Highwood, IL Homes

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  /11

  $795,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,500 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.

  Jorge Zea Jorge Zea Managing Broker

  535 Lockard Ln, Highwood, IL 60040
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  /51

  $1,750 - $2,930 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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  /13

  $2,019 per month

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

  546 Green Bay Rd Unit 203, Highwood, IL 60040

  Luxury Living in the Heart of Highwood! This stunning 1-bedroom, 1-bathroom apartment offers modern elegance with a private terrace and generous closet space. Nestled in Highwood's vibrant historic downtown, you're just steps from premier shopping, fine dining, and the Metra station for effortless commuting. The building features a selection of 1, 2, and 3-bedroom residences, each thoughtfully

  Christopher Dumitru Crosstown Realtors, Inc.

  546 Green Bay Rd Unit 203, 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 $639,741 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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  /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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  /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 $513,601 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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  /26

  $280,000 Pending

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

  330 Highwood Ave Unit 2A, Highwood, IL 60040

  Discover this spacious condominium nestled in a quiet and desirable residential community. Enjoy the updated primary bathroom, a refreshed hall bath, upgraded kitchen, marble foyer and relaxing screened-in porch. The large primary bedroom offers exceptional comfort and privacy, while walk-in closets in both bedrooms provide ample storage. A wonderful opportunity to own a move-in-ready home with

  Andrew Langer @properties Christie's International Real Estate

  330 Highwood Ave Unit 2A, Highwood, IL 60040
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  /13

  $1,941 per month

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

  546 Green Bay Rd Unit 407, Highwood, IL 60040

  Luxury Living in the Heart of Highwood! This stunning 1-bedroom, 1-bathroom apartment offers modern elegance with a private terrace and generous closet space. Nestled in Highwood's vibrant historic downtown, you're just steps from premier shopping, fine dining, and the Metra station for effortless commuting. The building features a selection of 1, 2, and 3-bedroom residences, each thoughtfully

  Christopher Dumitru Crosstown Realtors, Inc.

  546 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

  Last Listing Agent Karen Chien-Rooney Compass

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

  Est $449,235 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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  /28

  $649,900 New Construction

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

  525 Lockard Ln, Highwood, IL 60040

  Custom units starting at 599k for 1,800sq ft. Ask about new updated plans. Images are Architectural renderings and virtual images of how the property might look.

  Jorge Zea Jorge Zea Managing Broker

  525 Lockard Ln, 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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  /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

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  307 Prairie Ave, Highwood, IL 60040
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  /19

  Est $543,918 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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  /22

  $535,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,101 Sq Ft

  221 Burchell Ave, Highwood, IL 60040

  Exceptional Highwood Residence with Charming Coach House! Discover this beautifully updated 3-bedroom, 2-bath home perfectly situated near the heart of downtown Highwood. Featuring new hardwood floors throughout the second level and hardwood on the main living floor, this home blends classic charm with modern comfort. The spacious eat-in kitchen offers a large pantry, while the generous dining

  Carol Santi Coldwell Banker Realty

  221 Burchell Ave, Highwood, IL 60040
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  /15

  $2,730 per month

  • 2 Beds
  • 2 Baths
  • 966 Sq Ft
  • Apartment for Rent

  546 Green Bay Rd Unit 305, Highwood, IL 60040

  Luxury Living in the Heart of Highwood! This stunning 2-bedroom, 2-bathroom apartment offers modern elegance with a private terrace and generous closet space. Nestled in Highwood's vibrant historic downtown, you're just steps from premier shopping, fine dining, and the Metra station for effortless commuting. The building features a selection of 1, 2, and 3-bedroom residences, each thoughtfully

  Christopher Dumitru Crosstown Realtors, Inc.

  546 Green Bay Rd Unit 305, 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 $352,351

  Last Listing Agent Frank Rusin Four Seasons Realty, Inc.

  238 Jeffreys Place, Highwood, IL 60040
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  /15

  Est $426,366 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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  /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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  /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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  /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 $732,545

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

  740 Deroo Loop, Highwood, IL 60040
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  /18

  Est $450,774 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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  /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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  /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 $909,047

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

  27 Rienzi Ln, Highwood, IL 60040
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  /25

  Est $397,287 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,753 Sq Ft

  129 Pleasant Ave, Highwood, IL 60040

  129 Pleasant Ave, 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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  /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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  /19

  Est $395,017 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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  /13

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • Apartment for Rent

  423 Funston Ave Unit 1R, Highwood, IL 60040

  Lovely 2 bedroom apartment close to all the action in vibrant Highwood. This inviting home features a modern kitchen with granite countertops, classic white Shaker-style cabinets, and gas cooking. Both bedrooms are spacious and versatile. The spacious and spa like bathroom features an extra large vanity and steam shower. The home also features central heat and air conditioning, washer and dryer

  Axel Cohen Compass

  423 Funston Ave Unit 1R, Highwood, IL 60040
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  /20

  $380,000 Sold Jan 02, 2025

  522 N Central Ave, Highwood, IL 60040

  • 6 Beds
  • 3 Baths
  • 2,480 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $153/SF
  • 27 Days On Market

  Current Estimated Value $529,259

  Last Listing Agent Christopher Lobrillo Grandview Realty, LLC

  522 N Central Ave, Highwood, IL 60040
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  /7

  Est $710,616 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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  /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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  /29

  $495,000 Sold Dec 27, 2024

  247 Sheridan Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  Last Sold Summary

  • $314/SF
  • 3 Days On Market

  Current Estimated Value $409,580

  Last Listing Agent Lily Hosseini Engel & Voelkers Chicago North Shore

  247 Sheridan Ave, Highwood, IL 60040
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  /4

  Est $375,276 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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