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$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

$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

$859,900
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. New Roof and Furnace. Price reduced $40,000

7226 Hubbard Ave, 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

$399,999
2 Beds 2 Baths 2026790 MLS ACTIVE Status
Light, bright & spacious 2BR/1.5BA condo in desirable Woodridge Condo Community with vaulted ceilings, 2 stories of windows, beautiful wood floors, skylights, tranquil back deck overlooking Pheasant Branch Conservancy and an open plan ideal for everyday living. Gas Fireplace. Some updates include refrigerator, Microwave and Oven/Range-2024, Garbage Disposal-2020, New Window in loft- 2023, New Toilets in both baths-2026, New Water Heater--aprox. 2023. Enjoy green space and bordering Pheasant Branch Conservancy for walking, biking, wildlife & serenity. Convenient Middleton location close to shopping, restaurants and quick access to the Beltline. Beautifully maintained, move-in ready — a rare find!

7305 Donna Dr, Middleton

$1,690,000
5 Beds 5 Baths 2026810 MLS ACTIVE Status
Exceptional custom home offering luxurious finishes & thoughtful design throughout. The stunning great room features a floor-to-ceiling fireplace flanked by custom built-in shelving. A chef's kitchen boasts a large center island, 6-burner range w/ griddle, expansive walk-in pantry, & seamless flow into the dinette, complete w/ a wine bar, beverage refrigerator drawers, & wine cooler. Enjoy year-round entertaining on the screened porch w/ a fireplace & adjoining maintenance-free deck. The main level includes a private office w/ French doors & built-in cabinetry, plus a second office or flex room. Upstairs, the spacious primary suite offers a double vanity, soaking tub, & tiled shower, along w/ convenient second-floor laundry. Two bedrooms share a Jack-and-Jill bath, the third bedroom features private baths. The finished walkout lower level includes family room, a wet bar, bedroom, full bath, & access to the backyard. Completing the home is an oversized 3-car. Overlooks Pioneer Pointe.

7616 Tumbledown Trl, Middleton

$649,900
2026259 MLS ACTIVE Status
Live in one half, let your tenant cover the rest. This classic two-story duplex sits in the heart of Middleton, and with a newly signed lease at $2,000/month already in place, the mortgage math works from day one. The owner's side (3207) lives like a true single-family home—3 bedrooms, 1.5 baths, and a 1-car garage, freshly updated with stainless steel appliances, a renovated bathroom, fresh paint throughout with crisp white trim, brand-new carpet upstairs, and a living room fireplace made for cozy Wisconsin evenings. Next door, (3209) is turnkey for your tenant: 2 bedrooms, 1.5 baths, and its own 1-car garage, with newer LVP flooring, an updated kitchen, and updated bathrooms. All of it just minutes from schools, shopping, and parks. Whether you're a first-time buyer looking to offset your payment or an investor after a low-maintenance property in one of the area's most desirable communities, this is a rare chance to make a smart move in Middleton. Updated Windows Both Units!

3207-3209 Patty Ln, Middleton

$1,445,000
5 Beds 5 Baths 2024433 MLS ACTIVE UNDER CONTRACT Status
Set on a beautiful 0.92-acre lot, this home offers timeless architecture, refined finishes, and thoughtful updates in one of the area’s most exclusive neighborhoods. The home features 5 bedrooms, walk-in closets, 4 full baths, and a main level powder room, with a finished lower level filled with natural light. Brazilian cherry floors, exquisite ceilings, custom millwork, and built-in bookshelves showcase the exceptional craftsmanship throughout. The library offers a gas fireplace, while the family room provides a welcoming gathering space that opens to the outdoors. The custom kitchen is appointed with Sub-Zero and Wolf appliances, including a four-burner gas stove with griddle, beverage refrigerator, maple and cherry cabinetry, a butler’s pantry, and reverse osmosis filtration. Outdoor living is enhanced by Trex decking added in 2026. Additional highlights include a 3-car garage, security system, central vacuum, new HVAC (2023), new water heater (2024), & new washer and dryer (2024).

4516 Nina Ln, Middleton

$1,299,000
2026912 MLS ACTIVE Status
Under construction, estimated completion mid July 2026. Welcome to this thoughtfully designed home at Belle Farm offering main level living with a private primary suite and an open concept kitchen, living, and dining area. The living space is light-filled & functional, with hardwood floors, wood-burning stove, and a well-appointed kitchen featuring Sub-Zero, Wolf and Cove appliances. Above the garage, a separately accessed 1 bed, 1 bath apartment space provides flexibility for a caregiver, guests, extended stays, multigenerational living, or a home office. Lower level includes additional bedrooms & living space, offering separation and versatility. Built with resilience in mind, the home includes solar, geothermal HVAC, and is wired for EV charging. HOA covers lawn care and snow removal, making ownership low-maintenance and easy for travel.

4057 Morning Poem Pl, Middleton

$1,499,900
5 Beds 5 Baths 2026869 MLS ACTIVE UNDER CONTRACT Status
Experience luxury living in Middleton’s coveted Summit Pass neighborhood, where breathtaking views, exceptional craftsmanship, and timeless elegance come together. The main level showcases a dramatic two-story great room with floor-to-ceiling windows, a striking fireplace, gourmet kitchen, wet bar, inviting outdoor entertaining space, and an expansive primary suite designed for comfort and privacy. Upstairs offers three spacious bedrooms, a flexible den, and two full baths. The finished lower level is an entertainer’s dream with a generous rec room, full bar, wine cellar, theater room, full bath, and fifth bedroom ideal for overnight guests. A stately home office, private fitness room, abundant storage, and oversized heated three-car garage complete this exceptional home at 4498 Nina Lane.

4498 Nina Ln, Middleton

$999,900
4 Beds 3 Baths 2026028 MLS ACTIVE Status
What sets this incredible property apart is clear before you even step inside. This contemporary home is surrounded by carefully tended prairie and woods, a thriving habitat for birds, pollinators, and wildlife. Architect Bruce Nichols designed this home with one intention: to bring the outside in. Floor to ceiling windows and skylights draw natural light deep into the heart of the home. The open kitchen w/pantry and lg island flows easily into the family room and sunny bfast nook, w/hardwood floors throughout. Guest bed + bath on main level w/primary suite + 2 beds/bath up. Glass railing overlooks the 2-story great room w/gas FP. Primary suite is a sanctuary of its own w/gas FP, oversized WIC, and bath w/shower and whirlpool tub. Solar panels, whole house fan, and updated mechanicals. Middleton schools w/low Town of Middleton taxes and nearly 2 acres of seclusion combine to create a package that rarely comes to market. If you’ve been waiting for something truly different, this is it.

8685 Airport Rd, Middleton

$550,000
3 Beds 3 Baths 2024690 MLS ACTIVE UNDER CONTRACT Status
Want Waunakee schools but also something a bit closer to west Madison/Middleton? This sweet cul-de-sac is on the outskirts of Northlake neighborhood. Super short walk Orchid Heights park and to Pheasant Branch Conservancy, with miles of walking paths - a true respite from daily life. This floor plan has some really great features, including a giant mudroom with powder room (not shared with the laundry!), flex space at the top of the stair (office, crafting, reading nook?), a covered patio and 3 car garage. Two adjacent outlots give some nice elbow room between the neighbors behind. Unfinished lower level is loaded with potential for more finished space, with high/flush ceiling and rough-in for a full bath. Just 3 years old and looks brand new.

5344 Magdalene Ct, Middleton

$458,500
3 Beds 4 Baths 2025984 MLS ACTIVE Status
Under construction; estimated completion 8/27/26. Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement INCLUDED. Garage enters at basement level. Shared maintenance agreement means that you’ll never need to worry about snow removal or landscape care--all taken care of for you! Shared maintenance fee also includes your homeowners insurance coverage & your Redtail Ridge Master Homeowners Association fee. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos & tour are of a similar model. Plans & design selections available upon request. END UNIT, INCLUDES FIREPLACE!

6834 Belle Fontaine Blvd, Middleton

$448,500
3 Beds 4 Baths 2025983 MLS ACTIVE Status
Under construction; estimated completion 8/27/26. Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement INCLUDED. Garage enters at basement level. Shared maintenance agreement means that you’ll never need to worry about snow removal or landscape care--all taken care of for you! Shared maintenance fee also includes your homeowners insurance coverage & your Redtail Ridge Master Homeowners Association fee. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos & tour are of a similar model. Plans & design selections available upon request.

6838 Belle Fontaine Blvd, Middleton

$458,500
3 Beds 4 Baths 2025982 MLS ACTIVE Status
Under construction; estimated completion 8/27/26. Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement INCLUDED. Garage enters at basement level. Shared maintenance agreement means that you’ll never need to worry about snow removal or landscape care--all taken care of for you! Shared maintenance fee also includes your homeowners insurance coverage & your Redtail Ridge Master Homeowners Association fee. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos & tour are of a similar model. Plans & design selections available upon request. END UNIT, INCLUDES FIREPLACE!

6842 Belle Fontaine Blvd, Middleton

$1,299,000
4 Beds 4 Baths 2025953 MLS ACTIVE Status
Welcome to this thoughtfully designed home at Belle Farm offering main level living with a private primary suite & an open concept kitchen, living, & dining area. The living space is light-filled & functional, with hardwood floors, wood-burning stove, & a well-appointed kitchen featuring Sub-Zero, Wolf & Cove appliances. Above the garage, a separately accessed 1 bed, 1 bath ADU provides flexibility for guests, extended stays, multigenerational living, a caregiver, or a home office. Lower level includes additional bedrooms & living space, offering separation & versatility. Built with resilience in mind, the home includes solar, geothermal HVAC, & is wired for EV charging. HOA covers lawn care & snow removal, making ownership low-maintenance & easy for travel.

4057 Morning Poem Pl, Middleton

$659,900
4 Beds 3 Baths 2025847 MLS ACTIVE Status
Move-in ready 8/25/26. This Everest home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 4 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.

7119 Johann Farm Rd, Middleton

$669,000
3 Beds 2 Baths 2025170 MLS ACTIVE Status
Price drop 6/23/26. Charming raised ranch in Woodside Heights enclave, just one block from Stricker's Pond, on tree-lined, quiet, well-kept and in-demand neighborhood with downtown Middleton and schools within walking distance. In-ground pool has new liner and heater (2023), slide & stone paved decking. New carpet & paint throughout. Extensive work on landscape. Expansive Great Room has tongue & groove wood vaulted ceiling with recessed lighting, elegant wood floor, gas fireplace and extensive wood shelving & cabinetry, open to bright kitchen with cooktop island and barstool (3 incl with sale) counter for in-kitchen dining and ceramic floor. Generous window views to fully fenced pool/backyard that makes for great entertaining space! AC(07), Roof/gutters (06), H2O Htr (13), Boiler (16), spray foam insulation in attic. New Bosch DW; disposal. Thermador electric cooktop, stainless wall microwave & oven pair. NOTE: Home also available for rent at $3900/mo.

1308 Shirley St, Middleton

$1,450,000
5 Beds 5 Baths 2023786 MLS ACTIVE Status
Nestled in the prestigious Blackhawk neighborhood and located in the highly sought-after Middleton School District, this former Parade of Homes residence showcases timeless elegance, exceptional craftsmanship, and high-end finishes throughout. A dramatic two-story foyer with a handcrafted curved staircase welcomes you into a light-filled interior featuring soaring cathedral ceilings, rich hardwood floors, arched doorways, and five fireplaces. The gourmet kitchen offers premium appliances, expansive prep space, a large island, and butler’s pantry leading to the formal dining room. Each bedroom features its own ensuite bath, while the main-level office offers flexibility as an additional bedroom. Floor-to-ceiling windows highlight the stunning living room, and the luxurious primary suite includes a private fireplace and spa-like bath. The walkout lower level features a theater room, recreation space, and fifth bedroom.

9715 Red Sky Dr, Middleton

$849,900
5 Beds 4 Baths 2025527 MLS ACTIVE UNDER CONTRACT Status
Experience luxury living in Middleton's highly sought-after Bishops Bay community! This stunning 5-bed home offers exceptional space, thoughtful design, & high-end finishes throughout. Hardwood floors welcome you into the open-concept main level featuring a flexible front sitting/dining space, inviting living room with gas fireplace, and a chef's kitchen complete with granite countertops, oversized island, mosaic tile backsplash, stainless steel appliances, pantry, and sunny dinette. Upstairs, 4 spacious bedrooms each boast walk-in closets, including the elegant primary w/ dual walk-in closets, double vanity, soaker tub, and tiled shower! Convenient upstairs laundry adds everyday ease. The finished walkout lower level is built for entertaining with a wet bar, theater room w/ tiered seating, projector and surround sound, electric fireplace, exercise rm, fifth bedroom, and full bath. Enjoy the trex deck & 3-car garage —all in one of Middleton's premier neighborhoods. See docs for more!

5023 Congressional Hl, Middleton

$645,000
3 Beds 4 Baths 2025413 MLS ACTIVE Status
Middleton School District gem!! Enjoy this Town of Middleton Stonebrook Estates 3-bedroom propertunity nestled on nearly .5 acre privacy setting next to a 5-acre park. Look no further if you are looking for room to roam with the 66-acre walking trails/land with opportunities for bike rides to Settlers Park overlooking the local prairie/savanna. The backyard is perfect to work on your 9-iron aim over your vegetable/flower gardens. Soak in nature as you relax on the deck or patio while you fire up the smoker for your favorite BBQ. The inside layout is ideal for quality time together with enough space to focus on your work/projects with privacy. The inviting cook’s kitchen has abundant counter space to cook together or meal prep for the week. Abundant storage not only in the kitchen but throughout the home. After a fun day in the neighborhood enjoy time to relax in the exposed lower level for games or a movie night. New roof, AC, furnace, appliances, deck.

8600 Ellington Way, Middleton

$1,120,000
4 Beds 4 Baths 2024465 MLS ACTIVE Status
A light-filled, Frank Lloyd Wright-inspired home in desirable Middleton Hills, thoughtfully modernized with updates touching nearly every room. The spacious gourmet kitchen features a Viking range, newer appliances, and abundant workspace. A mudroom addition now connects the garage to the home, adding convenience to everyday living. The finished lower level includes a newly converted fourth bedroom with walk-in closet and adjacent bath. Upstairs, hardwood floors, ceiling fans, custom closet systems, and an expanded tiled primary shower enhance everyday comfort. Enjoy smart home conveniences including HomeKit-compatible locks and garage openers, video doorbells, a smart thermostat, and a Universal EV charger. Outside, a fenced yard, remodeled deck, and newly added paver parking pad create a private retreat for relaxing and entertaining.

3324 Glacier Ridge Rd, Middleton

$599,900
4 Beds 3 Baths 2024641 MLS ACTIVE Status
Under construction; estimated completion 9/29/26. New floor plan! This open concept home designed is designed for modern living! Cook's kitchen includes quartz countertops, granite sink, ceramic tile backsplash, stainless steel appliances, and walk-in pantry. Great room features fireplace & walkout to patio. Flex room for office, playroom, etc and two-story central staircase. Primary bedroom suite includes walk-in closet & private bath with tile shower & dual sinks. Spacious main floor laundry includes 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! Plans & design selections available upon request.

6608 Redpoll Rd, Middleton

$1,949,000
4 Beds 4 Baths 2024407 MLS ACTIVE Status
Imagine coming home to this stunning Twilight Tudor in one of the Madison area’s most desirable communities. With Brio Design Homes in Belle Farm, you get a lot Middleton’s newest development, a 3,625 sq ft concept home design personalized to your needs or custom designed from scratch, in-house interior design, sustainable construction and more. Brio combines design and construction under one roof so you can enjoy a seamless experience and results that truly reflect you. Belle Farm features preserved open space, net-zero construction, intentional connection, and future amenities including a coffee shop, yoga studio, and restaurant. Take advantage of this turn-key new home opportunity and enjoy stunning design and craftsmanship in a one-of-a-kind neighborhood.

7536 California Love Trl, Middleton

$347,719
3 Beds 3 Baths 2021318 MLS ACTIVE Status
$3k credit for closing costs or rate buy-down. Numerous updates; NEW furnace & A/C, water softener, water heater, dishwasher, refrigerator, and washer & dryer! Close in time for start of school! This well-cared-for condo offers spacious, low-maintenance living in a highly desirable Middleton location. The bright, open-concept main level is designed for both everyday living & entertaining, featuring a generous living room w/cozy gas fireplace, a dining area w/access to a private deck, & an updated kitchen; complete w/SS appliances, breakfast bar, & abundant cabinetry. Upstairs, you'll find generously sized bedrooms, including a spacious primary suite w/a WIC & private bath. 2nd bedroom also boasts its own en suite bathroom, while the 3rd bedroom offers flexibility as a home office, fitness room, or addtl living space. Convenient upper-level laundry, a private attached 2-car garage. Ideally located near parks, walking trails, shopping, dining & more! Priced under assessed value.

719 Cricket Ln Unit 1, 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.