Winnetka, IL Homes

• 

  

  

  /39

  $2,499,000 Pending

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

  526 Sunset Rd, Winnetka, IL 60093

  Stunning 6-Bed, 5.5-Bath Classic Brick Georgian with Modern Elegance. Step into timeless sophistication with this newer-construction classic brick Georgian, where traditional charm meets contemporary luxury. Designed for both everyday living and grand entertaining, this home boasts an open floor plan that seamlessly blends style and function. Inside, you'll find wide plank hardwood floors and

  Colleen Archer Daugherty @properties Christie's International Real Estate

  526 Sunset Rd, Winnetka, IL 60093
• 

  

  

  /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
• 

  

  

  /44

  $4,500,000 Sold Apr 18, 2025

  • 9,744 Sq Ft
  • $462/SF
  • 45 Days On Market

  • 7 Beds
  • 9 Baths
  • Built 1927

  35 Indian Hill Rd, Winnetka, IL 60093

  REIMAGINED LUXURY - Immerse yourself in the exquisite transformation of an English manor estate nestled on a private lane within one mile of Winnetka's town center. 35 Indian Hill has over ONE & ONE HALF MILLION DOLLARS in improvements both interior and exterior (see upgrades under ADD'L INFO) in the past 10 months! Infrastructure improvements include: POOL, HARDSCAPE, BLUESTONE GARDEN HARDSCAPE,

  Nancy Nugent Jameson Sotheby's Intl Realty

  35 Indian Hill Rd, Winnetka, IL 60093
• 

  

  

  /66

  Est $4,124,924 Not Listed For Sale

  • 4 Beds
  • 9 Baths
  • 11,847 Sq Ft

  106 Longmeadow Rd, Winnetka, IL 60093

  106 Longmeadow Rd, Winnetka, IL 60093
• 

  

  

  /37

  $2,699,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,536 Sq Ft

  822 Bryant Ave, Winnetka, IL 60093

  One of Winnetka's most extraordinary retreats in the most desired walk to location reminiscent of the iconic homes of the era with a stylized full house renovation and addition in 2004. This "better than new" meticulous lovingly restored Historical Home that blends all of life's comforts from the dreamlike screened porches over 1/2 acre of breathtaking grounds and spectacular kitchen//family room

  Paige Dooley Compass

  822 Bryant Ave, Winnetka, IL 60093
• 

  

  /11

  $265,000 Sold Apr 15, 2025

  • 1,030 Sq Ft
  • $257/SF
  • 2 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1971

  134 Green Bay Rd Unit 309, Winnetka, IL 60093

  Move in ready 1 bedroom, 1 bath condo in sought after boutique Winnetka building. Sun-filled condo with open floor plan. White kitchen with breakfast bar, roomy bedroom, updated bath and walk in closet. Loads of storage space. Indoor parking spot. Well decorated lobby and common room with kitchen, exercise area and outdoor pool. Steps to the Metra, Lake Michigan and shopping.

  Mary Grant @properties Christie's International Real Estate

  134 Green Bay Rd Unit 309, Winnetka, IL 60093
• 

  

  /28

  Est $1,812,568 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,570 Sq Ft

  278 Mary St, Winnetka, IL 60093

  278 Mary St, Winnetka, IL 60093
• 

  

  /59

  $2,739,900 Pending

  • 7 Beds
  • 6 Baths
  • 6,102 Sq Ft

  332 Elder Ln, Winnetka, IL 60093

  Gracious, grand and set less than a half of block off Lake Michigan, prepare to fall in love with this very special, solidly built East Winnetka generational home. Only the 4th owner, this approx. 6,000 square ft. of finished space over 3 floors lives large & shines bright with that desired south facing orientation. Brought to a new level of today's comfort with a fabulous addition of a Benvenuti

  Jena Radnay @properties Christie's International Real Estate

  332 Elder Ln, Winnetka, IL 60093
• 

  

  /48

  $2,050,000 Sold Apr 15, 2025

  • 4,147 Sq Ft
  • $494/SF

  • 4 Beds
  • 4.5 Baths
  • Built 2009

  484 Hawthorn Ln, Winnetka, IL 60093

  Welcome to this stunning 6-bedroom, 4.5-bathroom home in pristine condition. The owners have meticulously maintained the property over the years and recently completed a comprehensive refresh, including fresh paint, new lighting, a new flat roof, refinished floors, and detailed inspections of all mechanical systems. The home will be delivered in truly turnkey condition, ready for its next owner.

  Nathan Freeborn Redfin Corporation

  484 Hawthorn Ln, Winnetka, IL 60093
• 

  

  /41

  Est $1,988,639 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
• 

  

  /39

  $1,895,000

  • 4 Beds
  • 8 Baths
  • 3,600 Sq Ft

  1522 Edgewood Ln, Winnetka, IL 60093

  STUNNING HOME REBUILT IN 2024-25 ACROSS FROM NICK CORWIN PARK - UNBELIEVABLE FINISHES IN THIS STATELY BRICK AND LIMESTONE HOME IN HUBBARD WOODS. NOTE THE 2C GARAGE IS DETACHED. LIVE ACROSS FROM THE PARK, PLAYGROUND & SOCCER FIELDS. EXQUISITE DETAILS INCLUDE HANDSOME MILLWORK, TALL CEILINGS, 4 FIREPLACES, SO MUCH NEW! NEW KITCHEN, APPLIANCES, GRANITE AND STONE SURFACES, PREP ISLAND WITH

  Robin Wilson @properties Christie's International Real Estate

  1522 Edgewood Ln, Winnetka, IL 60093
• 

  

  /46

  $930,000 Sold Apr 14, 2025

  • 1,676 Sq Ft
  • $555/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1921

  214 Poplar St, Winnetka, IL 60093

  Storybook charm in East Winnetka! Prepare to be delighted by this darling home brimming with character and charm. Step inside and enjoy the sun-filled space, complete with hardwood floors throughout, arched doorways and custom built-ins. The front living room includes a beautiful wood-burning fireplace and dining area with easy access to the kitchen, featuring high-end stainless steel-appliances.

  Jeffrey Lowe Compass

  214 Poplar St, Winnetka, IL 60093
• 

  

  /30

  Est $2,011,665 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
• 

  

  /35

  $1,650,000 Open Sun 12PM - 2PM

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

  1149 Scott Ave, Winnetka, IL 60093

  Situated on one third of an acre of beautifully landscaped grounds just steps from town, train, parks, and top-rated schools, this classic Winnetka home offers the ideal combination of convenience, charm, and unbelievable indoor and outdoor spaces. The sun-filled main level offers a functional and elegant layout with beautiful hardwood floors throughout. A spacious living room with a cozy wood

  Danielle Wylie Baird & Warner

  1149 Scott Ave, Winnetka, IL 60093
• 

  /2

  $2,600,000 Sold Apr 09, 2025

  • 4,870 Sq Ft
  • $534/SF
  • 4 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1920

  1172 Hamptondale Ave, Winnetka, IL 60093

  This classic Winnetka residence blends timeless architectural details with thoughtful updates, offering comfort and effortless livability. A striking staircase makes a grand impression in the gracious, light-filled two story foyer, setting the tone for the home. Beyond the foyer, the spacious and inviting interior creates a warm atmosphere. Whether gathered in the formal living room or sharing a

  Howard Meyers Compass

  1172 Hamptondale Ave, Winnetka, IL 60093
• 

  

  /29

  Est $922,288 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
• 

  

  /35

  $1,299,000

  • 4 Beds
  • 3.5 Baths
  • 2,511 Sq Ft

  989 Ash St, Winnetka, IL 60093

  Showings begin Friday, May 2nd. Discover an exceptional 5-bedroom, 3.1-bath Colonial located in a prime area. Step onto the newly installed bluestone walkway, leading to an inviting foyer with a formal dining room and a living room featuring floor-to-ceiling windows. The kitchen is thoughtfully designed with a sitting counter, stainless steel Bosch appliances, and a planning desk. Adjacent is a

  John Phillips Compass

  989 Ash St, Winnetka, IL 60093
• 

  /2

  $2,200,000 Sold Apr 07, 2025

  • 4,381 Sq Ft
  • $502/SF
  • 5 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1997

  529 Elder Ln, Winnetka, IL 60093

  Step into sophistication with this beautifully updated East Winnetka home, where timeless elegance meets modern comfort. Every detail has been thoughtfully enhanced, from the striking entryway to the impeccable finishes throughout. The first-floor layout is designed for both versatility and style. Entertain effortlessly in the oversized formal dining room, work in the sun-drenched home office,

  Jenifer McCartney Jameson Sotheby's International Realty

  529 Elder Ln, Winnetka, IL 60093
• 

  

  /45

  Est $2,200,785 Not Listed For Sale

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

  989 Old Green Bay Rd, Winnetka, IL 60093

  989 Old Green Bay Rd, Winnetka, IL 60093
• 

  

  /25

  $1,150,000

  • 2 Beds
  • 2 Baths

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

  Coveted Hedge Row Penthouse, HARD TO FIND ONE FLOOR living in the Heart of Winnetka! These are rarely and this is the first time this condo has ever been on the market. 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

  Megan Mawicke @properties Christie's International Real Estate

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

  

  /24

  $1,417,000 Sold Apr 04, 2025

  • 2,637 Sq Ft
  • $537/SF
  • 0 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1955

  800 Tower Rd, Winnetka, IL 60093

  Welcome to this cozy Cape Cod situated right off Tower and Sheridan Rd. Just steps away from the beach, this home exudes warmth and timeless appeal. The prime East Winnetka location captures the essence of North Shore living. The living/dinning room combo with a fireplace opens up to a grand family room with custom mahogany build-ins. This welcoming space, surrounded by a plethora of natural

  Chris Hristov Real People Realty

  800 Tower Rd, Winnetka, IL 60093
• 

  

  /16

  Est $577,550 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  680 Green Bay Rd Unit 201, Winnetka, IL 60093

  680 Green Bay Rd Unit 201, Winnetka, IL 60093
• 

  

  /34

  $115,000

  • 4 Beds
  • 2 Baths

  99 S Branch Rd, Winnetka, IL 60093

  Beautiful 4 bedroom 2 bath mobile home, located within the Glenview school district! This beautifully maintained home welcomes you with a cozy family room & open-concept kitchen, stainless steel appliances, smart refrigerator, beautiful wood cabinetry & large island, perfect for hosting family and friends! The primary suite has a walk-in closet & refreshed full bath. Newer luxury vinyl tile

  Jennifer Comeaux Redfin Corporation

  99 S Branch Rd, Winnetka, IL 60093
• 

  

  /41

  $1,725,000 Sold Apr 03, 2025

  • 3,560 Sq Ft
  • $485/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1954

  312 Rosewood Ave, Winnetka, IL 60093

  OFFERS DUE by 10:00 AM on Monday, 2/10. Welcome to 312 Rosewood Avenue, a stunningly beautiful 4-bedroom, 3.1 bath home on one of Winnetka's most beloved blocks. This home is truly a dream--with spacious rooms, abundant natural light, and an open circular floor plan designed for effortless living and elegant entertaining. Hardwood floors extend throughout the first and second floors (including

  Susan Sullivan @properties Christie's International Real Estate

  312 Rosewood Ave, Winnetka, IL 60093
• 

  

  /39

  Est $1,901,889 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,029 Sq Ft

  377 Provident Ave, Winnetka, IL 60093

  377 Provident Ave, Winnetka, IL 60093
• 

  

  /72

  $9,499,900 Open Sun 12PM - 2PM

  • 5 Beds
  • 8 Baths
  • 9,723 Sq Ft

  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
• 

  

  /36

  $975,000 Sold Apr 02, 2025

  • 1,700 Sq Ft
  • $574/SF
  • 10 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1914

  1066 Tower Rd, Winnetka, IL 60093

  Experience the renovated charm of this delightful 3 bedroom, 2.2 bathroom home nestled in the heart of Hubbard Woods. The bright, updated kitchen with fabulous southern exposures, complete with an adjacent dining area, offers sunny views of the lush backyard. This fabulous kitchen flows seamlessly into the family room, which features a cozy fireplace and also connects to the first-floor office

  Joanne Hudson Compass

  1066 Tower Rd, Winnetka, IL 60093
• 

  

  /6

  Est $1,019,498 Not Listed For Sale

  • 4 Beds

  1580 Tower Rd, Winnetka, IL 60093

  1580 Tower Rd, Winnetka, IL 60093
• 

  

  /36

  $599,999

  • 2 Beds
  • 3.5 Baths
  • 1,364 Sq Ft

  97 High St, Winnetka, IL 60093

  A rare opportunity has arisen to acquire a 2-bedroom, 3.5-bathroom end unit townhouse in the esteemed neighborhood of Winnetka, conveniently located near Indian Hill Club, Joseph Sears school district, New Trier Township High School, The Kenilworth Beach, Indian Hill Metra Station Zone C, and more. This charming end-unit townhouse boasts all wood floors, a wood burning fireplace in the living

  Lilia Balan Pavlova Properties

  97 High St, Winnetka, IL 60093
• 

  

  /21

  $575,000 Sold Mar 31, 2025

  • 1,500 Sq Ft
  • $383/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1956

  606 Lincoln Ave Unit 606, Winnetka, IL 60093

  Discover this rarely available, updated end-unit townhouse in the serene Lincoln Gardens of East Winnetka. Situated in a private courtyard, this home gives city living vibes with suburban benefits, conveniently located near Lake Michigan beaches, Metra, dining, and shopping. Spread across three floors, it boasts abundant natural light. The updated kitchen features subway tiled backsplash, newer

  Sara Sullivan Compass

  606 Lincoln Ave Unit 606, Winnetka, IL 60093
• 

  

  /32

  Est $5,360,949 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,368 Sq Ft

  473 Sheridan Rd, Winnetka, IL 60093

  473 Sheridan Rd, Winnetka, IL 60093
• 

  

  /101

  $5,995,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 8 Baths
  • 13,482 Sq Ft

  624 Pine Ln, Winnetka, IL 60093

  Welcome to this stunning custom home designed by Morgante Wilson, with thoughtful input from discerning owners. This once in a lifetime home is nestled on a picturesque 0.86-acre lot on private Pine Lane near schools, town and train. This thoughtfully designed home is perfect for all ages, blending creativity and style throughout. The inviting entrance hall sets the tone as you walk in, leading

  Joanne Hudson Compass

  624 Pine Ln, Winnetka, IL 60093
• 

  

  /49

  $1,900,000 Sold Mar 31, 2025

  • 6,554 Sq Ft
  • $290/SF
  • 85 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1985

  1344 Edgewood Ln, Winnetka, IL 60093

  MUCH BIGGER THAN IT LOOKS - Nestled in a private cul-de-sac, this beautifully renovated Cape Cod home offers a perfect blend of classic architecture and modern amenities, ideally located to enjoy all that Winnetka has to offer. The first floor, spanning over 2400 sq ft, boasts an open and airy layout. The expansive kitchen features custom cabinetry, an enormous island with seating, and high-end

  John Mawicke @properties Christie's International Real Estate

  1344 Edgewood Ln, Winnetka, IL 60093
• 

  

  /26

  Est $716,035 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  711 Oak St Unit 109, Winnetka, IL 60093

  711 Oak St Unit 109, Winnetka, IL 60093
• 

  

  /76

  $9,999,500

  • 5 Beds
  • 6.5 Baths
  • 13,171 Sq Ft

  140 Sheridan Rd, Winnetka, IL 60093

  This is the North Shore's most regal restoration to ever come on the market with a captivating, majestic presence set on a rare 1 plus-acre lot that also includes a buildable lot for a 2nd structure to create the ultimate East Winnetka estate. This is a generational opportunity to own an architecturally divine Mayo & Mayo Revival Tudor with intricate details and a thoughtful design that balances

  Jena Radnay @properties Christie's International Real Estate

  140 Sheridan Rd, Winnetka, IL 60093
• 

  

  /38

  $1,675,000 Sold Mar 28, 2025

  • 3,200 Sq Ft
  • $523/SF
  • 2 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1930

  429 Walnut St, Winnetka, IL 60093

  Welcome to 429 Walnut, in the picturesque East Winnetka neighborhood. This charming English-style residence has remarkable architectural features, including graceful archways, an elegant staircase, and hardwood floors. The home seamlessly blends classic design with modern updates, featuring a Benvenuti & Stein kitchen and a sunlit family room. The stunning living room, with its charming

  Katie Hauser Compass

  429 Walnut St, Winnetka, IL 60093
• 

  

  /66

  Est $3,115,213 Not Listed For Sale

  • 6 Beds
  • 8.5 Baths
  • 6,298 Sq Ft

  270 Birch St, Winnetka, IL 60093

  270 Birch St, Winnetka, IL 60093
• 

  

  /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
• 

  

  /91

  $4,495,000 Sold Mar 28, 2025

  • 5,709 Sq Ft
  • $787/SF

  • 5 Beds
  • 8 Baths
  • Built 1975

  89 Indian Hill Rd, Winnetka, IL 60093

  Welcome to 89 Indian Hill Road, a beautifully renovated estate home along the historic Indian Hill Country Club. This property includes 5 bedrooms, 5.2 baths, and a rare, newer two-story guest house! This property presents a unique opportunity, combining the timeless elegance of classic Georgian architecture with sleek modern sophistication. Every detail of this home has been thoughtfully

  Frank Capitanini Compass

  89 Indian Hill Rd, Winnetka, IL 60093
• 

  

  /22

  Est $1,432,765 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,711 Sq Ft

  1028 Cherry St, Winnetka, IL 60093

  1028 Cherry St, Winnetka, IL 60093

Showing Results 41 - 80, Page 2 of 18