, walk in pantry & attached dining area with room to gather.. A generous primary suite w/ ensuite bath w/ tiled shower and walk-in closet, plus 2 additional bedrooms each with walk in closets, a full bath and conveniently located second floor laundry round out this thoughtfully laid out home plan. Plenty of space in the 3 car garage. An egress window in the lower level allows potential for a future finished basement. Don't miss out on this Middleton gem! Photos of similar model.

6625 Junco Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$614,900
3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Located in the heart of the highly sought-after Middleton School District, this stunning 3-bedroom, 2.5-bathroom home offers the perfect blend of comfort, space & functionality. Step in from the covered front porch to a welcoming spacious living area w/ charming fireplace perfect for relaxing evenings. The open layout flows seamlessly into the kitchen w/ ample counter space, walk in pantry & attached dining area with room to gather.. A generous primary suite w/ ensuite bath and walk-in closet, plus 2 additional bedrooms each with walk in closets, a full bath and conveniently located second floor laundry round out this thoughtfully laid out home plan. Plenty of space in the 3 car garage. An egress window in the lower level allows potential for a future finished basement. Don't miss out on this Middleton gem! Photos of similar model. Move in ready!

6671 Linnet Lane, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$1,150,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status
Discover timeless Mid-Century Modern ranch living in the heart of Middleton. This nearly 3,500 sqft home offers exceptional space & a premier location just one block from the conservancy. This unique 5BR/4BA residence is designed for flexible living. Occupy the spacious 4BR main level while generating income from the private-entry MIL suite w/ indoor parking. A separate LL apartment with its own entrance provides add'l privacy, ideal for multigenerational living or rental. Inside, vaulted timber ceilings, pine floors & expansive windows create a bright, light-filled interior. A stunning stone fireplace anchors the main living area, with a 2nd fireplace in the LL. Located near top-rated schools, parks & 2 blocks from the bus line, this home perfectly blends comfort, flexibility & location.

6644 Columbus Drive, Middleton

Listing courtesy of Mahler Sotheby's International Realty.

$1,399,000
4 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
RECENTLY UPDATED RED BIRCH FLOORS, NEW ROOF, DECK RAILINGS & MORE! Timeless architecture meets modern sophistication in sought-after Middleton Hills. This exceptional 4+ bedroom, 4.5 bath home offers over 4,600 sq ft across three expansive levels, featuring two spacious primary suites with walk-in closets. The premium open-concept kitchen features high-end appliances and flows seamlessly into inviting living and entertaining spaces. The light-filled lower level includes a theater, fireplace, kitchenette, and guest suite. Two offices provide ideal work-from-home flexibility. Enjoy prized green space on two sides, and a screened porch and patio for outdoor living. Luxury bath features include a heated floor, a wall-mounted toilet, walk-in showers, jet tubs, plus laundry on two levels. EV-ready 3+car side-entry garage. Walk to schools, parks, trails, groceries and shops.

6833 Phil Lewis Way, Middleton

Listing courtesy of MHB Real Estate.

$2,750,000
4 Beds ⋅ 4.5 Baths ⋅ 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 Court, Middleton

Listing courtesy of Sprinkman Real Estate.

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.