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7616 Tumbledown Trl, Middleton
$1,590,000
5 Beds ⋅ 5 Baths ⋅ 2026810 MLS ⋅ 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 Trl, Middleton

8685 Airport Rd, Middleton
$999,900
4 Beds ⋅ 3 Baths ⋅ 2026028 MLS ⋅ 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 Rd, Middleton

4057 Morning Poem Pl, Middleton
$1,199,000
4 Beds ⋅ 4 Baths ⋅ 2025953 MLS ⋅ ACTIVE Status
Welcome to this thoughtfully designed home at Belle Farm offering main level living with a private primary suite & an open concept kitchen, living, & dining area. The living space is light-filled & functional, with hardwood floors, wood-burning stove, & a well-appointed kitchen featuring Sub-Zero, Wolf & Cove appliances. Above the garage, a separately accessed 1 bed, 1 bath ADU provides flexibility for guests, extended stays, multigenerational living, a caregiver, or a home office. Lower level includes additional bedrooms & living space, offering separation & versatility. Built with resilience in mind, the home includes solar, geothermal HVAC, & is wired for EV charging. HOA covers lawn care & snow removal, making ownership low-maintenance & easy for travel.

4057 Morning Poem Pl, Middleton

7119 Johann Farm Rd, Middleton
$659,900
4 Beds ⋅ 3 Baths ⋅ 2025847 MLS ⋅ ACTIVE Status
This Everest home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 4 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler® and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

7119 Johann Farm Rd, Middleton

1308 Shirley St, Middleton
$639,900
4 Beds ⋅ 2 Baths ⋅ 2025170 MLS ⋅ ACTIVE Status
Exceptional opportunity in sought-after Woodside Heights! Charming mid-century modern raised ranch just 1 blk fr Stricker's Pond, on quiet, tree-lined street walking distance to dwntn Middleton & schools. Spacious Great Room flows into Sun Room with dramatic tongue & groove vaulted wood ceiling, recessed lighting, hardwood floors, gas fireplace & extensive built-in wood shelving & cabinetry. Open kitchen w/cooktop island & casual dining counter connects easily to the living areas & overlooks pool & backyard. Generous windows bring the outdoors in. Extensive recent landscaping has transformed the fully fenced backyard, creating significantly more open, usable lawn & recreation space. In-ground pool with newer liner & heater (2023), slide, & stone-paved decking creates a private retreat for entertaining, relaxing & summer fun into the fall. Fresh paint & new cpt throughout. Generous living space, mid-century character, a fabulous backyard and pool—all in a location that's hard to beat!

1308 Shirley St, Middleton

9715 Red Sky Dr, Middleton
$1,450,000
5 Beds ⋅ 5 Baths ⋅ 2023786 MLS ⋅ 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 Dr, Middleton

719 Cricket Ln Unit 1, Middleton
$347,719
3 Beds ⋅ 3 Baths ⋅ 2021318 MLS ⋅ ACTIVE UNDER CONTRACT Status
$3k credit for closing costs or rate buy-down. Numerous updates; NEW furnace & A/C, water softener, water heater, dishwasher, refrigerator, and washer & dryer! Close in time for start of school! This well-cared-for condo offers spacious, low-maintenance living in a highly desirable Middleton location. The bright, open-concept main level is designed for both everyday living & entertaining, featuring a generous living room w/cozy gas fireplace, a dining area w/access to a private deck, & an updated kitchen; complete w/SS appliances, breakfast bar, & abundant cabinetry. Upstairs, you'll find generously sized bedrooms, including a spacious primary suite w/a WIC & private bath. 2nd bedroom also boasts its own en suite bathroom, while the 3rd bedroom offers flexibility as a home office, fitness room, or addtl living space. Convenient upper-level laundry, a private attached 2-car garage. Ideally located near parks, walking trails, shopping, dining & more! Priced under assessed value.

719 Cricket Ln Unit 1, Middleton

7527 Fallen Oak Dr, 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

3440 Meadow Rd, Middleton
$3,750,000
4 Beds ⋅ 5 Baths ⋅ 2023109 MLS ⋅ ACTIVE UNDER CONTRACT 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 Rd, Middleton

3319 Saracen Way, 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

2140 Allen Blvd Unit 3, Middleton
$189,900
2 Beds ⋅ 1 Baths ⋅ 2020794 MLS ⋅ ACTIVE Status
Welcome to this beautifully updated 2-bedroom, 1-bath condo in an unbeatable Middleton location. The refreshed kitchen features quartz countertops, white cabinetry and stainless steel appliances, flowing seamlessly into a bright and comfortable living space. Enjoy a quiet, private setting from your balcony that feels like you’re nestled in the trees, perfect for morning coffee or evening unwinding. Ideally located directly across the street from Marshall Park on the shores of Lake Mendota, offering easy access to trails, green space and waterfront activities. Additional highlights include a private 1-car garage, ample surface parking for residents and guests and a dedicated storage unit. HOA dues cover heat and hot water, adding convenience and value to this exceptional opportunity.

2140 Allen Blvd Unit 3, Middleton

2809 Dewey Ct, Middleton
$1,000,000
3 Beds ⋅ 2 Baths ⋅ 2019384 MLS ⋅ ACTIVE UNDER CONTRACT Status
Two lots create a rare opportunity along a quiet channel with direct access to Lake Mendota, inviting a range of possibilities from thoughtful renovation to a ground-up custom build. The existing home sits between two buildable parcels, allowing for expanded outdoor space, future development, or a private lakeside retreat tailored to your vision. Spend mornings on the water boating or fishing, then return to a backyard dock, with a nearby boat launch adding everyday ease. The setting balances a sense of retreat with practical convenience, just off Century Avenue and minutes from local grocers, dining, and daily essentials. Downtown Madison is an easy 20-minute drive, making this an ideal blend of waterfront living and city access.

2809 Dewey Ct, Middleton

6833 Phil Lewis Way, Middleton
$1,399,000
4 Beds ⋅ 5 Baths ⋅ 2017387 MLS ⋅ 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

7135 Johann Farm Rd, Middleton
$589,900
3 Beds ⋅ 3 Baths ⋅ 2016454 MLS ⋅ ACTIVE Status
This Emerald home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler® and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

7135 Johann Farm Rd, Middleton

2914 Hambrecht Rd, Middleton
$470,000
3 Beds ⋅ 3 Baths ⋅ 2013959 MLS ⋅ ACTIVE Status
Back on the market - No fault of the Seller! Beautiful ranch home in a quiet neighborhood in the highly desirable Middleton School District. Great location just a short walk from Lake Mendota, local parks, and Pheasant Branch Trails. Conveniently located near restaurants, local shopping, and athletic club. Main level features kitchen with breakfast bar and pantry, a spacious great room with pass-through to kitchen and dinette. Basement level includes rec room, bedroom with electric fireplace and spacious walk-in closet, additional bathroom, and a fully exposed walk-out. Spacious deck and screen porch with built-in speakers that open out to a private fenced backyard complete the package. New roof as of March 2025. No HOA. Seller may be willing to leave some personal property. Buyer to verify dimensions if important.

2914 Hambrecht Rd, Middleton

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