Pleasantville, NY Homes

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  /33

  $629,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,117 Sq Ft

  8 Foxwood Dr Unit 5, Pleasantville, NY 10570

  Step into elegance and comfort in this beautifully updated second-floor condo in the sought-after Foxwood community. The stunning kitchen, featuring a spacious island with seating, quartzite countertops, stainless steel appliances, and ample cabinetry, opens to the living and dining areas, with access to a private balcony. The primary suite includes an updated half bath and walk-in closet. A

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 825-6710

  8 Foxwood Dr Unit 5, Pleasantville, NY 10570
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  Explore Pleasantville

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  /26

  $2,949 - $3,782 per month

  The Atwood

  Studio - 1 Bed

  1 Vanderbilt Ave, Pleasantville, NY 10570

  An ode to the artists and laureates steeped in the history of Pleasantville, The Atwood is nestled just a block from downtown restaurants and shops. The Atwood is an upscale boutique apartment community with a multitude of comfort and health driven amenities. Enjoy complimentary freshly ground coffee as you relax in our finely appointed lobby lounge soaking in natural light. Head downstairs to

  1 Vanderbilt Ave, Pleasantville, NY 10570
• 

  $650,000 Sold Aug 29, 2025

  • 1,848 Sq Ft
  • $352/SF
  • 115 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1961

  9 Grandview Dr, Pleasantville, NY 10570

  Location, Location, Location. There are no truer words. This house has the perfect location. Walking distance to Pleasantville Schools and all that the Village of Pleasantville has to offer, from its many restaurants to the famous farmer's market to the acclaimed Jacob Burns movie theater. Bring your dreams to this home and make it your own. The opportunities are endless.

  Sharon Foley ERA Insite Realty Services

  9 Grandview Dr, Pleasantville, NY 10570
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  85 Broadway Unit 2N, Pleasantville, NY 10570

  85 Broadway Unit 2N, Pleasantville, NY 10570
• 

  

  

  /26

  $825,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,895 Sq Ft

  46 Walnut St, Pleasantville, NY 10570

  Calling all builders, dreamers or buyers who want their home and property to be their sanctuary! This 1920's three bedroom colonial is nestled on an oversized property with a buildable lot. It is surrounded by beautiful flowers, mature plantings, trees and rock gardens! This house and property offer endless possibilities including a subdivision or perhaps add a built-in pool or keep the

  

  Loretta Fleming Chiavetta

  Coldwell Banker Realty

  (914) 386-2323

  46 Walnut St, Pleasantville, NY 10570
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  /15

  $3,500 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  590 Bedford Rd Unit 7, Pleasantville, NY 10570

  Welcome to Greenwood Condominium, where convenience meets village living in the heart of Pleasantville. This first-floor, two-bedroom home offers an easy lifestyle with freshly painted interiors, refinished hardwood floors, new window blinds, and natural light throughout. The updated kitchen is designed for both function and style, with custom cabinetry, counter seating, and a decorative tile

  Felicia Marquie Houlihan Lawrence Inc.

  590 Bedford Rd Unit 7, Pleasantville, NY 10570
• 

  $2,300,018 Sold Aug 27, 2025

  • 3,197 Sq Ft
  • $719/SF
  • 6 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1982

  177 Deerfield Ln N, Pleasantville, NY 10570

  Welcome to this beautifully renovated, sun-filled 4-bedroom, 3.5-bathroom Colonial in the award-winning Chappaqua School District. Thoughtfully designed for both style and comfort, this home features a seamless open-concept layout that enhances natural light and ease of living.The covered front porch welcomes you into a gracious foyer, leading to an elegant formal dining room, a spacious

  Jennifer Harris Compass Greater NY, LLC

  177 Deerfield Ln N, Pleasantville, NY 10570
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  175 Bedford Rd Unit 2, Pleasantville, NY 10570

  175 Bedford Rd Unit 2, Pleasantville, NY 10570
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  /36

  $1,600,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,467 Sq Ft

  112 Great Oak Ln, Pleasantville, NY 10570

  Nestled in the heart of the sought-after Village of Pleasantville, just steps away from everything Pleasantville...resturants, shops, schools, Metro North and the Farmer's Market, this quintessential 1920s Colonial invites you to experience the perfect blend of timeless charm and modern luxury. From the moment you walk onto the welcoming rocking chair porch—ideal for entertaining or enjoying a

  

  Loretta Fleming Chiavetta

  Coldwell Banker Realty

  (914) 829-3501

  112 Great Oak Ln, Pleasantville, NY 10570
• 

  

  /29

  $4,500 per month

  • 2 Beds
  • 1 Bath
  • 901 Sq Ft
  • House for Rent

  14 Mountain Trail, Pleasantville, NY 10570

  Charming Cottage for Rent in the Pleasantville School District!This delightful 2-bedroom, 1-bath home includes a bonus room that can easily serve as a 3rd bedroom, office, or guest space, offering the perfect blend of comfort and flexibility.Enjoy incredibly low utility bills thanks to the energy-efficient geothermal heating and cooling system. The home is bathed in natural light with an

  SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

  14 Mountain Trail, Pleasantville, NY 10570
• 

  $1,400,000 Sold Aug 26, 2025

  • 3,434 Sq Ft
  • $408/SF
  • 23 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1996

  17 Country Club Ln, Pleasantville, NY 10570

  Welcome to Pleasantville Country Club, where luxury and convenience unite to create an extraordinary lifestyle. This beautifully appointed 3-bedroom townhome, complete with an attached garage, is perfectly located across from the Clubhouse, pool, restaurant, and pro shop—putting world-class amenities just steps away. Step inside and be greeted by gleaming wood floors and sun-drenched spaces, as

  Kile Boga-Ibric Houlihan Lawrence Inc.

  17 Country Club Ln, Pleasantville, NY 10570
• 

  Est $558,000 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  290 Manville Rd Unit N24, Pleasantville, NY 10570

  290 Manville Rd Unit N24, Pleasantville, NY 10570
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  /45

  $1,395,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,703 Sq Ft

  46 Dennis Ln, Pleasantville, NY 10570

  Enjoy carefree living in this exquisite private townhome located in the highly desirable Enclave in Pleasantville. Meticulously upgraded with luxurious finishes, the primary suite is conveniently situated on the main level for those looking for one-level living. Natural light floods the home through a two-story entryway, flanked by a formal dining room and a den featuring built-in shelves and a

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 350-2593

  46 Dennis Ln, Pleasantville, NY 10570
• 

  

  /10

  $3,500 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  155 Washington Ave, Pleasantville, NY 10570

  First floor of a charming village colonial. Updated bath. Huge eat in kitchen. Laundry area in basement with private washer and dryer. DRIVEWAY PARKING. VERY CLOSE TO TRAIN/TOWN/RESTAURANTS/JACOB BURNS FILM CENTER. Patio and Large back yard. Just a short distance from everything that Pleasantville has to offer. Storage area in basement. Owner pays for landscaping/heat/water, tenant pays electric

  Tom Consaga RE/MAX Ace Realty

  155 Washington Ave, Pleasantville, NY 10570
• 

  $508,000 Sold Aug 26, 2025

  • 925 Sq Ft
  • $549/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  293 Manville Rd Unit 1H, Pleasantville, NY 10570

  Pleasantville Gardens Condominium, Perfect Heart of the Village Location.. 1st Floor One Level Living with a Private Front Porch Entry, Foyer, Coat Closet, Spacious Living Room and a Formal Dining Room.. Updated Kitchen with Pantry, Beautifully Cabinetry and Counters, Decorative Tile Backsplash, Tile Flooring, Stainless Steel Appliances and Gas Range.. 2 Bedrooms, Updated Hall Bathroom and Hall

  Vincent Vetrano Douglas Elliman Real Estate

  293 Manville Rd Unit 1H, Pleasantville, NY 10570
• 

  Est $1,228,544 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,545 Sq Ft

  70 Sarles Ln, Pleasantville, NY 10570

  70 Sarles Ln, Pleasantville, NY 10570
• 

  

  /42

  $1,275,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,051 Sq Ft

  26 Dennis Ln, Mount Pleasant, NY 10570

  This stunning townhouse, one of Toll Brothers' original model homes, is the epitome of luxury living. Boasting exquisite upgrades throughout, this home features top-of-the-line finishes, custom built-ins, fabulous moldings, designer lighting, and impeccable decorative details. The master suite is a true retreat with a sitting area, vaulted ceilings, and a luxurious en-suite bath with heated

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 483-3294

  26 Dennis Ln, Mount Pleasant, NY 10570
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  /16

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft
  • Apartment for Rent

  39 Washington Ave Unit 204, Pleasantville, NY 10570

  Welcome to Washington Avenue Lofts, where luxury meets convenience. Our residences offer a variety of layouts, including studios, 1-bedroom, and 2-bedroom options. Each home is designed with premium finishes, featuring quartz countertops, custom cabinetry and closets, wood flooring, recessed lighting, GE stainless steel appliances, in-unit washer/dryer, and more. On-site amenities include a Latch

  Stacey Pinkas Douglas Elliman Real Estate

  39 Washington Ave Unit 204, Pleasantville, NY 10570
• 

  $685,000 Sold Aug 25, 2025

  • 1,686 Sq Ft
  • $406/SF
  • 50 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1956

  520 Washington Ave, Pleasantville, NY 10570

  Tucked perfectly between the Villages of Pleasantville and Chappaqua, this home presents a wonderful opportunity to live within the acclaimed Pleasantville school system. The open concept first floor could be a show stopper with some TLC. Three bedroom upstairs and a full hall bath allows for sleeping options or perhaps a home office. A half a flight down from the first floor is the laundry and a

  Amy Via Houlihan Lawrence Inc.

  520 Washington Ave, Pleasantville, NY 10570
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  177 Bedford Rd Unit 3, Pleasantville, NY 10570

  177 Bedford Rd Unit 3, Pleasantville, NY 10570
• 

  

  /50

  $1,325,000

  • 5 Beds
  • 4 Baths
  • 3,500 Sq Ft

  302 Washington Ave, Pleasantville, NY 10570

  Welcome to 302 Washington Avenue, a beautifully crafted 5-bedroom, 4-bathroom Colonial located in one of Pleasantville’s most sought-after neighborhoods. This newly constructed home combines timeless design with modern amenities, all within walking distance to Metro North, local shops, restaurants, and scenic parks—perfect for those seeking convenience without compromising on luxury.Step

  Cathy DeBow William Raveis Real Estate

  302 Washington Ave, Pleasantville, NY 10570
• 

  

  /17

  $5,100 per month

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft
  • Apartment for Rent

  39 Washington Ave Unit 209, Pleasantville, NY 10570

  Welcome to Washington Avenue Lofts, where luxury meets convenience. Our residences offer a variety of layouts, including studios, 1-bedroom, and 2-bedroom options. Each home is designed with premium finishes, featuring quartz countertops, custom cabinetry and closets, wood flooring, recessed lighting, GE stainless steel appliances, in-unit washer/dryer, and more. On-site amenities include a Latch

  Stacey Pinkas Douglas Elliman Real Estate

  39 Washington Ave Unit 209, Pleasantville, NY 10570
• 

  $1,080,000 Sold Aug 25, 2025

  • 2,850 Sq Ft
  • $379/SF
  • 58 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  750 Bedford Rd, Pleasantville, NY 10570

  Step into your private oasis in this enchanting 4-bedroom colonial, nestled in the award-winning Pleasantville school district! With its spacious living room featuring French doors to the patio and a cozy wood-burning fireplace, you’ll love the warmth and elegance this home exudes. The inviting dining room flows seamlessly into an eat-in kitchen, complete with doors that lead to a fantastic back

  Cynthia Leite ERA Insite Realty Services

  750 Bedford Rd, Pleasantville, NY 10570
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft

  62 Manville Rd Unit 2, Pleasantville, NY 10570

  62 Manville Rd Unit 2, Pleasantville, NY 10570
• 

  

  /32

  $1,375,000

  • 3 Beds
  • 3.5 Baths
  • 3,468 Sq Ft

  30 Dennis Ln, Pleasantville, NY 10570

  Don’t walk—run to this rare 3,500 square foot end-unit townhome in The Enclave, Pleasantville. Perfectly situated on one of the community’s most desirable lots, it offers a private oversized backyard, expansive deck, and patio. Inside, the light-filled open layout showcases a Chef’s kitchen with stainless steel appliances, a walk-in pantry, hardwood floors, custom millwork, and plantation

  Sari Shaw Compass Greater NY, LLC

  30 Dennis Ln, Pleasantville, NY 10570
• 

  

  /14

  $4,900 per month

  • 3 Beds
  • 1 Bath
  • 1,650 Sq Ft
  • Apartment for Rent

  91 Marble Ave Unit 2, Pleasantville, NY 10570

  Welcome to your new home in the charming village of Pleasantville! This beautifully renovated 3-bedroom, 1-bath apartment is located on the second floor of a well-maintained multifamily home, offering a perfect blend of modern comfort and small-town convenience. Spacious and sun-filled living room with large windows and recessed lighting. In-unit washer & dryer for your convenience with central

  Ryan Weir Keller Williams NY Realty

  91 Marble Ave Unit 2, Pleasantville, NY 10570
• 

  $1,257,000 Sold Aug 21, 2025

  • 2,676 Sq Ft
  • $470/SF
  • 40 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  72 Larrys Ln, Pleasantville, NY 10570

  This beautiful home, situated on 1.13 acres has been meticulously maintained and emanates charm. Details like hardwood floors and crown molding are showcased throughout the home. BBQ on the deck, have a cup of coffee in the screened in porch or front porch or a glass of wine on the stone patio. The kitchen will inspire you to elevate your cooking and dining. Relax and enjoy a great book or having

  Donald Dwyer Howard Hanna Rand Realty

  72 Larrys Ln, Pleasantville, NY 10570
• 

  Est $1,218,117 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,640 Sq Ft

  68 Sarles Ln, Pleasantville, NY 10570

  68 Sarles Ln, Pleasantville, NY 10570
• 

  

  /36

  $1,100,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,400 Sq Ft

  15 Old School Ln, Pleasantville, NY 10570

  Historic 1830's home, original Pleasantville School Building located on a small private road in the heart of Pleasantville. Just a short walk to all this beautiful town has to offer. Beautiful features such as a wrap around porch, cozy family room with a fire place, large eat in kitchen and a private primary bedroom, will have you wanting to move right in and make this house your home. All of

  Sharon Foley ERA Insite Realty Services

  15 Old School Ln, Pleasantville, NY 10570
• 

  

  /31

  $4,900 per month

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft
  • House for Rent

  170 Sky Top Dr, Pleasantville, NY 10570

  Nature at your door steps. Beautiful with mature trees, a large level lawn, expensive stone walkway set on 0.25 acre of park-like property. A wonderfully updated 3 bedroom 2 baths plus large family room Split in sought-after neighborhood. Enter through the foyer opening to the large family/playroom/Den/4th Bedroom with custom built-in cabinetry. The sun-lit kitchen with L-shaped island, granite

  Alicja Bohmrich Houlihan Lawrence Inc.

  170 Sky Top Dr, Pleasantville, NY 10570
• 

  $416,000 Sold Aug 19, 2025

  • 760 Sq Ft
  • $547/SF
  • 20 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1977

  8 Foxwood Dr Unit 6, Pleasantville, NY 10570

  Beautiful Foxwood Condominium in a Picturesque Country Setting.. Rarely Offered " Pembroke " Garden Model with Wood Burning Fireplace.. Light and Bright with Southern Exposure Overlooking Meticulously Kept Grounds.. Entry Foyer with Coat Closet.. Galley Kitchen with Plenty of Cabinets and Counter Space.. Dining Area with Door Out to Balcony.. Spacious Living Room with Picture Window and Fireplace

  Vincent Vetrano Douglas Elliman Real Estate

  8 Foxwood Dr Unit 6, Pleasantville, NY 10570
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  56 Manville Rd Unit 1, Pleasantville, NY 10570

  56 Manville Rd Unit 1, Pleasantville, NY 10570
• 

  

  /34

  $1,435,000

  • 3 Beds
  • 2.5 Baths
  • 2,751 Sq Ft

  54 Dennis Ln, Pleasantville, NY 10570

  Set privately in the highly sought-after Enclave neighborhood, this beautiful end unit offers the perfect blend of luxury, space, and convenience. Exceptionally upgraded and meticulously maintained, this home is truly move-in ready. Step inside to discover an open and inviting floor plan featuring a light-filled great room with vaulted ceilings, a gas fireplace, and sliding doors that open to a

  Alaina Bainlardi William Raveis-New York LLC

  54 Dennis Ln, Pleasantville, NY 10570
• 

  $2,170,000 Sold Aug 18, 2025

  • 4,707 Sq Ft
  • $461/SF
  • 11 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1984

  117 Deerfield Ln N, Pleasantville, NY 10570

  This refreshed, sun-filled Colonial home with a lovely gunite pool, located in the award winning Byram Hills School District, is ready for it's next owner. The remodeled gourmet kitchen featuring high-end appliances, a center island, custom cabinets and stunning new counters seamlessly connects to the family room, where a stone fireplace sets the stage for cozy gatherings. The living and dining

  Patti Howard Compass Greater NY, LLC

  117 Deerfield Ln N, Pleasantville, NY 10570
• 

  Est $967,865 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,984 Sq Ft

  320 Sarles Ln, Pleasantville, NY 10570

  320 Sarles Ln, Pleasantville, NY 10570
• 

  

  /40

  $1,250,000 Open Sun 11AM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,858 Sq Ft

  61 Walnut St, Pleasantville, NY 10570

  This custom-built Contemporary Colonial offers the best of modern luxury, elegant amenities with attention to detail all in this private park like setting at the end of a cul-de sac. This lovely home is impeccably maintained and shows pride of ownership with an expansive yet intimate environment for comfortable family living, and great flow for entertaining. As you enter you will notice tiled

  Jeanne Beckley Howard Hanna Rand Realty

  61 Walnut St, Pleasantville, NY 10570
• 

  $773,000 Sold Aug 13, 2025

  • 2,000 Sq Ft
  • $386/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  9 Samson Dr, Pleasantville, NY 10570

  PRICE TO SELL! THIS ONE WON'T LAST! Welcome to this picture-perfect Raised Ranch tucked away on a peaceful cul-de-sac in desirable village of Pleasantville. This beautifully maintained home offers bright, spacious rooms and a warm, inviting atmosphere throughout. The main level features a formal living room, a dining area and a modern eat-in kitchen. A primary bedroom, two additional bedrooms,

  John Buoninfante Real Broker NY LLC

  9 Samson Dr, Pleasantville, NY 10570
• 

  Est $447,269 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  590 Bedford Rd Unit 2, Pleasantville, NY 10570

  590 Bedford Rd Unit 2, Pleasantville, NY 10570
• 

  

  /31

  $1,300,000

  • 3 Beds
  • 2.5 Baths
  • 2,912 Sq Ft

  140 Old Farm Rd S, Pleasantville, NY 10570

  Enjoy vacation like living everyday in this spacious home located on 1 acre of parklike property. This home features a no-step ranch with open floorplan and a beautiful primary suite on the main level. Doors out to a spacious deck overlooking private pool complete with outside kitchen/barbecue area make for a vacation at home. The lower level consists of family room with door out to

  Sharon Foley ERA Insite Realty Services

  140 Old Farm Rd S, 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

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