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$2,100,000
4 Beds ⋅ 4 Baths ⋅ 2028201 MLS ⋅ ACTIVE Status
Middleton Schools! Lake Mendota living w/72' of prime level frontage, Capitol views & minutes from Middleton's dining, shopping & amenities. Owned by the same family for 55 yrs this beautifully updated 4-bed, 3.5-bath waterfront home blends timeless character w/modern comfort. Remodeled main level features a wonderful kitchen w/new cabinetry, granite counters & stainless steel appliances. Open floorplan flows into the living rm featuring wood-burning fireplace, expansive windows & panoramic lake views. Step onto the lakeside deck for outdoor living & entertaining. Family rm offers an additional gathering space & possible 2nd dining area. Spacious primary suite showcases spectacular lake views, private bath & sitting area w/potential for a custom walk-in closet. Walkout lower level includes rec room w/fireplace, new patio, den & flex space. Updates incl: New flooring/windows/patio drs in LL & main floors, driveway & front stoop. Oversized garage w/epoxy flooring. Close to downtown & UW.

3017 Dianne Dr, Middleton
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 2027824 MLS ⋅ ACTIVE Status
Every detail of this beautifully updated home has been thoughtfully curated to create a space that's both elegant and inviting. The stunning remodeled kitchen features custom cabinetry, marble countertops, a Kohler farmhouse sink, brass hardware, and a commercial-grade appliance package. A stylish wet bar with a beverage fridge makes entertaining effortless, while luxury vinyl plank flooring flows throughout the home, there's no carpet. The expansive primary suite is a true retreat, featuring vaulted ceilings, oversized windows that fill the room with natural light, and a spa-inspired bath with marble countertops, a spacious vanity, designer tile, and premium finishes. Outside, enjoy a fully fenced 0.72-acre yard surrounded by mature trees and lush landscaping, creating a private setting with plenty of space to relax or entertain. Just minutes from downtown Madison, this move-in-ready home offers the perfect blend of luxury, comfort, and convenience

3944 Caribou Rd, 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
$1,750,000
5 Beds ⋅ 6 Baths ⋅ 2027081 MLS ⋅ ACTIVE Status
Exceptional custom home offering timeless design, luxurious amenities, & exceptional living spaces throughout. The grand foyer opens to elegant formal living & dining rooms, while the dramatic two-story great room showcases a floor-to-ceiling stone fireplace, custom built-ins, & a wall of windows overlooking the private backyard. The chef's kitchen features a Wolf induction range, Sub-Zero refrigerator, Bosch dishwasher, granite island, & walk-in pantry, w/adjoining dinette leading to the screened porch & maintenance-free deck. The luxurious primary suite offers a lighted tray ceiling, 3-sided fireplace, sitting area w/private balcony, spa-like bath, & dual walk-in closets. The finished walkout LL includes a spacious family room w/fireplace, theater room, exercise room, & guest suite. Additional highlights include a bonus room, central vacuum, Hunter Douglas automatic blinds, 2 new zoned Lennox furnaces (2025), & an exceptional floor plan designed for everyday living & entertaining.

7534 Summit Ridge Rd, Middleton
$1,690,000
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
$609,000
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
$1,495,000
5 Beds ⋅ 5 Baths ⋅ 2024433 MLS ⋅ ACTIVE Status
Set on a beautiful 0.92-acre lot, this home offers timeless architecture, refined finishes, and thoughtful updates in one of the area’s most exclusive neighborhoods. The home features 5 bedrooms, walk-in closets, 4 full baths, and a main level powder room, with a finished lower level filled with natural light. Brazilian cherry floors, exquisite ceilings, custom millwork, and built-in bookshelves showcase the exceptional craftsmanship throughout. The library offers a gas fireplace, while the family room provides a welcoming gathering space that opens to the outdoors. The custom kitchen is appointed with Sub-Zero and Wolf appliances, including a four-burner gas stove with griddle, beverage refrigerator, maple and cherry cabinetry, a butler’s pantry, and reverse osmosis filtration. Outdoor living is enhanced by Trex decking added in 2026. Additional highlights include a 3-car garage, security system, central vacuum, new HVAC (2023), new water heater (2024), & new washer and dryer (2024).

4516 Nina Ln, Middleton
$725,000
3 Beds ⋅ 4 Baths ⋅ 2025796 MLS ⋅ ACTIVE UNDER CONTRACT Status
Showings to start 6/26 at the open house. Backing to peaceful green space, this beautifully appointed 3-bedroom, 3.5-bath home offers the perfect blend of privacy, comfort, and everyday functionality. Soaring vaulted ceilings and a cozy gas fireplace create a warm, inviting living room, while the kitchen is designed for gathering with a large island, breakfast bar, and dinette that opens to the deck. Escape to the spacious primary suite featuring a walk-in closet, soaking tub, and walk-in shower. The finished lower level adds incredible flexibility with a rec room, office/den, and full bath. Complete with a 3-car garage, main-level mudroom and laundry, whole-home humidifier, and direct access to neighborhood green space and a favorite sledding hill, this home is one you'll want to experience in person.

4230 Redtail Pass, Middleton
$449,900
4 Beds ⋅ 2 Baths ⋅ 2025917 MLS ⋅ ACTIVE UNDER CONTRACT Status
Opportunity awaits in this 4-bedroom, 1.5-bath home located on a desirable corner lot in an established Middleton neighborhood. Many of the major updates have already been completed, including a new roof (2025), renovated bathrooms (2025), windows (2021), siding (2021), furnace (2020), and A/C (2020). The main level offers a functional layout with a dedicated office/den, providing flexibility for work or hobbies. Hardwood under all carpeting. Outside, enjoy established gardens, a raspberry patch, and a spacious deck for enjoying the backyard. Bring your ideas and personal touches, this home offers solid fundamentals and potential to create your ideal living space. Don't miss your opportunity to build equity in a sought-after location close to parks, schools, and downtown Middleton.

1605 Maple St, Middleton
$1,500,000
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
$849,900
5 Beds ⋅ 4 Baths ⋅ 2025527 MLS ⋅ ACTIVE Status
Experience luxury living in Middleton's highly sought-after Bishops Bay community! This stunning 5-bed home offers exceptional space, thoughtful design, & high-end finishes throughout. Hardwood floors welcome you into the open-concept main level featuring a flexible front sitting/dining space, inviting living room with gas fireplace, and a chef's kitchen complete with granite countertops, oversized island, mosaic tile backsplash, stainless steel appliances, pantry, and sunny dinette. Upstairs, 4 spacious bedrooms each boast walk-in closets, including the elegant primary w/ dual walk-in closets, double vanity, soaker tub, and tiled shower! Convenient upstairs laundry adds everyday ease. The finished walkout lower level is built for entertaining with a wet bar, theater room w/ tiered seating, projector and surround sound, electric fireplace, exercise rm, fifth bedroom, and full bath. Enjoy the trex deck & 3-car garage —all in one of Middleton's premier neighborhoods. See docs for more!

5023 Congressional Hl, Middleton
$695,000
3 Beds ⋅ 4 Baths ⋅ 2025413 MLS ⋅ ACTIVE Status
Enjoy this Town of Middleton Stonebrook Estates 3 bedroom propertunity nestled on nearly .5 acres next to a 5-acre park setting. Look no further if you are looking for privacy, room to roam with the 66-acre walking trails/land or crave the active opportunities riding your bike to Settlers Park overlooking the local prairie/savanna. The backyard is perfect to practice your World Cup skills or work on your 9-iron aim over your vegetable/flower gardens. Soak in nature as you relax on the deck or patio while you fire up the smoker for your favorite BBQ. The inside layout is ideal for quality time together with enough space to focus on your work/projects with privacy. The inviting cooks kitchen has abundant counter space to cook together or meal prep for the week. Abundant storage not only in the kitchen but throughout the home. After a fun day in the neighborhood enjoy a relaxing soak in the tub or retreat to the exposed lower level for game or a movie night. New roof, AC, furnace, deck.

8600 Ellington Way, Middleton
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 2023237 MLS ⋅ ACTIVE UNDER CONTRACT Status
This private estate sits on 1.6 acres with sweeping views & no HOA. The gourmet kitchen has Wolf range/double ovens, SubZero fridge, warming drawer, 4 beverage drawers, + a striking swirled black marble island. The main level incl a spacious living room w/fp, formal dining, office, sunroom + laundry/mudroom. The expansive primary offers a 2 room WIC + spa bath w/glass shower + tub. The walk out LL is an entertainer’s dream with a 2nd kitchen, wine cellar, enormous rec room, indoor basketball court, plus a sauna. Add'l highlights incl: commercial grade whole house generator, elevator to all 3 levels, smart home features, 5 car garage, loads of built-ins, SunSetter awning w/lighting. A rare combination of privacy, luxury, + unmatched amenities!

3576 Timber Ln, Middleton
$1,190,000
5 Beds ⋅ 5 Baths ⋅ 2021591 MLS ⋅ ACTIVE Status
Showings start May 2nd. Available for the first time in 28 years. Rarely available in Applewood you'll love a solid Brick exterior with a shake roof on a private wooded lot in the Middleton School district just minutes from all west side amenities! 5 beds 4.5 bath 3 car w electric charger and a light filled two story sunroom make this the one. A quiet and peaceful respite from the city and close enough to enjoy everything Madison has to offer.

6993 Applewood Dr, Middleton
$799,000
3 Beds ⋅ 4 Baths ⋅ 2021477 MLS ⋅ ACTIVE Status
Who says you cannot live beautifully in a smaller footprint? These cozy and light-filled standalone homes are a joy & a rarity... combining high quality, high functionality & attention to design. This home at Belle Farm serves as a peaceful antidote… an example that less can be more. Inspiring interiors, front porches & secluded side yards allow for both privacy & opportunities to connect. Solar panels and geothermal HVAC mean lower energy bills & more resilience in the face of power outages. This ready to build home on Lot 8 starts at $799,000 including lot price & features a metal roof, solid hardwood floors, Wolf range, Bosch refrigerator & dishwasher, EV-ready wiring & curated interiors. Belle Farm was founded on the idea that there is a different way. That the places we live can & should inspire us, connect us, help us be healthier in mind & body, & reduce our environmental impact.

4054 Serenbe St, Middleton
$1,599,000
5 Beds ⋅ 6 Baths ⋅ 2017783 MLS ⋅ ACTIVE Status
Experience a rare combination of design, efficiency, and low-maintenance living in this move-in ready home at Belle Farm. The main level is anchored by a private first-floor primary suite and a seamless connection between kitchen, dining, and den, with hardwood floors, a wood-burning fireplace, and SubZero, Wolf, and Cove appliances. All bedrooms in the main home feature en suite baths, offering comfort and privacy throughout. Above the garage, a separately accessed 1 bed, 1 bath apartment provides uncommon flexibility for multigenerational living, guests, extended stays, or a private workspace. Solar, geothermal heating and cooling, and a metal roof are integrated from the start, prioritizing long-term efficiency and durability. HOA-managed landscaping and snow removal support a true lock-and-leave lifestyle. Option to finish the basement for an additional 520 sq ft.

4029 Serenbe St, Middleton

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