Westchester, NY Homes

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  /38

  $1,175,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,728 Sq Ft

  57 Hamilton Dr, Chappaqua, NY 10514

  Welcome to a sleek contemporary home that seamlessly blends indoor comfort with an exceptional outdoor retreat. From the moment you enter, you'll appreciate the design's focus on chic, easy living, bathed in natural light and showcasing exposed beams, custom built-ins, and premium appointments. This home boasts an open concept and has been fully updated, living generously like a 4 or 5-bedroom

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 862-7931

  57 Hamilton Dr, Chappaqua, NY 10514
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  Explore Chappaqua

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  /25

  $2,400 - $6,850 per month

  Chappaqua Crossing Apartments

  1 - 3 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
• 

  $1,615,000 Sold Aug 01, 2025

  • 4,099 Sq Ft
  • $394/SF
  • 13 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1985

  7 High Point Cir, Chappaqua, NY 10514

  Beautifully positioned at the end of a quiet cul-de-sac, this contemporary home offers style and serenity in a prime Chappaqua location. Designed with today’s lifestyle in mind, the open and airy floor plan features soaring ceilings, floor-to-ceiling windows, and sun-drenched spaces throughout. A beautifully updated modern kitchen flows seamlessly into expansive living and dining areas, ideal for

  Cindy Glynn Compass Greater NY, LLC

  7 High Point Cir, Chappaqua, NY 10514
• 

  Est $1,518,252 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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  /49

  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 4,172 Sq Ft

  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
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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
• 

  $600,000 Sold Aug 01, 2025

  • 1,608 Sq Ft
  • $373/SF
  • 28 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  324 N Greeley Ave, Chappaqua, NY 10514

  Welcome to this beautifully renovated home in highly sought after Chestnut Oaks, steps from downtown Chappaqua. A rare opportunity to buy this end unit townhouse in the award-winning Chappaqua school district. This bright and spacious two-bedroom townhouse features a loft, its own washer/drier and balcony. Enjoy stress free living with low maintenance and taxes, close to town with a pool and

  Nick Rie K. Fortuna Realty, Inc.

  324 N Greeley Ave, Chappaqua, NY 10514
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  Est $1,540,440 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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  /44

  $1,774,000

  • 3 Beds
  • 3.5 Baths
  • 3,614 Sq Ft

  21 Wallace Way, Chappaqua, NY 10514

  Better than new at Chappaqua Crossings Carriages! Be among the first to experience this spectacular new community featuring a delightful and charming village atmosphere in the heart of Westchester, Chappaqua, NY. This stunning “Byram Newhaven model” situated in a prime location within the community, offers great curb appeal with its expansive front porch, stone walls and specimen plantings; and

  Ken Wile Redfin Real Estate

  21 Wallace Way, Chappaqua, NY 10514
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  /35

  $6,200 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

  Heidi Oliver Houlihan Lawrence Inc.

  25 Maple Ave, Chappaqua, NY 10514
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  $1,800,000 Sold Aug 01, 2025

  • 4,930 Sq Ft
  • $365/SF
  • 38 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1998

  101 Hardscrabble Lake Dr, Chappaqua, NY 10514

  Welcome to this spacious 5 Bedrm Colonial on 1.5+ acres in the sought-after Hardscrabble Lake neighborhood. Step inside and you will be delighted throughout -- by the sweeping double staircase, beautiful light Oak flooring, freshly painted interior and so much more. The formal Dining Room and Living Room/Office are graciously-sized, perfect for entertaining. At the heart of the home is an

  Victoria Miller Compass Greater NY, LLC

  101 Hardscrabble Lake Dr, Chappaqua, NY 10514
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  Not Listed For Sale

  • 4 Beds

  767 King St, Chappaqua, NY 10514

  767 King St, Chappaqua, NY 10514
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  /9

  $1,807,995 Pending

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

  2 Carriage Ln Unit 81, Chappaqua, NY 10514

  HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner

  Thomas Jacovino Toll Brothers Real Estate Inc.

  2 Carriage Ln Unit 81, Chappaqua, NY 10514
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  /9

  $2,100 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.

  Mary Grant Houlihan Lawrence Inc.

  85 Paulding Dr, Chappaqua, NY 10514
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  $2,050,000 Sold Jul 31, 2025

  • 3,939 Sq Ft
  • $520/SF
  • 6 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1964

  122 Valley View Rd, Chappaqua, NY 10514

  Ideally located in the coveted Dodge Farms neighborhood, this classic Colonial offers an exceptional combination of space, charm, and functionality. Set on over 1.2 acres of lush, private property, this six-bedroom, 3.5-bath home is perfect for both everyday living and effortless entertaining. Step inside to find a sun-drenched main level featuring a spacious formal living room with a beautiful

  Sari Shaw Compass Greater NY, LLC

  122 Valley View Rd, 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
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  /16

  $1,450,000

  • 4 Beds
  • 5 Baths
  • 2,875 Sq Ft

  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 of exquisitely finished space, this residence blends timeless architectural detail with sophisticated, high-end design for the ultimate in quiet luxury. Andersen 400 series windows and doors throughout, most are

  Aric Wiser Douglas Elliman Real Estate

  136 Roaring Brook Rd, Chappaqua, NY 10514
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  /17

  $4,995 per month

  • 3 Beds
  • 1.5 Baths
  • 2,200 Sq Ft
  • Apartment for Rent

  52 Orchard Ridge Rd, Chappaqua, NY 10514

  Multi-level home featuring large rms and open plan kitch/dining area. Bdrm's are located upstairs and are well sized with beautiful crown molding and large closets. Large, flat backyard perfect for play, outdoor BBQ & entertaining includes your own small garden to grow fresh vegetables for the family. Kitchen with granite countertops, natural gas stove and stainless steel appliances. Mudroom and

  Valon Nikci Link NY Realty

  52 Orchard Ridge Rd, Chappaqua, NY 10514
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  $2,875,000 Sold Jul 31, 2025

  • 7,038 Sq Ft
  • $408/SF
  • 63 Days On Market

  • 5 Beds
  • 6.5 Baths
  • Built 1989

  26 Hemlock Hills, Chappaqua, NY 10514

  Introducing this spectacular country retreat, nestled peacefully on over four and a half acres in the leafy and much loved hamlet of Chappaqua. A glorious heated pool, panoramic patios, and endless lawns for play - offering complete privacy and seclusion, while just minutes from Chappaqua’s vibrant downtown and top-rated schools! At the end of the long scenic drive, an architectural beauty

  Wendy Alper Julia B Fee Sothebys Int. Rlty

  26 Hemlock Hills, Chappaqua, NY 10514
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  Est $2,409,092 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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  /43

  $2,000,000

  • 6 Beds
  • 6 Baths
  • 5,234 Sq Ft

  50 Overlook Dr, Chappaqua, NY 10514

  50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can

  Wendy Nolan Houlihan Lawrence Inc.

  50 Overlook Dr, Chappaqua, NY 10514
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  /26

  $9,500 per month

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  306 Quaker Rd, Chappaqua, NY 10514

  Smartly renovated 1930's Colonial walking distance to town, train, shops & school. Impressive columned front portico w/double-door entry. Formal living room w/fireplace & crown molding. Formal dining room w/French doors to patio & crown molding. High-end kitchen features Wolf, Fisher Paykel & Bosch appliances open to family room w/cathedral ceiling & French doors to patio. Main floor den/office

  Stacy Levey William Raveis-New York, LLC

  306 Quaker Rd, Chappaqua, NY 10514
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  $1,804,000 Sold Jul 31, 2025

  • 3,219 Sq Ft
  • $560/SF
  • 7 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1972

  10 Glen Terrace, Chappaqua, NY 10514

  Discover the perfect blend of elegance and comfort in this beautifully updated four-bedroom colonial, nestled in the coveted Glen Terrace cul-de-sac. This exceptional home is filled with natural light, enhanced by designer-selected colors, stylish light fixtures, and recessed lighting.The heart of the home is the spacious eat-in kitchen, featuring premium finishes such as Emerald Green

  Brendan Preston Houlihan Lawrence Inc.

  10 Glen Terrace, Chappaqua, NY 10514
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  Est $1,740,250 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,045 Sq Ft

  55 Cowdin Cir, Chappaqua, NY 10514

  55 Cowdin Cir, Chappaqua, NY 10514
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  /33

  $1,799,999

  • 4 Beds
  • 3 Baths
  • 3,009 Sq Ft

  200 Millwood Rd, Chappaqua, NY 10514

  Tucked away in a 3+ acre private storybook setting, this reimagined farmhouse blends timeless charm with modern comfort. Set back from the road on a scenic, private property with gorgeous mature landscaping, two tranquil ponds, and wide-open views, this 4-bedroom home is a peaceful retreat unlike any other.Inside, the open, sunlit layout features oversized windows that invite the outdoors in,

  Sari Shaw Compass Greater NY, LLC

  200 Millwood Rd, Chappaqua, NY 10514
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  /8

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Apartment for Rent

  91 Bedford Rd Unit 2, Chappaqua, NY 10514

  This lovely 2 bed 2 bath end unit features an EIK with glamorous modern style quartz counters, bright open floor plan. Individual balcony. Storage closet. HW/heater, washer/dryer. Quality construction built by highly regarded local builder. Amenities of this architecturally inspired building include Access control intercom/security cameras. FOB. Steel & concrete frame, rock wool insulation. Pre

  Grace Priore ERA Insite Realty Services

  91 Bedford Rd Unit 2, Chappaqua, NY 10514
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  $995,000 Sold Jul 28, 2025

  • 5,227 Sq Ft
  • $190/SF
  • 55 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1900

  2 Woodmill Rd, Chappaqua, NY 10514

  Spacious Turn-of-the-Century Converted Cider Mill – A True One-of-a-Kind Home! Nestled on just over 1 acre of lush property, this sprawling and unique home was once a cider mill and has been beautifully converted into a spacious residence. Boasting 3 working fireplaces and retaining many of its original architectural details, this home exudes character and charm. With hardwood floors, high wood

  Mark Seiden Mark Seiden Real Estate Team

  2 Woodmill Rd, Chappaqua, NY 10514
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  Est $1,719,283 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,402 Sq Ft

  515 Bedford Rd, Chappaqua, NY 10514

  515 Bedford Rd, Chappaqua, NY 10514
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  /43

  $1,599,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,087 Sq Ft

  90 Prospect Dr, Chappaqua, NY 10514

  Welcome to 90 Prospect Drive, a timeless Dutch Colonial nestled on over an acre of picturesque, park-like land in the heart of Chappaqua’s walkable village center. Just a 7-minute stroll to town, train, restaurants, shops, and parks, and only a 5-minute drive to Whole Foods and Life Time Fitness, this rare in-town gem also sits in one of Westchester’s most sought-after school districts. Set back

  Stacy Levey William Raveis-New York, LLC

  90 Prospect Dr, Chappaqua, NY 10514
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  /46

  $12,000 per month

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

  105 Hardscrabble Lake Dr, Chappaqua, NY 10514

  Luxurious Estate Rental with Scenic Views & Ultimate Entertaining Space. Discover refined living in this stunning 5-bedroom, 5.5-bath Colonial home nestled on 2.2 acres on semi-private lane in the prestigious Hardscrabble Lake neighborhood. From the double Juliet staircase and soaring 2-story foyer to the chef’s dream kitchen with Viking appliances, every inch is crafted with unparalleled

  Lauren Zaccaria Houlihan Lawrence Inc.

  105 Hardscrabble Lake Dr, Chappaqua, NY 10514
• 

  $1,605,000 Sold Jul 25, 2025

  • 3,365 Sq Ft
  • $477/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  55 Old Lyme Rd, Chappaqua, NY 10514

  Classic center hall colonial with hilltop setting in desirable cul-de-sac neighborhood offering sewer/natural gas, steps from Grafflin Elem school and close to town and train., Set on gorgeous flat park-like acre surrounded by evergreens, towering trees and specimen plantings with stone walls.. Expansive Ipe deck (2012), patio, and screened porch with transom windows and high ceilings. 3

  Sena Baron William Raveis-New York, LLC

  55 Old Lyme Rd, Chappaqua, NY 10514
• 

  Est $2,582,578 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,600 Sq Ft

  76 Cowdin Ln, Chappaqua, NY 10514

  76 Cowdin Ln, Chappaqua, NY 10514
• 

  

  /50

  $1,799,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,089 Sq Ft

  73 Random Farms Dr, Chappaqua, NY 10514

  Stately and Inviting, with a rocking chair front porch, this beautifully landscaped Post-Modern Colonial sitting on .73 acres is up for sale in the highly sought-after Random Farms Community. On a lush, level property framed with shade trees, this extraordinary house is beautifully designed and laid out. Enter this 5-bedroom 4.5 bath wonder through a light-filled double height foyer featuring

  Alicja Bohmrich Houlihan Lawrence Inc.

  73 Random Farms Dr, Chappaqua, NY 10514
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  /23

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Condo for Rent

  177 Birchwood Close Unit 177, Chappaqua, NY 10514

  Beautifully maintained and renovated 2 bedroom unit: all new windows, new kitchen, new bathroom, new heating and HVAC-huge storage unit in basement, lots of storage-flooded with sunlight, private deck. Wonderful location. Sought-after OLD FARM LAKE complex. Shared complex amenities include pool, tennis and clubhouse with exercise room. Minutes from Chappaqua Train Station - great for

  Wendy Nolan Houlihan Lawrence Inc.

  177 Birchwood Close Unit 177, Chappaqua, NY 10514
• 

  $1,570,856 Sold Jul 25, 2025

  • 3,269 Sq Ft
  • $481/SF
  • 323 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2025

  16 Dewitt Dr Unit 70, Chappaqua, NY 10514

  New Construction! Move in Summer 2025! Greeley Floorplan with primary on first floor. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A private rooftop

  Thomas Jacovino Toll Brothers Real Estate Inc.

  16 Dewitt Dr Unit 70, Chappaqua, NY 10514
• 

  Est $2,973,964 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 7,764 Sq Ft

  63 Cowdin Ln, Chappaqua, NY 10514

  63 Cowdin Ln, Chappaqua, NY 10514
• 

  

  /42

  $1,475,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,539 Sq Ft

  24 Glen Terrace, Chappaqua, NY 10514

  Welcome to 24 Glen Terrace, Chappaqua, a gracious and well-maintained Colonial imbued with country charm serenely set at the end of a quiet cul-de-sac. Welcoming tiled entry foyer introduces expansive front-to-back living room with double French doors, large front-facing bay window and slider to rear deck. Adjoining formal dining room with fireplace easily accommodates feasts or fests. A skylit,

  Stacy Levey William Raveis-New York, LLC

  24 Glen Terrace, Chappaqua, NY 10514
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  /26

  $2,900 per month

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

  150 N Bedford Rd Unit 5A, Chappaqua, NY 10514

  This spacious townhouse is waiting for you to come home! This well-appointed one-bedroom, one-bathroom home will pleasantly surprise you. As you enter the house, a large living area will greet you with polished wooden flooring and plenty of sunlight from the floor-to-ceiling windows. The adjoining kitchen is stylish and practical, with ample wooden cabinets contrasting beautifully with the dark

  Xiao Hua Herman NextHome GoodLife

  150 N Bedford Rd Unit 5A, Chappaqua, NY 10514
• 

  $1,100,000 Sold Jul 22, 2025

  • 3,444 Sq Ft
  • $319/SF
  • 87 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1987

  263 Mill River Rd, Chappaqua, NY 10514

  Step through the automatic double gates into your private sanctuary, framed by a stately stone wall entrance, a charming blue stone and Belgium block walkway, and elegant wrought iron railings. This breathtaking property is beautifully landscaped with lush flower gardens, expansive emerald lawns, and an array of specimen trees and fruit plants that create a serene, park-like

  Carolina Vinciguerra RE/MAX Town & Country

  263 Mill River Rd, Chappaqua, NY 10514
• 

  Est $3,566,879 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 7,146 Sq Ft

  60 Algonquin Dr, Chappaqua, NY 10514

  60 Algonquin Dr, Chappaqua, NY 10514

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