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2880 Siggelkow Road, Cottage Grove
$1,200,000
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
1st show OH 10/29 @ 5pm. Designed around breathtaking backyard sunsets, this custom ranch offers privacy & thoughtful design on 2.5 acres, minutes from the Beltline & interstate. A backyard oasis features a heated saltwater pool w/auto cover, firepit, hot tub hookup, in-ground trampoline & established landscaping that makes this home better than new. Enjoy the views from the 3-season porch w/vinyl windows & gas fireplace. Inside, a brilliant split-bedroom layout offers 4 spacious main-floor bedrooms, including a luxurious primary suite w/dedicated laundry & pocket office. The secondary wing offers 2 full baths & a second laundry area. Custom conveniences include an oversized walk-in pantry w/appliance garage & garage access, dog-washing station & premium lighting. A 532 SF finished bonus room adds recreation space, while the 2,000+ SF unfinished basement features 9' ceilings, future bath plumbing, full windows & garage access. The best of both worlds: rural serenity, city convenience!

2880 Siggelkow Road, Cottage Grove

Listing courtesy of Real Broker LLC.

3029 Bosshard Drive, Fitchburg
$975,000
5 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Value range priced $975,000 - $1,075,000. Enjoy sunny days and poolside gatherings at this private, serene 5BR/4BA executive Colonial in Seminole Hills Estates. Bright, open living spaces include a vaulted great room with gas fireplace, formal + informal dining, and a Cook?s kitchen w/ brkfst bar, granite, pantry + gas range w/ downdraft hood. French glass doors open to a versatile den, office or music rm. Upstairs, retreat to the oversized-vaulted owners BR + ensuite w/ a Pearl spa tub, double sinks, sit-down vanity, walk-in shower + two separate closet areas. Three guest bedrooms + a tub/shower BA complete the upper level. The daylight exposed lower-level offers a fifth BR, full shower BA, rec room with gas fireplace, bright office/workout/hobby room and ample storage. Outside, retreat + rumpus in the fenced 1/3-acre yard with in-ground pool, rear deck, Rainbow play system and garden beds. Three-level zone HVAC adds comfort. Friendly neighborhood + demand Verona Schools!

3029 Bosshard Drive, Fitchburg

Listing courtesy of Coldwell Banker Real Estate Group.

7842 Big Timber Trail, Middleton
$939,000
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Custom home in a beautiful setting, Enchanted Valley Estates and Middleton-Cross Plains schools. Live with the convenience of a subdivision on a cul-de-sac but in privacy of the nature. More than 4,000 sq ft provides not only personal space, whether it need be for work or play, but warm gathering areas to share life. Newly refinished floors in kitchen and entry. Formal dining room with bar. Great room with gas fireplace, parquet floors and picture window views across the pool to the valley. Additional Great Room with wood-burning fireplace and windows overlooking the forest. Hot Tub room with fireplace. Built in cabinets throughout the home. Multiple decks. Walk-out lower level to pool in-ground pool. House and decks are newly painted. 4.5 car garage. Lower bedroom is equipped as an efficiency if desired as such. Acreage and Tax information is for both parcels 0708-062-0067-7 and 0708-062-0850-8. Buyer to verify s.f. and room dimensions if important. No sign on property.

7842 Big Timber Trail, Middleton

Listing courtesy of Heartland Business Transitions, Inc.

5766 Derby Downs Drive, Westport
$1,375,000
5 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Skip the wait, the mud, and the ?ready by spring.? Settle in and enjoy a beautiful home by the holidays. Built in 2021 and still like new, this custom home sits on almost 1/2 acre with mature landscaping already grown in. Imagine coffee on the three-season porch, the gas fireplace glowing, music drifting from built-in speakers, and the heated saltwater pool just beyond and ordinary Tuesdays start to feel like vacation. Nothing here is builder grade: hickory floors, transom beam windows, solid wood trim with deep 4" window stools, a GE Monogram 6-burner gas range, and three gas fireplaces with remote start. A primary suite with a luxurious ensuite plus 4 more bedrooms linked by Jack and Jill baths, an office, and a finished basement with even more space to expand, a Container Store pantry and whole-house humidifier round it out. The garage has a deep third bay and a heater-ready gas line. The upgrades are done. The yard is grown. The only thing missing is you.

5766 Derby Downs Drive, Westport

Listing courtesy of EXP Realty, LLC.

930 Winding Way, Madison
$1,075,000
4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Welcome to an exceptional home in the highly sought after Blackhawk neighborhood! You'll love meal prep again in the expansive gourmet kitchen equipped with premium Sub-Zero and Wolf appliances, granite throughout, and a convenient walk-in pantry. A large screened-in porch is a perfect place for morning coffee, and offers an inviting extension of the living space, connecting you to the private tastefully landscaped backyard complete with pool and an in-ground sprinkler system. The spacious main-level primary suite offers dual walk-in closets and a luxurious bath with separate shower and jetted tub. An elegant office with custom built-ins, formal dining room and welcoming great room complete the main level. The lower level continues to impress with high ceilings and a spacious, light-filled family room featuring a cozy fireplace and a huge bar area! Three additional bedrooms, with adjoining bathrooms, provide comfort and privacy for family or guests.

930 Winding Way, Madison

Listing courtesy of Compass Real Estate Wisconsin.

908 Roby Road, Stoughton
$489,000
5 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Looking for a 5-bedroom home with a 3-car garage that won't cost an arm and a leg? Welcome home to this well-cared-for and updated home in the heart of Stoughton! On the exterior, you are well protected with seamless steel siding, premium gutter protection, and a heated 3-car garage. As you enter, you notice the welcoming open concept and large living room, which flows into the kitchen complete with a gas or charcoal indoor grill. The home has been updated with new HVAC ducting and a new furnace and AC in 2021. A newly constructed heated pool house with Nichiha premium composite siding and pergola completes the backyard living and entertaining area and adds a great place to relax between swims or watching the kids play in the pool. The large lower-level family room gives even more options for entertaining or relaxing by the wood-burning fireplace!

908 Roby Road, Stoughton

Listing courtesy of Rock Realty.

3111 Katie Ida Lane, Bristol
$1,099,955
5 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status
Discover an extraordinary private retreat where luxury and resort-style living with an INCREDIBLE POOL come together in Bristol. Set on nearly three quarters of an acre, this impressive five bedroom, three and one-half bathroom estate offers approximately 4,074 square feet of refined living space designed for unforgettable entertaining and effortless everyday living. A spectacular private pool anchors the outdoor experience, while expansive gathering spaces, a four-car garage, finished lower level, recreation room, elegant bar and private fitness area elevate the lifestyle. From sophisticated interiors to exceptional outdoor amenities, every detail creates a rare opportunity to live, entertain and escape without ever leaving home.

3111 Katie Ida Lane, Bristol

Listing courtesy of Shorewest Realtors, Inc..

4908 Winners Circle, Springfield
$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.

13 W Main Street, Deerfield
$224,900
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.

7341 Lone Cedar Court, Roxbury
$1,080,000
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.

713 N Bird Street, Sun Prairie
$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.

3924 S Meadow Drive, Westport
$739,999
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.

1308 Shirley Street, Middleton
$599,900
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.

7606 Driftless Ridge Way, Verona
$1,895,000
5 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
Wake up to sweeping, unobstructed views stretching all the way to Blue Mounds. This extraordinary single family home 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. Seller offering credit for interest rate buydown!

7606 Driftless Ridge Way, Verona

Listing courtesy of EXP Realty, LLC.

5090 Aspen Valley Court, Springfield
$2,750,000
5 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status
Middleton Schools! 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.

2934 County Rd W, Christiana
$500,000
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.

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