Refine Search
Sort by
$4,995,000
9 Beds 14 Baths 12678213 MLS ACTIVE Status
Situated on a prestigious private lane in East Highland Park, this rare lakefront offering is a Mid-Century Modern masterpiece. Designed in 1957 by renowned architect Henry L. Newhouse II for Irving B. Harris, Chicago Philanthropist, this 10,000-square-foot contemporary residence sits on nearly two acres of lush grounds with magnificent, unobstructed views of Lake Michigan. Experience the ultimate wow factor as you enter the dramatic foyer and take in the breathtaking vista. The interior features large expanses of glass and natural light, offering a flexible floor plan that flows effortlessly for entertaining and everyday living. An exquisite foyer leads to custom beveled, imported French Limestone floors and dramatic floor-to-ceiling windows that frame the water. With minimalistic aesthetic, the Chef's Eat-In Kitchen is finished with custom black walnut cabinetry, a wall of granite, gourmet appliances, and a sleek gas fireplace. The home's expansive footprint includes a main floor Primary Bedroom Suite with a secondary Primary Suite on the 2nd level and seven additional Ensuite Bedrooms, providing unparalleled space and privacy. Despite significant renovation since construction, the home still retains the core architectural integrity and mid century character established by Newhouse. For wellness and recreation, an Indoor Pool Pavilion features a Dectron temperature-controlled system, a retractable clerestory roof, a steam room, and a dedicated second kitchen equipped with Viking appliances. Outside, the tranquility of the lakefront setting takes center stage. A sparkling Outdoor Pool overlooks the water, while a private tram and stairs lead down to 150 feet of secluded beach. This is a unique opportunity to own a significant piece of architectural history with unlimited potential on the shores of Lake Michigan!

2441 Woodbridge Lane, Highland Park

$873,500
4 Beds 2 Baths 12699488 MLS ACTIVE Status
A welcoming brick paver walkway leads to a large covered front porch with a hanging porch swing, setting the tone for the warmth and charm you'll find once you step inside this home. This beautifully maintained brick home combines timeless character with modern updates, all situated on an expansive 50' x 220' professionally landscaped, fenced lot, expansive brick paver patio, and a two-car, recently structurally redone detached garage. The interior features hardwood floors, solid oak doors, 9' ceilings, and elegant molding throughout. The thoughtfully designed main level offers an inviting flow, beginning with a spacious living room featuring a cozy fireplace. A dedicated first-floor office provides the perfect work-from-home space, while the separate dining room serves as the heart of the home for gatherings and entertaining. The large eat-in kitchen offers abundant cabinetry, plenty of counter space, a breakfast bar with seating for 3-4, and additional table space. It opens seamlessly to the bright first-floor family room, which has a large window facing the gorgeous yard, creating an ideal layout for everyday living. A full bath is located on the main level. The second floor includes three generously sized bedrooms and a second full bathroom with a walk-in closet. The third floor provides a private fourth bedroom with an adjoining sitting area, making it an excellent retreat for guests, extended family, or a live-in arrangement. The basement is divided into two functional spaces. One side is finished, perfect for a play area, craft room, or a second office, the laundry area, and a convenient toilet-only bathroom. The unfinished portion offers a utility room and excellent storage space. With its classic architectural details, generous living areas, and a convenient location close to shopping, dining, downtown amenities, and commuter rail service, this home is ready to welcome its next owners to add their own personal touch. Improvements include a rehabbed, like-new 2-car garage, a new water heater, washer/dryer, front stoop and hand railings, new windows in the attic, new access to the sewer outflow, and a French drain. Installed a catch basin in the backyard, 2 branch drains, and south-facing downspouts tied to the outflow to the city system. Extensive landscaping throughout. Please note that the fireplace is in "as is" condition. HVAC in "as is " condition. Floor plans provided under "Additional Info".

1538 Oakwood Avenue, Highland Park

$1,150,000
5 Beds 6 Baths 12693363 MLS ACTIVE Status
Nestled on a private property this residence stands as a testament to sophisticated design and timeless elegance. This custom-built residence is poised on a lush, wooded lot, offering a serene backdrop that feels worlds away while remaining moments from the very best of North Shore living. Spanning three finished levels of meticulously curated space, the home features five expansive bedrooms and four full and-two-half baths. The interior architecture is defined by a sense of scale and grace, perfectly suited for both grand-scale entertaining and quiet, private moments. The flow is perfect on the 1st level with a private office and a flexible bedroom/ 2nd office with half baths nearby. A bright Kitchen overlooks the yard and patio and features an island with a large eat-in area. At the heart of the home, the primary suite serves as a true sanctuary, offering generous proportions and a refined atmosphere for relaxation. The lower level is a destination unto itself. Fully finished and designed for wellness and recreation, it boasts a private sauna and steam room-an effortless way to incorporate a spa-like lifestyle into your daily routine. Beyond the property lines, the lifestyle afforded by this location is unmatched. Residents enjoy close proximity to the world-class performances at Ravinia Festival and the pristine sands of Rosewood Beach. This address also offers convenient access to highly regarded local educational institutions, including Braeside Elementary, Edgewood Middle School and Highland Park High School.

201 Aspen Lane, Highland Park

$4,399,000
5 Beds 6 Baths 12501567 MLS ACTIVE Status
NEW CONSTRUCTION luxury single-family home coming soon to Highland Park within sought after Ravinia Elementary School boundaries. Designed for both everyday living and elevated entertaining, the main level features a private home office with striking glass and iron doors, a formal dining room framed by oversized windows, two powder rooms, and an expansive living room that seamlessly opens to the kitchen. A vaulted sunroom overlooks the backyard, filling the home with natural light and creating the perfect indoor-outdoor connection with a COVERED PATIO off the kitchen, sunroom and living room. The true centerpiece is the show-stopping chef's kitchen, complete with a full scullery for additional prep, storage, and seamless hosting. Upstairs, you'll find four spacious en-suite bedrooms, a versatile loft/den space, and a thoughtfully designed laundry room equipped with dual washers and dryers for ultimate convenience. The finished lower level is built for lifestyle and wellness, featuring a fully outfitted exercise room with private spa amenities (sauna and steam), an expansive recreation room, an additional bedroom and full bath, and a flexible bonus space ideal for a playroom, card room, or media lounge with heated radiant floors throughout the entire basement. Offering 6 bedrooms, 6 full bathrooms, and 2 half baths. This exceptional home also includes an attached HEATED 3-car garage and sits on nearly half an acre of flat, usable land. A rare opportunity to own new construction in one of Highland Park's most desirable neighborhoods. PHOTOS ARE RENDERINGS AND OF PREVIOUS PROJECT. DELIVERY END OF SEPTEMBER 2026 *Renderings and plans, etc. are for marketing purposes only; finishes/plans may change at the discretion of Seller. Buyer(s) and their representation to confirm all finishes prior to purchase. Buyer's Broker must attend all showings/appointments.

966 Wade Street, Highland Park

$1,399,000
4 Beds 5 Baths 12696254 MLS ACTIVE Status
Welcome to effortless luxurious living in Highland Park. This stunning custom contemporary 6-year-young home offers 5 spacious bedrooms, 4 half baths, and an open floor plan bathed in natural sunlight from every angle. The flexible floor plan blends style, comfort and functionality. Sunny foyer, soaring ceilings, designer finishes, and fixtures throughout. Sun-filled great room flows into chef`s kitchen with stainless steel appliances, pantry, quartz countertop, and storage. A separate dining room sits just off the kitchen and family room, creating the perfect layout. Ideal for family living and entertaining, plus much more. Beautiful hardwood floors throughout the home with all high-end finishes. A custom staircase leads to the second floor. The primary suite includes remote control window treatments, walk in closet, plus a private deck with Trex flooring. The master bath has heated floors, a large shower, and twin sinks. Three additional spacious bedrooms, 2 with jack and jill bath, plus a hall bath with whirlpool tub. The finished basement adds incredible living space with a full bath, bedroom, and large entertainment room, along with a separate professionally soundproofed area ideal for podcasting, recording, or a quiet home office. The garage features epoxy flooring and slat board walls. The home is recently painted and in impeccably maintained. There is also a shared outside area with a play area, fire pit, and walking path. Truly a fabulous home with more features. Taxes do not reflect any exemptions and may be lower for a qualified buyer.

2009 Skyelar Court, Highland Park

$429,000
3 Beds 2 Baths 12697929 MLS ACTIVE Status
Exceptional space and value in an in-town Highland Park location! This spacious three-bedroom, two-bath condominium offers generous room sizes, abundant natural light, southern exposure, and an oversized private balcony-an excellent opportunity to bring your own design ideas and create a home that reflects your style. A welcoming foyer leads to spacious living and dining areas, while the kitchen features maple cabinetry, a comfortable eating area, abundant storage, and direct access to the balcony. The privately situated primary suite features hardwood flooring, exceptional closet space, plantation shutters, and an en-suite bath with dual sinks, soaking tub, and separate shower. Two additional generously sized bedrooms, both with hardwood flooring, share a spacious hall bath. One features plantation shutters, while the other offers direct balcony access and flexibility as a guest room, home office, or den. Additional highlights include in-unit laundry, excellent storage, a one-car attached garage, and a convenient main-level storage locker. Walk to downtown Highland Park, Metra transportation, Sunset Park, restaurants, shopping, and Lake Michigan. Property conveyed in as-is condition.

1534 Mcdaniels Avenue Unit #3E, Highland Park

$2,599,000
6 Beds 7 Baths 12686426 MLS ACTIVE Status
This Beautiful Home on Over an Acre in the Heart of Highland Park Boasts Soaring Barrel Ceilings over 20' High and 5 Fireplaces. Amazing Home for Entertaining with a Magnificent Great Room, a Banquet-Sized Dining Room with a Butlers Pantry, a Wonderful Screened Porch and a Balcony Overlooking the Backyard- which includes Ravines and a Huge Yard, large enough for a tennis/pickleball court, an outdoor pool and more- Accessed by a Bridge! The Double Island Chefs Kitchen has a Fireplace, Walk-in Pantry, Professional Series Appliances, Dumb-waiter and Way Too Many Features to List! The Main Floor has 3 Bedrooms and 3 1/2 Baths and the Entire 2nd Floor is a Romantic Hideaway Primary Suite with its Own Family Room, Fireplace, Huge Walk-in Closet and Spa-like Bath. There is potential to create a 1st Floor Primary if desired. This Home offers over 8000 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement featuring a 40' Indoor Pool with a Wall of Glass that Open to the Outdoors! 2 Additional Bedrooms and Full Baths, a Massive Workout Room, an Amazing Home Theater, and a Summer Kitchen in the Walkout Basement. 5 Zones of Heat and Air, and a 3+ Car Garage. Located just moments from the Vibrant Shops, Dining, and Cultural Landmarks of Downtown Highland Park, the Metra Train and the Lakefront, this Home offers a Lifestyle of Convenience and Sophisticated Comfort. It's not just a place to live-It's a Place to Thrive. Truly a Must See!

493 Hazel Avenue, Highland Park

$1,095,000
5 Beds 6 Baths 12685702 MLS ACTIVE Status
Move-in ready and expanded center entry colonial 6 bedroom, 5 full bath and 1 half bath home that backs to Centennial Park! First level features hardwood floors throughout, an inviting entry, large dining room perfect for entertaining, formal living room with bay windows that opens to a family room (currently used as an office) with fireplace and sliders to patio/yard. Expansive kitchen features wood cabinetry, granite counters, tumbled stone backsplash, stainless steel appliances and large sunlit eat-in area with vaulted tray ceiling that looks onto yard and park. Huge great room with built-ins and dry bar area leads to 2-car garage with storage room. Second floor features a primary suite with vaulted ceiling, hardwood floors, large walk-in organized closet plus spa-like bath with double sinks, whirlpool tub, large shower and commode closet. Four additional bedrooms all with organized closets and hardwood floors, plus three additional full bathrooms - one en-suite bath and two hall baths - complete this level. Lower level includes recreation room, laundry room, 6th bedroom, full bathroom and plenty of storage. Fully fenced landscaped yard with patio that looks onto Centennial Park. Recent updates include: New roof, exterior siding, gutters & downspouts - 2023; brand new garage door, steel tracks & springs - 2026, new first floor light fixtures - 2026. Ideally located just steps from Danny Cunniff Park and Sleepy Hollow Park, with easy access to tennis courts, pickleball courts, frisbee golf, playgrounds, soccer and baseball fields, Centennial Ice Arena, sledding hill and walking trails.

2925 Parkside Drive, Highland Park

$550,000
3 Beds 4 Baths 12671439 MLS ACTIVE Status
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 natural light. The main level includes a sun-filled living room with a full wall fireplace, a spacious eat-in kitchen, and comfortable bedroom spaces ready to enjoy as-is or thoughtfully update over time. The finished walk-out lower level adds incredible versatility, offering a large family room, additional bedroom or office, full bath, laundry area, and a private-entry in-law suite with a kitchen, 2 bedrooms, and a full bathroom. Ideal for multigenerational living, guest accommodations, or potential rental income, this space truly expands what the home can offer. The expansive lot provides room to garden, entertain, or explore future possibilities, while the location delivers unmatched convenience-just minutes from downtown Highland Park and Highwood, Metra access, parks, top-rated schools, and the lakefront. Whether you're looking to move in and make it your own or unlock its full potential over time, this is a rare opportunity in a location that consistently delivers.

2648 Western Avenue, Highland Park

$3,800,000
7 Beds 7 Baths 12662752 MLS ACTIVE Status
Historic lakefront Queen Anne mansion on Lake Michigan! Set on a private 3/4 acre, surrounded on three sides by park, ravine, and Lake, adding "borrowed landscape". Premier location within the "Fort Sheridan" neighborhood of Highland Park, with parks, nearby restaurants, walking trails, beach, and many cultural activities. NuHaus kitchen overlooks Lake. Gorgeous views everywhere. Master Bedroom retreat w/fireplace and 2 balconies, overlooking Lake to East and Ravine to south. Indoor lap pool with ozone treatment (no chlorine), separate HVAC/air filtration system. Pool area has door/large windows to outside, use year-round! First floor bedroom with full bath for guests. Second floor library and additional family room. Newly finished lower level has wine room, play areas, billiards room, and more. Freshly renovated laundry has a dog shower! Meticulously rehabbed with newer mechanical systems, whole house hospital-grade air purification system. Windows were removed, restored, and returned. Large lawn area for play, plus a path to your private overlook for morning coffee. Bluff is owned and maintained by Forest Preserve and is a designated Dark Sky area- see the stars from your bedroom window. 4 car tandem garage. Choice of elementary school. Lake access is via Forest Preserve trail in ravine or Preserve stairs on south side of ravine. The history! Patton lived around the corner, Teddy Roosevelt spent time here. Stroll or bicycle to restaurants from this thriving community with parks, playgrounds, beach, nature trails, and arts. Is your family Musically talented? Midwest Young Artists has classes, concerts, and opportunities for all school ages. Fine Arts are at the Rotblatt & Amrany Fine Art Studio. Outdoorsy? There are so many nearby water and land activities with Forest Preserves and Park District. Families from all over the world have made this vibrant community home. This is the lifestyle you've earned.

34 Logan Loop, Highland Park

$4,399,900
4 Beds 8 Baths 12659749 MLS ACTIVE Status
Sophisticated new custom built 5 bedroom, 6 full bath & 2 half bath home with guest house, patio, pool & spa located on over 3 acres. This limestone & stucco clad home w/composite terra cotta Spanish roof tiles boasts unsurpassed quality construction by Red Rock Homes & is accompanied w/high-end interior designer finishes by Ilene Chase. Some of the home's highlights include: soaring ceilings, open floor plan, wide plank hardwood floors, custom built-ins, wood-paneled elevator, professional grade appliances, upgraded electrical & Smart home integration system, guest house, 50'x25' outdoor pool & spa. 1st level features a grand foyer w/soaring ceiling, RH brushed brass & crystal tiered chandelier, marble floors & bridal staircase. A formal dining room that is the ideal entertaining space connects to a built-in butler's pantry w/Quartzite counters & antiqued mirror backsplash. Expansive sun-filled great room w/22' ceilings, stone surround wood-burning fireplace that is flanked by custom wood built-ins & French sliders leading to outdoor entertaining areas. The great room leads directly to a gourmet chef's kitchen featuring custom bespoke white cabinetry, Quartzite Iceberg counters & backsplash, professional ss appliances featuring 60" commercial Wolf range w/double ovens, Wolf microwave, Sub-Zero refrigerator/freezer & 2 Bosch dishwashers. A large center island w/Iceberg Quartzite waterfall countertop, prep sink, seating & tons of storage. Wet bar w/custom bespoke dark-stained wood & black cabinetry, Quartzite counter & backsplash, ss hammered bar sink, ice maker, beverage refrigerator plus full-size Sub-Zero designer wine refrigerator. Spacious eat-in area is perfect for large gatherings & opens to a bright 4-season sunroom w/vaulted wood-paneled ceiling & a wall of glass doors that make indoor/outdoor entertaining seamless. Formal powder room w/custom wall covering, vanity w/marble counter & herringbone oval sink & eclectic brass sconces. The private primary wing of the home features a handsome study w/wood & reeded glass French privacy doors, herringbone hardwood floors, wet bar, black marble carved fireplace mantle surround, grass cloth wallcovering & wood coffered ceiling w/smoke eater. The office leads to a secondary formal powder room w/custom wood vanity with double thick block marble countertop, custom wall covering and modern sconces. A luxurious primary suite w/tray ceiling, gas fireplace & sliders that lead to patio & pool areas. Other highlights include a morning bar, dressing area & custom walk-in closet w/ substantial built-ins. Spa-like luxurious primary bath featuring porcelain tile heated floors, double vanities w/quartz countertops, separate make-up vanity, oversized shower w/steam, rain showerhead, wall sprays and sleek touch-style control for Smart bath features, plus Kohler jetted soaking tub w/quartz decking & 2 commode closets, one with urinal. Mudroom w/custom built-ins & back staircase access, plus spacious laundry room is located off the 4 car heated garage w/EV chargers for each space. Completing the 1st level is a full pool bath & changing area w/custom built-in storage, located off the mudroom w/sliders leading directly to rear pool, spa & patio. The 2nd level boasts a catwalk w/magnificent views of the foyer & great room below. 3 additional generous-sized bedrooms all w/en-suite luxurious baths & custom walk-in closets. Plumbed for additional washer/dryer. Lower level features huge rec room, wet bar w/wine fridge, exercise room, dry-sauna, 5th bedroom w/full bath & tons of storage. The ideal outdoor PRIVATE entertaining space features a 9' deep in-ground pool & spa surrounded by expansive 5,000 sq. ft. porcelain tile patio decking, built-in fire-pit & outdoor BBQ grill w/stone surround & honed bluestone countertop. An 1,100 sq ft guest house provides guests privacy with sitting/rec room, full kitchen, bedroom w/en-suite bath, laundry & changing area. A rare opportunity to own this brand-new home!

2665 Bentley Road, Highland Park

$700,000
5 Beds 3 Baths 12657575 MLS ACTIVE Status
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 - perfect for additional living space. Unit 2 is a bright 2 bed/1 bath with brand new hardwood floors throughout, open-concept living and dining, fully renovated kitchen with quartz countertops, white cabinetry, stainless appliances, new in-unit W/D, and new HVAC. Both units include 1 interior and 1 exterior garage space. Steps to Metra (Highwood Station 0.4 mi), top-rated North Shore District 112 schools, shopping, and dining. A rare chance to own a fully updated, income-producing asset in one of the North Shore's most desirable communities.

2490 Green Bay Road, Highland Park

$799,000
2 Beds 2 Baths 12624604 MLS ACTIVE Status
Modern Parisian-Inspired Carriage House Steps from Downtown Highland Park Fully renovated down to the studs, this unique carriage house blends historic charm with modern design and amenities. The primary living space is located on the second floor and features vaulted ceilings with steel collar ties, exposed brick walls, and an open-concept layout ideal for entertaining. Chef's kitchen includes custom inset cabinetry and Thermador appliances. Loft area provides flexible space for additional sleeping or office use. In-ceiling speakers throughout main living area. Primary suite offers a spa-like bathroom with curb-less walk-in steam shower, dual vanities, and heated floors. Additional features include in-unit washer and dryer and a 2-3 car radiant heated garage. First floor includes a separate studio/office space with private entrance, full bathroom, kitchenette, and radiant heated floors, ideal for home office, guest suite, or potential rental use. Prime location near downtown Highland Park, shopping, dining, and transportation.

1619 Mcgovern Avenue, Highland Park

$2,699,900
6 Beds 7 Baths 12604911 MLS ACTIVE Status
Stunning Custom Contemporary on Coveted Double Lot in Highland Park designed, built and meticulously maintained by the current owners. This one-of-a-kind home sits on over an acre on a beautiful ravine on one of Highland Park's most sought after streets - just steps from town, top-rated schools, the Lake, parks, and more. With soaring ceilings and expansive open living spaces, the home offers an elegant yet comfortable layout perfect for both everyday living and entertaining. This gourmet cook's kitchen features high-end appliances, abundant cabinetry, a walk-in pantry, and seamless flow into the main living areas, which includes a large open great room/family room off the kitchen and separate dining area with huge walk in closet for all your hosting accessories. Unique shelving niches and art display areas abound. The first-floor primary suite is a private retreat with a spa-inspired bath and a spacious custom walk-in closet. Flexible den/office opportunity perfectly located next to the primary suite and an additional bedroom and a custom built office that can be used as a bedroom round out the first floor. Upstairs, you'll find three generously sized bedrooms, each with direct access to beautifully appointed bathrooms. Off the bedrooms is an expansive open family space perfect for relaxing, reading and playing. The walk-out lower level is a true showstopper - featuring a custom golf simulator room, media/rec space, fitness area, a luxe bath and sauna, and one of the finest indoor basketball and multipurpose sport courts in the area. A professionally landscaped, south-facing backyard offers an in ground hot tub, privacy and room to play, and the attached three-car heated garage adds convenience and comfort year-round. This thoughtfully designed home is a rare and special opportunity in Highland Park - offering abundant space, superior quality, and suburban lifestyle in an unbeatable close to town location.

282 Linden Park Place, Highland Park

$6,750,000
5 Beds 9 Baths 12455514 MLS ACTIVE Status
Located in the coveted Belle Avenue Historic District, this extraordinary estate sits on 2.3 acres of manicured grounds with sweeping lake views. Fully renovated and expanded, the residence blends timeless elegance with modern luxury for a truly one-of-a-kind offering. This five-bedroom, eight full and one half bath home showcases craftsmanship of the highest caliber, including a brick exterior, slate tile roof, extensive millwork, crown moldings, built-ins, hardwood floors, expansive windows, soaring ceilings and graciously scaled rooms. No detail was spared in the complete gut renovation and thoughtful addition that restored and elevated this classic beauty. A welcoming foyer leads to a grand living room, perfect for entertaining, with a limestone fireplace, custom built-ins and a wet bar. The living room opens to a light-filled sunroom with three sets of floor-to-ceiling sliders, seamlessly connecting to multiple outdoor entertaining spaces with endless lake views. A formal dining room with herringbone wood floors, custom wallpaper and a crystal chandelier adjoins to a butler's pantry featuring two wine fridges, custom cabinetry and marble counters. The chef's kitchen is a showstopper, with bespoke inset white wood cabinetry, Quartzite counters, decorative marble backsplash, oversized island with prep sink and seating, professional-grade appliances and a walk-in pantry. A spacious eat-in area has 2 sets of sliders that lead to the bluestone patios. The kitchen opens to a large sunken family room that is a perfect gathering spot for family and friends. Additional highlights of the main level include a sophisticated powder room, mudroom with slate flooring and built-ins, full bath, package receiving room and heated three-car garage. Upstairs, the primary suite is a private sanctuary with a cozy sitting area, custom built-ins, dual walk-in closets and a spa-like marble bath featuring vaulted ceilings, a soaking tub, expansive shower, and breathtaking lake views. Four additional bedrooms each include luxury en-suite baths and walk-in closets with custom built-ins. A second-floor laundry with two washer/dryer sets plus a coffee/bar station on the landing outside the family bedrooms add delightful convenience. The third floor, with its vaulted ceiling and abundant natural light, offers a large bonus room with wet bar, office space, home gym/Pilates studio and full bath. The lower level provides flexible living space with a recreation room, game room, sitting area, guest bath and extensive storage. The outdoor spaces are equally impressive, with bluestone patios, a stone fire pit, built-in bar with seating and pristine landscaping overlooking the ravine and lake. This property combines unmatched craftsmanship, spectacular grounds and iconic lakefront vistas-all within close proximity to the lakefront, schools and town. This is a rare opportunity to own a one-of-a-kind stately residence on a stunning property.

117 Belle Avenue, Highland Park

$1,780,000
6 Beds 6 Baths 12553390 MLS PRICE CHANGE Status
Spectacular Historic Queen Anne Revival on Nearly 3/4 Acre in East Highland Park. A rare opportunity to own a magnificent Queen Anne Revival residence, beautifully set on a private lot just under 3/4 of an acre in sought-after East Highland Park. This exceptional home offers the best of all worlds-historic beauty and grandeur paired seamlessly with modern additions and amenities designed for today's living. Meticulously maintained and thoughtfully expanded, the home features two outstanding additions including a dramatic two-story family room, a luxurious primary bedroom and spa-quality bath, a gorgeous paneled library, and a screened porch, creating a home that lives effortlessly while honoring its architectural heritage. This is a historic home that does not feel old. Upon entry through the charming front vestibule with original leaded glass windows, you are welcomed into a grand foyer showcasing a stunning historic staircase, flanked by the formal living and dining rooms. Original oak flooring runs throughout, adding warmth and authenticity. The living room features a beautiful historic mantle and updated double French doors that open to the rear terrace. Beyond lies the richly paneled library, complete with a hidden bar closet and refrigerator, and access to the screened porch-perfect for relaxing or entertaining. On the opposite side of the foyer, the formal dining room flows into the open kitchen, which is exceptionally equipped with a commercial-grade range, double ovens, dual dishwashers, breakfast area, and seamless connection to the two-story family room with a second fireplace and French doors to the terrace-an ideal layout for everyday living and hosting on any scale. The second floor is anchored by a truly extraordinary primary suite, offering space and luxury beyond expectations. The marble-clad primary bath features a double-bowl vanity, whirlpool tub, oversized separate shower, and private water closet. The bedroom boasts a tray ceiling, an expansive walk-in closet with professionally installed organizers, and an additional cedar closet. This level also includes two additional family bedrooms, two full baths, and a dedicated laundry room. The third floor provides three additional bedrooms, a full bath, and an office-ideal for extended-stay guests, a private living suite, or flexible work-from-home needs. The partially finished basement includes heated flooring, exterior access near the mudroom, and generous cubby storage for active lifestyles. An additional unfinished basement area offers abundant storage. The professionally landscaped yard features sprinklered perennial plantings, a fenced garden area, and ample space for outdoor enjoyment. Additional highlights include a second rear staircase, three-car garage, whole-home speaker system, zoned heating and air, excellent insulation, and a highly efficient layout that makes this large home remarkably manageable. Third-floor utilities are zoned separately and can be shut off when not in use. The home's original foundation has been reinforced with structural steel and is exceptionally solid; remaining foundation areas are newer. Original windows are in place. The property is listed on the National Register of Historic Places, built for prominent Highland Park resident Ross J. Beatty. An extraordinary residence combining history, scale, comfort, and location-just minutes to town and train.

1499 Sheridan Road, Highland Park

$3,250,000
12553280 MLS ACTIVE Status
This two-story, plus basement commercial building located in downtown Highland Park is available for sale. Completely rehabbed in 2007, this 8,750 square foot property is situated near the corner of Sheridan Road and Central Street. This offering is the perfect opportunity for a user or investor to own a highly visible property on one of the main commercial thoroughfares. Located in the heart of Highland Park's Central Business District, this property benefits from easy access to public transportation, the Metra train station and the Edens Expressway. Highland Park is an affluent suburb located approximately 23 miles north of Chicago in the heart of the North Shore. The suburb is known for its vibrant downtown business district, numerous local boutiques, restaurants, a growing residential community with close to new or recently constructed units and is home to the Ravinia Festival.

1913-15 Sheridan Road, Highland Park

$99,000
12526552 MLS ACTIVE Status
Highland Park Tobacco Store - Prime Downtown Location, in the heart of downtown Highland Park, within the vibrant shops and restaurant corridor. Established store offers exceptional visibility and convenience, directly across from the Highland Park Metra Train Station. A true one-stop shop for all tobacco needs provides a wide selection of premium cigars and brand-name products, Tobacco, hookahs, and a full line of accessories, well-appointed cigar room for customers to browse and enjoy, monthly gross sales of $30,000-$35,000, inventory valued at approximately $100,000 (additional). Goodwill, fixtures, features, and equipment included in the sale. A strong opportunity to acquire a well-located, fully equipped tobacco business in a high-traffic downtown setting. Gross monthly rental amount of $3,300.

1621 Saint Johns Avenue, Highland Park

$3,000,000
12512041 MLS ACTIVE Status
Available for sale is a 22,727 square foot two-story medical office building in HIghland Park, IL. The property consists of 18 office suites and has multiple long-term tenants. Situated near the corner of Elm Place and St. Johns Avenue in vibrant downtown area, this property benefits from its location just a block away from the the Metra Train Station and public transportation. Additional parking is available from the easement with the adjacent lot to the south. Area features significant barriers to entry, with few available sites for purchase Highland Park is an affluent suburb located in approximately 25 miles north of Chicago in the North Shore. The city has a vibrant downtown with shopping, restaurants and more.

480 Elm Place, Highland Park

$3,750,000
12320966 MLS ACTIVE Status
Unique Masonry Commercial mixed use, Retail, Office buildings in Highland Park, Extremely rare offering here, 3 Buildings at 2666,2652,2648 Waukegan, in Highland park IL B1-A Zoning, One Auto and Truck repair facility at 2666 Waukegan, Ceiling height of approx. 16FT 4 DID's, Triple catch basins,4959 SQ FT. One Story office Flex warehouse auto body repair building at 2652, Ceiling height 13 FT, 2 DID's, 3, 000 SQ FT and the 2 story mixed use building at 2648 Waukegan 2 DID's, 4608 SQ FT , Upstairs unit is a 3 Bedroom 1 Bath Apartment, and the rear storage yard, - 16,782 SQ FT Prime Location, excellent Exposure Right at the Entrance to the Highwood shopping and entertainment district, The buildings sit between Bloom street and Highwood Ave, 5,500 Cars pass this location a Day On Waukegan Rd (VPD) Full fire alarm Full sprinkler System, Lot Dimensions are 315.04X200105X370X30X570 3 curb cuts on Waukegan road, 200 sq ft OF Frontage on Waukegan, The Buildings have a Great signage area, classic facade, 200 Amp electric, High security Entrance doors, and cameras. The Combined building square footage IS 12,567 FT and the combined Landsite Square footage is 39,232 SQ FT. The property presents the unique opportunity to acquire stand-alone Commercial buildings in Highland Park. Great demographics. Ideal for a variety of commercial uses, Possible Redevelopment to Multifamily or Commercial Mixed use with Zoning Change, Owner user or Investment, Office or professional use, Atty, Architect Accountant, Medical, Podiatrist, Physiatrist, real estate, Mortgage, insurance Possible contractor Use, retail, School, Surrounding Area companies and business include. La Michoacana Bella, Miramar Bistro, Greenwood American Kitchen & Bar, SLYCE Coal Fired Pizza Company, Del Rio Restaurant, Walgreens, La Casa de Isaac Restaurant Longitud315,. Near the Highland Park Metra train stop, and the Highwood Metra train stop, Bus, Close access to area highways, Route 41 and 94 Pin numbers are - 16154140110000 for 2666 Waukegan and 1614311005-0000 for 2652 Waukegan And 16143110060000 for 2648 Waukegan Rear storage lot pin numbers - 1615400001 - 1614300004 Do not bother tenant, Call Listing broker for all showings PLEASE NOTE - OWNER IS NEGOTIABLE ON PRICE AND WILL LOOK AT ALL OFFERS WITHIN REASON.

2648-2666 Waukegan Avenue, Highland Park

$3,900,000
12283503 MLS ACTIVE Status
For sale 660 LaSalle place, masonry mixed use loft building in Highland park, Building is 20,301 sq ft, 17,566 sq ft, of land, completely rehabbed, The Zoning is RM1; Current available units measure from 2209 sq ft to 4650 sq ft, open space/units feature exposed brick walls, high end finishes, high ceilings with hardwood oak floors or carpet, very bright, modern lighting, skylights, Wi-Fi access, units typically include kitchen, bathrooms and foyer, office units have privately controlled HVAC, and 24 access, open floor plans for some units an excellent and very rare transit oriented redevelopment opportunity. Building can be left as a loft office building or redeveloped into an apt bldg. or repurposed into high ceiling condos, Parking for 20 cars, building is located walking distance to downtown highland park, shopping, restaurants, parking, Metra train stop. Do not Bother tenants, Call listing broker for showing, 660 Lasalle Parking lot Pin next door 1626201001

660 La Salle Place, Highland Park



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.