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

L233 Towhee Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L247 Thrasher Street, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L250 Thrasher Street, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L244 Hooded Merganser Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L253 Thrasher Street, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L238 Hooded Merganser Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L235 Towhee Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L206 Hooded Merganser Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L207 Hooded Merganser Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L210 Hooded Merganser Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

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

L208 Hooded Merganser Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$365,000
3 Beds ⋅ 1 Baths
Don't miss this adorable single-level ranch on Madison's Northside! Original hardwood floors, vintage accents, and authentic bathroom tile give this 1958 home so much character, while major updates mean you can move right in worry-free: brand NEW FURNACE (2026), brand NEW ROOF (2026), newer windows, and exterior paint. While offering 3 bedrooms, 1 bath, and an unfinished basement (+ surprise room) leaving room to expand and make it your own! All appliances stay including the washer and dryer. Outside, enjoy a lovely backyard (.20 acre +/- lot) and an oversized 2+car detached garage!!! Location is everything here: you're minutes from Northside neighborhood favorites like Zippy Lube, Lola's, Bear & Bottle, Willy St Coop, and Ancora, PLUS the beloved Northside Farmers Market on Sundays and numerous parks just minutes to downtown Madison, the airport, lakes, and more! This is Northside living for a price worth checking out! You've got to see this one!

1710 Thackeray Road, Madison

Listing courtesy of RE/MAX Preferred.

$579,000
1920's Spacious Shorewood Brick Duplex with formal dining rooms, Sun rooms, archways, fireplaces, Hardwood Floors and 3 car garageGreat location within walking distance of Atwater Beach, play ground, Tennis courts, cafe and more.Seller had sewer redone and lined to the Main.Call to see this one today.

4155 N Farwell Avenue Unit 4157, Shorewood

Listing courtesy of Milwaukee Executive Realty, LLC.

$450,000
3 Beds ⋅ 2.5 Baths
Showings start July 28th. Move right into this beautiful 2-story home in McFarland! A quick drive to the Beltline & 10 minutes to downtown Madison's restaurants, entertainment & shopping. Elegant cherry hardwood floors throughout main level. Kitchen shines with quartz countertops, stainless steel appliances, a large island, & designer herringbone tile backsplash. Main floor also offers a stylish powder room with wainscoting & a functional laundry/mudroom complete w/ decorative tile flooring, subway tile backsplash, custom built-ins, & direct access to an oversized 2-car garage with epoxy-coated floor. Upstairs you'll find three bedrooms, including a spacious primary suite w/ a walk-in closet & updated bath featuring a tiled walk-in shower. Full basement offers abundant storage or future finishing potential. Enjoy the fully fenced backyard and extended deck?perfect for relaxing or entertaining. New Windows, patio door, & refrigerator ('25). Deck ('23). Stove, Microwave, Toilets ('22).

4514 Catalina Parkway, Madison

Listing courtesy of First Weber Inc.

$800,000
3 Beds ⋅ 2.5 Baths
Vintage charm meets mid-century modern in this beautiful home nestled in the highly sought-after Sunset Hills neighborhood. Offering 3 beds, 2.5 baths, & 2,000 sq ft of living space, this home is filled w/ character and thoughtful updates throughout. The main level features vaulted ceilings, a cozy gas fireplace, & an abundance of natural light. Upstairs, you'll find 3 bedrooms & a full bath. The walkout LL provides a living room w/ direct access to the backyard, along with ample storage & a versatile bonus room ideal for a home gym, hobby space, or workshop. Enjoy outdoor living from the screened porch & adjoining stamped concrete patio, both overlooking a private, fenced backyard surrounded by mature trees and lush landscaping. Recent improvements include the roof, windows, water heater, water softener, paint, flooring,& more, providing peace of mind for years to come. Ideally located w/in walking distance of Hoyt Park, downtown Madison, Hilldale Shopping, biking & restaurants.

117 Alden Drive, Madison

Listing courtesy of Pinnacle Real Estate Group LLC.

$787,000
4 Beds ⋅ 1.5 Baths
Showings begin 7/30. The personal home of Hiawatha Circle developer Tom McGovern, this Frank Lloyd Wright-inspired mid-century residence offers the ease of true one-story living. Walls of windows fill the home with natural light, connecting the interior to the expansive double lot overlooking the distinctive central green of Hiawatha Circle Park. Original mahogany woodwork, hardwood floors, flagstone accents, fireplaces, and beautifully proportioned living spaces reflect timeless craftsmanship. Thoughtfully stewarded with energy-conscious improvements honoring its original character. Enjoy the screened porch, brick patio, mature fruit and shade trees, native gardens, and abundant birdsong. Just moments from the UW Arboretum, bike paths, Sequoia library, Monroe Street, Hilldale, and neighborhood schools. A rare home where architecture, nature, and community come together in a neighborhood where the annual Hiawatha Circle picnic has celebrated belonging for generations.

25 Hiawatha Circle, Madison

Listing courtesy of Latitude Regenerative Real Estate.

$569,900
2 Beds ⋅ 2 Baths
ENJOY CAPITOL VIEWS FROM YOUR BALCONY! Lovely corner unit on the 8th floor of Capitol West. Highly coveted 2 bedroom, 2 bathroom unit w/ an open floor plan, gleaming wood floors, cozy fireplace in the living room, & large balcony beckoning you to dine alfresco. The well-appointed chef's kitchen has granite countertops, breakfast bar, & new induction stove. In unit laundry right off the kitchen for convenience. The split bedrooms provide privacy in the primary suite w/ expansive windows & gorgeous views of the city. The ensuite bathroom has tile floors, double sinks, granite top vanity & large tub perfect for soaking. The 2nd bedroom is full of natural light w/ large windows. The 2nd full bath has tile floors & granite vanity top. 1 heated parking space, 1 storage unit, & fitness center all included! Stroll to the Farmer's Market on Saturday mornings, Concerts on the Square on Wednesdays, and never miss a beat of all that downtown Madison has to offer!

309 W Washington Avenue Unit 801, Madison

Listing courtesy of Keller Williams Realty.

$6,850,000
This exceptional 65,000-square-foot industrial facility is ideally situated in the heart of Middleton Business Park, offering a premier location with outstanding functionality. Designed to accommodate a wide range of business operations, the property features private offices, two conference rooms, a spacious cafeteria, multiple loading docks and overhead doors, a modernized warehouse, and ample on-site parking. Meticulously maintained inside and out, the building and grounds reflect pride of ownership and are move-in ready for their next occupant.

2410 Parview Road, Middleton

Listing courtesy of Collective Real Estate Group.

$474,900
3 Beds ⋅ 2.5 Baths
Showings start 7/31. Nestled in sought-after Brentwood Village sit this gorgeous home built in 2006, surrounded by nature w/lush perennial gardens, raspberries, herbs & vegetable gardens backing up to golf course where you can XC Ski right out your backdoor in winter! Main floor boasts solid wood floors, warm woodwork & sunshine w/open floor plan that's excellent for entertaining w/living room centered around a cozy gas fireplace, open dining/kitchen leading you to the huge deck overlooking the stunning backyard. Excellent workspace in the beautiful kitchen w/pantry, new Bosch dishwasher and an island/breakfast bar. Primary bedroom w/full ensuite bathroom and walk-in closet is a rare find! Generous room dimensions & incredible basement w/8ft + ceilings, new flooring & plumbed for future bathroom. Priced under assessed value & loaded w/updates including Roof, RO System, washer, H20 Softener & More. Commuters dream: Bike to UW, Public Market & all the fun things Madison has to offer!

1438 Sheridan Drive, Madison

Listing courtesy of Lauer Realty Group, Inc..

$599,900
4 Beds ⋅ 2.5 Baths
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 Drive, Middleton

Listing courtesy of MHB Real Estate.

$455,000
3 Beds ⋅ 2 Baths
Move in and immediately enjoy living in this well-maintained ranch in Sauk Creek neighborhood walking distance to park and easy drive to shopping and dining. Beautiful painted cabinets with updated hardware, quartz counter tops, backsplash, newer appliances and kitchen flooring. Added bonus of a cozy dinette & with coat hooks and shoe cubbies bench, conveniently located off attached garage. All of this combined with a spacious living room with fireplace offer versatility for different lifestyles. Brand new roof and rain gutters 2026; furnace & AC 2021, water heater 2025, water softener 2020. Lower level family room was finished in 2020, with plenty of room remaining for home gym, office and storage. Basement refrigerator stays along with washer & dryer. Other updates include the primary bedroom bathroom with tiled walk-in shower and patio off dining room. Mature landscaping and extra deep 2-car garage. Quick closing is possible!

118 N High Point Road, Madison

Listing courtesy of First Weber Inc.

$1,120,000
Located on Madison's thriving east side, Freedom Park Apartments offers investors the opportunity to acquire a well-positioned multifamily asset in a high-demand rental market. Surrounded by established neighborhoods and just minutes from major employers, shopping, restaurants, and everyday conveniences, the property is ideally situated to attract and retain quality tenants. The community consists of thoughtfully designed 1-bedroom, 1-bathroom apartments that appeal to a broad tenant base, including young professionals, students, and individuals seeking low-maintenance living. Efficient layouts and an excellent location contribute to consistent rental demand and long-term occupancy potential. With its strong market fundamentals, desirable location, and wide-ranging tenant appeal, Freedom Park Apartments presents an outstanding investment opportunity for buyers seeking stable cash flow and future appreciation in one of Madison's most established residential areas.

3802 Lien Road, Madison

Listing courtesy of Patriot Properties.

$750,000
3 Beds ⋅ 3.5 Baths
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 and snow removal are handled for you, creating more time to enjoy the neighborhood?s cafes, restaurants, shops, and 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, this home pairs everyday convenience with a connected, walkable lifestyle. New Roof+Gutters-2026, New HVAC-2025

6750 Frank Lloyd Wright Avenue, Middleton

Listing courtesy of Sprinkman Real Estate.

$750,000
3 Beds ⋅ 3.5 Baths
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 and snow removal are handled for you, creating more time to enjoy the neighborhood?s cafes, restaurants, shops, and 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.

6750 Frank Lloyd Wright Avenue, Middleton

Listing courtesy of Sprinkman Real Estate.

$329,900
2 Beds ⋅ 1 Baths
Nestled into the lovely Morningside Heights neighborhood on Madison?s East side, just a stone?s throw from everything off Stoughton Rd, Buckeye and Monona, is this quaint 2 bedroom, 1 bathroom ranch that?s bigger than it looks! With almost all the heavy lifting done, you can move right in and enjoy. Features an open concept living-dining-kitchen w/ stainless appliances, farmhouse sink, exposed brick, kitchen island w/ breakfast bar and gorgeous white subway tile with black accents. Front porch was previously converted into an office/den with tons of storage. Bathroom + lower level flooring just replaced July 2026! Lower level has family room, rec room and laundry. Out back has a spacious shaded and paved patio, raised garden beds and 1.5+ car garage. Per the property records: furnace 2022, roof 2009, water heater 2018, AC/windows/siding 2012. It?s time to enjoy this established neighborhood with beautiful mature trees in the heart of all the city?s east side. Make this house your home!

4513 Rahel Street, Madison

Listing courtesy of Realty One Group Luminous.

$3,750,000
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 Road, Middleton

Listing courtesy of First Weber Inc.

$375,000
3 Beds ⋅ 1 Baths
Welcome home to this charming 3-bedroom ranch in an ideal central Madison location! Filled with warmth and character, this inviting home features beautiful hardwood floors and fresh paint throughout the main level, creating a bright, move-in-ready space. The functional layout offers comfortable everyday living, while the stunning three-season porch with all-vinyl windows overlooks the spacious backyard?perfect for relaxing or entertaining. The unfinished basement includes an egress window, offering endless possibilities to add future living space, a home office, gym, or simply enjoy abundant storage. A new HVAC system installed in 2026 provides added comfort and peace of mind. Conveniently located main level laundry, attached 2 car garage, and a great location near parks, shopping, restaurants, schools, and downtown Madison. This home offers the perfect blend of charm, potential, and location!

5509 Raymond Road, Madison

Listing courtesy of MHB Real Estate.

$574,900
3 Beds ⋅ 2 Baths
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.

6679 Redpoll Road, Middleton

Listing courtesy of Encore Real Estate Services, I.

$1,149,000
A rare opportunity to own one of renowned Milwaukee architect, Thomas Van Alyea's masterpieces along this elegant stretch of Downer Avenue. This meticulously maintained property will delight the most discerning buyer. Both the upper and lower units feature original detailing such as coved ceilings, arched doorways, burnished original hardwoods, hand-palmed plaster, and gorgeous leaded-glass windows. You'll appreciate the thoughtfully renovated kitchen and the 2 full BA in the 3 BR 1st floor unit. Heading upstairs, you can choose between the graceful circular stair, or the fully functional elevator that services the lower level, and 1st and 2nd floors. The 3BR 2BA upper boasts a beautifully updated kitchen and primary bath, a gorgeous deck, as well as an additional 3BR and 2 BA 3rd floor!

4143 N Downer Avenue Unit 4145, Shorewood

Listing courtesy of Keller Williams Milwaukee North Shore.

$439,900
2 Beds ⋅ 2 Baths
Welcome home to this beautiful private end-unit condo on Madison's highly desirable West Side! Offering 2 bedrooms, 2 full baths, and a spacious loft, this home features an open-concept layout designed for both comfortable everyday living and effortless entertaining. The inviting kitchen features a large center island, open to the bright living and dining areas. Enjoy your morning coffee or unwind at the end of the day from the screened porch or adjoining private deck. The versatile loft provides the perfect space for a home office, or guest retreat. The heated attached garage offers exceptional convenience with ample storage, plus an additional dedicated storage room for all your extras. Ideally located near shopping, dining, parks, bike paths, and everything Madison's West Side has to offer, this move-in-ready condo combines comfort, privacy, and an unbeatable location.

3160 S High Point Road, Madison

Listing courtesy of MHB Real Estate.

Copyright 2026 WIREX Multiple Listing Service. 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 prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.