Highwood Real Estate

Welcome to the charming neighborhood of Highwood, located in Lake County, Illinois. Highwood is a vibrant city with a rich history and a strong sense of community.

Highwood is known for its diverse dining scene, with a wide range of restaurants offering everything from casual eats to fine dining experiences. The city is also home to a variety of shops, parks, and community events, making it a great place to live for people of all ages.

One of the highlights of Highwood is its convenient location. Situated just a short drive away from the shores of Lake Michigan, residents can easily enjoy all that the lakefront has to offer, from beaches to hiking trails. The city is also within easy reach of major highways, making it a convenient location for commuters.

Highwood is a tight-knit community where neighbors look out for one another and come together to celebrate local traditions and events. Whether you're looking for a peaceful place to raise a family or a lively city with plenty of amenities, Highwood has something to offer everyone.

If you're considering making Highwood your home, contact us today to learn more about the real estate options available in this wonderful neighborhood.

Newest Listings in 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

$1,199,000

3 Beds ⋅ 4 Baths ⋅ 12716039 MLS ⋅ ACTIVE 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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