Cook, IL Homes

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  $2,850,000 Open Sun 12PM - 2PM

  • 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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  Explore Winnetka

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  /9

  $1,895 per month

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

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

  UNIT FEATURES:* Hardwood Floors* Restored Wood Trim* Updated Kitchen* SS Appliances* Washer/Dryer Combo* Quartz Countertop* Backsplash* Updated Bathroom* Mini Blinds* Ceiling Fans* Plenty of Closet SpaceSunshine dancing in little strips on the hardwood floors, elegant crown moldings, a fireplace, and airy living spaces - this apartment unit

  918 Green Bay Rd Unit 2D, Winnetka, IL 60093
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  /44

  $3,750,000 Sold Aug 01, 2025

  • 5,735 Sq Ft
  • $654/SF
  • 2 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1930

  180 De Windt Rd, Winnetka, IL 60093

  Experience the best of Winnetka living on nearly an acre in one of the village's most picturesque and prestigious locations. Tucked away behind winding, tree-lined streets, this spectacular historic renovation sits proudly on nearly a full acre of beautifully landscaped grounds. Located on prestigious De Windt Road and walking distance to top-rated Crow Island Elementary, this fairytale-like

  Grace Goro Compass

  180 De Windt Rd, Winnetka, IL 60093
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  /41

  Est $2,217,605 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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  /63

  $2,575,000

  • 4 Beds
  • 4.5 Baths
  • 3,973 Sq Ft

  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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  /26

  $8,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,450 Sq Ft
  • House for Rent

  80 Brier St, Winnetka, IL 60093

  Beautiful Property! Situated in the prestigious Joseph Sears Elementary and New Trier High School districts, this beautifully updated four-bedroom, three-and-a-half-bath home offers the perfect blend of classic charm and modern comfort in the heart of Winnetka. Step inside to an open-concept main level designed for both everyday living and entertaining. The chef's kitchen is outfitted with

  Martha Lozano RE/MAX City

  80 Brier St, Winnetka, IL 60093
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  /2

  $1,375,000 Sold Jul 31, 2025

  • 2,170 Sq Ft
  • $634/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  1101 Oak St, Winnetka, IL 60093

  Welcome to 1101 Oak Street - a beautifully updated home in the heart of the tree streets of Winnetka, offering the perfect blend of comfort, functionality, and fun. With 4 bedrooms, 2.1 baths, and an attached 2-car garage, this home is designed for easy everyday living and effortless entertaining. Step into a light-filled living room with gorgeous hardwood floors, seamlessly flowing into a

  David Chung Compass

  1101 Oak St, Winnetka, IL 60093
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  /34

  Est $2,364,896 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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  /49

  $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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  /9

  $2,145 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

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

  UNIT FEATURES* Hardwood Floors* Restored Wood Trim* Updated Kitchen* SS Appliances* Washer/Dryer Combo* Quartz Countertop* Backsplash* Updated Bathroom* Mini Blinds* Ceiling Fans* Plenty of Closet SpaceSunshine dancing in little strips on the hardwood floors, elegant crown moldings, a fireplace, and airy living spaces - this apartment unit

  918 Green Bay Rd Unit 3I, Winnetka, IL 60093
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  /2

  $935,000 Sold Jul 30, 2025

  • 2,264 Sq Ft
  • $413/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1925

  1442 Asbury Ave, Winnetka, IL 60093

  Located in one of Winnetka's most beloved neighborhoods, this classic Tudor offers timeless charm and endless potential. The spacious living room, featuring arched bookcases and fireplace, provides a cozy and inviting gathering space. An entertainment-sized dining room with built-ins adds both charm and functionality, The kitchen iwith table space, ample counter seating, and an adjacent family

  Sherry Molitor Compass

  1442 Asbury Ave, Winnetka, IL 60093
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  /29

  Est $2,062,739 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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  /85

  $2,799,000

  • 4 Beds
  • 4.5 Baths

  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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  /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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  /40

  $2,200,000 Sold Jul 30, 2025

  • 4,800 Sq Ft
  • $458/SF
  • 26 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 2004

  824 Humboldt Ave, Winnetka, IL 60093

  Tucked away on a serene cul-de-sac just steps from downtown Winnetka and Lake Michigan, this striking contemporary residence offers refined living in one of East Winnetka's most coveted locations. Designed by Gary Lee Partners and award-winning principal architect Sharlene Young, the home is a masterful expression of modern elegance, where innovative materials and meticulous craftsmanship create

  Michael Canzolino Chicago Properties Firm

  824 Humboldt Ave, Winnetka, IL 60093
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  /20

  Est $792,756 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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  /64

  $3,299,000

  • 6 Beds
  • 5.5 Baths
  • 6,384 Sq Ft

  646 Prospect Ave, Winnetka, IL 60093

  Spectacular East Winnetka in-town oasis on almost 1/2 acre of lushly landscaped grounds offers a singular opportunity to walk everywhere from a private, fully renovated classic located in a premier location with 150 ft frontage, just steps to town, train, and beach. Meticulously transformed and completely reimagined inside and out with one of the best first floor living spaces, this 6 bedrooms

  Paige Dooley Compass

  646 Prospect Ave, Winnetka, IL 60093
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  /7

  $3,595 per month

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

  772 Green Bay Rd, Winnetka, IL 60093

  Beautifully Remodeled Townhome in Prime Winnetka LocationLocated in the heart of Winnetka, this recently remodeled 2-bedroom, 1.5-bathroom townhome offers the perfect blend of modern living and charming neighborhood appeal. Just a short walk to Downtown Winnetka, Hubbard Woods, the beach, and the Metra station, this home is ideally situated for both convenience and

  772 Green Bay Rd, Winnetka, IL 60093
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  /45

  $2,201,894 Sold Jul 29, 2025

  • 5,000 Sq Ft
  • $440/SF
  • 7 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1894

  550 Oak St, Winnetka, IL 60093

  Opportunity to own and enhance a once-in-a-generation architecturally rich East Winnetka home built in 1894 and set on a beautifully landscaped .42-acre corner lot just steps from town, train, schools, Lake Michigan beaches and the Village Green. Bring your contractor with you to see this solidly built 5000 plus square foot, 5+ bedrooms, 3.2 baths vintage beauty that is surrounded by an iconic

  Paige Dooley Compass

  550 Oak St, Winnetka, IL 60093
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  /22

  Est $529,666 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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  /19

  $1,995,000

  • 4 Beds
  • 5 Baths
  • 3,700 Sq Ft

  314 Woodland Ave, Winnetka, IL 60093

  Handsome Georgian home underwent a complete restoration and remodel (2016) to preserve its antique charm and vintage details. Fantastic east Winnetka location - walk to Greeley, New Trier, Lake Michigan, and commuter train. Beautiful brick exterior with slate roof sets the tone for the entire home. kitchen with Decora cabinets, two spacious pantries, eat-in bar plus table space. 3 fireplaces,

  Margaret Goss @properties Christie's International Real Estate

  314 Woodland Ave, Winnetka, IL 60093
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  /25

  $7,500 per month

  • 4 Beds
  • 4.5 Baths
  • 2,690 Sq Ft
  • House for Rent

  116 Woodland Ave, Winnetka, IL 60093

  A Fabulous east Winnetka 4 bedroom, 4.1 bathroom home in sought after New Trier High School neighborhood. This sun-filled open floor plan home has high ceilings and a flexible floor plan with two primary bedroom options. Second floor boasts 3 bedrooms and two full bathrooms with hardwood floors and decorator accents. Third level has whole floor primary bedroom with a spa bathroom retreat and

  Kathryn Mangel @properties Christie's International Real Estate

  116 Woodland Ave, Winnetka, IL 60093
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  /86

  $3,175,000 Sold Jul 29, 2025

  • 5,651 Sq Ft
  • $562/SF
  • 3 Days On Market

  • 5 Beds
  • 9 Baths
  • Built 2004

  1575 Hickory Ln, Winnetka, IL 60093

  Welcome to this absolutely fabulous home nestled on a serene half-acre lot on picturesque Hickory Lane. Recently renovated, this residence offers three thoughtfully designed floors of luxurious living space, perfect for both relaxation and entertaining. As you enter, you're greeted by an impressive foyer that leads to the inviting living room, complete with a classic fireplace. The elegant dining

  Joanne Hudson Compass

  1575 Hickory Ln, Winnetka, IL 60093
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  /28

  Est $823,518 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,972 Sq Ft

  812 Oak St Unit 203, Winnetka, IL 60093

  812 Oak St Unit 203, Winnetka, IL 60093
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  /50

  $2,190,000 Pending

  • 4 Beds
  • 4 Baths
  • 4,460 Sq Ft

  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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  /16

  $3,500 per month

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

  553 Winnetka Ave, Winnetka, IL 60093

  Stunning Fully Renovated Townhome | 2 Bed, 1.5 Bath + Basement | Tandem ParkingThis beautifully remodeled townhome offers modern comfort, style, and convenience in every corner. Featuring two spacious bedrooms and one-and-a-half brand-new bathrooms, the unit has been thoughtfully upgraded from top to bottom.Key Features:Completely Renovated Interior: Enjoy a fresh, modern

  553 Winnetka Ave, Winnetka, IL 60093
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  /25

  $979,000 Sold Jul 25, 2025

  • 25 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  380 Green Bay Rd Unit 4D, Winnetka, IL 60093

  Coveted Hedge Row Penthouse, HARD TO FIND ONE FLOOR living in the Heart of Winnetka! This Northwest *End unit - is on the market for the first time! This is one of only a few on the top floor that are on the *BACK* side of the building - so you don't face Green Bat Road and the train tracks - and no one is above you - so it is quiet!! This 2 bedroom, 2 bath + den condo is spacious and neutral.

  Megan Mawicke @properties Christie's International Real Estate

  380 Green Bay Rd Unit 4D, Winnetka, IL 60093
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  /41

  Est $741,080 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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  /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

  355 Myrtle St, Winnetka, IL 60093
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  /20

  $8,800 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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  /39

  $1,860,000 Sold Jul 25, 2025

  • 3,500 Sq Ft
  • $531/SF
  • 32 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2004

  384 Provident Ave, Winnetka, IL 60093

  Sophisticated Living in the Heart of Winnetka Step into timeless elegance with this meticulously crafted custom home, ideally located on a picturesque tree-lined street in one of Winnetka's most desirable neighborhoods. Built in 2005, 384 Provident Avenue offers nearly 3,500 square feet of thoughtfully designed living space with quality craftsmanship, architectural character, and exceptional

  Scott Fishman Worth Clark Realty

  384 Provident Ave, Winnetka, IL 60093
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  /52

  Est $3,774,891 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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  /29

  $1,999,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,659 Sq Ft

  545 Sheridan Rd, Winnetka, IL 60093

  Welcome to this handsome Georgian located on highly sought-after Sheridan Road in Winnetka, IL, where timeless architecture meets modern living. This stately red brick residence offers an exceptional lifestyle just one half block from Lake Michigan, blending historic charm with contemporary comfort. The grand foyer sets the tone with classic detailing and gleaming hardwood floors that flow

  Julie Miller Compass

  545 Sheridan Rd, 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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  $1,525,000 Sold Jul 24, 2025

  • 3,440 Sq Ft
  • $443/SF
  • 3 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1924

  720 Willow Rd, Winnetka, IL 60093

  Introducing a stunning blend of timeless sophistication and modern functionality in the heart of Winnetka. This sun-drenched 5-bedroom, 4.1-bathroom home spans 3,440 square feet of thoughtfully designed living space, perfect for today's lifestyle. Step inside to discover hardwood floors, a striking stone fireplace, and Marvin windows that flood the home with natural light. The chef's kitchen is a

  Marlene Rubenstein Baird & Warner

  720 Willow Rd, Winnetka, IL 60093
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  /41

  Est $1,909,731 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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  /73

  $1,950,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 6,322 Sq Ft

  3 Woodley Manor, Winnetka, IL 60093

  Welcome to this beautifully maintained, turn-key home nestled on nearly an acre at the end of a quiet cul-de-sac-offering privacy, space, and convenience. Enjoy hard-to-find ranch-style living with a grand first-floor primary suite featuring a spacious walk-in closet and serene views of the professionally landscaped yard. Designed for easy living and effortless entertaining, the home boasts

  Tommy Choi Keller Williams ONEChicago

  3 Woodley Manor, 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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  /51

  $9,499,900 Sold Jul 22, 2025

  • 9,723 Sq Ft
  • $977/SF
  • 29 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 2021

  139 Sheridan Rd, Winnetka, IL 60093

  Summer is right around the corner, and 139 Sheridan is the ultimate lakefront escape. Built into the bluff and just steps to the water, this turnkey Morgante Wilson custom home is designed for effortless lake living. One of the last new construction homes allowed to build into the bluff, it offers a front-row seat to beach days, boat rides, and unforgettable summer memories. Incredible panoramic

  Jena Radnay @properties Christie's International Real Estate

  139 Sheridan Rd, Winnetka, IL 60093
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  /30

  Est $2,050,974 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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