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

An enchanting Craftsman cottage surrounded by mature landscaping and framed by a welcoming front porch, offering the perfect balance of character, comfort, and convenience. Inside, beautifully maintained hardwood floors and abundant natural light create warm, inviting living spaces designed for everyday living and entertaining. The open living and dining areas are accented by custom window

Alison Wertheimer @properties Christie's International Real Estate

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

Welcome to 1099 Princeton, a beautifully renovated 2 bedroom, 1 bathroom home in the highly sought after Sunset Park neighborhood of Highland Park. Perfectly situated in one of the area's most desirable locations, this move in ready home offers the ideal blend of charm, convenience, and modern updates. The home features an open concept floor plan designed for today's lifestyle. In 2021, the

Jacqueline Lotzof Compass

Turnkey is an understatement with this beautifully updated Highland Park condo. From the moment you walk in, you are welcomed by an inviting entryway that opens into the expansive living and dining room, complete with a gas fireplace. Around the corner, you will find the updated kitchen with a spacious eating area. Down the hallway is a generous laundry room, a well-sized second bedroom, and a

Michael Maggio @properties Christie's International Real Estate

Tucked away on a quiet Highland Park street, this updated ranch offers an affordable opportunity to get into one of the North Shore's most sought-after communities. Freshly painted and move-in ready, the home features 4 bedrooms, 2 updated bathrooms, and an open living space with newer flooring throughout. The refreshed kitchen includes 42" cabinets, stainless steel appliances, and plenty of

Julia Alexander Keller Williams North Shore West

Cute Three Bedroom Two bath corner ranch. Move in condition. Full finished basement. Two car garage. Great starter home for young family or perfect one level home for empty nester wanting to downsize. Walking distance to HP community pool. Close to downtown, Sunset Golf Course and interstate. Great quite area of Highland Park.

Peter Barber Berkshire Hathaway HomeServices Chicago

2 Flat. Each unit is 2 bedrooms, 1 bath. Long time tenants. Basement. Large parking lot. Near town, train, park, hospital and more. Sold "As Is".

Andrew Shevelev American Real Estate Services

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

Beautifully renovated, designer's own corner penthouse with balcony 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 3-bedroom unit, the current den

Deborah Fischer Berkshire Hathaway HomeServices Chicago

This lovely condo unit boasts a spacious interior with 2 bedrooms and 2 bathrooms with a total finished area of 1,410 sq.ft. The living spaces are filled with natural light, creating a bright and airy feel throughout. The kitchen is equipped with modern appliances and plenty of counter space, making it a perfect spot for preparing meals and gathering with loved ones. The bedrooms are comfortable

Jorge Romero Realty One Group Inc.

Sun-filled Corner East H.P. W/5 Bd Rms All On The 2nd Flr Hardwood Flrs. R Under Carpeting T/O Hm. Primary Bdrm W/Walk-In Closet, Fireplace, BTH Rm Walls Are Fully Tiled W/8'x5' Dry Sauna, Dual Vanities, Sep Shower & Soaking Tub Entryway Into Hm Via L-Shaped Combo Living/Family Rm. That An Wall Opening Can Be Done Into Dining Rm. Huge Open Kitchen W/Ajoining Dining Rm That Leads to 225 Sq Ft.

Don Yosef @properties Christie's International Real Estate

Rarely available three-bedroom, two-bath condominium offering an exceptional combination of space, natural light, and value. Enjoying a desirable southern exposure, this inviting residence features a thoughtfully designed split-bedroom floor plan, generous room sizes, and an oversized private balcony. A welcoming foyer leads to spacious living and dining areas, creating an ideal setting for

Noah Levy Compass

Rarely available and ideally situated overlooking the park, this lovingly maintained 3-bedroom, 2.5-bath townhome offers one of the best locations in Chantilly. Ready for your personal updates and design vision, this home features three spacious upstairs bedrooms, including a primary suite with private bath plus an additional full guest bath. The kitchen includes newer stainless steel appliances

Debbie B. Glickman @properties Christie's International Real Estate

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.

Opportunity knocks on coveted Castlewood Road! This 3-bedroom, 2-bathroom home sits on a generous 1/3-acre lot in one of Highland Park's most established neighborhoods - and it's ready for someone with the vision to bring it back to its full glory. Built in 1956 with the solid bones of mid-century construction, this 1,616 sq ft property offers the kind of square footage and lot size that buyers

Scott Rose Baird & Warner

True Indoor-Outdoor Living | First-Floor Condo with Extra-Large Patio Rarely available, sun-filled 2-bedroom, 2-bath residence featuring a desirable split floor plan and an oversized (1200 SF approx) west-facing veranda-ideal for relaxing and entertaining. Generous room sizes, separate living and dining areas, and a well-balanced layout. Recent improvements include newer windows, sliding glass

Jill Esko @properties Christie's International Real Estate