Highland Park, IL Homes for Sale under $2,000,000

This exceptional Highland Park residence offers nearly 5,300 square feet of impeccably designed living space, including a beautifully finished lower level, on an expansive lot just shy of an acre. Featuring 6 bedrooms and 4.5 baths across three finished levels, the home blends timeless elegance with modern sophistication. Sun-drenched interiors showcase wide-plank hardwood flooring, designer

Melissa Siegal @properties Christie's International Real Estate

Exceptional brick and stucco home perched on one of the prettiest streets in east Highland Park, situated on a gorgeous, nearly half-acre property with stunning fully-fenced and professionally landscaped backyard, now ready for new owners. Start your day with a morning stroll to That Little French Guy for coffee and a croissant, see what's new at the Highland Park Library, then enjoy your walk to

Cheryl Waldstein @properties Christie's International Real Estate

Exceptional location between Braeside and Ravinia! Don't be fooled from the outside-this meticulously maintained home offers nearly 4,500 square feet of beautifully designed living space filled with timeless character. A major 2001 renovation reconfigured the first floor while updating the electrical and plumbing, installing Marvin windows, attaching the 2-car garage, and adding a stunning

Ted Pickus @properties Christie's International Real Estate

Set on a beautifully landscaped property in sought-after East Highland Park, this luxurious home offers 5 bedrooms and 5.1 baths across thoughtfully designed living spaces. Blending classic architectural character with modern updates, the home is equally suited for everyday living and entertaining. The kitchen with a large center island has been recently enhanced with custom cabinetry, updated

Margie Brooks 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.

Spectacular Historic Queen Anne Revival on Nearly 3/4 Acre in East Highland Park. A rare opportunity to own a magnificent Queen Anne Revival residence, beautifully set on a private lot just under 3/4 of an acre in sought-after East Highland Park. This exceptional home offers the best of all worlds-historic beauty and grandeur paired seamlessly with modern additions and amenities designed for

Vince Dinh HomeSmart Connect LLC

A rare opportunity to own this beautifully Updated Contemporary Home with over 5000 sq feet of Living Space in one of East Highland Park's most sought-after neighborhoods. Featuring TWO LARGE PRIMARY BEDROOMS with EN-SUITE BATHROOMS, one on the MAIN LEVEL and one on the SECOND LEVEL. This exceptional 5-bedroom, 5 full bath, 2 half bath residence offers an Ideal Layout for today's lifestyle and is

Brooke Bakalar Sloane @properties Christie's International Real Estate

Rarely available 4,700 sqft ranch set on an expansive, meticulously landscaped property offering exceptional privacy and presence. This elegant 3 bedroom, 4.1-bath residence is thoughtfully designed and rich in architectural detail, unfolding in a refined yet understated and unexpected manner. The expansive foyer creates a gracious sense of arrival, immediately drawing the eye toward the stunning

Margie Brooks Baird & Warner

Rare opportunity to own a fully renovated 4-bedroom, 4.1 bathroom home set on a stunning East Highland Park ravine lot with nearly one acre of land at the end of a private cul-de-sac. Combining timeless elegance with extensive modern updates designed for today's lifestyle, this home features spacious living areas, hardwood floors throughout and magnificent views from every window. The beautifully

Margie Brooks Baird & Warner

Just steps from downtown Highland Park's shops, restaurants, library, train, and close to Lake Michigan, Thornycote is a home where location and history come together beautifully. Designed in 1901 by renowned architect Howard Van Doren Shaw, this English Arts and Crafts residence is a remarkable expression of craftsmanship, proportion, and grace. Set on more than an acre of lush, landscaped

Keith Goad Berkshire Hathaway HomeServices Chicago

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

Rita Masini Compass