Highland Park, IL Homes for Sale under $500,000

Opportunity awaits at 1704 Park Avenue West! Situated on nearly 1/3 of an acre, this 3-bedroom, 1-bath ranch offers the perfect opportunity to renovate, expand, or build your dream home. Whether you're a homeowner looking to create your ideal space or a builder searching for an exceptional lot, this property is full of possibilities. The existing home features a functional floor plan with

Jacqueline Lotzof Compass

Charming townhome in the Ravina neighborhood Boasting FRESH PAINT THROUGHOUT close to parks, shopping, dining, Lake Michigan, and more! Beautifully maintained with a versatile layout, gorgeous natural light, and over 1,100 sq ft of above ground space. Whip up delicious meals in this stylish kitchen equipped with contemporary cabinetry, sleek appliances, and granite countertops. Options are nearly

Matthew Doughty Marketplace Homes

Absolutely stunning 2nd floor condo unit, completely renovated from top to bottom. Laundry Room located right across the hall from the unit! This immaculate residence features brand new hardwood flooring throughout, kitchen features abundant cabinets, elegant granite countertops, stainless steel appliances, and large island, perfect for entertaining. The unit offers two generously sized bedrooms

Tim Ratty Baird & Warner

Experience effortless living at 1250 Park Avenue West, a beautifully renovated corner-unit condominium in highly desirable Brooke Estates. Thoughtfully designed for both everyday living and entertaining, the open floor plan features rich wood engineered flooring and a beautifully updated kitchen with stainless steel appliances, granite countertops, a decorative tile backsplash, and an island for

Julie Mangione Coldwell Banker Realty

Welcome to this absolutely charming 2-bedroom, 2.1-bath townhome in a highly sought-after Highland Park location w/ beautiful pond views. The living room features a gas-log fireplace, overlooks the pond, and has direct access to a private patio, perfect for relaxing or enjoying your morning coffee. The kitchen offers ample cabinet space, a casual eating area, and a large window overlooking the

Stephanie Absler-Orsi RE/MAX Top Performers

Move right into this extremely well maintained Chantily home. Located in the center of the sought after Chantily complex. Large eat-in-kitchen flows right into family room. Large combo living room and dining room are perfect for entertaining. Primary suite includes tons of closet space including a cedar closet and new carpeting. Two additional generous size bedrooms and hall bath. Upstairs

Ted Pickus @properties Christie's International Real Estate

A truly exceptional offering in Highland Park, this completely reimagined condo is unlike anything else in the area. Renovated down to the studs in 2022 with uncompromising attention to detail, every inch has been thoughtfully designed to deliver a sophisticated, turnkey space with timeless style and exceptional quality. The spectacular chef's kitchen is the showpiece of the home and would easily

Stephanie Hofman @properties Christie's International Real Estate

More home than you think! This well-maintained split-level offers two spacious living areas-a living room on the main level and a bright lower-level family room with large windows that provide plenty of natural light. Unlike a ranch with a basement, both living spaces feel open, inviting, and are ideal for everyday living. This is an estate sale, and the home is being conveyed as-is. If you're

Jay Reid HomeSmart Connect LLC

Beautifully renovated, designer's own corner penthouse with balcony and southwest treetop views in a pet-friendly, boutique 12-unit elevator building, near vibrant downtown Highland Park and Sunset Valley Golf Club. Two bedrooms plus Den, 2 baths, 2 car heated garage parking. Bright & open concept condo is a rare find at over 1,900 sf, with a spacious covered balcony. Originally designed as a

Deborah Fischer Berkshire Hathaway HomeServices Chicago

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

Jorge Romero Realty One Group Inc.

Exceptional space and value in an in-town Highland Park location! This spacious three-bedroom, two-bath condominium offers generous room sizes, abundant natural light, southern exposure, and an oversized private balcony-an excellent opportunity to bring your own design ideas and create a home that reflects your style. A welcoming foyer leads to spacious living and dining areas, while the kitchen

Noah Levy Compass

Come see this bright and light 3 bdrm 2.5 bath end-unit home in Chantilly! This favorite and larger floor plan faces an interior courtyard (no road in front of your windows) with serene and lovely garden views.The entry leads to the living room, dining room and powder room. The spacious family room with wet bar, adjoins the living room, dining room and kitchen offering flexibilty and great flow.

Susan Zeller Jennings Realty,Inc.

Welcome home to this beautifully updated 2-bedroom condominium featuring one of the most desirable views in the building. Enjoy peaceful views overlooking the expansive rear grounds with mature trees and lush green space, all backing directly to a City of Highland Park public park, creating a serene and private setting.The spacious living room and dining room flow seamlessly together, offering an

Ted Pickus @properties Christie's International Real Estate

TWO PARKING SPACES! Beautifully updated 2-bedroom, 2-bathroom condo offering modern style, comfort, and convenience. The inviting living room features a gorgeous stone fireplace, creating a warm and welcoming space for relaxing or entertaining. The stylish kitchen boasts crisp white cabinetry, stainless steel appliances, stunning white quart countertops and a clean, contemporary design. Pella

Tami Leviton @properties Christie's International Real Estate

Enjoy PRIME PENTHOUSE LIVING with FABULOUS RESORT-LIKE POOL VIEWS from this nicely updated two-bedroom residence with TWO GARAGE SPACES (#13 and #14)!!! Ideally situated near expressways, shopping and restaurants, this sought-after residence is located in the prestigious Condos of Northbrook community where residents enjoy exceptional amenities, including a 24-hour gated entrance, on-site

Nancy Gibson @properties Christie's International Real Estate

Get ready for resort style living with this luxurious, updated, penthouse suite in highly sought-after Northbrook Country! This stunning, 2 bedroom, 2 full bath, top floor condo has SO many features and updates for the lucky buyer to enjoy. From gleaming hardwood flooring to updated kitchen/baths to newer HVAC, this condo has been carefully designed to be both beautiful and practical. As you

Leslie Silverman @properties Christie's International Real Estate