Recently Sold Chappaqua, NY Homes

• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $1,600,000 Sold Jul 22, 2025

  • 3,353 Sq Ft
  • $477/SF
  • 66 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2025

  6 Dewitt Dr Unit 65, Chappaqua, NY 10514

  As you enter this END UNIT Millwood Elite Fairview, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The appealing primary bedroom suite boasts a lavish bath and ample

  Andrea Martone Houlihan Lawrence Inc.

  6 Dewitt Dr Unit 65, Chappaqua, NY 10514
• 

  $1,501,000 Sold Jul 21, 2025

  • 3,525 Sq Ft
  • $426/SF
  • 15 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1961

  23 Cross Ridge Rd, Chappaqua, NY 10514

  Spacious 4 bedroom/ 4 bathroom home that lives like a 5+ bedroom in a coveted Chappaqua neighborhood. Light and bright freshly painted updated home with hardwood floors throughout. The first floor has an entry foyer, powder room, eat-in-kitchen with granite countertops and new stainless steel appliances, living room/ dining room with fireplace and sliding doors to a wrap around deck also

  Pamela Akin Douglas Elliman Real Estate

  23 Cross Ridge Rd, Chappaqua, NY 10514
• 

  $1,125,000 Sold Jul 21, 2025

  • 1,888 Sq Ft
  • $596/SF
  • 18 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1958

  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.

  16 Garey Dr, 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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $1,450,000 Sold Jun 25, 2025

  • 2,533 Sq Ft
  • $572/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1950

  132 Devoe Rd, Chappaqua, NY 10514

  Welcome to this lovely home within the very desirable Hillholme community in Chappaqua. Perfectly maintained and set beautifully on a flat large acre for all to enjoy. The bedrooms are all very spacious, there is a dedicated home office/study that ensures productivity, while the basement adds a great space for a play area. The backyard is a dream - lush green grass, deck and patio for barbecues

  Yona Strougo Compass Greater NY, LLC

  132 Devoe Rd, Chappaqua, NY 10514
• 

  $3,000,000 Sold Jun 23, 2025

  • 6,333 Sq Ft
  • $474/SF
  • 21 Days On Market

  • 6 Beds
  • 7.5 Baths
  • Built 1994

  66 Kerry Ln, Chappaqua, NY 10514

  Welcome Home to Your Dream Colonial in the Chappaqua School District. Discover luxury and comfort in this sunlit center-hall colonial, boasting over 6,333+ square feet of living space. Set back on 2.25 private, level acres, this home features a fenced-in backyard with a heated saltwater pool, an automatic cover, and expansive patio and deck spaces perfect for entertaining and recreation.

  Stacey Sporn William Raveis Real Estate

  66 Kerry Ln, Chappaqua, NY 10514
• 

  $1,402,970 Sold Jun 23, 2025

  • 2,945 Sq Ft
  • $476/SF
  • 142 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2024

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514

  HOME IS UNDER CONSTRUCTION. MOVE in SUMMER 2025. 2 BR, 3 Full, 1 half primary on main floor, finished basement with full bath and media room. Additional Information: ParkingFeatures:2 Car Attached,

  Thomas Jacovino Toll Brothers Real Estate Inc.

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514
• 

  $1,250,000 Sold Jun 20, 2025

  • 2,144 Sq Ft
  • $583/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  64 Stornowaye St, Chappaqua, NY 10514

  Inside & outside blend seamlessly together throughout this sleek, modern 3-bed/2-bath contemporary, wrapped by a massive deck front, side & rear, and privately set back from the road on two peaceful, sylvan acres on a cul-de-sac in the sought-after Whippoorwill neighborhood. Great layout for entertaining. Arts & crafts-inspired living room illuminated by large front-facing windows & topped with a

  Stacy Levey William Raveis-New York, LLC

  64 Stornowaye St, Chappaqua, NY 10514
• 

  $2,450,000 Sold Jun 20, 2025

  • 6,495 Sq Ft
  • $377/SF
  • 46 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1995

  11 Boulder Trail, Chappaqua, NY 10514

  Spectacular 5-bedroom, 4 1/2 bath, 6,495 sq ft Colonial, located in the sought after Hardscrabble Lake neighborhood within the renowned Chappaqua School District. This home features a spacious, sun drenched open floor plan accented by large rooms, high ceilings, refined hardwood floors, walls of windows, and exquisite detailing throughout. As one enters, the expansive cathedral ceiling front

  Cindy Glynn Compass Greater NY, LLC

  11 Boulder Trail, Chappaqua, NY 10514
• 

  $1,500,000 Sold Jun 17, 2025

  • 3,230 Sq Ft
  • $464/SF
  • 25 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1964

  23 Round Hill Rd, Chappaqua, NY 10514

  Welcome to 23 Round Hill Road, a picture-perfect, timeless, Center Hall Colonial on a premier street just minutes from Chappaqua schools, train station, & a variety of restaurants, shops & grocery stores (including Whole Foods & Starbucks), a prime location for convenience & lifestyle. Set on a beautifully landscaped property, this home exudes classic appeal. As you step through double front

  Michael Levy eXp Realty

  23 Round Hill Rd, Chappaqua, NY 10514
• 

  $1,610,000 Sold Jun 16, 2025

  • 3,858 Sq Ft
  • $417/SF
  • 10 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1969

  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
• 

  $1,624,995 Sold Jun 13, 2025

  • 3,352 Sq Ft
  • $485/SF
  • 1 Day On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2025

  22 Dewitt Dr Unit 73, Chappaqua, NY 10514

  Under Construction. As you enter the Millwood Elite, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The appealing primary bedroom suite boasts a lavish bath and ample

  Thomas Jacovino Toll Brothers Real Estate Inc.

  22 Dewitt Dr Unit 73, Chappaqua, NY 10514
• 

  $1,649,995 Sold Jun 13, 2025

  • 3,269 Sq Ft
  • $505/SF
  • 46 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2025

  9 Dewitt Dr Unit 80, Chappaqua, NY 10514

  Move-in Spring 2025! As you enter the Greeley Fairview, the exquisite foyer presents sweeping views of this home's luxurious finishes. The open-concept kitchen and great room provide the ideal space for entertaining. The casual dining area is adjacent to the kitchen and provides a convenient and intimate setting. The great room is the perfect setting for relaxation with its cozy fireplace and

  Thomas Jacovino Toll Brothers Real Estate Inc.

  9 Dewitt Dr Unit 80, Chappaqua, NY 10514
• 

  $1,826,000 Sold Jun 10, 2025

  • 3,962 Sq Ft
  • $461/SF
  • 7 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1960

  24 Hunting Ridge Rd, Chappaqua, NY 10514

  Extremely spacious and meticulously maintained 4 bedroom/ 4 bathroom home with almost 4000sf that lives like a 5 bedroom on a cul de sac in a sought after Chappaqua neighborhood! It has an amazing gourmet Chef's Kitchen with large center island, stainless appliances, a spacious eating area with access to the back patio. The kitchen was renovated in 2024 which included new quartz countertops, new

  Pamela Akin Douglas Elliman Real Estate

  24 Hunting Ridge Rd, Chappaqua, NY 10514
• 

  $2,922,500 Sold Jun 10, 2025

  • 5,836 Sq Ft
  • $501/SF
  • 127 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1901

  51 Granite Ct, Chappaqua, NY 10514

  Sophisticated and Stunning Chappaqua Estate! Sure to please the most discerning buyer, this fully modernized Normandy-styled estate, sited on magnificent property, in a a cul-de-sac, walking distance to schools and parks, is one of a kind. This distinctive home, owned by two esteemed art collectors, and dating back to the late 1800s, has been meticulously overhauled with impeccable taste,

  Cindy Glynn Compass Greater NY, LLC

  51 Granite Ct, Chappaqua, NY 10514
• 

  $1,502,500 Sold Jun 09, 2025

  • 2,426 Sq Ft
  • $619/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  60 Cross Ridge Rd, Chappaqua, NY 10514

  Easy living in this comfortable, light-filled, classic split-level home endowed with spacious rooms, an expanded designer kitchen w/windowed breakfast area & adjoining sunroom w/slider to deck set on a useful, flat, 1.37-acre parcel. Welcoming formal living room w/wood burning fireplace and large picture windows front & rear. Centrally-located formal dining room easily accommodates large

  Stacy Levey William Raveis-New York, LLC

  60 Cross Ridge Rd, Chappaqua, NY 10514
• 

  $1,800,000 Sold Jun 07, 2025

  • 6,814 Sq Ft
  • $264/SF
  • 43 Days On Market

  • 7 Beds
  • 6 Baths
  • Built 1969

  85 Haights Cross Rd, Chappaqua, NY 10514

  Come experience not only an extraordinarily designed residence, additionally enjoy a home set atop quite possibly one of the highest viewpoints in Chappaqua. Commissioned by the Mechner family in 1969, architect John Koster worked closely with present owners to develop a property like no other. Sited on 8.86 wooded acres with vintage log cabin and sculptural stone outcroppings inspired a

  Amy Via Houlihan Lawrence Inc.

  85 Haights Cross Rd, Chappaqua, NY 10514
• 

  $1,320,000 Sold Jun 06, 2025

  • 2,628 Sq Ft
  • $502/SF
  • 6 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1968

  7 Oak Hill Rd, Chappaqua, NY 10514

  Welcome to 7 Oak Hill Road, Chappaqua, a spacious and lovingly maintained 4-Bed/3-Bath Raised Ranch set on a flat .67-acre parcel on a neighborly street and buffered by a bird sanctuary. A covered front porch introduces a double-door entry. Large windows front and rear bathe the wide, open living and dining rooms in soft, natural light. Dine casually in the morning-sun-facing breakfast area of

  Stacy Levey William Raveis-New York, LLC

  7 Oak Hill Rd, Chappaqua, NY 10514
• 

  $1,415,000 Sold Jun 06, 2025

  • 2,781 Sq Ft
  • $509/SF
  • 10 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1978

  24 Greenbriar Dr, Chappaqua, NY 10514

  Nestled on a quiet cul-de-sac street, 24 Greenbriar Drive seamlessly blends quality construction with modern amenities. This beautifully updated and meticulously maintained four-bedroom, three-bathroom home is truly turnkey.The renovated kitchen is perfect for both everyday living and entertaining, featuring a breakfast nook with built-in seating and a sliding glass door that opens to a spacious

  Jennifer Harris Compass Greater NY, LLC

  24 Greenbriar Dr, Chappaqua, NY 10514
• 

  $870,000 Sold Jun 04, 2025

  • 1,492 Sq Ft
  • $583/SF
  • 12 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1905

  10 Leroy Place, Chappaqua, NY 10514

  Welcome to your next adventure! This cozy 2-bedroom cottage is nestled on a picturesque piece of land, offering endless potential for those with vision and creativity. Surrounded by nature, this property is perfect for those looking for a peaceful retreat, a weekend getaway, or a renovation project to make their own.Though in need of remodeling, the home provides a solid foundation to bring your

  Danae Richards William Raveis-New York, LLC

  10 Leroy Place, Chappaqua, NY 10514
• 

  $970,000 Sold May 30, 2025

  • 1,923 Sq Ft
  • $504/SF
  • 11 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1850

  33 Kipp St, Chappaqua, NY 10514

  Welcome to 33 Kipp Street in Chappaqua, a vintage country farmhouse that exudes charm and character. Perched on a picturesque hillside, this three-bedroom home invites you in with its classic rocking chair front porch—a perfect spot to unwind and enjoy the serene surroundings.Spanning 1,923 square feet, the home was lovingly restored in 2011, seamlessly blending historic charm with modern

  Deena Bouchier Compass Greater NY, LLC

  33 Kipp St, Chappaqua, NY 10514
• 

  $1,558,667 Sold May 30, 2025

  • 2,945 Sq Ft
  • $529/SF
  • 23 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2024

  20 Dewitt Dr Unit 72, Chappaqua, NY 10514

  HOME IS UNDER CONSTRUCTION- READY FOR FALL 2024 CLOSING2 BR Briarcliff Floorplan with primary on first floor. A finished basement with half bath give plenty of room for everyone to enjoy. This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping, cafes,

  Thomas Jacovino Toll Brothers Real Estate Inc.

  20 Dewitt Dr Unit 72, Chappaqua, NY 10514
• 

  $2,300,000 Sold May 29, 2025

  • 4,490 Sq Ft
  • $512/SF
  • 6 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1992

  25 Random Farms Dr, Chappaqua, NY 10514

  Welcome to this sophisticated 4-bedroom Colonial in Random Farms, one of Chappaqua’s most sought-after communities. Designed with an open-flow layout and abundant natural light, this home offers effortless connectivity between spacious living areas—ideal for everyday living, entertaining, and working from home.Recent enhancements include a new roof, solar panels, and upgraded mechanical systems,

  Sari Shaw Compass Greater NY, LLC

  25 Random Farms Dr, Chappaqua, NY 10514
• 

  $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
• 

  $1,589,000 Sold May 28, 2025

  • 3,041 Sq Ft
  • $523/SF
  • 26 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1955

  395 Bedford Rd, Chappaqua, NY 10514

  An impressive and tastefully appointed five bedroom colonial home in the much sought after Chappaqua School District. Set on just over one beautiful acre of level land, this impressive home offers the perfect blend of tranquility and convenience, with easy access to the Chappaqua train station. The heart of the home is the spacious, airy, sun-filled family room, featuring a wall of full length

  Catherine O'Connor Houlihan Lawrence Inc.

  395 Bedford Rd, Chappaqua, NY 10514
• 

  $1,450,000 Sold May 22, 2025

  • 2,233 Sq Ft
  • $649/SF
  • 9 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1936

  2 South Place, Chappaqua, NY 10514

  Welcome to 2 South Place - A stylish family home in the desirable Hillholme Community of Chappaqua, within the Chappaqua School District. This residence blends an integration of classic traditional and modern design offering elegant living spaces and a prime location. First level includes a Classic living room with fireplace, recess lighting, formal dinning room, recess lighting. Gourmet

  Toni DiMichelo Houlihan Lawrence Inc.

  2 South Place, Chappaqua, NY 10514
• 

  $1,715,408 Sold May 16, 2025

  • 3,269 Sq Ft
  • $525/SF
  • 39 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2024

  3 Dewitt Dr Unit 77, 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.

  3 Dewitt Dr Unit 77, Chappaqua, NY 10514

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