Chappaqua, NY Homes

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  /38

  $1,175,000

  • 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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  /25

  $2,400 - $6,700 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
• 

  $1,775,000 Sold Jul 17, 2025

  • 3,587 Sq Ft
  • $495/SF
  • 7 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1969

  3 Sunset Dr, Chappaqua, NY 10514

  Welcome to your beautifully maintained 4-bedroom Colonial at 3 Sunset Drive in the heart of Chappaqua! This charming home boasts 3.5 bathrooms and offers a spacious 3,587 square feet of living space. Step inside to find oak wood flooring throughout and a wood-paneled home office, perfect for working from home. Large windows fill the space with natural light, creating a warm and inviting

  Debra Goldenberg Compass Greater NY, LLC

  3 Sunset Dr, 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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  /44

  $899,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  16 Garey Dr, Chappaqua, NY 10514

  Step into a beautifully refreshed Chappaqua residence. This inviting home boasts stunning wooded views, creating a serene and tranquil atmosphere. The thoughtfully designed layout flows seamlessly, connecting a spacious formal living room, an elegant dining area, and a bright, eat-in kitchen. From the kitchen, step out onto a large deck, perfect for alfresco dining and entertaining amidst the

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 303-7715

  16 Garey Dr, 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
• 

  $1,850,000 Sold Jul 15, 2025

  • 4,419 Sq Ft
  • $419/SF
  • 17 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1972

  22 Mountain Peak Rd, Chappaqua, NY 10514

  Beautiful views welcome you to this updated 5 bedroom Colonial, professionally landscaped and located on a perfect cul de sac close to town and schools! The first floor boasts a gracious formal living room w/ a wood-burning fireplace and formal dining rm featuring a sunny bay window. Chef's eat in kitchen with granite counters, island with seating and sliding glass doors to the deck. The

  Usha Subramaniam Compass Greater NY, LLC

  22 Mountain Peak Rd, Chappaqua, NY 10514
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  Est $1,492,936 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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  /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
• 

  $2,315,000 Sold Jul 14, 2025

  • 4,199 Sq Ft
  • $551/SF
  • 13 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1927

  55 Deepwood Dr, Chappaqua, NY 10514

  Set on 1.04 level acres of beautifully landscaped property with vibrant perennial gardens and mature plantings, this impeccably renovated four-bedroom, three-and-a-half-bathroom Center Hall Colonial offers 4,199 square feet of thoughtfully designed living space in one of Chappaqua’s most sought-after neighborhoods. A gracious foyer with a classic sweeping staircase welcomes you into the home.

  Avital Soldatenko Houlihan Lawrence Inc.

  55 Deepwood Dr, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 4 Beds

  767 King St, Chappaqua, NY 10514

  767 King St, Chappaqua, NY 10514
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  /17

  $1,629,995 Pending

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

  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
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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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  $999,999 Sold Jul 14, 2025

  • 2,440 Sq Ft
  • $410/SF
  • 10 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1925

  12 Spring Ln, Chappaqua, NY 10514

  Nestled in the heart of Chappaqua, this enchanting stone and wood colonial is move in ready with updates throughout! This two bedroom two and a half bath residence lives like a three bedroom! Just a short walk to shopping, restaurants, parks, school and the train. Beyond the inviting front porch you will find both comfort and charm. The main floor has beautiful beamed ceilings throughout and a

  Suzanne Sanborn William Raveis Real Estate

  12 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
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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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  /20

  $3,500 per month

  • 1 Bed
  • 1.5 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  352 N Greeley Ave, Chappaqua, NY 10514

  Large bright 1Bedroom plus loft in a two story apartment in Chestnut Oaks Condominium. Washer dryer in the unit. Wood fireplace. Short walk to the downtown center and train station. Complex offers Community Pool and Tennis. One car garage included, plus there is unassigned parking and guest parking. Tenant pays all utilities. Landlord will replace kitchen cabinets and kitchen countertop.

  Gabriela Kosek ERA Insite Realty Services

  352 N Greeley Ave, Chappaqua, NY 10514
• 

  $2,512,255 Sold Jul 11, 2025

  • 4,004 Sq Ft
  • $627/SF
  • 47 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1942

  35 Ivy Hill Rd, Chappaqua, NY 10514

  Arise to astonishing sunrises in this gorgeous, modern farmhouse privately set on 2.75 estate-like acres at the end of a cul-de-sac in prestigious Lawrence Farms East. Newly rebuilt in 2020 and further refined since. Grand, two-story entry foyer introduces open floor plan for today’s contemporary living style. Inviting living/dining area with large, front-facing windows, wood-burning fireplace,

  Stacy Levey William Raveis-New York, LLC

  35 Ivy Hill Rd, Chappaqua, NY 10514
• 

  Est $2,466,466 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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  /49

  $2,200,000 Open Sun 12PM - 2PM

  • 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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  /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
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  $1,600,000 Sold Jul 09, 2025

  • 4,086 Sq Ft
  • $392/SF
  • 7 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1937

  25 Campfire Rd, Chappaqua, NY 10514

  Discover the enduring charm of this distinguished 1937 Country Colonial, offering over 4,000 square feet of dramatic, sun-filled living space. Majestically sited on over one beautifully landscaped acre, this home features level play areas and exceptional outdoor entertainment spaces, seamlessly blending classic elegance with modern updates. The impressive Great Room captivates with its vaulted

  Cindy Glynn Compass Greater NY, LLC

  25 Campfire Rd, Chappaqua, NY 10514
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  Est $1,646,192 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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  /43

  $1,599,000

  • 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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  /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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  $1,890,000 Sold Jul 09, 2025

  • 3,746 Sq Ft
  • $505/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1967

  18 Valley Ln, Chappaqua, NY 10514

  Welcome to 18 Valley Lane, a four-bedroom colonial situated on a sort after quiet street in Chappaqua. The main level consists of a living room, dining room, office, powder room and a large open eat-in kitchen/family room great for entertaining with access to a screened-in porch, outdoor bluestone patio and backyard. The upstairs consists of a large primary bedroom suite with a dressing area,

  Susan Slotnick William Raveis Real Estate

  18 Valley Ln, Chappaqua, NY 10514
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  Est $1,672,989 Not Listed For Sale

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

  515 Bedford Rd, Chappaqua, NY 10514

  515 Bedford Rd, Chappaqua, NY 10514
• 

  

  /50

  $1,799,000

  • 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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  /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
• 

  $1,835,000 Sold Jun 30, 2025

  • 4,082 Sq Ft
  • $450/SF
  • 6 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1965

  20 Bristol Place, Chappaqua, NY 10514

  Welcome to 20 Bristol Place, a stunning home nestled at the end of a peaceful cul-de-sac in Chappaqua, NY. This modern home boasts an open and bright layout, offering 4 bedrooms and 4 bathrooms across 4,082 square feet of luxurious living space. The oversized primary bedroom features high ceilings and a renovated bath, providing a serene retreat.The heart of the home is the high-end

  Kori Sassower Compass Greater NY, LLC

  20 Bristol Place, Chappaqua, NY 10514
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  Est $3,615,950 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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  /47

  $1,599,000

  • 5 Beds
  • 4.5 Baths
  • 5,357 Sq Ft

  43 Random Farms Cir, Chappaqua, NY 10514

  Discover the most private home in the prestigious Random Farms community of Chappaqua, NY. Tucked away amid lush, mature landscaping, this stunning five-bedroom contemporary colonial offers a rare sense of natural seclusion and tranquility. Enjoy the ultimate in privacy without sacrificing convenience—just a short stroll to the neighborhood pool, clubhouse, and tennis courts. This exceptional

  Suzan Zeolla Houlihan Lawrence Inc.

  43 Random Farms Cir, Chappaqua, NY 10514
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  /29

  $8,500 per month

  • 5 Beds
  • 5.5 Baths
  • 4,616 Sq Ft
  • House for Rent

  675 Quaker Rd, Chappaqua, NY 10514

  Flexible Rental - Short or Long Term Options Available. Lovely 5 bed/5 bath split level home in prime Chappaqua location. Enjoy privacy on over an acre that borders the protected land of the Audubon Sanctuary. Special features include soaring vaulted ceilings, walk-in closets and ample storage in beautiful custom built-ins throughout the home, and established gardening beds. Multiple outdoor

  Margaret Harrington Douglas Elliman Real Estate

  675 Quaker Rd, Chappaqua, NY 10514
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  $1,690,995 Sold Jun 30, 2025

  • 3,335 Sq Ft
  • $507/SF
  • 199 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  18 Dewitt Dr Unit 71, Chappaqua, NY 10514

  HOME NOT COMPLETED YET- 3 BR Millwood Elite home. This outstanding home is located in the heart of the neighborhood where you can walk to shopping, cafe, gym, pool and more. Includes 3 BR + 2 offices, loft and outdoor terrace w built in grill and linear fireplace and interior wet bar in loft. The open concept great room and kitchen allow for large family gatherings. The open island with

  Thomas Jacovino Toll Brothers Real Estate Inc.

  18 Dewitt Dr Unit 71, Chappaqua, NY 10514
• 

  Est $4,566,166 Not Listed For Sale

  • 5 Beds
  • 9 Baths
  • 12,436 Sq Ft

  44 Algonquin Dr, Chappaqua, NY 10514

  44 Algonquin Dr, Chappaqua, NY 10514
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  /41

  $2,225,000

  • 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
• 

  $2,250,000 Sold Jun 27, 2025

  • 4,807 Sq Ft
  • $468/SF
  • 18 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1993

  97 Random Farms Dr, Chappaqua, NY 10514

  Nestled in the prestigious Random Farms community, this beautifully updated 4-bedroom Colonial blends timeless elegance with modern convenience. Designed for effortless living, the open-flow layout seamlessly connects the renovated chef’s kitchen to a sun drenched great room, featuring a sophisticated fireplace as its centerpiece, while formal living and dining spaces add refinement. A dedicated

  Sari Shaw Compass Greater NY, LLC

  97 Random Farms Dr, Chappaqua, NY 10514
• 

  Est $1,552,085 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,946 Sq Ft

  22 Stornowaye St, Chappaqua, NY 10514

  22 Stornowaye St, 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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