Highwood, IL Homes for Sale with Garage

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

Enjoy the amazing community of Fort Sheridan & this beautiful, East facing, spacious townhome. Over 2600 square feet of living space plus basement, and attached 2 car garage. The entry level has a family room with patio access, laundry/mud room and garage access. The 2nd level has great open flow with a private office, Kitchen with breakfast area, stainless steel appliances, plus a walk-in

Vicki Tenner @properties Christie's International Real Estate

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

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

Unique 2-Story Townhome in Desirable Fort Sheridan Location. Heated Garage w/ Newly Epoxied Floors & Equipped w/Hydraulic Lift to Park Three Cars. This High Ceiling, Bright and Spacious Home is Elegantly Appointed w/High-end Finishes. Improvements include: Inviting Porcelain Tiled Foyer, Porcelain Power Room, Refinished Maple Hard Wood Floors, Recently Renovated Kitchen w/ Quartz Countertop and

Iris Perea Baird & Warner

Modern architecture. Effortless living. A rooftop experience that changes everything. Welcome to Townhomes on Prairie, an exclusive collection of five residences offering sophisticated urban modern design and a low maintenance lifestyle in Highwood. Each residence features 3 bedrooms, 3.1 baths, and a versatile flex space across thoughtfully designed levels of living. The main living area unfolds

Jennifer Boudreau Compass

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

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

Modern architecture. Effortless living. A rooftop experience that changes everything. Welcome to Townhomes on Prairie, an exclusive collection of five residences offering sophisticated urban modern design and a low maintenance lifestyle in Highwood. Each residence features 3 bedrooms, 3.1 baths, and a versatile flex space across thoughtfully designed levels of living. The main living area unfolds

Jennifer Boudreau 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

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

Welcome to Highwood on the North Shore! This approximately 1,904-square-foot Lannon Stone ranch offers flexible living space, hardwood floors throughout, and two fireplaces that add warmth and character. The spacious, and light filled living room overlooks a beautiful park, while the separate dining room with rich slate flooring opens to the patio and connects to the kitchen. The house has

Carol Santi Coldwell Banker Realty

Welcome to this exceptional multi-generational home on a huge lot fenced on three sides, offering the ultimate in privacy and outdoor space in one of the area's most desirable locations. Set just blocks from downtown Highwood and the Metra station, with top-rated schools nearby, this home is designed for flexible living with two full kitchens and a lower level featuring its own private walkout

Jim Abbott Baird & Warner

Rarely available, this updated and meticulously maintained first-floor ranch with a finished lower level offers an exceptional opportunity to enjoy the unique lifestyle of Fort Sheridan. Soaring ceilings and an open living and dining area create a welcoming, light-filled first impression. The inviting living room features a cozy fireplace, a spacious primary suite with a private bath, a second

Stephanie Absler-Orsi RE/MAX Top Performers

UPDATED HIGHLAND PARK RANCH | 3 BEDROOMS | 2 FULL BATHS | OVER 1/2 ACRE | FULLY FENCED BACKYARD | DOG RUN | 2-CAR ATTACHED GARAGE | WHITE-WASHED BRICK & LIMESTONE EXTERIOR | Picture-perfect curb appeal welcomes you to this spacious ranch, where a freshly white-washed brick and limestone exterior creates a crisp, timeless first impression. Set on over half an acre in the desirable Highlands of

Leslie McDonnell RE/MAX Suburban

Step into this completely renovated (by homeowner) and beautifully appointed Fort Sheridan townhome and prepare to be mesmerized. An unobstructed park view sets the stage for this exceptional home, where 11-foot ceilings, sophisticated design, and state-of-the-art technology come together to create a truly one-of-a-kind living experience. The home has been thoughtfully opened up to create an

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

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