26

New Castle, NY Homes for Sale with Acreage

Section Image Section Image
  • /49

    $3,500,000

    • 10 Beds
    • 5.5 Baths
    • 8,881 Sq Ft

    335 Croton Dam Rd, Ossining, NY 10562

    Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing

    Agent Photo

    Hillary Landau

    Compass Greater NY, LLC

    335 Croton Dam Rd, Ossining, NY 10562
  • /23

    $989,000

    $56K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,581 Sq Ft

    10 Horseshoe Rd, Mount Kisco, NY 10549

    Best value in the Award Winning Chappaqua School District! Set on an acre in the desirable Rolling Fields neighborhood, this well maintained home offers comfortable living with a flexible layout that lives larger than its 3-bedroom configuration. Updated in 2013 with, new roof, new windows, new mechanicals, kitchen and bath renovations. The main level features an inviting kitchen with stainless

    Agent Photo

    Deena Bouchier

    Compass Greater NY, LLC

    10 Horseshoe Rd, Mount Kisco, NY 10549
  • /46

    $1,095,000

    $105K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,867 Sq Ft

    27 Allapartus Cir, Ossining, NY 10562

    This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning

    Agent Photo

    Mary Stetson

    Stetson Real Estate

    27 Allapartus Cir, Ossining, NY 10562
  • /34

    $1,188,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 3,953 Sq Ft

    11 Kitchel Rd, Mount Kisco, NY 10549

    Smartly updated, multi-level home offers room for everyone. Living room with wood-burning fireplace. Transom windows frame the entries to the thoughtfully designed eat-in kitchen with wood cabinetry, Miele induction cooktop and in-wall convection oven, Bosch refrigerator/freezer and dishwasher, GE microwave and granite counter tops, which adjoins the family room with slider to the deck on one

    Stacy Levey William Raveis-New York, LLC

    11 Kitchel Rd, Mount Kisco, NY 10549
  • /50

    $2,699,000

    • 4 Beds
    • 4.5 Baths
    • 5,918 Sq Ft

    40 Hamilton Dr, Chappaqua, NY 10514

    Tucked away on over two exquisitely landscaped acres in one of Chappaqua’s most prestigious enclaves, this exceptional newly constructed modern home redefines luxury living through a masterful blend of architectural sophistication, cutting-edge efficiency, and timeless elegance. Designed with a discerning eye and crafted with uncompromising quality, this magazine-worthy residence offers the

    Matthew Valvano Berkshire Hathaway HS NY Prop

    40 Hamilton Dr, Chappaqua, NY 10514
  • /48

    $1,998,999

    • 4 Beds
    • 3.5 Baths
    • 3,124 Sq Ft

    4 Old House Ln, Chappaqua, NY 10514

    Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North. Thoughtfully

    Laura Lulgjuraj Houlihan Lawrence Inc.

    4 Old House Ln, Chappaqua, NY 10514
  • /9

    $2,895,000

    • 4 Beds
    • 5.5 Baths
    • 4,589 Sq Ft

    39 Barnes Ln, Chappaqua, NY 10514

    Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion this Fall 2026. Early buyers will have the rare chance to customize many of the final finishes and tailor the home to their personal style. This thoughtfully designed home offers 4 bedrooms and 5.1 bathrooms, with a highly desirable layout that lives

    Karin Kimtis Compass Greater NY, LLC

    39 Barnes Ln, Chappaqua, NY 10514
  • /30

    $1,050,000

    • 3 Beds
    • 3 Baths
    • 2,160 Sq Ft

    568 Saw Mill River Rd, Millwood, NY 10546

    Private access to the scenic North County Trailway, offering miles of paved trails for walking, running, and biking, is just one of the many highlights of this beautifully maintained home. Not to be missed, this sun-filled 3-bedroom, 3-bath raised ranch offers a comfortable layout ideal for both everyday living and entertaining. Set privately on over 1.3 level acres and screened from the road by

    Stacey Sporn William Raveis Real Estate

    568 Saw Mill River Rd, Millwood, NY 10546
  • /39

    $1,995,000

    • 4 Beds
    • 3 Baths
    • 3,288 Sq Ft

    12 Brandon Dr, Mount Kisco, NY 10549

    Nestled on a picturesque tree-lined street in the highly sought-after Chappaqua School District, this beautifully renovated 4-bedroom Colonial combines timeless charm with thoughtfully updated living spaces. A welcoming front porch offers the perfect place to enjoy a quiet morning coffee or relax on a summer evening. A gracious entry foyer introduces the home's warm and inviting interior. The

    Cindy Glynn Compass Greater NY, LLC

    12 Brandon Dr, Mount Kisco, NY 10549
  • /27

    $579,000

    • 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
  • /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
  • /49

    $3,599,000

    • 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
  • /6

    $2,250,000

    Coming Soon
    • 4 Beds
    • 6 Baths
    • 4,340 Sq Ft

    82 Shingle House Rd, Millwood, NY 10546

    A rare opportunity to own a private mini-estate on approximately 6.9 acres in Millwood. The main residence offers four bedrooms, three-and-a-half baths and generous living spaces with views of the property’s natural surroundings. Highlights include an eat-in country kitchen with French marble flooring, a living room overlooking the pond and waterfall, multiple fireplaces, radiant heat in the

    Vesna Kanacki Century 21 Elite Realty

    82 Shingle House Rd, Millwood, NY 10546
  • /27

    $1,085,000

    $15K 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
  • /27

    $49,500,000

    • 8 Beds
    • 10 Baths
    • 26,079 Sq Ft

    Unlisted Address

    ONE OF NEW YORK'S MOST COVETED ESTATES. Enter a world where timeless elegance meets state-of-the-art luxury. Originally built in 1901 for renowned financier J. Borden Harriman, this legendary estate - historically known as Devonshire, and earlier as Uplands - stands as a rare example of Gilded Age grandeur, reimagined for modern living. Over its long history, the estate has been owned by some of

    Brian Sheerin William Raveis-New York LLC

    Unlisted Address
  • /40

    $1,399,000

    • 3 Beds
    • 4 Baths
    • 3,140 Sq Ft

    22 Garey Dr, Chappaqua, NY 10514

    Perched on a lushly landscaped acre and thoughtfully expanded, offering a comforting blend of function, space, and versatility for today’s lifestyle, whether working from home (the main-level office opens to a private deck, creating a delightful setting for morning coffee or an inspiring workday), entertaining (the spacious living room with fireplace adjoins the formal dining room with sliding

    Stacy Levey William Raveis-New York, LLC

    22 Garey Dr, Chappaqua, NY 10514
  • /50

    $3,100,000

    • 5 Beds
    • 5.5 Baths
    • 7,238 Sq Ft

    2 Heathcote Dr, Mount Kisco, NY 10549

    Privately gated and masterfully crafted, this exceptional custom brick estate is a showcase of timeless elegance and grand-scale living, nestled on over two acres in the heart of Chappaqua. Beyond the cobblestone apron and curbing, a sweeping driveway leads to a residence designed for both luxury and comfort, boasting soaring 10-foot ceilings, four stately fireplaces, exquisite architectural

    Gino Bello Howard Hanna Rand Realty

    2 Heathcote Dr, Mount Kisco, NY 10549
  • /50

    $1,750,000

    $150K PRICE DROP
    • 9 Beds
    • 8 Baths
    • 5,337 Sq Ft

    51 Pinesbridge Rd, Ossining, NY 10562

    Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities.The beautifully renovated 5,337-square-foot Main House features 5 spacious

    Cathy DeBow William Raveis Real Estate

    51 Pinesbridge Rd, Ossining, NY 10562
  • /35

    $2,990,000

    $687K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 8,200 Sq Ft

    20 Bessel Ln, Chappaqua, NY 10514

    Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

    Tianying Xu Houlihan Lawrence Inc.

    20 Bessel Ln, Chappaqua, NY 10514
  • /50

    $3,100,000

    • 3 Beds
    • 5 Baths
    • 6,091 Sq Ft

    23 Inningwood Rd, Ossining, NY 10562

    No words or photos will justify the Magical beauty of this luxurious home. The woodwork in this custom built home was done by craftsman Mark Pedley, a very talented carpenter/joiner from Vermont who previously worked in Palaces in Jordan. The home is flawless and impeccable with spa like bathrooms, a gourmet kitchen, outdoor grilling area, sauna, steam bath and jacuzzi, with marble, granite and

    Dee Rabady Woodfront Realty, Inc.

    23 Inningwood Rd, Ossining, NY 10562
  • /20

    $1,665,000

    $85K PRICE DROP
    • Land
    • 12.92 Acres
    • $128,870 per Acre

    767 King St, Chappaqua, NY 10514

    Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park,

    Sena Baron William Raveis-New York, LLC

    767 King St, Chappaqua, NY 10514
  • /37

    $3,900,000

    • 4 Beds
    • 5.5 Baths
    • 9,284 Sq Ft

    16 Taylor Rd, Mount Kisco, NY 10549

    Designed without compromise and executed to perfection, this custom Georgian Colonial by Nasser Nakib Architect sets a new standard for luxury living. Eleven-foot ceilings, an effortless open layout, and walls of windows create a light-filled, airy feel throughout. A front-to-back foyer with floating staircase makes a striking first impression, while wide plank wood floors, a slate roof, and full

    Kimberly Zwickel Houlihan Lawrence Inc.

    16 Taylor Rd, Mount Kisco, NY 10549
  • /38

    $2,900,000

    $600K PRICE DROP
    • 7 Beds
    • 7 Baths
    • 5,502 Sq Ft

    83 Somerstown Rd, Ossining, NY 10562

    Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country

    Dalia Valdes Julia B Fee Sothebys Int. Rlty

    83 Somerstown Rd, Ossining, NY 10562
  • /6

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 2,682 Sq Ft

    94 Somerstown Rd, Ossining, NY 10562

    Phase Two at Moradia is now offering a fabulous to-be-built new modern on Lot One. Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is a brand-new community of high-end residences. Located along a picturesque road in historic Ossining, NY, each home is set on a beautiful parcel of virgin land. The homesites are elevated

    David Turner Compass Greater NY, LLC

    94 Somerstown Rd, Ossining, NY 10562
  • /6

    $1,899,000

    • 4 Beds
    • 3.5 Baths
    • 2,693 Sq Ft

    94 Somerstown Rd, Ossining, NY 10562

    Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is abrand-new community of to-be-built, high-end residences. Located along a picturesque road in historic Ossining, NY, each home is set on a beautiful parcel of virgin land. The homesites are elevated and private-ranging between 1 1/2 and 3 acres. Masia, is the first

    David Turner Compass Greater NY, LLC

    94 Somerstown Rd, Ossining, NY 10562
  • /5

    $995,000

    • Land
    • 6.46 Acres
    • $154,025 per Acre

    94 Somerstown Rd, Ossining, NY 10562

    Site plan approved subdivision on historic Somerstown road in Ossining. Three lots each with a beautiful building site being all sold together. Roughed in driveway will become common drive to three homesites. Great opportunity to build.

    David Turner Compass Greater NY, LLC

    94 Somerstown Rd, Ossining, NY 10562
How to Buy a Home How to Finance a Home How to Sell a Home