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Explore Similar Homes Within 2 Miles of Highwood, IL

  • /54

    $4,795,000

    • 5 Beds
    • 11 Baths
    • 7,053 Sq Ft

    930 S Ridge Rd, Lake Forest, IL 60045

    Step into luxury in this custom built (06) estate nestled on almost 2 gated acres along the historic Ridge Road. With over 11,000 square feet, this meticulously crafted home boasts 6 bedrooms and 8.3 bathrooms, designed both for grand entertaining and comfortable family living. It features graciously scaled rooms with incredible architectural detail, soaring ceilings, elaborate moldings,

    Agent Photo

    Elizabeth Wieneke

    Compass

    (224) 445-2427

    930 S Ridge Rd, Lake Forest, IL 60045
  • /57

    $7,250,000

    • 8 Beds
    • 13 Baths
    • 11,542 Sq Ft

    261 E Onwentsia Rd, Lake Forest, IL 60045

    This stunning East Lake Forest estate combines elegant architecture with natural beauty, sitting on nearly three gated acres in the heart of town. Designed in collaboration with the renowned architect Darcy Bonner in 2010 it's a perfect blend of style, function, and peaceful living with a Santa Barbara vibe. The property is surrounded by beautifully landscaped gardens, native plants, fruit

    Agent Photo

    Elizabeth Wieneke

    Compass

    (224) 480-2922

    261 E Onwentsia Rd, Lake Forest, IL 60045
  • /52

    $1,350,000

    • 5 Beds
    • 3.5 Baths
    • 3,368 Sq Ft

    81 Shawford Way, Lake Forest, IL 60045

    Comfortably ensconced on 1.36 acres in beautiful Lake Forest, this gracious home presents 5 bedrooms and 3.5 baths. Opening to an inviting marble foyer, it offers 12 well-proportioned rooms, with the 1st floor including a thoughtfully designed kitchen leading to a welcoming family room enhanced by a gas fireplace, as well as a 1st floor office/bedroom. The 2nd floor proffers the primary and three

    Joanna Koperski @properties Christie's International Real Estate

    81 Shawford Way, Lake Forest, IL 60045
  • /62

    $3,799,000

    • 5 Beds
    • 6 Baths
    • 10,319 Sq Ft

    855 Sheridan Rd, Highland Park, IL 60035

    Exquisite Custom-Built Georgian home in East Highland Park - Nestled on 2+ picturesque acres above the shores of Lake Michigan, this home is a timeless masterpiece. Julius Rosenwald commissioned Arthur Heun to design this residence on the bluffs overlooking Lake Michigan. Set down a private drive on Sheridan Road on over an acre of table land, one of the original Rosenwald Estate homes offers

    Jacquie Lewis Compass

    855 Sheridan Rd, Highland Park, IL 60035
  • /40

    $3,799,000

    • 6 Beds
    • 7 Baths
    • 6,325 Sq Ft

    282 Linden Park Place, Highland Park, IL 60035

    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

    Linda Levin Jameson Sotheby's Intl Realty

    282 Linden Park Place, Highland Park, IL 60035
  • /28

    $6,250,000

    • 7 Beds
    • 6.5 Baths
    • 7,149 Sq Ft

    111 N Mayflower Rd, Lake Forest, IL 60045

    Rare opportunity to own this beautiful lakefront home on almost 4 acres w/ 300' of Lake Michigan shoreline on coveted Mayflower Road. Located down a tree-lined driveway at the end of a private lane, this stately brick home was built in 1914 and features 7 bedrooms, 6.1 bathrooms, 6 fireplaces, original millwork, high ceilings, a gourmet kitchen, an elevator, a newer slate roof, and wonderful

    Ann Lyon @properties Christie's International Real Estate

    111 N Mayflower Rd, Lake Forest, IL 60045
  • /40

    $4,250,000

    • 6 Beds
    • 9 Baths
    • 9,625 Sq Ft

    1630 Ridge Rd, Highland Park, IL 60035

    First time on the market with only one owner having lived here, you'll find a magnificent stone and brick masterpiece that rests on just under a spectacularly landscaped 1.5 acres. This elegant home lives like a ranch and was designed for entertaining from the inside out. First floor Master suite complete with sitting room, fireplace, wet bar, large WIC, spacious bath with double sinks, steam

    Kim Kelley Baird & Warner

    1630 Ridge Rd, Highland Park, IL 60035
  • /48

    $5,999,000

    • 9 Beds
    • 12 Baths
    • 10,777 Sq Ft

    2441 Woodbridge Ln, Highland Park, IL 60035

    Introducing an exceptional lakefront residence on one of Highland Park's most coveted private lanes. Set on a masterfully landscaped 1.85-acre parcel, 2441 Woodbridge Lane offers a rare combination of privacy, scale, and sophistication-backed by unobstructed, panoramic views of Lake Michigan. This architecturally striking, contemporary home spans approximately 10,000 square feet and has been

    Patrick Milhaupt Jameson Sotheby's International Realty

    2441 Woodbridge Ln, Highland Park, IL 60035
  • /53

    $5,200,000

    • 4 Beds
    • 7 Baths
    • 5,576 Sq Ft

    499 W Old Mill Rd, Lake Forest, IL 60045

    This sprawling Tudor style estate is nestled on nearly 10 enchanting acres. Fully fenced, this amazing property borders a public prairie reserve that has been restored to and beyond the historic Jens Jensen design. The grounds are the design pallet that has created award winning gardens across the entire North-Shore and Wisconsin. Featuring a butterfly garden, an organic potager garden, orchard,

    Donna Mancuso Jameson Sotheby's International Realty

    499 W Old Mill Rd, Lake Forest, IL 60045
  • /61

    $5,500,000

    • 4 Beds
    • 3.5 Baths
    • 4,600 Sq Ft

    147 Central Ave, Highland Park, IL 60035

    Discover a rare gem on Central Ave-this stunning Victorian historic landmark sprawls over 4 picturesque acres, just steps from the pristine shores of Lake Michigan. This unique property, once called the Cornelius Field House, features a beautifully restored main house, a charming gardener's cottage, and a spacious coach house (160 Park Ave), each exuding timeless elegance and character. The main

    Lisa Rome Jameson Sotheby's International Realty

    147 Central Ave, Highland Park, IL 60035
  • /32

    $1,099,900

    • 5 Beds
    • 2.5 Baths
    • 3,222 Sq Ft

    555 W Everett Rd, Lake Forest, IL 60045

    *** DISCOVER TIMELESS CHARM AND MODERN COMFORT IN THIS CLASSIC BRICK HOME LOCATED NEAR THE POLO GROUNDS AREA IN LAKE FOREST *** Set on a beautifully wooded 1.38-acre lot, this property offers incredible privacy and space * Inside, enjoy a refreshed interior with newly painted walls/doors/trim, gleaming Hardwood floors and a well-designed floor plan with generously sized rooms throughout * The

    Anne Stromayer Berkshire Hathaway-Chicago

    555 W Everett Rd, Lake Forest, IL 60045
  • /42

    $1,499,000

    • 5 Beds
    • 5.5 Baths
    • 5,900 Sq Ft

    2005 Keats Ln, Highland Park, IL 60035

    Welcome to 2005 Keats Lane! Tucked away on a serene, quiet lane lined with towering trees and dappled sunlight, this expansive home sits on nearly a full acre of land. Located in sought-after Highland Park, within the award winning Wayne Thomas and Deerfield school districts, this home offers the perfect balance of original and new. Lovingly maintained and impeccably remodeled from top to bottom,

    Daniel Cartalucca Coldwell Banker Realty

    2005 Keats Ln, Highland Park, IL 60035
  • /64

    $1,599,999

    • 5 Beds
    • 5.5 Baths
    • 5,819 Sq Ft

    3464 Old Mill Rd, Highland Park, IL 60035

    WELCOME TO 3464 OLD MILL ROAD - A MASTERFULLY CRAFTED PRAIRIE-STYLE ESTATE INSPIRED BY FRANK LLOYD WRIGHT, NESTLED ON OVER AN ACRE OF A SERENE, PRIVATE, TREE-FILLED LANDSCAPE IN COVETED HIGHLAND PARK. WITH OVER 9,000 SQUARE FEET OF LIVABLE SPACE, THIS RESIDENCE OFFERS A ONE-OF-A-KIND LIVING EXPERIENCE WHERE MODERN FUNCTIONALITY MEETS TIMELESS ARCHITECTURAL BEAUTY. FROM THE MOMENT YOU ENTER,

    Kelly Ipjian Exit Strategy Realty

    3464 Old Mill Rd, Highland Park, IL 60035
  • /7

    $795,000

    • Land
    • 2.10 Acres
    • $378,571 per Acre

    1329 Waukegan Rd, Deerfield, IL 60015

    Rare 2.1-Acre Lot in Prime Deerfield Location. Build your dream home or explore development possibilities on this expansive 2.1-acre lot located in the highly sought-after village of Deerfield. Set amidst beautiful natural surroundings, this property offers an exceptional opportunity for custom construction or investment. With generous frontage and a tranquil setting, the land provides privacy

    Lisa Rome Jameson Sotheby's International Realty

    1329 Waukegan Rd, Deerfield, IL 60015
  • /64

    $3,125,000

    • 6 Beds
    • 5 Baths
    • 5,734 Sq Ft

    450 Hunter Ln, Lake Forest, IL 60045

    Refined Modern Living in the Heart of Lake Forest. Tucked away on a quiet cul-de-sac and set on over an acre of beautifully landscaped grounds, this fully renovated 6-bedroom, 5-bathroom home offers modern comfort and timeless appeal in one of Lake Forest's most desirable neighborhoods. Reimagined in 2025, the home welcomes you with a dramatic two-story entry and a light-filled layout designed

    Antonio Giamberduca Baird & Warner

    450 Hunter Ln, Lake Forest, IL 60045
  • /4

    $1,395,000

    • Land
    • 1.82 Acres
    • $766,484 per Acre

    262 E Foster Place, Lake Forest, IL 60045

    This exceptional 1.82-acre parcel offers an unparalleled opportunity to build your dream home in coveted East Lake Forest. Located on a picturesque street surrounded by impressive estates, this lot is the perfect setting for new construction. Currently, a 4-bedroom, 2.1-bathroom split-level home sits on the property, but the real value lies in the land itself. Fabulous location -- a convenient

    Lisa Trace @properties Christie's International Real Estate

    262 E Foster Place, Lake Forest, IL 60045
  • /77

    $27,500,000

    • 5 Beds
    • 9 Baths
    • 15,000 Sq Ft

    595 Circle Ln, Lake Forest, IL 60045

    Opportunity of a lifetime to own this spectacular Lake Forest estate, spanning over 5.27 acres with 570 feet of Lake Michigan frontage! After four years of construction, incorporating everything the most discerning buyer would expect in new construction, this estate was completed in 2019. Featuring a protected cove beach, 2 boat launches, a fabulous pool, spa, boathouse and garage space for 22

    Ann Lyon @properties Christie's International Real Estate

    595 Circle Ln, Lake Forest, IL 60045
  • /56

    $10,900,000

    • 6 Beds
    • 11 Baths
    • 11,416 Sq Ft

    347 Bluffs Edge Dr, Lake Forest, IL 60045

    Introducing a newly built lakefront estate, Rockland, a rare gem on the shores of Lake Michigan. This property boasts a private white sand beach and a fully equipped beach house. Access the secluded beach via steps or a funicular. Nestled in a serene setting this gated Estate offers a smart home.Built in 2020, the home epitomizes comfort and elegance across three levels of living space. Enjoy

    Houda Chedid Compass

    347 Bluffs Edge Dr, Lake Forest, IL 60045
  • /52

    $2,999,000

    • 6 Beds
    • 6.5 Baths
    • 7,640 Sq Ft

    493 Hazel Ave, Highland Park, IL 60035

    List price is lower than the assessed value so the taxes should go down for the new owner. Why Would You Want Ordinary When You Can Have Extraordinary! This Stunning and Majestic Brick Home Sits on Over an Acre in the Heart of Highland Park and Features a 40' Indoor Pool with a Wall of Glass that Opens to the Outdoors! Over 7600 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement, It Boasts

    Janet Borden Compass

    493 Hazel Ave, Highland Park, IL 60035
  • /3

    $750,000

    • Land
    • 2.13 Acres
    • $352,113 per Acre

    687 W Old Elm Rd, Lake Forest, IL 60045

    Over 2 acre wooded home site backing to Forest Preserve. Unique opportunity to build your custom home!

    Donna Mancuso Jameson Sotheby's International Realty

    687 W Old Elm Rd, Lake Forest, IL 60045
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