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Explore Similar Homes Within 2 Miles of Pleasantville, NY

  • /35

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,418 Sq Ft

    110 Morningside Dr, Ossining, NY 10562

    Welcome Home and discover this charming ranch-style residence nestled in one of Ossining’s most sought-after neighborhoods. Surrounded by nature and set on nearly an acre (0.85 acres) of beautifully landscaped property, this Single Family home offers comfort with 3 beds and 2 baths, lives like 2,000+ sq/ft with finished Basement, 2+ Car Garage, privacy, and timeless appeal.Enjoy a sun-filled

    Luis Morgado HomeSmart Homes & Estates

    110 Morningside Dr, Ossining, NY 10562
  • /36

    $1,800,000

    • 4 Beds
    • 4 Baths
    • 3,189 Sq Ft

    19 Halsey Place, Valhalla, NY 10595

    Fully Renovated Split-Level in a Top-Rated School District! A Sanctuary of Privacy and Luxury! This meticulously maintained home is the epitome of quality, offering a private oasis surrounded by over 150 mature evergreens. The residence has been transformed into a masterpiece, featuring 4 bedrooms, 4 baths, and a newly added legal 800 sq ft accessory apartment with its own private entrance.

    Peter Sisca Real Broker NY LLC

    19 Halsey Place, Valhalla, NY 10595
  • /22

    $829,900

    • 3 Beds
    • 1.5 Baths
    • 1,673 Sq Ft

    350 Commerce St, Hawthorne, NY 10532

    Step into a beautifully renovated home where modern sophistication and classic charm create an unforgettable first impression, enhanced by its striking blue exterior paired with timeless black shutters (install soon). A large foyer welcomes you in, setting the tone for the thoughtfully updated interior. The dining room is perfectly situated adjacent to the living room, creating an inviting, open

    Lisa Cozzi Westchester Dream Home Realty

    350 Commerce St, Hawthorne, NY 10532
  • /20

    $475,000

    • 1 Bed
    • 1.5 Baths
    • 1,207 Sq Ft

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

    Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two

    Alicja Bohmrich Houlihan Lawrence Inc.

    356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
  • /34

    $999,000

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft

    7 Dunn Ln, Briarcliff Manor, NY 10510

    Located in the beautiful and quaint village of Briarcliff Manor—one of Westchester’s most desirable communities known for its award-winning school district, charming village center, and peaceful suburban character—this exceptional, fully renovated move-in-ready ranch with a finished lower level offers an unmatched blend of modern luxury, single-level living, and walk-to-everything convenience,

    Greg Kochanov Moda Realty LLC

    7 Dunn Ln, Briarcliff Manor, NY 10510
  • /38

    $3,500,000

    • 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
  • /20

    $1,295,000

    • 4 Beds
    • 2.5 Baths
    • 3,700 Sq Ft

    775 Linda Ave, Thornwood, NY 10594

    Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the Mount Pleasant school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an open

    Mary Ann Tighe Houlihan Lawrence Inc.

    775 Linda Ave, Thornwood, NY 10594
  • /46

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,870 Sq Ft

    27 Hardscrabble Rd, Briarcliff Manor, NY 10510

    Presenting a complete interior and exterior renovation in design and construction showcasing contemporary bathrooms and an eat in kitchen with open concept living spaces! BONUS- additional building lot included in sale with separate driveway entrance!An architectural masterpiece in design, curb appeal and privacy for entertaining is showcased by this stunning fully renovated home featuring

    Justin Pieragostini Coldwell Banker Realty

    27 Hardscrabble Rd, Briarcliff Manor, NY 10510
  • /13

    $1,985,000

    • 4 Beds
    • 2.5 Baths
    • 4,500 Sq Ft

    0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514

    Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an

    Rachel Lacoste Houlihan Lawrence Inc.

    0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514
  • /2

    $1,695,000

    • 4 Beds
    • 3.5 Baths
    • 3,525 Sq Ft

    00 Belleview Ave, Thornwood, NY 10594

    Make your dream a reality with this to be built home in the quiet hamlet of Thornwood. This Colonial offers 4 spacious bedrooms, 3.5 baths and an ideal layout for today’s lifestyle. The main level features a bright living room, a formal dining room and a beautifully appointed kitchen complete with a center island, dining area and direct access to the deck—ideal for outdoor dining while enjoying

    Rita Longo Howard Hanna Rand Realty

    00 Belleview Ave, Thornwood, NY 10594
  • /44

    $2,299,000

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

    22 Carriage Ln, Chappaqua, NY 10514

    Introducing a stunning, contemporary, brand-new, lavish, luxury townhouse at sold-out Chappaqua Crossings. This coveted end unit sits on an ultra-premium lot with exquisite, wooded views and privacy on all three sides. Designed for discerning modern living, this home features a first-floor primary suite, rooftop deck with outdoor kitchen, and a fully finished basement with gym/media room, wet bar

    Daniel Ansell JLJ Realty

    22 Carriage Ln, Chappaqua, NY 10514
  • /49

    $1,499,000 Coming Soon

    • 3 Beds
    • 3.5 Baths
    • 3,482 Sq Ft

    44 Elm Rd, Briarcliff Manor, NY 10510

    Set on .94 acres of beautifully landscaped, level property, this exceptional 3-bedroom, 3.5-bath Briarcliff home offers 3,482 sq. ft. of thoughtfully updated living space and an inviting blend of comfort, style, and modern convenience. A welcoming entrance hallway opens to sun-filled rooms with gleaming wood flooring, including a stunning living room with vaulted ceilings, remote skylight shades,

    Suzan Zeolla Houlihan Lawrence Inc.

    44 Elm Rd, Briarcliff Manor, NY 10510
  • /35

    $3,450,000

    • 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
  • /21

    $1,099,000

    • 3 Beds
    • 2 Baths
    • 1,776 Sq Ft

    10 Barnes Ln, Chappaqua, NY 10514

    Move right into this beautifully updated three bedroom, two bathroom ranch, perfectly situated within the award-winning Chappaqua school district. Thoughtfully renovated from top to bottom, this home offers modern comfort and timeless charm. The heart of the home is the stylish kitchen featuring classic oak cabinetry, sleek quartz countertops, and ample space for cooking and entertaining. Both

    Alexander Marks William Raveis-New York LLC

    10 Barnes Ln, Chappaqua, NY 10514
  • /21

    $2,850,000

    • 4 Beds
    • 7 Baths
    • 5,536 Sq Ft

    211 Bedford Rd, Chappaqua, NY 10514

    Exciting and new state-of-the-art expansion and renovation by highly recognized local developer, Tavo Development teaming with noted architect Teo Seguenza. Ready for occupancy in Spring 2026. Meticulous attention to detail, years of experience and master craftsmanship are combined in this new offering, encompassing 5,536 sq ft, 4 bedrooms, 5 full and 2 half baths, a finished walk-out lower level

    Brian Milton Compass Greater NY, LLC

    211 Bedford Rd, Chappaqua, NY 10514
  • /37

    $849,000

    • 3 Beds
    • 2.5 Baths
    • 2,123 Sq Ft

    14 Aspen Way, Thornwood, NY 10594

    AO 12/12/25, contracts out CTS. Location, location! This Split-level home is nestled in a private setting within the desirable "Rolling Hills" neighborhood, on a quiet cul-de-sac. As you enter you will notice the spacious eat-in kitchen that flows effortlessly into the dining area and living room. Great potential to make this your forever home! The garage has a door out to the yard. The hallway

    Jeanne Beckley Howard Hanna Rand Realty

    14 Aspen Way, Thornwood, NY 10594
  • /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
  • /50

    $1,790,000

    • 3 Beds
    • 3.5 Baths
    • 2,956 Sq Ft

    21 Pheasant Dr, Armonk, NY 10504

    Completely renovated from top to bottom, 21 Pheasant Drive in Armonk has been transformed into a stunning modern home offering luxury, comfort, and flexibility. This beautifully redesigned residence features 3 spacious bedrooms plus a dedicated home office, along with 3.5 brand-new baths finished with high-end materials. The finished attic provides an incredible bonus space—perfect as a private

    Jian Gonzalez RE/MAX Opulent

    21 Pheasant Dr, Armonk, NY 10504
  • /31

    $699,995

    • 3 Beds
    • 1.5 Baths
    • 1,360 Sq Ft

    136 Harriman Rd, Mount Kisco, NY 10549

    Welcome to 136 Harriman Road, Mount Kisco, New York!This charming and fully updated three-bedroom, one-and-a-half-bath home sits on 1.4 acres in the highly sought-after Town of New Castle. Thoughtfully renovated throughout, it perfectly blends classic charm with modern finishes. Inside, you’ll find fully renovated bathrooms, brand-new interior and exterior doors, updated LED lighting with

    Carolina Pelaez Coldwell Banker Realty

    136 Harriman Rd, Mount Kisco, NY 10549
  • /37

    $12,000,000

    • 5 Beds
    • 5.5 Baths
    • 7,538 Sq Ft

    48 Raafenberg Rd, Tarrytown, NY 10591

    Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central

    David Turner Compass Greater NY, LLC

    48 Raafenberg Rd, Tarrytown, NY 10591
  • /26

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    237 Brady Ave, Hawthorne, NY 10532

    Newly renovated 3-bedroom, 2-bath single-family home—a perfect blend of modern style, smart design, and everyday comfort. New Hardwood Oak floors. The thoughtfully designed layout allows for an abundance of natural light, creating a warm and welcoming atmosphere in every room. The spacious living area is ideal for both relaxing and entertaining, while the open-concept kitchen features stylish

    Sokol Biberaj Century 21 Dawns Gold Realty

    237 Brady Ave, Hawthorne, NY 10532
  • /27

    $699,900

    • 3 Beds
    • 1.5 Baths
    • 1,736 Sq Ft

    65 Westlake Dr, Thornwood, NY 10594

    Wonderful split style that shows like a four bedroom. Home features hardwood floors throughout, living room with vaulted ceilings, formal dining room, eat in kitchen with door out to patio and private rear yard, large family room in the lower level. The possibilities are endless and with a little effort and modifications can make this home your own. Set in a convenient location and close to

    Robert Mulvey William Raveis Real Estate

    65 Westlake Dr, Thornwood, NY 10594
  • /32

    $1,195,222

    • 3 Beds
    • 3 Baths
    • 3,328 Sq Ft

    517 Old Chappaqua Rd, Briarcliff Manor, NY 10510

    Beautifully updated contemporary colonial in a private, wooded setting! Set well back from the road and surrounded by a rustic natural landscape, this home offers a spacious, open floor plan with high ceilings, hardwood floors, and stylish modern updates throughout. The renovated kitchen features stainless steel appliances, a double wall oven, cooktop, cherry cabinetry, wine rack, and granite

    Mark Seiden Mark Seiden Real Estate Team

    517 Old Chappaqua Rd, Briarcliff Manor, NY 10510
  • /43

    $1,599,999

    • 5 Beds
    • 3.5 Baths
    • 4,714 Sq Ft

    345 Elm Rd, Briarcliff Manor, NY 10510

    Welcome to 345 Elm Road, a beautifully appointed Briarcliff Manor home for sale offering exceptional space, comfort, and craftsmanship throughout—ideally situated within walking distance to the Village of Briarcliff Manor, close to restaurants, parks, village recreation (including pool, tennis, and playground), shopping, and minutes to the Metro-North train, major highways, and an easy NYC

    Suzan Zeolla Houlihan Lawrence Inc.

    345 Elm Rd, Briarcliff Manor, NY 10510
  • /17

    $599,000

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft

    150 Bedford Rd Unit 12A, Chappaqua, NY 10514

    Welcome to this move-in-ready 2-bedroom, 2-bath residence in highly sought-after Chappaqua Commons. Recently refreshed with thoughtful updates throughout, this sun-filled home combines modern finishes with effortless convenience.The spacious open-concept living and dining area features brand-new flooring (2025) and a seamless flow to the updated kitchen, boasting new countertops and

    Sari Shaw Compass Greater NY, LLC

    150 Bedford Rd Unit 12A, Chappaqua, NY 10514

Home Trends in Pleasantville, NY

Housing Trends

Median Sale Price
$872,500
Median Single Family Sale Price
$857,500
Median Townhouse Sale Price
$1,400,000
Median 2 Bedroom Sale Price
$574,500
Median 1 Bedroom Sale Price
$447,500
Average Price Per Sq Ft
$491
Number of Homes for Sale
2
Last 12 months Home Sales
68
Months of Supply
0.40
Median List Price
$844,000
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
-7%
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