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$850,000
3 Beds 4 Baths 2031753 MLS ACTIVE Status
Stunning stand-alone condo in desirable Settler Hill within Blackhawk! Grand 2-story entry opens to living room w/ 14' ceilings & floor-to-ceiling stone gas FP. Chef’s kitchen features granite & Quartz counters, white cabinets, SS appls: Bosch induction cooktop, Bosch dishwasher, GE oven, LG fridge, breakfast bar & dinette w/ built-ins. Custom bar w/ copper sink, wine fridge & mini-freezer. Private office w/ floor-to-ceiling built-ins & fireplace. Two spacious primary suites w/ adjoining baths. Sunroom w/ tile floors. Upper level offers loft w/ 3rd fireplace, 3rd bed, full bath & sauna. Exposed unfinished LL provides future expansion potential. ADT security system. 2-car attached garage. Exceptional space & maintenance-free living! Ultimate UHP included.

62 Settler Hill Cir, Madison

$574,900
3 Beds 3 Baths 2031729 MLS ACTIVE Status
Move-in ready 11/16/26. This Beryl 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.

7111 Johann Farm Rd, Middleton

$1,379,000
2031702 MLS ACTIVE Status
Excellent investment opportunity in Cross Plains and the very desirable Middleton-Cross Plains Area School District! This well-maintained eight-unit apartment building features all two-bedroom, one-bath units with a strong rental history and additional income from four coin-operated washers and four coin-operated dryers. Numerous unit improvements were completed in 2025 and 2026, including updated kitchens and bathrooms, LVP flooring, carpet, paint, trim, lighting, ceiling fans, appliances and blinds. Additional property improvements include foundation repairs with a transferable 20-year warranty, landscaping and regrading. Tucked back in an established area surrounded primarily by single-family homes, the property offers a desirable residential setting. Current rents offer potential upside, making this an attractive opportunity for investors seeking stable income with room for future growth.

2512 Valley St, Cross Plains

$550,000
4 Beds 2 Baths 2031496 MLS ACTIVE UNDER CONTRACT Status
Escape to your own private hideaway on 1.25 acres in the highly desirable Town of Middleton! Just minutes from downtown Middleton & Madison’s west side, this tranquil tri-level home is surrounded by conservancy green space, golden cornfields & a picturesque equestrian farm—delivering the ultimate peaceful retreat from city congestion while still being close to everything. Rich 5/8" hickory wood floors flow throughout the main level, leading you into a spacious kitchen designed to impress w/ SS apps, a large breakfast bar & a charming shiplap wall. With 4 bedrooms & 3 distinct living areas, everyone enjoys room to spread out & unwind. Step outside to the inviting patio w/ pergola, where sweeping views of the tree-lined grounds set the stage for late-summer BBQs & crisp fall campfires under the stars. A fully equipped 24×27 heated pole shed w/ dedicated sub-panel & 220-volt power stands ready for welders, heavy tools, or even an EV charger. The possibilities are endless at this property!

3425 Meadow Rd, Middleton

$849,900
2031478 MLS ACTIVE Status
Rare opportunity to own one of the few investment properties in the Town of Middleton on a large 1.2-acre lot! Enjoy breathtaking countryside views for miles from this exceptional duplex, professionally remodeled from top to bottom with quality finishes throughout. Each unit offers 3 bedrooms, 2 full bathrooms, spacious basement rec room, and additional versatile flex room, private laundry, attached 2-car garage. Each unit has a large concrete patio, great for enjoying the outdoors & sunset or sunrise views! Bonus features include a fenced in yard (4686) and a pergola (4688). Located in the highly rated Middleton-Cross Plains School District & the large lot size offers the possibility for potential additional development or building in the future. Potential for increased future rents to bring them up to market value! This turnkey property offers a great opportunity for investors or owner-occupants seeking rental income without sacrificing space, comfort, or location!

4686-4688 Capitol View Rd, Middleton

$825,000
4 Beds 3 Baths 2029049 MLS ACTIVE Status
Tucked in a beautiful wooded setting in Applewood Hills, this distinctive 4-bed, 2.5-bath home blends privacy, architectural character and thoughtful high-end updates. The light-filled main level showcases vaulted ceilings, exposed beams, wood floors and a dramatic floor-to-ceiling stone fireplace with built-in shelving. Expansive windows and patio doors bring the outdoors in and open to a spacious elevated deck overlooking the private, tree-lined yard. The updated kitchen features newer appliances, generous workspace and picturesque views. Major improvements include newer mechanicals, windows, and numerous quality updates throughout, offering comfort and peace of mind. Multiple living and dining spaces provide plenty of room to gather and entertain. Outside, enjoy mature trees, lush landscaping, a large lawn and fenced area creating a peaceful, park-like retreat. A truly unique Town of Middleton home with character, privacy and exceptional indoor-outdoor living!

7116 Applewood Dr, Middleton

$664,900
3 Beds 2 Baths 2031369 MLS ACTIVE Status
This Matali Builds ranch welcomes you through a covered entry & opens to a cathedral-ceiling great room where a gas fireplace with maple mantel & shiplap climbing to the vault steals the show. The kitchen shines with quartz counters, Amish-built cabinets, a full stainless appliance package & an island made for gathering. Split bedrooms give everyone breathing room, while the primary suite retreats to its own wing with a walk-in closet & tiled walk-in shower. A flex room, mudroom drop zone with built-in cubbies & main-floor laundry keep life running smoothly. Sip morning coffee on the covered back porch, then dream up plans for the exposed lower level with full-size windows, 8'+ ceilings & a bath already stubbed in. Tandem 3rd stall in the garage fits all the toys. Construction begins with an executed contract, so your selections still await! All this on nearly quarter acre lot with sought after Middleton-Cross Plains Schools, and easy access to stunning nature all around!

1419 Ridgetrail Dr, Cross Plains

$230,000
2031345 MLS ACTIVE UNDER CONTRACT Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH w/ full 8' walk-out exposure in lower level and is situated next to a retention pond.

10419 Golden Eagle Dr, Madison

$225,000
2031344 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH w/ full 8' walk-out exposure in lower level.

10423 Golden Eagle Dr, Madison

$225,000
2031342 MLS ACTIVE UNDER CONTRACT Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH w/ full 8' walk-out exposure in lower level.

10431 Golden Eagle Dr, Madison

$215,000
2031340 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH w/ possible 4' LL exp if home is elevated & steps added to garage - Buyer to verify w/ their builder if important.

10438 Red Pine Dr, Madison

$215,000
2031338 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH w/ possible 4' LL exp if home is elevated & steps added to garage - Buyer to verify w/ their builder if important.

10434 Red Pine Dr, Madison

$215,000
2031337 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH w/ possible 4' LL exp if home is elevated & steps added to garage - Buyer to verify w/ their builder if important.

10430 Red Pine Dr, Madison

$215,000
2031336 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH w/ possible 4' LL exp if home is elevated & steps added to garage - Buyer to verify w/ their builder if important.

10426 Red Pine Dr, Madison

$230,000
2031331 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, & the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 & find the perfect lot to build your dream home! Road construction to start in early Sept, w/ closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH w/ possible 4' LL exp if home is elevated & steps added to garage - Buyer to verify w/ their builder if important. It is situated next to retention pond.

10422 Red Pine Dr, Madison

$220,000
2031327 MLS ACTIVE UNDER CONTRACT Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH with a possible 4' lower level exposure if home is elevated & steps added to garage. Buyer to verify w/their builder if important. It backs to small continuation of the retention pond gully w/homes on the other side of the gully.

10425 Red Pine Dr, Madison

$220,000
2031326 MLS ACTIVE UNDER CONTRACT Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH with a possible 4' lower level exposure if home is elevated & steps added to garage. Buyer to verify w/their builder if important. It backs to small continuation of the retention pond gully w/homes on the other side of the gully.

10429 Red Pine Dr, Madison

$220,000
2031323 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH with a possible 4' lower level exposure if home is elevated & steps added to garage. Buyer to verify w/their builder if important. It backs to small continuation of the retention pond gully w/homes on the other side of the gully.

10433 Red Pine Dr, Madison

$220,000
2031322 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH with a possible 4' lower level exposure if home is elevated & steps added to garage. Buyer to verify with their builder if important.

10437 Red Pine Dr, Madison

$215,000
2031321 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH with no lower level exposure.

10436 Emerald Elm Rd, Madison

$215,000
2031319 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH with no lower level exposure. It backs to a small continuation of the retention pond gully with homes on the other side of the gully.

10432 Emerald Elm Rd, Madison

$215,000
2031317 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH with no lower level exposure. It backs to a small continuation of the retention pond gully with homes on the other side of the gully.

10428 Emerald Elm Rd, Madison

$215,000
2031316 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH with no lower level exposure. It backs to a small continuation of the retention pond gully with homes on the other side of the gully.

10424 Emerald Elm Rd, Madison

$215,000
2031315 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH with no lower level exposure. It backs to a small continuation of the retention pond gully with homes on the other side of the gully.

10420 Emerald Elm Rd, Madison

$230,000
2031314 MLS ACTIVE Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces SOUTH with no lower level exposure. It is situated next to a retention pond and backs to a small continuation of the retention pond gully with homes on the other side of the gully.

10416 Emerald Elm Rd, Madison

$215,000
2031312 MLS ACTIVE UNDER CONTRACT Status
Welcome to Westwind Phase 2! Located on Madison’s far west side within the Middleton school district, Westwind offers convenient access to the Beltline, Epic, major hospitals, shopping, dining, parks, walking paths, and the Pioneer Pointe pool. Phase 2 features 27 new homesites with city water and sewer, architectural covenants designed to maintain high-quality standards, and the flexibility to bring your own builder & build on your timeline. With 121 total lots planned across three phases, Westwind continues to grow. Explore Phase 2 and find the perfect lot to build your dream home! Road construction to start in early Sept, with closing dates anticipated to begin in early to mid-November—or sooner if roads are completed ahead of schedule. This lot faces NORTH with no lower level exposure. It will back to a future Westwind single family home phase.

10423 Emerald Elm Rd, Madison

This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. 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 perspective properties consumers may be interested in purchasing.