Newest Homes for Sale in Winnetka, IL

• 

  

  

  /21

  $1,350,000

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  640 Winnetka Mews Unit 403, Winnetka, IL 60093

  Be prepared to be impressed by this rarely available, beautifully updated top-floor 4 bedroom, 3 bath residence in the historic Winnetka Mews, perfectly positioned with a Pine Street exposure. Thoughtfully renovated with exceptional attention to detail, this sun drenched home combines gracious living spaces, timeless finishes and an abundance of thoughtfully designed storage. At the heart of the

  Jenny Fisher @properties Christie's International Real Estate

  640 Winnetka Mews Unit 403, Winnetka, IL 60093
• Explore Winnetka

• 

  

  

  /5

  $1,500,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,895 Sq Ft

  1360 Sunview Ln, Winnetka, IL 60093

  Incredible opportunity to develop, customize, or thoughtfully renovate this traditional four-bedroom home situated on a picturesque half-acre lot backing directly to the Winnetka Golf Club on a quiet, tree-lined street. Whether you're envisioning a stunning custom new construction or transforming the existing residence into your dream home, this exceptional property offers endless possibilities

  Axel Cohen Compass

  1360 Sunview Ln, Winnetka, IL 60093
• 

  

  

  /55

  $1,295,000

  Pending

  • 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
• 

  

  

  /39

  $1,295,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,535 Sq Ft

  600 Sheridan Rd, Winnetka, IL 60093

  Enjoy Lake breezes at this charming home on coveted Sheridan Road in the heart of Winnetka. You won't find a better location - across from the beaches and a short stroll to town! The exterior has a traditional craftsman feel, with a covered front porch, stone accents, lantern-style lights, and a second-floor balcony. Inside, the home is warm and welcoming, with beautiful wood floors flowing

  John Mawicke @properties Christie's International Real Estate

  600 Sheridan Rd, Winnetka, IL 60093
• 

  

  

  /44

  $1,725,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 6,580 Sq Ft

  555 Cherry St, Winnetka, IL 60093

  Beautifully restored idyllic Victorian home expanded for today's living features a flexible floorplan with easy flow, generously sized rooms, dramatic ceiling heights, detailed millwork and plaster moldings, inlaid floors and an abundance of tall oversized windows. The lushly landscaped property highlighted by majestic oak trees is ideally located on a favorite east Winnetka street near lakefront

  Howard Meyers Compass

  555 Cherry St, Winnetka, IL 60093
• 

  

  /31

  $899,000

  • 2 Beds
  • 2 Baths
  • 1,970 Sq Ft

  711 Oak St Unit 308, Winnetka, IL 60093

  Your perfect Winnetka lifestyle awaits! Grab a coffee from Hometown and walk to the beach, library, or jump on the Metra. Don't feel like cooking dinner? Head to one of the many great restaurants right in town. All are just steps away from this East Winnetka Gem. A pleasure to show, this entire condo was thoughtfully & beautifully renovated by Benvenuti and Stein with quality details and finishes

  Kimberly Ann Hoegler @properties Christie's International Real Estate

  711 Oak St Unit 308, Winnetka, IL 60093
• 

  

  /48

  $2,950,000

  Pending

  • 5 Beds
  • 5 Baths
  • 4,212 Sq Ft

  567 Oak St, Winnetka, IL 60093

  The quintessential white-painted Colonial always makes a timeless statement-but set on one of East Winnetka's most spectacular blocks, just steps from town, train, beach and Village Green, it becomes truly exceptional. Welcoming in all the most beautiful ways, this designer showcase house is the one you look forward to coming home to this summer. After hitting the beach, be home in 5 min to get

  Jena Radnay @properties Christie's International Real Estate

  567 Oak St, Winnetka, IL 60093
• 

  

  /65

  $1,425,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,251 Sq Ft

  1062 Ash St, Winnetka, IL 60093

  Beautiful, classic Winnetka home in meticulous condition with gorgeous renovations! The sunny first floor features large rooms that flow perfectly - including a fabulous dining room for entertaining. The renovated kitchen offers exquisite finishes including Italian quartzite counters, custom cabinets and professional appliances, all opening to spacious eating area and family room addition. The

  Joanne Hudson Compass

  1062 Ash St, Winnetka, IL 60093
• 

  

  /46

  $2,499,000

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

  1192 Chatfield Rd, Winnetka, IL 60093

  This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and infrastructure improvements. Step

  Jena Radnay @properties Christie's International Real Estate

  1192 Chatfield Rd, Winnetka, IL 60093
• 

  

  /38

  $3,495,000

  Pending

  • 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
• 

  

  /76

  $3,495,000

  Pending

  • 6 Beds
  • 8 Baths
  • 5,894 Sq Ft

  Unlisted Address

  Set on over half an acre on private Indian Hill Road within the sought-after Greeley School District, this exceptional 6-bedroom, 6.2-bath home offers the perfect blend of timeless elegance and everyday livability. Striking curb appeal sets the tone for the gracious yet highly functional interior. A grand foyer with a dramatic curved staircase introduces beautifully scaled living spaces,

  

  Mary Grant

  @properties Christie's International Real Estate

  Unlisted Address
• 

  

  /41

  $1,795,000

  Pending

  • 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
• 

  

  /27

  $849,900

  $25K PRICE DROP Pending

  • 3 Beds
  • 3 Baths

  444 Oakdale Ave, Glencoe, IL 60022

  Classic brick home filled with timeless character, generous living spaces and thoughtful updates on one of Glencoe's desirable tree-lined streets. A welcoming arched foyer opens to a gracious living room highlighted by refinished hardwood floors, a wood-burning fireplace and a charming office nook. The formal dining room flows seamlessly into a bright enclosed porch overlooking the backyard,

  Peter Moore Baird & Warner

  444 Oakdale Ave, Glencoe, IL 60022
• 

  

  /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
• 

  

  /45

  $1,950,000

  Pending

  • 5 Beds
  • 3 Baths
  • 3,280 Sq Ft

  1440 Tower Rd, Winnetka, IL 60093

  An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and

  Sarah Lyons @properties Christie's International Real Estate

  1440 Tower Rd, Winnetka, IL 60093
• 

  

  /41

  $2,695,000

  • 4 Beds
  • 4.5 Baths
  • 4,509 Sq Ft

  1140 Oakley Ave, Winnetka, IL 60093

  A rare, fully renovated and updated home offering move-in-ready luxury and thoughtful craftsmanship throughout. The primary bath was renovated down to the studs, and now offers a generous shower, private water closet, and all-new fixtures, plumbing, and lighting, plus a huge closet/dressing room with a 7-foot quartz-topped built-in with 24 custom drawers, and floor to ceiling custom built-ins.

  Anne Maitland Jameson Sotheby's International Realty

  1140 Oakley Ave, Winnetka, IL 60093
• 

  

  /45

  $1,395,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,199 Sq Ft

  Unlisted Address

  Storybook Cape Cod in the Heart of Winnetka...Walk to Everything! Picture-perfect curb appeal, timeless character, and an unbeatable in-town location - this home has it all! Thoughtfully expanded and beautifully updated, this home offers the charm buyers love with the space and functionality for today's lifestyle. A welcoming center entrance opens to gracious living spaces designed for both

  Megan Mawicke Jameson Sotheby's International Realty

  Unlisted Address
• 

  

  /35

  $2,899,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 5,102 Sq Ft

  792 Walden Rd, Winnetka, IL 60093

  Stunning million dollar+ renovation of a picture perfect brick center-entry Georgian 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

  Paige Dooley Compass

  792 Walden Rd, Winnetka, IL 60093
• 

  

  /45

  $1,799,000

  Pending

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

  922 Ash St, Winnetka, IL 60093

  Exceptional 4-bedroom, 2.1-bath home on Winnetka's coveted Tree Streets, offering an expansive third-floor loft and situated on a 50' x 187' deep lot. Blending timeless charm with thoughtfully designed living spaces, this home is filled with natural light, soaring ceilings, and beautiful hardwood floors throughout. A welcoming covered front porch leads into gracious living and dining rooms, while

  Selma Nemeth @properties Christie's International Real Estate

  922 Ash St, Winnetka, IL 60093
• 

  

  /8

  $2,595,000

  • Land
  • 1.45 Acres
  • $1,789,655 per Acre

  61 Woodley Rd, Winnetka, IL 60093

  Discover a once-in-a-lifetime opportunity to build your dream estate in one of the North Shore's most coveted neighborhoods. Situated on prestigious Woodley Road in Winnetka, this rarely available 1.45-acre property offers an extraordinary canvas for creating a truly exceptional residence. The existing home has already been demolished, leaving this premier homesite shovel-ready. Bring your own

  Stephen Todd Jameson Sotheby's Intl Realty

  61 Woodley Rd, Winnetka, IL 60093
• 

  

  /58

  $3,049,000

  Pending

  • 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
• 

  

  /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
• 

  

  /43

  $2,795,000

  Open Sat 12PM - 2PM

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

  73 Locust Rd, Winnetka, IL 60093

  Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! 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

  Beverly Smith @properties Christie's International Real Estate

  73 Locust Rd, Winnetka, IL 60093
• 

  

  /53

  $4,949,000

  • 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
• 

  

  /16

  $285,000

  Pending

  • 2 Beds
  • 1 Bath

  1101 Merrill St Unit M1, Winnetka, IL 60093

  Rarely available 2 bed/1 bath condominium in the heart of Hubbard Woods, just steps from the Metra, shops, restaurants, cafes, and Lake Michigan. This beautifully refreshed home features new windows, freshly painted interiors, hardwood floors throughout, an updated bath, and a kitchen with granite countertops and newer stainless steel appliances. A separate dining room offers flexible space for

  Julie Cassin @properties Christie's International Real Estate

  1101 Merrill St Unit M1, Winnetka, IL 60093
• 

  

  /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
• 

  

  /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
• 

  

  /27

  $950,000

  • 4 Beds
  • 1.5 Baths
  • 2,105 Sq Ft

  979 Vine St, Winnetka, IL 60093

  This 4-Bedrm and 2-Bath Cottage style home sits on a 5,267 Sq Ft lot in coveted Winnetka Hubbard Woods. This property located in top -rated schools (Hubbard Elementary) presents potential to renovate, expand or reimagine in a premier North Shore setting. The main floor plan unveils an open concept with a sprawling Family room filled with natural light next to separate sitting room with a gorgeous

  Jacek Piktel Coldwell Banker Realty

  979 Vine St, Winnetka, IL 60093
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /63

  $2,250,000

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

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available first floor primary! 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. Owner extremely

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /31

  $1,195,000

  Pending

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /20

  $16,750,000

  • 7 Beds
  • 8.5 Baths
  • 17,000 Sq Ft

  501 Sheridan Rd, Kenilworth, IL 60043

  New lakefront magnificent transitional home with approximately 17,000 square feet finished space. This house has oversized windows with nonrestricted lake vews and a future private beach.Exterior is constructed of stone 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

  Milena Birov @properties Christie's International Real Estate

  501 Sheridan Rd, Kenilworth, IL 60043

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