5-Bedroom Homes for Sale in Highland Park, IL

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

1144 Green Bay Road is a unique and unparalleled French Country estate originally built in 1937 by prominent architect, William Mann and meticulously restored in 1996 to resemble a French chateau. The exterior of the home was built with limestone and concrete base, and the interior was designed with steel supports and steel girder throughout, with most interior walls of plaster. Situated on 1.37

Melissa Lipschultz Baird & Warner

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.

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

The assessed value is $3,627,762. and that is what the tax bill is based on. The taxes have been appealed and should go down substantially 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

Janet Borden Compass

First time on the market with only one owner having lived here, you'll find a magnificent stone and brick masterpiece that rests on just under a spectacularly landscaped 1.5 acres. This elegant home lives like a ranch and was designed for entertaining from the inside out. First floor Master suite complete with sitting room, fireplace, wet bar, large WIC, spacious bath with double sinks, steam

Kim Kelley Baird & Warner

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

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

Attention Investors or End Users! Discover this fantastic turnkey 2-family Townhome. Ideal for living in one unit while renting out the other, this beautifully updated duplex offers a perfect blend of comfort and functionality. Each unit features a kitchen with lovely white cabinetry and granite countertops, complemented by an adjacent dining area. Enjoy the cozy ambiance of the living room's

Ellen Chukerman Compass

Welcome to 2005 Keats Lane! Tucked away on a serene, quiet lane lined with towering trees and dappled sunlight, this expansive home sits on nearly a full acre of land. Located in sought-after Highland Park, within the award winning Wayne Thomas and Deerfield school districts, this home offers the perfect balance of original and new. Lovingly maintained and impeccably remodeled from top to bottom,

Daniel Cartalucca Coldwell Banker Realty

Luxurious Contemporary Home Nestled on Nearly An Acre in the Sought-after High Ridge Neighborhood, this Exceptional Brick Home Offers a Blend of Elegance, Comfort, and Convenience, with your Choice of Highland Park or Deerfield High Schools. This Rare Gem Boasts Two Primary Suites for Added Luxury- One Conveniently Located on the Main Level, Complete with His-and-Her Bathrooms, Walk-in Closets,

Janet Borden Compass

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

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

Fall in love with this exceptional brick home that offers comfort, elegance and versatility. Nestled on a peaceful dead-end street, this move-in ready residence boasts an expansive and thoughtful layout with 5 full bathrooms and 3 master suites. The third floor master suite is a standout space ideal as a home office, gym or private retreat. The heart of the home features a stunning custom kitchen

Lora Zlotnik American Real Estate Services

WELCOME TO 3464 OLD MILL ROAD - A MASTERFULLY CRAFTED PRAIRIE-STYLE ESTATE INSPIRED BY FRANK LLOYD WRIGHT, NESTLED ON OVER AN ACRE OF A SERENE, PRIVATE, TREE-FILLED LANDSCAPE IN COVETED HIGHLAND PARK. WITH OVER 9,000 SQUARE FEET OF LIVABLE SPACE, THIS RESIDENCE OFFERS A ONE-OF-A-KIND LIVING EXPERIENCE WHERE MODERN FUNCTIONALITY MEETS TIMELESS ARCHITECTURAL BEAUTY. FROM THE MOMENT YOU ENTER,

Kelly Ipjian Exit Strategy Realty

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

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

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

Set on a pristine 3 acre parcel in the prestigious enclave of Lake Forest, this magnificent 10,300 square foot estate epitomizes luxury living at its finest. This home has been designed with timeless elegance and modern sophistication, this architectural masterpiece offers unparalleled craftsmanship. Step though the double doors into the breathtaking two-story foyer that sets the tone for this

Joe Biewer Baird & Warner