353 properties for sale in The Highlands, Madison city Dane County Wisconsin

Your Cul-de-Sac Retreat in Madison! Welcome to your new home, where cul-de-sac living meets comfort and versatility! This 3-bedroom, 2-bath Colonial offers 2,070 sq. Ft. with plenty of space to settle in and make your own. The kitchen features a center island and all-new GE fingerprint-resistant stainless steel appliances, while the gas fireplace creates a cozy gathering spot. A finished basement adds flexible living space, and the deck and patio invite you to enjoy time outdoors. An attached 2-car garage and radon mitigation system complete this inviting Madison home

Southbridge Contemporary is set on a spacious landscaped lot, offering an idyllic location backing up to Bolz Conservancy, and walkable to neighborhood parks, trails and pool. Sun-kissed living w/incredible sunset views on the daily. Main floor offers a large mud room w/ custom built-ins, formal dining w/ french doors that could also make an office, a barrel ceiling bar/pantry feature, & living room w/gas fireplace. Spacious kitchen with cherry cabinetry, granite counters, breakfast bar open to informal dining w/patio doors leading out to the new composite deck. Six bedrooms w/4 bedrooms on the 2nd floor + a 2nd floor laundry room w/cabintery & folding space. Spacious primary suite with walk-in closet, bath with dual vanities, tiled walk-in shower & jetted tub. LL walk-out offering two additional bedrooms, bath, family room w/large stamped concrete patio and screened porch. Oversized three car garage with staircase directly to the basement. Highly ranked schools and community

Enjoy convenient Fitchburg living in this bright and inviting end-unit condo, ideally located just minutes the Beltline and downtown Madison, with the Capital City State Trail nearby. An abundance of windows fills the private entry home with natural light, while the spacious layout offers 2 bedrooms and 2.5 baths. The finished lower level provides valuable additional living space ideal for a rec room, home office, workout area, or guest space. A private 2-car tuck-under garage adds everyday convenience, while nearby community amenities include a pool and fitness center. With plenty of space, great natural light, and easy access to shopping, dining, recreation, and Madison-area destinations, this condo offers an excellent combination of comfort, location, and value

Welcome to this Beautiful 5 bedroom 2.5 bathroom home in the lovely Verona School District. Great location, easily accessible to many amenities on Madisons West Side. This quiet Cul-de-sac with a huge fenced in yard makes for a very peaceful setting! Potential Garden! Hard Wood Floors. Newer Kitchen. Fresh Paint in many rooms! If you have been looking for plenty of space this is the one for you!

Priced below assessment! Bring your vision to this 4-bedroom, 2-bathroom home in Orchard Ridge. Enjoy the privacy of the mature, tree-lined backyard from the large deck, three-season porch, or private ensuite deck. Inside, two fireplaces add character and warmth, while the extra-large garage provides exceptional space for vehicles, storage, hobbies, or a workshop. The spacious lot, mature trees, and multiple outdoor living areas provide a fantastic foundation for creating something special. Conveniently located near schools, parks, Ridgewood Pool, and just a short drive to downtown Madison

Convenient 2 bed/2 bath condo tucked-away in a wooded setting on Madisonâs West Side, just off Gammon Road. Needs some TLC, but bring your ideas and add some instant equity. Open living and dining area features patio doors leading to a private balcony and fills the space with natural light. The primary suite includes a private full bath. One of the larger units in the complex with added office nook. In-unit laundry adds everyday ease, with additional common laundry available. The roof was replaced in 2023. Two underground assigned parking spaces, additional outdoor parking and a private storage unit in the garage area are included. Easy access to the Beltline, schools, shopping, restaurants and bus routes. Two cats permitted; no dogs

Main level 1-bedroom, 1-bathroom with walk-in closet, fireplace, central air, in-unit laundry, tankless water heater, living room patio door leading to covered porch. Intercom security system, below ground parking stall (7207 Flagship Dr P22 (marked L on wall) 070826419-) and storage unit(7207-4). In addition, enjoy the Harbor House Club House, expansive exercise area, swimming pool, sauna, tennis courts, playset and close proximity to commercial and retail developments. Total assessment and taxes reflects additional value of parking stall

First-timers and investors, check out this sweet cream puff! Walk, bike or bus to campus and downtown. And to just about anywhere from this location. Darling bungalow with loads of charm. Beautiful refinished maple floors, vaulted ceiling and classic arch between rooms. So much newness here (most ages unknown): Roof and 2 Skylights, really large Anderson double-hung tilt-in windows, fully fenced back yard with beautiful tall vinyl privacy/security fence, newer furnace, epoxy coating on garage floor, stamped concrete on part of the driveway & part of the pool deck (2024), water softener (2025), light fixtures (2026), kitchen flooring (2026), front door (2026). Delightful right-sized in-ground pool with slide and safety pool cover

Neat, clean, updated floors and windows, move-in ready, ranch-style condo. Floor-to-ceiling west-facing windows and doors bring in wonderful natural light and overlook the beautiful Harbor Village grounds and nearby Pheasant Branch Conservancy. In-unit washer and dryer, fireplace, and den or study off the living room. Underground parking, basement storage, basic cable, pool, tennis courts, and cabana add to the convenience. Pets permitted, subject to association rules

Enjoy the benefits of condo living with the space and feel of a single-family home in this beautiful half-duplex condo nestled alongside Pheasant Branch Conservancy. Enjoy main-level living with your primary bedroom, full bath, laundry, kitchen, dining room, screened in porch, and spacious living room with soaring vaulted ceilings located on the main level. The lower level features a second bedroom, full bath, flex space, and an additional large living area with plenty of natural light. The home just got a major refresh-new carpeting throughout the entire first floor, all old wallpaper removed, and fresh paint throughout the home. Woodcreek Village feels like resort-style living with its private pool, tennis courts, clubhouse, and low-maintenance lifestyle. Lawn care, snow removal, and exterior maintenance are all taken care of by the association, leaving you more time to sip your morning coffee in the screened-in porch while enjoying the peaceful surroundings and wildlife walking by

Well cared for by the original owner, this home has been lovingly maintained and thoughtfully updated over the years. The owner has never had pets in the home, and it shows! Recent improvements include a new deck with a pleasant view overlooking neighboring backyards, shiplap accent walls in the living room and dining room, new living room carpet, a TV wall mount with built-in cabinets, and added organizational cabinets at the mudroom/garage entrance. The primary bedroom features a vaulted tray ceiling with fan and private full bath. The tandem 2 car garage offers plenty of room for vehicles, storage or hobbies. The unfinished lower level includes a 3/4 bath rough-in and offers excellent potential for additional finished living space. Furnace and A/C were recently inspected plus a 1 year home warranty is included providing added peace of mind. A well-maintained home with thoughtful updates, great storage, and room to make it your own!

Exquisite original model home in the coveted West Madison/Verona-mailing enclave, moments from everything the area has to offer. This nearly 2,000 sf residence, crafted in 2017 by Tim O'Brien Homes, showcases premier energy efficiency, solar power, Theater system, an irrigation system, and the exceptional finishes this builder is known for. Thoughtful universal design touches. Wider doorways and a zero-barrier garage entry. Offer effortless aging-in-place living without sacrificing style. Set on a corner lot, the homeowner's skilled landscaping artistry has cultivated lush, elegant landscaping and added a sense of privacy and serenity. A covered patio grilling area that extends the patio, invites sophisticated outdoor entertaining. Sellers are relocating. A rare opportunity awaits. Note: interior photos are original builder images used with permission (excluding primary bath); exterior photos reflect current upgraded landscaping & covered patio. Schedule your private tour today!

Stunning stand-alone condo in desirable Settler Hill within Blackhawk! Grand 2-story entry opens to living room w/ 14' ceilings & floor-to-ceiling stone gas FP. Chefâs kitchen features granite & Quartz counters, white cabinets, SS appls: Bosch induction cooktop, Bosch dishwasher, GE oven, LG fridge, breakfast bar & dinette w/ built-ins. Custom bar w/ copper sink, wine fridge & mini-freezer. Private office w/ floor-to-ceiling built-ins & fireplace. Two spacious primary suites w/ adjoining baths. Sunroom w/ tile floors. Upper level offers loft w/ 3rd fireplace, 3rd bed, full bath & sauna. Exposed unfinished LL provides future expansion potential. ADT security system. 2-car attached garage. Exceptional space & maintenance-free living! Ultimate UHP included

Welcome to this beautifully updated and move-in ready home on Madisonâs desirable west side! Thoughtfully maintained and cared for, this home offers a blend of modern updates, comfortable living spaces, and exceptional outdoor space on a beautifully manicured 0.41-acre lot. The spacious, light-filled kitchen features ample cabinetry, updated appliances, and a dining area overlooking the lush backyard. Hardwood floors add warmth and character to the living room and both main-level bedrooms. The generously sized lower-level primary suite is a true retreat, complete with a tastefully updated bathroom and an oversized custom walk-in closetâa rare and highly desirable feature. Additional lower level space is perfectly set up for a work out area. Another standout feature is the oversized 25' x 24' garage, offering plenty of room for 2 vehicles and the option of a workshop, storage for recreational equipment, or hobbies. Updated windows, freshly painted exterior, EV outlet & more!

This Move-in ready multi-level single house in Madison West Stone Crest Estates subdivision boasts updates, features and convenience! New flooring through out the house in 2026; Modern lighting fixtures in dining & bathrooms, Updated kitchen appliances; Cathedral ceiling in both main floor and in Primary bedroom attracts aboundant natural light & fresh air; Newly installed fence in the large-sized level backyard great for kids' activities and pets; Finished flex room in the basement (18x09) could be an office, a private room for your meditation, relaxation or exercises; Spacious 2-car garage provides addl storage; Short walk to Flagstone Park w/ direct access to Ice Age Trail; Close to all the amenities of Madison far west including Hawk's Landling Golf club, as well as Epic. NO annual HOA fee. Must see to enjoy the house!

A rare opportunity in the heart of Nakoma, this classic Colonial has been cherished by the same family since 1970. Set directly across from the golf course, it offers an extraordinary connection to the Country Club and Arboretum. Inside, the home is filled w/warmth & character, from the inviting living room w/gas fireplace & sunny den w/built-in bookshelves to the family room, kitchen, dining room, which all overlook the backyard. A private garden retreat, framed by a canopy of mature trees & perennials. A newer deck connects two thoughtful additions, including the gracious & highly functional kitchen featuring SubZero & Wolf appliances, a generous island, and a light-filled breakfast room surrounded by windows & custom built-ins. Upstairs offers spacious bedrooms, 2 full baths, plus a walk-up attic for flexibility & accessible storage. Mudroom w/Dutch door, attached garage (fit 2 cars! ), & a brand new roof complete this timeless Nakoma residence. Welcome!

Welcome to this inviting 2-story townhouse in Madisonâs desirable west side! Offering 1,148 sq ft, this 2-bedroom, 1.5-bath home features a warm and comfortable layout with a spacious living room, wood-burning fireplace, large windows, and dining area with patio access. The kitchen offers warm wood cabinetry, subway tile backsplash, and ample storage. Upstairs, the primary bedroom includes a walk-in closet, while the second bedroom features unique wood paneling. Enjoy an attached underground 1-car garage, greenspace views, and several 2025 updates, including A/C, reverse osmosis filtration, water heater/filter, and a bedroom window. Located across from Elver Park and close to shopping, dining, and everyday conveniences

Step into a warm and welcoming great room, where an open floor plan and vaulted ceilings create an airy, inviting atmosphere around the cozy gas-burning fireplace. The kitchen is perfect for gatherings, featuring top-of-the-line Sub-Zero and Wolf appliances. Retreat to the spacious primary bedroom which includes a luxurious full bath and generous walk-in closet. Savor the sounds of nature from the newer back deck, or enjoy the privacy of the fenced-in backyard. Updates include the windows, appliances, deck, flooring and roof. The lower level offers a versatile rec room and two additional spaces ideal for an office, exercise room or hobbies

Welcome to Hawks Reserve, with a private elevator from your three car garage leading directly into this spacious condo. Exceptional views of Hawks Landing Golf Course from your two patios. Open floor plan provides plenty of room for entertaining with expansive kitchen with breakfast nook, opening up to the living room with fireplace, & formal dining. Primary suite is exceptionally laid out with an elegant bathroom with tiled walk-in shower, expansive closest, & fireplace. A private den is perfect for that extra space needed to unwind from a day on the course. Additional guest room with access to the patio makes everyone feel right at home. Located on Madison's west side with easy access to shopping, dining, & outdoor activities. Check out for more information

Great opportunity to own a well-maintained duplex in a desirable Madison west-side location! Whether you're looking to owner-occupy with rental income or just a solid investment property, 806-808 N Gammon Rd offers both options. Each side features 3 bedrooms, spacious living accommodations and an attractive layout. Both units include washer & dryer. 806 N Gammon has 2 ½ baths and an attached 2 car garage. 808 N Gammon has 3 ½ baths, a one car garage plus a finished lower level. The location is a major highlight. Situated on Madison's west side with easy access to restaurants, shopping, parks, schools, and other popular destinations, the property is also located on a bus line, making it convenient for a wide range of residents. Total sq ft per assessor; buyer to verify if material to transaction. This is an excellent opportunity for an owner occupant looking to offset their housing costs with rental income, or for an investor seeking a desirable duplex in a strong Madison location

Classic mid-century modern design and thoughtful updates come together in this distinctive Madison west side home. Designed by the original owner, an architect who lived here for 49 years, the home showcases custom details and timeless character, including a beautiful curved staircase to the lower level. Set on a large corner lot, the property offers a spacious backyard with room to enjoy the outdoors. Major updates include a partial roof replacement in 2021, furnace and water heater in 2019, A/C and owned water softener in 2017, and a radon mitigation system in 2025. Located in an established neighborhood near Parkcrest Pool and John Muir playground, with convenient access to UWâMadison, shopping, dining, parks, and everyday amenities

Move-in ready on a quiet cul-de-sac in Madison's Westhaven Trails! This updated 3-bedroom, 2-bath home features an open floor plan and cathedral ceilings. The spacious eat-in kitchen flows out to a deck overlooking the backyard, ideal for entertaining. The fully finished lower level includes a bedroom, family room, and a second full bath, perfect for a home office or guest space. Major systems updated for peace of mind: new roof, skylights, and washer/dryer (2020); new furnace (2022); and new water heater (2026). Attached 2-car garage. Close to Elver Park, shopping, and an easy commute to Fitchburg, Verona, and Madison's west side. UHP Warranty included for extra peace of mind. Schedule your showing today!

Fantastic location directly across from wooded green space and within walking distance of numerous parks. Welcome to this bright and inviting 3-bedroom, 1.5-bath home featuring an open floor plan, wood floors throughout the main level, and abundant natural light. Living room with expansive picture window and brick gas fireplace. Spacious kitchen offers plenty of room for cooking and gathering. Newly carpeted LL family room has egress window. Add one wall and you have a 4th BR! Fenced yard and oversized detached 2-car garage provide space, privacy, and convenience. Just 2 blocks from the Rapid bus stop at Whitney Way & Regent Street, with easy access to downtown and Madisonâs west side. Close to shopping, dining, and entertainment at Hilldale. A wonderful combination of comfort, space, and location!

Thoughtfully updated 2-bedroom, 1-bath home blends historic character with modern updates throughout. The main floor offers an open kitchen and dining area, a comfortable living room, and a full bath. Two bedrooms are located on the upper level. Central air, stone foundation, and an unfinished basement with excellent storage. Attached 1-stall garage and covered front porch. Walkable to Orton Park and the restaurants, cafes, and shops on Willy Street, with easy access to Lake Monona and bike paths. Adjacent 3,093 sq ft buildable lot at 1153 Jenifer is also available for buyers who want to acquire both parcels together. A rare opportunity to own a piece of Madison history in one of the city's most sought-after neighborhoods

Like new! Meticulously maintained 3-bed, 2-bath home on Madisonâs west side! The vaulted main level features an open floor plan with laminate flooring and a beautifully appointed natural ledgestone gas fireplace with raised stone hearth and wood mantel as the focal point. Kitchen offers white painted cabinetry, stainless steel appliances and island, open to the living room. Three bedrooms upstairs, including a spacious primary with 2 closets and walk-through bath featuring dual vanity. Walkout lower level is perfect for entertaining or watching the big game, with a second gas fireplace, rec room and full bath. Additional lower-level space provides excellent storage. Enjoy the nicely landscaped fenced yard, and storage beneath. Numerous updates include radon system, water softener (â21), fireplace, HVAC (â22), Humidifier ('23), roof/gutters, front steps, siding and garage lighting (â24), garage door/opener/springs, front railing and landscaping (â25), and whole-house dehumidifier ('26)

Move right into this beautiful 3 bedroom home conveniently located on Middleton's NE side. Home has had numerous updates over the last 7 years including furnace/AC, siding, windows, roof and remodeled kitchen. Spacious living room with gas fireplace conversion and LVP flooring. Enjoy the weather, but not the bugs in your screened-in porch. Fenced backyard includes a small brick patio area and a storage shed. Centrally located with easy access to East Madison, Waunakee, plenty of shopping and dining, Lake Mendota and Pheasant Branch Conservancy

Show 9/3. Tucked away on a private drive behind a gated entry, this beautifully maintained home offers an exceptional combination of space, privacy, and access to the water. Set on. 4 acres, the property includes waterfront access and a boat slip, making it easy to enjoy everything lake living has to offer. The main level features hardwood floors throughout, a spacious two-story living room, formal dining room, and a dedicated office. The kitchen offers Corian counters, stainless appliances, and a dining area. The main-level primary features a walk-in closet, dual vanity, jetted tub, and walk-in shower. A 3 season porch and maintenance-free deck extend the living space outdoors. Three additional bedrooms and a full bath are located upstairs, offering plenty of room for family or guests. The exposed lower level adds a bonus room, exercise room, ample storage and the finished bar and rec room is the cherry on top. There is also an insulated three-car garage attached

Exceptional multi-family investment opportunity on Madison's west side. Westward Manor features 32 units. 24 efficiencies and 8 one-bedroom layout options. Totaling 21,108 gross sq. Ft. Built in 1984, high occupancy (96.9%) and potential for rent improvement. Roof replacement in 2017. Each unit is equipped with individual PTAC Heating & Cooling units, dedicated basement storage and off-street surface parking. On-site coin-operated laundry facilities add convenience. Prime location near Research Park, Madison Area Technical College and local transit. A turnkey multi-family asset ready for your portfolio

Welcome home! This two-owner home features 4BR, 2.5 bath, and a 2-car garage in the highly desirable Middleton School District within walking distance of downtown Middleton. Located between Stricker and Tiedeman Ponds, offering easy access to walking trails and Woodside Heights Park. Relax on the spacious front porch overlooking the park and pond or entertain on the composite deck, brick patio with cozy fire pit. Upstairs, you'll find 4 BR with hard wood floors, updated full guest bathroom (2025) and a master bath. The main level offers office, formal living room and a family room featuring a charming brick fireplace for relaxing evenings at home. The kitchen boasts maple cabinetry, quartz countertops (2021), built-in banquette creating a functional and inviting space for everyday living and entertainment. Updates include new roof and decking, gutters and guards (2026), refrigerator (2025), water softener (2022), dishwasher (2020), furnace and air conditioning system (2018)

Affordable west-side homeownership without the maintenance of a larger property! This inviting first-floor studio condo offers a private entrance, efficient layout, and several desirable updates, including a newer dishwasher, countertops, microwave, and electric fireplace. In-unit washer and dryer add everyday convenience, while sliding glass doors provide access to the patio. Enjoy excellent community amenities including a clubhouse and fitness center, while the condo fee covers water/sewer, hot water, snow removal, and lawn care. Conveniently located near specialty shops, restaurants, movie theaters, and public transportation. A great opportunity to stop renting and start building equity in an affordable Madison home!