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Welcome home to this custom-built Cherrywood home offering 4,391 square feet of finished living space and room to gather, unwind, and make it your own. A lovely home with recent improvements; including a new roof, new siding, & new appliances to name a few - added confidence as you consider your next move. The spacious, traditional floor plan features a formal dining room and a separate sitting room, with large windows bringing beautiful natural light into both spaces. In the great room, custom built-ins and a cozy fireplace create an inviting place to relax, while the adjoining sunroom offers tiled floors and a bright setting to enjoy throughout the day. Upstairs, the generously sized primary suite provides a comfortable retreat. Also, the basement space offers possibilities for a future recreation room, workout area, or home theater. Outside, enjoy a large backyard with space to entertain, garden, or simply relax. A three-car attached garage is an added bonus!

4 Beds ⋅ 3 Baths ⋅ 2035130 MLS ⋅ ACTIVE Status

Welcome home to this custom-built Cherrywood home offering 4,391 square feet of finished living space and room to gather, unwind, and make it your own. A lovely home with recent improvements; including a new roof, new siding, & new appliances to name a few - added confidence as you consider your next move. The spacious, traditional floor plan features a formal dining room and a separate sitting room, with large windows bringing beautiful natural light into both spaces. In the great room, custom built-ins and a cozy fireplace create an inviting place to relax, while the adjoining sunroom offers tiled floors and a bright setting to enjoy throughout the day. Upstairs, the generously sized primary suite provides a comfortable retreat. Also, the basement space offers possibilities for a future recreation room, workout area, or home theater. Outside, enjoy a large backyard with space to entertain, garden, or simply relax. A three-car attached garage is an added bonus!

7746 Maas Dr, Middleton

$939,000

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.

4 Beds ⋅ 4 Baths ⋅ 2034964 MLS ⋅ 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 Trl, Middleton

$1,499,000

Experience this elevated, move-in ready home in Middleton. The main level is anchored by two first-floor bedroom suites and a seamless connection between kitchen, dining, and den, with hardwood floors, a wood-burning fireplace, and SubZero, Wolf, and Cove appliances. All bedrooms in the main home feature en suite baths, offering comfort and privacy throughout. Above the garage, a separately accessed 1 bed, 1 bath apartment provides unique flexibility for multigenerational living, guests, extended stays, or a private workspace. Solar, geothermal heating and cooling, and a metal roof offer long-term energy efficiency and resiliency. HOA-managed landscaping and snow removal support a true lock-and-leave lifestyle.

5 Beds ⋅ 6 Baths ⋅ 2034688 MLS ⋅ ACTIVE Status

Experience this elevated, move-in ready home in Middleton. The main level is anchored by two first-floor bedroom suites and a seamless connection between kitchen, dining, and den, with hardwood floors, a wood-burning fireplace, and SubZero, Wolf, and Cove appliances. All bedrooms in the main home feature en suite baths, offering comfort and privacy throughout. Above the garage, a separately accessed 1 bed, 1 bath apartment provides unique flexibility for multigenerational living, guests, extended stays, or a private workspace. Solar, geothermal heating and cooling, and a metal roof offer long-term energy efficiency and resiliency. HOA-managed landscaping and snow removal support a true lock-and-leave lifestyle.

4029 Serenbe St, Middleton

$315,000

Premium cul-de-sac homesite in Middleton-Cross Plains schools! This 0.92-acre lot at the end of Bellvine Ct borders a mature evergreen tree line and offers curved frontage that gives you room to design, with walkout potential. Soil evaluation completed for private septic; private well required. Enjoy a quiet, no-through-traffic setting just across Mineral Point Rd from Pioneer Pointe’s golf, dining, and amenities, with established Spruce Hollow homes at the entrance and quick access to Middleton’s growing west side. Bring your own builder.

2034344 MLS ⋅ ACTIVE Status

Premium cul-de-sac homesite in Middleton-Cross Plains schools! This 0.92-acre lot at the end of Bellvine Ct borders a mature evergreen tree line and offers curved frontage that gives you room to design, with walkout potential. Soil evaluation completed for private septic; private well required. Enjoy a quiet, no-through-traffic setting just across Mineral Point Rd from Pioneer Pointe’s golf, dining, and amenities, with established Spruce Hollow homes at the entrance and quick access to Middleton’s growing west side. Bring your own builder.

Lot 1 Bellvine, Middleton

$1,599,000

Custom-built home on 1.66 acres in the Town of Middleton, tucked at the end of a quiet cul-de-sac surrounded by trees and nature. Hardwood floors flow through the main level with a generous kitchen and walk-in pantry, living room with gas fireplace and tray ceiling lighting, main-floor laundry, and spacious primary suite with walk-in shower and corner tub. Two bonus rooms offer flexible office or library space. Upstairs features 3 bedrooms and a lofted living area. The guest room has a full en suite bath, while the other 2 bedrooms connect through a Jack-and-Jill 3/4 bath with separate sinks and each has a walk-in closet. The finished lower level features a theater room, rec/family room with wet bar, exercise room, sauna, and hot tub. Attached 3-car garage includes basement access. A huge detached, insulated and partially heated garage/shop offers exceptional project and storage space. Enjoy the back patio, gazebo, and fire pit near the Ice Age National Scenic Trail. A must-see!

4 Beds ⋅ 5 Baths ⋅ 2032474 MLS ⋅ ACTIVE Status

Custom-built home on 1.66 acres in the Town of Middleton, tucked at the end of a quiet cul-de-sac surrounded by trees and nature. Hardwood floors flow through the main level with a generous kitchen and walk-in pantry, living room with gas fireplace and tray ceiling lighting, main-floor laundry, and spacious primary suite with walk-in shower and corner tub. Two bonus rooms offer flexible office or library space. Upstairs features 3 bedrooms and a lofted living area. The guest room has a full en suite bath, while the other 2 bedrooms connect through a Jack-and-Jill 3/4 bath with separate sinks and each has a walk-in closet. The finished lower level features a theater room, rec/family room with wet bar, exercise room, sauna, and hot tub. Attached 3-car garage includes basement access. A huge detached, insulated and partially heated garage/shop offers exceptional project and storage space. Enjoy the back patio, gazebo, and fire pit near the Ice Age National Scenic Trail. A must-see!

7901 Windermere Ct, Middleton

$470,000

Move right into this beautiful 3 bedroom home conveniently located on Middleton's NE side. Home has had numerous updates over the last 7 years including furnace/AC, siding, windows, roof and remodeled kitchen. Spacious living room with gas fireplace conversion and LVP flooring. Enjoy the weather, but not the bugs in your screened-in porch. Fenced backyard includes a small brick patio area and a storage shed. Centrally located with easy access to East Madison, Waunakee, plenty of shopping and dining, Lake Mendota and Pheasant Branch Conservancy.

3 Beds ⋅ 2 Baths ⋅ 2031392 MLS ⋅ ACTIVE UNDER CONTRACT Status

Move right into this beautiful 3 bedroom home conveniently located on Middleton's NE side. Home has had numerous updates over the last 7 years including furnace/AC, siding, windows, roof and remodeled kitchen. Spacious living room with gas fireplace conversion and LVP flooring. Enjoy the weather, but not the bugs in your screened-in porch. Fenced backyard includes a small brick patio area and a storage shed. Centrally located with easy access to East Madison, Waunakee, plenty of shopping and dining, Lake Mendota and Pheasant Branch Conservancy.

5713 Highland Way, Middleton

$775,000

Welcome to this classic two-story Colonial in the desirable Cherrywood neighborhood! Nestled on a beautiful wooded lot, you'll enjoy peaceful country living with the convenience of nearby shopping, dining, and amenities. Take quiet walks, relax on the deck, and enjoy the deer, birds, and other wildlife right in your own backyard. The main level offers a spacious family room with a fireplace, formal living room with a second fireplace, formal dining room, and a private study, perfect for working from home. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite with a private sitting area and large ensuite bath. The walk-out lower level provides additional living space and endless possibilities for future finishing or recreation. Home is being sold AS-IS

4 Beds ⋅ 4 Baths ⋅ 2031218 MLS ⋅ ACTIVE Status

Welcome to this classic two-story Colonial in the desirable Cherrywood neighborhood! Nestled on a beautiful wooded lot, you'll enjoy peaceful country living with the convenience of nearby shopping, dining, and amenities. Take quiet walks, relax on the deck, and enjoy the deer, birds, and other wildlife right in your own backyard. The main level offers a spacious family room with a fireplace, formal living room with a second fireplace, formal dining room, and a private study, perfect for working from home. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite with a private sitting area and large ensuite bath. The walk-out lower level provides additional living space and endless possibilities for future finishing or recreation. Home is being sold AS-IS

3534 Swoboda Rd, Middleton

$300,000

Your Dream Home Starts Here! Imagine building a home designed around the way you live, the way you entertain, & what matters most to you. This beautiful 1.24-acre homesite in the Town of Middleton gives you the space and flexibility to bring that vision to life. Enjoy a peaceful, family-friendly setting with excellent schools, while being conveniently located near walking & biking trails, restaurants, shopping, golf courses, & everyday amenities. Bring your own builder & create a home that is uniquely yours from the floor plan & finishes to the outdoor spaces where you’ll make memories for years to come. Located adjacent to Spruce Hollow this homesite offers a beautiful setting to build the home you’ve been envisioning. Your Vision. Your Builder. Your Home.

2031000 MLS ⋅ ACTIVE Status

Your Dream Home Starts Here! Imagine building a home designed around the way you live, the way you entertain, & what matters most to you. This beautiful 1.24-acre homesite in the Town of Middleton gives you the space and flexibility to bring that vision to life. Enjoy a peaceful, family-friendly setting with excellent schools, while being conveniently located near walking & biking trails, restaurants, shopping, golf courses, & everyday amenities. Bring your own builder & create a home that is uniquely yours from the floor plan & finishes to the outdoor spaces where you’ll make memories for years to come. Located adjacent to Spruce Hollow this homesite offers a beautiful setting to build the home you’ve been envisioning. Your Vision. Your Builder. Your Home.

Lot 3 Bellvine, Middleton

$800,000

Timeless Style, Exceptional Space, Endless Possibilities! Set on a quiet cul-de-sac, this single-family house offers the space and features that make home feel special. This classic two-story Colonial boasts 4 bedrooms, 2.5 bathrooms and an impressive 3,168 sq. ft. The kitchen is ready for everything from weeknight dinners to holiday gatherings with a center island and double oven. Two wood-burning fireplaces create cozy gathering spaces, while the four-season room offers a relaxing retreat throughout the year. The primary bedroom features a full en suite. Main-floor laundry keeps daily routines convenient, and the attached 2-car garage provides additional storage and functionality. Wet bar plumbing set up in the basement. Classic character, generous living space and an inviting setting come together beautifully!

4 Beds ⋅ 3 Baths ⋅ 2029034 MLS ⋅ ACTIVE UNDER CONTRACT Status

Timeless Style, Exceptional Space, Endless Possibilities! Set on a quiet cul-de-sac, this single-family house offers the space and features that make home feel special. This classic two-story Colonial boasts 4 bedrooms, 2.5 bathrooms and an impressive 3,168 sq. ft. The kitchen is ready for everything from weeknight dinners to holiday gatherings with a center island and double oven. Two wood-burning fireplaces create cozy gathering spaces, while the four-season room offers a relaxing retreat throughout the year. The primary bedroom features a full en suite. Main-floor laundry keeps daily routines convenient, and the attached 2-car garage provides additional storage and functionality. Wet bar plumbing set up in the basement. Classic character, generous living space and an inviting setting come together beautifully!

1619 Elderwood Cir, Middleton

$510,000

Welcome home to this beautifully maintained two story Colonial, nestled on a quiet cul-de-sac in one of Middleton’s most sought-after neighborhoods. This inviting home blends comfort, functionality, and timeless charm, with generous living spaces ideal for everyday living and entertaining. Enjoy brand-new kitchen appliances, fresh paint throughout, and new carpeting on the second level living quarters and finished lower-level basement. Outside, the beautifully landscaped yard features mature trees, vibrant gardens, and an impressive stone retaining wall, creating exceptional curb appeal and a peaceful backyard retreat. With no sidewalk to maintain, you can also enjoy one less winter chore by not shoveling sidewalks! Located within walking distance of Northside Elementary School and just minutes from Pheasant Branch Conservancy, this home offers convenient access to scenic trails, shopping, and everyday amenities.

3 Beds ⋅ 4 Baths ⋅ 2030056 MLS ⋅ ACTIVE Status

Welcome home to this beautifully maintained two story Colonial, nestled on a quiet cul-de-sac in one of Middleton’s most sought-after neighborhoods. This inviting home blends comfort, functionality, and timeless charm, with generous living spaces ideal for everyday living and entertaining. Enjoy brand-new kitchen appliances, fresh paint throughout, and new carpeting on the second level living quarters and finished lower-level basement. Outside, the beautifully landscaped yard features mature trees, vibrant gardens, and an impressive stone retaining wall, creating exceptional curb appeal and a peaceful backyard retreat. With no sidewalk to maintain, you can also enjoy one less winter chore by not shoveling sidewalks! Located within walking distance of Northside Elementary School and just minutes from Pheasant Branch Conservancy, this home offers convenient access to scenic trails, shopping, and everyday amenities.

3702 Spring Hill Ct, Middleton

$724,900

Spacious, updated ranch-style condo in Bishop's Bay with a main-level primary suite and a new roof. The open-concept kitchen and living room feature bamboo flooring and a gas fireplace, while the eat-in kitchen offers solid surface counters, a gas range with hood vent, and abundant storage. Step outside to the private, covered composite deck — perfect for grilling or fresh air. The large primary suite impresses with custom built-ins, a walk-in shower, jetted tub, and an oversized walk-in closet. Downstairs, brand-new carpet runs throughout the expansive walk-out living space, complete with a second gas fireplace and a concrete patio. Two additional bedrooms, a full bath, and a private office round out the lower level. Recent updates include a new furnace, A/C, and water heater ('23) and new lower-level flooring('26). Topping it all off is a rare, oversized 4 car garage — plenty of room for cars, boats, and all your toys. There's simply too much to list — schedule your showing

3 Beds ⋅ 3 Baths ⋅ 2029323 MLS ⋅ ACTIVE Status

Spacious, updated ranch-style condo in Bishop's Bay with a main-level primary suite and a new roof. The open-concept kitchen and living room feature bamboo flooring and a gas fireplace, while the eat-in kitchen offers solid surface counters, a gas range with hood vent, and abundant storage. Step outside to the private, covered composite deck — perfect for grilling or fresh air. The large primary suite impresses with custom built-ins, a walk-in shower, jetted tub, and an oversized walk-in closet. Downstairs, brand-new carpet runs throughout the expansive walk-out living space, complete with a second gas fireplace and a concrete patio. Two additional bedrooms, a full bath, and a private office round out the lower level. Recent updates include a new furnace, A/C, and water heater ('23) and new lower-level flooring('26). Topping it all off is a rare, oversized 4 car garage — plenty of room for cars, boats, and all your toys. There's simply too much to list — schedule your showing

5021 Prairie Rose Ct, Middleton

$575,000

Enjoy peaceful living on a quiet cul-de-sac set on nearly an acre! Charming curb appeal and a welcoming covered front porch create a warm first impression. Inside is tons of space for both everyday living and entertaining. The formal dining room opens to a large screened porch, providing a perfect spot to relax or dine. The kitchen offers abundant cabinet storage and generous counter space. A 2nd living room with a fireplace opens onto a deck overlooking the expansive fenced yard. Upstairs are 3 beds and 2 full baths, including a primary with a private bath. Brand-new carpet on the stairs and upper level adds a fresh touch. The walk-out lower level offers even more space with a large rec room, a 3rd full bath, and 2 versatile flex rooms ideal for an office, gym, hobbies, or guests. Conveniently located just minutes from Middleton, Epic, shopping, dining, and parks. It also offers easy access to the Ice Age Trail for hiking and year-round outdoor recreation. See the 3D tour!

3 Beds ⋅ 4 Baths ⋅ 2026641 MLS ⋅ ACTIVE Status

Enjoy peaceful living on a quiet cul-de-sac set on nearly an acre! Charming curb appeal and a welcoming covered front porch create a warm first impression. Inside is tons of space for both everyday living and entertaining. The formal dining room opens to a large screened porch, providing a perfect spot to relax or dine. The kitchen offers abundant cabinet storage and generous counter space. A 2nd living room with a fireplace opens onto a deck overlooking the expansive fenced yard. Upstairs are 3 beds and 2 full baths, including a primary with a private bath. Brand-new carpet on the stairs and upper level adds a fresh touch. The walk-out lower level offers even more space with a large rec room, a 3rd full bath, and 2 versatile flex rooms ideal for an office, gym, hobbies, or guests. Conveniently located just minutes from Middleton, Epic, shopping, dining, and parks. It also offers easy access to the Ice Age Trail for hiking and year-round outdoor recreation. See the 3D tour!

7824 Caribou Ct, Middleton

$369,900

Build your dream custom home with Jason Thomas Homes on Lot 36 in Pioneer Pointe, a top golf community offering scenic views and luxury homes. This spacious lot offers a flexible building area backing to the golf course, with views of the green on hole 4 at Pioneer Pointe Golf Course, making it perfect for a thoughtfully designed home that suits your lifestyle. Live in a desirable neighborhood with easy access to Verona, Middleton, and Madison, along with nearby recreation and amenities. Work directly with Jason Thomas Homes to design and build your dream home on this outstanding lot (walkout possible).

2020655 MLS ⋅ ACTIVE Status

Build your dream custom home with Jason Thomas Homes on Lot 36 in Pioneer Pointe, a top golf community offering scenic views and luxury homes. This spacious lot offers a flexible building area backing to the golf course, with views of the green on hole 4 at Pioneer Pointe Golf Course, making it perfect for a thoughtfully designed home that suits your lifestyle. Live in a desirable neighborhood with easy access to Verona, Middleton, and Madison, along with nearby recreation and amenities. Work directly with Jason Thomas Homes to design and build your dream home on this outstanding lot (walkout possible).

Lot 36 Eden, Middleton

$1,000,000

Two lots create a rare opportunity along a quiet channel with direct access to Lake Mendota, inviting a range of possibilities from thoughtful renovation to a ground-up custom build. The existing home sits between two buildable parcels, allowing for expanded outdoor space, future development, or a private lakeside retreat tailored to your vision. Spend mornings on the water boating or fishing, then return to a backyard dock, with a nearby boat launch adding everyday ease. The setting balances a sense of retreat with practical convenience, just off Century Avenue and minutes from local grocers, dining, and daily essentials. Downtown Madison is an easy 20-minute drive, making this an ideal blend of waterfront living and city access.

3 Beds ⋅ 2 Baths ⋅ 2019384 MLS ⋅ ACTIVE UNDER CONTRACT Status

Two lots create a rare opportunity along a quiet channel with direct access to Lake Mendota, inviting a range of possibilities from thoughtful renovation to a ground-up custom build. The existing home sits between two buildable parcels, allowing for expanded outdoor space, future development, or a private lakeside retreat tailored to your vision. Spend mornings on the water boating or fishing, then return to a backyard dock, with a nearby boat launch adding everyday ease. The setting balances a sense of retreat with practical convenience, just off Century Avenue and minutes from local grocers, dining, and daily essentials. Downtown Madison is an easy 20-minute drive, making this an ideal blend of waterfront living and city access.

2809 Dewey Ct, Middleton

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