Winnetka, IL Homes for Sale

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  /57

  $2,699,000

  $296K 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

  (224) 970-2486

  527 Warwick Rd, Kenilworth, IL 60043
• Explore Winnetka

• 

  

  

  /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

  $300K PRICE DROP

  • 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
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  /72

  $2,250,000

  $1M PRICE DROP

  • 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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  /41

  $3,599,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 5,499 Sq Ft

  Unlisted Address

  Beautifully designed ranch by renowned architect Tony Grunsfeld, perfectly situated on a private street and a spacious half-acre lot. This remarkable 4+bedroom, 4.1-bath home combines timeless architecture with thoughtful modern updates, offering comfortable, elegant living in one of the North Shore's most sought-after locations. The newly updated kitchen is the heart of the home, featuring all

  Jody Dickstein @properties Christie's International Real Estate

  Unlisted Address
• 

  /2

  $2,799,388

  New Construction

  • 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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  /64

  $2,489,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 4,680 Sq Ft

  1241 Ash St, Winnetka, IL 60093

  This extraordinary residence, originally dating to the 1920s and completely rebuilt in 2010-including a fully excavated lower level-offers an exceptional blend of timeless architectural character and refined modern luxury across four impeccably finished levels. Set on an expansive 75 x 187 lot, the stately brick exterior, enhanced by a handsome porte cochere, creates a memorable and elegant

  Joanne Hudson Compass

  1241 Ash St, Winnetka, IL 60093
• 

  

  /31

  $2,995,000

  Pending

  • 5 Beds
  • 6.5 Baths

  4 Indian Hill Rd, Winnetka, IL 60093

  Welcome to this Margaret McCurry designed 5 bedroom, 6 bathroom home with a primary suite on the first floor and golf simulator and extensive lower level recreation area. Tucked off Indian Hill golf course on a special little lane, it's all here in this custom built home w/first floor primary bedroom with a spectacular floor plan and sliding doors that can define the rooms. One of a kind design

  Kathryn Mangel @properties Christie's International Real Estate

  4 Indian Hill Rd, Winnetka, IL 60093
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  /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
• 

  

  /54

  $2,395,000

  Pending

  • 4 Beds
  • 5 Baths

  747 Lincoln Ave, Winnetka, IL 60093

  Classic cedar shake Colonial on an exceptional 100-foot-wide lot in East Winnetka, just moments from the train, schools, beaches and town. Thoughtfully renovated with a fresh coastal aesthetic, this light-filled home beautifully blends timeless architectural detail and old-world craftsmanship with today's airy, modern style. A welcoming foyer opens to a gracious living room with hardwood floors,

  Colleen Archer Daugherty @properties Christie's International Real Estate

  747 Lincoln Ave, Winnetka, IL 60093
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  /58

  $2,439,000

  Pending

  • 4 Beds
  • 7 Baths
  • 4,269 Sq Ft

  1185 Hill Rd, Winnetka, IL 60093

  Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully designed for both everyday living and exceptional entertaining. The home features a sought-after first-floor primary suite plus an additional bedroom with full ensuite bath in that wing of the home. An outstanding chef's kitchen with top-of-the-line appliances, generous workspace, and a spacious breakfast

  Joanne Hudson Compass

  1185 Hill Rd, Winnetka, IL 60093
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  /70

  $2,395,000

  • 5 Beds
  • 5 Baths
  • 5,646 Sq Ft

  500 Maple St, Winnetka, IL 60093

  Exceptional East Winnetka Georgian on serene and lush . 4-acre grounds (96x160) with sweeping views of the Village Green. Architecturally significant and award-winning William Aiken classic restored and preserved to the modern standard, including a 2007 addition. Just a short walk to everything - town, train, beaches, school, and more - with your own private backyard garden oasis, this home

  Paige Dooley Compass

  500 Maple St, Winnetka, IL 60093
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  /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
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  /2

  $2,500,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 5,184 Sq Ft

  355 Linden St, Winnetka, IL 60093

  Meticulously maintained, this exceptional Winnetka home blends timeless charm with modern luxury. The five-bedroom, four-and-a-half-bath residence features thoughtfully curated details throughout and is ideally situated near the lake, train, schools, parks, and downtown.The home offers beautifully appointed interiors.Outdoors, the fully fenced backyard offers a bluestone patio, fire pit, and

  Iris Kohl Compass

  355 Linden St, Winnetka, IL 60093
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  /50

  $2,995,000

  • 6 Beds
  • 4.5 Baths
  • 6,900 Sq Ft

  127 Glenwood Ave, Winnetka, IL 60093

  Solid stone construction, classic architecture, timeless design and refined living come together in perfect harmony in one of the most coveted and convenient locations in Winnetka/ Hubbard Woods with close proximity to town, train and Lake Michigan. Built in 2006 by Adamczyk Fine Homes and Interiors offering three levels of unparalleled craftmanship and quality totaling almost 7000 square feet.

  Marina Carney Compass

  127 Glenwood Ave, Winnetka, IL 60093
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  /48

  $2,245,000

  $50K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,390 Sq Ft

  1159 Chatfield Rd, Winnetka, IL 60093

  Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and

  Jason Rowland Compass

  1159 Chatfield Rd, Winnetka, IL 60093
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  /58

  $2,395,000

  • 6 Beds
  • 5.5 Baths
  • 4,837 Sq Ft

  1482 Edgewood Ln, Winnetka, IL 60093

  Nestled on a charming, quiet, tree-lined street in Winnetka's highly sought-after Hubbard Woods neighborhood, 1482 Edgewood Lane offers the perfect blend of timeless style, modern functionality, and an unbeatable North Shore location-just steps from Nick Corwin Park, and less than a mile to town, train, and schools. Built in 2015, this stunning Nantucket-inspired newer construction home is

  Kathryn Moor Compass

  1482 Edgewood Ln, Winnetka, IL 60093
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  /21

  $7,275,000

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

  43 Indian Hill Rd, Winnetka, IL 60093

  New magnificent transitional home situated on 1 acre picturesque lot with approximately 15,000 square feet finished space. Exterior is constructed of stone and limestone with slate roof which represents timeless construction. The house features 6 bedrooms, 7.1 bath, 4 fireplaces, spectacular Neff kitchen with top-of-the-line appliances including Sub-Zero refrigerators/freezers, luxury Wolf range,

  Milena Birov @properties Christie's International Real Estate

  43 Indian Hill Rd, Winnetka, IL 60093
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  /35

  $925,000

  Open Sun 12PM - 3PM $25K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  979 Vine St, Winnetka, IL 60093

  Nestled just blocks from Winnetka's famed lakefront, this 4-bed/1.5-bath single-family home at 979 Vine St offers approximately 2,100 sq ft of living space, hardwood floors, a spacious kitchen, and thoughtful layout across levels. Located a few blocks to Tower Road Park/ beach - Lake Michigan and Lloyd Park Boat Launch.. Steps to Green Bay Train - for biking, running, and casual strolls. Plus

  Vernon Spence Jason Mitchell Real Estate IL

  979 Vine St, Winnetka, IL 60093
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  /53

  $5,149,000

  $200K PRICE DROP

  • 6 Beds
  • 7 Baths
  • 13,000 Sq Ft

  320 Woodley Rd, Winnetka, IL 60093

  Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof,

  Susan Maman @properties Christie's International Real Estate

  320 Woodley Rd, Winnetka, IL 60093
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  /39

  $1,850,000

  • 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
• 

  

  /35

  $1,450,000

  Pending

  • 5 Beds
  • 3.5 Baths

  841 Prospect Ave, Winnetka, IL 60093

  Coveted East Winnetka location just two blocks from Tower Road Beach! This charming 5-bedroom, 3.1-bath home offers timeless character and wonderful living space, complete with an inviting front porch. The living room showcases a coffered ceiling, oversized wood-burning fireplace, and beautiful period millwork. A bright sunroom with built-in bookcases provides the perfect retreat. Hardwood floors

  Christie Ascione @properties Christie's International Real Estate

  841 Prospect Ave, Winnetka, IL 60093
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  /55

  $1,495,000

  Pending

  • 4 Beds
  • 4 Baths

  Unlisted Address

  Reimagined, refreshed, and beautifully renovated, this 4-bedroom plus office, 2 full and 2 half bath home is ideally situated in a prime East Winnetka location-just moments from Greeley, New Trier, the Indian Hill Metra stop, beaches, and parks. A thoughtfully designed main level offers a seamless flow between formal and informal living spaces. The inviting living room is anchored by a gas

  Emily Smart LeMire Compass

  Unlisted Address
• 

  

  /20

  $300,000

  Pending

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft

  555 Hill Terrace Unit 307, Winnetka, IL 60093

  Welcome to the charming chimneys. Quiet and secluded. Pretty and bright top floor unit looking out on quaint, treelined courtyard. A large living room greets you with abundant natural light and a charming, wood burning fireplace. Separate, updated white kitchen with shaker style cabinets and granite countertops. Appliances include a double oven, gas stove, dishwasher and refrigerator/freezer.

  Celia Nelson @properties Christie's International Real Estate

  555 Hill Terrace Unit 307, Winnetka, IL 60093
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  /18

  $5,975,000

  New Construction Pending

  • 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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  /26

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft

  680 Green Bay Rd Unit 306, Winnetka, IL 60093

  Classic Gold Coast boutique building energy-but reimagined for Winnetka living, with western sunset views, a beautifully renovated interior, and that rare walk-to-everything lifestyle buyers chase for years. Tucked inside an intimate boutique building in one of Winnetka's most coveted locations, this stunning residence lives like the perfect blend of sophistication, comfort, and effortless

  Connie Dornan @properties Christie's International Real Estate

  680 Green Bay Rd Unit 306, Winnetka, IL 60093
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  /42

  $1,739,000

  Pending

  • 5 Beds
  • 5 Baths
  • 3,162 Sq Ft

  838 Lincoln Ave, Winnetka, IL 60093

  Welcome home to this beautiful east Winnetka home, where classic charm meets modern comfort and the design, ceiling heights, flow and quality is is exceptional. A gracious foyer (15 x 13) welcomes you and flows effortlessly into the inviting living room with gas fireplace and to the formal dining room - complete with a cozy window seat and timeless built-ins - the perfect setting for holiday

  Joanne Hudson Compass

  838 Lincoln Ave, Winnetka, IL 60093
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  /47

  $1,700,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 3,347 Sq Ft

  1368 Scott Ave, Winnetka, IL 60093

  Spacious 5 bedroom 4 1/2 bath Dutch Colonial in desirable Hubbard Woods, ideally situated in a wonderful neighborhood just moments from Hubbard Woods School, the Metra train, downtown shops, restaurants and scenic forest preserve trails for biking, running, kayaking and fishing. The first floor offers loads of natural light, with welcoming living and dining areas plus a dedicated office. The

  Alan Meyerowitz @properties Christie's International Real Estate

  1368 Scott Ave, Winnetka, IL 60093
• 

  

  /78

  $4,500,000

  Pending

  • 6 Beds
  • 7 Baths
  • 6,212 Sq Ft

  140 Birch St, Winnetka, IL 60093

  Set behind mature landscaping on a breathtaking and rarely available full acre, this extraordinary Winnetka residence offers the kind of space, privacy, and walk-to-everything convenience that almost never coexist. Thoughtfully reimagined through a complete gut renovation and expansion in 2010-including a new lower level, this 6-bedroom, 5.2-bath home lives beautifully for today while honoring

  Julie Miller Compass

  140 Birch St, Winnetka, IL 60093
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  /26

  $1,439,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 3,465 Sq Ft

  373 Sunset Rd, Winnetka, IL 60093

  Welcome to 373 Sunset Road, an spacious 5-bedroom, 3.1-bath brick and frame home in sought-after East Winnetka. Ideally located near Greeley Elementary, New Trier High School, the Indian Hill Metra, and just moments from Lake Michigan beaches, this home offers a wonderful blend of classic architecture and exceptional space. The gracious floor plan features a welcoming foyer, office/music room,

  Joanne Hudson Compass

  373 Sunset Rd, Winnetka, IL 60093
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  /37

  $1,299,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,316 Sq Ft

  1295 Sunview Ln, Winnetka, IL 60093

  Exciting chance to refashion this light-filled ranch home to your personal vision. Large windows throughout the home offer beautiful views and light. The spacious kitchen opens to the vaulted family room. The master bedroom and second bedroom are on the first floor, plus two full baths, family room, living room, dining room, and screened porch. Outdoors, there is an expansive stone patio and pond

  Margaret Goss @properties Christie's International Real Estate

  1295 Sunview Ln, Winnetka, IL 60093
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  /43

  $4,500,000

  • 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
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  /54

  $1,885,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,932 Sq Ft

  1082 Ash St, Winnetka, IL 60093

  Picture perfect 4 bed, 3.1 bath colonial farmhouse set on a deep (50 X 178) lot in the coveted "tree streets" of Winnetka. (prime location - walking to preschool thru 8th grade) Lovingly renovated and maintained, 1082 Ash offers an artful blend of charm, modern amenities, and the finest of finishes. This home boasts gracious rooms, timeless architectural details, and exceptional millwork

  Sara Sullivan Compass

  1082 Ash St, 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
• 

  

  /3

  $1,290,000

  • Land
  • 1.36 Acres
  • $948,529 per Acre

  2033 Winnetka Rd, Winnetka, IL 60093

  Reduced new price for the land is more than $100,000 less than the original !! Rare chance to own 1.36 acres of land on beautiful Winnetka rd will provide you endless possibilities to build your dream home. Incredible opportunity to collaborate with experienced luxury builder or bring your own builder. Winnetka High School District. Amazing location- close to Northfield Park District,Westfield

  Natalya Gorodetsky Core Realty & Investments, Inc

  2033 Winnetka 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
• 

  

  /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
• 

  

  /31

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 2,680 Sq Ft

  1208 Oak St, Winnetka, IL 60093

  Nestled in the heart of Winnetka's coveted " TREE STREETS" neighborhood sits the storybook home you've been waiting for. This special home is a sun-filled Mediterranean villa with an effortless blend of timeless architecture and a fresh, coastal-inspired aesthetic throughout. The home showcases airy interiors, soft neutral tones, and a well appointed floor plan that perfectly suits today's

  Alyson Tesar @properties Christie's International Real Estate

  1208 Oak St, Winnetka, IL 60093
• 

  

  /37

  $1,389,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft

  972 Elm St, Winnetka, IL 60093

  Bright, spacious, and beautifully maintained, this charming home offers timeless character, gracious proportions, and an exceptional in-town location on a lush, deep lot with a gorgeous patio with thoughtfully designed seating wall - perfect for entertaining and outdoor enjoyment. High ceilings, classic architectural details, and abundant natural light create a warm and inviting atmosphere

  Joanne Hudson Compass

  972 Elm St, Winnetka, IL 60093
• 

  

  /24

  $899,000

  Pending

  • 3 Beds
  • 2.5 Baths

  574 Orchard Ln, Winnetka, IL 60093

  Perfectly situated in a prime East Winnetka location, this charming home offers an exceptional opportunity to enjoy one of the North Shore's most sought-after neighborhoods at an approachable price point. Just blocks from the lake, town, Metra, Greeley Elementary, and New Trier High School, the lifestyle and convenience are unmatched. Thoughtfully updated over time, the home features bright,

  Danielle Wylie Baird & Warner

  574 Orchard Ln, Winnetka, IL 60093

Showing Results 1 - 40, Page 1 of 2