Chappaqua Homes

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  $1,199,000 Open Fri 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

  34 Glenside Place, Chappaqua, NY 10514

  Live minutes from the heart of Chappaqua! Commuters dream to live in this charming tudor-style home near all everyday amenities. Nestled on 1.11 acres, with 3-bedrooms and 2 bathrooms, this fully renovated residence offers timeless character and thoughtful updates throughout. The main level features an inviting entry foyer, a chef’s eat-in kitchen equipped with a gas oven/range, microwave, and

  Christine Ricci Keller Williams NY Realty

  34 Glenside Place, Chappaqua, NY 10514
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  $6,500 per month

  • 5 Beds
  • 3.5 Baths
  • 5,611 Sq Ft
  • House for Rent

  188 Orchard Ridge Rd, Chappaqua, NY 10514

  Nestled on over 3 acres, this elegant 1897 Colonial blends timeless charm with modern updates. The home retains its authentic 19th-century character, featuring a gracious veranda overlooking a sprawling backyard, coffered ceilings, exquisite millwork, rich hardwood floors, and four fireplaces throughout. Step into the expansive first floor and discover a grand living room anchored by a striking

  Deborah Cuiffo Coldwell Banker Realty

  188 Orchard Ridge Rd, Chappaqua, NY 10514
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  $727,500 Sold May 28, 2025

  • 1,660 Sq Ft
  • $438/SF
  • 11 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  386 N Greeley Ave Unit 43B, Chappaqua, NY 10514

  Welcome to 386 N. Greeley Ave, a beautifully renovated, move-in-ready home located in the sought-after Chestnut Oaks community in Chappaqua. This bright and spacious two-bedroom condo offers offers low-maintenance living with the perfect blend of style, comfort, and convenience. Located in the award-winning Chappaqua School District, this sun-filled upper-level unit has been thoughtfully updated

  Rachel Lacoste Houlihan Lawrence Inc.

  386 N Greeley Ave Unit 43B, Chappaqua, NY 10514
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  Est $2,472,561 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,971 Sq Ft

  69 High Way, Chappaqua, NY 10514

  69 High Way, Chappaqua, NY 10514
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  /23

  $820,000 Open Sat 12:30PM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,925 Sq Ft

  149 King St Unit 15, Chappaqua, NY 10514

  149 King Street offers a rare opportunity to live in downtown Chappaqua where restaurants, shops, playgrounds, farmers market, library, train, school and Starbucks are all within walking distance. This bright and pristine end unit townhome boasts a no step covered entry level which offers access to the garage, utilities, laundry and a den/playroom. The second level consists of an open

  Janet Short Houlihan Lawrence Inc.

  149 King St Unit 15, Chappaqua, NY 10514
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  $3,500 per month

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

  91 Bedford Rd Unit 2, Chappaqua, NY 10514

  This lovely one bedroom plus den apartment features and EIK with glamourous modern style quartz counters, bright open floor plan. Individual balcony. Storage closet included. 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 and concrete frame

  Grace Priore ERA Insite Realty Services

  91 Bedford Rd Unit 2, Chappaqua, NY 10514
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  $415,000 Sold May 08, 2025

  • 980 Sq Ft
  • $423/SF
  • 16 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1983

  150 N Bedford Rd Unit C9, Chappaqua, NY 10514

  Welcome to effortless in-town living! This ground-floor condo in sought-after Chappaqua Commons offers an unbeatable location adjacent to downtown Chappaqua's charming shops, restaurants, award-winning schools, and convenient public transportation. Floor-to-ceiling windows flood the living area with natural light, complementing brand-new floors & creating a sunny, inviting atmosphere. With

  Jessica Broomhead Compass Greater NY, LLC

  150 N Bedford Rd Unit C9, Chappaqua, NY 10514
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  Est $1,732,166 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,556 Sq Ft

  40 High Way, Chappaqua, NY 10514

  40 High Way, Chappaqua, NY 10514
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  /19

  $629,000

  • 2 Beds
  • 2 Baths
  • 1,608 Sq Ft

  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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  /18

  $5,600 per month

  • 2 Beds
  • 3.5 Baths
  • 2,065 Sq Ft
  • Condo for Rent

  33 Rambling Brook Rd Unit 33, Chappaqua, NY 10514

  One-of-a-kind Old Farm Lake townhouse with scenic pond views. Totally renovated with quality amenities and finishings. Living room/fireplace/sliding glass doors to deck. Den/office. Dine-in kitchen with stainless appliances. Primary Bedroom with custom walk-in closet/walk-in shower. Attic storage. Second bedroom with private bath. Finished lower level with family room w/built-in entertainment

  Holly Tsuei Houlihan Lawrence Inc.

  33 Rambling Brook Rd Unit 33, Chappaqua, NY 10514
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  $515,000 Sold May 07, 2025

  • 1,387 Sq Ft
  • $371/SF
  • 14 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1987

  12 Highland Ave Unit C, Chappaqua, NY 10514

  Welcome to 12 Highland Ave, a beautifully updated condo, located in the heart of historic Chappaqua, NY. This move-in-ready home offers the perfect combination of convenience and comfort, just steps from the train station, shops, restaurants, and more.This two-level residence on two levels providing the flexibility to live like a two-bedroom home. The main floor includes a foyer, a bright living

  Natalia Wixom Compass Greater NY, LLC

  12 Highland Ave Unit C, Chappaqua, NY 10514
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  Est $584,759 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,563 Sq Ft

  379 N Greeley Ave Unit 40A, Chappaqua, NY 10514

  379 N Greeley Ave Unit 40A, Chappaqua, NY 10514
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  /22

  $1,099,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  5 Crossways, Chappaqua, NY 10514

  Move right into this walk-to-town beautifully updated 4-bedroom, 2.5-bath Colonial that offers the perfect balance of classic charm and modern convenience. Just steps from the heart of Chappaqua, this home features an open-concept layout and flexible spaces ideal for everyday living and effortless entertaining.Step through the storybook Dutch door to a light-filled, double-height entry with a

  Jill Urban Compass Greater NY, LLC

  5 Crossways, Chappaqua, NY 10514
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  /36

  $11,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,039 Sq Ft
  • House for Rent

  68 Spruce Ln S, Chappaqua, NY 10514

  A fully-furnished, lovingly maintained colonial home for rent in the heart of Chappaqua! A commuter's dream: only minutes to town, train, library, shops, and everything downtown Chappaqua has to offer. This spacious home is available for a one-year term, July 2025-2026. Featuring an updated kitchen, plentiful rooms with natural light, beautiful land with two patio/entertaining areas, a carriage

  Wendy Nolan Houlihan Lawrence Inc.

  68 Spruce Ln S, Chappaqua, NY 10514
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  $975,000 Sold Apr 29, 2025

  • 1,819 Sq Ft
  • $536/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1946

  2 Brook Ln, Chappaqua, NY 10514

  Welcome to 2 Brook Lane, Chappaqua, NY – a beautifully maintained and expanded 3-bedroom home with additional office room, cherished by the same owners for over 30 years. Nestled on a flat quarter-acre corner lot, this delightful residence offers abundant space for gardening and outdoor activities.Upon entering, you'll find a thoughtfully renovated home featuring an open living area that

  MaryAnn Bayer Compass Greater NY, LLC

  2 Brook Ln, Chappaqua, NY 10514
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  Est $485,156 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,140 Sq Ft

  373 N Greeley Ave, Chappaqua, NY 10514

  373 N Greeley Ave, Chappaqua, NY 10514
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  $1,200,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,246 Sq Ft

  45 Crossways, Chappaqua, NY 10514

  Storybook 1930’s-era Tudor-style shingle cottage delightfully renovated & updated with all the comforts for the 21st century. Believed to be originally derived from Standard Homes Co. classic Densmore model. A welcoming entry vestibule with French door introduces a wide, front-facing living room, warmed by a stout wood-burning fireplace. Gather together in the dining room to enjoy holiday feasts

  Stacy Levey William Raveis-New York, LLC

  45 Crossways, 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
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  $875,000 Sold Apr 03, 2025

  • 1,664 Sq Ft
  • $526/SF
  • 6 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  149 King St Unit 19, Chappaqua, NY 10514

  Location. Location. Location. Movie right in! Impeccable 2 bedroom 2.5 bath with a Loft, 2-attached car garage, deck, end-unit in the heart of Chappaqua! This beautiful home has it all: elegant interior, a wonderful vista of surrounding countryside, open floor plan, hardwood floors on main floor, very bright with wall of new windows throughout. Main level consits of modern eat-in-kitchen with

  Alicja Bohmrich Houlihan Lawrence Inc.

  149 King St Unit 19, Chappaqua, NY 10514
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  Est $412,421 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,008 Sq Ft

  370 N Greeley Ave, Chappaqua, NY 10514

  370 N Greeley Ave, Chappaqua, NY 10514
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  /40

  $1,499,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,858 Sq Ft

  52 Old Lyme Rd, Chappaqua, NY 10514

  Updated and well appointed 3800+ sq ft, 4 bedroom Colonial on sewer and gas in a Chappaqua, close to town, prime location. This spacious Colonial offers an ideal blend of open flow, comfort, and convenience. A gracious expansive foyer welcomes you to the light-filled living and dining rooms, both featuring bay windows. The gourmet eat-in kitchen boasts top-of-the-line finishes and appliances,

  Cindy Glynn Compass Greater NY, LLC

  52 Old Lyme Rd, 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
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  $635,000 Sold Mar 28, 2025

  • 1,724 Sq Ft
  • $368/SF
  • 6 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  173 Birchwood Close Unit 173, Chappaqua, NY 10514

  Welcome to this beautifully maintained, sun-filled, 2-bedroom, 2-bath end unit located in the sought-after Old Farm Lake Condominiums, within the award-winning Chappaqua School District. Perfectly situated just moments from the train station, schools, shops, and restaurants, this home offers the ultimate in convenience and community living. Step inside to discover gleaming hardwood floors and an

  Cindy Glynn Compass Greater NY, LLC

  173 Birchwood Close Unit 173, Chappaqua, NY 10514
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  Est $584,059 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  343 N Greeley Ave Unit 8D, Chappaqua, NY 10514

  343 N Greeley Ave Unit 8D, Chappaqua, NY 10514
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  $745,000 Sold Mar 25, 2025

  • 1,296 Sq Ft
  • $575/SF
  • 63 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  105 Rambling Brook Rd, Chappaqua, NY 10514

  Situated in the highly sought-after Old Farm Lake complex, this bright 2-bedroom condo boasts high ceilings and an abundance of natural light. It offers a carefree lifestyle with exceptional amenities. Just a 5-minute drive to the Metro-North train station and the vibrant downtown area of Chappaqua offering easy access to dining, shopping, and entertainment. Enter through a tiled foyer into the

  Mark Boyland Keller Williams Realty Partner

  105 Rambling Brook Rd, Chappaqua, NY 10514
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  Est $606,366 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,618 Sq Ft

  328 N Greeley Ave Unit 14C2, Chappaqua, NY 10514

  328 N Greeley Ave Unit 14C2, Chappaqua, NY 10514
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  $912,483 Sold Mar 21, 2025

  • 1,440 Sq Ft
  • $634/SF
  • 133 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1905

  9 Elm St, Chappaqua, NY 10514

  This 2-family duplex offers an incredible opportunity for both investors and homeowners alike. Prime neighborhood location in the shopping district, close to the train and schools in Chappaqua NY. Each unit features a covered front porch, two bedrooms, hardwood floors, private laundry, and outdoor deck space to a shared yard. Situated on a level 0.26-acre lot, the property includes a private

  Edward Holmes William Raveis-New York, LLC

  9 Elm St, Chappaqua, NY 10514
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  Est $503,506 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,226 Sq Ft

  301 N Greeley Ave, Chappaqua, NY 10514

  301 N Greeley Ave, Chappaqua, NY 10514
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  $1,200,000 Sold Feb 28, 2025

  • 2,288 Sq Ft
  • $524/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1994

  30 Lori Ln, Chappaqua, NY 10514

  Move right in! Enjoy easy living in this updated, sun-filled home located in a quiet neighborhood close to downtown Chappaqua. This meticulously maintained home offers a spacious and open layout ideal for entertaining and everyday gatherings. The renovated eat in kitchen with granite countertops and large center island opens to the dining room and sun-drenched family room with doors to the

  Dana Goldman Compass Greater NY, LLC

  30 Lori Ln, Chappaqua, NY 10514
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  Est $543,617 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft

  320 N Greeley Ave, Chappaqua, NY 10514

  320 N Greeley Ave, Chappaqua, NY 10514
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  $750,000 Sold Feb 18, 2025

  • 1,549 Sq Ft
  • $484/SF
  • 27 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  7 Deer Run Unit 7, Chappaqua, NY 10514

  Step into luxury - in this fully renovated condo in Chappaqua at Old Farm Lake development, close to town, train, shops and schools. Enter the foyer with marble floors, leading to the kitchen with Bosch stainless appliances and walk out to front patio. The dining room opens to a spacious living room with a vaulted high ceiling with skylights and decorated with hardwood, complete with a stunning

  Natalia Wixom Compass Greater NY, LLC

  7 Deer Run Unit 7, Chappaqua, NY 10514
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  Est $1,388,339 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,919 Sq Ft

  6 Cindy Way, Chappaqua, NY 10514

  6 Cindy Way, Chappaqua, NY 10514
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  $1,955,000 Sold Feb 04, 2025

  • 3,541 Sq Ft
  • $552/SF
  • 8 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1955

  40 Aldridge Rd, Chappaqua, NY 10514

  Move right in to this beautiful home perfectly situated on a tranquil cul-de-sac, offering the best of both worlds: a spacious, private retreat with the convenience of being close to town and train. This airy & bright 4-bedroom, 4-bathroom home is designed for both comfort & elegance. Discover a first-floor primary bedroom with soaring ceilings & a generous walk-in closet. The heart of the home

  Jodi Greebel Compass Greater NY, LLC

  40 Aldridge Rd, Chappaqua, NY 10514
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  Est $1,084,003 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,858 Sq Ft

  8 Orchard Ridge Terrace, Chappaqua, NY 10514

  8 Orchard Ridge Terrace, Chappaqua, NY 10514
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  $1,175,000 Sold Jan 24, 2025

  • 2,100 Sq Ft
  • $560/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1942

  33 Chatham Rd, Chappaqua, NY 10514

  Beautifully renovated home 3 bedroom 2.5 bath on 1.3 acres in Chappaqua Ridge community. With its classic center hall colonial layout and beautiful renovations, it's perfect for someone looking for both charm and modern updates. New kitchen with deck overlooking private yard Is ideal for entertaining, oversized Livingroom with wood burning fireplace, formal Dining Room, Primary suite , along

  Phyllis Lerner Corcoran Legends Realty

  33 Chatham Rd, Chappaqua, NY 10514
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  Est $1,048,728 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,293 Sq Ft

  59 Orchard Ridge Rd, Chappaqua, NY 10514

  59 Orchard Ridge Rd, Chappaqua, NY 10514
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  $1,550,000 Sold Jan 23, 2025

  • 3,631 Sq Ft
  • $427/SF
  • 17 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2004

  140 S Bedford Rd, Chappaqua, NY 10514

  Modern Colonial, nestled on a private 1.23 acre lot in the Chappaqua School District. This 4 bedroom, 3,631 sq ft open flow, expansive home is thoughtfully crafted, featuring generously sized light-filled rooms with large windows and essential amenities. A double height entry foyer with chandelier opens to formal spaces, an office/guest room, formal dining and living rooms. This comfortable, open

  Cindy Glynn Compass Greater NY, LLC

  140 S Bedford Rd, Chappaqua, NY 10514
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  /2

  Est $2,232,598 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,800 Sq Ft

  16 Evergreen Ln, Chappaqua, NY 10514

  16 Evergreen Ln, Chappaqua, NY 10514
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  $1,425,000 Sold Jan 07, 2025

  • 2,946 Sq Ft
  • $484/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1921

  29 Crossways, Chappaqua, NY 10514

  Welcome home to a 1920s Sears Roebuck English cottage style home that was impeccably renovated and expanded while honoring the original aesthetic. This walk to shopping, dining, train & school three bedroom home that can live like a four bedroom blends timeless elegance with an open, livable floor plan suited for today’s lifestyle. From the moment you enter the home through the arch doorway, you

  Amanda Goldberg William Raveis-New York, LLC

  29 Crossways, Chappaqua, NY 10514
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  Est $875,859 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  111 Castle Rd, Chappaqua, NY 10514

  111 Castle Rd, Chappaqua, NY 10514

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