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$3,300,000
7 Beds ⋅ 5.5 Baths ⋅ ACTIVE Status
Executive home situated on 1.5 acres w/expansive views, offering luxury & craftsmanship. The main level showcases an impressive great room w/floor to ceiling stone fireplace. Gourmet chef?s kitchen with adjacent screen porch. Family room features a brick surround fireplace. Mud room, laundry & butler pantry on main level. Private owner?s suite featuring a spa-inspired bath, soaking tub, & custom closet. 4 additional bdrms, 2nd laundry & hidden paneled office complete the upper level. The spacious walk-out lower level is designed for recreation & entertaining. Complete w/a wet bar, theater rm, game area, indoor sport court, & gym. Outdoors, a private resort awaits with a sparkling pool, oversized patio, stunning pool house with fireplace, outdoor kitchen & grill. 4 car heated garage. Located in the highly desirable Middleton School District. This exceptional estate offers a rare combination of sophisticated living, superior craftsmanship, & resort-inspired amenities.

4908 Winners Circle, Springfield

Listing courtesy of Collective Real Estate Group.

$233,100
5 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status
Bring your vision to this spacious 5-bedroom, 1.5-bath two-story home packed with character and possibilities! The main level offers a living room, 1 bedroom, main-floor laundry, workshop, 3-season room, and a unique former bar area ready to become an impressive rec room or entertaining space. Upstairs offers 4 bedrooms, Family Room and Den. Outside, enjoy two concrete patios, a detached 1-car garage, and an in-ground pool that has not been used since 2008. With generous space and a flexible layout, this property offers plenty of opportunity to make it your own. Home needs repairs and updates and may not qualify for FHA or other government-backed financing. Property and pool are being sold in their current condition. He had a license to open as a bar, but had a stroke before he finished it

13 W Main Street, Deerfield

Listing courtesy of Realty Executives Platinum.

$799,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status
VRP $799,900-$849,900. Tucked into Richmond Hill on a spacious .52-acre cul-de-sac lot, welcome to this private backyard retreat. This 3 bedroom, 2 bath ranch offers nearly 2,600 sq. ft. of finished living space all on one level. Vaulted ceilings, expansive windows, hardwood flooring, and a striking stone fireplace create an impressive space filled with natural light. The kitchen opens to the dining area and incredible sunroom, featuring walls of windows, powered skylights and a freestanding stove. Outside, this property separates itself. The fenced backyard with walls of trees feels like your own private retreat with a heated saltwater in-ground pool, patio, mature landscaping, 17-zone irrigation. Add. highlights include a 3-car garage, 2023 sump pump, and new roof. A home that can't be built for this price.

10 Vienna Circle, Madison

Listing courtesy of EXP Realty, LLC.

$499,900
5 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Welcome to the back Yard Oasis! This 5 bedroom, 2.5 baths home has new flooring on upper level throughout. New furnace and all new ductwork. Seamless siding. New windows in 2000. Great kitchen with all appliances. Now lets get to the back yard. Enjoy a 36x16.5 a pool with a beautiful new pool house with large screen tv included. Enjoy the gas heat from the garage furnace on those chilly nights. Also, the home has NEST cameras that you can watch, talk and night vision from your phone. Fireplace was inspected and cleaned and then never used. Hurry this house is going to move fast being in Stoughton!

908 Roby Road, Stoughton

Listing courtesy of Century 21 Affiliated.

$1,175,000
5 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
Experience luxury living w/this custom-built home, offering 5,000+ sqft of beautifully crafted living space in a 1.5-acre park-like setting just 20 min from Madison. Precisely landscaped grounds, supported by a new well pump installed for the sprinkler system, & a maintenance-free wraparound deck frame a beautiful 16'x34' in-ground swimming pool, creating a private backyard retreat for relaxing & making memories. Large windows flood the home w/natural light.Cherry hardwood floors cover the main & upper levels. High ceilings, transom windows, solid-core maple doors & trim & 3 fireplaces create an inviting atmosphere.The gourmet kitchen features cherry cabinetry & Italian granite countertops. The formal dining room, private library/office, spacious family rooms & a walk-out lower level offer flexibility for everyday living & entertaining. The 3-zoned HVAC, instant hot water, finished garage, full brick facade w/"coined corners", exterior lighting, & fencing complete this remarkable home.

7341 Lone Cedar Court, Roxbury

Listing courtesy of Bunbury & Assoc, REALTORS.

$725,000
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Making its debut on the market after being lovingly cherished by two generations of the same family, this iconic mid-century estate is one of Sun Prairie's true hidden gems. Tucked away on a breathtaking, privately gated 1.5-acre wooded lot in the heart of the city, this timeless residence perfectly blends classic architectural charm with thoughtful modern updates. Featuring 4 bedrooms + 3.5 baths, private den, rec room, game room + an expansive 3-season porch overlooking the 20 x 40' in-ground saltwater pool. Nestled on a fully gated, wooded 1.5-acre lot, you'll enjoy the convenience of city living with the privacy and serenity of your own personal retreat. Major updates include a remodeled kitchen, roof, furnaces, windows, pool heater, and much more. More than a home?this is a legacy estate where timeless design meets modern comfort.

713 N Bird Street, Sun Prairie

Listing courtesy of Sprinkman Real Estate.

$3,895,000
5 Beds ⋅ 5.5 Baths ⋅ ACTIVE Status
Hart DeNoble Masterpiece on 14.97 acres-Middleton Schools. This property really has it all, & feels like you're living in the middle of a gorgeous park setting. Walking/Riding trails through the prairie grasses, & trail ride through the wooded area as well. An abundance of privacy, spectacular views, & endless spaces. 4 car attached heated garage, 4 car detached heated garage w/pool house full bath/lockers. Heated Barn/outbuilding w/basketball/pickleball court, locker room type full bath w/2 showers &, 2 heated parking spaces, & finished bonus room above it all overlooking the beautiful prairie & woods views, & also overlooking Basketball/Pickleball court. In ground Saltwater pool, new hot tub. Gorgeous home, each bedrm is full ensuite w/in floor heat in baths, 4 up, 1 down. Elevator in home. Primary bdrm has 4 season porch off of it, w/gas FP, & provides breathtaking views. 4 Gas FP's. Too many features to list! ***Please do NOT drive down driveway without a confirmed showing.***

7876 Autumn Pond Trail, Springfield

Listing courtesy of Bunbury & Assoc, REALTORS.

$2,875,000
6 Beds ⋅ 5.5 Baths ⋅ ACTIVE Status
Tucked away on a quiet cul-de-sac in the gated Community of Bishops Bay, this exceptional home offers a private, resort-like setting you'll never want to leave. Surrounded by mature trees, backing to fairway 11 on Bishops Bay Country Club, enjoy breathtaking sunset views & year-round serenity from your own backyard retreat. Spend summer days relaxing by the pool, entertaining on the patio, or unwinding in the 3-season room. Inside, the chef's kitchen is designed for gathering, featuring premium Wolf Sub Zero & Cove appliances, oversized island, & beautiful custom finishes. Walls of Marvin windows capture the stunning views & fill the home with natural light. The versatile indoor sport court offers endless possibilities. With flexible living areas, luxurious craftsmanship, up to 7 bedrooms w/2 first floor primary suites. See MLS feature sheet - custom woodwork, white oak flooring, whole home speakers, heated & epoxy garage, smart lighting, permanent holiday lights, irrigation & more.

4937 Championship Circle, Westport

Listing courtesy of Pinnacle Real Estate Group LLC.

$1,299,900
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Welcome to this stunning custom-built home! The open-concept main level showcases soaring ceilings, abundant natural light, and a beautiful stone fireplace that anchors the great room. The kitchen is designed to impress with custom cabinetry, a large center island, double ovens, gas cooktop, walk-in pantry, and stylish wine bar. A private office with built-ins, mudroom with custom lockers, and convenient drop zone add both function and flexibility. The primary offers a spa-like retreat with a walk-in tile shower, dual vanities, and oversized walk-in closet. Upstairs features three additional bedrooms and a full bath, while the finished lower level provides a large game room, exercise room, full bath, and ample storage. Enjoy outdoor living from the screened porch, expansive deck, and dedicated grill deck and in-ground pool! An oversized 4-car garage completes this exceptional home, offering the perfect blend of craftsmanship, luxury finishes, and everyday comfort.

5833 Grassland Terrace, Sun Prairie

Listing courtesy of MHB Real Estate.

$799,999
3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
New Price! Waunakee Schools with Middleton Convenience! Tucked away on a quiet cul-de-sac in highly sought-after Fox Bluff, this beautiful home offers privacy, space, and an unbeatable location. Surrounded by mature trees and tons of green space, the property sits on a huge lot just outside of town. Residents of the Town of Westport enjoy notably lower property taxes while benefiting from an A+ location just minutes from Waunakee, Middleton, and Madison. The backyard is built for entertaining, featuring a huge underground pool with a spacious deck, fire pit area, and large yard. The home's best room is the sunroom overlooking the backyard and surrounding green space. Currently used as a home office and billiards room, this flex space is versatile. Complete with 3 garage stalls, the home includes a rear third stall perfect for a boat, ATV, riding mower, or other equipment you'd like to store separately from your vehicles. With a little TLC this home can be taken to the next level!

3924 S Meadow Drive, Westport

Listing courtesy of Bruner Realty & Management.

$639,900
4 Beds ⋅ 2 Baths ⋅ 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 Street, Middleton

Listing courtesy of Shore Bluff Realty.

$550,000
4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
EXTEND SUMMER WITH YOUR OWN POOL! Presenting this classic well maintained colonial in the popular west end of Greentree Neighborhood Association with a gorgeous inground pool!Lots of living space with 4 bedrooms all upstairs, while the first floor offers two living spaces: A large living room with brand new carpeting and a cozy family room at the opposite end with hardwood floors and a wood burning fireplace.In between you?ll enjoy the huge kitchen with granite counters, updated appliances with a work area and large formal dining room. The lower level offers a large rec room, private den and tons of storage including a large workshop area. The hidden gem is the inground pool which is like your own private oasis. There's a new solar cover, pool motor, cleaning system, alarm and liner all since 2019 so relax and enjoy.Recent updates provide the peace of mind that you are purchasing a home that has been extremely well cared for by the last two owners.

6602 Montclair Lane, Madison

Listing courtesy of First Weber Inc.

$1,990,000
5 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
Wake up to sweeping, unobstructed views stretching all the way to Blue Mounds. This extraordinary stand alone single family home condominium delivers a lifestyle that's nearly impossible to replicate. Entertain in style with a saltwater pool, a covered outdoor kitchen, and a firepit perfectly positioned for those breathtaking sunset views. Inside, soaring ceilings with exposed beams, a chef's kitchen, a theatre room, and a luxurious primary suite with heated floors, jetted tub, and spa shower set an exceptional tone throughout. A fully self-contained 1 Bedroom/1 bath apartment offers rare multigenerational flexibility ? complete with heated floors throughout, a sunroom, private patio, gas fireplace, vaulted ceilings, built-in breakfast nook, walk-in pantry, and its own mechanicals. Whether for aging parents, adult children, or guests, it delivers total privacy without leaving the property. Some homes are just houses. This one is a life upgrade.

7606 Driftless Ridge Way, Verona

Listing courtesy of EXP Realty, LLC.

$2,750,000
5 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
Set on a quiet cul-de-sac in Autumn Pond, with nearly three wooded acres of Enchanted Valley countryside ? this is the kind of house that's already done the hosting prep for you. The pool's in. The hot tub's heated. The fire pit's waiting. A screen porch and a four-season room with a wood-burning fireplace both open onto the trees.The kitchen is built for the cook with a full table: Wolf, double ovens, Sub-Zero, wine fridge, and a back pantry with storage beyond belief. Two laundry rooms, an EV charger, and a solar battery handle the unsexy stuff. Autumn Pond brings its own hiking trails and a private pond, year-round. The wildlife shows up on its own. Timeless, unfussy, and entirely ready to live in. NEW roof, pool liner and pool cover summer 2026.

5090 Aspen Valley Court, Springfield

Listing courtesy of @properties-elleven Christie's International.

$3,750,000
4 Beds ⋅ 4.5 Baths ⋅ ACTIVE 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 Road, Middleton

Listing courtesy of First Weber Inc.

$573,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Dreaming of peaceful country living with room to spread out? Nestled on 2 scenic acres, this well-maintained 3-bedroom, 3-bath bi-level home offers the perfect blend of comfort, function, and outdoor enjoyment. Step outside & fall in love with the incredible in-ground pool, surrounded by lush perennials & a spacious composite deck?an ideal setting for summer entertaining. Inside features a versatile layout with a welcoming LL family room complete with a wet bar. You?ll also find a large flex room with a sauna, a convenient laundry area w/an additional bath. The primary suite offers a spa-like atmosphere and private patio doors leading directly to the pool area?your own personal escape. Car enthusiasts, hobbyists, or anyone needing extra space will appreciate the impressive 30x72 heated shop, equipped w/100-amp electrical service. spacious 2-car attached garage rounds out this property. Enjoy the freedom of country living while still having all the amenities you need.

2934 County Rd W, Christiana

Listing courtesy of Stark Company, REALTORS.

Copyright 2026 WIREX Multiple Listing Service. 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 prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.

Copyright 2026 WIREX Multiple Listing Service. 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 prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.