12,678

Highland Park, IL Homes

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  • /39

    $949,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,704 Sq Ft

    365 Green Bay Rd, Highland Park, IL 60035

    Very cool & Spacious Ravinia Custom 2nd owner Mid Century Home! Great floor plan with very thoughtful and interesting natural lighting throughout. The first floor features stunning 3 story staircase flanked by an inviting living room with wood burning fireplace, convenient office, and open family room, kitchen and dining room overlooking the fenced in, beautiful backyard with blue stone patio. A

    Cory Albiani @properties Christie's International Real Estate

    365 Green Bay Rd, Highland Park, IL 60035
  • /85

    $1,750 - $2,995

    Total Monthly Price

    • Studio - 2 Beds
    • 1 Bath
    • 400 Sq Ft
    • Condo for Rent

    730 Judson Ave, Highland Park, IL 60035

    Wonderful Vintage Building in the Heart of Ravinia – Highland ParkThis building is within walking distance of local schools and parks. Jens Jensen Park, where Highland Park’s weekly food truck fest is held, is right across the street! Living here, you’ll be just steps away from the Ravinia Metra stop and restaurants galore!Amenities:- Hardwood Floors- Updated Large

    730 Judson Ave, Highland Park, IL 60035
  • /26

    $750,000

    Sold Jun 10, 2026

    2725 Roslyn Ln, Highland Park, IL 60035

    • 4 Beds
    • 3 Baths
    • 1,698 Sq Ft
    • Built 1955

    Last Sold Summary

    • 8% Above List Price
    • $442/SF
    • 0 Days On Market

    Current Estimated Value $727,357

    Last Listing Agent Diana Marcus @properties Christie's International Real Estate

    2725 Roslyn Ln, Highland Park, IL 60035
    • /53

      Est $1,080,507

      Not Listed For Sale

      227 Ivy Ln, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 2,500 Sq Ft
      • Built 1940
      227 Ivy Ln, Highland Park, IL 60035

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Sally O'Donnell @properties Christie's International Real Estate

  • /25

    $625,000

    Pending
    • 2 Beds
    • 2 Baths
    • 2,193 Sq Ft

    1871 Elmwood Dr, Highland Park, IL 60035

    Welcome to 1871 Elmwood Dr! This charming solid brick and stone Ranch is set on a beautifully landscaped corner lot in the heart of coveted Sunset Park. This 2 Bedroom, 2 Bath, updated and meticulously maintained home offers both comfort and style. The lovely Living Room features crown moldings, a woodburning fireplace, custom built ins and an expansive bay window outfitted with plantation

    Ellen Chukerman Compass

    1871 Elmwood Dr, Highland Park, IL 60035
  • /26

    $4,850 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    867 Auburn Ct, Highland Park, IL 60035

    Sunny property location on a cozy landscaped lot. End of quiet cul-de-sac street. Freshly decorated with newer kitchen and appliances. Beautifully finished hardwood floors throughout . This split-level ranch has four full bedrooms including a master bedroom with en suite bathroom. Walkout lower level/den has gorgeous new flooring. Full size backyard deck, perfect for entertaining. Two-car garage

    Erol Gladan Erol Gladan

    867 Auburn Ct, Highland Park, IL 60035
  • /18

    $170,000

    Sold Oct 14, 2025

    891 Central Ave Unit 331, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,089 Sq Ft
    • Built 2002

    Last Sold Summary

    • $156/SF
    • 30 Days On Market

    Current Estimated Value $195,746

    Last Listing Agent Carolyn Cerf @properties Christie's International Real Estate

    891 Central Ave Unit 331, Highland Park, IL 60035
    • /33

      Est $1,456,867

      Not Listed For Sale

      265 Ivy Ln, Highland Park, IL 60035

      • 4 Beds
      • 4.5 Baths
      • 3,300 Sq Ft
      • Built 1949
      265 Ivy Ln, Highland Park, IL 60035

      Last Sold Summary

      • 4 Days On Market

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

  • /26

    $850,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 3,224 Sq Ft

    839 Edgewood Ct, Highland Park, IL 60035

    Perfectly nestled on a serene wooded cul de sac in West Highland Park, this well maintained residence sits on a .30 acre property with a spacious backyard. The property offers over 3300 sq ft of flexible living space featuring 4 bedrooms and 3.5 baths upstairs, plus one additional bedroom/den and full bath in the fully finished basement. Main floor highlights include a den with fireplace and wet

    Janet Weinberg @properties Christie's International Real Estate

    839 Edgewood Ct, Highland Park, IL 60035
  • /19

    $2,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    696 Elm Place Unit 204, Highland Park, IL 60035

    Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your next home in the desirable Highland Park community! This property offers a comfortable and convenient living experience perfect for anyone looking to settle in this vibrant area.Key property features include spacious bedrooms

    696 Elm Place Unit 204, Highland Park, IL 60035
  • /23

    $960,000

    Sold May 04, 2026

    371 Red Oak Ln, Highland Park, IL 60035

    • 4 Beds
    • 2.5 Baths
    • 2,890 Sq Ft
    • Built 1976

    Last Sold Summary

    • 10% Above List Price
    • $332/SF
    • 3 Days On Market

    Current Estimated Value $940,202

    Last Listing Agent Marcia Shanin Engel & Voelkers Chicago North Shore

    371 Red Oak Ln, Highland Park, IL 60035
    • /30

      Est $1,485,929

      Not Listed For Sale

      149 Oak Knoll Terrace, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 4,362 Sq Ft
      • Built 1946
      149 Oak Knoll Terrace, Highland Park, IL 60035

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Deb Baker Compass

  • /25

    $2,550,000

    • 4 Beds
    • 5.5 Baths
    • 5,590 Sq Ft

    1551 Mill Trail, Highland Park, IL 60035

    IMPRESSIVE PRICE IMPROVEMENT!!!The epitome of luxurious one-level living. Set on a magnificent 3+ acre parcel in an exclusive private enclave, this extraordinary property is surrounded on three sides by the Heller Nature Preserve, offering 97 acres of protected land, serene privacy, and breathtaking natural beauty. Enjoy miles of scenic trails ideal for hiking, cross-country skiing, and horseback

    Honore Frumentino @properties Christie's International Real Estate

    1551 Mill Trail, Highland Park, IL 60035
  • /13

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 1,150 Sq Ft
    • Apartment for Rent

    1660 2nd St Unit 4, Highland Park, IL 60035

    *Available Now* - Not to be missed, this massive 1 bed + den, 1 bath apartment in the heart of Highland Park has been completely renovated. It has two floors and is over 1100 SF, the second floor has a den/2nd living area that is perfectly set up for work from home. New vinyl plank throughout the unit. Brand new kitchen with stainless steel appliances, walk in pantry directly adjacent to kitchen,

    Gregg Handrich Archpoint Property LLC

    1660 2nd St Unit 4, Highland Park, IL 60035
  • /31

    $555,000

    Sold Jun 24, 2026

    3175 University Ave, Highland Park, IL 60035

    • 3 Beds
    • 2 Baths
    • 2,574 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Below List Price
    • $216/SF
    • 8 Days On Market

    Current Estimated Value $561,171

    Last Listing Agent Keri Meacham Berkshire Hathaway HomeServices Chicago

    3175 University Ave, Highland Park, IL 60035
    • /32

      Est $990,723

      Not Listed For Sale

      149 Deere Park Ct, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 2,366 Sq Ft
      • Built 1954
      149 Deere Park Ct, Highland Park, IL 60035

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Suzanne Rothenberg Baird & Warner

  • /64

    $1,495,000

    $80K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,819 Sq Ft

    3464 Old Mill Rd, Highland Park, IL 60035

    Expanded and renovated in 2008, this two-story prairie-style executive home offers over 9,000 square feet of finished living area across three levels, all easily accessible by a centrally located elevator or stairs, and is situated on over an acre of wooded property along a quiet, private road in Highland Park. The home offers exceptional flexibility with spaces ideal for a variety of lifestyles,

    Kelly Ipjian Exit Strategy Realty

    3464 Old Mill Rd, Highland Park, IL 60035
  • /15

    $2,095 Per Month

    • 1 Bed
    • 1 Bath
    • 597 Sq Ft
    • Condo for Rent

    696 Elm Place Unit 300, Highland Park, IL 60035

    Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your new home in the heart of Highland Park, IL! This inviting rental opportunity offers a perfect blend of comfort and convenience, making it ideal for those seeking a vibrant community feel.This lovely property features a

    696 Elm Place Unit 300, Highland Park, IL 60035
  • /26

    $1,150,000

    Sold Apr 24, 2026

    625 Sheridan Rd, Highland Park, IL 60035

    • 3 Beds
    • 2.5 Baths
    • 4,197 Sq Ft
    • Built 1979

    Last Sold Summary

    • 6% Below List Price
    • $274/SF
    • 22 Days On Market

    Current Estimated Value $1,201,378

    Last Listing Agent Debbie Scully @properties Christie's International Real Estate

    625 Sheridan Rd, Highland Park, IL 60035
    • /44

      Est $1,925,157

      Not Listed For Sale

      15 S Deere Park Dr, Highland Park, IL 60035

      • 3 Beds
      • 5.5 Baths
      • 4,721 Sq Ft
      • Built 1946
      15 S Deere Park Dr, Highland Park, IL 60035

      Last Sold Summary

      • 241 Days On Market

      Last Listing Agent Margie Brooks Baird & Warner

  • /26

    $775,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,451 Sq Ft

    Unlisted Address

    Begin to make your memories in this spacious, freshly cleaned and painted two story home in desirable Sherwood Manor. Hardwood floors in most rooms, just waiting for your stunning area rugs as furniture scene setters. The updated, stainless and granite kitchen has built in table space framed by two pantry closets and bay window view of lush rear yard. Nearby family room has fireplace and sliding

    Debbie Hymen Compass

    Unlisted Address
  • /5

    $1,750 Per Month

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

    1155 Saint Johns Ave Unit G, Highland Park, IL 60035

    Enjoy the perfect blend of historic charm and modern convenience in this beautifully renovated One-bedroom unit located in the heart of the Ravinia district. Situated on the Second floor of a converted old building, this cozy space features a hardwood floor and freshly painted walls. The rent includes heat and water, providing a comfortable living experience. Enjoy the nice view from your window.

    Afram Slephosh SENW

    1155 Saint Johns Ave Unit G, Highland Park, IL 60035
  • /23

    $1,645,000

    Sold Dec 12, 2025

    8 Heritage Dr, Highland Park, IL 60035

    • 4 Beds
    • 3.5 Baths
    • 2,825 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $582/SF
    • 63 Days On Market

    Current Estimated Value $1,699,711

    Last Listing Agent Michael Hagenson New Era Chicago, LLC

    8 Heritage Dr, Highland Park, IL 60035
    • /32

      Est $1,369,849

      Not Listed For Sale

      294 N Deere Park Dr W, Highland Park, IL 60035

      • 4 Beds
      • 4.5 Baths
      • 3,410 Sq Ft
      • Built 1928
      294 N Deere Park Dr W, Highland Park, IL 60035

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Liz Watson @properties Christie's International Real Estate

  • /26

    $699,000

    $51K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 2,428 Sq Ft

    974 Princeton Ave, Highland Park, IL 60035

    This charming center entry Colonial located on .30 acres in the coveted Sunset Park neighborhood, offers 4 bedrooms, 2 full baths and 1 half bath. The home features timeless vintage details including crown moldings and hardwood floors throughout the first and second floors. The first floor welcomes you into a charming vestibule/foyer that leads to a large sun-filled living room with fireplace and

    Beth Wexler @properties Christie's International Real Estate

    974 Princeton Ave, Highland Park, IL 60035
  • /19

    $1,750 Per Month

    • Studio
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    730 Judson Ave Unit 9, Highland Park, IL 60035

    Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your new home in the heart of Braeside, Highland Park! This charming property offers a comfortable living environment with easy access to everyday conveniences. Surrounded by great restaurants and department stores, you’ll enjoy both

    730 Judson Ave Unit 9, Highland Park, IL 60035
  • /23

    $550,000

    Sold Dec 22, 2025

    940 Augusta Way Unit 304, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,926 Sq Ft
    • Built 2001

    Last Sold Summary

    • $286/SF
    • 9 Days On Market

    Current Estimated Value $586,017

    Last Listing Agent Dan Timm Baird & Warner

    940 Augusta Way Unit 304, Highland Park, IL 60035
    • /22

      Est $1,596,453

      Not Listed For Sale

      332 N Deere Park Dr W, Highland Park, IL 60035

      • 6 Beds
      • 5.5 Baths
      • 5,554 Sq Ft
      • Built 1925
      332 N Deere Park Dr W, Highland Park, IL 60035

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Sarah Mindes Kale Realty

  • /31

    $795,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,904 Sq Ft

    460 Hazel Ave, Highland Park, IL 60035

    Mid-Century Modern Gem Set in One of Highland Park's Most Premier Locations and Tucked Away with Ultimate Privacy on a Lush, Beautifully Manicured Lot. Enter into the Dramatic Double Staircase with Marble Foyer, Spacious Living / Dining Room - Perfect for Entertaining! Beautiful Hardwood Floors and an Updated Eat-In Kitchen with Newer Stainless Steel Appliances, White Cabinets and Granite

    Janet Borden Compass

    460 Hazel Ave, Highland Park, IL 60035
  • /11

    $1,650 Per Month

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

    1155 Saint Johns Ave Unit F, Highland Park, IL 60035

    Enjoy the perfect blend of historic charm and modern convenience in this beautifully renovated One-bedroom unit located in the heart of the Ravinia district. Situated on the Second floor of a converted old building, this cozy space features hardwood floors, freshly painted walls. The rent includes heat and water, providing a comfortable living experience. Enjoy the nice view from your window.

    Afram Slephosh SENW

    1155 Saint Johns Ave Unit F, 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 $808,652

    Last Listing Agent Deb Baker Compass

    945 Villas Ct, Highland Park, IL 60035
    • /49

      Est $1,577,549

      Not Listed For Sale

      333 Lakeside Place, Highland Park, IL 60035

      • 6 Beds
      • 4.5 Baths
      • 4,516 Sq Ft
      • Built 1930
      333 Lakeside Place, Highland Park, IL 60035

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Tim Stassi Dwell One Realty

  • /36

    $1,095,000

    • 6 Beds
    • 5.5 Baths
    • 3,396 Sq Ft

    2925 Parkside Dr, Highland Park, IL 60035

    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

    Beth Wexler @properties Christie's International Real Estate

    2925 Parkside Dr, Highland Park, IL 60035
  • /13

    $1,750 Per Month

    • Studio
    • 1 Bath
    • 351 Sq Ft
    • Condo for Rent

    696 Elm Place Unit 105, Highland Park, IL 60035

    Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your next home in the charming district of Highland Park, IL! This well-situated property offers the perfect blend of comfort and convenience, making it an ideal choice for anyone looking to enjoy a vibrant lifestyle.This property

    696 Elm Place Unit 105, 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 $640,125

    Last Listing Agent James Carey Forest Bluff Realty

    1320 Ferndale Ave, Highland Park, IL 60035
    • /28

      Est $1,388,924

      Not Listed For Sale

      144 Sheridan Rd, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 4,258 Sq Ft
      • Built 1941
      144 Sheridan Rd, Highland Park, IL 60035

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Luminita Ispas Century 21 S.G.R., Inc.

  • /42

    $873,500

    Open Sun 12PM - 2PM
    • 4 Beds
    • 2 Baths
    • 2,622 Sq Ft

    1538 Oakwood Ave, Highland Park, IL 60035

    A welcoming front porch sets the tone for the warmth and charm you'll find 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 and a two-car, recently structurally redone detached garage. The interior features hardwood floors, solid oak doors, 9' ceilings, and

    Mirella Caputo @properties Christie's International Real Estate

    1538 Oakwood Ave, Highland Park, IL 60035
  • /14

    $2,350 Per Month

    • 2 Beds
    • 1.5 Baths
    • Apartment for Rent

    1988 Green Bay Rd Unit 4, Highland Park, IL 60035

    Fantastic rental in Downtown Highland Park! Walk to everything - restaurants, shopping, Metra, and more. Completely updated throughout with abundant natural light in every room and beautiful exposed brick details that add warmth and character. Enjoy entertaining or relaxing on the private balcony, perfect for summer evenings. Attached 2-car garage plus a private in-unit laundry room conveniently

    Benjamin Lissner Baird & Warner

    1988 Green Bay Rd Unit 4, Highland Park, IL 60035
  • /16

    $280,000

    Sold Aug 12, 2025

    2020 St Johns Ave Unit 309, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,269 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Above List Price
    • $221/SF
    • 2 Days On Market

    Current Estimated Value $315,291

    Last Listing Agent Debbie Croft @properties Christie's International Real Estate

    2020 St Johns Ave Unit 309, Highland Park, IL 60035
    • /2

      Est $818,358

      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

Showing Results 81 - 120, Page 3 of 18

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