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 basement with NEWER LAUNDRY MACHINES. Wonderful layout with circular flow from living room to dining room to kitchen. No central AC but great airflow. Detached 1-CAR GARAGE in great shape with new roof (2023). Water heater (2016), boiler (2013), siding (2014), windows (2012). Great back yard! Wonderful neighbors. Just a couple blocks from Metra, bike path, restaurants, beaches, A+ AWARD WINNING SCHOOLS, library, coffee, shopping, Highwood's summer festivals and more! Unbeatable space, condition, schools and location in an achievable price range. Sold AS-IS.
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, a tiled gas vent-less fireplace and decorative custom built-ins. Natural light fills the entire home. There is ample room for a dining room table and area merges with a custom kitchen that features a peninsula breakfast bar, an island with white granite counter tops and stainless appliances, adjacent dining area/ breakfast room, decorative lighting, and a stamped-tin ceiling that gives the space vintage character. Just outside the unit is a covered patio and your own adjoining beautiful 24 x 17 deck; a lovely space for enjoying your morning coffee, the quiet of a beautiful day, watching an approaching summer rainstorm, the opportunity for year-round grilling, dining and entertaining friends and family. The primary suite includes multiple closets, a private bath with an oversized shower, bathtub, and built-in cabinetry. The second bedroom features an en-suite bathroom and can be used as a guest room, an office, or a private study. Just beyond the living room is a reading nook with a half bath and a stunning custom circular staircase that leads up to the showstopper: a 790-square-foot loft. Vaulted ceilings, eight diagonal solar-powered skylights (and electric shades), and original wood beam trusses overhead frame this amazing space that can be used as a family room, a studio, an office, or a home theater. The loft also features a separate, 35 x 11 foot mixed-use room with two additional skylights; perfect for another office or an exercise room with additional storage capacity. Recent improvements include a new slate roof for the building (2023), and all HVAC elements in the unit have been replaced in the last few years - the upstairs and main floor air conditioning and furnace (2025 and 2026) and water heater (2022). Complete with a two-car heated indoor garage (also with large storage space), this home is the only unit in the building that has three separate entrances - two indoor entrances (on the main floor and the loft) and an outdoor entrance that opens up to the beautiful south-facing deck. The Bakery School is one of Fort Sheridan's treasured properties. Separate PIN #'s for 2 garage spaces and taxes paid on each add $428.62 (total $857.24) So total Taxes = $16,269.24
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 appliances, custom cabinetry, and a dramatic waterfall island. The main level primary suite serves as a private retreat, featuring dual closets and a spa-inspired ensuite bath with heated floors, a double vanity, extensive custom tile, and an oversized walk-in shower. Main-floor convenience continues with a dedicated laundry room, mudroom, and a stylish powder room. Upstairs, find two spacious bedrooms sharing a beautifully appointed hall bath. The fully finished lower level with high ceilings boasts an extraordinary all-glass wine cellar, a huge recreation space with a second fireplace, and a private 4th bedroom with walk-in closets and a full bathroom with an oversized shower. Excellent opportunity to own in a prime location close to Highwood's acclaimed dining, trains, and parks!
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, laundry, and a bedroom with attached bonus room - perfect as a second bedroom, nursery, or flex space - with potential for a separate hall entrance, ideal for an Airbnb or short-term rental (check local zoning rules). Updates include new heat/A/C and appliances (2026), sump pump (2025), and roof (2022), plus a brick driveway for three cars and a two-car garage. Turnkey, flexible, and investor-friendly! Available fully furnished! See floor plans to see forth bedroom option. Currently the fourth bedroom is a walk through.
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 French Doors, Mudroom/1st Floor Laundry and Beautiful Hardwood Floors Throughout. The 2nd Level is just as Impressive with a Gorgeous Staircase Leading to the Open Upper Landing, with Hardwood Floors. Large, Bright Primary Bedroom and Private Bath with Double Sinks, a Soaking Tub and Separate Shower. 3 Additional Bedrooms complete this Level; 1 Ensuite, and 2 with a Shared Bath. Huge, Unfinished Basement with High Ceilings Offers even More Potential for Living and Entertaining Space! This Pristine Home offers a Carefree, Lifestyle in an Incredible Location near the Lake, Metra, Amazing Restaurants and Entertainment and Miles of Walking Trails!
Completely renovated from top to bottom, this exceptional home blends luxury finishes with thoughtful design and everyday functionality. Filled with natural light and featuring soaring ceilings, every detail has been carefully upgraded. The second level offers three spacious bedrooms and two beautifully appointed full bathrooms, all with custom-built closet systems, new carpeting, LED recessed lighting, and stylish Minka Air ceiling fans. The luxurious primary suite features two oversized closets and a spa-inspired bath with heated marble floors, an air-jet soaking tub with heated jets and auto-dry, dual vanities with built-in mirrored medicine cabinets (complete with interior electrical outlets), a premium Kohler Veil smart bidet toilet, and a stunning walk-in shower with multiple body sprays, bench seating, digital temperature controls, and exceptional lighting. The secondary bath is equally impressive with a raised vanity, smart bidet toilet, and digitally controlled shower. The main level showcases beautiful white oak flooring throughout, a welcoming den, formal dining room, powder room, first-floor laundry room, and an oversized walk-in pantry. The dramatic great room features vaulted ceilings, a gas fireplace with a striking stone accent wall, and sliding doors leading to the backyard. The chef's kitchen is designed for both entertaining and everyday living with a large leathered quartzite island, custom white shaker cabinetry extending to the ceiling, gray accent island with abundant storage, under-cabinet lighting, hidden outlets, custom drawer organizers, built-in spice storage, lazy Susan, designer marble backsplash, and premium Thermador, Bosch, and Miele appliances, including a plumbed-in steam oven. The finished lower level offers exceptional flexibility with high ceilings, an additional 4th bedroom, full bathroom featuring heated floors and a steam shower, a second laundry area, and generous storage space. Additional improvements include an updated electrical panel, modern HVAC system, and an oversized 2.5 detached garage equipped with a high speed EV charger outlet and a sprinkler system for the lawn, exquisite Emtek crystal door knobs throughout and digital locks for exterior doors. Outside, enjoy a professionally landscaped, private backyard featuring a spacious bluestone patio with room for both dining and lounge seating, an outdoor gas fireplace, mature arborvitae providing year-round privacy, and ample space for entertaining. This home offers the rare combination of timeless craftsmanship, luxury amenities, modern technology, and an unbeatable layout designed for comfortable everyday living and effortless entertaining. Exceptional Fort Sheridan neighborhood located along Lake Michigan, walk to the beach and into town. Located on a quiet cul-de-sac street.
This fully renovated ranch in Highwood blends clean design with thoughtful upgrades throughout, including a newly finished basement and major 2024-2025 improvements. A bright four-season front porch sets the tone on entry, offering flexible space for a sitting room, office, or mudroom. Inside, the open living and dining area flows naturally into a crisp white kitchen with quartz countertops, stainless appliances, and warm gold accents-balanced, modern, and highly functional. Restored oak hardwood floors run throughout the main level, adding a layer of character that anchors the home. The main-level bathroom has been fully updated with a spa-like feel and refined finishes. Downstairs, the newly finished basement expands the living space with a comfortable family room, new half bath with added shower, and a dedicated wine cellar with dry bar, ideal for entertaining or unwinding. A spacious laundry area with newer machines rounds out the lower level. Behind the scenes, the heavy lifting is already done: new architectural shingle roof, gutters, and guards (2025), new garage door and LiftMaster opener (2025), new hot water heater (2024), updated thermostat (2024), and additional electrical upgrades to the garage. Outside, the fenced yard offers both privacy and usability, with a patio and mature landscaping. An oversized one-car garage and freshly sealcoated driveway provide ample parking. All of this in a location that keeps you close to the lake, Metra, schools, and the restaurants and energy that make Highwood one of the North Shore's most underrated pockets.
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 French Doors, Mudroom/1st Floor Laundry and Beautiful Hardwood Floors Throughout. The 2nd Level is just as Impressive with a Gorgeous Staircase Leading to the Open Upper Landing, with Hardwood Floors. Large, Bright Primary Bedroom and Private Bath with Double Sinks, a Soaking Tub and Separate Shower. 3 Additional Bedrooms complete this Level; 1 Ensuite, and 2 with a Shared Bath. Huge, Unfinished Basement with High Ceilings Offers even More Potential for Living and Entertaining Space! This Pristine Home offers a Carefree, Lifestyle in an Incredible Location near the Lake, Metra, Amazing Restaurants and Entertainment and Miles of Walking Trails!
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. Downstairs, you'll find a walk-out unfinished basement complete with an additional bathroom and exterior access to the yard-ideal for future expansion, storage, or added living space. This property is especially attractive for investors, as there is already a month-to-month tenant in place who would love to stay, offering immediate rental income potential. Situated just steps from vibrant downtown Highwood, enjoy easy access to restaurants, shops, Metra, and all the charm this sought-after community has to offer. Please note: many photos are virtually staged to illustrate the home's potential. Don't miss this versatile and well-located property with endless possibilities!
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 parking. Enjoy everything Highwood has to offer-restaurants, bars, festivals, and community events-all just a short walk away. With close proximity to Lake Michigan, parks, and transportation, this is an ideal location for those who want it all. Don't miss your chance to own a piece of Highwood living!

Highwood is located in Illinois. Highwood, Illinois has a population of 5,204. Highwood is more family-centric than the surrounding county with 38.11% of the households containing married families with children. The county average for households married with children is 36.27%.
The median household income in Highwood, Illinois is $88,913. The median household income for the surrounding county is $97,127 compared to the national median of $69,021. The median age of people living in Highwood is 36.1 years.
The average high temperature in July is 83.1 degrees, with an average low temperature in January of 16.7 degrees. The average rainfall is approximately 36.3 inches per year, with 35.9 inches of snow per year.