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$324,500
3 Beds ⋅ 2 Baths ⋅ 2030173 MLS ⋅ ACTIVE Status
Invest in your future and build equity with this 3-bedroom, 2-bath half-duplex in the heart of highly desirable Middleton! This inviting home features an updated & stylish kitchen, two separate living areas affording plenty of room to spread out, split bedrooms for home office or guest space, and an attached garage. Take advantage of yard space and an outstanding location within walking distance off Pheasant Branch Conservancy, schools, parks, Lake Mendota, restaurants, and more! This home combines space, convenience, opportunity, and an exceptional location - welcome home!

6404 Maywood Ave, Middleton
$685,000
4 Beds ⋅ 4 Baths ⋅ 2018775 MLS ⋅ ACTIVE UNDER CONTRACT Status
Immaculate 4 bed, 3.5 bath 2-story in Middleton’s Misty Valley! The inviting lvg rm w/soaring 16 ft ceiling, abundant natural light & hdwd flrs flow seamlessly into the sleek kitchen w/white cabinets, SS appliances, peninsula w/bfast bar & dinette. You’ll love the main lvl primary w/ensuite bath feat dual sinks, new shower & walk-in closet. A 1/2 bath & mudrm w/cubbies round out the main lvl. Upstairs, you’ll find a laundry rm w/utility sink & 3 large beds, incl one w/walk-in closet & access to full bath. Entertain or relax in the exposed & bright LL family rm w/gas FP, SS speakers & granite wet bar w/dishwasher & bev fridge. Work or workout in the versatile flex rm. Outside, unwind in the screened porch overlooking the private, fenced yard w/no back neighbors, or on the patio with gas fire pit. Many updates & close to top-rated Middleton schools, Pheasant Branch Conservancy, restaurants & groceries. This is a rare chance to own such a beautiful home in this location and price point!

7103 Caneel Trl, Middleton
$465,000
3 Beds ⋅ 2 Baths ⋅ 2030118 MLS ⋅ ACTIVE Status
Set within Middleton’s historic Pheasant Branch Crossing and steps from Middleton Hills, this home offers an ideal combination of outdoor access, everyday convenience, and a spacious lot. Grocery store and local favorites including Craftsman, Prairie Cafe, and Miggy’s Bakes are all within a block. Set on nearly half an acre, the property has a large fenced backyard with plenty of room to garden, play, or gather around the fire pit. A back deck extends the living space outdoors and a shed provides additional storage. Inside, the main level features a primary bedroom and half bath, while 2 additional bedrooms and a full bath are located upstairs. One of the upstairs rooms is especially spacious, with plenty of space for a sitting area/home office. The lower level offers a walkout to the backyard. A separate workshop area can be converted back to a 1-car garage. With a layout that offers flexibility and spaces that can evolve with your needs, this home is ready for its next chapter.

2865 Old Creek Rd, Middleton
$575,000
3 Beds ⋅ 4 Baths ⋅ 2030056 MLS ⋅ ACTIVE Status
Showings to begin 08/21/2026 - 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
$965,000
5 Beds ⋅ 4 Baths ⋅ 2029944 MLS ⋅ ACTIVE Status
Brand new, never-lived-in 2026 Parade of Homes home by Encore Builders on a premium Redtail Ridge lot with commanding sunrise views of Pheasant Branch Conservancy from all three levels! Thoughtfully oriented for southern exposure, this stunning architectural design features an open-concept great room with a dramatic 2-story vaulted ceiling, a custom fireplace and built-in cabinetry. The cook’s kitchen offers quartz countertops, stainless steel appliances and an oversized pantry. Enjoy a luxurious main-level primary suite, flex room/office, 3-season porch with east and south exposures, and a finished lower level filled with windows and natural light. Features include 5 bedrooms, 4 baths, 3,747 sq ft per digital scan, enhanced landscaping, 12’x17’ patio, 2.5-car garage with extra storage, security system, active radon reduction, 10-year builder limited warranty and 15-year dry basement warranty. Top-rated schools, future community park and Pheasant Branch Conservancy just one block away.

4525 Hooded Merganser Dr, Middleton
$325,000
2029942 MLS ⋅ ACTIVE Status
Build your dream home on this beautiful 0.727-acre lot in the Town of Middleton, located in the highly sought-after Middleton-Cross Plains School District! This open, level homesite offers the perfect canvas for your custom home, with ample space for outdoor living and endless design possibilities. Situated in an established neighborhood with quick access to major highways, you’ll enjoy the convenience of being just minutes from downtown Middleton, West Madison, shopping, dining, parks, and everyday amenities. Natural gas and electricity are available, with well and septic required. Bring your own builder and take advantage of this rare opportunity to create your ideal home in one of the area’s most desirable communities.

Lot 14 Highwood, Middleton
$630,000
4 Beds ⋅ 3 Baths ⋅ 2029941 MLS ⋅ ACTIVE Status
Welcome to Hidden Oaks, where quality craftsmanship meets serene surroundings. This beautifully maintained ranch-style home features 4 bedrooms and 3 baths, offering the perfect blend of comfort, style, and functionality. Nestled on a spacious lot that backs onto protected green space and a conservancy, you'll enjoy stunning views and enhanced privacy. The open-concept layout boasts 9-foot ceilings and a great room with a stone gas fireplace. The kitchen is ideal for entertaining, with a large center island and a seamless flow into the dining area. Step out onto the deck overlooking the fenced backyard. The main level includes three spacious bedrooms, highlighted by a primary suite with a walk-in closet and dual vanities. The lower level features a family room, a fourth bedroom, a full bath, and ample storage. This exceptional home is in a desirable Middleton neighborhood, close to parks, schools, and shopping.

8927 Sunstone Ln, Middleton
$549,900
4 Beds ⋅ 3 Baths ⋅ 2029928 MLS ⋅ ACTIVE Status
This four-bedroom luxury ranch features a spacious open floor plan with plenty of natural light. The great room features cathedral ceilings, skylights, a fireplace with a wood mantel, and sliding patio doors leading to a fully enclosed three-season room. The kitchen comes fully equipped with all appliances, a pantry, and a built-in desk. The primary suite offers vaulted ceilings, two closets, and a private bath with a double-sink vanity. Downstairs, the finished exposed lower level includes a second family room, two additional bedrooms, and a full bath.

9110 Waterside St, Middleton
$750,000
3 Beds ⋅ 3 Baths ⋅ 2029323 MLS ⋅ ACTIVE Status
Spacious, updated ranch-style condo in Bishop's Bay with a main-level primary suite. 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
$274,900
1 Beds ⋅ 1 Baths ⋅ 2029617 MLS ⋅ ACTIVE Status
Comfort, convenience and condo living come together in Middleton! This 1-bedroom, 1-bath condo welcomes you with an open floor plan that makes everyday living and entertaining feel effortless. Pull up a stool at the breakfast bar, settle in beside the gas fireplace, or enjoy a quiet moment in the sunroom. Two spaces in the heated underground parking garage offer a welcome perk through every Wisconsin season, while an included storage unit keeps extras close at hand. The community clubhouse expands your options with an additional kitchen and exercise room. Set along Greenway Blvd, this inviting condo puts Middleton shopping, dining, recreation and everyday conveniences within easy reach. An ideal place to simplify your routine and enjoy the amenities of condo living!

8510 Greenway Blvd Unit 104, Middleton
$800,000
5 Beds ⋅ 4 Baths ⋅ 2029565 MLS ⋅ ACTIVE Status
Welcome home to this immaculate and beautifully maintained 5-bedroom home in the desirable Northlake neighborhood, offering an impressive combination of space, style, and privacy. With no neighbors directly behind, this home provides a peaceful setting and a backyard designed for relaxing and entertaining.The main floor offers an exceptional amount of living space with a formal living room, formal dining room, family room, powder room, laundry room, and a bright sunroom filled with natural light. Whether you’re hosting a holiday dinner, enjoying a quiet morning in the sunroom, or relaxing at the end of the day, there’s a space for every occasion.The finished lower level adds even more usable living space and is ready for fun! Enjoy a family room, workout area, and an additional fifth bedroom featuring a convenient Murphy bed—perfect for overnight guests while still allowing the room to serve multiple purposes. Ultimate home warranty included.

5502 Upland Trl, Middleton
$449,900
3 Beds ⋅ 2 Baths ⋅ 2029558 MLS ⋅ ACTIVE UNDER CONTRACT Status
Single level living in desirable Northlake! Showings begin 9/8/26.

5410 Sandhill Dr, Middleton
$773,900
3 Beds ⋅ 3 Baths ⋅ 2029531 MLS ⋅ ACTIVE Status
Under construction; estimated completion 12/17/26. Welcome to Redtail Ridge-featuring Middleton schools. Enjoy stunning back yard views of Pheasant Branch Conservancy with this open plan ranch! Expansive vaulted great room with floor to ceiling brick fireplace. Cook’s kitchen features quartz countertops, granite sink, ceramic tile backsplash, slate appliances, and walk-in pantry. Dining area opens to elevated screened porch with extra Trex deck area for grilling! Primary bedroom suite features a large walk-in closet and spacious private bath with tile shower & dual sinks. Flex room for office, playroom, etc. Main floor laundry room with built-in wood cubbies. Full exposure basement is stubbed for bathroom and includes walkout to 17x10’ patio. Garage includes extra 3x22' expansion for extra storage. 10yr builder's limited warranty & 15yr dry basement warranty included! Photos are of a similar model. Plans & design selections available upon request.

4513 Hooded Merganser Dr, Middleton
$849,900
5 Beds ⋅ 3 Baths ⋅ 2029103 MLS ⋅ ACTIVE Status
Show 8/19. Welcome home to this stunning 5 bedroom ranch-style retreat where thoughtful design meets effortless comfort! A charming front porch welcomes you into an open-concept layout boasting a mud/laundry room, split style beds, cozy living room w/ gas fp & custom built-ins! Kitchen shines with all SS apps, spacious island, walk-in pantry, beverage center, and dining area w/ walkout to SW-facing screened porch, with a new screen coming soon! ML primary offers a private en-suite bath & WIC. The lower level offers a spacious rec room, 2 additional bedrooms, & walkout leading to the beautifully landscaped yard/patio—perfect for entertaining. An extended 2-car garage adds extra versatility, while solar panels provide added efficiency. Located in the desirable Waunakee School District and Bishops Bay community, residents also enjoy access to the neighborhood pool and clubhouse. Plus, a new roof is coming soon! This home truly has it all!

4408 Blackwolf Run, Middleton
$700,000
4 Beds ⋅ 4 Baths ⋅ 2029095 MLS ⋅ ACTIVE UNDER CONTRACT Status
Showings start 7/31 @ 3:30pm. Some homes simply provide shelter. This one offers a place to put down roots. Nestled in the heart of Prairie Home Estates, this beautifully appointed two-story home is surrounded by the kind of neighborhood families dream about—where evening walks become tradition, kids ride bikes to the nearby tennis courts, soccer fields and baseball diamonds, and miles of scenic prairie trails are just steps from your front door. Inside, generous living spaces invite everything from holiday celebrations to cozy nights together, while large windows bring the outdoors in. Outside, the private backyard is framed by mature landscaping, colorful gardens, and a charming strawberry patch that has been lovingly cultivated through the years. Here you'll find more than a beautiful home—you'll find a welcoming community, lifelong friendships, and a place where the moments that matter most naturally unfold.

8437 Ellington Way, Middleton
$174,900
2029086 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L267 Thrasher St, Middleton
$174,900
2029084 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L266 Thrasher St, Middleton
$174,900
2029083 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L265 Thrasher St, Middleton
$214,900
2029082 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L255 Thrasher St, Middleton
$219,900
2029080 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L253 Thrasher St, Middleton
$214,900
2029079 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L250 Thrasher St, Middleton
$214,900
2029077 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L247 Thrasher St, Middleton
$204,900
2029074 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L244 Hooded Merganser Dr, Middleton
$204,900
2029073 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L242 Hooded Merganser Dr, Middleton
$214,900
2029072 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L238 Hooded Merganser Dr, Middleton
$249,900
2029071 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L235 Towhee Dr, Middleton
$249,900
2029070 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L233 Towhee Dr, Middleton
$224,900
2029069 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L211 Towhee Dr, Middleton
$224,900
2029067 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L210 Hooded Merganser Dr, Middleton
$224,900
2029065 MLS ⋅ ACTIVE Status
Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas, including nearby Pheasant Branch Conservancy, as well as Pleasant View Golf Course and Lakeview Park. Shopping, dining, and services are minutes away at Greenway Station and Historic Downtown Middleton. Lot sale is subject to a separate building agreement with Tim O’Brien Homes.

L208 Hooded Merganser Dr, Middleton

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.