Highland Park, IL Homes

• 

  

  

  /15

  $585,900

  • 3 Beds
  • 3 Baths

  602 Old Elm Rd, Highland Park, IL 60035

  Nestled in the heart of a serene neighborhood in Highland Park on phenomenal property, this 3 bedroom, 3 bathroom ranch offers the perfect blend of comfort and convenience. Step inside to discover an inviting open floor plan with spacious room sizes. Features include a primary bedroom with a private ensuite bathroom and a large basement with a flexible floor plan. Sensational south facing

  Margie Brooks Baird & Warner

  602 Old Elm Rd, Highland Park, IL 60035
• 

  

  

  /34

  $1,750,000 Sold Jul 28, 2025

  • 4,690 Sq Ft
  • $373/SF
  • 2 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 2004

  1784 Reserve Ct, Highland Park, IL 60035

  Stunning award-winning Orren Pickell home on nearly one acre features luxury living throughout. The exceptional 5-bedroom, 5.5-bathroom custom estate has oversized rooms, rich architectural details, 3 indoor fireplaces and seamless indoor-outdoor flow. There's a massive eat-in kitchen, equipped with top-of-the-line appliances, custom cabinetry, and a generous island-ideal for entertaining. A

  Lauren Rabin @properties Christie's International Real Estate

  1784 Reserve Ct, Highland Park, IL 60035
• 

  

  

  /25

  Est $906,870 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  211 Green Bay Rd, Highland Park, IL 60035

  211 Green Bay Rd, Highland Park, IL 60035
• 

  

  

  /66

  $1,549,000

  • 5 Beds
  • 5.5 Baths
  • 4,750 Sq Ft

  2670 Priscilla Ave, Highland Park, IL 60035

  Fall in love with this exceptional brick home that offers comfort, elegance and versatility. Nestled on a peaceful dead-end street, this move-in ready residence boasts an expansive and thoughtful layout with 5 full bathrooms and 3 master suites. The third floor master suite is a standout space ideal as a home office, gym or private retreat. The heart of the home features a stunning custom kitchen

  Lora Zlotnik American Real Estate Services

  2670 Priscilla Ave, Highland Park, IL 60035
• 

  

  

  /24

  $695,000 Sold Jul 25, 2025

  • 3,675 Sq Ft
  • $189/SF
  • 12 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2007

  572 Vine Ave, Highland Park, IL 60035

  Incredible townhouse close to downtown Highland Park. Built in 2006, this home offers four bedrooms and three and one half bathrooms with a first floor primary suite. The living room boasts 15 feet cathedral ceilings and a fireplace with gas logs. The dining room is combined with the living room and flows into the kitchen. The spacious kitchen offers maple cabinets, granite counter, stainless

  Carly Jones Engel & Voelkers Chicago North Shore

  572 Vine Ave, Highland Park, IL 60035
• 

  

  /36

  Est $574,512 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft

  638 Melody Ln, Highland Park, IL 60035

  638 Melody 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
• 

  

  /32

  $600,000 Sold Jul 25, 2025

  • 2,290 Sq Ft
  • $262/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1954

  537 County Line Rd, Highland Park, IL 60035

  This 4 bed, 2 bath southeast Highland Park mid-century home blends comfort and character with thoughtful updates. Light pours in from every angle of the spacious great room featuring soaring 10-foot vaulted ceilings with exposed beams, pecky cypress walls, gas fireplace with floor-to-ceiling brick surround, and top-down blinds. The dining area flows into an updated kitchen with two-toned

  Deborah Libby @properties Christie's International Real Estate

  537 County Line Rd, Highland Park, IL 60035
• 

  

  /22

  Est $831,434 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,271 Sq Ft

  586 Melody Ln, Highland Park, IL 60035

  586 Melody Ln, Highland Park, IL 60035
• 

  

  /53

  $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
• 

  

  /31

  $1,050,000 Sold Jul 25, 2025

  • 3,230 Sq Ft
  • $325/SF
  • 4 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1951

  346 Sumac Rd, Highland Park, IL 60035

  Move Right in to this beautiful updated 4 bedroom, 4 Bath, plus bonus room and screened in porch home on over .25 acre lot in wonderful neighborhood. This home was totally transformed in 2006 with a well thought out addition and updates. Large Family room, with volume tray ceiling with skylights and Living room both hosting handsome fireplaces with dinning room perfectly placed between the two

  Ted Pickus @properties Christie's International Real Estate

  346 Sumac Rd, Highland Park, IL 60035
• 

  

  /31

  Est $919,514 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,425 Sq Ft

  373 Flora Place, Highland Park, IL 60035

  373 Flora Place, Highland Park, IL 60035
• 

  

  /58

  $1,875,000

  • 6 Beds
  • 6.5 Baths
  • 5,000 Sq Ft

  215 Prospect Ave, Highland Park, IL 60035

  Stunning Howard Van Doren Shaw English Arts and Crafts home on over an acre of magnificently landscaped property, one and a half blocks from Lake Michigan. Fine architectural detailing throughout, including the 2017 renovated kitchen completed with a butler's pantry and a coffee bar. Wonderful coach house with 4 garage bays, a full 2-bedroom in-law suite, or a fully functioning office,

  Maxine Goldberg Engel & Voelkers Chicago North Shore

  215 Prospect Ave, Highland Park, IL 60035
• 

  

  /35

  $905,000 Sold Jul 23, 2025

  • 3,500 Sq Ft
  • $259/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1896

  385 Vine Ave, Highland Park, IL 60035

  Two Homes for the price of One in East Highland Park. An incredible opportunity awaits in East Highland Park. Two charming homes on one property. Perfectly located near top-rated schools, the lake, downtown, and the train. Main home: Classic 2 story farmhouse(1896)with timeless character. 3 bedrooms on 2nd floor plus 1st floor bedroom/library. 3 full bathrooms. Spacious dining room with

  Joe Giampa Coldwell Banker Realty

  385 Vine Ave, Highland Park, IL 60035
• 

  

  /20

  Est $639,889 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  339 Green Bay Rd, Highland Park, IL 60035

  339 Green Bay Rd, Highland Park, IL 60035
• 

  

  /52

  $2,999,000

  • 6 Beds
  • 6.5 Baths
  • 8,256 Sq Ft

  493 Hazel Ave, Highland Park, IL 60035

  The assessed value is $3,627,762. and that is what the tax bill is based on. The taxes have been appealed and should go down substantially 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

  Janet Borden Compass

  493 Hazel Ave, Highland Park, IL 60035
• 

  /2

  $910,000 Sold Jul 22, 2025

  • 3,914 Sq Ft
  • $232/SF
  • 7 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  3105 Warbler Place, Highland Park, IL 60035

  Welcome to this beautifully maintained all-brick colonial, perched on a hill at the entrance of a friendly cul-de-sac. With timeless curb appeal and a spacious 3-car garage, this home offers a blend of classic beauty and modern comfort. Step through the bluestone front entry into a stunning two-story foyer filled with natural light. To your left, a generously sized dining room is perfect for

  Carol Gooze @properties Christie's International Real Estate

  3105 Warbler Place, Highland Park, IL 60035
• 

  

  /44

  Est $641,153 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  375 Green Bay Rd, Highland Park, IL 60035

  375 Green Bay Rd, Highland Park, IL 60035
• 

  

  /30

  $2,250,000

  • 3 Beds
  • 2.5 Baths
  • 4,317 Sq Ft

  1789 Green Bay Rd Unit B, Highland Park, IL 60035

  Exquisite North Shore Penthouse: The Ultimate Luxury Retreat for the Discerning Executive and Empty Nester! Experience the pinnacle of sophisticated living in this stunning penthouse, one of the most exceptional residences on the North Shore. Designed for those who appreciate quality and detail, this remarkable home features custom high-end finishes that truly must be seen to be fully

  Brad Blumenthal Compass

  1789 Green Bay Rd Unit B, Highland Park, IL 60035
• 

  

  /3

  $511,000 Sold Jul 21, 2025

  • 1,832 Sq Ft
  • $279/SF

  • 3 Beds
  • 2 Baths
  • Built 1962

  1690 Edgewood Rd, Highland Park, IL 60035

  Charming Split-Level Home in Prime Highland Park Location. Welcome to this well maintained 2400 sf. 3-bedroom, 2-bath split-level gem offering the perfect blend of space, comfort, and convenience. With two distinct living areas, this home is designed for both easy everyday living and effortless entertaining. The home, albeit needing an update is in very good condition. Step outside to a

  Gus Karigan @properties Christie's International Real Estate

  1690 Edgewood Rd, Highland Park, IL 60035
• 

  

  /5

  Est $912,849 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  232 Green Bay Rd, Highland Park, IL 60035

  232 Green Bay Rd, Highland Park, IL 60035
• 

  

  /10

  $799,000

  • 4 Beds
  • 1.5 Baths
  • 2,500 Sq Ft

  2542 Green Bay Rd, Highland Park, IL 60035

  Incredible Highland Park Location With Double-Lot & Coach-House Near Metra-Rail & Downtown Retail With Convenience To 41/94 Highways & Always Immaculate With Additional 5-Car Parking For Possible Tenants Above Garage Is 1-Bedroom & Coach-House Will Convert To 2+Bedroom (Note: Main House Has Darling 4-bedrooms & Full-Bath Without Master)

  Sheryl Fisher Coldwell Banker Realty

  2542 Green Bay Rd, Highland Park, IL 60035
• 

  

  /31

  $825,000 Sold Jul 18, 2025

  • 2,112 Sq Ft
  • $391/SF
  • 1 Day On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  1688 Green Bay Rd Unit 303, Highland Park, IL 60035

  Rarely available Condo located at Boutique building in downtown Highland Park. This original owner home is designer decorated and continuously maintained. Two bedrooms plus a den(third bedroom) and two and a half bathrooms. Recently decorated Primary Suite offers two walk-in closets that are both custom fitted. Eat-in Kitchen and the Den is located off the Living Room and Dining Room. Outdoor

  Karen Skurie Baird & Warner

  1688 Green Bay Rd Unit 303, Highland Park, IL 60035
• 

  

  /20

  Est $827,338 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,254 Sq Ft

  312 Charal Ln, Highland Park, IL 60035

  312 Charal Ln, Highland Park, IL 60035
• 

  /2

  $290,000

  • Land
  • 0.22 Acre
  • $1,318,182 per Acre

  0 Skokie Ave, Highland Park, IL 60035

  EAST HIGHLAND PARK BUILDABLE LOT 52 X 183 (9,583 sf).MAX F.A.R=35.83; BONUS F.A.R.=38.83; MAX FLOOR AREA (SF) =3,433; MAX W/BONUS F.AR. = 3,721. CLOSE TO SHOPS, RESTAURANTS, SCHOOLS, METRA AND WONDERFUL LAKE MICHIGAN.

  Carol Santi Coldwell Banker Realty

  0 Skokie Ave, Highland Park, IL 60035
• 

  

  /30

  $810,000 Sold Jul 18, 2025

  • 3,200 Sq Ft
  • $253/SF
  • 16 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1965

  137 Hiawatha Trail, Highland Park, IL 60035

  Experience the perfect blend of comfort, style, and convenience in this impeccably renovated and thoughtfully expanded 4 Bedroom, 4 Bathroom home, nestled on almost 1/2 an acre in a serene, country-like setting-yet just moments from shops, the Metra train, the Chicago Botanic Garden, and more. This sunlit home showcases an expansive open floor plan anchored by a beautifully updated gourmet

  Melissa Newman @properties Christie's International Real Estate

  137 Hiawatha Trail, Highland Park, IL 60035
• 

  

  /22

  Est $963,286 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,150 Sq Ft

  322 Charal Ln, Highland Park, IL 60035

  322 Charal Ln, Highland Park, IL 60035
• 

  

  /36

  $1,299,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 3,900 Sq Ft

  2514 Hidden Oak (Lot 9) Cir, Highland Park, IL 60035

  THIS BEAUTIFUL HOME IS JUST STEPS AWAY FROM A TRANQUIL OASIS W/ NATURE AND WALKING PATHS FOR MILES. THIS 1ST FLOOR MASTER, ASTORIA, FEATURES LUXURY FINISHES THROUGHOUT THE HOME! DESIGNED WITH CUSTOM CABINETRY, QUARTZ COUNTER TOPS THROUGHOUT, FIREPLACE, SOLID CORE 8' DOORS, DESIGNER LIGHT FIXTURES, TRAY & CATHEDRAL CEILINGS, AND UPGRADED TRIM PACKAGE W/ EXTENSIVE CROWN & WAINSCOT ALL INCLUDED IN

  John Barry Mc Naughton Realty Group

  2514 Hidden Oak (Lot 9) Cir, Highland Park, IL 60035
• 

  

  /51

  $1,380,000 Sold Jul 17, 2025

  • 4,896 Sq Ft
  • $282/SF
  • 3 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1977

  870 Woodbine Rd, Highland Park, IL 60035

  **MULTIPLE OFFERS RECEIVED, BEST AND FINAL OFFERS DUE VIA EMAIL, SUNDAY, JUNE 8 AT 5PM CST** Looking for a contemporary home but coming up short? This is the one you've been waiting for. Don't miss this fully renovated, light-filled modern home tucked away on a quiet cul-de-sac in desirable Highland Park, with the option of attending either Highland Park or Deerfield High Schools. Situated on a

  Audra Casey @properties Christie's International Real Estate

  870 Woodbine Rd, Highland Park, IL 60035
• 

  

  /44

  Est $1,701,228 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 4,750 Sq Ft

  775 Stonegate Dr, Highland Park, IL 60035

  775 Stonegate Dr, Highland Park, IL 60035
• 

  

  /25

  $1,399,999 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,216 Sq Ft

  1672 Huntington Ln, Highland Park, IL 60035

  New Construction in Coveted Sherwood Forest - Highland Park, IL. Experience luxury living in this beautifully crafted single-family home, located in the highly sought-after Sherwood Forest neighborhood of Highland Park. Thoughtfully designed by a reputable North Shore builder, this residence offers high-end finishes and modern conveniences throughout.The first-floor primary suite features

  Ryan Cherney Circle One Realty

  1672 Huntington Ln, Highland Park, IL 60035
• 

  

  /29

  $505,000 Sold Jul 17, 2025

  • 2,611 Sq Ft
  • $193/SF
  • 7 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1950

  1850 Garland Ave, Highland Park, IL 60035

  Nestled in the sought-after Sherwood Forest neighborhood, this beloved home awaits its next chapter. Perfect for those looking to renovate or build anew on a generous 100X179 lot, this property offers endless possibilities. The adaptable floor plan features lots of living space. There are currently 2 bedrooms and an unfinished upstairs ready for a primary suite. Perfectly positioned in one of

  Neil Gates Chase Real Estate LLC

  1850 Garland Ave, Highland Park, IL 60035
• 

  

  /21

  Est $871,405 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,624 Sq Ft

  848 Timber Hill Rd, Highland Park, IL 60035

  848 Timber Hill Rd, Highland Park, IL 60035
• 

  Price To Be Determined New Construction

  • 3 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  The Astoria Plan at Hidden Oak of Highland Park, Highland Park, IL 60035

  

  McNaughton Development Inc.

  Builder

  1064 Livingston St Unit 37255718, Highland Park, IL 60035
• 

  

  /38

  $1,100,000 Sold Jul 17, 2025

  • 4,185 Sq Ft
  • $263/SF
  • 2 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1911

  794 Dean Ave, Highland Park, IL 60035

  Welcome to this beautifully updated storybook home offering 6 bedrooms, 4.5 baths, and a prime location directly across from Ravinia Elementary and just a block from the Ravinia business district. A welcoming covered front porch with a swing, sets the tone for this inviting residence. Inside, a gracious foyer leads to a sun-drenched family room featuring a fireplace and bar-perfect for

  Debbie Glickman @properties Christie's International Real Estate

  794 Dean Ave, Highland Park, IL 60035
• 

  

  /25

  Est $870,255 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,624 Sq Ft

  798 Timber Hill Rd, Highland Park, IL 60035

  798 Timber Hill Rd, Highland Park, IL 60035
• 

  Price To Be Determined New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  The Essex Plan at Hidden Oak of Highland Park, Highland Park, IL 60035

  

  McNaughton Development Inc.

  Builder

  1064 Livingston St Unit 37255707, Highland Park, IL 60035
• 

  

  /89

  $5,750,000 Sold Jul 17, 2025

  • 7,800 Sq Ft
  • $737/SF
  • 16 Days On Market

  • 5 Beds
  • 7.5 Baths
  • Built 2008

  959 Sheridan Rd, Highland Park, IL 60035

  Experience Coastal Elegance on Lake Michigan, perfectly situated on 1 acre in East Highland Park with 100 feet of private sandy beach. ALL BLUFF WORK JUST COMPLETED BY TOP NORTH SHORE ENGINEERS! Wake up to breathtaking sunrises and UNOBSTRUCTED lake views from every window in this stunning home, designed to blend luxury and comfort seamlessly. Inside, soaring ceilings and floor-to-ceiling windows

  Kelly Dunn Rynes Berkshire Hathaway HomeServices Chicago

  959 Sheridan Rd, Highland Park, IL 60035
• 

  

  /25

  Est $944,799 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,567 Sq Ft

  766 Timber Hill Rd, Highland Park, IL 60035

  766 Timber Hill Rd, Highland Park, IL 60035
• 

  Price To Be Determined New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  The Classic Plan at Hidden Oak of Highland Park, Highland Park, IL 60035

  

  McNaughton Development Inc.

  Builder

  1064 Livingston St Unit 37255677, Highland Park, IL 60035

Showing Results 201 - 240, Page 6 of 18