Highwood, IL Homes for Sale

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

Charming, thoughtfully updated Colonial in a superb Highwood location - close to everything. 4 Bedrooms & 2 Baths with plenty of room to relax. Full of character and natural light, the home offers warm, comfortable living with functional flow and flexible spaces, ideal for both everyday living and entertaining. Recent improvements include new siding, roof, deck, driveway, fence, front walkway /

Laura McCain Compass

Discover an incredible opportunity in the heart of downtown Highwood! This 3-bedroom, 2-bath home offers unbeatable location and flexibility, perfect for both investors and owner-occupants. The second floor features 3 spacious bedrooms and a full bath, providing a comfortable and functional living space, while the main level offers great potential to customize or enhance to your vision.

Jim Abbott Baird & Warner

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

Charming Home Steps from Downtown Highwood! Welcome to this inviting 3-bedroom, 1-bath home located just steps from vibrant downtown Highwood. Featuring a large kitchen with an attached dining room, this home offers the perfect blend of comfort and convenience. The partially finished basement provides additional living space or room to grow, while the 2-car garage adds valuable storage and

Carol Santi Coldwell Banker Realty

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

Stunning stables home in the heart of Fort Sheridan! One level living! Vaulted ceilings with original beams. Spacious floor plan 3 bedrooms or use as 2 bedrooms plus an office. 2 full bathrooms plus powder room. Generous closet space throughout. Fully fenced in private backyard. Brand new AC unit. 2 car attached garage. Remodeled kitchen!! Gas ventless fireplace in the living room. Mostly

Alison Wertheimer @properties Christie's International Real Estate

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

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

Beautifully updated and move-in ready, this exceptional Fort Sheridan home offers the perfect blend of timeless elegance, modern upgrades, and an unbeatable location just moments from Lake Michigan beaches, nature trails, Metra, restaurants, shopping, and top-rated Highland Park schools. A dramatic two-story foyer welcomes you into sun-filled living and dining spaces, while the updated kitchen

Philip Wrigley Coldwell Banker Realty

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

Discover your dream Condominium just steps away from the serene shores of Lake Michigan, nestled within the beautifully maintained grounds of Fort Sheridan. This expansive luxury condo features soaring 9-foot ceilings, stunning hardwood floors, and elegant recessed lighting, creating a warm and inviting atmosphere. The gourmet kitchen is a chef's delight, equipped with high-end stainless-steel

Ted Pickus @properties Christie's International Real Estate

Experience unparalleled scale and sophistication in this one-of-a-kind Drill Hall residence within a boutique, luxury Fort Sheridan elevator building. Two units, offering an alternative to ranch inspired living, were expertly combined to create this 3 bedroom, 3.2 bath gallery style condominium with the added features of 3 spacious, private balconies overlooking the Meadow and the Pond, 2 loft

Judy Weiss @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