East Highland Park Houses for Sale

This well-designed 5,500 sq. ft. Craftsman built, vintage home, designed by renowned architect Pingeree in 1915, offers an unparalleled blend of historic charm and modern convenience. Originally built as a summer retreat for the Witherspoon family, it sits on a generous 29,000 sq. ft. lot in in one of East Highland Park's prestigious historic districts, just a short stroll from Morraine Beach and

Linda Levin Jameson Sotheby's Intl Realty

A Nagle Hartray-designed architectural showstopper, this unique and meticulously upgraded residence sits on a lushly landscaped acre near Rosewood Beach and Ravinia. Newly enhanced with bespoke updates that blend timeless design with modern refinement, this home is a study in elegance, comfort, and effortless luxury. At its heart, the soaring two-story living room, crowned by a barrel ceiling and

Janice Corley RE/MAX Premier

Tucked away in one of Highland Park's most coveted east-of-Sheridan enclaves, just moments from the lakefront and jaw-dropping Rosewood Beach, this sprawling residence blends timeless architecture with refined amenities and over 10,000 square feet, offering a rare lifestyle of elegance, privacy, and ease. Situated on a lush, tree-canopied setting at nearly 3/4 of an acre, with manicured gardens,

Karen Biazar North Clybourn Group, Inc.

Move right in and expand your wings in this almost 5,000 square foot home plus over 2,000 additional square feet in the basement. Most of this home has been tastefully updated, including, kitchen and baths. Lots of fabulous architectural detail in this home: barrel ceilings, built-ins, stoned wall, lots of windows and 10 foot ceilings on the 1st floor. Magnificent kitchen with island,

Ted Pickus @properties Christie's International Real Estate

Stunning Custom Contemporary on Coveted Double Lot in Highland Park designed, built and meticulously maintained by the current owners. This one-of-a-kind home sits on over an acre on a beautiful ravine on one of Highland Park's most sought after streets - just steps from town, top-rated schools, the Lake, parks, and more. With soaring ceilings and expansive open living spaces, the home offers an

Linda Levin Jameson Sotheby's Intl Realty

Stunning Howard Van Doren Shaw English Arts and Crafts home on over an acre of magnificently landscaped property, one and a half blocks from Lake Michigan. Fine architectural detailing throughout, including the 2017 renovated kitchen completed with a butler's pantry and a coffee bar. Wonderful coach house with 4 garage bays, a full 2-bedroom in-law suite, or a fully functioning office,

Maxine Goldberg Engel & Voelkers Chicago North Shore

List price is lower than the assessed value so the taxes should go down for the new owner. Why Would You Want Ordinary When You Can Have Extraordinary! This Stunning and Majestic Brick Home Sits on Over an Acre in the Heart of Highland Park and Features a 40' Indoor Pool with a Wall of Glass that Opens to the Outdoors! Over 7600 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement, It Boasts

Janet Borden Compass

Welcome to 55 Prospect Avenue-where every day feels like a seaside escape. Perfectly sited on 1.5 acres with an extraordinary 175 feet of private Lake Michigan beachfront, this coastal-inspired estate offers a rare blend of architectural elegance, resort-style living, and timeless design. Evoking the relaxed sophistication of the Hamptons, this is Highland Park's crown jewel. Designed and built

Carrie McCormick @properties Christie's International Real Estate

Ravinia! Charming 3 bedroom brick bungalow! Freshly painted interior & refinished hardwood floors. Features include: 3 bedrooms on the main floor with a full bathroom, inviting living room with wood burning fireplace, sunroom, kitchen with walk in pantry, detached 2 car garage, full finished basement with additional full bathroom. There is a pull down stairs to a large attic space for extra

Cory Albiani @properties Christie's International Real Estate

DON'T MISS OUT ON THIS EAST HIGHLAND PARK GEM! Charming classic ranch is ready to move in, offering newer windows, spacious closets, built-in cabinets and shelving, new smoke/carbon detectors. Filled with plenty of natural light, crown moldings, hardwood floors, French Doors leading to the Cedar Deck in the back yard, wood burning fire place, kitchen with granite countertops and slate flooring.

Izabela Dianovsky Jameson Sotheby's International Realty

Just an adorable bungalow style home from the late 1930s, loaded with charming details in a great location close to Ravinia and downtown Highland Park. Enter to foyer area with convenient coat closet and arched entry to spacious living room. Wood burning fireplace here and aesthetic front picture window. Living room leads to a formal dining area with built-in hutches/bookcases. The dining room

Kris Seegren RE/MAX Plaza

This extraordinary lakefront residence is the ultimate blend of luxury, comfort, breathtaking views and private beach. This sophisticated contemporary home boasts 9,749 square feet above-grade and an additional 4,434 square feet of finished lower-level space, all of which has been thoughtfully redesigned during a comprehensive renovation from 2006 to 2008. Every aspect of this dream property was

Erin Smith @properties Christie's International Real Estate

Introducing an exceptional lakefront residence on one of Highland Park's most coveted private lanes. Set on a masterfully landscaped 1.85-acre parcel, 2441 Woodbridge Lane offers a rare combination of privacy, scale, and sophistication-backed by unobstructed, panoramic views of Lake Michigan. This architecturally striking, contemporary home spans approximately 10,000 square feet and has been

Patrick Milhaupt Jameson Sotheby's International Realty

Unique one of a kind Log Cabin home on .63 of wooded acre with ravine. 5 bedrooms, 3 full baths, basement and 3 car heated garage. Beamed vaulted ceiling family room with fireplace, fireplace in primary suite as well. 2 bedrooms have separate wing with Jack and Jill bath. Property hosts potting shed, tree house, screened in music room to listen to Ravinia Festival and dog run. Located 1 Block

Ted Pickus @properties Christie's International Real Estate

Incredible Highland Park Location With Double-Lot & Coach-House Near Metra-Rail & Downtown Retail With Convenience To 41/94 Highways & Always Immaculate With Additional 5-Car Parking For Possible Tenants Above Garage Is 1-Bedroom & Coach-House Will Convert To 2+Bedroom (Note: Main House Has Darling 4-bedrooms & Full-Bath Without Master)

Sheryl Fisher Coldwell Banker Realty

THIS BEAUTIFUL HOME IS JUST STEPS AWAY FROM A TRANQUIL OASIS W/ NATURE AND WALKING PATHS FOR MILES. THIS 1ST FLOOR MASTER, ASTORIA, FEATURES LUXURY FINISHES THROUGHOUT THE HOME! DESIGNED WITH CUSTOM CABINETRY, QUARTZ COUNTER TOPS THROUGHOUT, FIREPLACE, SOLID CORE 8' DOORS, DESIGNER LIGHT FIXTURES, TRAY & CATHEDRAL CEILINGS, AND UPGRADED TRIM PACKAGE W/ EXTENSIVE CROWN & WAINSCOT ALL INCLUDED IN

John Barry Mc Naughton Realty Group