Pleasantville, NY Homes

Est $411,158 Not Listed For Sale
- 1 Bed
- 1 Bath
- 750 Sq Ft
580 Bedford Rd Unit 16, Pleasantville, NY 10570

580 Bedford Rd Unit 16, Pleasantville, NY 10570

Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/40
$1,425,000 Pending
- 4 Beds
- 2.5 Baths
- 3,800 Sq Ft
306 Mountain Rd, Pleasantville, NY 10570

Welcome to Pleasantville! This spectacular Center Hall Colonial combines timeless elegance with modern updates and exceptional quality throughout. Featuring four generously sized bedrooms, this meticulously maintained home offers space, comfort, and style at every turn. Step into the updated chef’s kitchen, beautifully appointed with granite countertops, stainless steel appliances, and a cozy

SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

306 Mountain Rd, Pleasantville, NY 10570
$1,425,000 Sold Aug 08, 2025
- 3,456 Sq Ft
- $412/SF
- 7 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1984
4 Watch Hill Rd, Pleasantville, NY 10570

Unlock the potential of this spacious 4-bedroom home, offering 3,500 sq ft of living space on nearly an acre of serene, private land. This is your opportunity to customize and create your dream home in the highly desirable Byram Hills School District. Enjoy endless possibilities with an in-ground pool, charming gazebo, and expansive yard—perfect for entertaining or relaxing in your own backyard

Maura Mcspedon William Raveis Real Estate

4 Watch Hill Rd, Pleasantville, NY 10570

Est $378,805 Not Listed For Sale
- 1 Bed
- 1 Bath
- 775 Sq Ft
33 Roselle Ave Unit L, Pleasantville, NY 10570

33 Roselle Ave Unit L, Pleasantville, NY 10570

/13
$1,249,000 Pending
- 3 Beds
- 2.5 Baths
- 2,900 Sq Ft
133 Lake Shore Dr, Pleasantville, NY 10570

Don’t miss the chance to create your perfect home! This modern young colonial, is currently under construction by an experienced builder, offers a unique opportunity to tailor the design to your preferences. There is still time to customize! Currently under construction, frame, windows, siding, and plumbing is completed. Built with high-quality materials, including Andersen 400 Series windows and

Natalia Wixom Compass Greater NY, LLC

133 Lake Shore Dr, Pleasantville, NY 10570
$965,000 Sold Aug 08, 2025
- 3,000 Sq Ft
- $322/SF
- 130 Days On Market
- 6 Beds
- 4 Baths
- Built 1918
41 Saratoga Ave, Pleasantville, NY 10570

Incredible opportunity in Mount Pleasant! Yes! It’s TWO Investment properties on ONE Lot! The front house holds the first Unit which is a 3-bed, 1-bath first-floor unit featuring a spacious living room, and kitchen. Open Kitchen just recently renovated. Hardwood floors throughout, bright natural lighting, and a newly tiled kitchen floor. Enjoy the convenience of the downstairs storage and

Christine Ricci Keller Williams NY Realty

41 Saratoga Ave, Pleasantville, NY 10570

Est $2,266,987 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 5,298 Sq Ft
4 Old Farm Rd S, Pleasantville, NY 10570

4 Old Farm Rd S, Pleasantville, NY 10570

/39
$1,050,000 Open Sun 12PM - 3PM
- 4 Beds
- 2.5 Baths
- 3,160 Sq Ft
2 Cecilia Ln, Pleasantville, NY 10570

Modern convenience meets the tranquility of nature in this mid-century inspired retreat. Set on 1.04 acres, this 3,160 SF contemporary home blends privacy, clean lines, and seamless indoor-outdoor living. Expansive Marvin windows, vaulted ceilings with skylights, exposed beams, and a sunken living room connect every space to the outdoors. Multiple decks invite you to read, bird watch, or simply

Kim Tromba Keller Williams Prestige Prop

2 Cecilia Ln, Pleasantville, NY 10570
$1,020,000 Sold Aug 07, 2025
- 2,100 Sq Ft
- $486/SF
- 23 Days On Market
- 3 Beds
- 2 Baths
- Built 1963
80 Oak Ridge Rd, Pleasantville, NY 10570

This meticulously maintained ranch-style home offers a harmonious blend of comfort and style. Boasting 3 spacious bedrooms and 2 full bathrooms, this residence provides ample space for both relaxation and entertainment. Main level features living room, dining room and remodeled kitchen equipped with new stainless steel appliances, granite counter tops, tiled backsplash and convenient

Michael Arcidiacono ERA Insite Realty Services

80 Oak Ridge Rd, Pleasantville, NY 10570

Est $1,172,538 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,570 Sq Ft
20 Brook Manor, Pleasantville, NY 10570

20 Brook Manor, Pleasantville, NY 10570

/33
$799,999
- 4 Beds
- 2 Baths
- 1,690 Sq Ft
23 Brookside Place, Pleasantville, NY 10570

Welcome to 23 Brookside Place in Pleasantville, NY — a beautifully maintained, energy-efficient home set on three tax lots with room to expand. The main level offers timeless details including crown and baseboard molding, a spacious entry foyer with coat closet, and a bright living room featuring recessed lighting and a wood-burning fireplace with wood mantle and stone surround. The updated

Suzan Zeolla Houlihan Lawrence Inc.

23 Brookside Place, Pleasantville, NY 10570
$975,000 Sold Aug 06, 2025
- 2,000 Sq Ft
- $488/SF
- 11 Days On Market
- 3 Beds
- 2 Baths
- Built 1815
22 Church St, Pleasantville, NY 10570

Step into timeless elegance at 22 Church Street, Pleasantville, NY—a completely renovated Colonial masterpiece. This home seamlessly blends classic charm with modern sophistication, offering an exquisite living experience. Nestled on an expansive 11,761-square-foot level lot, this residence boasts three spacious bedrooms and two meticulously updated bathrooms, ensuring comfort and style. In the

Joseph Lukic Compass Greater NY, LLC

22 Church St, Pleasantville, NY 10570

Est $1,751,910 Not Listed For Sale
- 5 Beds
- 8 Baths
- 4,551 Sq Ft
96 Deerfield Ln N, Pleasantville, NY 10570

96 Deerfield Ln N, Pleasantville, NY 10570

/46
$685,000
- 2 Beds
- 2 Baths
- 1,297 Sq Ft
60 Foxwood Dr Unit 2, Pleasantville, NY 10570

Beautiful Foxwood Condominium.. Picturesque Country Setting with Meticulously Kept Grounds.. Rarely Offered, Foxwood's 1st Floor " Somerset " Model.. Approximately 1,300 sq ft of 1 Level Living.. Light and Bright in the Most Private of Locations with Southern - Western Exposure and Wooded Views.. Eat in Kitchen with Large Dining Area, Additional Cabinetry and Plenty of Counter Space Throughout..

Vincent Vetrano Douglas Elliman Real Estate

60 Foxwood Dr Unit 2, Pleasantville, NY 10570
$2,310,000 Sold Aug 04, 2025
- 4,771 Sq Ft
- $484/SF
- 4 Days On Market
- 5 Beds
- 6 Baths
- Built 1984
19 Trapping Way, Pleasantville, NY 10570

Welcome Home! This meticulously maintained 5-bedroom Colonial is located in The Estates, in one of the most sought-after school districts Byram Hills School. Set on a beautifully landscaped, level corner lot just under an acre, the property offers both privacy and space—perfect for relaxing or entertaining. The first floor features a chef’s kitchen that opens to a spacious great room, along with

Stacey Sporn William Raveis Real Estate

19 Trapping Way, Pleasantville, NY 10570

Est $1,514,191 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,853 Sq Ft
23 Heritage Dr, Pleasantville, NY 10570

23 Heritage Dr, Pleasantville, NY 10570

/35
$535,000
- 2 Beds
- 1.5 Baths
- 1,036 Sq Ft
9 Tudor Ct Unit 4, Pleasantville, NY 10570

This Spacious 2 Bedroom, 1 1/2 Bath Foxwood Condominium is located in a very quiet location. Surrounded by beautiful trees and landscaping makes this a desirable location within the complex. This first floor Linacre Unit has a lovely patio with easy access to the yard. The Foxwood Complex is meticulously maintained at all times and is very desirable with amenities including pool, adjacent

Mary Ann Mancini Howard Hanna Rand Realty

9 Tudor Ct Unit 4, Pleasantville, NY 10570
$905,000 Sold Aug 04, 2025
- 2,168 Sq Ft
- $417/SF
- 42 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1965
52 Seneca Ln, Pleasantville, NY 10570

Do not miss this lovely three-bedroom, two-and-a-half-bath, tastefully appointed and renovated cozy home. Located on a serene cul-de-sac, yet just a short stroll from the lively village center with great community spirit, and the proximity to a public swimming pool. The home also sits right next to the golf course, offering sweeping views of the lush natural greens. Enjoy the perfect balance of

Denis Knox Howard Hanna Rand Realty

52 Seneca Ln, Pleasantville, NY 10570

Est $1,732,627 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,518 Sq Ft
118 Deerfield Ln N, Pleasantville, NY 10570

118 Deerfield Ln N, Pleasantville, NY 10570

/35
$899,000
- 3 Beds
- 1.5 Baths
- 1,770 Sq Ft
55 Sarles Ln, Pleasantville, NY 10570

Welcome to your slice of Pleasantville—where small-town charm meets everyday convenience. This 3-bedroom, 1.5-bath Craftsman-style home offers warmth, character, and a lifestyle that’s hard to resist. Start your mornings on the classic front porch, then head to the local Saturday farmers market just a short stroll away for fresh produce and friendly faces. Inside, the vintage kitchen features

Vanessa Catalano Julia B Fee Sothebys Int. Rlty

55 Sarles Ln, Pleasantville, NY 10570
$920,000 Sold Aug 04, 2025
- 1,766 Sq Ft
- $521/SF
- 63 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1973
80 Madison Ave, Pleasantville, NY 10570

Welcome home to this immaculate colonial, perfectly nestled at the end of a peaceful street for ultimate privacy. Thoughtfully designed and impeccably maintained, this home offers a blend of classic charm and modern comfort. Step inside to discover an inviting open-concept kitchen connected to the outside covered deck and dining area, perfect for both casual meals and entertaining. The spacious

James Campbell Houlihan Lawrence Inc.

80 Madison Ave, Pleasantville, NY 10570

Est $1,638,000 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,374 Sq Ft
114 Deerfield Ln N, Pleasantville, NY 10570

114 Deerfield Ln N, Pleasantville, NY 10570

/21
$239,000
- 1 Bed
- 1 Bath
- 720 Sq Ft
70 Manville Rd Unit 2, Pleasantville, NY 10570

Welcome to this beautifully maintained one-bedroom co-op offering an abundance of natural light and classic charm in sought-after Pleasantville, NY. This bright and airy home features hardwood floors throughout, a spacious living area, and a well-proportioned bedroom—perfect for comfortable everyday living. Ideally situated less than one mile from the center of town and the Metro-North train

Tom Consaga RE/MAX Ace Realty

70 Manville Rd Unit 2, Pleasantville, NY 10570
$1,875,000 Sold Aug 01, 2025
- 4,983 Sq Ft
- $376/SF
- 72 Days On Market
- 8 Beds
- 7 Baths
- Built 1916
22 Clark St, Pleasantville, NY 10570

Discover the perfect blend of classic charm and modern versatility in this impressive Colonial home, ideally located in the picturesque town of Pleasantville. Exterior siding and trim has been completely painted and repaired and new roof installed in 2022! This expansive residence offers not only six spacious bedrooms but also features a two bedroom accessory apartment above a detached garage,

Imma Carletto Christie's Int. Real Estate

22 Clark St, Pleasantville, NY 10570

Est $1,543,359 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,245 Sq Ft
5 Heritage Dr, Pleasantville, NY 10570

5 Heritage Dr, Pleasantville, NY 10570

/50
$1,899,000
- 4 Beds
- 3.5 Baths
- 3,917 Sq Ft
29 Cedar Ln, Pleasantville, NY 10570

Welcome to your dream home nestled in the serene cul-de-sac of Pleasantville. This stunning 4-bedroom, 4-bathroom residence spans an impressive 3917 square feet, offering luxurious living with a touch of modern elegance. Step inside to discover a home that was rebuilt in 2023 and designed by local architect Tim Lener. A beautiful open floor plan adorned with exquisite wood floors that flow

Karen O'Connor Compass Greater NY, LLC

29 Cedar Ln, Pleasantville, NY 10570
$800,000 Sold Jul 30, 2025
- 2,508 Sq Ft
- $319/SF
- 42 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1975
570 Manville Rd, Pleasantville, NY 10570

You found this shining gem in Pleasantville! Well maintained expanded Raised Ranch within walking distance of train station! 5 bedrooms, 3.5 bath home offers 2,508 sq ft of living space! Formal living room, large eat-in kitchen, formal dining room, & convenient hall bathroom. This home has a main level master suite & 2 large additional bedrooms. Finished lower level offers a large living room,2

Peter Procino Coldwell Banker Realty

570 Manville Rd, Pleasantville, NY 10570

Est $778,187 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,655 Sq Ft
161 Lake Shore Dr, Pleasantville, NY 10570

161 Lake Shore Dr, Pleasantville, NY 10570

/13
$564,000
- 1 Bed
- 1.5 Baths
- 1,056 Sq Ft
9 Foxwood Dr Unit 4, Pleasantville, NY 10570

Sophistication meets comfort at this stunning Tudor-style residence in the highly sought-after Foxwood community. One of the largest units in the complex, this sun-drenched home offers a gracious layout with one spacious bedroom, a versatile office/guest room, and 2 beautifully appointed baths. Expansive windows flood the living spaces with natural light, highlighting elegant finishes and

Laurie Correia Houlihan Lawrence Inc.

9 Foxwood Dr Unit 4, Pleasantville, NY 10570
$850,000 Sold Jul 28, 2025
- 2,144 Sq Ft
- $396/SF
- 14 Days On Market
- 4 Beds
- 2 Baths
- Built 1949
55 Leland Ave, Pleasantville, NY 10570

Nestled on a quiet cul-de-sac in the desirable Village of Pleasantville, this lovingly maintained home is on the market for the first time in nearly 50 years. Brimming with curb appeal and just steps away from the Village pool and park, 55 Leland Avenue offers the perfect blend of charm, comfort, and convenience.Step inside to a spacious living room featuring a classic wood-burning

Maura Mcspedon William Raveis Real Estate

55 Leland Ave, Pleasantville, NY 10570

Est $1,158,667 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,936 Sq Ft
311 Bear Ridge Rd, Pleasantville, NY 10570

311 Bear Ridge Rd, Pleasantville, NY 10570

/43
$977,700
- 3 Beds
- 2 Baths
- 1,695 Sq Ft
290 Mountain Rd, Pleasantville, NY 10570

Modern Living Meets Natural Beauty in the Heart of Pleasantville. Perched above the charming village of Pleasantville, this modern masterpiece has been completely rebuilt from the ground up, offering a one-of-a-kind blend of contemporary design and character. Set on nearly three-quarters of an acre, the home offers privacy and serenity—yet is located under a mile from Metro North, with express

Matthew Valvano Berkshire Hathaway HS NY Prop

290 Mountain Rd, Pleasantville, NY 10570
$865,000 Sold Jul 25, 2025
- 1,698 Sq Ft
- $509/SF
- 18 Days On Market
- 4 Beds
- 2 Baths
- Built 1965
38 Bedford Rd, Pleasantville, NY 10570

Welcome to 38 Bedford Road! Move right into this beautifully, renovated 4 bedroom, 2 bathroom home, conveniently located between the Towns of Pleasantville and Chappaqua, local conveniences and major roadways. The main level features an open concept Living / Dining with hardwood floors, and lots of natural light. Just off the living room is a comfortable outdoor deck that leads to a private,

Deborah Hilfman RE/MAX Prestige Properties

38 Bedford Rd, Pleasantville, NY 10570

Est $1,738,486 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 6,677 Sq Ft
245 Bear Ridge Rd, Pleasantville, NY 10570

245 Bear Ridge Rd, Pleasantville, NY 10570

/45
$965,000
- 5 Beds
- 4 Baths
- 2,916 Sq Ft
27 Bedford Rd, Pleasantville, NY 10570

Set in the desirable Village of Pleasantville, this enchanting Colonial home, built in 1830 and sited on .78 acres, offers timeless character, unique architectural details, and endless potential. A true diamond in the rough, this residence, dubbed "Pierce House", is ready to be transformed into something truly spectacular. Far from cookie-cutter, this home tells a story. With its original charm

Grace LoBello William Raveis Real Estate

27 Bedford Rd, Pleasantville, NY 10570
$1,550,000 Sold Jul 25, 2025
- 3,491 Sq Ft
- $444/SF
- 8 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1987
184 Deerfield Ln N, Pleasantville, NY 10570

Step into timeless elegance with this stately colonial in a highly desirable neighborhood. The grand two-story entry welcomes you and bathes the home in natural sunlight. High ceilings, skylights, expansive windows and the beautiful flow enhance every inch of this home.The step-down living room is flooded with natural light, while the adjacent family room with a fireplace complete with

Joanne Georgiou William Raveis-New York, LLC

184 Deerfield Ln N, Pleasantville, NY 10570

Est $721,066 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
105 Lake Shore Dr, Pleasantville, NY 10570

105 Lake Shore Dr, Pleasantville, NY 10570

/4
$300,000
- Land
- 0.11 Acre
- $2,727,273 per Acre
85 Sarles Ln, Pleasantville, NY 10570

Calling all builders! With variances this is a buildable lot in prime village location. Water and sewer available.

Sharon Foley ERA Insite Realty Services

85 Sarles Ln, Pleasantville, NY 10570
$1,250,000 Sold Jul 25, 2025
- 2,779 Sq Ft
- $450/SF
- 14 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
698 Bear Ridge Rd, Pleasantville, NY 10570

AO - Your Dream Home Awaits in the award winning Byram Hills School District. Discover contemporary elegance in this beautifully maintained 3-bedroom, 2-bath ranch. Set back from the road, a long driveway leads to a two-car garage with extra storage, offering both privacy and convenience. The inviting foyer welcomes you with a skylight and soaring cathedral ceiling. The open living area features

Keri Cipriano William Raveis Real Estate

698 Bear Ridge Rd, Pleasantville, NY 10570

Est $755,716 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,650 Sq Ft
135 Lake Shore Dr, Pleasantville, NY 10570

135 Lake Shore Dr, Pleasantville, NY 10570

Showing Results 41 - 80, Page 2 of 18

New York Westchester County Pleasantville

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage