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6671 S Chickahauk Trl, Middleton
$789,000
4 Beds ⋅ 4 Baths ⋅ 2034086 MLS ⋅ ACTIVE Status
Wake up to some of the most spectacular views in Middleton. Overlooking the Pheasant Branch Conservancy, this stand-alone condo offers a rare blend of privacy, comfort, and connection to nature. Expansive windows fill the home with natural light while showcasing beautiful views year-round. Warm oak floors welcome you into the open-concept main level, where a spacious living room with a gas fireplace flows into the dining area and kitchen. Designed for everyday living and entertaining, the kitchen features a center island with seating, and a walk-in pantry. Meticulously maintained and move-in ready, the home offers multiple living spaces. The bright walk-out family room opens to a private patio, while the spacious primary suite features abundant natural light, a large walk-in closet, soaking tub, and separate walk-in shower. Enjoy low-maintenance condo living, near parks, trails, schools, shopping, and dining in one of Middleton's most scenic settings.

6671 S Chickahauk Trl, Middleton

3414 Valley Ridge Rd Unit 3, Middleton
$280,000
2 Beds ⋅ 2 Baths ⋅ 2034037 MLS ⋅ ACTIVE Status
Condo community Surrounded by Nature. Come On In! Surround yourself with premier quality updates found in this well maintained 1st floor unit in an established assoc. and treed neighborhood. Warm Neutral colors and white trim throughout. Desired updates include: Beautiful LVP Flooring in Living Rm-Dining Area & Hallways. Galley Kitchen offers corian Ctops-newer SS Appliances-Maple Cabinets. Both baths with newer vanities-flooring & showers with custom tile surround. Windows & Light Fixtures replaced. Primary BR has dbl closet. 2nd BR has queen size Murphy Bed. Stacked Washer & Dryer included. Extra large Linen Closet. Condo fee includes a 1 car underground parking space, storage area, an internet service and hot water. A private patio with brick wall off of LR for your personal enjoyment or gather with your neighbors in the several sitting areas or Gazebo! Pet Friendly. Close to Middleton Conservancy, Shopping, & Busline.

3414 Valley Ridge Rd Unit 3, Middleton

7017 Prairie Dr, Middleton
$474,900
3 Beds ⋅ 2 Baths ⋅ 2033718 MLS ⋅ ACTIVE Status
Charming and spacious 3-bedroom ranch in Middleton’s sought-after Parkside Heights neighborhood! Designed with plenty of room to gather, relax, and entertain, the main level features a welcoming living room, formal dining room, cozy family room, and eat-in kitchen. The spacious primary suite offers a walk-in closet and private half bath, while two additional bedrooms provide flexibility for family, guests, or a home office. Downstairs, the finished lower level adds even more living space with a versatile office/den featuring a wood-burning fireplace, plus abundant unfinished space for storage or hobbies. Outside, enjoy a private fenced backyard with a stamped patio—perfect for summer gatherings. An oversized 2-car garage adds valuable storage and convenience. Ideally located just steps from parks and close to schools, restaurants, shopping, and more. Well-maintained with major mechanical updates including a 2012 A/C, 2004 furnace, and 2017 water heater. Come make this one yours!

7017 Prairie Dr, Middleton

4002 Misty Valley Dr, Middleton
$644,900
3 Beds ⋅ 3 Baths ⋅ 2033407 MLS ⋅ ACTIVE Status
Move-in ready 12/2/26. This Kennedy home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler® and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

4002 Misty Valley Dr, Middleton

7777 Elmwood Ave Unit 208, Middleton
$499,900
1 Beds ⋅ 2 Baths ⋅ 2033283 MLS ⋅ ACTIVE UNDER CONTRACT Status
Showings begin on 10/04/26. Authentic industrial loft living in the heart of downtown Middleton! Located in a historic all-brick warehouse converted to condos, this south-facing 1BR. 1.5BA loft is filled with character: original exposed brick, soaring ceilings, oversized windows, industrial metal trusses & exposed ductwork. Polished concrete floors anchor the main level, while warm wood floors lead to the open loft bedroom above. Updated kitchen features stainless appliances, large island & modern finishes; both baths have also been beautifully updated. Primary bath includes a bidet & hidden refuse bin. Gas fireplace, remote-controlled blinds & balcony overlooking the park-like grounds. Leave the car parked! Walk to 3 coffee shops, 10+ restaurants, grocery, post office, gyms, salons, parks, Tuesday Farmers' Market & Capital Brewery—where you can even enjoy live music from your balcony. Historic character + modern updates + an unbeatable downtown Middleton lifestyle.

7777 Elmwood Ave Unit 208, Middleton

6619 Cooper Ave, Middleton
$465,000
4 Beds ⋅ 2 Baths ⋅ 2033236 MLS ⋅ ACTIVE Status
Welcome home to this well-maintained single-family home in desirable Middleton-Cross Plains Area School District! Thoughtful updates throughout provide peace of mind while leaving plenty of opportunity to make the space your own. Major recent improvements include a new roof (2026), remodeled full bathroom (2026), new LVP flooring in the basement (2026), and a new electrical panel (2024). For added comfort and efficiency, the home features two AC mini-split systems installed in 2024, with capacity to add an additional unit. The refreshed lower level offers versatile space for a rec room, home office, workout area, or additional living space. With many of the big-ticket updates already completed, this home offers a great combination of comfort, functionality, and long-term value—all in Middleton with convenient access to shopping, dining, parks, and area amenities. Schedule your showing and see everything this home has to offer!

6619 Cooper Ave, Middleton

5019 Prairie Rose Ct, Middleton
$724,000
3 Beds ⋅ 3 Baths ⋅ 2033044 MLS ⋅ ACTIVE Status
SPECTACULAR RANCH STYLE CONDO IN DESIRABLE BISHOPS BAY NEIGHBORHOOD. One level living (primary bedroom, laundry, deck all on main floor). Located on a cul-de-sac for extra privacy. New roof September 2026. Andersen windows. Main level with cathedral ceiling, many large windows, maple wood flooring and a solar tube give this area an abundance of sunlight. LIVING ROOM (gas fireplace w/ tile surround, patio doors to maintenance free deck, decorative ceiling fan, built in cabinetry), KITCHEN (Island, breakfast bar, gas cook top, SS appliances, solid surface countertops, spectacular cabinetry, tile backsplash), DINING AREA (room for large table), PRIMARY BEDROOM (new LVP flooring, ceiling fan, walk-in closet, ensuite bathroom w/ double sinks, soaking tub, walk-in shower), LAUNDRY ROOM (washer, dryer included, tile floor), POWDER ROOM (guest bathroom). The Lower Level w/ new LVP flooring; BEDROOM #2 and BEDROOM #3. FULL BATHROOM (cabinetry). REC ROOM (access to patio) Large storage room.

5019 Prairie Rose Ct, Middleton

4428 Blackwolf Run, Middleton
$799,900
4 Beds ⋅ 3 Baths ⋅ 2032841 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to this GORGEOUS CRAFTED RANCH HOME in sought-after Bishops Bay. This home has 4 bedrooms, 3 baths, 2.5 car garage & 1st Floor Laundry! The heart of the home has an open-concept with STUNNING UPDATED Kitchen with a large work island, quartz countertops, under cabinet lighting & champagne hardware! Gather in the great room, accented by coffered ceilings, custom built-ins & a stone gas fireplace. Screen porch overlooking private backyard & patio! Large primary suite w/private full bath that has dual sinks, heated floors, a walk-in tiled shower, soaking tub & large walk-in closet w/organizers! A second bedroom sits just off a full bath & has a walk-in closet. In your finished lower level enjoy a family room w/exposed windows & walkout to backyard, two more bedrooms & a large shared bath + tons of storage! Close to parks, grocery stores & Golf Course! — HOA covers pool, fitness & community room access, all near a renowned golf club. New Roof-2026! New Water Softener 2026!

4428 Blackwolf Run, Middleton

7473 Meadowrue Cir, Middleton
$775,000
4 Beds ⋅ 4 Baths ⋅ 2032736 MLS ⋅ ACTIVE UNDER CONTRACT Status
Perched atop one of the highest points in the subdivision, at the end of a quiet cul-de-sac, this exceptional home offers a rare blend of privacy, luxury, and natural beauty. Set on over half an acre, this home borders an incredible network of conservancy land, parks, and walking trails. Every season paints a different view. Inside, you'll find over 3,500 sq. ft. with soaring ceilings, expansive windows that bring the outdoors in, multiple living spaces, a dedicated office, and a stunning cedar four-season sunroom. The spacious primary suite, finished lower level with Brazilian teak hardwood floors and surround sound, composite deck, and numerous major updates—including furnace, A/C, and new carpet throughout complete this exceptional home in the highly sought-after Middleton School District

7473 Meadowrue Cir, Middleton

7901 Windermere Ct, Middleton
$1,599,000
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

6514 Mendota Ave, Middleton
$574,900
3 Beds ⋅ 3 Baths ⋅ 2032045 MLS ⋅ ACTIVE UNDER CONTRACT Status
Charming brick 3 bedroom, 2.5 bath home set on a rare, private half acre lot, a setting that's hard to find this close to everything. With nearly 3,000 square feet, there is plenty of room to spread out and make this home your own. The beautifully updated kitchen features Wolf appliances, quartz countertops, and custom cabinetry, opening to a bright sunroom overlooking the gorgeous backyard. The outdoor space is truly special, with established garden beds, a shed, and an abundance of raspberry and blackberry bushes. Cozy up by the gas fireplace on cooler evenings, then head downstairs to the finished lower level, offering a flexible blank canvas ready for your vision and dedicated workshop space. Thoughtfully maintained and well cared for, this home offers a wonderful combination of space and privacy. Ideally located just minutes from Lakeview Park, Lake Mendota, and downtown Middleton. Pre inspected for peace of mind. This is a truly special home ready for its next chapter!

6514 Mendota Ave, Middleton

7115 Johann Farm Rd, Middleton
$624,900
3 Beds ⋅ 3 Baths ⋅ 2031967 MLS ⋅ ACTIVE Status
Move-in ready 11/30/26. This Sawyer home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler® and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

7115 Johann Farm Rd, Middleton

5413 Jonquil Ct, Middleton
$550,000
3 Beds ⋅ 3 Baths ⋅ 2031731 MLS ⋅ ACTIVE Status
Don’t miss this home with stylish updates in an ideal location just minutes from Orchid Heights Park, Pheasant Branch, downtown Middleton, and Lake Mendota. Inside, the sun-filled living room with a fireplace and the lofted second floor create a bright, welcoming feel. New hardwood floors on the main level add warmth and character, and the spacious kitchen offers tons of storage and new stainless steel appliances. The family room has a relaxed, cozy feel and opens onto a patio. A main-level laundry room and mudroom off the garage make everyday life a little easier. Upstairs are two bedrooms and a full bath. Plus, a primary suite with a private full bath. Out back, the deck is ready for morning coffee, outdoor meals, or hanging out with guests. The lower level has a finished flex room and more space to expand. A fun, functional home with personality, thoughtful updates, and an unbeatable Middleton location. See the virtual tour!

5413 Jonquil Ct, Middleton

7111 Johann Farm Rd, Middleton
$574,900
3 Beds ⋅ 3 Baths ⋅ 2031729 MLS ⋅ ACTIVE Status
Move-in ready 11/16/26. This Beryl home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler® and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

7111 Johann Farm Rd, Middleton

4686-4688 Capitol View Rd, Middleton
$849,900
2031478 MLS ⋅ ACTIVE Status
Rare opportunity to own one of the few investment properties in the Town of Middleton on a large 1.2-acre lot! Enjoy breathtaking countryside views for miles from this exceptional duplex, professionally remodeled from top to bottom with quality finishes throughout. Each unit offers 3 bedrooms, 2 full bathrooms, spacious basement rec room, and additional versatile flex room, private laundry, attached 2-car garage. Each unit has a large concrete patio, great for enjoying the outdoors & sunset or sunrise views! Bonus features include a fenced in yard (4686) and a pergola (4688). Located in the highly rated Middleton-Cross Plains School District & the large lot size offers the possibility for potential additional development or building in the future. Potential for increased future rents to bring them up to market value! This turnkey property offers a great opportunity for investors or owner-occupants seeking rental income without sacrificing space, comfort, or location!

4686-4688 Capitol View Rd, Middleton

6648 Redpoll Rd, Middleton
$619,900
4 Beds ⋅ 3 Baths ⋅ 2031196 MLS ⋅ ACTIVE Status
Under construction; estimated completion 12/1/26. Welcome to Redtail Ridge—featuring Middleton Schools! Cook’s kitchen with quartz countertops, granite sink, ceramic tile backsplash, stainless steel appliances, and walk-in pantry. Great room features gas fireplace with ceramic surround & reeded wall accent. Dining area includes walkout to 6x12' patio. Main floor flex room with double glass doors for office, playroom, etc. Primary bedroom suite features two closets—one standard and one walk-in!—and private bath with tile shower & dual sinks. Convenient upper level laundry room and separate mudroom with built-in wood cubbies off garage. Garage features bonus 15’ deep 3rd car space. Basement is stubbed for bathroom & includes egress window for future expansion. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos are of a similar model. Plans & design selections available upon request.

6648 Redpoll Rd, Middleton

2004 Butler Ct, Middleton
$599,999
3 Beds ⋅ 3 Baths ⋅ 2031089 MLS ⋅ ACTIVE Status
PRICE REDUCED! Open House 9/29, 4p-6p Welcome to 2004 Butler Court, a beautifully appointed, free-standing condo tucked away on a quiet Middleton cul-de-sac. This light-filled home offers 3 bedrooms, 2.5 baths and a fabulously low condo fee. The open main level features hardwood floors, a gas fireplace, patio access and a flexible office or den. The spacious kitchen boasts granite countertops, an island, abundant cabinetry and an oversized walk-in pantry. The main-level primary suite includes a walk-in closet and tiled walk-in shower. The exposed lower level adds a second living area, 2 bedrooms and a full bath—ideal for guests or recreation. Additional highlights include paneled doors, custom blinds, ample storage and a new roof installed 8/26 all just minutes from downtown Middleton, Lake Mendota, Pheasant Branch Conservancy, shopping, restaurants, UW–Madison and UW Hospital. Assumable FHA Mortgage, with qualification. Measurements are approximate; buyer to verify.

2004 Butler Ct, Middleton

6715 S Chickahauk Trl, Middleton
$1,100,000
5 Beds ⋅ 5 Baths ⋅ 2031010 MLS ⋅ ACTIVE Status
SELLER-PAID RATE BUYDOWN AVAILABLE! Make this refined, thoughtfully designed home yours! Back on the market with: a NEW roof, NEW patio doors, and NEW balcony door. Open gathering spaces & private retreats are perfectly balanced in this 5 bedroom 4.5 bath home. The main level flows effortlessly: a light-filled living room with soaring ceilings & gas fireplace, dining room, expansive chef’s kitchen, and outdoor patio. The private primary suite offers a spa-like bath & garden access, while a 2nd en-suite bedroom adds flexibility. Upstairs, 2 bedrooms share a bath, & share a charming balcony with countryside views. The lower level features a 2nd living area or theater, wet bar, full bath, & 5th bedroom—ideal for guests or extended stays. Low-maintenance lot near Pheasant Branch Conservancy.

6715 S Chickahauk Trl, Middleton

6659 Linnet Ln, Middleton
$624,900
4 Beds ⋅ 3 Baths ⋅ 2030788 MLS ⋅ ACTIVE Status
Welcome home to this beautiful 4-bedroom home in the highly sought-after Middleton School District! A charming covered front porch welcomes you into a bright, open-concept floor plan designed for comfortable everyday living and entertaining. The great room features a cozy fireplace and flows seamlessly into the kitchen with a spacious island. Enjoy the convenience of a main-floor primary suite complete with a private en suite featuring a tiled shower and double vanity. Main-floor laundry and a 3-car garage add functionality and storage. Upstairs, you’ll find three additional bedrooms, a full bathroom, and a versatile flex room perfect for a home office, playroom, den, craft room, or whatever fits your lifestyle. With a thoughtful layout, flexible living spaces, and a desirable location close to shopping and nature, this home has so much to offer!

6659 Linnet Ln, Middleton

7744 Pamela Cir, Middleton
$1,385,000
5 Beds ⋅ 5 Baths ⋅ 2030777 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to this gorgeous home set on 1.5 acres in the highly rated Middleton School District. Offering the perfect blend of space, privacy, and thorough updates, this property has been meticulously improved for comfortable, worry-free living throughout. Main level primary ensuite. Recent upgrades include new enlarged garage doors, an upgraded roof, new 6" gutters, newly insulated garage, updated garage flooring, along with other interior improvements you will have to see. The lower-level workroom is an incredible bonus, an ideal space for tuning skis, working on bikes, tackling projects, or enjoying your favorite hobby with access to the back yard. Outside, the expansive yard offers plenty of room to relax, entertain, garden, and enjoy the peaceful surroundings. Enjoy country-like space while remaining conveniently close to Verona, Middleton, Madison, shopping, dining, and everyday amenities. Beautifully maintained, extensively updated, and ready to enjoy!

7744 Pamela Cir, Middleton

5019 Sawgrass Ter, Middleton
$774,900
4 Beds ⋅ 4 Baths ⋅ 2030720 MLS ⋅ ACTIVE Status
Beautiful custom home in sought-after Bishops Bay offering 4+ bedrooms, 3.5 baths, and 4,000+ sq ft of finished living space. Bright, open floor plan features engineered wood floors and floor-to-ceiling windows. Gourmet kitchen includes granite counters, tile backsplash, Wolf range, new LG appliances, and custom walk-in pantry. Primary suite boasts golf course views, custom closet, and spa-like bath. Three additional bedrooms, dual-vanity bath, and main level laundry. Finished lower level offers rec room, full bath, and flexible bonus space. Enjoy the fenced yard and maintenance free porch. New roof prior to closing! Bishops Bay amenities include pool, fitness center, trails, and more. Golf available through Bishops Bay Country Club membership.

5019 Sawgrass Ter, Middleton

3412 Valley Ridge Rd Unit 4, Middleton
$299,900
3 Beds ⋅ 2 Baths ⋅ 2030645 MLS ⋅ ACTIVE Status
Adjacent to Pheasant Branch Conservancy, this large Middleton 3-bedroom, 2 full baths, updated condo could be all yours! Surrounded by Cedar Trees, with a ground-level patio offering lush greenery & privacy. Great common space w/ a Gazebo, Warm underground parking, private storage unit, & large storage locker. Water Softener and Filters maintained by Maintenance; this unit has extra storage, including its own washer & dryer. Full Kitchen Remodel, floor plan has been opened up, newly remodeled & designed for efficiency, easy living, & lots of natural light throughout! See list of improvements in Associated Docs. This building is well cared for by its association; owners have gratitude for the beautiful community found here. Easy Access to Downtown Middleton/Madison. Bus Stops at Driveway. Easy access to hiking and biking in Pheasant Branch. Short walk to Lake Mendota & Mendota County Park. Located a few blocks from Dane Co. best restaurants & Shops. Dues include high-speed internet

3412 Valley Ridge Rd Unit 4, Middleton

6604 Linnet Ln, Middleton
$638,900
4 Beds ⋅ 3 Baths ⋅ 2030577 MLS ⋅ ACTIVE Status
Located in the heart of the highly sought-after Middleton School District, this stunning 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, space & functionality. Step in to a welcoming spacious living area w/ charming fireplace perfect for relaxing evenings. The open layout flows seamlessly into the kitchen & dining area, w/ ample counter space & room to gather. Versatile flex room on the main level. A generous primary suite w/ box tray ceiling, ensuite bath and walk-in closet, plus 3 additional bedrooms all with walk in closets, and a full bath. A second large flex room on the upper level offers endless possibilities. An egress window in the lower level allows for potential for a future finished basement. Plenty of space in the 3 car garage. Don't miss out on this Middleton gem! December completion

6604 Linnet Ln, Middleton

6610 Linnet Ln, Middleton
$634,900
4 Beds ⋅ 3 Baths ⋅ 2030576 MLS ⋅ ACTIVE Status
Energy Efficient New Construction located in the highly sought after Middleton School District. Tim O'Brien Homes Abbott plan welcomes you from the covered front porch inviting you into an open living space where the bright sunny Great Room features a cozy fireplace & is open to a spacious Kitchen and dining area. The quartz counters & ample cabinetry make this kitchen a chef's dream. A Flex Room is located off the main living & provides a quiet area perfect for an office or formal dining. In the expansive upper level find 4 bedrooms including the impressive Primary Suite w/ box tray ceiling, a large walk-in closet & luxurious bath w/ tile shower and bench. An additional flex room on the upper level offers endless possibilities. An egress window in the lower level allows for future potential finished basement. Plenty of room in the 3 car garage. Don't miss this Middleton gem! December completion

6610 Linnet Ln, Middleton

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