Highland Park Real Estate

Welcome to Highland Park, a vibrant and inviting subdivision nestled in the heart of Madison, Wisconsin. Known for its picturesque landscapes and family-friendly atmosphere, Highland Park offers an exceptional blend of suburban tranquility and urban convenience.

As you explore this charming community, you'll find tree-lined streets, beautifully manicured lawns, and a diverse selection of homes that cater to various lifestyles. From modern single-family residences to cozy townhomes, Highland Park provides options for everyone, whether you're a first-time homebuyer, a growing family, or looking to downsize.

One of the standout features of Highland Park is its proximity to Madison's thriving cultural scene. Residents enjoy easy access to a plethora of parks, recreational facilities, and walking trails that encourage an active lifestyle. The nearby schools are highly regarded, making it an ideal place for families seeking quality education for their children.

Highland Park is also conveniently located near shopping centers, restaurants, and entertainment options, ensuring that everything you need is just a short drive away. The vibrant downtown Madison area, known for its festivals, farmer's markets, and eclectic dining options, is only a few minutes away, allowing residents to indulge in the best that the city has to offer.

In Highland Park, you’ll discover a close-knit community where neighbors become friends, and every day brings new opportunities for connection and enjoyment. Come and experience the charm of Highland Park—your dream home awaits in this delightful Madison enclave!

Newest Listings in Highland Park

$600,000

3 Beds ⋅ 2 Baths ⋅ 2028251 MLS ⋅ ACTIVE Status

Rich in character and thoughtfully updated, this storybook bungalow captures the warmth and charm of a bygone era. Bursting with curb appeal, this classic home showcases an inviting arched entry, gleaming hardwood floors, abundant natural light, and a cozy living room fireplace. The formal dining room with bay window flows seamlessly into the efficient kitchen, featuring quartz countertops and stainless steel appliances. Two bedrooms and a beautiful full bathroom complete the main level. The upper level offers a private primary with a convenient half bath. Outside you’ll find a patio surrounded by a lush yard, along with a one-car garage. Set on a picturesque tree-lined street, this home is just minutes from UW–Madison, Hilldale, parks, dining, shopping, and downtown Madison. Plus, easy access to scenic walking and biking paths. Don’t miss this rare opportunity own a beautifully maintained home with a British flair in one of Madison's most sought-after neighborhoods!

2618 Stevens St, Madison

$774,900

4 Beds ⋅ 3 Baths ⋅ 2027550 MLS ⋅ ACTIVE UNDER CONTRACT Status

Show 7/11. Beautifully maintained Highland Park home featuring a steel exterior, Lannon stone front entry, rare 2-car garage, and new roof in 2025. Character shines throughout with gleaming oak floors, original trim, faux fireplace, and built-in linen cabinetry. Updated kitchen with white cabinetry, stainless steel appliances, and breakfast bar open to the dining and living areas. Flexible layout with spacious bedrooms, upstairs office nook, walk-in closet, vaulted ceilings, and a soaking tub. Finished lower level offers a large rec room, remodeled bath, laundry, and storage. Fenced backyard with composite deck and mature shade tree, all on a charming tree-lined street close to UW, hospitals, restaurants, and the bike path!

2626 Chamberlain Ave, Madison

$839,900

3 Beds ⋅ 3 Baths ⋅ 2026491 MLS ⋅ ACTIVE Status

Showings begin 7/31. COMING SOON! Your Backyard Oasis Awaits. Discover the perfect blend of comfort, style, and thoughtful updates in this inviting 3-bedroom, 2.5-bath two-story home. From the new front door 2022 to the 2024 refrigerator and induction range, 2026 dishwasher, and 2023 water heater, every improvement reflects pride of ownership. Fresh interior paint, updated hardware, refinished bath woodwork, and numerous refreshes create a move-in ready feel, while the well-maintained furnace and A/C (2013) offer peace of mind. Ideally located near UW–Madison, UW Hospital, Hilldale Shopping Center, Hoyt Park, & downtown Madison. Two off-street parking spots! Relax in the beautifully landscaped backyard with a prairie garden, tranquil water features, and visiting songbirds and butterflies—your own private retreat. Pride of ownership shines throughout!

2638 Mason St, Madison

$479,900

3 Beds ⋅ 2 Baths ⋅ 2026526 MLS ⋅ ACTIVE UNDER CONTRACT Status

Welcome home to this solid ranch offering a spacious open-concept floor plan designed for comfortable everyday living & entertaining. Beautiful wood flooring flows throughout the main living areas, while large windows fill the home with natural light. The functional layout provides generous living spaces and a seamless flow between the kitchen, dining, and living areas. The expansive unfinished lower level is ready for your ideas, with egress windows already in place and a bathroom stubbed in, making it easy to add additional bedrooms, a family room, and another full bath to create the space you've always wanted. A 2-car garage provides ample room for vehicles, storage, and hobbies, with the added convenience of direct stair access to the basement. Step outside to enjoy the private backyard, perfect for relaxing, entertaining, or simply enjoying the peaceful setting. This well-built home offers exceptional potential & ready for its new owners!

809 Hanksfield Pl, Prairie Du Sac

$525,000

4 Beds ⋅ 3 Baths ⋅ 2025561 MLS ⋅ ACTIVE UNDER CONTRACT Status

Don't miss this charming 4 bedroom home located in a desirable neighborhood just a short walk from both the neighborhood park and Culver Park. Step inside to an inviting open-concept floor plan that offers a seamless flow between the living, dining, and kitchen areas—perfect for everyday living and entertaining. New carpet on the main level provides a fresh, updated feel throughout the home. Outside, enjoy a private backyard featuring a large deck that's perfect for entertaining family and friends, relaxing outdoors, or enjoying summer gatherings. Combining comfort, convenience, and a great location, this home is ready for you to move in and make it your own.

1019 21st St, Prairie Du Sac

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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.