Highland Park, IL Homes

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  /28

  $495,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  1039 Deerfield Place Unit 1039, Highland Park, IL 60035

  Beautiful, recently renovated 3 bedroom and 2 full bathroom condo offering 1850 square feet of living space on one level (2nd/top floor) located in desirable Deerfield Place in Highland Park. Stunning kitchen with solid wood cabinetry blended with quartz countertops and stainless steel appliances. Huge living room with 15 foot cathedral like ceilings with sliding doors to your very large rear

  Sohail Salahuddin eXp Realty

  1039 Deerfield Place Unit 1039, Highland Park, IL 60035
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  /13

  $2,012 Per Month

  • 2 Beds
  • 1 Bath
  • 872 Sq Ft
  • Apartment for Rent

  1506 Glencoe Ave Unit 2N, Highland Park, IL 60035

  Beautifully remodeled apartment available within walking distance to downtown Highland Park! Recent upgrades to this spacious apartment include new windows, new hardwood flooring, brand new bathroom (fixtures, bathtub, toilet, vanity), brand new kitchen (new appliances, counters, cabinets, etc). This brick building has spacious bedrooms that can fit a king-size bed and ample closet space. Located

  Brent Horvay The Horvay Group LLC

  1506 Glencoe Ave Unit 2N, Highland Park, IL 60035
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  /51

  $438,500 Sold Jan 15, 2026

  2013 Castlewood Rd, Highland Park, IL 60035

  • 2 Beds
  • 1 Bath
  • 1,138 Sq Ft
  • Built 1954

  Last Sold Summary

  • 8% Below List Price
  • $385/SF
  • 31 Days On Market

  Current Estimated Value $436,173

  Last Listing Agent Quin O'Brien 4 Sale Realty Advantage LLC

  2013 Castlewood Rd, Highland Park, IL 60035
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  /32

  Est $1,353,127 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

  • 4% Above List Price
  • $381/SF
  • 3 Days On Market

  • Last Sold Price $1,300,000
  • Jul 22, 2024

  Last Listing Agent Liz Watson @ Properties
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  /27

  $1,249,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 4,323 Sq Ft

  Unlisted Address

  Recently remodeled ranch home ideally located in sought-after East Highland Park. This beautifully updated 3-bedroom, 2.5-bath residence offers an open, airy layout highlighted by vaulted ceilings and a spacious great room. A sun-filled four-season room provides tranquil views of the private, fully fenced backyard, surrounded by lush, mature landscaping. The stunning new kitchen is equipped with

  Margie Brooks Baird & Warner

  Unlisted Address
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  /72

  $1,850 - $1,995

  Total Monthly Price

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

  725 Saint Johns Ave, Highland Park, IL 60035

  Beautiful, updated Vintage building in the heart of Highland Park's Ravinia districtAmenities:- Hardwood Floors- Large Updated Kitchen- Separate Dining Area- Updated Bathroom- Miniblinds- Ceiling Fans- Plenty of Closet Space- Laundry in-unit- Pet-Friendly Building

  725 Saint Johns Ave, Highland Park, IL 60035
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  /19

  $690,000 Sold Jun 02, 2025

  2979 Lexington Ln, Highland Park, IL 60035

  • 4 Beds
  • 3.5 Baths
  • 2,976 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $232/SF
  • 30 Days On Market

  Current Estimated Value $718,913

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

  2979 Lexington Ln, Highland Park, IL 60035
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  /22

  Est $1,558,702 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

  • 4% Above List Price
  • $270/SF
  • 45 Days On Market

  • Last Sold Price $1,500,000
  • Apr 21, 2025

  Last Listing Agent Sarah Mindes Kale Realty
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  /24

  $1,240,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,272 Sq Ft

  285 Linden Park Place, Highland Park, IL 60035

  Walk to town, the train, schools, and the lake from this remodeled Tudor on a quiet cul-de-sac in East Highland Park. The main level includes a formal living room, separate dining room, and a family room with fireplace, plus a private office. The kitchen is equipped with high-end appliances, an island, and a dedicated eating area. A bright four-season room with heated floors completes the first

  Margie Brooks Baird & Warner

  285 Linden Park Place, Highland Park, IL 60035
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  /12

  $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
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  $750,000 Sold Feb 20, 2026

  3349 University Ave, Highland Park, IL 60035

  • 4 Beds
  • 2.5 Baths
  • 3,562 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Above List Price
  • $211/SF
  • 2 Days On Market

  Current Estimated Value $740,379

  Last Listing Agent Alan Meyerowitz @properties Christie's International Real Estate

  3349 University Ave, Highland Park, IL 60035
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  /49

  Est $1,437,830 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

  • 1% Above List Price
  • $316/SF
  • 88 Days On Market

  • Last Sold Price $1,425,000
  • Jun 24, 2024

  Last Listing Agent Tim Stassi Dwell One Realty
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  /40

  $839,900

  • 6 Beds
  • 3 Baths
  • 2,834 Sq Ft

  830 Deerfield Rd, Highland Park, IL 60035

  Assya Zinger Vareljan Berkshire Hathaway HomeServices Chicago

  830 Deerfield Rd, Highland Park, IL 60035
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  $1,850 - $1,995

  Total Monthly Price

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

  725 Saint Johns Ave, Highland Park, IL 60035

  Beautiful, updated Vintage building in the heart of Highland Park's Ravinia districtAmenities:- Hardwood Floors- Large Updated Kitchen- Separate Dining Area- Updated Bathroom- Miniblinds- Ceiling Fans- Plenty of Closet Space- Laundry in-unit- Pet-Friendly Building

  725 Saint Johns Ave, Highland Park, IL 60035
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  /41

  $810,000 Sold Mar 13, 2026

  835 Yale Ln, Highland Park, IL 60035

  • 5 Beds
  • 3.5 Baths
  • 2,462 Sq Ft
  • Built 1929

  Last Sold Summary

  • 5% Below List Price
  • $329/SF
  • 29 Days On Market

  Current Estimated Value $841,423

  Last Listing Agent Janet Borden Compass

  835 Yale Ln, Highland Park, IL 60035
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  /28

  Est $1,355,594 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

  • 4% Above List Price
  • $305/SF
  • 37 Days On Market

  • Last Sold Price $1,300,000
  • Feb 19, 2025

  Last Listing Agent Luminita Ispas Century 21 S.G.R., Inc.
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  /69

  $3,999,000

  • 6 Beds
  • 11 Baths
  • 10,000 Sq Ft

  2214 Churchill Ln, Highland Park, IL 60035

  Elegant and sophisticated custom built 6 bedroom, 7 full and 4 half bath home located on 1 acre that is reminiscent of a luxury hotel complete with patio, pool and spa. This limestone clad home boasts unsurpassed quality construction and is accompanied with high-end interior designer appointed finishes throughout. Some of the home's highlights include: hand scraped, hand beveled hardwood floors,

  Beth Wexler @properties Christie's International Real Estate

  2214 Churchill Ln, Highland Park, IL 60035
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  /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
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  /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 $173,966

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

  891 Central Ave Unit 331, Highland Park, IL 60035
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  /2

  Est $741,066 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

  • 12% Above List Price
  • $298/SF
  • 16 Days On Market

  • Last Sold Price $660,000
  • May 02, 2024

  Last Listing Agent Jane Lee RE/MAX
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  /26

  $799,900

  • 5 Beds
  • 3 Baths
  • 2,878 Sq Ft

  1459 Eastwood Ave, Highland Park, IL 60035

  Best value in Sherwood Forest, Highland Park. Fully renovated 5 bedroom, 3 bathroom home with 2 primary suites, finished basement, and fenced yard. This move-in ready home features an open layout with natural light, a large living room with fireplace, and an updated kitchen with quartz countertops, LG appliances, and custom cabinets. Dining area with sliding doors leads to a private backyard.

  Jessica Xu Concentric Realty, Inc

  1459 Eastwood Ave, Highland Park, IL 60035
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  /5

  $1,995

  Total Monthly Price

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

  729 Saint Johns Ave Unit . 12, Highland Park, IL 60035

  Welcome to this beautifully updated condo, perfectly situated in the heart of Highland Park. Located just across from the Ravinia Metra station, this home offers unparalleled convenience with top-rated schools, parks, and all the amenities you need right at your doorstep. Sunset Woods Park, only half a block away, features expansive green spaces, playgrounds, and local shops. Plus, enjoy a wide

  729 Saint Johns Ave Unit . 12, Highland Park, IL 60035
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  /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 $863,936

  Last Listing Agent Marcia Shanin Engel & Voelkers Chicago North Shore

  371 Red Oak Ln, Highland Park, IL 60035
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  /25

  Est $1,419,491 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

  • 9% Above List Price
  • $300/SF
  • 0 Days On Market

  • Last Sold Price $1,300,000
  • Sep 06, 2023

  Last Listing Agent Sonia Cohen Coldwell Banker Realty
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  /31

  $559,900

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

  3175 University Ave, Highland Park, IL 60035

  This meticulously maintained 3-bedroom, 2-bath mid-century Highlands ranch blends timeless charm with thoughtful updates throughout. Set on a deep 72X189 lot with mature trees and a spacious patio, the outdoor space is ideal for both relaxing and entertaining. Inside, the sun-filled living room features oversized windows and beautiful hardwood floors that carry throughout the home. The spacious

  Keri Meacham RE/MAX In The Village

  3175 University Ave, Highland Park, IL 60035
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  /12

  $3,380 Per Month

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

  555 Roger Williams Ave Unit 303, 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 303, Highland Park, IL 60035
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  /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 $1,242,760

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

  625 Sheridan Rd, Highland Park, IL 60035
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  /41

  Est $1,970,062 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

  • 4% Above List Price
  • $380/SF
  • 112 Days On Market

  • Last Sold Price $1,900,000
  • Mar 06, 2025

  Last Listing Agent Ted Pickus @ Properties
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  /20

  $690,000 Pending

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

  719 Burchell Ave, Highland Park, IL 60035

  Welcome home to this light-filled custom ranch tucked away in a private setting. A welcoming foyer opens to a spacious living room with a cozy wood-burning fireplace. The kitchen features white cabinetry, stainless steel appliances, and a custom island/table that overlooks the living room - perfect for everyday living and entertaining. The dining area flows seamlessly from the kitchen, creating

  Mada Hitchmough Compass

  719 Burchell Ave, Highland Park, IL 60035
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  /20

  $2,250

  Total Monthly Price

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

  730 Judson Ave Unit A0, Highland Park, IL 60035

  730 Judson unit 04Judson + Roger WilliamsHighland Park$2250 per MonthAvailable: 03/25/2026Terrific one bedroom in the heart of downtown Highland Park features brand new kitchen with espresso cabinets, stainless steel appliances, dishwasher, spacious living area with ceiling fan, great closet space, brand new bathroom, hardwood floors throughout, laundry in unit, and pets

  730 Judson Ave Unit A0, Highland Park, IL 60035
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  /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 $1,640,725

  Last Listing Agent Michael Hagenson New Era Chicago, LLC

  8 Heritage Dr, Highland Park, IL 60035
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  /36

  Est $852,113 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

  • 3% Above List Price
  • $300/SF
  • 2 Days On Market

  • Last Sold Price $825,000
  • Mar 26, 2025

  Last Listing Agent Nancy Karp @ Properties
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  $695,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,546 Sq Ft

  778 Barberry Rd, Highland Park, IL 60035

  Step into this beautifully updated split-level home with a finished sub-basement that truly has it all! From the moment you walk through the door, you're greeted by soaring vaulted ceilings and an open, light-filled layout that effortlessly connects the kitchen, living, and dining spaces-perfect for both everyday living and entertaining. The main level shines with stunning medium brown and gray

  Cynthia Windeler Keller Williams Premiere Properties

  778 Barberry Rd, Highland Park, IL 60035
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  /15

  $3,495 Per Month

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Condo for Rent

  1250 Park Ave W Unit 435, Highland Park, IL 60035

  This 3 bedroom/2 bathroom rental has been completely renovated and is ready for someone to move right in! Gorgeous neutral finishes, including all new LVT flooring. Recessed lighting throughout the unit. Great layout with kitchen open to dining room and living room. Beautiful fireplace in living room and sliders to balcony. Treetop and pond views from all rooms. In-unit laundry room w/brand new,

  Erin Smith @properties Christie's International Real Estate

  1250 Park Ave W Unit 435, Highland Park, IL 60035
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  /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 $553,530

  Last Listing Agent Dan Timm Baird & Warner

  940 Augusta Way Unit 304, Highland Park, IL 60035
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  /29

  Est $1,052,507 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

  • $417/SF
  • 3 Days On Market

  • Last Sold Price $1,050,000
  • Apr 28, 2025

  Last Listing Agent Lori Nieman @ Properties
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  /19

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,593 Sq Ft

  1000 Deerfield Rd Unit 101, Highland Park, IL 60035

  3 bedroom/ 2 bath (3rd bedroom currently used as a den) condo in a boutique, pet-friendly 12-unit elevator building, steps from Sunset Valley Golf Club. Amazing opportunity with 2 spaces in the heated garage plus a storage unit. The light-filled layout offers spacious rooms, a new balcony, and a primary suite with a private bath and an oversized walk-in closet. Minutes from the vibrant shopping

  Janet Borden Compass

  1000 Deerfield Rd Unit 101, Highland Park, IL 60035
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  /2

  $2,200

  Total Monthly Price

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  1978 Green Bay Rd, Highland Park, IL 60035

  Townhome for Rent in Highland Park — Available June 1Beautiful 2-bedroom, 1.5-bath townhome available for rent in desirable Highland Park, IL.Address: 1978 Green Bay Road, Highland Park, IL 60035Rent: $2,200/monthAvailable: June 1Garage: 1.5–2 car garage, depending on vehicle sizeThis townhome features in-unit laundry, a comfortable layout, and a large private

  1978 Green Bay Rd, Highland Park, IL 60035
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  /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 $798,856

  Last Listing Agent Deb Baker Compass

  945 Villas Ct, Highland Park, IL 60035
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  /23

  Est $601,031 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

  • 17% Above List Price
  • $334/SF
  • 12 Days On Market

  • Last Sold Price $515,000
  • Jul 11, 2024

  Last Listing Agent Bryce Fuller Baird Warner

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