Highwood Real Estate

Welcome to Highwood, a charming city located in Lake County, Illinois. Known for its small-town feel and friendly community, Highwood offers a unique blend of urban amenities and suburban tranquility.

Highwood is a vibrant city with a rich history and a strong sense of community. Residents enjoy easy access to beautiful parks, top-rated schools, and a variety of local shops and restaurants. The city is also known for its lively events and festivals, including the Highwood Days festival and the Garlic Fest, which attract visitors from near and far.

Located in Lake County, Highwood is surrounded by natural beauty, with plenty of outdoor recreational opportunities nearby. Residents can explore the scenic trails of the nearby parks or enjoy a day on the shores of Lake Michigan, just a short drive away.

With its convenient location and strong sense of community, Highwood is a wonderful place to call home. Whether you're looking for a peaceful suburban retreat or a lively urban experience, Highwood has something for everyone. Come discover all that this charming city has to offer!

Newest Listings in Highwood

$925,000

3 Beds ⋅ 3 Baths ⋅ 12805494 MLS ⋅ NEW Status

Discover the charm and tranquility of historic Fort Sheridan! Situated on the former grounds of the military horse stables, this beautifully updated, approximately 2,800-square-foot townhome is surrounded by tree-lined streets, historic architecture, scenic trails, and walking paths to Lake Michigan and Fort Sheridan's beaches. Featuring 3 bedrooms, 2.5 baths, soaring ceilings, refinished maple hardwood floors, an updated fireplace, and a renovated kitchen with quartz countertops and marble backsplash. The luxurious primary bath offers heated floors, a jetted tub with an in-line heater, and a separate glass shower. Additional highlights include Lutron switches and dimmers throughout, instant hot water in the showers, a skylit loft, and a heated garage with an optional vehicle lift.Enjoy a private, beautifully landscaped, fenced yard and patio, just minutes from Highwood's restaurants, entertainment, and Metra while being part of the Historic charm, modern luxury, and a peaceful North Shore lifestyle! Call Listing Agent for Exclusions

11 Rienzi Lane, Highwood

$250,000

12802213 MLS ⋅ NEW Status

Turnkey Restaurant (Business Sale Only) Opportunity in Downtown Highwood! Fantastic opportunity to own an established, turnkey restaurant business in the heart of Highwood! Located in a vibrant downtown area, this restaurant offers spacious dining areas, and an inviting outdoor patio perfect for additional seating and seasonal dining. Interior features ample seating with booths and tables, a dedicated bar area, and a fully equipped commercial kitchen. All restaurant features and trade fixtures are included in the sale, offering a great opportunity for a new owner to step in and continue operations or bring their own restaurant concept to life. Schedule your private showing today! Showings: 8-9am Monday - Thursday

311 Waukegan Avenue, Highwood

$689,900

3 Beds ⋅ 3 Baths ⋅ 12797321 MLS ⋅ ACTIVE Status ⋅ Fort Sheridan BLDG.

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 pantry. Dining room & living room with gas fireplace, and sliders to the large (14 x 22) deck. The top floor has three bedrooms, & 2 full baths (primary bath with tub & separate shower). The bedrooms all have generous closet space. There are hardwood floors through much of the home, & custom plantation shutters. The unfinished basement provides additional wonderful storage and easy access to utilities. The neighborhood is a gorgeous setting for activities, & convenient access to train, & neighboring downtown Highwood with a multitude of restaurants & year round events. Fabulous opportunity!

701 Lyster Road, Highwood

$649,989

3 Beds ⋅ 2 Baths ⋅ 12780110 MLS ⋅ ACTIVE Status

Every inch of this gorgeous 3-bedroom, 2-bathroom property has been masterfully updated for modern luxury living. Located in an unbeatable North Shore location, you are just steps away from Highwood's acclaimed dining district, boutique shops, parks, seasonal festivals, and the Metra station. The main level welcomes you with a bright, seamless layout featuring newly finished, gleaming pine hardwood floors, brand-new drywall, insulation, and doors throughout. Fresh new flooring carries into both the inviting foyer and the practical rear mudroom. New kitchen designed with premium finishes, it boasts brand-new appliances, sleek cabinetry, and a layout perfect for both daily living and effortless entertaining. Head upstairs to find three spacious, sunlit bedrooms and a beautifully modernized luxury full bathroom complete with premium fixtures and contemporary finishes. The full walk-out basement features independent exterior access, durable epoxy-finished floors, and a second brand-new full bathroom. This massive area offers incredible potential for a home gym, media room, or recreation space. A dedicated, newly added basement laundry room completes this lower level. Brand-new patio floor, a new rear deck, and newly constructed front entrance and back-door staircases. New water heater. Detached 2-car garage. This home is truly turn-key. Move right in and enjoy the ultimate North Shore lifestyle!

225 Burchell Avenue, Highwood

$785,000

4 Beds ⋅ 3 Baths ⋅ 12778830 MLS ⋅ ACTIVE Status

Beautifully nestled in the established community of Highwood and just moments from its charming downtown, 219 Western Avenue offers the perfect blend of modern living, neighborhood character, and North Shore charm. Inside, this home has been thoughtfully reimagined from top to bottom, beginning with a redesigned floor plan created for the way we live today. Beautiful new oak flooring flows throughout the home, complemented by new recessed lighting and fresh modern finishes. At the heart of the home is a stunning oversized kitchen, featuring quartz countertops, stainless steel appliances, a large center island and walk-in pantry-a space designed just as much for gathering as it is for cooking. Conveniently located off the kitchen is a dedicated laundry room with direct access to the attached garage. A main-level full bathroom with new tile surround sits near a versatile bedroom that can easily serve as a private guest room, home office, or flex space. Down the hall, the large living room welcomes you with the warmth of a wood-burning fireplace, creating the perfect setting for cozy evenings at home. Just opposite, a dedicated dining room is ready for holiday dinners, celebrations, and memorable nights around the table. The second floor welcomes you to a master bedroom with a spacious ensuite bathroom and walk-in closet. Down the hall you will find the 3rd bathroom followed by additional bedrooms. Back on the main level, toward the south wing of the home, a spacious bonus room provides yet another place to gather and unwind. New patio doors invite you outside to the newly constructed concrete patio, seamlessly connecting indoor and outdoor living. The transformation isn't limited to the interior, the home features an impressive list of major improvements, including all-new siding, new windows, new roof, two new high efficiency furnaces, new air conditioners, new high efficiency water heater, new garage door and new patio door, offering both beautiful curb appeal and the reassurance of substantial updates already completed. The unfinished basement is a true blank canvas, ready for your imagination-whether you envision a recreation room, home gym, theater, office, additional entertaining space, or simply exceptional storage. Outside, a generous front yard framed by mature pine trees creates a picturesque setting with natural shade and plenty of room for summer gatherings, morning coffee, or simply enjoying the seasons. Beyond the property, enjoy the character and energy that makes Highwood special-from its downtown dining scene and community events, parks and convenient Metra access. Highwood's downtown has evolved over generations into a North Shore dining and gathering destination while retaining the personality of a close-knit community. A home where modern finishes meet established neighborhood charm, with the best of Highwood close at hand.

219 Western Avenue, Highwood

$925,000

3 Beds ⋅ 4 Baths ⋅ 12791534 MLS ⋅ ACTIVE Status

$$BIG SAVINGS$$ BRAND NEW HOME. Qualified buyers could save over $17,000 in mortgage payments during their first two years with a builder paid temporary rate buy down!* Contact the listing agent today for details. **One residence under contract. Four opportunities remain!** Location, Location Location. Walk to Highwood's vibrant downtown, recognized as one of the North Shore's hottest destinations for restaurants, bars, and entertainment. The boutiques, shops, and dining of downtown Highland Park are just minutes away, along with the Highwood Metra station, Lake Michigan beaches, and top rated area schools. Modern architecture. Effortless living. A rooftop experience that changes everything. Welcome to Townhomes on Prairie, an exclusive collection of just five residences offering sophisticated urban modern design and a low maintenance lifestyle in Highwood. With only four opportunities remaining, now is the time to experience this exceptional new development. Each residence features 3 bedrooms, 3.1 baths, and a versatile flex space across thoughtfully designed levels of living. The main living area unfolds across two connected levels, with the kitchen and dining space overlooking the family room with vaulted ceilings and oversized windows. The beautifully appointed kitchen features custom frameless soft close cabinetry with a sophisticated matte finish, sleek thick quartz countertops, a large island, pantry storage, and stainless steel appliances. A powder room adds convenience, while a private balcony off the kitchen extends the living space outdoors. Throughout the home, white oak flooring, custom steel and oak railings, solid core interior doors, and oversized European windows add warmth, refinement, and abundant natural light. Upstairs, the primary suite includes a walk in closet and private bath, complemented by two additional bedrooms, another full bath, and conveniently located laundry. Enter directly from the heated, attached two car garage into a flexible lower level with a full bath and closet. This versatile space is ideal for an office, fitness studio, playroom, guest suite, or media room. At the top, an expansive private rooftop deck offers room for dining, lounging, gardening, and evenings beneath the stars. With electric, water, and gas already provided, it is ready for true outdoor living. High efficiency systems and extensive insulation enhance comfort, energy performance, and sound control throughout the home. Townhomes on Prairie brings together builder Jeff Cohen of Canada & Klein, Ltd., with almost 40 years of experience, architect Peter M. Nicholas of Nicholas Design Collaborative, with 37 years of expertise, and freelance designer Jennifer Liang. Their shared vision combines quality construction, thoughtful architecture, and sophisticated interior design. The result is a distinctive collection where modern comfort, flexible living, and unforgettable private rooftop retreats come together in the heart of Highwood. *Savings vary by residence and financing terms. Subject to lender approval, accepted offer price, and seller agreement. Restrictions apply.

105 Prairie Avenue Unit #105C, Highwood

$849,000

3 Beds ⋅ 4 Baths ⋅ 12791531 MLS ⋅ ACTIVE Status

$$BIG SAVINGS$$ BRAND NEW HOME. Qualified buyers could save over $17,000 in mortgage payments during their first two years with a builder paid temporary rate buy down!* Contact the listing agent today for details. **One residence under contract. Four opportunities remain!** Location, Location Location. Walk to Highwood's vibrant downtown, recognized as one of the North Shore's hottest destinations for restaurants, bars, and entertainment. The boutiques, shops, and dining of downtown Highland Park are just minutes away, along with the Highwood Metra station, Lake Michigan beaches, and top rated area schools. Modern architecture. Effortless living. A rooftop experience that changes everything. Welcome to Townhomes on Prairie, an exclusive collection of just five residences offering sophisticated urban modern design and a low maintenance lifestyle in Highwood. With only four opportunities remaining, now is the time to experience this exceptional new development. Each residence features 3 bedrooms, 3.1 baths, and a versatile flex space across thoughtfully designed levels of living. The main living area unfolds across two connected levels, with the kitchen and dining space overlooking the family room with vaulted ceilings and oversized windows. The beautifully appointed kitchen features custom frameless soft close cabinetry with a sophisticated matte finish, sleek thick quartz countertops, a large island, pantry storage, and stainless steel appliances. A powder room adds convenience, while a private balcony off the kitchen extends the living space outdoors. Throughout the home, white oak flooring and trim, custom steel and oak railings, solid core interior doors, and oversized European windows add warmth, refinement, and abundant natural light. Upstairs, the primary suite includes a walk in closet and private bath, complemented by two additional bedrooms, another full bath, and conveniently located laundry. Enter directly from the heated, attached two car garage into a flexible lower level with a full bath and closet. This versatile space is ideal for an office, fitness studio, playroom, guest suite, or media room. At the top, an expansive private rooftop deck offers room for dining, lounging, gardening, and evenings beneath the stars. With electric, water, and gas already provided, it is ready for true outdoor living. High efficiency systems and extensive insulation enhance comfort, energy performance, and sound control throughout the home. Townhomes on Prairie brings together builder Jeff Cohen of Canada & Klein, Ltd., with almost 40 years of experience, architect Peter M. Nicholas of Nicholas Design Collaborative, with 37 years of expertise, and freelance designer Jennifer Liang. Their shared vision combines quality construction, thoughtful architecture, and sophisticated interior design. The result is a distinctive collection where modern comfort, flexible living, and unforgettable private rooftop retreats come together in the heart of Highwood. *Savings vary by residence and financing terms. Subject to lender approval, accepted offer price, and seller agreement. Restrictions apply.

49 Prairie Avenue Unit #49B, Highwood

$1,390,000

12771320 MLS ⋅ ACTIVE Status

Excellent opportunity to acquire a 6,400-square-foot free-standing retail property in a highly visible North Shore location. This prominent commercial property offers exceptional Sheridan Road frontage, strong street exposure, ample on-site parking, and convenient access to the Metra train station, making it an attractive opportunity for both investors and owner-users. The property features five retail storefronts, providing multiple income-producing spaces and a diverse tenant mix with several long-term established businesses. The existing commercial occupancy offers an investor the opportunity to acquire a property with an established presence in the local business community. Zoned CX - Corridor Mixed Use, the property offers a flexible commercial setting within Highwood's established business corridor. The building provides approximately 157 feet of Sheridan Road frontage, excellent visibility, and 25 on-site parking spaces. Sheridan Road is a prominent North Shore thoroughfare providing daily 5,500 minimum vehicular exposure and convenient connectivity throughout Highwood, Lake Forest, Highland Park, and surrounding communities. Recent traffic studies in the area document strong traffic volumes along the Sheridan Road corridor, further enhancing the property's visibility and exposure. Located directly across from the Fort Sheridan development, the property benefits from a prime location surrounded by residential, commercial, dining, and recreational activity. Highwood is a vibrant and growing North Shore community known for its strong local business environment, popular restaurants and bars, festivals, community events, and ongoing residential and commercial development. The property's proximity to downtown Highwood, the Metra station, Fort Sheridan, and surrounding affluent North Shore communities further enhances its appeal. With prominent Sheridan Road frontage, established tenants, flexible CX zoning, possibility to add residential up, ample parking, and excellent visibility, this is an exceptional opportunity for an investor or owner-user seeking a well-located commercial property in Chicago's desirable northern suburbs.

742 Sheridan Road, Highwood

$590,000

5 Beds ⋅ 3 Baths ⋅ 12762775 MLS ⋅ ACTIVE Status

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 entrance as well as access to the second floor - perfect for extended family, in-law arrangements, or rental income potential. The finished basement includes a cantina, ideal for entertaining, and peace of mind comes easy with the boiler replaced within the last five years, roof and gutters in 2024. Whether you're hosting gatherings or accommodating multiple generations under one roof, this home delivers space, convenience, and versatility at every turn. PLEASE NOTE PHOTOS ARE VIRTUALLY STAGED WITH FURNITURE BUT FINISHES WERE NOT ADJUSTED.

325 Grove Avenue, Highwood

$679,000

5 Beds ⋅ 3 Baths ⋅ 12745835 MLS ⋅ RE-ACTIVATED Status

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 and electrical, doors, and trim. Gorgeous refinished hardwood floors span the entire first floor, complemented by new carpeting throughout the second floor. At the heart of the home is the thoughtfully designed chef's eat-in kitchen, featuring custom cabinetry with under-cabinet lighting, stunning Taj Mahal quartzite countertops and backsplash, and stainless steel appliances. The bright and inviting living room with fireplace flows effortlessly into the dining room, creating a comfortable and spacious setting for both everyday living and entertaining. The versatile floor plan offers 2 bedrooms, a dedicated office, and a full bath on the first floor, plus 3 additional bedrooms and a full bath upstairs. This thoughtfully designed layout provides exceptional flexibility for families, guests, or those who work from home. The large partially finished basement offers tremendous potential, featuring a bonus room, full bathroom, abundant storage, dedicated laundry area, and space that could accommodate a second kitchen and recreation room-ideal for extended living, entertaining, or additional finished space. Outside, enjoy an exceptional 265-foot-deep, fully fenced backyard with a garden and brand-new stone patio, offering an abundance of space to relax, entertain, garden, play, or enjoy summer evenings. The expansive yard provides plenty of room for children to play, outdoor activities, and creating your own backyard oasis. A new asphalt driveway leads to the 1-car garage with a new garage door and opener. Ideally located in Highwood, close to schools, parks, shopping, restaurants, Metra transportation, and major expressways. Fully permitted, extensively renovated, and truly move-in ready-this is a home where quality craftsmanship, elevated finishes, and thoughtful design come together.

339 Prairie Avenue, Highwood

$1,199,000

3 Beds ⋅ 4 Baths ⋅ 12716039 MLS ⋅ PRICE CHANGE Status

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!

251 High Street, Highwood

$549,000

4 Beds ⋅ 2 Baths ⋅ 12654067 MLS ⋅ ACTIVE Status

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.

124 S Central Avenue, Highwood

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Highwood Real Estate

Newest Listings in Highwood

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