Winnetka, IL Homes

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  /33

  $2,199,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,544 Sq Ft

  355 Myrtle St, Winnetka, IL 60093

  Timeless Elegance in the Heart of East Winnetka! Set on an expansive, professionally landscaped lot, this East Winnetka residence exudes timeless elegance and exceptional curb appeal. A grand foyer welcomes you into a home where classic architecture meets modern comfort. The richly paneled family room offers a sophisticated retreat, while the formal living room, bathed in natural light, features

  

  Mary Grant

  @properties Christie's International Real Estate

  (224) 571-9499

  355 Myrtle St, Winnetka, IL 60093
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  Explore Winnetka

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  /42

  $2,195 - $2,395 per month

  • 1 - 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  545 Chestnut St, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry

  545 Chestnut St, Winnetka, IL 60093
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  /32

  $2,700,000 Sold Sep 16, 2025

  • 6,500 Sq Ft
  • $415/SF

  • 5 Beds
  • 5.5 Baths
  • Built 1925

  1010 Hubbard Place, Winnetka, IL 60093

  Walk to Hubbard Woods from this traditional cedar shake-style home on a spectacular .82 ACRE . Longtime homeowners recently added 1st FLOOR PRIMARY SUITE and UPDATED KITCHEN. Well-scaled formal living room and dining room. Updated white kitchen in 2023 with island opens to family room with vaulted ceiling, built-ins and wet bar. Expansive all-season sun room offers southern exposure overlooking

  Elise Rinaldi @properties Christie's International Real Estate

  1010 Hubbard Place, Winnetka, IL 60093
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  /41

  Est $2,333,067 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,828 Sq Ft

  110 N Sheridan Rd, Winnetka, IL 60093

  110 N Sheridan Rd, Winnetka, IL 60093
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  /50

  $2,649,000

  • 5 Beds
  • 3.5 Baths
  • 4,800 Sq Ft

  180 Apple Tree Rd, Winnetka, IL 60093

  Storybook Cape Cod set on enchanting Apple Tree Road complete with that magical sidewalk to Crow Island School, this red brick colonial accented with classic black shutters and white trim offers timeless comfort in a very special nook! Nestled on a lush half-acre lot with mature trees, a circular drive & attached 2-car garage accented by plantation shutter windows, this home radiates charm with

  Jena Radnay @properties Christie's International Real Estate

  180 Apple Tree Rd, Winnetka, IL 60093
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  /28

  $4,300 per month

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • House for Rent

  381 Wilson St, Winnetka, IL 60093

  Welcome to 381 Wilson, a beautifully maintained and inviting Cape Cod-style home filled with warmth, character, and natural light. Perfectly situated just blocks from downtown Winnetka and the lake, this home offers the ideal blend of comfort, space, and convenience. Step into the welcoming living room, featuring lovely views of the backyard and built-in shelving-perfect for cozy evenings or

  Pamela McClamroch Coldwell Banker Realty

  381 Wilson St, Winnetka, IL 60093
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  /32

  $1,785,000 Sold Sep 15, 2025

  • 2,826 Sq Ft
  • $632/SF
  • 4 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1925

  1473 Edgewood Ln, Winnetka, IL 60093

  What a stunning transformation! Tucked away on a quiet, tree-lined street in coveted Hubbard Woods, this classic brick home has been completely transformed through an extensive renovation, seamlessly blending timeless elegance with modern luxury. With 4 bedrooms & 4.5 bathrooms, this residence offers exceptional craftsmanship & design at every turn. Wide-plank white oak floors lead you through

  Alicja Skibicki Baird & Warner

  1473 Edgewood Ln, Winnetka, IL 60093
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  /34

  Est $2,455,041 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,947 Sq Ft

  1189 Asbury Ave, Winnetka, IL 60093

  1189 Asbury Ave, Winnetka, IL 60093
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  /36

  $2,699,000

  • 6 Beds
  • 5.5 Baths
  • 4,295 Sq Ft

  519 Cedar St, Winnetka, IL 60093

  Exquisite, like-new home in prime East Winnetka location overlooking the breathtaking Village Green! This classic home has been completely revitalized and enhanced from top to bottom under the expertise of Morgante Wilson (2018), showcasing the highest quality, luxury finishes and timeless design. A truly elegant home spanning over 4,200SF (above-grade) with an ideal floor plan that features

  Paige Dooley Compass

  519 Cedar St, Winnetka, IL 60093
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  /20

  $2,395 per month

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

  811 Elm St Unit A07C, Winnetka, IL 60093

  811 ElmElm + ChestnutWinnetka$2395 per MonthAvailable: NowAVAILABLE NOW! Handsome two bedroom, one bathroom in heart of downtown Winnetka features rehabbed kitchen, spacious living area, equal sized bedrooms, great closet space, rehabbed bathroom, hardwood floors throughout, laundry in unit, and pets welcome! Steps to Winnetka Metra stop, shops, restaurants, Public

  811 Elm St Unit A07C, Winnetka, IL 60093
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  /63

  $2,450,000 Sold Sep 15, 2025

  • 3,973 Sq Ft
  • $617/SF
  • 16 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1953

  1300 Hackberry Ln, Winnetka, IL 60093

  This is the quintessential All-American Beauty nestled on private lane in desirable Winnetka on a half acre with a pool! This home was completely rebuilt and redsigned for today's lifestyle in (2003-2004) - it is impeccable inside and out! Not much remains of the original home. The attention detail is everywhere...outstanding craftmanship and exceptional millwork throughout. A large foyer with

  Megan Mawicke @properties Christie's International Real Estate

  1300 Hackberry Ln, Winnetka, IL 60093
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  /29

  Est $2,193,067 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,400 Sq Ft

  1060 Spruce St, Winnetka, IL 60093

  1060 Spruce St, Winnetka, IL 60093
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  /36

  $3,999,000 Open Sun 1PM - 3PM

  • 6 Beds
  • 7.5 Baths
  • 8,303 Sq Ft

  1015 Sheridan Rd, Winnetka, IL 60093

  Nestled on a private lane east of Sheridan Road, this distinguished residence combines timeless sophistication with everyday livability. With over 6 bedrooms (including an in-law/guest suite) and 7.1 baths, the home is designed to accommodate a variety of lifestyles - whether hosting large gatherings, working from home, or enjoying intimate quiet time. A sunlit two-story foyer with a sweeping

  Linda Martin Coldwell Banker Realty

  1015 Sheridan Rd, Winnetka, IL 60093
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  /15

  $15,000 per month

  • 6 Beds
  • 5.5 Baths
  • House for Rent

  82 Woodley Rd, Winnetka, IL 60093

  Fantastic furnished short-term rental opportunity! Available August 12th, 2025 thru May 31st, 2026. This exquisite residence sits on just over 1.5 professionally, landscaped acres in sought after Indian Hill. The home boasts 6 bedrooms and 5.1 baths and has been tastefully renovated and lovingly maintained throughout the years. The incredible chef's kitchen features top of the line appliances

  Michael Mitchell @properties Christie's International Real Estate

  82 Woodley Rd, Winnetka, IL 60093
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  /31

  $1,650,000 Sold Sep 05, 2025

  • 4,700 Sq Ft
  • $351/SF
  • 23 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1955

  11 Longmeadow Rd, Winnetka, IL 60093

  Spectacular home situated on 1/2 acre with lush landscaping on one of Winnetka's prettiest streets. This inviting home offers generous living rm w/fireplace, dining rm w/ fireplace, family rm w/fireplace, updated kitchen with quartz countertops, office with built-ins and screened-in porch overlooking gorgeous salt water pool. Beautifully updated, freshly painted, hardwood floors, new carpeting

  Margaret Murphy Burton @properties Christie's International Real Estate

  11 Longmeadow Rd, Winnetka, IL 60093
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  /20

  Est $905,716 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,745 Sq Ft

  812 Oak St Unit 201, Winnetka, IL 60093

  812 Oak St Unit 201, Winnetka, IL 60093
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  /52

  $4,800,000

  • 6 Beds
  • 7 Baths
  • 8,549 Sq Ft

  640 Hill Rd, Winnetka, IL 60093

  Greeley and Winnetka schools!! Welcome to Meadowpool - a distinguished Tudor residence nestled on a meticulously landscaped and wooded one acre lot. Built in 1923, the home's design exudes classic Tudor charm with stucco and stone exterior and a slate roof. The entryway is adorned with leaded glass windows and rich woodwork and leads to a charming living room featuring a limestone fireplace. The

  Deborah Richwine @properties Christie's International Real Estate

  640 Hill Rd, Winnetka, IL 60093
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  /16

  $2,250 per month

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Condo for Rent

  953 Westmoor Rd Unit 1, Winnetka, IL 60093

  Beautiful and bright 3 Bedroom unit with large private patio. Hardwood floors throughout and bedrooms upstairs. One and one half baths and in unit laundry. One garage spot included and easy street parking. Living room dining room opens to the stone patio. Updated kitchen with stainless steel appliances. Master bedroom and 2 large bedrooms - good closet space and storage in the attic with pull

  953 Westmoor Rd Unit 1, Winnetka, IL 60093
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  /48

  $1,820,000 Sold Sep 03, 2025

  • 5,445 Sq Ft
  • $334/SF
  • 7 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1956

  1118 Mount Pleasant Rd, Winnetka, IL 60093

  Welcome to this beautifully maintained 5 bedroom, 4.1 bathroom Colonial home with circular driveway nestled on a half acre at the end of a quiet street in Crow island offering privacy, space, and convenience. Enjoy the hard-to-find grand first-floor primary suite featuring a well designed bathroom, spacious walk-in closet and serene views of the professionally landscaped yard. Designed for easy

  Kelly Lundin Compass

  1118 Mount Pleasant Rd, Winnetka, IL 60093
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  /22

  Est $563,481 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,642 Sq Ft

  630 Winnetka Mews Unit 402, Winnetka, IL 60093

  630 Winnetka Mews Unit 402, Winnetka, IL 60093
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  /46

  $2,739,000

  • 6 Beds
  • 6 Baths
  • 7,000 Sq Ft

  62 Woodley Rd, Winnetka, IL 60093

  Gracefully tucked away on 1.55 acres of lush manicured grounds, 62 Woodley Road is a true Southern-inspired masterpiece reimagined for today's living. From the moment you approach the iconic black lacquered screen door with its Chippendale detail, you're drawn into a world of classic sophistication. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet

  Jena Radnay @properties Christie's International Real Estate

  62 Woodley Rd, Winnetka, IL 60093
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  /20

  $7,800 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  510 Ash St, Winnetka, IL 60093

  You will love this charming Winnetka home in prime east location on a coveted street two blocks from Lake Michigan. Easy walk to Greeley School, New Trier High School, Metra train, bike trails, beaches and town. Special features include large sunlit rooms, beautiful hardwood floors, a large eat-in kitchen with all stainless steel appliances and granite counters, a first floor office/ bedroom with

  Beth Groebe Coldwell Banker Realty

  510 Ash St, Winnetka, IL 60093
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  /11

  $875,000 Sold Aug 29, 2025

  • 1,920 Sq Ft
  • $456/SF
  • 53 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1928

  1253 Cherry St, Winnetka, IL 60093

  Motivated seller! A beautiful red brick home, center entrance colonial, in a prime Winnetka location that gushes with natural sunlight. The combination of a prime location coupled with a superb floor plan and great bones puts this in a unique category all by itself. Walk to Crow Island, Skokie, Washburne and park district field/sports complex.: two fireplaces, wood burning and gas, walk up attic

  Misael Chacon Beycome brokerage realty LLC

  1253 Cherry St, Winnetka, IL 60093
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  /41

  Est $773,859 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,931 Sq Ft

  720 Green Bay Rd Unit 2D, Winnetka, IL 60093

  720 Green Bay Rd Unit 2D, Winnetka, IL 60093
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  /64

  $3,200,000

  • 6 Beds
  • 6 Baths
  • 7,914 Sq Ft

  100 Old Green Bay Rd, Winnetka, IL 60093

  Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside

  Joanne Hudson Compass

  100 Old Green Bay Rd, Winnetka, IL 60093
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  /11

  $2,045 per month

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

  910 Green Bay Rd Unit 918-3I, Winnetka, IL 60093

  910 Green Bay Rd Unit 918-3I, Winnetka, IL 60093
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  /85

  $2,550,000 Sold Aug 29, 2025

  • 4,591 Sq Ft
  • $555/SF
  • 78 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1976

  1098 Fisher Ln, Winnetka, IL 60093

  Welcome to your dream home, just steps from the Hubbard Woods shops restaurants, park and train, and Lake Michigan. Set on over an acre with lush lawns and ravine views, this property offers a tranquil setting like no other. Enjoy an outdoor spa with a fireplace and outdoor shower, all with breathtaking views and privacy. Inside, find a beautiful kitchen with a center island which opens to the

  Joanne Hudson Compass

  1098 Fisher Ln, Winnetka, IL 60093
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  /52

  Est $4,006,479 Not Listed For Sale

  • 6 Beds
  • 9 Baths
  • 10,753 Sq Ft

  102 Longmeadow Rd, Winnetka, IL 60093

  102 Longmeadow Rd, Winnetka, IL 60093
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  /48

  $3,999,900

  • 8 Beds
  • 7 Baths
  • 7,168 Sq Ft

  5 Woodley Rd, Winnetka, IL 60093

  Reminiscent of the timeless white painted Colonial retreats off the East Coast of Hyannis Port, this Winnetka estate set on 1.4 acres of gracious grounds captures that same coastal charm right here in the North Shore. Set on premier Woodley Road with a beautiful natural canopy of mature trees, this 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a

  Jena Radnay @properties Christie's International Real Estate

  5 Woodley Rd, Winnetka, IL 60093
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  /50

  $9,100 per month

  • 4 Beds
  • 3.5 Baths
  • 2,344 Sq Ft
  • House for Rent

  1443 Scott Ave, Winnetka, IL 60093

  Adorable, freshly renovated and updated, with loads of open space and light house.This is a 4 bedroom, 3.5 bath with partially finished basement home. Conveniently located at Winnetka's Hubbard Woods, where you find shopping, restaurants, parks, train station and many more. Excellent school district with great neighborhood. This house features large kitchen with pennicula, beautiful quartz

  Derek Eisenberg Continental Real Estate Group

  1443 Scott Ave, Winnetka, IL 60093
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  /2

  $31,250,000 Sold Aug 29, 2025

  • 13,894 Sq Ft
  • $2,249/SF
  • 145 Days On Market

  • 7 Beds
  • 13 Baths
  • Built 1928

  419 Sheridan Rd, Winnetka, IL 60093

  Defining a league of its own, this is the chance of a lifetime to own the most iconic lakefront estate in IL. The "Windsor House" has been elevated to a new grandeur of living with a best in class collaboration lead by nationally recognized interior design, landscape architects & coastal engineering teams. Gloriously expanded to 2.3 acres with the purchase of 429 Sheridan transformed into a

  Jena Radnay @properties Christie's International Real Estate

  419 Sheridan Rd, Winnetka, IL 60093
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  /41

  Est $2,051,206 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,797 Sq Ft

  244 Mary St, Winnetka, IL 60093

  244 Mary St, Winnetka, IL 60093
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  /61

  $3,295,000

  • 4 Beds
  • 7 Baths
  • 5,900 Sq Ft

  358 Winnetka Ave, Winnetka, IL 60093

  Incredible Coveted Home with 5 bedrooms, 5.2 bathrooms, 3 garages on 1/3 acre property boasts Winnetka address and Kenilworth School District. Built in 2004, this beautiful brick home feels like new construction with a complete first floor renovation in 2019 and upgrades throughout the home. As you enter the sun filled foyer, you are greeted with an open floor plan and 9'.5" ceilings. Flanking

  Kathryn Mangel @properties Christie's International Real Estate

  358 Winnetka Ave, Winnetka, IL 60093
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  /42

  $2,195 - $2,395 per month

  • 1 - 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  545 Chestnut St, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry

  545 Chestnut St, Winnetka, IL 60093
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  /15

  $1,675,000 Sold Aug 28, 2025

  • 4,352 Sq Ft
  • $385/SF
  • 38 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2025

  917 Willow Rd, Winnetka, IL 60093

  Enjoy a completely custom home in the heart of Winnetka. Conveniently located only blocks from Crow Island Elementary and walking distance to local favorite boutiques and restaurants including Pomeroy, 501 Local, La Taquiza and Tocco. Built by fourth generation custom home builders, this thoughtful floorplan features 5 bedrooms, 5 bathrooms, a finished lower level and a chef's kitchen ready for

  Grace Goro Compass

  917 Willow Rd, Winnetka, IL 60093
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  /30

  Est $2,080,813 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,656 Sq Ft

  285 Woodlawn Ave, Winnetka, IL 60093

  285 Woodlawn Ave, Winnetka, IL 60093
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  /51

  $2,499,000

  • 6 Beds
  • 7 Baths
  • 5,350 Sq Ft

  1423 Asbury Ave, Winnetka, IL 60093

  Better than NEW! Impeccably renovated 6BR/5.2BA center-entry colonial set on an oversized (66 x 159) professionally landscaped lot. This four-level home features abundant natural light, oversized windows, wide room openings, custom millwork and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end finishes and thoughtful design exist at every turn. First floor includes a

  Laura McCain Compass

  1423 Asbury Ave, Winnetka, IL 60093
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  /10

  $2,195 per month

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

  545 Chestnut St Unit E817-306, Winnetka, IL 60093

  Wonderful Vintage Landmark Building in WinnetkaIn the heart of downtown Winnetka, these units are surrounded by some incredible restaurants and shops including Peet’s Coffee and the Book Stall. This location is within walking distance of local schools and parks.Amenities:- Hardwood Floors- Separate Kitchen and Dining Area- Updated Bathroom- Miniblinds- Ceiling

  545 Chestnut St Unit E817-306, Winnetka, IL 60093
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  /50

  $2,050,000 Sold Aug 28, 2025

  • 4,460 Sq Ft
  • $460/SF
  • 320 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2022

  803 Pine St, Winnetka, IL 60093

  Absolute perfection in the heart of East Winnetka! Completed in 2022, this contemporary two-story masterpiece offers the perfect combination of luxury and convenience. Situated on a beautifully landscaped lot, the home is adorned with Brazilian Ipe Norwegian board siding, triple-pane windows, and a stunning modern front door, all adding to its striking curb appeal. The open-concept first floor

  Michael Kelly Compass

  803 Pine St, Winnetka, IL 60093
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  /29

  Est $946,549 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,637 Sq Ft

  1103 Willow Rd, Winnetka, IL 60093

  1103 Willow Rd, Winnetka, IL 60093

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