New Castle, NY Homes

/50
$1,350,000

Open Sun 12:30PM - 3PM
- 5 Beds
- 3.5 Baths
- 4,828 Sq Ft
15 Inningwood Rd, Ossining, NY 10562

A once-in-a-lifetime opportunity to own Maplehurst Farm, originally known as the Conklin-Chadeayne Farmhouse, an irreplaceable Antique Farmhouse Colonial estate dating back to the 1730s, nestled on five irreplaceable acres in the highly sought-after community of New Castle. Rich in history and timeless character, this extraordinary property preserves many of its original architectural details,

Annemarie Credentino BHHS River Towns Real Estate

15 Inningwood Rd, Ossining, NY 10562
$460,000

Sold May 01, 2026

356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
- 1 Bed
- 1.5 Baths
- 1,207 Sq Ft
- Built 1988
Last Sold Summary
- 15% Below List Price
- $381/SF
- 162 Days On Market
Current Estimated Value $480,125

Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.

356 N Greeley Ave Unit 28G, Chappaqua, NY 10514

Not Listed For Sale

130 Pinesbridge Rd, Ossining, NY 10562
- 4 Beds
- 3 Baths
- 2,644 Sq Ft
- Built 1946
130 Pinesbridge Rd, Ossining, NY 10562

Last Sold Summary
- 168 Days On Market
Last Listing Agent Natalia Wixom Compass Greater NY, LLC

/27
$579,000

Pending
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
309 N Greeley Ave Unit 5C, Chappaqua, NY 10514

Welcome to 309 N. Greeley Avenue. This lovely first floor Town House in the sought-after Chestnut Oaks Community is conveniently located to the heart of downtown Chappaqua. With the award-winning Chappaqua School District and proximity to a Metro North station, this property will not last! This Two Bed, 1 Bath unit has a great layout with a front and back patio! There are no stairs (just one

Daniel Berger RE/MAX Prestige Properties

309 N Greeley Ave Unit 5C, Chappaqua, NY 10514
$1,350,000

Sold Jul 31, 2026

10 North Ln, Chappaqua, NY 10514
- 3 Beds
- 3 Baths
- 3,155 Sq Ft
- Built 1950
Last Sold Summary
- 3% Below List Price
- $428/SF
- 40 Days On Market
Current Estimated Value $1,382,544

Last Listing Agent Annette Cicinelli Keller Williams Realty Partner

10 North Ln, Chappaqua, NY 10514

Not Listed For Sale

50 Spring Valley Rd, Ossining, NY 10562
- 3 Beds
- 5 Baths
- 3,902 Sq Ft
- Built 1897
50 Spring Valley Rd, Ossining, NY 10562

Last Sold Summary
- 388 Days On Market
Last Listing Agent Michael Clemente DeSimone Real Estate

/39
$2,195,000

Pending
- 6 Beds
- 5.5 Baths
- 6,563 Sq Ft
22 Random Farms Cir, Chappaqua, NY 10514

Set on a picturesque property in sought-after Random Farms, this stunning 6-bedroom residence offers dramatic views, soaring ceilings, and exceptional living spaces designed for both everyday comfort and elegant entertaining. A breathtaking double-height entry welcomes you into sun-drenched interiors featuring walls of windows, rich hardwood floors, and seamless open-concept flow

Sari Shaw Compass Greater NY, LLC

22 Random Farms Cir, Chappaqua, NY 10514
$1,655,800

Sold Apr 21, 2026

9 Whitlaw Ln, Chappaqua, NY 10514
- 4 Beds
- 2.5 Baths
- 2,932 Sq Ft
- Built 1969
Last Sold Summary
- 12% Above List Price
- $565/SF
- 10 Days On Market
Current Estimated Value $1,612,237

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

9 Whitlaw Ln, Chappaqua, NY 10514

Not Listed For Sale

49 Spring Valley Rd, Ossining, NY 10562
- 5 Beds
- 3 Baths
- 2,754 Sq Ft
- Built 1855
49 Spring Valley Rd, Ossining, NY 10562

Last Sold Summary
- 75 Days On Market
Last Listing Agent Matthew Valvano Berkshire Hathaway HS NY Prop

/7
$1,658,995

Pending
- 2 Beds
- 3.5 Baths
- 3,353 Sq Ft
11 Wallace Way Unit 18, Chappaqua, NY 10514

To be Built! Spring 2025 move-in. 3485 square feet ! Still time to personalize interior finishes at our luxury Design Studio. Final building for sale at Chappaqua Crossing! A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor gas fireplace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this

Andrea Martone Houlihan Lawrence Inc.

11 Wallace Way Unit 18, Chappaqua, NY 10514
$1,658,000

Sold Aug 25, 2025

4 Carriage Ln Unit 82, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 3,614 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $459/SF
- 47 Days On Market
Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

4 Carriage Ln Unit 82, Chappaqua, NY 10514

Not Listed For Sale

85 Haights Cross Rd, Chappaqua, NY 10514
- 7 Beds
- 6 Baths
- 6,814 Sq Ft
- Built 1969
85 Haights Cross Rd, Chappaqua, NY 10514

Last Sold Summary
- 43 Days On Market
Last Listing Agent Amy Via Houlihan Lawrence Inc.

/37
$825,000

$265K PRICE DROP
- 3 Beds
- 2.5 Baths
- 3,990 Sq Ft
81 Glendale Rd, Ossining, NY 10562

Fully Available. Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded acres with beautiful stone outcroppings and a few clearings, suitable for chickens, goats and/or horses. The property has rustic outbuildings and walking paths that connect to Teatown trails. This home has large rooms with

Helena Macintyre North Country Sothebys Int Rlt

81 Glendale Rd, Ossining, NY 10562
$752,000

Sold Aug 19, 2025

375 Quaker Rd, Chappaqua, NY 10514
- 3 Beds
- 2.5 Baths
- 2,084 Sq Ft
- Built 1910
Last Sold Summary
- 16% Above List Price
- $361/SF
- 17 Days On Market
Current Estimated Value $829,294

Last Listing Agent Stacy Levey William Raveis-New York, LLC

375 Quaker Rd, Chappaqua, NY 10514

Not Listed For Sale

219 Hamilton Rd, Chappaqua, NY 10514
- 6 Beds
- 4.5 Baths
- 4,692 Sq Ft
- Built 1929
219 Hamilton Rd, Chappaqua, NY 10514

Last Sold Summary
- 11 Days On Market
Last Listing Agent Stacy Levey William Raveis-New York, LLC

/49
$3,599,000

Pending
- 5 Beds
- 6.5 Baths
- 10,594 Sq Ft
301 Whippoorwill Rd, Chappaqua, NY 10514

Timeless elegance meets exceptional craftsmanship in this spectacular brick and stone estate, privately set behind gates on 4+ acres in one of Chappaqua's prestigious Whippoorwill neighborhoods. Designed by acclaimed architect Carol Kurth and masterfully built in 2003 by renowned builder Robert Torre, this extraordinary 5-bedroom, 6 full, 1 half bath residence offers over 10,000 square feet of

Cindy Glynn Compass Greater NY, LLC

301 Whippoorwill Rd, Chappaqua, NY 10514
$1,436,000

Sold Dec 05, 2025

20 Pamela Place, Millwood, NY 10546
- 4 Beds
- 2.5 Baths
- 3,103 Sq Ft
- Built 1971
Last Sold Summary
- 9% Above List Price
- $463/SF
- 14 Days On Market
Current Estimated Value $1,524,844

Last Listing Agent Helen Dorman Houlihan Lawrence Inc.

20 Pamela Place, Millwood, NY 10546

Est $1,710,490

Not Listed For Sale

370 Sarles St, Mount Kisco, NY 10549
- 4 Beds
- 3.5 Baths
- 2,973 Sq Ft
- Built 1908
370 Sarles St, Mount Kisco, NY 10549

Last Sold Summary
- 27 Days On Market
Last Listing Agent Jody Rosen Julia B Fee Sothebys Int. Rlty

/49
$2,250,000
- 4 Beds
- 6 Baths
- 4,340 Sq Ft
82 Shingle House Rd, Millwood, NY 10546

A rare opportunity to create a forever home on nearly 7 private acres in the Chappaqua School District. Rich in history, character and natural beauty, 82 Shingle House Road is a distinctive Millwood estate for the buyer who values land, privacy and potential over cookie-cutter perfection. Originally dating to 1762, the property has evolved over time and offers a unique combination of old-world

Vesna Kanacki Century 21 Elite Realty

82 Shingle House Rd, Millwood, NY 10546
$2,960,000

Sold Dec 26, 2025

93 Haights Cross Rd, Chappaqua, NY 10514
- 4 Beds
- 4.5 Baths
- 6,542 Sq Ft
- Built 1979
Last Sold Summary
- 15% Below List Price
- $452/SF
- 102 Days On Market
Current Estimated Value $3,142,458

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

93 Haights Cross Rd, Chappaqua, NY 10514

Est $2,859,881

Not Listed For Sale

16 Kittle Rd, Chappaqua, NY 10514
- 5 Beds
- 5.5 Baths
- 4,249 Sq Ft
- Built 1936
16 Kittle Rd, Chappaqua, NY 10514

Last Sold Summary
- 13 Days On Market
Last Listing Agent Heather Bouza Compass Greater NY, LLC

/26
$949,000

Pending
- 4 Beds
- 3 Baths
- 3,012 Sq Ft
6 Maria Ln, Ossining, NY 10562

Spacious and beautifully maintained raised ranch set on 2 level acres, offering the perfect combination of comfort, functionality, and flexible living space. This 4 bedroom, 3 full bath home lives like a 5 bedroom and features sun-filled interiors, hardwood floors, and charming brick fireplaces. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring rich

Mark Boyland Keller Williams Realty Partner

6 Maria Ln, Ossining, NY 10562
$525,000

Sold Oct 16, 2025

380 Whippoorwill Rd, Chappaqua, NY 10514
- 3 Beds
- 2 Baths
- 880 Sq Ft
- Built 1927
Last Sold Summary
- 16% Below List Price
- $597/SF
- 61 Days On Market
Current Estimated Value $773,976

Last Listing Agent Sari Shaw Compass Greater NY, LLC

380 Whippoorwill Rd, Chappaqua, NY 10514

Est $1,953,892

Not Listed For Sale

55 Cowdin Cir, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 4,045 Sq Ft
- Built 1952
55 Cowdin Cir, Chappaqua, NY 10514

Last Sold Summary
- 13 Days On Market
Last Listing Agent Eric Stein RE/MAX Distinguished Hms.&Prop

/17
$3,350,000

New Construction Pending
- 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
$799,000

Sold Aug 05, 2026

127 Stone Bridge Square Unit 127, Chappaqua, NY 10514
- 2 Beds
- 2.5 Baths
- 1,244 Sq Ft
- Built 1986
Last Sold Summary
- $642/SF
- 11 Days On Market
Current Estimated Value $799,865

Last Listing Agent Victoria Miller Compass Greater NY, LLC

127 Stone Bridge Square Unit 127, Chappaqua, NY 10514

Est $2,008,269

Not Listed For Sale

70 Cowdin Cir, Chappaqua, NY 10514
- 4 Beds
- 4 Baths
- 3,689 Sq Ft
- Built 1963
70 Cowdin Cir, Chappaqua, NY 10514

Last Sold Summary
- 12 Days On Market
Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

/2
$239,000

$36K PRICE DROP Pending
- Land
- 2.02 Acres
- $118,317 per Acre
181 Somerstown Rd, Millwood, NY 10546

2+ acres of Land in Chappaqua School District. Calling all Buyers that can't find what they're looking for in a single family home...Build Your own home just the way you like! Moments from Shopping, Highways and Schools. Over 150' of frontage. Needs Zoning, Planning, BOH approvals. Get started today. Additional Information: SoilType:Unknown,

Andrea Martone Houlihan Lawrence Inc.

181 Somerstown Rd, Millwood, NY 10546
$865,000

Sold Aug 04, 2026

55 Hoags Cross Rd, Ossining, NY 10562
- 3 Beds
- 2 Baths
- 2,292 Sq Ft
- Built 1964
Last Sold Summary
- 4% Below List Price
- $377/SF
- 57 Days On Market
Current Estimated Value $861,048

Last Listing Agent Maryanne Durr Coldwell Banker Realty

55 Hoags Cross Rd, Ossining, NY 10562

Est $1,751,550

Not Listed For Sale

64 Cowdin Cir, Chappaqua, NY 10514
- 3 Beds
- 2.5 Baths
- 2,911 Sq Ft
- Built 1962
64 Cowdin Cir, Chappaqua, NY 10514

Last Sold Summary
- 14 Days On Market
Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

/6
$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
$1,620,000

Sold Jun 17, 2026

25 Longview Ln, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 3,193 Sq Ft
- Built 1979
Last Sold Summary
- 25% Above List Price
- $507/SF
- 12 Days On Market
Current Estimated Value $1,467,231

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

25 Longview Ln, Chappaqua, NY 10514

Est $1,084,521

Not Listed For Sale

185 Harriman Rd, Mount Kisco, NY 10549
- 3 Beds
- 3 Baths
- 2,609 Sq Ft
- Built 1927
185 Harriman Rd, Mount Kisco, NY 10549

Last Sold Summary
- 6 Days On Market
Last Listing Agent Sonya Cronin Julia B Fee Sothebys Int. Rlty

/14
$299,000

Pending
- 4 Beds
- 2.5 Baths
- 2,374 Sq Ft
5 Maria Ln, Ossining, NY 10562

Opportunity knocks on this exceptionally private, 2+ acre parcel tucked away on a serene street ending with a cul-de-sac in the sought-after Town of New Castle. Whether you are looking to take on a complete top-to-bottom renovation or build the custom home of your dreams, this property offers the perfect foundation and acreage for your vision. While you'll feel worlds away in your own private

Anthony Lando Julia B Fee Sothebys Int. Rlty

5 Maria Ln, Ossining, NY 10562
$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 $1,169,432

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

326 Millwood Rd, Chappaqua, NY 10514

Est $765,564

Not Listed For Sale

10 Birch Dr, Mount Kisco, NY 10549
- 3 Beds
- 1 Bath
- 1,266 Sq Ft
- Built 1930
10 Birch Dr, Mount Kisco, NY 10549

Last Sold Summary
- 71 Days On Market
Last Listing Agent Justin Pieragostini Coldwell Banker Realty

/47
$3,389,000

Pending
- 4 Beds
- 6.5 Baths
- 5,563 Sq Ft
40 Algonquin Dr, Chappaqua, NY 10514

Timeless elegance meets relaxed country chic at this extraordinary Chappaqua retreat. Ideally situated on one of Chappaqua's most coveted streets, this remarkable residence was originally built in 1910 and completely renovated and reimagined in 200l and then again in 2009 for modern living. Privately set amid beautifully landscaped grounds, 40 Algonquin blends classic country manor-style

Kathryn Weinberger Compass Greater NY, LLC

40 Algonquin Dr, Chappaqua, NY 10514
$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 $1,314,792

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

71 Commodore Rd, Chappaqua, NY 10514

Est $870,575

Not Listed For Sale

202 Byram Lake Rd, Mount Kisco, NY 10549
- 2 Beds
- 1.5 Baths
- 1,614 Sq Ft
- Built 1940
202 Byram Lake Rd, Mount Kisco, NY 10549

Last Sold Summary
- 17 Days On Market
Last Listing Agent Mario Sclafani RE/MAX Classic Realty

/27
$1,079,000

$21K PRICE DROP
- 4 Beds
- 3 Baths
- 2,606 Sq Ft
54 Allapartus Rd, Ossining, NY 10562

Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping,

Derek Greene Greene Realty Group

54 Allapartus Rd, Ossining, NY 10562

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