Refine Search
Sort by
7746 Maas Dr, Middleton
$750,000
4 Beds ⋅ 3 Baths ⋅ 2035130 MLS ⋅ ACTIVE Status
Welcome home to this custom-built Cherrywood home offering 4,391 square feet of finished living space and room to gather, unwind, and make it your own. A lovely home with recent improvements; including a new roof, new siding, & new appliances to name a few - added confidence as you consider your next move. The spacious, traditional floor plan features a formal dining room and a separate sitting room, with large windows bringing beautiful natural light into both spaces. In the great room, custom built-ins and a cozy fireplace create an inviting place to relax, while the adjoining sunroom offers tiled floors and a bright setting to enjoy throughout the day. Upstairs, the generously sized primary suite provides a comfortable retreat. Also, the basement space offers possibilities for a future recreation room, workout area, or home theater. Outside, enjoy a large backyard with space to entertain, garden, or simply relax. A three-car attached garage is an added bonus!

7746 Maas Dr, Middleton

6713 Gaylord Nelson Rd, Middleton
$849,900
4 Beds ⋅ 4 Baths ⋅ 2035088 MLS ⋅ ACTIVE Status
Presenting the perfect home in Middleton Hills. 4-bedrooms, 3.5 baths, open floorplan, formal and informal dining, fabulous kitchen, office area, family room, craft room, and expansive 3-car garage with no steps into the house! The original owners relocated and everything was updated – stunning refinished hickory floors throughout main level; all carpeting replaced; every inch repainted inside; new stove and dishwasher; outside repainted; new roof; landscaping; includes an Ultimate UHP Home Warranty. All you need to do is move in. Access to the Pheasant Branch Conservancy is one block away. A grocery store, restaurants, and retail are all at the entry of the Middleton Hills neighborhood. Don’t wait to seize this opportunity to own this fabulous property at an exceptional value!

6713 Gaylord Nelson Rd, Middleton

7842 Big Timber Trl, Middleton
$939,000
4 Beds ⋅ 4 Baths ⋅ 2034964 MLS ⋅ ACTIVE Status
Custom home in a beautiful setting, Enchanted Valley Estates and Middleton-Cross Plains schools. Live with the convenience of a subdivision on a cul-de-sac but in privacy of the nature. More than 4,000 sq ft provides not only personal space, whether it need be for work or play, but warm gathering areas to share life. Newly refinished floors in kitchen and entry. Formal dining room with bar. Great room with gas fireplace, parquet floors and picture window views across the pool to the valley. Additional Great Room with wood-burning fireplace and windows overlooking the forest. Hot Tub room with fireplace. Built in cabinets throughout the home. Multiple decks. Walk-out lower level to pool in-ground pool. House and decks are newly painted. 4.5 car garage. Lower bedroom is equipped as an efficiency if desired as such. Acreage and Tax information is for both parcels 0708-062-0067-7 and 0708-062-0850-8. Buyer to verify s.f. and room dimensions if important. No sign on property.

7842 Big Timber Trl, Middleton

5019 Sawgrass Ter, Middleton
$4,000
4 Beds ⋅ 4 Baths ⋅ 2034764 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. Bishops Bay amenities include pool, fitness center, trails, and more. Golf available through Bishops Bay Country Club membership.

5019 Sawgrass Ter, Middleton

4029 Serenbe St, Middleton
$1,499,000
2034690 MLS ⋅ ACTIVE Status
Experience this elevated, move-in ready home in Middleton. The main level is anchored by two first-floor bedroom suites and a seamless connection between kitchen, dining, and den, with hardwood floors, a wood-burning fireplace, and SubZero, Wolf, and Cove appliances. All bedrooms in the main home feature en suite baths, offering comfort and privacy throughout. Above the garage, a separately accessed 1 bed, 1 bath apartment provides unique flexibility for multigenerational living, guests, extended stays, or a private workspace. Solar, geothermal heating and cooling, and a metal roof offer long-term energy efficiency and resiliency. HOA-managed landscaping and snow removal support a true lock-and-leave lifestyle.

4029 Serenbe St, Middleton

4029 Serenbe St, Middleton
$1,499,000
5 Beds ⋅ 6 Baths ⋅ 2034688 MLS ⋅ ACTIVE Status
Experience this elevated, move-in ready home in Middleton. The main level is anchored by two first-floor bedroom suites and a seamless connection between kitchen, dining, and den, with hardwood floors, a wood-burning fireplace, and SubZero, Wolf, and Cove appliances. All bedrooms in the main home feature en suite baths, offering comfort and privacy throughout. Above the garage, a separately accessed 1 bed, 1 bath apartment provides unique flexibility for multigenerational living, guests, extended stays, or a private workspace. Solar, geothermal heating and cooling, and a metal roof offer long-term energy efficiency and resiliency. HOA-managed landscaping and snow removal support a true lock-and-leave lifestyle.

4029 Serenbe St, Middleton

6817 South Ave, Middleton
$599,900
2 Beds ⋅ 2 Baths ⋅ 2034624 MLS ⋅ ACTIVE Status
Don't miss out on the opportunity to be the third-ever owner of this beautiful Middleton gem. This beautiful, easy-to-show, lannon-stone home features rich original hardwood floors, with pristine trim, built-in cabinetry, updated kitchen, and room to grow both up and down. Large living room with gas fireplace, two spacious bedrooms with plenty of closet space combine charm and comfort. Large kitchen and separate dining area. The location is unbeatable - situated on a quiet street within walking distance of parks, schools, Middleton Public Library and Downtown Middleton. It's truly a must-see. This home has "great bones" and features an unfinished, walk-up attic and unfinished basement which provide room for expanded living area. All this home needs is your cosmetic touches. Stackable washer and dryer on the main level are included in the sale. Please exclude washer and dryer in basement level. Sellers have not used fireplace. Listing agents are related to Sellers.

6817 South Ave, Middleton

3861 Bay Laurel Ln, Middleton
$979,900
5 Beds ⋅ 5 Baths ⋅ 2032270 MLS ⋅ ACTIVE UNDER CONTRACT Status
SPRUCE HOLLOW - This 5 bedroom, 4.5 bath two story home on a 3/4 acre lot is exceptional! BRAND NEW ROOF in August, 2026. Fresh interior and exterior paint in September, 2026. The homes open floor plan features engineered hardwood flooring, a GR w/built-ins & gas fireplace. Kitchen features a huge quartz island w/ breakfast bar, subway tile backsplash & SS appliances. Four sizable bedrooms upstairs including a primary with WIC, double sinks & large bathroom. Main level office with french doors (perfect for working from home) & a finished basement with 5th bedroom, full bath, exercise room & playroom! Enjoy mornings and evenings on the deck or enclosed screen porch! 3 car garage! Middleton Schools... Enjoy Spruce Hollow Park less than 500 yards away! Multiple nearby walking trails and ponds to enhance daily activities. 10 minutes from Epic's campus and 18 minutes to UW Hospital. UHP Ultimate Home Warranty Included. Town of Middleton taxes! This one will not last long!

3861 Bay Laurel Ln, Middleton

7544 Blue Cedar Dr, Middleton
$1,749,000
4 Beds ⋅ 4 Baths ⋅ 2034402 MLS ⋅ ACTIVE Status
2026 Parade of Homes stunner by Victory Homes of Wisconsin! Thoughtfully designed with elevated finishes and incredible attention to detail, this home features a dramatic vaulted great room with exposed wood beams, walls of windows and a sleek fireplace. The chef-inspired kitchen offers an oversized island, abundant cabinetry and an impressive walk-in pantry. A dedicated office with a striking statement ceiling, spacious primary suite with spa-like bath, and beautifully appointed laundry room add both style and function. The finished lower level is made for entertaining with a full wet bar, expansive family/rec space and dedicated exercise room. Warm wood tones, custom details and distinctive architectural elements carry throughout this exceptional Parade home.

7544 Blue Cedar Dr, Middleton

2809 Century Harbor Rd Unit 3, Middleton
$239,900
1 Beds ⋅ 1 Baths ⋅ 2034363 MLS ⋅ ACTIVE Status
OPEN HOUSE SUNDAY 10/11 12pm-2pm! 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

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, & Bus line.

3414 Valley Ridge Rd Unit 3, Middleton

7017 Prairie Dr, Middleton
$474,900
3 Beds ⋅ 2 Baths ⋅ 2033718 MLS ⋅ ACTIVE UNDER CONTRACT 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 mechanical updates including a '12 A/C, '04 furnace, and '17 water heater & new roof soon! 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

7237 Lily Ln, Middleton
$899,900
3 Beds ⋅ 3 Baths ⋅ 2033288 MLS ⋅ ACTIVE UNDER CONTRACT Status
Step into easy, upscale condo living with exceptional attention to detail throughout. The main level features a showstopping quartz island and backsplash, upgraded cabinetry, KitchenAid stainless appliances, cooktop and hood vent, and an open layout connecting the kitchen, dining and living areas. Wide arches, hardwood floors and thoughtful finishes add timeless appeal. The primary suite offers a private bath with quartz vanity, tiled shower with bench and a walk-in closet with built-ins. A flexible office/2nd bedroom, full bath and convenient laundry room with washer/dryer and folding counter complete the main level. Enjoy a maintenance-free deck overlooking Graber Pond and Conservancy/walking path. The finished lower level adds a 3rd bedroom with built-ins, full bath, game room w/wet bar, rec room with fireplace and game area, plus a dedicated office/wine display room with cellar. A rare combination of style, space and functionality; just a short walk to Pheasant Branch Conservancy!

7237 Lily Ln, 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

8773 Airport Rd, Middleton
$839,900
4 Beds ⋅ 3 Baths ⋅ 2033282 MLS ⋅ ACTIVE Status
Tucked away on 8.86 private acres in Middleton, this 4 bed, 3 bath home offers a rare combination of space, privacy, and convenience. Surrounded by trees in a peaceful natural setting, the property feels secluded while providing easy access to Middleton, Madison, shopping, dining, schools, and everyday amenities. The property is zoned AT-5 , offering opportunities for agricultural uses such as horses or other livestock, gardening, and more, subject to applicable local requirements. Inside, you’ll find over 2,500 finished square feet with spacious living areas, a wood burning fireplace, screened porch, and a partially finished walkout lower level offering additional living and office space. An attached 2 car garage plus a detached garage provides excellent room for vehicles, equipment, hobbies, or storage. Whether you’re looking for room for horses, a hobby farm, or simply more land and privacy, the opportunities here are endless.

8773 Airport Rd, Middleton

7410 W Old Sauk Rd, Middleton
$649,000
2033249 MLS ⋅ ACTIVE Status
This is a rare opportunity to BYO builder to this beautiful 1.57-acre homesite in the Town of Middleton, adjacent to Blackhawk in the Middleton-Cross Plains School District. Framed by mature trees that offer outstanding privacy, the property opens to a spacious building envelope ready for your dream home. Enjoy the tranquil feel of country living w/ convenient access to Middleton & West Madison's amenities. Walk to the 105-acre Pope Farm Conservancy & to Pope Farm Elementary. SFR-08 zoning allows for outbuildings, so it's time for that shop, toy storage, or hobby space you've always wanted. Improvements incl a shared driveway, 2-car garage (new roof 2023), electric & phone to back of lot & private well. Natural gas avail across Old Sauk Rd. 2016 soil test previously approved for conventional septic. Parcels of this size, in this location, rarely become available, so don’t miss your chance to make it yours & build something truly special. Property & all improvements being sold As-Is.

7410 W Old Sauk Rd, Middleton

6619 Cooper Ave, Middleton
$459,000
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 two additional units. The refreshed lower level offers versatile space for a rec room, home office, workout area or additional living space. Outside, enjoy a spacious backyard with plenty of room. 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

7205-7207 University Ave, Middleton
$549,900
2033134 MLS ⋅ ACTIVE Status
SELLER OFFERING $10,000 FOR RATE BUY DOWN! New roof as of 10/1/2026! A fantastic opportunity to own a well-maintained two-flat in a convenient Middleton location! Whether you’re looking to expand your investment portfolio or live in one unit while renting the other, this property offers flexibility and long-term potential. 7207 includes a remodeled kitchen completed in 2022, along with original hardwood floors and exceptional character and storage. 7205 features 3 bedrooms on the upper level with exceptional attic storage, updated windows and newer furnace/AC. Additional improvements include a newer water softener. The large unfinished basement offers additional shared storage space as well as on-site laundry. Located near historic downtown Middleton, parks, schools, shopping, dining, and easy access to Madison. Additionally, there is a public walking path giving access to Franklin Ave for street parking. A versatile property in a highly desirable area—ready for its next owner!

7205-7207 University 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

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.

How much is your home worth?

Get instant property value now!