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$599,900
4 Beds 3 Baths 2028997 MLS ACTIVE UNDER CONTRACT Status
Welcome home to this beautifully maintained 4-bedroom, 2.5-bath two-story in the sought-after Hickory Woods neighborhood! Situated on over half an acre, this home offers peaceful countryside views, breathtaking sunsets, and a spacious deck perfect for relaxing or entertaining. Enjoy a park across the street, nearby walking and biking trails, easy access to downtown Middleton and Madison, and award-winning Middleton schools. Inside, you’ll find bright living spaces, a spacious eat-in kitchen, and four bedrooms upstairs, including a private primary suite. The partially finished lower level offers additional living space and plenty of hidden storage. Major updates include a new roof (2018) and windows (2019). Thoughtful updates, scenic views, and an exceptional location make this home a must-see!

4507 Stonewood Dr, Middleton

$3,500
3 Beds 3 Baths 2028971 MLS ACTIVE Status
Welcome home to Middleton's desirable Fox Ridge neighborhood on the west side! Spacious 3-4 bedroom duplex! Large windows fill the home with natural light! Functional layout with generous living spaces, kitchen with ample cabinet storage and all appliances. Versatile bedrooms -2 primary bedrooms (1 upper and 1 main level). Walk-in accessible shower, carpeted bedrooms, ceiling fans, window blinds and full basement. Abundant closet space. Enjoy spending time in the beautiful main level 4 season sun room all year round. Nearby parks, walking and biking trails, restaurants, grocery stores. Quick access to major roads. Property is in process of estate clean-out. Occupancy lease signing can start 9/1 to 10/1. Rent would be prorated with occupancy between 9/1 and 10/1. Alternate contact Bryan McKy 608-886-6846 for more information and to make an appointment to see this property!

1206 N High Point Rd, Middleton

$3,750,000
2028946 MLS ACTIVE Status
Rare 15+ acre development opportunity in the highly desirable Town of Middleton. Bordering City of Madison parkland, this exceptional property offers rolling topography, elevated building sites, panoramic countryside views, and a truly one-of-a-kind setting. Located just minutes from Madison's west side, Middleton, shopping, dining, and major employers, it combines a premier location with outstanding long-term investment potential. The property's proximity to the City of Madison presents exciting future annexation possibilities, making it ideal for a signature residential development, luxury estate lots, or other future opportunities, subject to approvals. Surrounded by natural beauty yet close to every convenience, large tracts of land like this rarely become available. Bring your vision and capitalize on one of the area's most unique and desirable development sites.

3440 Meadow Rd, Middleton

$574,900
3 Beds 2 Baths 2028937 MLS ACTIVE Status
Under construction; estimated completion 12/8/26. Welcome to Redtail Ridge—featuring Middleton Schools! Cook’s kitchen with quartz countertops, granite sink, ceramic tile backsplash, stainless steel appliances and spacious 6x4' walk-in pantry with countertops! Great room features gas fireplace with brick surround. Dining area includes walkout to 8x12' patio. Primary bedroom suite features walk-in closet and private bath with tile shower & dual sinks. Main floor laundry room and separate mudroom with built-in wood cubbies. Basement is stubbed for bathroom & includes egress window for future expansion. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior staged photos are of a similar model. Plans & design selections available upon request.

6679 Redpoll Rd, Middleton

$800,000
4 Beds 4 Baths 2028571 MLS ACTIVE UNDER CONTRACT Status
Immaculate Middleton Ridge home on a quiet cul-de-sac in the Middleton-Cross Plains School District! This 4-bedroom, 3.5-bath home offers over 3,700 finished sq. ft. with an open floor plan, hardwood floors, granite countertops, a large kitchen island, pantry, and a cozy gas fireplace. The main level includes a private office and laundry, while the finished lower level features a spacious rec room, hobby room with built-ins, and is great for movie nights. Enjoy the screened porch, grilling deck with gas line, patio with fire pit, and beautifully landscaped backyard. Recent updates include a new roof and refrigerator (2024) and dishwasher (2025). Smart home features include Cat 5 wiring, wireless access points, fiber internet, and an EV charger in the 2-car garage. A move-in-ready home close to Pheasant Branch Conservancy, walking & bike trails, and all Middleton has to offer!

4434 Misty Valley Dr, Middleton

$1,500,000
6 Beds 4 Baths 2028509 MLS ACTIVE Status
Some homes simply check the boxes. Others become the place where memories are made. Nestled in the Back Nine of the Community of Bishops Bay, this custom-built Acker home was designed for gathering, celebrating, & enjoying the moments that matter most. Morning coffee on the screened porch, holidays around the impressive stone fireplace, movie nights in the rec room, & summer evenings around the fire pit in your private yard all become part of everyday life. Beautiful architectural details, soaring ceilings, custom millwork, an impressive Chef's kitchen & thoughtfully designed living spaces create warmth & elegance throughout. Set within one of Dane County's most sought-after communities with a neighborhood pool, clubhouse, fitness enter, parks, trails, & top-rated Waunakee Schools, this is a home you'll never want to leave. Adjacent to renowned private Bishops Bay Golf & Country Club. See attached feature sheet for all upgrades.

4830 Breakers Rock Rd, Middleton

$399,900
3 Beds 1 Baths 2028268 MLS ACTIVE UNDER CONTRACT Status
Charming 1954 ranch in the heart of downtown Middleton! This move-in-ready 3-bedroom, 1.25-bath home is the perfect starter home, loaded with timeless character. Beautiful hardwood floors, original built-ins, and even a classic laundry chute showcase the era's craftsmanship. Recent updates include a new roof, new siding, and new windows for added peace of mind. The basement features a large egress window and open rooms with extra-tall ceilings, offering excellent potential to expand the finished living space. Outside, enjoy a fenced backyard perfect for relaxing, entertaining, or pets. The location is second to none—walk to grocery stores, restaurants, coffee shops, bars, and the scenic trails of Pheasant Branch Conservancy. All of this in the highly sought-after Middleton-Cross Plains School District.

6741 Century Ave, Middleton

$2,100,000
4 Beds 4 Baths 2028201 MLS ACTIVE UNDER CONTRACT Status
Middleton Schools! Lake Mendota living w/72' of prime level frontage, Capitol views & minutes from Middleton's dining, shopping & amenities. Owned by the same family for 55 yrs this beautifully updated 4-bed, 3.5-bath waterfront home blends timeless character w/modern comfort. Remodeled main level features a wonderful kitchen w/new cabinetry, granite counters & stainless steel appliances. Open floorplan flows into the living rm featuring wood-burning fireplace, expansive windows & panoramic lake views. Step onto the lakeside deck for outdoor living & entertaining. Family rm offers an additional gathering space & possible 2nd dining area. Spacious primary suite showcases spectacular lake views, private bath & sitting area w/potential for a custom walk-in closet. Walkout lower level includes rec room w/fireplace, new patio, den & flex space. Updates incl: New flooring/windows/patio drs in LL & main floors, driveway & front stoop. Oversized garage w/epoxy flooring. Close to downtown & UW.

3017 Dianne Dr, Middleton

$775,000
4 Beds 4 Baths 2028114 MLS ACTIVE Status
Charming 4-bedroom, 3.5-bath Craftsman in sought-after Middleton Hills Neighborhood and the Middleton School District! The main level features beautiful wood floors, a spacious kitchen with a walk-in pantry, tiled backsplash, quartz countertops, granite island, maple cabinets, an induction stove, and stainless steel appliances. Enjoy the formal dining room and relax in the spacious living room with a fireplace. Mudroom provides additional storage and access to the attached 2-car garage. A private fenced-in backyard. Upstairs offers a remodeled primary suite with a walk-in closet, plus two additional bedrooms and an updated full bath. Finished walkout lower level includes a second living area, full bath, office or 4th bedroom, and large storage room. Whole-house carbon water filtration system, new HVAC (2022), New Roof & gutters (2024), exterior painted (2024). Enjoy a good book and morning beverage of choice on the front porch swing. Just steps away from Pheasant Branch Conservancy.

6805 Aldo Leopold Way, Middleton

$295,000
2 Beds 1 Baths 2028077 MLS ACTIVE Status
Enjoy carefree condo living in highly desirable Bella Casa community! Ideally located just mins from Greenway Station, Pleasant View Golf Course, dining, parks + downtown Middleton, this light-filled residence offers exceptional combination of comfort + convenience. Open-concept floor plan features hardwood floors, spacious living room w/cozy gas fireplace, + walkout access to a private balcony. Well-appointed kitchen includes SS appliances, breakfast bar, pantry + dining area. French doors open to versatile den, ideal for a home office or extra sleeping space. Retreat to expansive primary bedroom featuring vaulted ceilings, abundant natural light, a generous walk-in closet w/ exceptional storage & spacious ensuite bath w/dual sinks, honeycomb tile flooring. Enjoy outstanding amenities including a beautiful clubhouse w/ kitchen, fitness center & billiards room. Wonderful opportunity to enjoy low-maintenance living in one of Middleton's most convenient locations.

8530 Greenway Blvd Unit 307, Middleton

$750,000
3 Beds 4 Baths 2027799 MLS ACTIVE UNDER CONTRACT Status
Life in Middleton Hills takes on an easy elegance in this thoughtfully designed home, where the ease of condo living meets the privacy of a standalone residence. Lawn care + snow removal are handled for you, creating more time to enjoy the neighborhood’s cafes, restaurants, shops,+nearby trails. Inside, the open-concept main level is grounded by solid hardwood floors and a striking stone fireplace that anchors the great room. The updated kitchen(remodeled in 2022) flows seamlessly into the dining area which leads to a private screened porch, ideal for outdoor dining or quiet mornings. 2nd floor has 3 bedrooms and 2 full baths(both remodeled in 2022). The finished lower level expands the living/entertaining space, offering flexibility for movie nights, guests, or a home office. Just moments from the neighborhood grocery store, schools, and Pheasant Branch Conservancy. Current condo fees are $350/month. New Roof+Gutters-2026, New HVAC-2025. EV Charger in garage.

6750 Frank Lloyd Wright Ave, Middleton

$750,000
3 Beds 4 Baths 2027706 MLS ACTIVE UNDER CONTRACT Status
Life in Middleton Hills takes on an easy elegance in this thoughtfully designed home, where the ease of condo living meets the privacy of a standalone residence. Lawn care + snow removal are handled for you, creating more time to enjoy the neighborhood’s cafes, restaurants, shops,+nearby trails. Inside, the open-concept main level is grounded by solid hardwood floors and a striking stone fireplace that anchors the great room. The updated kitchen(remodeled in 2022) flows seamlessly into the dining area which leads to a private screened porch, ideal for outdoor dining or quiet mornings. 2nd floor has 3 bedrooms and 2 full baths(both remodeled in 2022). The finished lower level expands the living/entertaining space, offering flexibility for movie nights, guests, or a home office. Just steps from the neighborhood grocery store, schools, + Pheasant Branch Conservancy, this home pairs everyday convenience with a connected, walkable lifestyle. New Roof+Gutters-2026, New HVAC-2025, EV Charger

6750 Frank Lloyd Wright Ave, Middleton

$435,000
2 Beds 1 Baths 2023964 MLS ACTIVE UNDER CONTRACT Status
Inviting ranch home in Middleton, conveniently located near Lakeview Park Splash Pad, Sauk Trail Elementary School, Willy Street Co-op, and popular dining spots. The smart layout features a formal dining room and updated kitchen, creating an easy flow for entertaining and everyday living. Unwind in your private sunroom overlooking the beautifully landscaped backyard, the perfect spot to relax and enjoy the changing seasons. The unfinished lower level offers excellent potential to add finished living space, such as a rec room or family room. Enjoy the top-rated Middleton-Cross Plains School District, beautiful hardwood floors, and a one car attached garage. A wonderful opportunity combining location, value, and future potential.

6622 Franklin Ave, Middleton

$327,000
2 Beds 3 Baths 2027562 MLS ACTIVE Status
Move right into this end-unit condo in the highly sought-after Middleton School District! Ideally located just minutes from Blackhawk Park, West Towne Mall, and the Beltline, this home offers the perfect blend of comfort and convenience. The open-concept main level features a spacious living room with a cozy gas fireplace, dining area, and kitchen complete with stainless steel appliances. Upstairs, you'll find two generously sized bedrooms, each with its own private en-suite bathroom, plus conveniently located second-floor laundry. Step outside to the Trex deck, perfect for grilling or relaxing on warm summer evenings. Complete with a 2-car attached garage and low-maintenance condo living, this home is ready for you to enjoy!

707 Cricket Ln Unit 5, Middleton

$1,799,000
5 Beds 7 Baths 2027557 MLS ACTIVE UNDER CONTRACT Status
Custom home w/ classic beauty + timeless elegance, perfectly suited on over 1.4 landscaped acres w/waling trails connecting to green space. Grand in scale + design, this thoughtfully crafted residence offers sweeping views, floor-to-ceiling windows, & open yet refined floor plan. Chef's kitchen offers Wolf appliances, Sub-Zero refrigeration, custom cabinetry, + exceptional workspace. Rich woodwork, crown molding, tray ceilings, nine-foot doors, + three stone gas fireplaces showcase impeccable craftsmanship. Luxurious primary features a spa-inspired bath w/ steam shower, body sprays, soaking tub, + expansive walk-in closet. 4 addtl ensuite bedrooms each include private baths + walk-in closets. Walkout LL w/ a spacious family room, Tuscan-inspired brickwork, wet bar + wine cellar. Amenities include exercise room, sunroom, patios, 4-car garage, central vac, programmable irrigation system + much more! A truly remarkable home offering luxury + exceptional attention to detail.

3952 Caribou Rd, Middleton

$879,900
4 Beds 3 Baths 2027365 MLS ACTIVE Status
Classic 1920 Craftsman bungalow on a prime corner lot in the heart of downtown Middleton — that rarely comes to market. This 3-BR, 2.5-BA character home blends original charm with everyday livability: maple hardwood floors, classic woodwork, tall ceilings, a formal dining room, and natural light throughout. First floor powder room, laundry & a mudroom for everyday function. Upstairs, the primary bedroom offers a walk-in closet & updated BA, w/ additional bedrooms and a 2nd full bath w/clawfoot tub. A 2-car detached garage plus a 3rd covered stall provides rare in-town parking & storage. Downstairs, 1,100-square-foot unfinished basement w/ high ceilings offers tons of potential. The showpiece is the deep covered front porch, framed by brick columns & roomy enough for a swing & a full seating area. New roof and new furnace. Walk to parks, restaurants, coffee shops, festivals, & the public library.

7226 Hubbard Ave, Middleton

$249,000
2 Beds 1 Baths 2027352 MLS ACTIVE Status
Conveniently located near shopping, restaurants, and the bus line, this beautifully updated end-unit condo offers comfort, convenience, and investment potential. Featuring 2 bedrooms, 1 full bath, an open layout, in-unit washer and dryer, and a spacious private balcony, this home is move-in ready. Enjoy the convenience of heated underground parking with one assigned space, elevator access, and secure building amenities. Currently operating as a successful short-term rental, this property offers rental income potential through the remainder of the year. The established short-term rental business and all furnishings are available for purchase separately, providing a turnkey investment opportunity or a fully furnished personal retreat. Don't miss this versatile property in an exceptional location!

2051 Allen Blvd Unit 201, Middleton

$250,000
1 Beds 1 Baths 2027314 MLS ACTIVE Status
LAKE MENDOTA FRONTAGE! MODERN UPDATES! GARAGE! EXCELLENT MIDDLETON LOCATION! This condo project has prime frontage on the Lake & possibilities for a boat slip! Rare opportunity! Perfect for those who want a second home on the lake or a year-round perfect location on the bus line w/ quick access to UW & Madison hospitals! Walk in & be greeted by a beautiful great rm w/ high vaulted ceiling &modern LVP flooring that extends into the spacious dinette &the updated kitchen w/granite countertops &stainless-steel applcs! King size Master w/walk-in closet. Completely updated bath! Enjoy the large deck overlooking the relaxing outdoor pool! Don't forget to bring your kayak, paddle boards &canoe! Keep them right on the level lake frontage &enjoy lake life & carefree living at its best! Sit around the fire pit & take in the breathtaking lake views &Madison Skyline! Call for details on the pier & boat slips! Underground Parking spot 44, Storage unit 14

2809 Century Harbor Rd Unit 3, Middleton

$1,050,000
5 Beds 3 Baths 2027286 MLS ACTIVE UNDER CONTRACT Status
High atop the hills of the Conservancy View Neighborhood in Middleton, this 5 bed, 3 bath custom built contemporary craftsman will impress the most discerning homebuyer. Imagine waking up to panoramic views of Pheasant Branch Conservancy while enjoying your coffee on the screen porch. Entertaining in this home is a must with 13 ft ceilings, studio style lighting and a culinary enthusiast's dream kitchen. Massive center island in the kitchen with seating for 6, dedicated pantry and views to delight. Dedicated dining room and a 3 sided gas fireplace finish off the main floor. Upstairs the owner's suite is an oasis with an extra large jetted tub, walk in shower and dual vanities. The lower level features a guest bedroom, office, rec room with a wet bar built in. Enjoy the privacy in your hot tub on the back deck. Homes sits next to greenspace and backs up to Middleton Hills North Park. Oversized 3 car, tandem garage with electric for the EV car charger, new roof 2026.An absolute must see!

6711 S Chickahauk Trl, Middleton

$275,000
2 Beds 1 Baths 2026783 MLS ACTIVE Status
In search of an investor or first time buyer. Great starter home that does need some improving. Put in some sweat equity and take advantage of a lower priced home in an excellent Middleton location. Sits along bus line and is walking distance to schools, shopping, and restaurants. Seller purchased the home for a family member and has never occupied the home, therefore prefers to sell as is. Seller will include an Ultimate Universal Home Protection plan at the cost of $825 - which covers 13 months and is renewable annually. Water heater and water softener are 1 year new. The backyard deck slightly encroaches on the neighbor's property. Seller is having the property surveyed and I will update all parties once that has been completed.

1702 Park St, 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.