Winnetka, IL Homes for Sale with Garage

• 

  

  

  /57

  $2,660,000

  $335K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 5,500 Sq Ft

  527 Warwick Rd, Kenilworth, IL 60043

  Fully Renovated 6BR 5.5BA Classic Home in Unbeatable East Kenilworth Location. This Elegant home sits on a large lot on one of Kenilworth's most serene streets. FIRST FLOOR: Elegant LR w/ Thibault Grasscloth Wallpaper & Custom Solid Wood Built Ins, Custom Handmade Mosaic Entry, Traditional DR w/ Brick Fireplace. Kitchen boasts both a Butler's Pantry and Prep Station, Quartz Countertops and

  

  Paul Harb

  Wilmette Real Estate & Management Company LLC

  527 Warwick Rd, Kenilworth, IL 60043
• Explore Winnetka

• 

  

  

  /34

  $1,495,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 4,064 Sq Ft

  1347 Sunview Ln, Winnetka, IL 60093

  Set on a professionally landscaped half-acre in the coveted Hubbard Woods School District, this exceptional 4-bedroom, 3.1-bath home offers expansive living spaces, refined finishes, and an effortless floor plan. A gracious foyer opens to an elegant circular layout featuring a sun-filled living room anchored by a striking fireplace, a handsome private office overlooking the landscaped grounds,

  

  Mary Grant

  @properties Christie's International Real Estate

  1347 Sunview Ln, Winnetka, IL 60093
• 

  

  

  /50

  $2,499,900

  Pending

  • 6 Beds
  • 6 Baths
  • 5,458 Sq Ft

  406 Woodley Woods, Winnetka, IL 60093

  MULTIPLE OFFERS! HIGHEST AND BEST DUE 5PM ON 4/24/26! Set at the end of a quiet, private cul-de-sac on a rare acre lot, this custom-built Georgia marble home with an inground pool showcases timeless elegance and exceptional craftsmanship in the Woodley neighborhood of Winnetka. A gracious foyer with stained glass double entry doors, marble tile floors, fresh paint, and a sparkling crystal

  Jason Wagner Greystone Realty

  406 Woodley Woods, Winnetka, IL 60093
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  /61

  $4,499,000

  • 5 Beds
  • 7 Baths
  • 6,697 Sq Ft

  528 Roslyn Rd, Kenilworth, IL 60043

  Stunning French Manor house on one of East Kenilworth's most beautiful streets. Stylish and sophisticated, this unique home is perfectly situated near the lake, train, Sears School, and New Trier High School. Luxurious landscaping envelopes the property, highlighted by a serene backyard pool. Expansive marble foyer opens to gracious living room and charming dining room. Dramatic floating

  Dayle Lively Baird & Warner

  528 Roslyn Rd, Kenilworth, IL 60043
• 

  

  

  /19

  $360,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  134 Green Bay Rd Unit 104, Winnetka, IL 60093

  Sun-drenched mornings define this coveted two-bedroom, two-bathroom residence. Located in a premier building within a highly sought-after location, this home welcomes you with a bright, cheerful, thoughtful layout. The east-facing exposure ensures the living spaces are bathed in natural light, while the charming private balcony offers the perfect spot for a morning coffee or an evening breeze.

  Dinny Dwyer Compass

  134 Green Bay Rd Unit 104, Winnetka, IL 60093
• 

  

  /84

  $3,850,000

  Pending

  • 7 Beds
  • 5.5 Baths

  605 Arbor Vitae Rd, Winnetka, IL 60093

  A RARE OPPORTUNITY...in the HEART of East Winnetka, this iconic home is among the Village's most admired residences! Commanding an elevated setting atop Arbor Vitae, the magnificent home was designed by renowned architects Otis & Clark and has earned its grand reputation as Winnetka's own "Castle on the Hill." It boasts one of the most exceptional backyard retreats! Featured in Luxe Magazine and

  Megan Panje-Wilson Jameson Sotheby's International Realty

  605 Arbor Vitae Rd, Winnetka, IL 60093
• 

  

  /18

  $5,975,000

  New Construction

  • 7 Beds
  • 8.5 Baths
  • 11,000 Sq Ft

  455 Sheridan Rd, Winnetka, IL 60093

  New magnificent transitional home with approximately 11,000 square feet finished space. Exterior is constructed of brick and limestone with slate roof which represents timeless construction. Close to Plaza del Lago with its numerous shops and restaurants, Kenilworth beach, schools and train the house features 7 bedrooms, 8.1 bath, 3 fireplaces, spectacular kitchen with top-of-the-line appliances

  Milena Birov @properties Christie's International Real Estate

  455 Sheridan Rd, Winnetka, IL 60093
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  /34

  $2,195,000

  • 6 Beds
  • 6 Baths
  • 4,142 Sq Ft

  757 Locust St, Winnetka, IL 60093

  757 Locust is a stunning 6-bedroom, 4.2-bath home set on a 15,000-square-foot lot in the heart of Hubbard Woods. Built in 1920 and thoughtfully updated over the years, this exceptional residence blends timeless architecture with modern comfort, with large, light-filled rooms, soaring ceilings, and oversized windows that create a sense of space throughout. A bluestone walkway leads to a gracious

  Lisa Weis @properties Christie's International Real Estate

  757 Locust St, Winnetka, IL 60093
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  /21

  $2,785,000

  • 6 Beds
  • 5.5 Baths

  82 Woodley Rd, Winnetka, IL 60093

  Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush,

  Michael Mitchell @properties Christie's International Real Estate

  82 Woodley Rd, Winnetka, IL 60093
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  /67

  $7,999,900

  • 6 Beds
  • 9 Baths
  • 10,588 Sq Ft

  919 Hill Rd, Winnetka, IL 60093

  An extraordinary "boutique hotel" living experience, impeccably situated in the heart of Winnetka. Beyond a stately solid-iron gate adorned with gold medallion accents lies a private sanctuary just 18 miles from Chicago and less than half a mile from the sandy shores of Lake Michigan. Evoking the glamour and grandeur of a Roaring Twenties estate, this remarkable residence channels the elegance of

  Jena Radnay @properties Christie's International Real Estate

  919 Hill Rd, Winnetka, IL 60093
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  /58

  $2,099,000

  Pending

  • 5 Beds
  • 5.5 Baths

  920 Pine Tree Ln, Winnetka, IL 60093

  Easy living at its best! Discerning updates and renovations combine with impeccable maintenance to create this exceptional home with the ease of one-floor living with outstanding design, gracious proportions, and an effortless flow throughout. Set on a gorgeous 4/10 acre property, the grounds are a true private retreat, featuring lush, professional landscaping, mature trees, colorful plantings,

  Joanne Hudson Compass

  920 Pine Tree Ln, Winnetka, IL 60093
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  /45

  $2,199,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 3,426 Sq Ft

  1258 Scott Ave, Winnetka, IL 60093

  Beautifully renovated and thoughtfully reimagined, this exceptional brick and stucco Colonial located in the heart of Hubbard Woods sits on an expanded 64 X 160 parcel, blending timeless architecture with today's most desired amenities and refined finishes. A total interior renovation completed in 2004 with added exterior renovation in 2006 and 2017 redesigns, transformed the home into a

  Sara Sullivan Compass

  1258 Scott Ave, Winnetka, IL 60093
• 

  

  /41

  $1,795,000

  • 3 Beds
  • 2.5 Baths
  • 4,356 Sq Ft

  180 Westview Rd, Winnetka, IL 60093

  BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale

  Cody McGuire @properties Commercial

  180 Westview Rd, Winnetka, IL 60093
• 

  /2

  $2,799,388

  New Construction Pending

  • 6 Beds
  • 5.5 Baths

  510 Provident Ave, Winnetka, IL 60093

  Situated on a quiet, highly desirable street in the heart of Winnetka, 510 Provident represents a thoughtful expression of modern North Shore architecture - where structural integrity, material quality, and enduring design converge. This new construction home offers six-bedrooms, six baths, over-scaled proportions and architectural clarity throughout. Ten-foot ceilings create an elevated sense of

  John Park John Park

  510 Provident Ave, Winnetka, IL 60093
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  /38

  $3,495,000

  • 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 Winnetka residence offers privacy, scale, quality craftsmanship, and exceptional everyday livability in one of the North Shore's most coveted east-side locations. Designed for elegant entertaining, multigenerational living, work-from-home flexibility, and relaxed daily comfort, the home features 6+ bedrooms, including a private

  Linda Martin Coldwell Banker Realty

  1015 Sheridan Rd, Winnetka, IL 60093
• 

  

  /36

  $1,399,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,992 Sq Ft

  1225 Elm St, Winnetka, IL 60093

  Privately tucked on an extra wide 1/3rd acre property, this fully re-imagined mid-century modern home offers exceptional design and incredible vistas of its lushly landscaped property. Thoughtfully curated with attention to detail and a sophisticated eye for design, the home blends timeless architecture with abundant natural beauty, right in the heart of Winnetka. A super chic, modern kitchen

  Paige Dooley Compass

  1225 Elm St, Winnetka, IL 60093
• 

  

  /27

  $825,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,938 Sq Ft

  376 Rosewood Ave, Winnetka, IL 60093

  Don't let the storybook cottage charm fool you-this home lives much larger than it appears from the outside. Thoughtfully expanded and beautifully maintained, it offers generous living spaces while retaining all the warmth, character, and timeless appeal that make cottage-style homes so beloved. The main level features a spacious, sun-filled living room anchored by a beautiful wood-burning

  Courtney Elko Jameson Sotheby's International Realty

  376 Rosewood Ave, Winnetka, IL 60093
• 

  

  /22

  $1,195,000

  Pending

  • 3 Beds
  • 4 Baths
  • 2,717 Sq Ft

  72 Warwick Rd, Winnetka, IL 60093

  Ideally located in coveted East Winnetka, just moments from Joseph Sears School, Lake Michigan beaches, the Metra train, and New Trier High School's East Campus, this beautifully updated home offers the perfect combination of charm, functionality, and an unbeatable location. Featuring 3 bedrooms, 4 full bathrooms, and a flexible first-floor office or optional 4th bedroom, the home is thoughtfully

  Kathryn Mangel @properties Christie's International Real Estate

  72 Warwick Rd, Winnetka, IL 60093
• 

  

  /44

  $1,795,000

  Pending

  • 5 Beds
  • 3.5 Baths

  1037 Oak St, Winnetka, IL 60093

  Located in the heart of Winnetka and within the highly sought-after Crow Island School District, this impeccably maintained 5-bedroom, 3.1-bath home checks every box. Thoughtfully reimagined and beautifully updated, the first floor offers exceptional flow, abundant natural light and timeless finishes throughout. At the center of the home is the stunning kitchen, completely gutted and renovated in

  Catherine Dunlop @properties Christie's International Real Estate

  1037 Oak St, Winnetka, IL 60093
• 

  

  /60

  $4,995,000

  • 6 Beds
  • 9 Baths
  • 7,480 Sq Ft

  1380 Westmoor Trail, Winnetka, IL 60093

  It is exceptionally rare to find a privately set masterpiece with sweeping views of the Winnetka Golf Course that also offers the opportunity to step directly into a freshly completed 2025/2026 designer showcase renovation. Nestled on a beautifully landscaped half-acre site overlooking the golf course, this extraordinary stone residence has been impeccably transformed through a comprehensive

  Lori Nieman @properties Christie's International Real Estate

  1380 Westmoor Trail, Winnetka, IL 60093
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  /42

  $1,425,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,163 Sq Ft

  1087 Ash St, Winnetka, IL 60093

  If you are looking for a right-size, upsize, or downsize home that can effortlessly adapt to your changing needs, you've found your dream home. 1087 Ash is pure perfection! There is so much more than meets the eye, as the substantial addition is beautifully tucked behind the original home. Step into the sunny three-season room - perfect for morning coffee or an afternoon mahj game - and sets the

  Leslie Maguire @properties Christie's International Real Estate

  1087 Ash St, Winnetka, IL 60093
• 

  

  /58

  $4,200,000

  • 6 Beds
  • 9 Baths
  • 6,950 Sq Ft

  1128 Mount Pleasant Rd, Winnetka, IL 60093

  Built to impress, this beautifully designed, custom crafted home is discreetly tucked in next to Crow Island Woods you will have nature at your doorstep and be perfectly situated on an amazing half-acre lot. This stunning 5 + bedroom, 6.3 bath home combines timeless architecture with thoughtful modern accents, offering a level of comfortable, elegant living in the North Shore's most sought-after

  Eugene Fu @properties Christie's International Real Estate

  1128 Mount Pleasant Rd, Winnetka, IL 60093
• 

  

  /50

  $4,999,900

  Pending

  • 6 Beds
  • 6 Baths
  • 4,159 Sq Ft

  936 Sunset Rd, Winnetka, IL 60093

  Generational opportunity...the chance of a lifetime now awaits in one of Winnetka's most premier "off lake" enclave neighborhood...936 Sunset Road with two golden options for this exclusive real estate offering. This extraordinary Ralph Lauren vibe, country ranch is all about casual elegance with a desirable first floor primary suite. Set on a magnificent 1.29 acre lot, this property now INCLUDES

  Jena Radnay @properties Christie's International Real Estate

  936 Sunset Rd, Winnetka, IL 60093
• 

  

  /43

  $2,569,900

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

  62 Woodley Rd, Winnetka, IL 60093

  The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as

  Jena Radnay @properties Christie's International Real Estate

  62 Woodley Rd, Winnetka, IL 60093
• 

  

  /14

  $16,900,000

  • 6 Beds
  • 10 Baths
  • 15,000 Sq Ft

  915 Sunset Rd, Winnetka, IL 60093

  A Home That Redefines Scale and Lifestyle. With over 17,000 square feet of meticulously designed living space-including 7,500 square feet dedicated to main-floor living and entertaining-this residence represents one of the most comprehensive lifestyle homes ever built in Winnetka. Designed and built by noted builder, every element was curated for collectors, entertainers, and owners who value

  Mary Maris Village Realty Group Inc

  915 Sunset Rd, Winnetka, IL 60093
• 

  

  /26

  $3,200,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 3,683 Sq Ft

  48 Indian Hill Rd, Winnetka, IL 60093

  Tucked away in one of Winnetka's most coveted private roads, this exceptional 5-bedroom, 4.5-bathroom estate offers a prime spacious lot surrounded by majestic, mature trees. The property boasts an extraordinary setting that guarantees ultimate privacy while maximizing its unique geographic advantage. The home features dramatic, unobstructed vistas overlooking the historic Indian Hill Golf Course

  Joseph Nash @properties Christie's International Real Estate

  48 Indian Hill Rd, Winnetka, IL 60093
• 

  

  /41

  $1,779,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,950 Sq Ft

  639 Lincoln Ave, Winnetka, IL 60093

  Nestled in an exceptional location, this beautifully appointed home offers the perfect combination of charm, comfort, and convenience. Just moments from vibrant downtown Winnetka, you'll enjoy easy access to outstanding restaurants, boutique shopping, the train station, and the beach-making it easy to embrace the very best of the community. Inside, the thoughtfully designed floor plan features

  Anne Malone Engel & Voelkers Chicago North Shore

  639 Lincoln Ave, Winnetka, IL 60093
• 

  

  /48

  $4,699,000

  Pending

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

  231 Woodlawn Ave, Winnetka, IL 60093

  Magnificent East Glencoe home- approximately 9,000 sf of total finished space. 6 BR all ensuite plus 3 additional half baths. Stone & brick exterior on over .5 acre lot. Close to train. Featuring a spectacular kitchen, media room, cherry library, workout room, sauna, wine cellar, and fully fenced expansive private outdoor living space with fireplace / TV and separate fire pit with seating area

  Craig Stone Stone Realty Group

  231 Woodlawn Ave, Winnetka, IL 60093
• 

  

  /35

  $2,899,000

  • 4 Beds
  • 3.5 Baths
  • 3,304 Sq Ft

  792 Walden Rd, Winnetka, IL 60093

  Stunning million dollar+ renovation of a picture perfect brick center-entry Colonial ideally positioned on one of Winnetka's most coveted streets with breathtaking views. Thoughtfully reimagined and meticulously renovated from top to bottom in 2022, this exceptional residence blending timeless architecture with beautifully curated finishes, impeccable craftsmanship, and modern luxury throughout.

  Paige Dooley Compass

  792 Walden Rd, Winnetka, IL 60093
• 

  

  /36

  $2,695,000

  Pending

  • 4 Beds
  • 5 Baths
  • 4,574 Sq Ft

  92 Indian Hill Rd, Winnetka, IL 60093

  This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on a spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large foyer and move

  Kathryn Mangel @properties Christie's International Real Estate

  92 Indian Hill Rd, Winnetka, IL 60093
• 

  

  /25

  $1,700,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,364 Sq Ft

  478 Sunset Rd, Winnetka, IL 60093

  They don't build them like this anymore, but they should! This solidly built custom Hemphill home is ideally located in sought-after East Winnetka and offers timeless character, quality craftsmanship, and thoughtful updates. Built in 1936 with exceptional materials and lovingly maintained by only two owners, this home combines classic elegance with modern comfort. The spacious living room

  Cha McDaniel @properties Christie's International Real Estate

  478 Sunset Rd, Winnetka, IL 60093
• 

  

  /46

  $2,599,900

  • 4 Beds
  • 4.5 Baths
  • 3,610 Sq Ft

  1192 Chatfield Rd, Winnetka, IL 60093

  Incredible architecturally divine jewel box nestled on one of Hubbard Woods' most coveted cul-de-sac streets. Extraordinary vintage details in this distinctive and beautifully scaled Georgian home, where timeless elegance has been thoughtfully enhanced with over $1.2 million in renovations & infrastructure improvements. Step inside and right away feel the elegant original details with original

  Jena Radnay @properties Christie's International Real Estate

  1192 Chatfield Rd, Winnetka, IL 60093
• 

  

  /44

  $1,975,000

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

  922 Ash St, Winnetka, IL 60093

  Exceptional 4-bedroom, 2.1-bath Winnetka home with a huge third-floor loft, ideally located on the coveted Tree Streets and set on a deep 50 x 187 lot. An attached, extra-deep 2-car garage provides direct entry into a convenient mudroom and powder room. A charming covered front porch welcomes you into a home filled with high ceilings, oversized windows, hardwood floors, and incredible natural

  Selma Nemeth @properties Christie's International Real Estate

  922 Ash St, Winnetka, IL 60093
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  /58

  $3,049,000

  • 5 Beds
  • 4.5 Baths
  • 5,212 Sq Ft

  654 Pine St, Winnetka, IL 60093

  Inspired by timeless French Eclectic architecture and impeccably built in 2007, this extraordinary residence offers an exceptional blend of architectural character, refined craftsmanship, and modern luxury. Ideally located just blocks from Lake Michigan, top-rated schools, parks, town, and train, the home sits on a beautifully landscaped lot designed for both elegant entertaining and everyday

  Kelly Lundin Compass

  654 Pine St, Winnetka, IL 60093
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  /38

  $1,699,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 3,639 Sq Ft

  995 Oak St, Winnetka, IL 60093

  Easy, in-town living in this wonderful home! This spacious home is conveniently located in the ideal 'walk to everything' location in the heart of Winnetka - close to absolutely everything. Built in 1995 with all the amenities one needs: classic center entry layout, large welcoming foyer, bright interior with an abundance of natural light, large scaled rooms, eat-in kitchen adjacent to family

  Joanne Hudson Compass

  995 Oak St, Winnetka, IL 60093
• 

  

  /45

  $2,795,000

  • 5 Beds
  • 5.5 Baths
  • 4,089 Sq Ft

  73 Locust Rd, Winnetka, IL 60093

  A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature landscaping. Only one owner since home was completed on this property in 2012. Stately and traditional two story brick

  Beverly Smith @properties Christie's International Real Estate

  73 Locust Rd, Winnetka, IL 60093
• 

  

  /81

  $29,900,000

  • 8 Beds
  • 13 Baths
  • 20,000 Sq Ft

  319 Sheridan Rd, Winnetka, IL 60093

  It's time to unveil the pinnacle of lakefront living in IL, as this newer construction estate is better than brand new construction as it encompasses features that could never be built today with the new lakefront building ordinances. Try to top this...your personal wellness club that is only 20 steps out to your own private, 141-foot wide, sandy beach with indoor pool, sauna, and

  Jena Radnay @properties Christie's International Real Estate

  319 Sheridan Rd, Winnetka, IL 60093
• 

  

  /60

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 3,362 Sq Ft

  1110 Elm St, Winnetka, IL 60093

  Timeless Elegance Meets Modern Luxury with this prime Winnetka home on a large corner lot. Discover the perfect blend of historic character and contemporary living in this meticulously maintained residence. From the moment you step inside, rich vintage craftsmanship takes center stage, highlighted by striking coffered ceilings, multiple cozy fireplaces, and an exquisite built-in buffet. At the

  Brian Grienenberger Baird & Warner

  1110 Elm St, Winnetka, IL 60093
• 

  

  /56

  $4,950,000

  • 5 Beds
  • 7 Baths
  • 9,908 Sq Ft

  32 Woodley Rd, Winnetka, IL 60093

  Nestled down a winding, private road on 1.9 meticulous park-like acres, this grand, almost 10,000 square foot residence exudes luxury and timeless elegance. The front entrance is set apart from the road by a sweeping circular drive bordered by private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal

  Katharine Hackett @properties Christie's International Real Estate

  32 Woodley Rd, Winnetka, IL 60093
• 

  

  /70

  $2,250,000

  • 4 Beds
  • 6 Baths
  • 4,225 Sq Ft

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093

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