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4908 Winners Cir, Springfield
$3,300,000
7 Beds ⋅ 8 Baths ⋅ 2032111 MLS ⋅ 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 Cir, Springfield

5090 Aspen Valley Ct, Springfield
$2,750,000
5 Beds ⋅ 6 Baths ⋅ 2022993 MLS ⋅ 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 Ct, Springfield

7224 Kickaboo Rd, Springfield
$919,000
3 Beds ⋅ 3 Baths ⋅ 2033238 MLS ⋅ ACTIVE Status
Fall in love with your new, secluded country home, just minutes from Middleton. Custom built ranch home on 7.21 acres. 3-car garage (32x39) with floor heat. 4th garage in lower level (10x11) with garage door for all your toys. 9' walls on both levels, walk-in kitchen pantry, custom Amish cabinetry, solid wood interior doors, Andersen windows, 8' patio door, Thermo-zone floor heat exchange system. Rec room in lower level has stained, heated concrete floors and rough-in for shower in 1/2 bath, lots of storage, barrier free design elements, walking trails in woods, plenty of space for garden. This could be your retreat everyday! Driveway has recently been regraded. UHP Elite Home Warranty included. Never on the market before-one owner home.

7224 Kickaboo Rd, Springfield

7334 County Road K, Springfield
$779,900
4 Beds ⋅ 2 Baths ⋅ 2028002 MLS ⋅ ACTIVE Status
Rare opportunity to own a picturesque 2.09-acre country property in the desirable Town of Middleton, just minutes from Middleton and Madison. Offering the perfect blend of peaceful country living and city convenience, this unique property is filled with warmth, character, and endless potential. The beautifully landscaped grounds are the true centerpiece, featuring mature trees, colorful perennial gardens, a stunning established vineyard, an orchard, and expansive green space that creates a private, park-like retreat. A classic barn adds charm and versatility for hobbies, storage, or workshop space. Whether you dream of gardening, entertaining, or simply enjoying the beauty and privacy of nature, this property offers a setting that's difficult to find in today's market. Acreage properties in this sought-after location rarely become available—come experience the beauty, charm, and possibilities this special property has to offer.

7334 County Road K, Springfield

5220 Scenic Ridge Trl, Springfield
$759,900
3 Beds ⋅ 4 Baths ⋅ 2029209 MLS ⋅ ACTIVE Status
This Scenic Ridge Estates two story is meticulously maintained and offers a perfect balance of serene, scenic privacy and neighborhood living. Situated on a 1.07-acre lot, you have easy access to Middleton schools & numerous walking & biking trails, all while being just a short drive from the shops, restaurants, and conveniences of both Madison and Middleton. The main level features elegant updates, showcasing new flooring throughout, private home office, & spacious mudroom/laundry area. Family room is highlighted by a coffered ceiling, while the open-concept kitchen comes complete with a breakfast bar and transitions seamlessly into both formal and informal dining spaces. A screen porch opens directly out to the patio, ideal for outdoor enjoyment. Upstairs, you will find 3 comfortably sized bedrooms and 2 full baths, each featuring double vanities and bright skylights that fill the spaces with natural light. The finished lower level offers great entertaining space for adults and kids!

5220 Scenic Ridge Trl, Springfield

4862 Hickory Trl, Springfield
$745,000
5 Beds ⋅ 5 Baths ⋅ 2031233 MLS ⋅ ACTIVE Status
Tucked among the rolling hills of Enchanted Valley, this home sits on the most beautiful 1.28-acre lot, backing to the woods & offering majestic westward views of the Driftless Region. The main level is bright & open w/ a remodeled kitchen, spacious living room w/ double-sided gas fireplace which flows right to the sunroom w/ built-in bar & views to the backyard patio w/ hot tub. Also on the main level are 2 of 5 bedrooms, which could easily function as offices or a playroom. Upstairs is the primary suite with walk-in closet & attached bath with walk-in shower & laundry, plus 2 additional bedrooms. The lower level is a family room. There’s no lack of space for storage or hobbies w/ the unfinished portion of the basement, 3-stall extra-deep garage & storage shed in the yard. Other updates per seller in the last 10 years include furnace, AC, roof, siding, water softener, bathroom remodel, main level windows & well pump - see flyer for more. Plus lower town taxes & Middleton Schools!

4862 Hickory Trl, Springfield

4956 Enchanted Valley Rd, Springfield
$714,900
3 Beds ⋅ 3 Baths ⋅ 2030797 MLS ⋅ ACTIVE Status
Showings start Thursday, September 10th. Exceptionally maintained 3BR/2.5 BA home in the Town of Springfield, lovingly cared for by the same owners since it was built. Home is surrounded by lush landscaping, mature garden beds, and a beautifully manicured lawn. The open-concept main level features a kitchen updated in 2018 with custom Amish cabinetry, granite countertops, and eat-in dining space with sweeping views of the backyard. Open concept flow to main level living room. Down a few steps to the family room which offers a wood-burning fireplace, walkout to the patio, and half bath. UL includes 3 BR and 2 full BA, including a primary with private en-suite. Lowest level offers laundry, rec space, and storage. 3+ car garage includes a third bay with an oversized door. Additional separate heated shop space with access to backyard. You uniquely get the best of both worlds with living in peaceful retreat with quick access to surrounding communities!

4956 Enchanted Valley Rd, Springfield

N8687 3rd Ln, Springfield
$524,900
3 Beds ⋅ 1 Baths ⋅ 2028835 MLS ⋅ ACTIVE Status
PRICE IMPROVEMENT on this TURNKEY WATER FRONT property! Exceptional lakeside outdoor living, a completely renovated home, & approximately 70 feet of waterfront—a rare combination at this price. Set on peaceful School Section Lake, this move-in-ready 3-bedroom home was completely renovated inside & out, including an addition expanding living space & adding an oversized 2-car attached garage. Improvements include a brand-new metal roof, all-new windows, flooring, septic system, LP SmartSide siding, main-floor laundry, & more. The lakeside outdoor space features an expansive deck, custom pergola, fire pit, generous lawn, & plenty of room for entertaining & enjoying the water. Motorized boats are permitted; the lake is no-wake, ideal for boating, kayaking, paddleboarding, & fishing. Previously a successful short-term rental, this turnkey property offers proven rental history & potential future income use, subject to regulations—or enjoy it as your own year-round home or lake retreat.

N8687 3rd Ln, Springfield

7419 Riles Rd, Springfield
$500,000
4 Beds ⋅ 2 Baths ⋅ 2030121 MLS ⋅ ACTIVE Status
Enjoy the best of country living and privacy just minutes from Middleton at this spacious 4-bedroom, 2-bath raised ranch on 1.78 acres. The bright main level features hardwood floors, an inviting living room, dining area, and functional kitchen with pantry and ample natural light, and a full bathroom with a jetted tub. The finished lower level offers a walkout to the yard, full-size windows, a second kitchen, bonus room, and flexible living space—ideal for guests, hobbies, or additional living arrangements. The primary suite includes a walk-through bath with a walk-in shower. Outside, enjoy the expansive yard, patio, paved drive, and impressive 3-car detached garage. Conveniently located in the Middleton-Cross Plains School District with easy access to Middleton, Madison, and surrounding amenities. A rare opportunity to enjoy space, privacy, and convenience! Check out the 3D model!

7419 Riles Rd, Springfield

7766 Martinsville Rd, Springfield
$399,900
3 Beds ⋅ 2 Baths ⋅ 2033312 MLS ⋅ ACTIVE Status
Come see this rare Martinsville gem. Well-Maintained Ranch in the Middleton-Cross Plains Area School District. This home sits on a quiet, rural stretch of Martinsville with open views, just minutes from Cross Plains and Middleton. Everyday living is all on one level, with a main-floor primary bedroom and an attached garage. The functional, spacious eat-in kitchen features white oak cabinetry, tile backsplash and tile flooring, and the original hardwood floors provide warmth and character. The lower level is fully finished, with updated flooring, an updated full bathroom, an entertainment/movie room featuring a wet bar and refrigerator, an office nook, and a third bedroom with an egress window. This home has had many updates inside and out and has a functional spacious layout with storage in mind. Oustide is set within established landscaping and hardscaping and includes a large fenced garden, a garden shed and a fire pit.

7766 Martinsville Rd, Springfield

N8988 Deerborn Ave, Springfield
$379,000
3 Beds ⋅ 2 Baths ⋅ 2033193 MLS ⋅ ACTIVE Status
Showings to begin on Friday, 9/25. Escape to quiet living in this beautiful 3 bedroom, 2 bathroom log cabin home which was just restained in 2026! Warm & inviting, this home features gorgeous vaulted ceilings, stunning log beams, & a spacious kitchen with abundant cabinet space & a large island. Gather around the beautiful stone fireplace or light up the wood stove to stay cozy on those crisp days. A bonus room in the basement along with additional storage space allows room for your imagination! Enjoy your morning coffee from the front porch swing or wind down on the charming patio as the sun sets. A separate workshop, complete with a new metal roof in 2025, offers the ideal space for projects & tinkering. The impressive 43x53 Morton outbuilding features a 12 ft door, water, & electricity—perfect for hobbies, storage & all of your toys. This home is set on a private 1.18-acre lot with mature trees & landscaping & is just a short walk from peaceful, no-motor Lake Burnita! Welcome home!

N8988 Deerborn Ave, Springfield

N8600 5th Rd, Springfield
$265,000
4 Beds ⋅ 1 Baths ⋅ 2027027 MLS ⋅ ACTIVE Status
A FARMHOUSE RETREAT! Functional updates meet timeless charm on this scenic 2-acre property! This well-maintained 4-bedroom home features a spacious eat-in kitchen, main-level bedroom, and numerous updates including newer siding, windows, flooring, and mechanicals. Outside, you'll find a detached 2-car garage and multiple outbuildings, including a 30x40 pole barn, providing plenty of space for storage, hobbies, equipment, or recreational vehicles. Whether you're looking for a hobby farm, extra workspace, or a peaceful place to call home, this property offers the flexibility and functionality you've been searching for—all just minutes from Westfield. The seller is including all remaining personal property and belongings in the home and outbuildings with the sale, offering a unique opportunity for the next owner.

N8600 5th Rd, Springfield

8713 N 3rd Ct, Springfield
$247,000
3 Beds ⋅ 2 Baths ⋅ 2026531 MLS ⋅ ACTIVE Status
Escape to the peace and privacy of country living with this charming 3-bedroom, 2-bath home situated on 5 beautiful acres at the end of a quiet dead-end road. Surrounded by nature and offering plenty of room to roam, this property provides the perfect setting for those seeking space, serenity, and a slower pace of life. The home features a comfortable and functional layout with spacious living areas and well-sized bedrooms. Whether you're enjoying your morning coffee while taking in the peaceful surroundings or hosting family and friends, you'll appreciate the comfort and tranquility this property offers. Outside, you'll find multiple outbuildings providing abundant storage space for equipment, vehicles, recreational toys, hobbies, or workshop needs. There is plenty of room the the perfect garden. If you've been searching for a property that combines rural charm, usable acreage, and exceptional storage opportunities, this peaceful 5-acre homestead is one you won't want to miss.

8713 N 3rd Ct, Springfield

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