Highland Park

Highland Park has several attractions including a vibrant downtown shopping district and the Ravinia Festival. Ravinia Festival is an open-air pavilion seating 3,200, which hosts classical, pop and jazz concerts in the summer. It has been the summer home of the Chicago Symphony Orchestra since 1936. Concert-goers can purchase seats in the covered pavilion or tickets to sit on the lawn. Many visitors arrive early and picnic on the lawn before and during the concerts. The Ravinia Festival is located in the Ravinia District, originally an artists’ colony which still retains much of its early character and architecture.

Highland Park has several landmark structures listed in the National Register of Historic Places, notably the Willits House by Frank Lloyd Wright. In addition to several houses designed by Wright, the National Register lists homes designed by prominent architects including John S. Van Bergen, Howard Van Doren Shaw, Robert E. Seyfarth, and David Adler. Landscape architect Jens Jensen lived in Highland Park and designed a number of projects in the community that are listed on the register.

There are two public beaches in Highland Park, Rosewood Beach and Park Avenue Beach (which also has a boating facility). Highland Park is also home to the North Shore Yacht Club.

The main highway in Highland Park is US Rt 41, which connects Chicago to Milwaukee. There are four Metra stations within city borders (Braeside, Ravinia Park, Ravinia, and Highland Park), as well as two in nearby Highwood (Highwood and Fort Sheridan) on the Union Pacific/North Line, which begins in Chicago and terminates in Kenosha, Wisconsin. Pace also offers several bus routes. Boat launch facilities are available along Lake Michigan. O’Hare Airport is located approximately 20 miles southwest.

Schools

North Shore School District 112

Edgewood Middle School
Elm Place School
Northwood Junior High School

Township High School District 113

Highland Park High School

Demographics

As of the 2010 census, the population was 29,763. The median income for a household in the city was $100,967, and the median income for a family was $117,235. Males had a median income of $83,121 versus $41,175 for females. The per capita income for the city was $55,331.

Newest Highland Park Listings

620 Homewood Avenue Unit #407, Highland Park

$899,000

2 Beds ⋅ 3 Baths ⋅ 12791254 MLS ⋅ 2000 Green Bay Road Condos BLDG.

One of the Largest Units at 2000 Green Bay Road! Corner Unit Penthouse Loaded with Light, including Skylights. Original Floor plan had Three Bedrooms but this was Created as a Two Bedroom with a Huge Primary Suite with an Amazing Walk-In Closet and Bath. Hardwood Floors, Heated Floors in the Kitchen and Baths, Balcony with Tree Top Views. Two Garage Spaces, Additional Storage, New Roof on Building. An Absolute Beauty!

620 Homewood Avenue Unit #407, Highland Park

$4,700,000

5 Beds ⋅ 6 Baths ⋅ 12778380 MLS

A distinguished custom Grunsfeld estate, privately set on nearly 2 acres of exceptional tableland and ravine, offers a singular combination of architectural pedigree, uncompromising craftsmanship, and extraordinary privacy. This remarkable 5-bedroom, 5.1-bath residence showcases timeless design, an exceptional floor plan, and the highest quality finishes throughout. Soaring ceilings, dramatic floor-to-ceiling windows, wide-plank oak floors, English sycamore cabinetry, and a striking fossil stone fireplace create interiors of understated elegance and enduring sophistication. The first floor primary suite serves as a private retreat, featuring a walkout to the grounds, an expansive dressing and closet area, and a luxurious spa-inspired bath. Three additional bedrooms and two baths are located on the second floor. Outdoor living is equally impressive, with a swimming pool and expansive bluestone terrace overlooking the beautifully landscaped grounds. Additional amenities include a wine cellar, 6 car garage, 800-amp electrical service, whole-house generator, and fenced ravine. An increasingly rare offering for the discerning buyer seeking refined luxury.

811 Judson Avenue, Highland Park

$850,000

4 Beds ⋅ 3 Baths ⋅ 12789022 MLS

A striking mid-century modern home set on three-quarters of an acre of secluded, wooded grounds. Defined by dramatic vaulted and beamed ceilings, expansive floor-to-ceiling windows, and hardwood floors, the home offers a beautiful connection between its architectural design and natural surroundings. The main level features an inviting great room with a fireplace, a spacious dining room, and an updated kitchen with a generous center island, quartz counters, a Sub-Zero refrigerator, and BlueStar range. Upstairs, three bedrooms include a spacious primary suite with a spa-inspired bath, walk-in closet, and convenient second laundry area. The walkout lower level offers gorgeous slate flooring (2026), a family/recreation room, office or fourth bedroom, powder room, laundry, and utility/storage space. Outdoor living is equally appealing, with a screened-in porch overlooking the wooded yard and an adjoining deck that provides additional space for entertaining or simply taking in the peaceful setting. Notable improvements made by the current owner include updated landscaping and new trees (2026), exterior painting (2025), a new roof (2022), and a Sub-Zero refrigerator and BlueStar range (2022). Conveniently situated between Highland Park and Deerfield, with easy access to parks, shopping, dining, and the amenities of both communities. A rare combination of architectural character, privacy, and natural beauty.

1470 Ridge Road, Highland Park

$1,599,500

5 Beds ⋅ 8 Baths ⋅ 12793005 MLS

Surrounded by the peaceful, natural beauty of the Hybernia Preserve, this luxurious home offers water views and privacy seldom experienced. ***New Roof, Gutters, and Patio - 2020***New Exterior Paint - 2023***Kitchen Renovation - 2018***New Dishwasher - 2021***New Disposal - 2025***New Marble and Hardwood Flooring***Closets Professionally Organized - 2021***Whole House Generator - 2018***New Basement Egress Windows - 2023***A dramatic 2 story, marble floored foyer welcomes you and flows effortlessly to an open floor plan with a gorgeous volume ceiling great room with floor to ceiling windows that flood the residence with loads of natural light! Recently updated, this home offers 5+ Bedrooms (including a first floor primary suite AND a first floor guest suite that includes a dedicated guest bath) 6 full and 3 half baths, and a full basement which treats you to a spa room that rivals your most favored paid luxury spa experience. The attached garage offers parking for 3 cars (plus a lift to accommodate an additional 4th vehicle) and incredible additional storage. Additional updates include ***2018 whole house generator, ***new within 3 years HVAC, new water heaters, ***2018 flooring and new interior paint, 2021 professionally organized closets, 2018 incredible chef's kitchen with sub-zero fridge, wolf range, wine/bev cooler, and much more...while invaluable upgrades include wine cellar, theatre room, professional fitness room, 4 zone heating and cooling, security, irrigation, professional car lift in the garage...simply A+++. Step out to your gorgeous patio outdoor space which includes a gazebo complete with grilling station for your outdoor entertainment. You will feel like you are miles away from everything...and yet be only minutes away from everything that downtown Highland Park has to offer. Award winning schools and easy access to attractions like Lake Michigan beaches, Ravinia Park, Chicago Botanical Gardens, and so much more! This home is an absolute MUST SEE!

1745 Sundrop Circle, Highland Park

$1,795,000

6 Beds ⋅ 7 Baths ⋅ 12770627 MLS

Steeped in history and beautifully reimagined for modern living, this magnificent Captain's Mansion, dating to 1892, offers a rare opportunity to own a piece of Fort Sheridan's distinguished architectural heritage. Located just three homes from Lake Michigan within the National Historic Landmark District, this exceptional 7,654-square-foot residence seamlessly blends the grandeur and craftsmanship of the late 19th century with extensive contemporary renovations. Soaring ceilings, sun-filled interiors, hardwood floors, two staircases, multiple fireplaces, and seasonal lake views create an extraordinary setting for everyday living and entertaining. A gracious foyer introduces the home's impressive scale and timeless elegance, opening to a beautiful living room with fireplace and a formal dining room, both featuring stunning 11-foot ceilings. The newly redesigned gourmet kitchen combines style and functionality with updated cabinetry, quartz countertops, a generous center island, new stainless steel Wolf double ovens and cooktop, a new Sub Zero refrigerator, and a spacious pantry with a beverage bar and abundant storage. The expansive family room addition offers exceptional gathering space with direct access to a new Trex composite patio and fenced side yard. The second floor features three spacious ensuite bedrooms, including a luxurious primary suite with an oversized custom walk-in closet and a newly renovated spa-inspired bathroom featuring radiant heated floors, quartz countertops, a spacious shower, Jacuzzi tub, and heated towel rack. A comfortable loft and conveniently located laundry room complete this level. The versatile third floor offers a spacious second family room and two additional rooms ideal for bedrooms, home offices, or flexible living spaces. The finished lower level provides even more room to spread out, with a recreation room, additional bedroom, full bathroom, and second laundry room. Extensive recent improvements enhance the home's comfort and functionality, including three new HVAC and air conditioning systems (2025), electrical upgrades, new lower-level luxury vinyl flooring, screen doors, sprinkler system, custom mudroom closets, and window treatments. Freshly painted interiors and an attached three-car garage further complement this exceptional, move-in-ready residence. Originally part of the historic Fort Sheridan military installation, this remarkable home offers the rare opportunity to experience the architectural character and grandeur of a bygone era without sacrificing modern comforts. Surrounded by the natural beauty of Lake Michigan, scenic walking trails, and historic architecture, Fort Sheridan offers a distinctive lifestyle just minutes from the restaurants and shops of Highwood, Highland Park, and Lake Forest, with convenient access to Metra and downtown Chicago. An extraordinary combination of history, architectural beauty, generous living spaces, and modern luxury in one of the North Shore's most distinctive settings.

41 Scott Loop, Highland Park

$589,000

3 Beds ⋅ 2 Baths ⋅ 12792745 MLS

Ravinia! Completey updated & renovated in 2016! Features a bright and open floor plan! Beautiful New kitchen with great cabinet space, granite countertops, stainless appliances and center island with cool built-in fireplace! All New in 2016: New Kitchen, New Bathrooms, Windows, HVAC, Copper Water Piping, PVC plumbing, 200 Amp Electrical Panel, New Washer & Dryer, New Roof, and more. Solar panels also were installed in 2020 - fantastic with today's ever increasing utility bills. The main level features an open kitchen, dining, and family room space. Upstairs are 3 bedrooms and a full bathroom. The walk-out lower level features a spacious recreation room, full bathroom, laundry/Utility room and a crawl space with concrete floor. Beautifully & Professionally landscaped yard! Great walk to everywhere Ravinia location: Rosewood Beach, Farmer's Truck Wednesdays, Food Truck Thursdays, Green Bay Trail, Schools, Shops & Restaurants, Ravinia Festival, Chicago Botanic Garden and More! Just move right in and enjoy!!

475 Burton Avenue, Highland Park

$525,000

3 Beds ⋅ 3 Baths ⋅ 12790006 MLS

This home has all new up to date electrical wiring, a brand new bathroom, house covered with fresh paint, both inside and out. The lower level family room has plush new carpet.The location is close to schools, shopping, restaurants, Highway 41 and the 294 Toll Road. The sidewalks and the patio are new and freshly done. There is a brand new community center close by which offers numerous classes and activities. It is ready for new owners to enjoy!

1751 Clavey Road, Highland Park

240 Whistler Road Unit #1E, Highland Park

$2,100,000

5 Beds ⋅ 6 Baths ⋅ 12791592 MLS ⋅ Fort Sheridan BLDG.

Built in 1893 and designed by the celebrated Chicago firm Holabird & Roche, this landmark building in the heart of Fort Sheridan began its life as the Infantry Drill Hall and later served as the post gymnasium. Today it holds just 11 distinctive condominiums, and this end unit is one of its most special. With exposures to the east, north, and south, the home is filled with light throughout the day. The building's original wide, arched entrance on the east facade has been reimagined as a dramatic wall of windows, a striking reminder of the building's history. The kitchen pairs clean, contemporary design with serious function, including a Sub-Zero refrigerator and freezer, a Bosch dishwasher, and a six-burner FiveStar range with two ovens. A large marble island with a breakfast bar is the natural gathering spot, and the eating area beside it is surrounded by floor-to-ceiling windows. The kitchen opens to the family room, where 16-foot ceilings and walls of glass lead out to a 38-foot balcony overlooking the meadow and stream, a lovely place to start the morning or unwind at the end of the day. The primary suite has 13-foot ceilings, floor-to-ceiling windows, and its own balcony facing the historic water tower. The primary bath includes a walk-in shower, whirlpool tub, separate Toto toilet room, makeup vanity, and walk-in closet. One of many large closets, professionally built out, throughout the home. The lower level offers remarkable flexibility, with a family room lit by 25 feet of windows, two more bedrooms, two baths, an exercise area, a bonus room and workshop, ideal for guests, a home office, or extended family. Everyday living is easy here, with an elevator just outside the front door, all primary living spaces on the main level, and four assigned spaces in the attached heated garage. Step outside to gravel walking paths and head east for views of Lake Michigan, plus you're just a short walk from Highwood's restaurants, festivals, and food trucks in the park. A rare chance to own a piece of North Shore history, beautifully suited to how we live today.

240 Whistler Road Unit #1E, Highland Park

$2,250,000

4 Beds ⋅ 5 Baths ⋅ 12791828 MLS

RSTUDIO DESIGN GROUP ONCE AGAIN IS EXCITED TO PRESENT A STUNNINGLY TRANSFORMED ALL BRICK RANCH SET ON 1 ACRE LOT WITH A CIRCULAR DRIVEWAY LOCATED IN HIGHLY DESIRABLE HIGHLAND PARK COMMUNITY. HIGH CEILINGS. 4 BEDROOMS, 4.1 BEAUTIFULLY DESIGNED BATHROOMS. CUSTOM KITCHEN FEATURING TRENDY QUARTZITE COUNTERTOPS, UNIQUE CENTER ISLAND, PREMIUM CABINETRY AND HIGH-END APPLIANCES. THE FAMILY ROOM, COMPLETE WITH A FIREPLACE, OPENS TO A LARGE YARD WITH HUGE PATIO. HARDWOOD FLOORS THROUGHOUT. LUXURIOUS MASTER SUITE WITH A SPA-LIKE ENSUITE BATHROOM. SECOND BEDROOM SUITE. THIS HOME DELIVERS THE PERFECT BLEND OF ELEGANCE, STYLE AND FUNCTIONALITY. HUGE FINISHED BASEMENT. 3 CAR ATTACHED HEATED GARAGE, HOUSE GENERATOR, SPRINLER SYSTEM. ENJOY THE BEST OF SPACIOUS RANCH-STYLE LIVING ON AN EXTRAORDINARY LOT, ALL CONVENIENTLY LOCATED NEAR EXPRESSWAYS, SHOPPING, AND OTHER AMENITIES.

2035 Kipling Court, Highland Park

$1,650,000

5 Beds ⋅ 6 Baths ⋅ 12790920 MLS

A rare offering in one of Highland Park's most coveted locations - This stunning custom built all brick residence is beautifully positioned on a private tree filled lot and offers six bedrooms & 5.5 bathrooms. The gracious interior begins with an elegant foyer opening to a spectacular living room, where a striking stone fireplace and windows on two exposures fill the space with natural light. French doors transition seamlessly to the family room, complete with a second fireplace and an open connection to the chef's kitchen. Showcasing an oversized island with breakfast bar, granite countertops, premium stainless steel appliances, beverage refrigerator, breakfast area and generous walk-in pantry this is the perfect space for any home chef. A formal dining room with French doors is just off the kitchen along with a main floor bedroom with en suite, & a spacious mudroom with direct access to the attached three car garage. An elegant powder room completes the main level. Upstairs, the primary suite offers a tranquil private retreat with dual walk-in closets, and a luxurious en suite with separate vanities, soaking tub, oversized walk in shower and private water closet. Three additional bedrooms provide exceptional flexibility, including one with a private en suite bath and walk in closet, while two bedrooms share a beautifully designed Jack and Jill bath with dual vanity. The laundry room is just down the hall and features a utility sink and plenty of additional storage space. The finished basement extends the living space with an expansive recreation room with a bar, media room with screen, billiards room with pool table, sixth bedroom, full bath with walk-in shower and versatile bonus room currently used as a gym. Outside, a lush and beautifully backyard creates a private sanctuary, with mature trees, expansive lawn and a sophisticated paver patio ideal for al fresco dining and entertaining. Perfectly positioned just blocks from the Highland Park Metra, downtown shopping, acclaimed dining and farmers markets, with easy access to Lake Michigan, beaches, lakefront paths and Ravinia. Zoned to highly regarded District 112 schools and Highland Park High School. An exceptional opportunity in one of the most desirable locations on the North Shore.

1520 Oakwood Avenue, Highland Park

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Newest Highland Park Listings

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