Newest Homes for Sale in Highwood, IL

Custom Remodeled 5-Bedroom, 3-Bath Home - Fully Permitted Renovation! Beautifully renovated from top to bottom, this exceptional home seamlessly blends elevated finishes, thoughtful design, and functional living space. Major improvements include a new architectural shingle roof, premium LP SmartSide siding, new windows, gutters and downspouts, furnace, central A/C, water heater, updated plumbing

Dmitry Livshis Liv Realty Inc

1st time on the market in nearly 100 years! Classic stucco duplex, centrally located in bustling Highwood! Each 3 bedroom two story unit offers 3 bedroom & 1.5 bathrooms with an additional 1/2 bath in each basement, along with laundry rooms and storage rooms. Beautiful hardwood floors throughout each unit (units 240 & 242). Classic 20's architecture with arches and textured plaster. Each unit has

Cory Albiani @properties Christie's International Real Estate

Charming, Updated Home in the Heart of Highland Park Welcome to this beautifully updated 4-bedroom, 2-bath home in the east Highland Park area. Located just a short walk to the vibrant downtown highwood shops and restaurants, as well as to Highwood Metra Station. The famous Morane dog park and beach is also just a skip away. This location is central to everything Highland Park has available. Not

Jeffrey Sklar Beycome Brokerage Realty LLC

Desirable single-family-home in great condition with amazing Highwood location and schools! Sellers have maintained this adorable vintage charmer and made MANY UPDATES, including ALL-NEW KITCHEN (2020), refinished HARDWOOD FLOORS (2020) throughout, and NEWER WINDOWS! One clean, classic bathroom upstairs. Bonus room off the back is perfect for home office, gym or play space. Clean unfinished

Carolyn Cerf @properties Christie's International Real Estate

Welcome to this beautifully updated first floor, two bedroom, two bath condo in the sought after Legacy Club. Offering more than 1,700 square feet of single level living, this home combines generous space, modern comfort, and an ideal layout. Step inside to a bright, open living area featuring hardwood floors, high ceilings, and seamless access to the covered private patio, a year round extension

Carly Jones Engel & Voelkers Chicago North Shore

This stunning two-story, 2nd and 3rd floor condominium home in the heart of Fort Sheridan is one of 12 units in the historic Bakery School, offering a spacious floor plan with 2 bedrooms on the unit's main floor and a beautiful family room/ multi purpose area in the upstairs loft. The second floor entry to Unit 204 opens up to a large living room that features tall north and south facing windows,

Susan Ringel Segal @properties Christie's International Real Estate

Absolutely adorable cottage tucked away on a quiet street in the heart of booming Highwood! This charming 3-bedroom, 2-bath home features a fully renovated basement, updated eat-in kitchen with stainless steel appliances, separate dining area, and a sun-filled living room perfect for everyday living and entertaining. Enjoy beautiful sunset views from the inviting front porch, or relax in the huge

Mada Hitchmough Compass

NEW CONSTRUCTION WITH FIRST FLOOR PRIMARY crafted with impeccable attention to detail, 251 High Street offers modern luxury across three levels of beautifully finished living space. The open-concept main level boasts soaring ceilings, wide-plank floors, and a light-filled living room anchored by a custom fireplace. The chef's kitchen is a true centerpiece, featuring high-end stainless steel

Margie Brooks Baird & Warner

Totally updated in 2025 and move-in ready, this charming ranch blends single-level living with a fully finished basement - and serious income potential. The main level features an open kitchen with breakfast/office space, a comfortable living room, two bedrooms, and a full bath with walk-in shower, all on beautiful hardwood floors. The finished lower level adds a second full bath with tub,

Jim Abbott Baird & Warner

Experience the perfect blend of elegance and contemporary living in this exceptional 1 bedroom + loft condo located in the coveted Tower Barracks East at Historic Fort Sheridan. Overlooking the iconic Parade Grounds, this open and airy second-floor unit is filled with natural light and showcases the architectural details that make Fort Sheridan so distinctive. Inside, you'll find soaring vaulted

Susan Brown Burklin @properties Christie's International Real Estate

First time on the market! Two Units. First and second floor. Vintage home with volume ceilings and hardwood floors. Entry porch leads to the living room, dining room/family room, and large eat-in kitchen. There are two bedrooms, an office and a full bath on the main level. Upstairs there is a two bedroom apartment with a living room, kitchen and full bath. The basement is full and unfinished. The

Carol Santi Coldwell Banker Realty

Exceptional investment opportunity in the heart of downtown ! Perfectly situated on a quiet one-way street within the city's vibrant business district, this beautifully maintained and newly remodeled three-flat has been thoughtfully updated from top to bottom. Each unit showcases stylish new kitchens and baths with modern cabinetry, quartz countertops, updated lighting and fixtures, new tile,

Jim Abbott Baird & Warner

Wonderfully Spacious, Sunny, Brick Home with Lovely Yard Space, in Fort Sheridan! Grand 2-Story Entry Opens to a Huge, Light-Filled Great Room with Soaring Ceilings and Walls of Windows, Flowing into the Large Kitchen with Island and Breakfast Bar and a Separate Eating Area Surrounded by Windows and Flooded with Light. The Main Floor also includes a Formal Living Room, Dining Room, Office with

Janet Borden Compass

A Fort Sheridan gem! This beautifully updated home, just steps from Lake Michigan, seamlessly blends timeless character with today's modern amenities. Sun-filled interiors and generous living spaces make this home ideal for both everyday living and entertaining. The welcoming main level features a dining room and spacious family room connected by a striking two-sided sandstone fireplace, a cozy

Susan Brown Burklin @properties Christie's International Real Estate

Built by experienced Marco Homes and ideally situated on a quiet cul-de-sac in the highly sought-after Highland Park Highlands, this exceptional residence offers the perfect blend of timeless elegance, generous living space, and thoughtful design. Featuring four spacious bedrooms on the second level and two additional bedrooms in the beautifully finished lower level, this home is perfectly suited

Maxine Goldberg Engel & Voelkers Chicago North Shore

Fully rehabbed brick 3-flat on an oversized double lot in the heart of Highwood-an exceptional, turn-key investment opportunity with strong, stable income already in place. This property features two expansive 3-bedroom, 1-bath units (Unit 1 rented at $2,950 and Unit 2 at $2,755) plus a 1-bedroom, 1-bath unit (Unit 3 rented at $1,450), all leased through March 2027 for immediate cash flow and

Jim Abbott Baird & Warner

Welcome to 2648 Western Ave, an exceptional opportunity in one of Highland Park's most desirable locations. Set on a beautiful half-acre lot, this classic brick ranch with a walk-out lower level offers the perfect canvas to create your ideal home or a compelling value-add investment. With 5 bedrooms and 3.1 bathrooms, the home features a functional, flexible layout with strong bones and abundant

Aaron Walsh @properties Christie's International Real Estate

Exceptional investment opportunity or owner-occupied two-flat with both units completely remodeled in 2024. Unit 1 offers 3 bedrooms and 2 full baths featuring hardwood floors, a wood-burning fireplace in the spacious living room, updated kitchen with new refrigerator, in-unit washer/dryer, and a side deck off the dining area. The finished lower level adds a family room and brand new full bath -

Jacqueline Lotzof Compass

Calling all investors & rehabbers- fabulous or opportunity for existing ranch style 2 flat in booming Highwood. Each unit is 2 beds, 1 bath, oversized garage parking and tons of storage, laundry in basement. Property is zoned as multi unit, so tear down and built opportunity available- tons of space to develop the land or improve/expand existing property.

Mada Hitchmough Compass