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4743 Delmara Rd, Middleton
$3,500,000
4 Beds ⋅ 8 Baths ⋅ 2014199 MLS ⋅ CLOSED Status
Exceptional Hart DeNoble Builders custom-built luxury home on 10+ acres in Middleton. The main level features Brazilian cherry hardwood floors, soaring ceilings, crown molding, multiple living spaces, home office, & den. The gourmet kitchen offers high ceilings, crown molding, & a walk-in pantry, opening to a family room w/ coffered ceiling, fireplace, & built-ins. The stunning primary suite includes a sitting area & spa-like bath w/ in-floor heat. The finished walk-out lower level boasts 9’ ceilings, rec room, wet bar, fireplace, game room, exercise room, theater, 2 bedroom suites, additional laundry, & in-floor heating. Includes a 3-car attached heated garage & a 4 car detached carriage house w/ additional 1,732 sq ft. Enjoy seamless indoor-outdoor living w/ a screened porch & in-ground pool overlooking nature.

4743 Delmara Rd, Middleton

5511 Mendota Dr, Middleton
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 2017756 MLS ⋅ CLOSED Status
Sweeping views of Lake Mendota + WI State Capitol set the stage for this exceptional Middleton lakefront retreat. Expansive balconies overlook level lot designed for effortless outdoor living w/ paved patio, built-in gas grill, + hot tub. Perfect for capturing beautiful views + enjoying endless lake activities. Inside, impressive upgrades + stylish design create a refined yet comfortable space. Main level features spacious kitchen w/ professional appliances, quartz countertops, + open living/dining areas anchored by a fireplace + stunning lake views. Upstairs, luxurious primary suite offers a spa-like bath w/ heated tile floors, soaking tub, + walk-in shower. 3 addtl beds, full bath, + bonus room provides flexibility for fam room, playroom, office. Walkout lower level enhances lakeside entertaining w/ second kitchen, large rec room, + full bath, blending tranquility w/ vibrant waterfront living. See docs for addtl features + improvements.

5511 Mendota Dr, Middleton

3017 Dianne Dr, Middleton
$1,850,000
4 Beds ⋅ 4 Baths ⋅ 2028201 MLS ⋅ CLOSED 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

2529 Middleton Beach Rd, Middleton
$1,805,000
4 Beds ⋅ 3 Baths ⋅ 2020782 MLS ⋅ CLOSED Status
Set on the coveted sandy west shore of Lake Mendota, this beautifully updated home offers 40' of level frontage and stunning sunrise views. The open-concept design centers around a chef’s kitchen with oversized island, custom cabinetry, and high-end finishes, flowing seamlessly into bright living spaces and a glass sunroom overlooking the water. The luxurious primary suite captures panoramic lake views and features a spa-like bath with heated floors, soaking tub, and steam shower. A second ensuite with loft, third bedroom, and main-level bedroom/office with built-in Murphy bed complete the 4 bed, 3 bath layout. Oversized 2-car garage with epoxy floor and walk-up attic for storage. Enjoy the sandy shoreline and easy walk to restaurants, bars, Starbucks, a health club, and the 600+ acre Pheasant Branch Conservancy.

2529 Middleton Beach Rd, Middleton

7664 Badger Run Ct, Middleton
$1,685,000
5 Beds ⋅ 4 Baths ⋅ 2016898 MLS ⋅ CLOSED Status
Come home to everyday excellence in this stunning Parade of Homes Ranch! Top-tier finishes and thoughtful comfort shine bright in your 5BR/3.5BA Haven on .92 acres. Every detail crafted for owner enjoyment, blending classic and modern design. Exposed beams grace vaulted ceilings while natural light pours through floor-to-ceiling windows, creating warmth and flow. Savor cozy time by the fire in your private den or shut out the noise in a peaceful home office. Culinary adventures await in the tastefully designed kitchen featuring a gorgeous island and dining area. The luxurious Owner's suite boasts a spa-like bath with 5-head shower and soaking tub. Host movie nights or epic gatherings in the large lower level, complete with a theater room, wet bar, bedrooms, and exercise/flex space. Unwind by the fire pit with epic sunset views and enjoy perfect landscaping with irrigation. All complemented by the polished and heated 4-car garage for your toys. Don’t miss your chance to make this Home!

7664 Badger Run Ct, Middleton

3952 Caribou Rd, Middleton
$1,684,380
5 Beds ⋅ 7 Baths ⋅ 2027557 MLS ⋅ CLOSED 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

7576 Colonial Way, Middleton
$1,660,000
5 Beds ⋅ 5 Baths ⋅ 2019881 MLS ⋅ CLOSED Status
Custom-built, one-owner home offering exceptional space and high-end finishes throughout. The main level features a dramatic great room with soaring ceilings, expansive windows, and a floor to ceiling stone surround gas fireplace. Gourmet kitchen with large island, six-burner cook top, double ovens, vast walk-in pantry, and premium appliances. Enjoy a sun room with stone surround gas fireplace. Formal dining overlooking a maintenance-free deck. French doors lead into the private den. Mudroom w/ cubbies & closet. Laundry w/ sink & cabinets. The luxurious primary suite includes a tray ceiling, dual walk-in closets, soaking tub, and tile shower w/ dual heads. Three additional bedrooms share a full bath. The finished lower level offers a large rec room with wet bar, media room, 5th bedroom w/ private bath, and powder room. Additional highlights include a heated 4+ car garage w/ stairs to LL. Expansive patio, zoned HVAC, and extensive smart and mechanical upgrades. Mature landscaping.

7576 Colonial Way, Middleton

7545 Tumbledown Trl, Middleton
$1,640,000
4 Beds ⋅ 4 Baths ⋅ 2007979 MLS ⋅ CLOSED Status
Stunning Mark Solner design backing to golf course! Subzero 36" refrigerator & freezer, Wolf ovens, waterfall quartz island, natural wood Amish cabinets, walk-in pantry, laundry/mud rm, 11 ft living room ceiling, 2 fireplaces, expansive natural light on main level, screen porch, private master with ensuite bath & closet, 2 additional private bdrms. Hidden walk out w/wet rm direct to back yard/patio. LL boasts 4th bedroom/new full bath, 2 offices, $150k music/sound rm, huge exercise rm, 2nd kitchen, family rm w/custom builtins, storage. Interior freshly painted, new flring-main bdrms, new master closet & pantry, heated 3 car garage w/poly floor and Span Crete floor system. Stairs from garage to LL, no step entrances, Anderson windows, Hansgrohe fixtues, sprinkler system, Middleton Schools

7545 Tumbledown Trl, Middleton

4917 Breakers Rock Rd, Middleton
$1,600,000
4 Beds ⋅ 5 Baths ⋅ 2021228 MLS ⋅ CLOSED Status
Set within the sought-after Community of Bishops Bay, this thoughtfully designed home pairs refined finishes with everyday ease. Maple hardwoods carry through the main level, where a chef’s kitchen is anchored by Wolf double + steam ovens, Sub-Zero refrigeration, a 44" Galley workstation sink, granite countertops, and a hidden walk-in pantry with second dishwasher and sink. The great room centers on a gas fireplace with custom built-ins, while a four-season dining space adds warmth with a 74" fireplace. The main floor primary suite is a true retreat with quartzite counters, heated floors, and a tailored walk-in closet. Upstairs, a finished bonus room offers flexibility. The lower level is designed for gathering, with a theater, library with rolling ladder, and a bar area with fireplace. Electric blinds, dual-zone HVAC, whole-home audio, dog shower, and a sprinkler system complete the experience with no detail overlooked.

4917 Breakers Rock Rd, Middleton

7672 Leta Way, Middleton
$1,565,500
5 Beds ⋅ 4 Baths ⋅ 2023650 MLS ⋅ CLOSED Status
Designed by renowned architect Ed Linville, this stunning prairie-style home offers timeless architecture, modern updates, and breathtaking natural surroundings within walking distance to the Ice Age Trail. Set on 1.5 beautifully curated acres, the property features panoramic long-distance views with unforgettable sunsets. The fully updated interior centers around an expansive open-concept chef’s kitchen designed for both everyday living and entertaining. Generous living spaces are filled with natural light and seamlessly connect to the incredible outdoor scenery. The grounds offer a harmonious mix of natural prairie, professional landscaping, organic vegetable gardens, and mature trees that provide both beauty and privacy. An attached 2-car garage plus an additional detached 4-car garage provide exceptional storage and flexibility. Located in the Middleton-Cross Plains School District, this is an opportunity to own an architecturally significant home in an extraordinary setting.

7672 Leta Way, Middleton

4206 Rose Ct, Middleton
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 2017886 MLS ⋅ CLOSED Status
Tucked on 5 private acres backing Pleasantview Golf Course, this 3-bed, 3-bath home delivers space, privacy, and quality finishes throughout. The open main level showcases kitchen with cherry cabinetry, granite countertops, and stainless appliances with a living & dining area warmed by a gas fireplace. Deck off the main level overlooks an expansive, peaceful backyard. Primary with en suite, main floor laundry, and dedicated office add everyday functionality.Finished lower level features a family room with gas fireplace, 3rd bedroom, full bath, and walk-out to the backyard — ideal for guests or extended living. Two-car attached garage plus a two-car detached garage offers exceptional storage and workspace. A rare combination of acreage, privacy, and convenience. Room to breath, Room to grow.

4206 Rose Ct, Middleton

7569 Tumbledown Trl, Middleton
$1,425,000
4 Beds ⋅ 4 Baths ⋅ 2016706 MLS ⋅ CLOSED Status
Stunning custom home with golf course views and exceptional detail throughout. The great room showcases an 11’ coffered ceiling, floor-to-ceiling stone fireplace, and solid pecan hardwood floors. Gourmet kitchen features granite countertops, cherry cabinetry, stainless GE Café appliances, Blanco sink, beverage fridge, and spacious pantry. Sunroom with cedar walls, stone fireplace, and EZ-Screen windows opens to patio and fire pit. Luxurious primary suite offers tray ceiling, custom walk-in closet, and spa bath with whirlpool tub and dual-head tiled shower. Finished lower level includes family room with wet bar, fireplace, guest bedroom, bath, exercise room, and hot stone sauna. Heated 4-car garage, security system, central vac, and Middleton Schools.

7569 Tumbledown Trl, Middleton

4498 Nina Ln, Middleton
$1,420,000
5 Beds ⋅ 5 Baths ⋅ 2026869 MLS ⋅ CLOSED 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

7532 Peyton Pkwy, Middleton
$1,417,612
4 Beds ⋅ 4 Baths ⋅ 2010554 MLS ⋅ CLOSED Status
NEW CONSTRUCTION! Welcome to Evans Crossing. This house is located in an area of fine homes with strong architectural requirements and in a wooded setting abutting the Pioneer Pointe golf course via the Town trail system and in Middleton school system. The house packs a punch: main floor primary, laundry, sunroom, screened in porch, walk-in pantry, raised ceilings, living room, windows everywhere. In addition, home features a great, exposed LL with wet bar, exercise/flex room, additional bedroom and more. **No lawn mowing or snow removal for you! This HOA uniquely provides those services. Home backs to a protected vacant parcel and lined w/ trees. ***Home is under construction -- completion is June 2026 ready for summer! Complete, move-in ready home pkg including landscaping.

7532 Peyton Pkwy, Middleton

4539 Deering Trl, Middleton
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 2016229 MLS ⋅ CLOSED Status
Beautifully designed ranch home set in a quiet rural subdivision with surrounding woods for privacy, views and wildlife. This 4-bedroom, 4-bath home offers a first-floor primary suite, while all additional bedrooms are thoughtfully located in the walkout lower level, including a private en-suite bedroom. The main level features an updated kitchen with high-end stainless appliances, stylish backsplash, and beautiful hardwood floors. Enjoy a large dining room with built-in buffet, a comfortable living room with gas fireplace, a sitting room off of the dining room, and a flexible office/den. A spacious mudroom with laundry provides zero-entry access from the 3-car garage. The walkout lower level includes in-floor radiant heat, wet bar, cozy built-in reading nooks, and generous living space. Relax on the screened porch with no-maintenance decking or step out onto the deck leading to the yard. Newer tankless water heater and quality finishes complete this exceptional home.

4539 Deering Trl, Middleton

4329 Callaway Ct, Middleton
$1,340,000
4 Beds ⋅ 4 Baths ⋅ 2003620 MLS ⋅ CLOSED Status
A rare opportunity in the renowned Villas of Callaway Court in beautiful Bishops Bay, The Back Nine. Extremely private and quiet location overlooking the 5th fairway with plenty of land as a protective buffer, this exceptionally high quality Michael F Simon home filled with stunning architectural details sits on over half an acre of land and leaves little to be desired. Stunning, open, bright great room. A spectacular outdoor kitchen and large screened porch overlooking your private sanctuary with long, peaceful & natural views. Zero entry main level living with generous accommodations up. Large, finished, heated garage with overhead side service door. Huge, exposed basement with loads of room to expand. Snow removal & lawn care handled by the well run association.Truly amazing. Come see!

4329 Callaway Ct, Middleton

7705 Maas Dr, Middleton
$1,335,000
4 Beds ⋅ 3 Baths ⋅ 2015935 MLS ⋅ CLOSED Status
Set on one of the best lots in the neighborhood, this better-than-new home blends bright, modern design with clean architectural lines and high-end finishes throughout. Located in the highly sought-after Middleton Cross Plains School District, this stunning 4-bedroom, 3-bath home offers refined luxury and exceptional craftsmanship. The heart of the home is a chef’s kitchen featuring premium appliances, custom cabinetry, a striking 12-foot quartzite island, and a walk-in pantry. The kitchen flows into a light-filled great room with soaring ceilings and a gas fireplace. The main level includes a spacious primary suite with dual closets and a beautifully appointed ensuite bath with a tiled walk-in shower, along with a dedicated office and a second bedroom. The finished lower level offers two additional bedrooms, a full bar, space for entertaining, plus approximately 1,000 square feet of unfinished space ready for a future bedroom, gym, or media room. Pre-inspected for peace of mind.

7705 Maas Dr, Middleton

4691 Sunset Ridge Dr, Middleton
$1,300,000
5 Beds ⋅ 5 Baths ⋅ 2021588 MLS ⋅ CLOSED Status
Set within the quiet landscape of Sunset Ridge Estates, this 2007-built residence offers a refined retreat on a sprawling 0.75-acre lot. Spanning nearly 5,000 square feet, the home is defined by thoughtful architecture and a layout that balances entertaining spaces with intimate daily living. Rich cherry floors lead you through a light-filled interior where a great room serves as the anchor, complemented by a formal dining room + a gourmet kitchen featuring granite surfaces. The main level is designed for effortless flow, extending outdoors to a screened porch + deck overlooking fenced yard and green space with mature landscaping Five bedrooms + four-and-a-half baths include a primary suite designed for rest, while the exposed lower level adds versatility with a gym and additional living space. Complete with a two-car garage + meticulous finishes, this property offers a peaceful Middleton lifestyle just minutes from the city's energy. High-end living, grounded in nature.

4691 Sunset Ridge Dr, Middleton

6419 Stonefield Rd, Middleton
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 2020873 MLS ⋅ CLOSED Status
Sellers accepted a sight unseen offer. Welcome to this custom-built home, offering quality craftsmanship in highly sought-after Stonefield neighborhood! Open and bright floor plan featuring chef's kitchen w/ cherry cabinets, lg. island, and high end appliances. Open to cozy family room & airy sunroom for place to soak in the sunlight year round! Formal Dining and den/living room w/ one of two wood burning fireplaces (gas starters) Upstairs features a lg. Primary suite w/ vaulted ceilings, private office (easily a nursery or another bed w/ own door/closet), walk-in closet, private bath! 2 ample bedrooms w/ Jack & Jill bath and 4th bed w/ own staircase currently used as a great bonus room! LL rec room & lots of storage w/ ramp to fully insulated oversized 3 car garage for access & future hobbies. Sit outside on private deck or stone patio overlooking beautifully landscaped .47 acre lot. Cedar siding & shingles, Middleton Schools. This is a must SEE!

6419 Stonefield Rd, Middleton

1501 Beechwood Cir, Middleton
$1,300,000
5 Beds ⋅ 6 Baths ⋅ 2015358 MLS ⋅ CLOSED Status
Located on a quiet cul-de-sac in Middleton’s highly desirable Stonefield neighborhood, this exceptional home offers an impressive amount of living space rarely found in such a prime location. The thoughtfully designed main level features a stunning 4-season sunroom with vaulted ceilings that opens to a generous deck, perfect for relaxing/entertaining. The eat-in kitchen includes an island with built-in stools, & wood flooring. Multiple living and dining areas provide flexibility & charm, highlighted by striking wood beams & custom built-ins. A 1st flr primary suite with new carpeting offers the ease & convenience. Upstairs, 2 spacious bedrooms are connected by a Jack-&-Jill bath. The expansive lower level lives like a home of its own, complete with 2 additional bedrooms, exercise room, large family room with fireplace & walk-out access to the yard, 2nd kitchen, hobby room, unique fort room, & an impressive 20x21 workshop. An oversized 3-car garage w/ an epoxied floors adds more space.

1501 Beechwood Cir, Middleton

4516 Nina Ln, Middleton
$1,298,000
5 Beds ⋅ 5 Baths ⋅ 2024433 MLS ⋅ CLOSED 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

7724 Greenwood Rd, Middleton
$1,248,000
5 Beds ⋅ 4 Baths ⋅ 1993431 MLS ⋅ CLOSED Status
Discover your dream retreat nestled among 7.74 acres of scenic woodland, only 5 minutes from Madison and in Middleton School District! This solid-built house is not your “cook-cutter” house, but instead offers a wonderful combination of quality, updates and charm! The family room, with soaring cathedral ceilings and gorgeous brick fireplace, opens to a delightful three-season porch. Culinary enthusiasts will revel in the dream kitchen, outfitted with high-end appliances for both functionality and style, and lovely dining room creating the ideal setting for gatherings. The lower level of this home features a guest/in-law retreat and opens to your own privacy and pathway to the Ice Age Trail! The separate building/garage offers extra space plus an attached heated workshop for many activities

7724 Greenwood Rd, Middleton

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