Highland Park, IL Homes

• 

  

  

  /42

  $857,500

  $16K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,622 Sq Ft

  1538 Oakwood Ave, Highland Park, IL 60035

  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,

  Mirella Caputo @properties Christie's International Real Estate

  1538 Oakwood Ave, Highland Park, IL 60035
• 

  

  

  /11

  $2,550 Per Month

  • 1 Bed
  • 1 Bath
  • 873 Sq Ft
  • Apartment for Rent

  555 Roger Williams Ave Unit 407, Highland Park, IL 60035

  Remarks: Welcome to Ravinia Crossing, Highland Park's newest boutique rental building in the heart of the Ravinia Business District. This intimate four story 30-unit building consists of a variety of one and two-bedroom unit floor plans with luxury high-end finishes. open great room with walls of windows- the north facing units have balconies and overlook the ravines, the south and east facing

  Larry Klairmont Twins Realty LLC

  555 Roger Williams Ave Unit 407, Highland Park, IL 60035
• 

  

  

  /29

  $800,000

  Sold Feb 10, 2026

  945 Villas Ct, Highland Park, IL 60035

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Above List Price
  • $348/SF
  • 0 Days On Market

  Current Estimated Value $850,256

  Last Listing Agent Deb Baker Compass

  945 Villas Ct, Highland Park, IL 60035
• 

  

  /2

  Est $842,550

  Not Listed For Sale

  401 Sheridan Rd, Highland Park, IL 60035

  • 3 Beds
  • 2.5 Baths
  • 2,212 Sq Ft
  • Built 1953

  401 Sheridan Rd, Highland Park, IL 60035

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Jane Lee RE/MAX Top Performers
• 

  

  

  /27

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 2,330 Sq Ft

  23 Heritage Dr, Highland Park, IL 60035

  The "Serenity at Heritage" maintenance-free HOA community, situated directly across from the Chicago Botanic Garden, is without parallel in the current North Shore market. Experience the pinnacle of sophisticated living in this stunning new construction ranch. Designed with an airy, open-concept flow, the main level impresses immediately with soaring ceilings and strategically placed skylights

  Marla Fox Compass

  23 Heritage Dr, Highland Park, IL 60035
• 

  

  /22

  $650,000

  Sold Apr 23, 2026

  1320 Ferndale Ave, Highland Park, IL 60035

  • 4 Beds
  • 3 Baths
  • 1,586 Sq Ft
  • Built 1947

  Last Sold Summary

  • $410/SF
  • 5 Days On Market

  Current Estimated Value $664,710

  Last Listing Agent James Carey Forest Bluff Realty

  1320 Ferndale Ave, Highland Park, IL 60035
• 

  

  /41

  Est $2,125,070

  Not Listed For Sale

  100 Lakewood Place, Highland Park, IL 60035

  • 5 Beds
  • 4.5 Baths
  • 5,000 Sq Ft
  • Built 1929

  100 Lakewood Place, Highland Park, IL 60035

  Last Sold Summary

  • 112 Days On Market

  Last Listing Agent Ted Pickus @properties Christie's International Real Estate
• 

  

  /45

  $1,699,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 3,884 Sq Ft

  1620 Ravine Terrace, Highland Park, IL 60035

  Exceptional brick and stucco home perched on one of the prettiest streets in east Highland Park, situated on a gorgeous, nearly half-acre property with stunning fully-fenced and professionally landscaped backyard, now ready for new owners. Start your day with a morning stroll to That Little French Guy for coffee and a croissant, see what's new at the Highland Park Library, then enjoy your walk to

  Cheryl Waldstein @properties Christie's International Real Estate

  1620 Ravine Terrace, Highland Park, IL 60035
• 

  

  /13

  $835,000

  Sold Jan 14, 2026

  378 Oakland Dr, Highland Park, IL 60035

  • 5 Beds
  • 3 Baths
  • 2,845 Sq Ft
  • Built 1925

  Last Sold Summary

  • 7% Below List Price
  • $293/SF
  • 14 Days On Market

  Current Estimated Value $916,358

  Last Listing Agent Ted Pickus @properties Christie's International Real Estate

  378 Oakland Dr, Highland Park, IL 60035
• 

  

  /32

  Est $699,452

  Not Listed For Sale

  537 County Line Rd, Highland Park, IL 60035

  • 4 Beds
  • 2 Baths
  • 2,290 Sq Ft
  • Built 1954

  537 County Line Rd, Highland Park, IL 60035

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Deborah Libby @properties Christie's International Real Estate
• 

  

  /11

  $170,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  891 Central Ave Unit 219, Highland Park, IL 60035

  Affordable Senior Housing in Highland Park! Two-bedroom, two-bath unit in an award-winning elevator building for seniors 62 +. Park views from all windows and engineered wood floors in living areas and both bedrooms. Foyer has coat closet. Kitchen has light-wood cabinetry and white appliances, including a refrigerator, gas range/oven, microwave and dishwasher. Both bathrooms have white fixtures

  Linda Barbera-Stein Coldwell Banker Realty

  891 Central Ave Unit 219, Highland Park, IL 60035
• 

  

  /39

  $2,025,000

  Sold May 26, 2026

  796 Marion Ave, Highland Park, IL 60035

  • 5 Beds
  • 5.5 Baths
  • 4,253 Sq Ft
  • Built 2003

  Last Sold Summary

  • 16% Above List Price
  • $476/SF
  • 5 Days On Market

  Current Estimated Value $1,972,751

  Last Listing Agent Beth Wexler @properties Christie's International Real Estate

  796 Marion Ave, Highland Park, IL 60035
• 

  

  /28

  Est $1,053,304

  Not Listed For Sale

  575 County Line Rd, Highland Park, IL 60035

  • 5 Beds
  • 4 Baths
  • 3,340 Sq Ft
  • Built 1971

  575 County Line Rd, Highland Park, IL 60035

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Tony George Real People Realty
• 

  

  /27

  $649,900

  • 3 Beds
  • 2 Baths
  • 1,746 Sq Ft

  Unlisted Address

  This beautiful home has been extensively updated and features a modern kitchen with premium appliances and gorgeous quartz counters. Updated baths, hardwood floors, newer windows and a newer roof. Gorgeous open floorplan with formal living room with brick fireplace and nice built-ins. Cozy dining room with french doors to neat office, den or playroom. Sliders open to private fenced backyard.

  Connie Hoos Coldwell Banker Realty

  Unlisted Address
• 

  

  /10

  $1,200,000

  Sold May 04, 2026

  520 Sheridan Rd, Highland Park, IL 60035

  • 4 Beds
  • 4 Baths
  • 3,226 Sq Ft
  • Built 1937

  Last Sold Summary

  • 10% Above List Price
  • $372/SF

  Current Estimated Value $1,223,248

  Last Listing Agent Ted Pickus @properties Christie's International Real Estate

  520 Sheridan Rd, Highland Park, IL 60035
• 

  

  /36

  Est $898,143

  Not Listed For Sale

  518 Braeside Rd, Highland Park, IL 60035

  • 3 Beds
  • 2.5 Baths
  • 2,748 Sq Ft
  • Built 1926

  518 Braeside Rd, Highland Park, IL 60035

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Nancy Karp @properties Christie's International Real Estate
• 

  

  /17

  $839,990

  New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 2,072+ Sq Ft

  Sutton Plan at The Bowery of Highland Park, Highland Park, IL 60035

  The Sutton townhome offers three levels of stylish living, complete with a flex room, private patio, deck, and open-concept main living space. With 3 bedrooms, versatile gathering areas, and plenty of room to personalize your lifestyle, this home balances comfort and convenience at every turn.

  M/I Homes Builder

  1700 Old Deerfield Rd Unit 41174123, Highland Park, IL 60035
• 

  

  /35

  $1,260,000

  Sold Jul 30, 2026

  458 Naida Terrace, Highland Park, IL 60035

  • 5 Beds
  • 4.5 Baths
  • 3,284 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $384/SF
  • 10 Days On Market

  Last Listing Agent Beth Wexler @properties Christie's International Real Estate

  458 Naida Terrace, Highland Park, IL 60035
• 

  

  /29

  Est $1,011,258

  Not Listed For Sale

  526 Braeside Rd, Highland Park, IL 60035

  • 3 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 1937

  526 Braeside Rd, Highland Park, IL 60035

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Lori Nieman @properties Christie's International Real Estate
• 

  

  /32

  $1,200,000

  Open Sun 1AM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  2383 Shady Ln, Highland Park, IL 60035

  Fabulous 4-Bedroom Gem (5th bedroom and bath in basement) in a Gorgeous Neighborhood This solid brick home blends traditional details with modern updates throughout. The fully finished basement adds valuable living space, while the large updated kitchen offers abundant cabinet and counter space - perfect for everyday living and entertaining. Kitchen has superb prep space on island in the center

  Elizabeth Bauler Coldwell Banker Realty

  2383 Shady Ln, Highland Park, IL 60035
• 

  

  /37

  $615,000

  Sold Mar 30, 2026

  1177 Ridge Rd, Highland Park, IL 60035

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Above List Price
  • $267/SF
  • 5 Days On Market

  Current Estimated Value $627,089

  Last Listing Agent Stephanie Hofman @properties Christie's International Real Estate

  1177 Ridge Rd, Highland Park, IL 60035
• 

  

  /23

  Est $645,447

  Not Listed For Sale

  71 Indian Tree Dr, Highland Park, IL 60035

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 1949

  71 Indian Tree Dr, Highland Park, IL 60035

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Bryce Fuller Baird & Warner
• 

  

  /58

  $3,350,000

  • 6 Beds
  • 6.5 Baths

  1008 Bob o Link Rd, Highland Park, IL 60035

  Situated on a prime half-acre lot in sought-after East Highland Park, this one-of-a-kind custom residence, completed in 2022, offers a rare combination of timeless architecture, warm contemporary design, and purposeful functionality, all executed with an uncompromising commitment to quality. While striking curb appeal sets the tone from the moment you arrive, the grand circular driveway,

  Joshua Lipton Compass

  1008 Bob o Link Rd, Highland Park, IL 60035
• 

  /2

  $1,400,000

  Sold Dec 09, 2025

  1375 Sheridan Rd, Highland Park, IL 60035

  • 4 Beds
  • 3.5 Baths
  • 3,568 Sq Ft
  • Built 1919

  Last Sold Summary

  • $392/SF

  Current Estimated Value $1,480,824

  Last Listing Agent Brandy Simon Engel & Voelkers Chicago North Shore

  1375 Sheridan Rd, Highland Park, IL 60035
• 

  

  /14

  Est $871,811

  Not Listed For Sale

  142 Lincolnwood Rd, Highland Park, IL 60035

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 1969

  142 Lincolnwood Rd, Highland Park, IL 60035

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Geri Emalfarb @properties Christie's International Real Estate
• 

  

  /18

  $769,990

  New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 1,934 Sq Ft

  Reade Plan at The Bowery of Highland Park, Highland Park, IL 60035

  The Reade townhome offers room to spread out with a flexible first-floor retreat, an open main living level, and a private balcony for outdoor enjoyment. Thoughtfully arranged spaces throughout the home make it easy to live, work, and entertain with ease.

  M/I Homes Builder

  1700 Old Deerfield Rd Unit 41174122, Highland Park, IL 60035
• 

  

  /20

  $440,000

  Sold Mar 03, 2026

  927 Half Day Rd, Highland Park, IL 60035

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1957

  Last Sold Summary

  • 20% Below List Price
  • $407/SF
  • 127 Days On Market

  Current Estimated Value $480,557

  Last Listing Agent Greg Weissman @properties Christie's International Real Estate

  927 Half Day Rd, Highland Park, IL 60035
• 

  

  /29

  Est $1,335,854

  Not Listed For Sale

  565 Cherokee Rd, Highland Park, IL 60035

  • 4 Beds
  • 3.5 Baths
  • 3,680 Sq Ft
  • Built 1939

  565 Cherokee Rd, Highland Park, IL 60035

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Marcia Lyman Engel & Voelkers Chicago North Shore
• 

  

  /30

  $624,900

  Pending

  • 2 Beds
  • 2.5 Baths
  • 2,362 Sq Ft

  190 Leonard Wood S Unit 106, Highland Park, IL 60035

  Rarely available, this updated and meticulously maintained first-floor ranch with a finished lower level offers an exceptional opportunity to enjoy the unique lifestyle of Fort Sheridan. Soaring ceilings and an open living and dining area create a welcoming, light-filled first impression. The inviting living room features a cozy fireplace, a spacious primary suite with a private bath, a second

  Stephanie Absler-Orsi RE/MAX Top Performers

  190 Leonard Wood S Unit 106, Highland Park, IL 60035
• 

  /2

  $4,050,000

  Sold Oct 31, 2025

  1250 Linden Ave, Highland Park, IL 60035

  • 5 Beds
  • 8 Baths
  • 8,152 Sq Ft
  • Built 2008

  Last Sold Summary

  • 4% Below List Price
  • $497/SF

  Current Estimated Value $3,793,365

  Last Listing Agent Beth Wexler @properties Christie's International Real Estate

  1250 Linden Ave, Highland Park, IL 60035
• 

  

  /41

  Est $1,408,355

  Not Listed For Sale

  177 Indian Tree Dr, Highland Park, IL 60035

  • 4 Beds
  • 4 Baths
  • 4,400 Sq Ft
  • Built 1937

  177 Indian Tree Dr, Highland Park, IL 60035

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Michael Kelly Compass
• 

  

  /31

  $775,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,750 Sq Ft

  1752 Mccraren Rd, Highland Park, IL 60035

  Welcome to this beautifully updated 4-bedroom, 2.5-bath split-level home, set on one of the largest lots on the block in sought-after Sherwood Forest. The open floor plan offers spacious, comfortable living with an easy flow between indoor and outdoor spaces. Step outside to a two-story deck overlooking the expansive fenced-in yard-perfect for entertaining, relaxing, or enjoying time outdoors.

  Matt Laricy Americorp, Ltd

  1752 Mccraren Rd, Highland Park, IL 60035
• 

  

  /30

  $677,000

  Sold Jan 30, 2026

  860 Green Bay Rd, Highland Park, IL 60035

  • 4 Beds
  • 4 Baths
  • 2,400 Sq Ft

  Last Sold Summary

  • 12% Below List Price
  • $282/SF
  • 62 Days On Market

  Current Estimated Value $734,302

  Last Listing Agent Shlomo Arel Kale Realty

  860 Green Bay Rd, Highland Park, IL 60035
• 

  

  /32

  Est $1,408,272

  Not Listed For Sale

  215 Pierce Rd, Highland Park, IL 60035

  • 4 Beds
  • 4 Baths
  • 4,836 Sq Ft
  • Built 1928

  215 Pierce Rd, Highland Park, IL 60035

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Lyn Wise @properties Christie's International Real Estate
• 

  

  /47

  $630,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  3319 Western Ave, Highland Park, IL 60035

  UPDATED HIGHLAND PARK RANCH | 3 BEDROOMS | 2 FULL BATHS | OVER 1/2 ACRE | FULLY FENCED BACKYARD | DOG RUN | 2-CAR ATTACHED GARAGE | WHITE-WASHED BRICK & LIMESTONE EXTERIOR | Picture-perfect curb appeal welcomes you to this spacious ranch, where a freshly white-washed brick and limestone exterior creates a crisp, timeless first impression. Set on over half an acre in the desirable Highlands of

  Leslie McDonnell RE/MAX Suburban

  3319 Western Ave, Highland Park, IL 60035
• 

  

  /27

  $940,000

  Sold Sep 18, 2026

  146 Towers Keep, Highland Park, IL 60035

  • 4 Beds
  • 4.5 Baths
  • 4,772 Sq Ft
  • Built 1890

  Last Sold Summary

  • 4% Below List Price
  • $197/SF
  • 10 Days On Market

  Current Estimated Value $1,032,086

  Last Listing Agent Susan Brown Burklin @properties Christie's International Real Estate

  146 Towers Keep, Highland Park, IL 60035
• 

  

  /35

  Est $836,088

  Not Listed For Sale

  145 Blackhawk Rd, Highland Park, IL 60035

  • 3 Beds
  • 3 Baths
  • 1,982 Sq Ft
  • Built 1959

  145 Blackhawk Rd, Highland Park, IL 60035

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Barbara Tarr @properties Christie's International Real Estate
• 

  

  /43

  $1,599,000

  • 5 Beds
  • 4.5 Baths
  • 4,491 Sq Ft

  251 Oakland Dr, Highland Park, IL 60035

  Exceptional location between Braeside and Ravinia! Don't be fooled from the outside-this meticulously maintained home offers nearly 4,500 square feet of beautifully designed living space filled with timeless character. A major 2001 renovation reconfigured the first floor while updating the electrical and plumbing, installing Marvin windows, attaching the 2-car garage, and adding a stunning

  Ted Pickus @properties Christie's International Real Estate

  251 Oakland Dr, Highland Park, IL 60035
• 

  

  /20

  $720,000

  Sold Jun 03, 2026

  719 Burchell Ave, Highland Park, IL 60035

  • 4 Beds
  • 3 Baths
  • 1,669 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Above List Price
  • $431/SF
  • 5 Days On Market

  Current Estimated Value $722,027

  Last Listing Agent Mada Hitchmough Compass

  719 Burchell Ave, Highland Park, IL 60035
• 

  

  /31

  Est $1,150,019

  Not Listed For Sale

  580 Rambler Ln, Highland Park, IL 60035

  • 4 Beds
  • 3 Baths
  • 3,535 Sq Ft
  • Built 1954

  580 Rambler Ln, Highland Park, IL 60035

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Lyn Wise @properties Christie's International Real Estate

Showing Results 121 - 160, Page 4 of 18