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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

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

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

2609 Middleton Beach Rd, Middleton
$1,363,000
2 Beds ⋅ 2 Baths ⋅ 2033356 MLS ⋅ CLOSED Status
Rare opportunity to enjoy lake living from an exceptional setting at the end of a quiet dead-end street with 45 feet of lake frontage and some of the area's most impressive long-water views, including beautiful sunrises and moonrises over the lake. This well-maintained home currently offers two bedrooms, highlighted by a remarkable primary suite that occupies the entire second floor and creates a spacious, private retreat. The floor plan also offers a straightforward and relatively inexpensive opportunity to add a third bedroom with minimal impact to the existing living spaces. The location is equally special, with easy access to the 600+ acre Pheasant Branch Conservancy, Harbor Athletic Club, restaurants, Starbucks and more, all while coming home to an unusually private waterfront setting with exceptional end-to-end lake views.

2609 Middleton Beach Rd, 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

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

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

3921 Swoboda Rd, Middleton
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 2021448 MLS ⋅ CLOSED Status
New Roof! New Gutters! New Price! Middleton Schools! Stately custom-built residence offers refined comfort & exceptional space, thoughtfully designed & maintained by its original owners for 25 years. With 4,840 square feet above grade, this home features expansive living areas filled with natural light from walls of windows framing serene views of the beautifully landscaped 1.27-acre lot. Main level includes a welcoming living room with a fireplace & beautiful built-ins, formal dining room, & den with cozy fireplace! Impressive first-floor primary suite is a true retreat, featuring dual vanities, separate shower, jetted soaking tub, and a generous 12x12 walk-in closet. Spacious secondary bedrooms provide comfort & flexibility for family or guests. A 4-car heated garage adds year-round convenience. Unfinished lower level offers a true blank canvas for future living space. Lush yard showcases established perennials & backs to mature woods (maintained by HOA!) creating a private setting.

3921 Swoboda Rd, Middleton

5003 Wenlock Rose Ct, Middleton
$1,200,000
2 Beds ⋅ 3 Baths ⋅ 2016808 MLS ⋅ CLOSED Status
Experience refined living on Bishop’s Bay golf course in this fully renovated condo. Recent high-end transformation showcases exceptional craftsmanship + elevated design thru-out. Stunning kitchen offers 2 islands, quartz counters, custom cabs, + high-end appliances Wolf, Bosch + Sub-Zero. ML boasts new hardwood floors, gas fireplace, lux primary suite w/ heated tile bath floors & large walk-in shower. Walk-out LL offers flex space, full bath, bar area w/ bev fridge, wine cooler + ice maker, plus two addtl rooms. Outdoor living shines w/ screened porch w/ composite decking + large paver patio space w/ gas line for grilling. Major mechanical upgrades include 2025 Bryant Evolution furnace & A/C w/ zoning + WiFi thermostats. Oversized garage fits 2 cars plus golf cart, includes epoxy flooring, storage racks, utility sink, + EV pre-wire. Luxury living at its finest.

5003 Wenlock Rose Ct, Middleton

3466 Nappe Dr, Middleton
$1,199,000
4 Beds ⋅ 4 Baths ⋅ 2018493 MLS ⋅ CLOSED Status
Rare stand-alone condominium in the prestigious, gated Villages of Bishop’s Bay overlooking a serene private pond and filled with abundant natural light. This thoughtfully updated 4-bedroom, 3.5-bath home offers over 3,700 square feet across two beautifully finished levels. Brand-new wide-plank white oak hardwood floors span the main level, while new luxury flooring and carpeting enhance the walkout lower level. The updated kitchen was designed for entertaining, anchored by a dramatic 13-foot Breccia Venezia marble waterfall island. Expansive windows frame the tranquil water, bringing the outdoors in and creating a peaceful retreat year-round. Two spacious main-level bedrooms each offer the privacy and scale of a potential primary suite. The lower level adds two bedrooms, a full bath, generous living space, a screened porch, and a private deck overlooking the pond. Ample storage throughout and a rare private dock complete this refined, low-maintenance luxury home.

3466 Nappe Dr, Middleton

7910 Black River Rd, Middleton
$1,120,000
5 Beds ⋅ 4 Baths ⋅ 2021315 MLS ⋅ CLOSED Status
Extensively remodeled in 2023, this exquisite home blends comfort, style & space in all the right ways. A welcoming foyer opens to airy, sun filled living areas with vaulted ceilings and an easy, natural flow that makes everyday living and entertaining feel effortless. With 5 bedrooms & 2 flexible dens, there’s room to spread out - whether for work, guests, or quiet moments at home. The chef’s kitchen connects seamlessly to both formal and casual spaces, while the finished lower level lives like its own retreat - featuring a spacious family room, 5th bedroom, den, full bath & wet bar - ideal for guests, extended stays or relaxed evenings in. Step outside to a fenced half-acre retreat with lush landscaping, a composite deck & expansive brick patio with pergola & fire pit, plus a large outdoor shed with metal roof & loft storage area! All just moments from nearby trails and conservancy land. Room to live, space to breathe and a setting that just feels good.

7910 Black River Rd, Middleton

3576 Timber Ln, Middleton
$1,105,000
4 Beds ⋅ 4 Baths ⋅ 2023237 MLS ⋅ CLOSED 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

3944 Caribou Rd, Middleton
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 2027824 MLS ⋅ CLOSED 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

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