Highland Park, IL Homes for Sale with Acreage

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

Expanded and renovated in 2008, this two-story prairie-style executive home offers over 9,000 square feet of finished living area across three levels, all easily accessible by a centrally located elevator or stairs, and is situated on over an acre of wooded property along a quiet, private road in Highland Park. The home offers exceptional flexibility with spaces ideal for a variety of lifestyles,

Kelly Ipjian Exit Strategy Realty

Some estates are built to impress. This one was built to live in, beautifully, privately, and without compromise. Set behind a gated entry on 1.34 professionally landscaped acres, this stone and brick manor offers something increasingly rare on Chicago's North Shore: true privacy, generous space, and a connection to nature that cannot be manufactured. A serene prairie stretches beyond the

Dina Lissner Nanberg Baird & Warner

Peace, privacy, perfection! This beautiful home on over an acre with a main floor primary suite features incredible views of the magnificent property! Gutted to the studs in 2016, a 2nd floor with 2 huge bedrooms and a shared bath was added! Light filled space along with a wonderful screened porch and an outdoor deck truly maximizes the serene setting. The kitchen opens to the family room and

Janet Borden Compass

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 8000 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement, It Boasts Barrel Ceilings over 20' High and 5 Fireplaces. The Double Island Chefs Kitchen has a

Janet Borden Compass

The epitome of luxurious one-level living. Set on a magnificent 3+ acre parcel in an exclusive private enclave, this extraordinary property is surrounded on three sides by the Heller Nature Preserve, offering 97 acres of protected land, serene privacy, and breathtaking natural beauty. Enjoy miles of scenic trails ideal for hiking, cross-country skiing, and horseback riding-an unmatched setting

Honore Frumentino @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

INTERIOR OF HOME CAN BE SHOWN STARTING 3/3. APPOINTMENT MUST BE CONFIRMED. PLEASE DO NOT COMMENT ABOUT PROPERTY IN THE HOME WHERE ELDERLY OCCUPANTS ARE PRESENT. NO SIGN ON PROPERTY. Prime Highland Park property being marketed as complete gut rehab or tear down on private cul de sac with higher priced homes. Option is yours to remodel or tear down and build. Home and property are being sold in as

Alice Scifo RE/MAX Advisors

MULTIPLE OFFERS RECEIVED - H/B due by 5/9/26. Set at the end of a private, cul-de-sac just off Sheridan Road in sought-after East Highland Park, this award-winning mid-century modern ranch offers a rare opportunity to own a true piece of North Shore architectural history. Designed in 1959 by renowned architect Henry L. Newhouse II, the home sits on just over an acre overlooking a tranquil,

Kelly Dunn Rynes Berkshire Hathaway HomeServices Chicago

Located in the coveted Belle Avenue Historic District, this extraordinary estate sits on 2.3 acres of manicured grounds with sweeping lake views. Fully renovated and expanded, the residence blends timeless elegance with modern luxury for a truly one-of-a-kind offering. This five-bedroom, eight full and one half bath home showcases craftsmanship of the highest caliber, including a brick exterior,

Beth Wexler @properties Christie's International Real Estate

Sophisticated new custom built 5 bedroom, 6 full bath & 2 half bath home with guest house, patio, pool & spa located on over 3 acres. This limestone & stucco clad home w/composite terra cotta Spanish roof tiles boasts unsurpassed quality construction by Red Rock Homes & is accompanied w/high-end interior designer finishes by Ilene Chase. Some of the home's highlights include: soaring ceilings,

Beth Wexler @properties Christie's International Real Estate