Highwood, IL Homes

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  /11

  $749,900 New Construction

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

  535 Lockard Ln, Highwood, IL 60040

  Detached single family with over 2,400 square ft with a once in a lifetime layout. 45 foot backyard that lays out directly from the kitchen. 4 bedrooms or an office. Open layout. Pre-construction pricing. Pictures are architectural renderings of possibilities and potential options to be decided with builder. - $15,000 of free options if under contract by 2/15/2026

  Jorge Zea Jorge Zea Managing Broker

  535 Lockard Ln, Highwood, IL 60040
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  Explore Highwood

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  /35

  $1,750 - $3,549 per month

  Arrive North Shore

  1 - 3 Beds

  634 Sheridan Rd, Highwood, IL 60040

  Nestled between affluent Lake Forest and Highland Park, Arrive North Shore® is located in vibrant downtown Highwood and offers a unique opportunity to live on Chicago's scenic North Shore, just minutes away from Downtown Highwood shops and restaurants and Fort Sheridan Metra Stations. Our newly restyled apartment homes are equipped with deluxe kitchens, generous living spaces, and private patios.

  634 Sheridan Rd, Highwood, IL 60040
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  /2

  $355,000 Sold Jun 16, 2025

  328 Oak Terrace Ave, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,397 Sq Ft
  • Built 1956

  Last Sold Summary

  • 1% Above List Price
  • $254/SF
  • 1 Day On Market

  Current Estimated Value $371,663

  Last Listing Agent David Wilkerson eXp Realty

  328 Oak Terrace Ave, Highwood, IL 60040
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  /40

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,200 Sq Ft

  114 Michigan Ave, Highwood, IL 60040

  114 Michigan Ave, Highwood, IL 60040
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  /25

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft

  239 Sheridan Ave, Highwood, IL 60040

  Charming Home Steps from Downtown Highwood! Welcome to this inviting 3-bedroom, 1-bath home located just steps from vibrant downtown Highwood. Featuring a large kitchen with an attached dining room, this home offers the perfect blend of comfort and convenience. The partially finished basement provides additional living space or room to grow, while the 2-car garage adds valuable storage and

  Carol Santi Coldwell Banker Realty

  239 Sheridan Ave, Highwood, IL 60040
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  /16

  $3,133 per month

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 305, Highwood, IL 60040

  This three-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

  Christopher Dumitru Crosstown Realtors, Inc.

  440 Green Bay Rd Unit 305, Highwood, IL 60040
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  /16

  $700,000 Sold Nov 07, 2025

  738 Lyster Rd Unit 1, Highwood, IL 60040

  • 2 Beds
  • 2.5 Baths
  • 2,552 Sq Ft
  • Built 1885

  Last Sold Summary

  • 7% Below List Price
  • $274/SF
  • 48 Days On Market

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

  738 Lyster Rd Unit 1, Highwood, IL 60040
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  /33

  Est $618,525 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,002 Sq Ft

  338 Burchell Ave, Highwood, IL 60040

  338 Burchell Ave, Highwood, IL 60040
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  /3

  $175,000

  • Land
  • 0 Acre

  1 Burtis Ave, Highland Park, IL 60035

  Builder's Dream Opportunity! Seize this prime Highland Park lot - a 7,900 sq. ft. blank canvas ready for a stunning 3,085 sq. ft. home! Perfectly located near Highland Park and Highwood's vibrant festivals, top-rated restaurants, and thriving businesses, this property offers the best location. With utilities already in place from a previous home, you can hit the ground running on your next

  Melissa Newman @properties Christie's International Real Estate

  1 Burtis Ave, Highland Park, IL 60035
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  /12

  $2,921 per month

  • 2 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Apartment for Rent

  246 Green Bay Rd Unit 211, Highwood, IL 60040

  Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine

  Christopher Dumitru Crosstown Realtors, Inc.

  246 Green Bay Rd Unit 211, Highwood, IL 60040
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  /36

  $799,000 Sold Sep 19, 2025

  762 Deroo Loop Unit 5, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 3,173 Sq Ft
  • Built 1885

  Last Sold Summary

  • $252/SF
  • 18 Days On Market

  Current Estimated Value $791,632

  Last Listing Agent Michael Mitchell @properties Christie's International Real Estate

  762 Deroo Loop Unit 5, Highwood, IL 60040
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  /20

  Est $517,038 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,722 Sq Ft

  32 Michigan Ave, Highwood, IL 60040

  32 Michigan Ave, Highwood, IL 60040
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  /28

  $799,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  525 Lockard Ln, Highwood, IL 60040

  Proposed custom home well below market value for a limited time. First floor owners suites and ranch plans now available. Won't last long. Act now and receive up to an additional $15,000 of free upgrades.

  Jorge Zea Jorge Zea Managing Broker

  525 Lockard Ln, Highwood, IL 60040
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  /13

  $2,249 per month

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

  440 Green Bay Rd Unit 407, Highwood, IL 60040

  This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

  Christopher Dumitru Crosstown Realtors, Inc.

  440 Green Bay Rd Unit 407, Highwood, IL 60040
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  /2

  $890,000 Sold Oct 01, 2025

  795 Stables Ct W Unit 4, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 2,617 Sq Ft
  • Built 1895

  Last Sold Summary

  • 4% Below List Price
  • $340/SF
  • 11 Days On Market

  Current Estimated Value $897,941

  Last Listing Agent Karen Chien-Rooney Compass

  795 Stables Ct W Unit 4, Highwood, IL 60040
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  /26

  Est $447,914 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  102 High St, Highwood, IL 60040

  102 High St, Highwood, IL 60040
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  /25

  $665,000

  • 6 Beds
  • 4 Baths

  25 Webster Ave, Highwood, IL 60040

  Value add 4-unit residential investment property located in an ideal Highwood location, just one block off Sheridan Road and steps from downtown Highwood's restaurants, shops, and Metra access. The property was updated in 2022 with a combination of mechanical and cosmetic improvements, but there is a lot of upside in further rehab. The unit mix consists of one (1) studio, one (1) one-bedroom, and

  Alissa Morton Compass

  25 Webster Ave, Highwood, IL 60040
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  /14

  $2,956 per month

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 508, Highwood, IL 60040

  This two-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

  Christopher Dumitru Crosstown Realtors, Inc.

  440 Green Bay Rd Unit 508, Highwood, IL 60040
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  /2

  $190,000 Sold Oct 01, 2025

  307 Prairie Ave, Highwood, IL 60040

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft
  • Built 1923

  Last Sold Summary

  • 12% Below List Price
  • $192/SF
  • 3 Days On Market

  Current Estimated Value $264,739

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  307 Prairie Ave, Highwood, IL 60040
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  /19

  Est $538,329 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,443 Sq Ft

  125 Maple Ave, Highwood, IL 60040

  125 Maple Ave, Highwood, IL 60040
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  /2

  $150,000

  • Land
  • 0 Acre

  0 Wrendale Ave Unit MRD12487576, Highwood, IL 60040

  BUILD YOUR DREAM HOME ON THIS GREAT LOT IN SOUTHEAST HIGHWOOD! LOT HAS A WATER LINE INSTALLED AND AN EASEMENT FOR OTHER UTILITIES. GREAT LOCATION, WALK TO EVERYTHING IN BOOMING HIGHWOOD! ZONED R2 (residential). BUILD UP TO A 2,864 SQUARE FOOT SINGLE FAMILY HOME ON THIS LOT.

  Cory Albiani @properties Christie's International Real Estate

  0 Wrendale Ave Unit MRD12487576, Highwood, IL 60040
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  /15

  $2,812 per month

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft
  • Apartment for Rent

  246 Green Bay Rd Unit 313, Highwood, IL 60040

  Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine

  Christopher Dumitru Crosstown Realtors, Inc.

  246 Green Bay Rd Unit 313, Highwood, IL 60040
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  /29

  $350,000 Sold Jun 12, 2025

  238 Jeffreys Place, Highwood, IL 60040

  • 4 Beds
  • 3 Baths
  • 1,638 Sq Ft
  • Built 1950

  Last Sold Summary

  • $214/SF
  • 16 Days On Market

  Current Estimated Value $354,013

  Last Listing Agent Frank Rusin Four Seasons Realty, Inc.

  238 Jeffreys Place, Highwood, IL 60040
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  /15

  Est $419,606 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  144 Morgan Place, Highwood, IL 60040

  144 Morgan Place, Highwood, IL 60040
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  /13

  $2,358 per month

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

  440 Green Bay Rd Unit 503, Highwood, IL 60040

  This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

  Christopher Dumitru Crosstown Realtors, Inc.

  440 Green Bay Rd Unit 503, Highwood, IL 60040
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  /2

  $680,000 Sold Feb 14, 2025

  740 Deroo Loop, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 2,708 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $251/SF
  • 27 Days On Market

  Current Estimated Value $727,194

  Last Listing Agent Mona Hellinga @properties Christie's International Real Estate

  740 Deroo Loop, Highwood, IL 60040
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  /18

  Est $447,727 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft

  116 High St, Highwood, IL 60040

  116 High St, Highwood, IL 60040
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  /12

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  104 Michigan Ave, Highwood, IL 60040

  Charming & updated single-family Ranch home in the heart of Highwood! This cozy 2-bedroom, 1-bath home features a large, eat-in kitchen, a light-filled living room, an in-unit washer & dryer, and GFA + Central-Air. Plus, a private driveway parking space that can fit 2 cars. Excellent location near downtown Highwood's shops, all the great restaurants, lakefront, parks, schools, Metra stop & more!

  Derek DiSera Compass

  104 Michigan Ave, Highwood, IL 60040
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  /38

  $885,000 Sold Jun 30, 2025

  27 Rienzi Ln, Highwood, IL 60040

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $253/SF
  • 11 Days On Market

  Current Estimated Value $912,123

  Last Listing Agent Alison Wertheimer @properties Christie's International Real Estate

  27 Rienzi Ln, Highwood, IL 60040
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  /19

  Est $390,025 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,321 Sq Ft

  217 Prairie Ave, Highwood, IL 60040

  217 Prairie Ave, Highwood, IL 60040
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  /15

  $2,900 per month

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  327 Euclid Ave, Highwood, IL 60040

  Fantastic Highwood rental! Amazing yard with stone patio, fully fenced yard, 1 car attached garage, high ceilings, lots of storage, full basement. 3 bedrooms plus office. Updated kitchen appliances, hardwood floors throughout. Walk to town, Highwood restaurants, easy train access, convenient location to school and lake/beach. Move-in ready!

  Alison Wertheimer @properties Christie's International Real Estate

  327 Euclid Ave, Highwood, IL 60040
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  /29

  $375,000 Sold Dec 19, 2025

  228 Llewellyn Ave, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 1,480 Sq Ft
  • Built 1920

  Last Sold Summary

  • $253/SF
  • 43 Days On Market

  Last Listing Agent Sandra Locascio RE/MAX Suburban

  228 Llewellyn Ave, Highwood, IL 60040
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  /7

  Est $709,944 Not Listed For Sale

  • 7 Beds
  • 5 Baths
  • 3,113 Sq Ft

  250 Sard Place, Highwood, IL 60040

  250 Sard Place, Highwood, IL 60040
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  /9

  $2,395 per month

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Condo for Rent

  232 S Central Ave Unit 2, Highwood, IL 60040

  UNBELIEVABLE location in Highwood, across from Oak Terrace school. SECOND floor apt in 2-flat with private entry. Hardwood floors. Three bedrooms, living room, dining room & kitchen, one bath (tub/shower combo). Walk to everything in bustling Highwood, train, shopping, dining, Lake, library. No smoking apt/non-smoking building. No vaping. Gas heat bill shared between 2 units (cozy hot water

  Robin Wilson @properties Christie's International Real Estate

  232 S Central Ave Unit 2, Highwood, IL 60040
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  /2

  $830,000 Sold Jul 07, 2025

  754 Lyster Rd Unit D, Highwood, IL 60040

  • 3 Beds
  • 3 Baths
  • 2,405 Sq Ft
  • Built 1895

  Last Sold Summary

  • 11% Above List Price
  • $345/SF
  • 3 Days On Market

  Current Estimated Value $831,699

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

  754 Lyster Rd Unit D, Highwood, IL 60040
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  /4

  Est $379,780 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,075 Sq Ft

  239 Prairie Ave, Highwood, IL 60040

  239 Prairie Ave, Highwood, IL 60040
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  /26

  $255,000 Sold Jan 09, 2026

  330 Highwood Ave Unit 2A, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1984

  Last Sold Summary

  • 9% Below List Price
  • $170/SF
  • 7 Days On Market

  Last Listing Agent Andrew Langer @properties Christie's International Real Estate

  330 Highwood Ave Unit 2A, Highwood, IL 60040
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  /20

  Est $513,841 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  102 S Central Ave, Highwood, IL 60040

  102 S Central Ave, Highwood, IL 60040
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  /17

  $335,000 Sold Jul 01, 2025

  306 Ashland Ave, Highwood, IL 60040

  • 2 Beds
  • 1 Bath
  • 1,005 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Above List Price
  • $333/SF
  • 6 Days On Market

  Current Estimated Value $377,679

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

  306 Ashland Ave, Highwood, IL 60040
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  /2

  Est $521,334 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  52 S Central Ave, Highwood, IL 60040

  52 S Central Ave, Highwood, IL 60040

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