Chappaqua, NY Homes

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  /17

  $3,350,000

  • 4 Beds
  • 7 Baths
  • 5,712 Sq Ft

  201 Bedford Rd, Chappaqua, NY 10514

  Exciting all new construction by highly regarded local builder, Tavo Development, along with noted architect Teo Siguenza, aiming for a Fall 2026 completion. This refined, 5,712 sq ft Colonial blends classic architecture with sophisticated modern living. The light-filled main level, with 10’ ceilings, offers a seamless open floorplan featuring a chef’s kitchen with island and service pantry,

  Brian Milton Compass Greater NY, LLC

  201 Bedford Rd, Chappaqua, NY 10514
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  $999,000 Sold Aug 18, 2025

  326 Millwood Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 2,313 Sq Ft
  • Built 1924

  Last Sold Summary

  • $432/SF
  • 3 Days On Market

  Current Estimated Value $1,072,546

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  326 Millwood Rd, Chappaqua, NY 10514
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  Est $2,603,320 Not Listed For Sale

  31 Hemlock Hills, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,187 Sq Ft
  • Built 1989

  31 Hemlock Hills, Chappaqua, NY 10514

  Last Sold Summary

  • 13% Above List Price
  • $371/SF
  • 21 Days On Market

  • Last Sold Price $2,294,000
  • Aug 30, 2024

  Last Listing Agent Judith Kelly Houlihan Lawrence Inc.
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  $1,549,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,956 Sq Ft

  21 Kitchawan Dr, Chappaqua, NY 10514

  Picture-perfect Colonial in one of Chappaqua’s most sought-after neighborhoods, blends timeless 1920s charm with modern comfort and style. Set on over an acre of exquisitely manicured, park-like grounds, this nearly 4,000 sq. ft. home offers 4 bedrooms, 2.5 baths, beautifully scaled rooms, and abundant natural light throughout.Anchoring the home, a magnificent living room welcomes you with a

  Jennifer Harris Compass Greater NY, LLC

  21 Kitchawan Dr, Chappaqua, NY 10514
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  $2,635,000 Sold Aug 25, 2025

  8 Turtleback Way, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 6,649 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Above List Price
  • $396/SF
  • 10 Days On Market

  Current Estimated Value $2,605,201

  Last Listing Agent Michele Iasich-Pagnotta Houlihan & O'Malley R. E. Serv

  8 Turtleback Way, Chappaqua, NY 10514
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  Est $2,878,953 Not Listed For Sale

  6 Hemlock Hollow, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,422 Sq Ft
  • Built 1998

  6 Hemlock Hollow, Chappaqua, NY 10514

  Last Sold Summary

  • 20% Above List Price
  • $374/SF
  • 21 Days On Market

  • Last Sold Price $2,400,000
  • Jun 29, 2023

  Last Listing Agent Sari Shaw Compass Greater NY, LLC
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  $639,000

  • Land
  • 7,405 Sq Ft
  • $3,758,824 per Acre

  65 S Bedford Rd, Chappaqua, NY 10514

  A rare opportunity to build mixed use consisting of commercial/professional and multi-family with huge income potential.The 1st floor as commercial and the 2nd and 3rd floors residential apartments.An architect has drawn 4 concept plans ranging from commercial space and lobby with (4) 2-bedroom apartments to commercial space and lobby with (6) 1-bedroom apartments.One example:1st

  Theodore Weinstein REO Edge LLC

  65 S Bedford Rd, Chappaqua, NY 10514
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  $1,290,000 Sold Jan 21, 2026

  71 Commodore Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $659/SF
  • 37 Days On Market

  Current Estimated Value $1,294,897

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  71 Commodore Rd, Chappaqua, NY 10514
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  Est $3,188,818 Not Listed For Sale

  3 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 6,083 Sq Ft
  • Built 1994

  3 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 12% Above List Price
  • $469/SF
  • 29 Days On Market

  • Last Sold Price $2,850,000
  • Aug 09, 2023

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC
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  $1,290,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,421 Sq Ft

  80 Roaring Brook Rd, Chappaqua, NY 10514

  Step into a home that blends space, light, and everyday convenience in all the right ways. This legal 3-bedroom residence lives like a 4-bedroom, offering flexible options including a potential first-floor bedroom—perfect for guests, work-from-home needs, or multigenerational living.At the heart of the home, a majestic family room with a fireplace creates a warm and inviting atmosphere, ideal

  Mark Okamoto Houlihan Lawrence Inc.

  80 Roaring Brook Rd, Chappaqua, NY 10514
• 

  $1,450,000 Sold May 22, 2025

  2 South Place, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,233 Sq Ft
  • Built 1936

  Last Sold Summary

  • 32% Above List Price
  • $649/SF
  • 9 Days On Market

  Current Estimated Value $1,452,240

  Last Listing Agent Toni DiMichelo Houlihan Lawrence Inc.

  2 South Place, Chappaqua, NY 10514
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  Est $2,775,676 Not Listed For Sale

  6 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 7 Baths
  • 7,624 Sq Ft
  • Built 1994

  6 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 12% Above List Price
  • $325/SF
  • 164 Days On Market

  • Last Sold Price $2,480,000
  • May 10, 2024

  Last Listing Agent Yaxing Zhang Houlihan Lawrence Inc.
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  /29

  $1,499,000

  • 4 Beds
  • 3 Baths
  • 3,002 Sq Ft

  95 Old Lyme Rd, Chappaqua, NY 10514

  Attractive contemporary home ideally located near town, offering over 3,000 square feet of light-filled living space with soaring ceilings and a wonderful open flow for today’s lifestyle. This 4-bedroom home features a spacious cook’s kitchen, three fireplaces, and generously scaled rooms designed for comfortable everyday living and easy entertaining. A flexible first-floor room plus full bath

  Amy Singer Houlihan Lawrence Inc.

  95 Old Lyme Rd, Chappaqua, NY 10514
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  $2,000,000 Sold Feb 09, 2026

  2 Whippoorwill Close, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,022 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Above List Price
  • $662/SF
  • 4 Days On Market

  Current Estimated Value $1,868,139

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  2 Whippoorwill Close, Chappaqua, NY 10514
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  Est $3,124,407 Not Listed For Sale

  6 Paula Place, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 5,272 Sq Ft
  • Built 2005

  6 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 238% Above List Price
  • $175/SF
  • 85 Days On Market

  • Last Sold Price $925,000
  • Dec 11, 2024

  Last Listing Agent Joe Hasselt Joe Hasselt Real Estate
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  $1,299,000

  • 3 Beds
  • 3 Baths
  • 2,444 Sq Ft

  816 Hardscrabble Rd, Chappaqua, NY 10514

  Just north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living—done RIGHT.3 min drive to Metro North station - 48 min ride to Grand Central Station * Set behind a long private driveway with an attached 2-car garage and expansive front yard, the property captures stunning sunset views, with golden hour pouring in the best way. Inside captures a calm, grounded palette

  Bianca Siani eXp Realty

  816 Hardscrabble Rd, Chappaqua, NY 10514
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  $2,300,000 Sold May 29, 2025

  25 Random Farms Dr, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 4,490 Sq Ft
  • Built 1992

  Last Sold Summary

  • 21% Above List Price
  • $512/SF
  • 6 Days On Market

  Current Estimated Value $2,317,108

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  25 Random Farms Dr, Chappaqua, NY 10514
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  Est $826,391 Not Listed For Sale

  15 Paula Place, Chappaqua, NY 10514

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1952

  15 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 17% Above List Price
  • $608/SF
  • 32 Days On Market

  • Last Sold Price $705,000
  • Jun 28, 2024

  Last Listing Agent Lauren Zaccaria Houlihan Lawrence Inc.
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  $1,399,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,443 Sq Ft

  6 Killington St, Chappaqua, NY 10514

  Dreamy modern ranch nestled on a private landscaped acre on a cul-de-sac in sought-after Whippoorwill. A flagstone walkway leads to a covered entry. The contemporary-styled front door with cross-reed glass panels and sidelight sets a refined first impression. Designed for effortless indoor/outdoor living, the rear-facing living room anchors the home with a wood-burning fireplace and two sets of

  Stacy Levey William Raveis-New York, LLC

  6 Killington St, Chappaqua, NY 10514
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  $870,000 Sold Jun 04, 2025

  10 Leroy Place, Chappaqua, NY 10514

  • 2 Beds
  • 1.5 Baths
  • 1,492 Sq Ft
  • Built 1905

  Last Sold Summary

  • 35% Above List Price
  • $583/SF
  • 12 Days On Market

  Current Estimated Value $874,662

  Last Listing Agent Danae Richards William Raveis-New York, LLC

  10 Leroy Place, Chappaqua, NY 10514
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  Est $2,230,139 Not Listed For Sale

  345 Roaring Brook Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 5,668 Sq Ft
  • Built 1965

  345 Roaring Brook Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 16% Above List Price
  • $340/SF
  • 24 Days On Market

  • Last Sold Price $1,925,000
  • Aug 01, 2024

  Last Listing Agent Sena Baron William Raveis-New York, LLC
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  /35

  $1,750,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,712 Sq Ft

  4 Wright Dr, Chappaqua, NY 10514

  A rare opportunity to own one of the few true 3-bedroom townhomes in Chappaqua Crossing Carriages, a sold-out luxury community within the highly sought-after Chappaqua School District. With all three bedrooms ideally situated on the second floor — a layout rarely available here — this exceptional end unit combines smart design with high-end finishes and extensive upgrades throughout. The main

  Karin Kimtis Compass Greater NY, LLC

  4 Wright Dr, Chappaqua, NY 10514
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  $1,720,000 Sold Feb 04, 2026

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Above List Price
  • $530/SF
  • 25 Days On Market

  Current Estimated Value $1,727,388

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
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  Est $2,402,936 Not Listed For Sale

  15 Kerry Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 5,534 Sq Ft
  • Built 1935

  15 Kerry Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 20% Above List Price
  • $361/SF
  • 128 Days On Market

  • Last Sold Price $2,000,000
  • Aug 23, 2024

  Last Listing Agent Janine Marino Houlihan Lawrence Inc.
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  /22

  $1,780,000 Pending

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft

  26 Wallace Way, Chappaqua, NY 10514

  Welcome to 26 Wallace Way — a standout residence in the coveted, sold-out Chappaqua Crossings Carriages community. Thoughtfully designed and impeccably finished, this first-floor primary bedroom home elevates townhouse living with refined interiors, dramatic architecture, and a setting that is both private and connected.The main level makes an immediate impression with a dramatic

  Craig DeCecchis Corcoran Legends Realty

  26 Wallace Way, Chappaqua, NY 10514
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  $1,775,000 Sold Jul 17, 2025

  3 Sunset Dr, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,587 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Above List Price
  • $495/SF
  • 7 Days On Market

  Current Estimated Value $1,819,951

  Last Listing Agent Debra Goldenberg Compass Greater NY, LLC

  3 Sunset Dr, Chappaqua, NY 10514
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  Est $2,030,236 Not Listed For Sale

  28 McKesson Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,541 Sq Ft
  • Built 1967

  28 McKesson Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 6% Above List Price
  • $539/SF
  • 12 Days On Market

  • Last Sold Price $1,909,000
  • Jul 12, 2023

  Last Listing Agent Amanda Acard Nestedge Realty
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  $1,195,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,407 Sq Ft

  86 Seven Bridges Rd, Chappaqua, NY 10514

  Nestled privately back from the street, this stunning residence offers a seamless blend of indoor elegance and outdoor serenity. The heart of the home is an airy, open-concept first floor anchored by a cozy wood-burning fireplace and a renovated chef’s kitchen. This level flows naturally into a bright family room with exposures on three sides. This level also opens through sliders to an expansive

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  86 Seven Bridges Rd, Chappaqua, NY 10514
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  $1,679,000 Sold Sep 18, 2025

  10 Carriage Ln Unit 85, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2025

  Last Sold Summary

  • $514/SF
  • 137 Days On Market

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  10 Carriage Ln Unit 85, Chappaqua, NY 10514
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  Est $1,882,057 Not Listed For Sale

  1 Round Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,164 Sq Ft
  • Built 1963

  1 Round Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 8% Above List Price
  • $553/SF
  • 52 Days On Market

  • Last Sold Price $1,750,000
  • Oct 03, 2024

  Last Listing Agent Elaine Wasserman Houlihan Lawrence Inc.
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  $2,600,000

  • 6 Beds
  • 4 Baths
  • 4,233 Sq Ft

  82 Douglas Rd, Chappaqua, NY 10514

  UNIQUE HIGH-NET INVESTMENT OPPORTUNITY IN CHAPPAQUA SCHOOLS - 5 MIN WALK TO TRAIN. LIVE IN ONE UNIT AND COLLECT INCOME FROM TWO UNITS. LEGAL THREE-FAMILY PROPERTY WITH ONE SINGLE-FAMILY 2BR/2BA RESIDENCE AND A TWO-FAMILY (4BR/2BA) RESIDENCE. HIGH RENTS - $167K ANNUAL GROSS/ $135K NET. ALL UNITS CURRENTLY RENTED BUT TWO OF THREE UNITS EXPIRE 7/31/26, SO THERE IS FLEXIBILITY. SINGLE FAMILY TENANT

  Kristen Renzulli Arch & Gable Realty LLC

  82 Douglas Rd, Chappaqua, NY 10514
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  $1,715,408 Sold May 16, 2025

  3 Dewitt Dr Unit 77, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Above List Price
  • $525/SF
  • 39 Days On Market

  Current Estimated Value $1,754,796

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  3 Dewitt Dr Unit 77, Chappaqua, NY 10514
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  Est $2,062,371 Not Listed For Sale

  2 Sunset Dr, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,474 Sq Ft
  • Built 1986

  2 Sunset Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 17% Above List Price
  • $322/SF
  • 6 Days On Market

  • Last Sold Price $1,760,000
  • Jun 10, 2024

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
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  $1,425,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,761 Sq Ft

  39 Mayberry Rd, Chappaqua, NY 10514

  Set privately on 2+ acres at the end of a quiet cul-de-sac, this beautifully updated 4-bedroom ranch lives like a 5-bedroom home and offers the perfect blend of comfort, flexibility, and style. Enjoy distant western sunset views and direct access to the adjacent Pruyn Sanctuary, creating a serene, nature-connected setting while still being part of a neighborhood.The heart of the home is the

  Sena Baron William Raveis-New York, LLC

  39 Mayberry Rd, Chappaqua, NY 10514
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  $1,402,970 Sold Jun 23, 2025

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Above List Price
  • $476/SF
  • 142 Days On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514
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  Est $1,445,086 Not Listed For Sale

  12 Seven Bridges Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft
  • Built 1950

  12 Seven Bridges Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 2% Above List Price
  • $554/SF
  • 13 Days On Market

  • Last Sold Price $1,410,000
  • Apr 15, 2025

  Last Listing Agent Brendan Preston Houlihan Lawrence Inc.
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  $4,500,000

  • 5 Beds
  • 7 Baths
  • 7,608 Sq Ft

  150 Old Farm Rd N, Chappaqua, NY 10514

  1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  150 Old Farm Rd N, Chappaqua, NY 10514
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  $2,000,000 Sold Apr 28, 2026

  40 Smith St, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,658 Sq Ft
  • Built 1927

  Last Sold Summary

  • 38% Above List Price
  • $752/SF
  • 7 Days On Market

  Current Estimated Value $1,426,028

  Last Listing Agent Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  40 Smith St, Chappaqua, NY 10514
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  Est $1,243,961 Not Listed For Sale

  610 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • Built 1954

  610 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 107% Above List Price
  • $297/SF
  • 2 Days On Market

  • Last Sold Price $600,000
  • Dec 07, 2023

  Last Listing Agent Igor Krasnoperov Rising Star Realty
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  $1,495,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,347 Sq Ft

  52 Whippoorwill Lake Rd, Chappaqua, NY 10514

  Welcome to this fabulous 4-bedroom, 2.5-bath contemporary Colonial home, perfectly designed for today’s lifestyle with a seamless blend of style and comfort. Set on 2.26 private acres with vast views of the private community lake, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. As you enter the home, you step into the formal

  Lisa Teich Julia B Fee Sothebys Int. Rlty

  52 Whippoorwill Lake Rd, Chappaqua, NY 10514

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