Highland Park Homes for Sale

Highland Park Homes for Sale

Highland Park, located in Lake County, Illinois, is a vibrant city with a rich history and a strong sense of community. Nestled along the shores of Lake Michigan, this picturesque city offers a perfect blend of natural beauty and urban amenities.

One of the highlights of Highland Park is its diverse housing market, with a wide range of homes for sale to suit different lifestyles and budgets. Whether you're looking for a charming historic home, a modern condo, or a spacious family house, you'll find plenty of options in Highland Park.

The city boasts a variety of architectural styles, from classic Victorian and Tudor homes to sleek contemporary designs. Many properties in Highland Park feature beautiful landscaping, spacious yards, and scenic views of the lake or surrounding nature reserves.

Residents of Highland Park enjoy a high quality of life, with excellent schools, parks, and recreational facilities. The city is also known for its vibrant downtown area, which is home to an array of shops, restaurants, and cultural attractions.

If you're in the market for a new home in Highland Park, now is a great time to explore the available options. With the help of a knowledgeable real estate agent, you can find the perfect property that meets your needs and allows you to enjoy all that this wonderful city has to offer.

Newest Highland Park Homes for Sale

$2,500,000
5 Beds ⋅ 7 Baths ⋅ 12757737 MLS ⋅ NEW Status
No Showings until Saturday September 19th, 2026. RARE OPPORTUNITY ON COVETED WAVERLY ROAD IN EAST HIGHLAND PARK, DIRECTLY ACROSS FROM LAKE MICHIGAN. Set on approximately 1.3 acres, this stately 1933 brick and limestone estate combines an exceptional location, substantial existing residence and the flexibility to create something truly extraordinary. Offering approximately 5,510 square feet, the home is livable as it stands while presenting tremendous potential for renovation, restoration or a complete reimagining. Buyers seeking a classic Highland Park estate can preserve its architectural character while updating the home to their own style and standards. Those envisioning something entirely new may also explore the potential for new construction and a custom luxury residence on this estate-sized homesite. The existing residence showcases the craftsmanship and scale of its era with gracious room proportions, extensive millwork, crown moldings, paneled walls, built-ins, hardwood floors, expansive windows and five fireplaces. A sweeping staircase creates a memorable arrival, while formal living and dining rooms, a private paneled library, light-filled sunroom, custom kitchen, butler's pantry and multiple gathering spaces provide an exceptional foundation for personalization. The formal dining room is especially striking with paneled walls, a carved marble fireplace and statement chandelier, while the sunroom's floor-to-ceiling windows overlook the surrounding grounds and gardens. The private primary suite offers its own fireplace with original Delft tile surround, dressing room, bath and private balcony. Additional bedrooms, baths and recreation spaces provide flexibility for family, guests, home offices or additional living areas. The lower level extends the home's possibilities with a movie theater, fireplace, half bath and storage. Outside, approximately 1.3 acres provide a rare estate-like setting with mature trees, expansive lawn, established landscaping, perennial gardens, a fountain and two bluestone patios. The scale of the property offers room to create a remarkable private retreat and provides the kind of space increasingly difficult to find in this highly desirable area. THE LOCATION IS THE OPPORTUNITY. Positioned directly across the street from Lake Michigan on sought-after Waverly Road, this property places the lakefront lifestyle just outside your door. Enjoy convenient access to Lake Michigan, beaches and parks, Ravinia Festival, downtown Highland Park, shopping, dining, schools and Metra service to Chicago. Move in and update over time. Restore and renovate a classic 1933 brick and limestone estate. Reimagine the existing 5,510-square-foot residence around today's lifestyle. Or explore the possibilities of creating a new custom luxury home on an approximately 1.3-acre site in one of Highland Park's most desirable locations. For buyers searching for a large homesite, estate property, renovation opportunity or potential custom-build site in Highland Park, the combination of acreage, location and proximity to Lake Michigan makes 1418 Waverly Road an exceptionally compelling offering. The property is being offered AS-IS and priced with its current condition in mind, creating an opportunity for buyers, renovators, builders or those searching for an exceptional homesite near Lake Michigan. The address, acreage and setting are already here. The next chapter is yours to create.

1418 Waverly Road, Highland Park
$599,000
3 Beds ⋅ 2 Baths ⋅ 12757187 MLS ⋅ NEW Status
Ravinia! Completey updated & renovated in 2016! Features a bright and open floor plan! Beautiful New kitchen with great cabinet space, granite countertops, stainless appliances and center island with cool built-in fireplace! All New in 2016: New Kitchen, New Bathrooms, Windows, HVAC, Copper Water Piping, PVC plumbing, 200 Amp Electrical Panel, New Washer & Dryer, New Roof, and more. Solar panels also were installed in 2020 - fantastic with today's ever increasing utility bills. The main level features an open kitchen, dining, and family room space. Upstairs are 3 bedrooms and a full bathroom. The walk-out lower level features a spacious recreation room, full bathroom, laundry/Utility room and a crawl space with concrete floor. Beautifully & Professionally landscaped yard! Great walk to everywhere Ravinia location: Rosewood Beach, Farmer's Truck Wednesdays, Food Truck Thursdays, Green Bay Trail, Schools, Shops & Restaurants, Ravinia Festival, Chicago Botanic Garden and More! Just move right in and enjoy!!

475 Burton Avenue, Highland Park
$639,000
3 Beds ⋅ 2 Baths ⋅ 12756230 MLS ⋅ NEW Status
Built with enduring quality, this solid and brightly lit Highland Park home comes freshly painted and ready for immediate move-in. The main living areas feature stunning hardwood floors and a sunny living room that floods the space with natural light, while the lower-level family room offers a cozy retreat complete with built-in shelving and a beautifully tiled fireplace. Designed for function and entertaining, the spacious kitchen is packed with endless cabinet storage, an expansive breakfast bar, and sliding glass doors that open directly onto a deck overlooking a massive, fully fenced backyard with a dedicated dog run. Beyond the main yard, the side lot boasts your own private fruit orchard, complete with apple, cherry, and peach trees. Comfort extends throughout the home with spacious, high-storage bedrooms and updated bathrooms. On top of its timeless appeal, the property features major recent upgrades for total peace of mind, including a 2-year-old roof, a 2-year-old dishwasher, and a 4-year-old washer and dryer-making it the perfect setting to start building lasting family memories.

1320 Deerfield Place, Highland Park
$3,350,000
5 Beds ⋅ 7 Baths ⋅ 12756483 MLS ⋅ NEW Status
Situated on a prime half-acre lot in sought-after East Highland Park, this one-of-a-kind custom residence, completed in 2022, offers a rare combination of timeless architecture, warm contemporary design, and purposeful functionality, all executed with an uncompromising commitment to quality. While striking curb appeal sets the tone from the moment you arrive, the grand circular driveway, meticulously designed landscaping, dramatic full-view black aluminum and glass garage doors, and inviting front porch with a pergola and hanging swings establish the home's distinctive architectural character before you even step inside. The interiors prove to be every bit as impressive. Offering all the benefits of new construction without the time, uncertainty, and countless decisions of building from the ground up, every finish, fixture, and design decision was meticulously considered. Featuring six bedrooms, six full and one half bath, and an attached three-car garage, this exceptional residence reflects meticulous attention to detail throughout. Designed for both everyday living and unforgettable entertaining, the heart of the home is a chef's kitchen centered around a dramatic 12-foot waterfall island beneath a custom white oak ceiling detail. An oversized integrated stone sink with a matching apron front, full-height stone backsplash, and custom fluted hood create a striking focal point, while professional-grade Wolf and Sub-Zero appliances, dual dishwashers, a built-in plumbed Miele coffee system, and a walk-in pantry complete a kitchen designed without compromise. The adjoining breakfast area opens directly to the expansive brick paver patio, creating a seamless connection to the outdoor living spaces. Just beyond, the family room is flooded with natural light and offers beautiful views of the resort-style pool, spa, and professionally landscaped backyard. Anchored by a dramatic floor-to-ceiling black marble fireplace with a recessed television and immersive surround sound, the family room balances striking design with exceptional comfort. The main level also includes a versatile private office or guest suite with custom built-ins and sliding doors leading directly to the backyard. The second level features four spacious bedrooms, each with its own beautifully appointed en-suite bath. The luxurious primary suite combines warmth and sophistication with vaulted ceilings accented by white oak beams and shiplap, a linear fireplace, a private balcony overlooking the backyard oasis, two separate walk-in closets, and a spa-inspired bath featuring heated floors, custom white oak cabinetry, wall-mounted faucets, an oversized steam shower, and separate his-and-her water closets. A thoughtfully designed homework station and an expansive playroom/flex space with skylights further enhance the home's exceptional functionality. The fully finished lower level offers a spacious recreation room, wet bar, dedicated fitness studio, guest suite, and a professionally designed theater featuring stadium seating, a 120-inch projection screen, and immersive 7.1 surround sound. Outside, the backyard offers a true resort experience. Centered around a magnificent 44'22' pool and spa with expansive sun shelves and bubblers, the outdoor living spaces were designed for both intimate evenings and large-scale entertaining. A covered terrace with a television and ceiling speakers overlooks the beautifully landscaped grounds and expansive brick paver patio, creating an exceptional extension of the home's living space. A dedicated pool bath with direct access from the covered terrace allows guests to come in from the pool without walking through the home, while a nearby second washer and dryer for pool towels reflects the intentional planning found throughout. This custom residence reflects an uncompromising commitment to quality, timeless design, and everyday livability, a distinguished offering in one of East Highland Park's most sought-after neighborhoods.

1008 Bob O Link Road, Highland Park
$393,000
2 Beds ⋅ 1 Baths ⋅ 12756090 MLS ⋅ NEW Status
Alright, thrill-seekers and fearless renovators-here's a unique opportunity on prime Linden Avenue in East Highland Park. This charming 1920s two-bedroom, one-bath cottage has certainly been through its share of challenges. After years of difficult tenants and other issues, the property was cleared out and underwent a rehabilitation in 2024. While some improvements have been completed, the home still has some renovation wishlist, including a new roof, kitchen and bath glow-up, flooring repairs, paint throughout, new decks front and back, French drains, plus full attic and roofing restoration. Priced to reflect the truth, sold strictly as-is. Perfect for the FHA Limited 203(k) program - roll up to $75,000 of those fixes right into your mortgage. Ten-minute walk to town, fifteen to the lake, great schools, quarter-acre lot. Highland Park living, just with... character. Showings by appointment only. All showings require buyer verification and prequalification before access is granted. Door code provided only to verified, serious buyers only.

1458 Linden Avenue, Highland Park
$2,799,000
6 Beds ⋅ 9 Baths ⋅ 12754915 MLS ⋅ NEW Status
Privately set behind a gated entrance on over 1.3 professionally landscaped acres, this exceptional Highland Park stone and brick estate offers approximately 9,600 square feet of beautifully appointed living space, an attached four-car heated garage, and a rare sense of privacy surrounded by the natural beauty of Chicago's North Shore. Thoughtfully designed to live like a ranch with a luxurious first-floor primary suite, the home offers ultimate flexibility for a variety of lifestyles while still providing exceptional space for family and guests. Designed for both elevated entertaining and effortless everyday living, the home features a spectacular chef's kitchen completely reimagined in 2023 with custom black cabinetry, marble countertops, a dedicated coffee center, two dishwashers, and a striking glass-enclosed, temperature-controlled wine cellar display that creates a dramatic architectural focal point. An expansive accordion door system opens seamlessly to the full-length paved terrace and grounds beyond, creating an exceptional indoor-outdoor connection. The dramatic great room is defined by soaring ceilings, walls of windows, and an impressive double-sided fireplace, while the adjacent family room provides an inviting setting for more relaxed living. The main-level primary suite is a true private retreat, complete with a sitting room, fireplace, wet bar, and serene views of the property. Upstairs, five additional en-suite bedrooms provide exceptional accommodations for family and guests, complemented by an extraordinary 52-by-22-foot bonus room offering endless possibilities. The expansive lower level is designed for recreation and wellness with a private home theater, fully equipped gym, sauna, wet bar with kegerator, and full bath. Recent improvements include a new roof, gutters, and downspouts in 2024, newer HVAC systems, a rebuilt staircase, and a remodeled mudroom with heated floors. Directly behind the property, the forest preserve provides a breathtaking natural backdrop with direct access to a walking path, while dramatic western exposures capture spectacular sunsets across the grounds. Ideally positioned between downtown Highland Park and Deerfield with convenient highway access, owners of this exceptional estate have the unique option to attend either award-winning Highland Park High School or Deerfield High School-an extraordinary advantage within this coveted North Shore setting.

1630 Ridge Road, Highland Park
$899,000
5 Beds ⋅ 3 Baths ⋅ 12748876 MLS ⋅ NEW Status
Welcome to this beautifully updated and spacious 5 bedroom home in coveted Braeside. Move in ready this home features a 2 story foyer which opens to a bright interior filled with natural light. Open floor plan and hardwood floors. The main floor offers a separate dining room perfect for entertaining or everyday dining and a large living room with a picture window. The kitchen with granite, stainless appliances,and eat-in area opens to the family room featuring a fire place.The Primary suite features a large walk-in closet, an en-suite bath with a separate shower.. There are 3 additional upstairs bedrooms with large closets. Hall bath has double sinks. 5th bedroom off the family room is perfect for home office or studio.Laundry room is right off the kitchen. Large unfinished dry basement offers additional storage.2 car attached garage. The beautifully landscaped resort like backyard with a large deck is spectacular and perfecter entertaining. Location! Location! Close to Ravinia Festival and Botanic Gardens. Easy access to the Edens, Sheridan Road and 94.Close to metro train.

358 Hastings Avenue, Highland Park
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 12751434 MLS ⋅ ACTIVE Status
Welcome to 723 De Tamble Avenue, a classic all-brick Colonial set on an expansive, professionally landscaped lot in desirable East Highland Park. Entirely renovated in the last two years, this sun-filled home seamlessly blends timeless character with modern updates and an open, inviting floor plan. The foyer welcomes you into a spacious living room with a gas fireplace, while the open-concept kitchen and family room serve as the heart of the home. A wall of windows fills the space with natural light, and a second gas fireplace creates a warm and comfortable gathering area. The beautifully renovated kitchen features rich blue cabinetry, quartz countertops, all-new appliances and a generous eat-in area with built in seating nook. A large formal dining room provides the perfect setting for entertaining. Upstairs, discover three generously sized bedrooms, including a serene primary suite with a separate dressing area and a completely renovated private bath featuring a luxurious steam shower. Newly added hardwood flooring and abundant closet space complete the upper level. All remodeled baths and the powder room was moved to allow the Kitchen to open to the Family Rm. The main level is all newly refinished hardwood. Additional highlights include a convenient customized first-floor laundry room and a partially finished lower level with a versatile bonus room. Outside, enjoy a private, fully fenced yard surrounded by mature landscaping. Major improvements include a new roof, many newer mechanicals and a lawn sprinkler system. Feels like new! Ideally located just minutes from downtown Highland Park, and all that it has to offer, this beautifully updated home is ready to enjoy. Welcome home!

723 Detamble Avenue, Highland Park
$3,900,000
4 Beds ⋅ 6 Baths ⋅ 12750752 MLS ⋅ ACTIVE Status
Amazing lakefront property on end Cul De Sac street!!! This home has been totally REMODELED and meticulously curated for modern living with impeccable design. The expansive floor plan features four generous bedrooms, each with its own en-suite bathroom, including a refined primary retreat complete with 12 foot ceiling, a private balcony overlooking iconic Lake Michigan and 2 lavish walk-in closets. Culinary artistry is redefined in the exceptional chef's kitchen, outfitted with professional-grade appliances and a discreet scullery-perfect for both upscale entertaining and daily life. Exceptional amenities include a finished basement with a full bath, second-floor laundry , a first-floor office, a powder room, and expansive living spaces that are bathed in natural light. Perfect indoor-outdoor harmony is achieved through a serene three-season room, and a stone terrace, all providing ideal vantage points to enjoy the tranquil lakefront setting. Enjoy an unbeatable Highland Park location on a commanding .63-acre lot with panoramic Lake Michigan views. Stairs down to the beach are adjacent to back yard, shared with residence on the street.

22 Lakeview Terrace, Highland Park
$1,675,000
5 Beds ⋅ 9 Baths ⋅ 12746465 MLS ⋅ ACTIVE Status
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 Basement Egress Windows - 2023***A dramatic 2 story, marble floored foyer welcomes you and flows effortlessly to an open floor plan with a gorgeous volume ceiling great room with floor to ceiling windows that flood the residence with loads of natural light! Recently updated, this home offers 6 Bedrooms (including a first floor primary suite AND a first floor guest suite that includes a dedicated guest bath) 6 full and 3 half baths, and a full basement which treats you to a spa room that rivals your most favored paid luxury spa experience. The attached garage offers parking for 3 cars (plus a lift to accommodate an additional 4th vehicle) and incredible additional storage. Additional updates include ***2018 whole house generator, ***new within 3 years HVAC, new water heaters, ***2018 flooring and new interior paint, 2021 professionally organized closets, 2018 incredible chef's kitchen with sub-zero fridge, wolf range, wine/bev cooler, and much more...while invaluable upgrades include wine cellar, theatre room, professional fitness room, 4 zone heating and cooling, security, irrigation, professional car lift in the garage...simply A+++. Step out to your gorgeous patio outdoor space which includes a gazebo complete with grilling station for your outdoor entertainment. You will feel like you are miles away from everything...and yet be only minutes away from everything that downtown Highland Park has to offer. Award winning schools and easy access to attractions like Lake Michigan beaches, Ravinia Park, Chicago Botanical Gardens, and so much more! This home is an absolute MUST SEE!

1745 Sundrop Circle, Highland Park
$2,500,000
5 Beds ⋅ 4 Baths ⋅ 12737545 MLS ⋅ ACTIVE Status
Completely rebuilt and reimagined in 2021, this stunning 5-bedroom, 4-bath home offers an exceptional open-concept floor plan with high-end finishes throughout. Every major component including the roof, windows, plumbing, mechanicals, flooring, cabinetry, millwork, and appliances is just five years old, providing the feel of new construction. Designed for easy living, the home lives like a ranch with the exception of the family room, recreation room, and garage are located on the lower level. Dual mudrooms and laundry areas on both levels add everyday convenience. Set on a picturesque ravine across from Rosewood Beach on a quiet dead-end street, this exceptional home is ideally located in Highland Park's highly sought-after Ravinia neighborhood.

89 Cary Avenue, Highland Park
$740,000
3 Beds ⋅ 2 Baths ⋅ 12743730 MLS ⋅ ACTIVE Status
Enjoy the comfort and style of this beautifully renovated 4-bedroom, 2-bath home, ideally situated on a quiet, dead-end street lined with mature trees and just two blocks from Woodridge Park. Thoughtfully redesigned with an open-concept floor plan, the home combines modern finishes with inviting living spaces designed for both everyday living and entertaining. The bright and spacious first floor features new wide-plank white oak flooring, new windows and doors, and designer finishes throughout. The beautifully designed kitchen showcases custom European-style cabinetry, Lumataj quartz countertops, a generous center island, and new refrigerator/freezer, oven, range, and dishwasher. Beautifully designed bathrooms and custom closets add to the home's sophisticated, move-in-ready appeal. The expansive finished lower level provides exceptional additional living space, with a large recreation and entertaining area featuring a bar, a separate play area, an additional bedroom, a full bath, and laundry facilities. Outside, enjoy the large, wooded backyard and brand-new patio-an ideal setting for outdoor dining, entertaining, or simply relaxing. Additional improvements include a new high-efficiency furnace, central air-conditioning, washer, dryer, and French drains. The location is equally impressive. Woodridge Park is just a two-minute walk away, offering basketball and tennis courts, a playground, and an open play field. Red Oak Elementary School and the newly constructed West Ridge Community Center are also within walking distance. Convenient access to Route 41 and the Edens Expressway makes commuting easy, while nearby shopping and services along the Skokie Road corridor are just minutes away. Enjoy everything Highland Park has to offer, including the Ravinia Festival, Rosewood Beach, Hidden Creek AquaPark, local golf courses, parks, restaurants, shopping, and vibrant downtown Highland Park - all just minutes from home.

263 Barberry Road, Highland Park
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