Highland Park, IL Homes

• 

  

  

  /34

  $539,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 1,460 Sq Ft

  348 Park Ave, Highland Park, IL 60035

  Offer accepted and waiting for relocation company to sign it, no showings at this time. Prime Downtown Highland Park Location! Beautifully updated end-unit townhome that lives like a single-family home, offering an open floor plan, abundant natural light, and move-in-ready condition. The main level features hardwood floors, recessed lighting throughout, and a well-appointed kitchen with stainless

  Chris Veech @properties Christie's International Real Estate

  348 Park Ave, Highland Park, IL 60035
• 

  

  

  /5

  $2,384 Per Month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Brand-New 1 Bedroom in Downtown Highland Park | Private Terrace | Steps to Metra

  1770 1st St Unit 504, Highland Park, IL 60035

  Be the first to live in this beautifully renovated 1-bedroom apartment in the heart of downtown Highland Park. This brand-new home features modern finishes, an open layout, in-unit laundry, and a spacious private terrace with great views.Located just steps from the Metra station, restaurants, shopping, coffee shops, and everything downtown Highland Park has to offer, you'll enjoy the

  1770 1st St Unit 504, 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 $906,825

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

  378 Oakland Dr, Highland Park, IL 60035
• 

  

  

  /25

  Est $1,484,113

  Not Listed For Sale

  452 Lakeside Manor Rd, Highland Park, IL 60035

  • 5 Beds
  • 6 Baths
  • 4,328 Sq Ft
  • Built 1968

  452 Lakeside Manor Rd, Highland Park, IL 60035

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sonia Cohen Coldwell Banker Realty
• 

  

  

  /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
• 

  

  /9

  $1,700 Per Month

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

  1660 2nd St Unit 6, Highland Park, IL 60035

  *Available Now!* Newly renovated spacious 1 Bedroom, 1 Bathroom apartment, located just steps from Downtown Highland Park. This unit features brand new quartz countertops, designer cabinets and new stainless appliances.1 assigned parking space, outdoor patio area, nestled in a small building off Second Street. Water, Trash and Sewer included in utility fee, so you only pay electric! Coin laundry

  Gregg Handrich Archpoint Property LLC

  1660 2nd St Unit 6, 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 $1,964,708

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

  796 Marion Ave, Highland Park, IL 60035
• 

  

  /41

  Est $2,094,369

  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
• 

  

  /40

  $589,900

  Open Sun 1:30PM - 3:30PM

  • 3 Beds
  • 2 Baths
  • 1,591 Sq Ft

  1269 Eastwood Ave, Highland Park, IL 60035

  Beautifully updated Sherwood Forest 3 bedroom, 2 full bathroom home with a fully fenced back yard. Spacious rooms, great layout and updates throughout. New sanded and stained hardwood floors, freshly painted interior and exterior, energy efficient windows, completely remodeled kitchen with all new stainless steel appliances with induction cooktop, white shaker cabinets and quartz countertops.

  Ljubica Delic @properties Christie's International Real Estate

  1269 Eastwood Ave, Highland Park, IL 60035
• 

  

  /11

  $1,900 Per Month

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

  1660 2nd St Unit 1, Highland Park, IL 60035

  *Available 8/1* Enjoy downtown Highland Park with all that the Northshore has to offer! 1 Block from Metra, shopping, restaurants, grocery and more from this home. This large 1 bed, 1 bath apartment is renovated to capture the charm of this vintage home, while offering all the modern conveniences and location you could want! Gorgeous refinished hardwood floors, non-working fireplace, tall

  Gregg Handrich Archpoint Property LLC

  1660 2nd St Unit 1, 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
• 

  

  /32

  Est $677,022

  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
• 

  

  /29

  $525,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  Unlisted Address

  Warm and inviting cape cod home with excellent natural light on a large lot. Flexible space that can adjust with your needs. It starts with a large and open living room that adjoins the foyer as does the dining room which has a beautiful view of the treelined street. The kitchen is open to the family room addition that features a vaulted ceiling and windows that look out onto the fenced backyard.

  Ron Ehlers Compass

  Unlisted Address
• 

  

  /34

  $11,000 Per Month

  • 4 Beds
  • 5 Baths
  • House for Rent

  735 Baldwin Rd, Highland Park, IL 60035

  Move right into this 4 bed / 3 full and 2 half bath farmhouse-meets-luxury short term rental home in prime East Highland Park location. Available fully furnished as soon as 8/17/26. Gorgeous chef's kitchen opens to dining room room with high ceilings, dramatic fireplace and stunning exposed beams. Remodeled family room with french doors overlook the private yard. Master suite features luxurious

  Jacqueline Lotzof Compass

  735 Baldwin Rd, Highland Park, IL 60035
• 

  

  /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 $1,190,629

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

  520 Sheridan Rd, Highland Park, IL 60035
• 

  

  /36

  Est $902,769

  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
• 

  

  /23

  $599,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,837 Sq Ft

  937 Pleasant Ave, Highland Park, IL 60035

  located on a quiet cul-de-sac in sought-after Ravinia. This home offers a flexible layout with a large first-floor bedroom and full bathroom, plus two additional bedrooms and a half bath on the second level. Partially finished basement includes a family room, full bathroom, laundry area, and additional storage space. Major updates completed in 2022 include a fully gutted and renovated kitchen,

  Daniel Daoud Realtyline Co.

  937 Pleasant Ave, Highland Park, IL 60035
• 

  

  /16

  $5,800 Per Month

  • 5 Beds
  • 4.5 Baths
  • 2,489 Sq Ft
  • House for Rent

  2078 Linden Ave, Highland Park, IL 60035

  Fabulous 4 bed 3.2 bath beautiful colonial in superb East Highland Park location. Gracious living room with wood burning fireplace. Separate formal dining room with leaded glass windows. Wonderful sunny kitchen with 42" wood cabinets and granite countertops. Three bedrooms on the 2nd floor including the primary bedroom suite with walk-in closet. Third floor suite and full bath, office or play

  Linda Levin Jameson Sotheby's Intl Realty

  2078 Linden Ave, 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 $609,329

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

  1177 Ridge Rd, Highland Park, IL 60035
• 

  

  /29

  Est $1,039,876

  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
• 

  

  /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
• 

  

  /11

  $3,430 Per Month

  • 2 Beds
  • 2 Baths
  • 1,142 Sq Ft
  • Apartment for Rent

  555 Roger Williams Ave Unit 405, Highland Park, IL 60035

  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 units have

  Larry Klairmont Twins Realty LLC

  555 Roger Williams Ave Unit 405, 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 $1,444,310

  Last Listing Agent Brandy Simon Engel & Voelkers Chicago North Shore

  1375 Sheridan Rd, Highland Park, IL 60035
• 

  

  /23

  Est $631,563

  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
• 

  

  /7

  $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
• 

  

  /24

  $467,000

  Sold Aug 22, 2025

  1660 1st St Unit 303, Highland Park, IL 60035

  • 2 Beds
  • 2 Baths
  • 1,810 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $258/SF
  • 12 Days On Market

  Current Estimated Value $514,596

  Last Listing Agent Annette Blumberg Baird & Warner

  1660 1st St Unit 303, Highland Park, IL 60035
• 

  

  /14

  Est $848,011

  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
• 

  

  /6

  $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 $490,114

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

  927 Half Day Rd, Highland Park, IL 60035
• 

  

  /29

  Est $1,327,977

  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
• 

  

  /42

  $650,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft

  2660 Saint Johns Ave, Highland Park, IL 60035

  You'll fall in love the moment you step into the foyer of 2660 Saint Johns Ave. Hardwood floors extend throughout most of the home, the comfortable living room has a huge picture window overlooking the front yard and a charming archway leads into a formal dining room...perfect for entertaining family and friends. The kitchen was updated in 2022 with new backsplash, Quartz countertops, tile

  Steve Grunyk @properties Christie's International Real Estate

  2660 Saint Johns Ave, 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 $3,864,344

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

  1250 Linden Ave, Highland Park, IL 60035
• 

  

  /41

  Est $1,289,554

  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
• 

  

  /61

  $1,200,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,669 Sq Ft

  87 Ravinoaks Ln, Highland Park, IL 60035

  ** Multiple offers received. Seller requests 'Highest & Best' offers by 5pm, Tuesday, May 5th ** Wait til you see the beautiful updates the current owners have made to this fantastic MCM home just a few doors from Lake Michigan with ravine and seasonal lake views! Designed by J. Marion Gutnayer, this lovely 2-story brick, stone & glass mid-century modern home is filled with natural light thanks

  Lou Zucaro Baird & Warner

  87 Ravinoaks Ln, 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 $739,524

  Last Listing Agent Shlomo Arel Kale Realty

  860 Green Bay Rd, Highland Park, IL 60035
• 

  

  /32

  Est $1,469,325

  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
• 

  

  /8

  $449,000

  $50K PRICE DROP Pending

  • 4 Beds
  • 2 Baths

  636 Homewood Ave, Highland Park, IL 60035

  2 Flat. Each unit is 2 bedrooms, 1 bath. Long time tenants. Basement. Large parking lot. Near town, train, park, hospital and more. Sold "As Is".

  Andrew Shevelev American Real Estate Services

  636 Homewood Ave, 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 $702,564

  Last Listing Agent Mada Hitchmough Compass

  719 Burchell Ave, Highland Park, IL 60035
• 

  

  /35

  Est $772,720

  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
• 

  

  /21

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,262 Sq Ft

  713 Orleans Dr, Highland Park, IL 60035

  Move right into this extremely well maintained Chantily home. Located in the center of the sought after Chantily complex. Large eat-in-kitchen flows right into family room. Large combo living room and dining room are perfect for entertaining. Primary suite includes tons of closet space including a cedar closet and new carpeting. Two additional generous size bedrooms and hall bath. Upstairs

  Ted Pickus @properties Christie's International Real Estate

  713 Orleans Dr, Highland Park, IL 60035

Showing Results 121 - 160, Page 4 of 18