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

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

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

Elegant French Provincial home set on a private street just moments from downtown Highland Park. Approximately 6,175 square feet, this Hamptons-style modern home includes 5 bedrooms and 4.1 baths and is nestled on over half an acre. Features include a gracious foyer, an oversized dining room with a wall of windows, a formal living room, and a study with a wet bar. The recently updated kitchen

Margie Brooks Baird & Warner

Welcome to The Ashbury This intimate collection of just 11 residences offers expansive 2,200-3,200 SQ FT layouts, including 3-bedroom homes, 3-bedroom + den options, and penthouses, priced from $1.65M to $2.8M-a rare blend of privacy, scale, and sophistication. Delivery Fall 2027

Jacqueline Lotzof Compass

Tucked away at the end of a private road and backing to a picturesque ravine, this exceptional estate offers a rare combination of ultimate privacy, natural beauty, and everyday convenience. Surrounded by mature trees and tranquil views, the home showcases timeless architecture, exceptional craftsmanship, and light-filled interiors designed for both grand entertaining and comfortable living. The

Lisa Rome Jameson Sotheby's International Realty

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

Just steps from downtown Highland Park's shops, restaurants, library, train, and close to the lake - this home has location at it's core. Thornycote a 1901 English Arts and Crafts design by Howard Van Doren Shaw, is a home where craftsmanship, harmony, and grace still define daily life. Set on over an acre of lush, landscaped land near Lake Michigan, this residence invites admiration and offers a

Keith Goad Berkshire Hathaway HomeServices Chicago

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.

This beautiful English Tudor-style house is situated in Highland Park, IL, an area renowned for its striking, intricate network of ravines, beaches, and bluffs. This is a rare opportunity to own a beautiful house in most desirable Eastern ravine part of Highland park Illinois. Not only it is just 10 minutes strolling to Rosewood beach of Michigan Lake and Ravinia Metra Station, also this house is

Jonathan Minerick Homecoin.com

A rare opportunity to own an architecturally significant Mid-Century Modern masterpiece by renowned architects Keck & Keck, nestled on an extraordinary 1.17-acre wooded site in one of East Highland Park's most coveted locations. Built in 1956 and thoughtfully rehabbed, this iconic ranch residence seamlessly blends timeless modernist design with contemporary comfort while embracing its

Tim Stassi Dwell One Realty

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

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

Experience unparalleled scale and sophistication in this one-of-a-kind Drill Hall residence within a boutique, luxury Fort Sheridan elevator building. Two units, offering an alternative to ranch inspired living, were expertly combined to create this 3 bedroom, 3.2 bath gallery style condominium with the added features of 3 spacious, private balconies overlooking the Meadow and the Pond, 2 loft

Judy Weiss @properties Christie's International Real Estate

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