Chappaqua, NY Homes

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  /34

  $1,799,000

  • 5 Beds
  • 5.5 Baths
  • 4,616 Sq Ft

  675 Quaker Rd, Chappaqua, NY 10514

  Stunning and elegant 5 bedroom/5.5 baths ranch style home plus detached garage Studio with full Bath and Kitchenette. Set back from the road with a fenced yard. Luxuriously appointed. Custom millwork featured in every room. Open floor plan, living room with marble floors, fireplace surrounded by built-in shelving with adjacent dining room with built-in cabinetry and buffet. Custom kitchen with

  Margaret Harrington Douglas Elliman Real Estate

  675 Quaker Rd, Chappaqua, NY 10514
• Explore Chappaqua

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  /25

  $3,775 - $5,300 per month

  Chappaqua Crossing Apartments

  1 - 2 Beds

  480 Bedford Rd, Chappaqua, NY 10514

  Wilder Balter Partners, Inc., Hudson valley's premier developer of luxury homes has written a new chapter for the iconic reader's digest building. The four-story structure has undergone an unprecedented renovation, and the finished product embraces the nostalgia of the old media empire's headquarters with the extravagance of contemporary housing. Chappaqua Crossing Apts is now open! Please call

  480 Bedford Rd, Chappaqua, NY 10514
• 

  $2,060,000 Sold Dec 05, 2025

  • 4,172 Sq Ft
  • $494/SF
  • 52 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1900

  77 Haights Cross Rd, Chappaqua, NY 10514

  Timeless elegance meets modern comfort in this enchanting 1901 hunting lodge, masterfully restored in 1991 and recently enhanced. Set on beautifully landscaped grounds with lush gardens, this distinguished home features a dramatic front portico, high ceilings, intricate millwork, and unique architectural details throughout. Grand living spaces include a library/home office with French doors and

  Joshua Rogull Julia B Fee Sothebys Int. Rlty

  77 Haights Cross Rd, Chappaqua, NY 10514
• 

  Est $1,214,306 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,995 Sq Ft

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514
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  /26

  $1,999,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,849 Sq Ft

  73 Whippoorwill Lake Rd, Chappaqua, NY 10514

  Experience modern luxury and timeless sophistication in this stunning contemporary, beautifully sited on over an acre of park-like property in Chappaqua’s sought-after Whippoorwill neighborhood. Set on a quiet cul-de-sac with a majestic approach, this home is surrounded by mature trees and lush landscaping, creating a private oasis with level play areas and serene natural views backing to a

  Cindy Glynn Compass Greater NY, LLC

  73 Whippoorwill Lake Rd, Chappaqua, NY 10514
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  /11

  $3,775 per month

  • 1 Bed
  • 1 Bath
  • 963 Sq Ft
  • Apartment for Rent

  480 Bedford Rd Unit 208, Chappaqua, NY 10514

  One bedroom plus den apartment the Chappaqua Crossing Community. Two landscaped interior courtyards. On-site walking trail. Resident superintendent and on-site property management. Outdoor playground area, large gym and separate exercise room, Two laundry rooms, Beautiful club/multi-purpose room, including kitchenette. Elegant reading library with dramatic views. The apartment features Luxury

  Donna Lee Blais Northridge Realty

  480 Bedford Rd Unit 208, Chappaqua, NY 10514
• 

  $3,000,000 Sold Dec 02, 2025

  • 5,285 Sq Ft
  • $568/SF
  • 5 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1965

  3 Round Hill Place, Chappaqua, NY 10514

  Rare opportunity to move right into one of the most beautiful homes in the area! This fully renovated 5BR, 4 full & 2 half bath Colonial sits on 2.46 private acres at the end of a cul-de-sac in one of Chappaqua’s most coveted neighborhoods. Blending timeless charm with modern updates, the home features a chef’s kitchen with high-end appliances, sun-filled living spaces, custom millwork, and an

  Hayes Hopple Julia B Fee Sothebys Int. Rlty

  3 Round Hill Place, Chappaqua, NY 10514
• 

  Est $1,771,921 Not Listed For Sale

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

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514
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  /48

  $1,999,999 Pending

  • 3 Beds
  • 4.5 Baths
  • 3,880 Sq Ft

  19 Stony Hollow, Chappaqua, NY 10514

  Living like a four-bedroom, this gracious and spacious three-bedroom plus bonus room modern Colonial shines from top to bottom from the meticulous maintenance and updates by the original owners. A welcoming, grand two-story entry introduces a large formal living room brightly illuminated by large front- and side-facing windows, recessed lighting and a wood-burning fireplace. French doors add

  Stacy Levey William Raveis-New York, LLC

  19 Stony Hollow, Chappaqua, NY 10514
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  /10

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • 832 Sq Ft
  • Apartment for Rent

  85 Paulding Dr, Chappaqua, NY 10514

  Bright one=bedroom accessory apartment in Chappaqua. Open floor plan gives a spacious feel. Sliding glass door opens to large deck running the length of the unit. Enjoy beautiful vistas in this private setting. Heat, electricity, water, trash and snow removal included in the rent. Driveway parking available for one car. Home is equipped with a generator in case of power outage. No pets allowed.

  Mary Grant Houlihan Lawrence Inc.

  85 Paulding Dr, Chappaqua, NY 10514
• 

  $1,095,000 Sold Dec 02, 2025

  • 1,918 Sq Ft
  • $571/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1935

  124 Seven Bridges Rd, Chappaqua, NY 10514

  AO 9/23/25. Set on 3.25 private acres of lush formal gardens and mature woodlands, this one-of-a-kind Chappaqua residence is a rare architectural treasure. Designed in the 1930s by renowned Westchester architect James Renwick Thomson, the home blends refined sophistication with warm, inviting charm—offering an unparalleled living experience just minutes from the heart of town. From Palladian

  Cindy Glynn Compass Greater NY, LLC

  124 Seven Bridges Rd, Chappaqua, NY 10514
• 

  Est $1,476,102 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,811 Sq Ft

  265 Mill River Rd, Chappaqua, NY 10514

  265 Mill River Rd, Chappaqua, NY 10514
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  /26

  $1,650,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514

  Welcome to this sophisticated 4-bedroom, 3.5-bath contemporary residence, perfectly designed for today’s lifestyle with a seamless blend of modern style and functional comfort. Set on a gracious property, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. At the heart of the home, a beautifully appointed kitchen opens to a

  Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
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  /22

  $2,900 per month

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

  150 N Bedford Rd Unit D1, Chappaqua, NY 10514

  Completely renovated one bedroom end unit with an assigned indoor parking space in Chappaqua Commons - a walk to town, school & train complex in the Chappaqua school district. The unit boasts a wood burning fireplace, radiant flooring in the beautifully renovated bathroom with walk in shower, custom closets, in unit laundry, crown molding, and double pane windows. Enjoy use of a private patio

  Amanda Goldberg William Raveis-New York, LLC

  150 N Bedford Rd Unit D1, Chappaqua, NY 10514
• 

  $805,000 Sold Nov 21, 2025

  • 1,767 Sq Ft
  • $456/SF
  • 105 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  149 King St Unit 4, Chappaqua, NY 10514

  Experience the vibrancy and user-friendly vibe of the Hamlet of Chappaqua in this very special move-in ready, end-unit townhouse, which could be the one you’ve been waiting for. Perfectly located, it is walkable to train, schools, restaurants, shops, farmer’s market, town hall, library and more. It offers generous space with flexibility of use featuring two large bedrooms, plus loft, lower level

  Nancy Jones Julia B Fee Sothebys Int. Rlty

  149 King St Unit 4, Chappaqua, NY 10514
• 

  Est $802,717 Not Listed For Sale

  70 Leroy Rd, Chappaqua, NY 10514

  70 Leroy Rd, Chappaqua, NY 10514
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  /32

  $1,599,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,732 Sq Ft

  35 Whitlaw Ln, Chappaqua, NY 10514

  Timeless elegance meets modern comfort in this beautifully updated Colonial home. Double entry front doors open to a gracious foyer, setting the stage for the home’s expansive and light-filled layout. At its center, the renovated chef’s kitchen impresses with gleaming Caesarstone countertops, professional-grade stainless steel appliances, dual dishwashers, an oversized island with prep sink,

  Jennifer Harris Compass Greater NY, LLC

  35 Whitlaw Ln, Chappaqua, NY 10514
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  /36

  $10,500 per month

  • 5 Beds
  • 5.5 Baths
  • 5,356 Sq Ft
  • House for Rent

  105 Hardscrabble Lake Dr, Chappaqua, NY 10514

  Elegant Estate Rental with Breathtaking Views & Unmatched Entertaining Spaces - Step into sophistication with this exquisite 5-bedroom, 5.5-bath Colonial, gracefully situated on 2.2 acres along a semi-private lane in Chappaqua’s sought-after Hardscrabble Lake neighborhood.From the grand double staircases and soaring two-story foyer to the chef’s kitchen equipped with Viking and Bosch

  Suzanne Sanborn William Raveis Real Estate

  105 Hardscrabble Lake Dr, Chappaqua, NY 10514
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  $700,000 Sold Nov 21, 2025

  • 2,875 Sq Ft
  • $243/SF
  • 96 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2025

  136 Roaring Brook Rd, Chappaqua, NY 10514

  Experience the pinnacle of refined living in this newly reimagined modern farmhouse, perfectly sited on a secluded, tree-lined acre in the heart of Chappaqua. With over 2,800 square feet, this residence blends timeless architectural detail, ready for the buyer’s touch. Andersen 400 series windows and doors throughout, most are six-foot in height, enhance natural light and frame serene woodland

  John Oliveira Douglas Elliman Real Estate

  136 Roaring Brook Rd, Chappaqua, NY 10514
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  Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 3,101 Sq Ft

  39 Lila Ln Unit 59, Chappaqua, NY 10514

  39 Lila Ln Unit 59, Chappaqua, NY 10514
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  /39

  $2,500,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 5,907 Sq Ft

  61 Carolyn Place, Chappaqua, NY 10514

  Located in the coveted Whippoorwill estate area, 61 Carolyn Place presides on 2.19 manicured acres and overlooks the Whippoorwill Country Club’s private golf course. Meticulous details abound with lofty ceilings and spacious rooms, complemented by warm, inviting, intimate spaces and outdoor areas. An open gourmet kitchen and breakfast room flow to the grand two-story family room and dedicated

  Hayes Hopple Julia B Fee Sothebys Int. Rlty

  61 Carolyn Place, Chappaqua, NY 10514
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  /11

  $5,300 per month

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Apartment for Rent

  480 Bedford Rd Unit 210, Chappaqua, NY 10514

  Stunning 2 Bedroom, 2 baths apartment the Chappaqua Crossing Community. Two landscaped interior courtyards. On-site walking trail. Resident superintendent and on-site property management. Outdoor playground area, large gym and separate exercise room, Two laundry rooms, Beautiful club/multi-purpose room, including kitchenette. Elegant reading library with dramatic views. The apartment features

  Donna Lee Blais Northridge Realty

  480 Bedford Rd Unit 210, Chappaqua, NY 10514
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  $2,300,000 Sold Nov 20, 2025

  • 3,960 Sq Ft
  • $581/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1986

  24 North Way, Chappaqua, NY 10514

  A/O-10/13-Move-in ready, light and bright 3 bedroom/ 3.5 bathroom home that can live like a 5 bedroom in the coveted Lawrence Farms South neighborhood with a private, flat backyard with a stone patio, heated gunite pool and a charming pergola. This inviting home with high ceilings throughout, offers a spacious living room with a fireplace, adjacent to a formal dining room, both with glass door

  Pamela Akin Douglas Elliman Real Estate

  24 North Way, Chappaqua, NY 10514
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  Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 3,386 Sq Ft

  35 Lila Ln Unit 57, Chappaqua, NY 10514

  35 Lila Ln Unit 57, Chappaqua, NY 10514
• 

  

  /46

  $1,799,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,543 Sq Ft

  56 Annandale Rd, Chappaqua, NY 10514

  Welcome to 56 Annandale Drive, Chappaqua, a capacious and captivating Cape Cod commandingly set on 1.4 acres in sought-after Lawrence Farms East within walking distance to Mount Kisco Country Club, Kittle House, Chappaqua Crossing, Horace Greeley High School and the town of Mount Kisco. Built for entertaining, every day is a holiday to celebrate in the open, spacious interiors, starting with the

  Stacy Levey William Raveis-New York, LLC

  56 Annandale Rd, Chappaqua, NY 10514
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  /26

  $8,500 per month

  • 4 Beds
  • 3 Baths
  • 3,141 Sq Ft
  • House for Rent

  49 Commodore Rd, Chappaqua, NY 10514

  Picture perfect center hall colonial. Ideal executive rental, walk to town and train. Living room with fireplace, dining room with sliders to large deck, and modern eat-in kitchen. Bedroom and full bath on first level, perfect for au-pair or guest suite. Primary bedroom with en-suite bath, featuring double sink vanity, jacuzzi tub and stand alone shower. Two more hall bedrooms, well-appointed

  Gail Silverstein ERA Insite Realty Services

  49 Commodore Rd, Chappaqua, NY 10514
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  $799,000 Sold Nov 19, 2025

  • 1,420 Sq Ft
  • $563/SF
  • 15 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1941

  37 Hollow Oak Rd, Chappaqua, NY 10514

  Charming and lovingly maintained cape cod home on beautiful private property. Located in the sought after Chappaqua Ridge neighborhood ,this home offers town water, sewer and natural gas, and is minutes to town, train and schools. The first floor features an open kitchen/dining/ living room plus 2 bedrooms and a bath. One of the bedrooms could also be used as a home office. There are sliders out

  Lauren Goldenberg William Raveis Real Estate

  37 Hollow Oak Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 3,101 Sq Ft

  33 Lila Ln Unit 56, Chappaqua, NY 10514

  33 Lila Ln Unit 56, Chappaqua, NY 10514
• 

  

  /36

  $2,499,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,482 Sq Ft

  34 Pebblebrook Way, Chappaqua, NY 10514

  The only triple mint move-in condition house in Chappaqua schools. Nestled within 1.65 acres in the sought-after Hardscrabble Lake development and Chappaqua school district, this rare find modern Center Hall Colonial home epitomizes luxury living. If you are searching for a masterpiece beautifully finished home that is turnkey inside and out, this is your home. This meticulously thought-out

  Natalia Wixom Compass Greater NY, LLC

  34 Pebblebrook Way, Chappaqua, NY 10514
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  /19

  $4,400 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  547 King St Unit B, Chappaqua, NY 10514

  Move right in to this freshly painted home with a beautifully renovated eat-in kitchen and new flooring. High ceilings add to the open feel, offering 2 bedrooms, 1 full bath, plus a versatile den/office. Perfectly located close to town, shops, restaurants, train, bus, and major routes — a blend of comfort and convenience!

  Patricia DelVecchio William Raveis Real Estate

  547 King St Unit B, Chappaqua, NY 10514
• 

  $1,815,000 Sold Nov 10, 2025

  • 3,457 Sq Ft
  • $525/SF
  • 11 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1917

  58 Spring Ln, Chappaqua, NY 10514

  Welcome to 58 Spring Lane – A stunning chalet-style retreat nestled at the end of a private lane just a short walk from the town of Chappaqua and Metro North train. This special home exudes timeless elegance and abundant period charm with its cathedral-vaulted ceilings, original gothic doors, expansive windows and versatile entertaining spaces. The main floor primary suite is a true sanctuary –

  Francie Malina Compass Greater NY, LLC

  58 Spring Ln, Chappaqua, NY 10514
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  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  9 McKesson Hill Rd, Chappaqua, NY 10514

  9 McKesson Hill Rd, Chappaqua, NY 10514
• 

  

  /13

  $599,000

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  150 Bedford Rd Unit 12A, Chappaqua, NY 10514

  Welcome to this move-in-ready 2-bedroom, 2-bath residence in highly sought-after Chappaqua Commons. Recently refreshed with thoughtful updates throughout, this sun-filled home combines modern finishes with effortless convenience.The spacious open-concept living and dining area features brand-new flooring (2025) and a seamless flow to the updated kitchen, boasting new countertops and

  Sari Shaw Compass Greater NY, LLC

  150 Bedford Rd Unit 12A, Chappaqua, NY 10514
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  /21

  $6,250 per month

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft
  • House for Rent

  235 Douglas Rd, Chappaqua, NY 10514

  This beautifully updated rental offers a bright, open layout and a prime location just under a mile from downtown Chappaqua and the Metro North station—perfect for easy commuting and enjoying all the local spots. Freshly painted and move-in ready, the home is available furnished or unfurnished.The main level features a sun-filled living and dining area, an updated kitchen, a spacious

  Danielle Della Pella Compass Greater NY, LLC

  235 Douglas Rd, Chappaqua, NY 10514
• 

  $2,700,000 Sold Nov 04, 2025

  • 5,354 Sq Ft
  • $504/SF
  • 13 Days On Market

  • 4 Beds
  • 6.5 Baths
  • Built 1952

  35 Overlook Dr, Chappaqua, NY 10514

  Welcome to this timeless and sophisticated Colonial, perfectly sited on meticulously landscaped grounds in one of Chappaqua’s most coveted neighborhoods. Just minutes from town, train, and top-rated schools, this exceptional residence seamlessly blends classic architectural charm with modern luxury. This fully renovated and expanded home offers 4 spacious bedrooms (lives like 5), 6.1 beautifully

  Cindy Glynn Compass Greater NY, LLC

  35 Overlook Dr, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 4,692 Sq Ft

  219 Hamilton Rd, Chappaqua, NY 10514

  219 Hamilton Rd, Chappaqua, NY 10514
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  /14

  $1,750,000

  • Land
  • 12.92 Acres
  • $135,449 per Acre

  767 King St, Chappaqua, NY 10514

  Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park,

  Sena Baron William Raveis-New York, LLC

  767 King St, Chappaqua, NY 10514
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  /35

  $5,400 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  25 Maple Ave, Chappaqua, NY 10514

  Charming 3-Bedroom, 2-Bath Home in the Heart of Chappaqua! Welcome to this beautifully updated home located just steps from the train, shops, schools, and restaurants in vibrant downtown Chappaqua. This move-in ready residence features three spacious bedrooms and two full bathrooms, perfect for comfortable family living. Recent upgrades include fresh interior paint, new energy-efficient window,

  Heidi Oliver Houlihan Lawrence Inc.

  25 Maple Ave, Chappaqua, NY 10514
• 

  $799,000 Sold Nov 03, 2025

  • 1,660 Sq Ft
  • $481/SF
  • 76 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  816 Hardscrabble Rd, Chappaqua, NY 10514

  Chappaqua Gem—Welcome to 816 Hardscrabble Road located in a Top-Rated School District! Discover your opportunity to live in the coveted Chappaqua School District with this charming 3-bedroom, 2-bath Split-Level Ranch, nestled on a tranquil half acre lot. This home features a spacious Primary En-Suite, offering comfort and privacy. Recent upgrades include Roof, Liters & Gutters (2022), a brand-new

  Daniel Berger RE/MAX Prestige Properties

  816 Hardscrabble Rd, Chappaqua, NY 10514
• 

  Est $2,528,864 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,249 Sq Ft

  16 Kittle Rd, Chappaqua, NY 10514

  16 Kittle Rd, Chappaqua, NY 10514

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