299 houses for sale in Pleasantville, Pleasantville village Mount Pleasant town Westchester County New York

Welcome home to the perfect blend of charm, comfort, and convenience. Nestled on a quiet, tree-lined street, this warm and inviting home welcomes you with a quaint front porch, the perfect place to unwind with your favorite evening drink. Inside, you'll find a bright and sunny layout featuring sparkling hardwood floors throughout. The spacious living room, complete with updated built-in shelving, flows seamlessly into the dining room, creating an ideal space for both everyday living and entertaining. The kitchen offers stainless steel appliances, beautiful countertops, abundant cabinetry, and plenty of storage, while a convenient first-floor powder room adds to the home's functionality. Step outside to your completely private, fully fenced backyard, an ideal setting for entertaining, gardening, or simply enjoying peaceful afternoons in your own outdoor retreat. Upstairs, you'll discover three generously sized bedrooms with exceptional closet space that is sure to impress, along with a

A Gem in Armonk, centrally located in the center of Armonk. There are two structures on the property. Main Building can be used for commercial space. On the second floor with a separate entrance offers a 1 bedroom, eat. In kitchen, living room, full bath. Accessory cottage located on the property offers: Vaulted ceilings, wood-burning stove, kitchenette, Bedroom, Full Bathroom, Large finished loft for storage, level private yard. Ample storage in both buildings. Parking for about 10 cars

Lovely modern Ranch on a cul-de-sac that offers 3+ bedrooms and 3 baths. A covered screened in back deck, where you can view nature and beautiful surroundings, with plenty of privacy. The first floor has very good circular motion, with open access to the living room, kitchen and dining room. Square footage does not include the lower level. With easy living on the main level and fabulous space on the lower level, this home will go quickly. The lower level includes a Murphy bed, within the library, and a summer kitchen in the recreational room. The Office is presently being used as an exercise room. Access to the lower level from both the inside and outside. Walk-out to a fabulous patio area perfect for entertaining. Updates include siding, front door, gutters. Windows and roof were replaced in 2016. Walking distance to Chappaqua train station and very close to the Pleasantville village, which has restaurants, trains, and shops for you to enjoy. Taxes do not reflect the basic star exempt

Welcome to this beautifully sunlit, move-in-ready townhome at 11 Rockhagen Road. The inviting main level boasts open layout with a bright kitchen w/ breakfast bar, SS appliances and the ultimate convenience of first-floor laundry, Living room w/ fireplace, dining room and sliding glass doors to private deck. Upstairs, you will find two spacious bedrooms—including a private primary en-suite with a walk-in shower—alongside a versatile loft area w/ skylight that makes the ideal home office. Complete with central A/C, hardwood floors throughout, low common charges and a one-car garage + driveway, this home offers everything you need. Best of all, you are just minutes away from local parks, dining, Parkways, and both the Pleasantville and Chappaqua Metro-North stations for a seamless commute

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A. H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally

Centrally located in the historic Village of Sleepy Hollow, just one block from vibrant Beekman Avenue, this turnkey Two-Family home with numerous improvements and updates in recent years, offers an exceptional opportunity for owner-occupants and investors alike. Both units are uniquely large duplexes. 1,745 SF (4 bed, 2 full baths) and 1,650 SF (3 bed, 2 full baths). Each featuring a private deck, an eat-in kitchen, in-unit laundry, high ceilings, tall windows, and on-site parking. This property is ideally suited for those looking to live in one unit while offsetting their mortgage and property taxes with rental income, or investors looking to add to their rental portfolio. Within one mile you’ll find the Metro-North Tarrytown Station (36 minutes from NYC), the scenic Hudson River waterfront, marinas, restaurants, and the transformative Edge-on-Hudson development, DeCicco & Sons gourmet supermarket, and more. If you enjoy street fairs, cultural festivals, live jazz, rich history, loca

133 Westlake Drive features 4 bedrooms, 2.5 baths, spacious rooms, a well-designed floor plan, complemented by an inground pool, a private. 49-acre corner lot, and an oversized 2-car garage. Nestled in a highly desirable neighborhood, this Cape offers close proximity to Mt. Pleasant Schools, local restaurants, shopping, and major highways. Just five minutes from the Valhalla Train Station, providing exceptional convenience for commuters. Step inside the tiled entryway, leading to a spacious formal living room highlighted by a wood-burning fireplace with stone mantle and hearth, a formal dining room with beamed ceiling accents, a generously sized eat-in kitchen with double oven and breakfast nook. A large family room that showcases beamed accents, skylights and a second wood-burning fireplace. Hardwood floors lie beneath the carpeting in both the living and dining rooms. The home offers two side decks—one off the kitchen overlooking the flat, private fenced-in yard, and another off the

Experience luxury living at Enclave at Armonk by Toll Brothers, an exclusive townhome community in the heart of Westchester County. This stunning Saunders Fairview offers the convenience of a first-floor primary suite, an open-concept layout with a striking electric fireplace, elegant open railings overlooking the loft, and a finished lower level with a full bath—perfect for entertaining or hosting guests. Relax on your private patio overlooking serene conservation land, all just steps from the community clubhouse. One of the best features of this home is the opportunity to personalize your interior finishes at the Toll Brothers Design Studio, allowing you to create a home that reflects your unique style and taste. Scheduled for Fall 2027 move-in, there's still time to make it your own. Enjoy the ease of low-maintenance living with lawn care and snow removal included, all in a premier location close to major commuter routes, shopping, dining, parks, golf, and nature preserves. Don't mi

Welcome to 65 Laurel Place! Nestled in a quiet neighborhood in the heart of Thornwood, this charming and move-in ready cape is waiting for you to make it your home! This adorable 2 bedroom, 2 bathroom house features the perfect blend of character and modern updates. Beautiful hardwood floors flow throughout much of the home, while the elegant arched doorways add timeless architectural charm. The updated bathrooms provides contemporary style and comfort. The primary master bedroom suite on the second floor has built-in shelving, and a small room that is being utilized as a walk-in closet in the hallway leading to the primary bedroom featuring high ceiling, built-in closets and a skylight. The primary bathroom also has a skylight. Enjoy outdoor living on the spacious deck overlooking the level easy to maintain fenced in yard. Ideal for relaxing or entertaining. The lower level of approximately 500 sq. Ft. is not included in square footage offers extra bonus space with high ceilings, tile

Winding Ridge is a hidden gem in the heart of Westchester County, offering the perfect blend of comfort, convenience, and low-maintenance living. Developed by award-winning builder Martin Ginsburg, this sought-after community is renowned for its thoughtfully designed homes, well-proportioned living spaces, and careful integration with the natural landscape, creating an exceptionally attractive setting. This beautifully maintained three-bedroom townhome features a versatile sky loft and a fully finished walk-out basement, providing generous living space for today's lifestyle. Architectural highlights include vaulted ceilings, skylights, a private deck, and tasteful decorative details throughout. Residents enjoy an exceptional array of amenities, all included in the common charges, including a swimming pool, fitness center, children's playground, tennis courts, and pickleball courts, all conveniently located within the community. Lawn maintenance and snow removal are also included, allow

Experience the pinnacle of new construction in one of Chappaqua’s most coveted locations within the award winning Chappaqua Schools. Built by a highly regarded local builder known for exceptional craftsmanship and thoughtful design, this stunning 5-bedroom, 6.5-bathroom residence offers approximately 6,500 square feet across three finished levels. Privately set on over 11 acres, the property delivers a rare combination of estate-scale living and everyday convenience. The home features 10’ ceilings on the main level, 9’ ceilings upstairs, and a seamless, modern layout designed for both elegant entertaining and comfortable living. A walk-out lower level provides additional flexible living space, while infrastructure for hybrid/electric vehicles reflects today’s lifestyle needs. Surrounded by mature trees and scenic vistas, the grounds offer exceptional privacy and a prime opportunity for a future pool. Ideally located just minutes to Metro-North Railroad for an easy NYC commute, as well

Welcome to 55 Hoags Cross Rd. In the desirable New Castle area of Ossining. Privately set on a level acre and surrounded by trees and natural landscaping, this property offers a rare sense of quiet seclusion: your own peaceful retreat, just moments from town, commuting routes, and everyday conveniences. This beautifully maintained split-level ranch lives like a 4-bedroom and offers exceptional flexibility, effortless indoor-outdoor flow, and space to grow. A welcoming entry foyer opens to a spacious family room with sliding doors leading to a stone patio, perfect for entertaining under the trees or enjoying quiet mornings immersed in nature. A full bath on this level adds convenience for guests. Upstairs, natural light fills the living room, where a fireplace creates a warm focal point. The space flows seamlessly into the dining room and kitchen, with hardwood floors throughout. Sliding doors off the dining room open to a deck overlooking the expansive, private grounds—an ideal setting

Welcome to this extraordinary estate, a gem dating back to the 1900s, situated on over an acre of picturesque land. This sunlit residence boasts 6 spacious bedrooms and 4 1u002F2 bathrooms, making it the perfect sanctuary for entertaining guests. Step inside to experience the remarkable craftsmanship that defines this home. With oversized rooms designed for both formal gatherings and casual moments, you’ll find ample space to create lasting memories. The property features an amazing garden and a fenced outdoor area ideal for summer gatherings and outdoor enjoyment. Conveniently located near Pleasantville, Armonk, and Chappaqua, you’ll have easy access to shopping, dining & Metro North. Don’t miss your chance to own this one-of-a-kind home

Back and better than ever! During its brief time off the market, the seller completed valuable improvements, including a brand-new roof over the balconyu002Fdeck and attached garage, along with beautifully refinished and updated flooring in the living and dining rooms, making this exceptional Colonial even more appealing. Rich in character and timeless charm, this spacious home sits on a picturesque corner lot directly across from James M. Carroll Park. The main residence offers 5 bedrooms and 3 full baths, while a thoughtfully designed addition includes a two-car garage and a versatile motheru002Fdaughter or au pair suite complete with a bedroom, summer kitchen, living area, and private entrance—ideal for extended family, guests, or multigenerational living. Enjoy summer concerts from your second-floor balcony overlooking the park or relax in the screened gazebo surrounded by mature landscaping, privacy-enhancing trees, and a fully fenced backyard with plenty of room for recreation or

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 grounds showcase a harmonious mix of wooded areas, meandering walking trails, expansive lawns, curated gardens, and beautiful stonework, all connected by a thoughtful network of driveways, pathways, and steps. Multiple terraces, patios, and outdoor seating areas are perfectly positioned across the property to capture its remarkable natural surroundings. The thoughtfully designed Main house layout features an expansive family room with wood-burning fireplace perfect for everyday gathering, first-floor bedroom with a full en-suite bath, ideal for guests, along with a dedicated laundry room. The main fl

Imagine a stately colonial home, four bedrooms that lives like six, gracefully set back on a rolling three acre lawn, framed by mature trees and manicured gardens. Inside, you’re greeted with intricate millwork—detailed moldings, and graceful arches that connect each room. The kitchen is a chef’s dream with custom cabinetry and a large island. A fabulous expansive three season screened in porch offers the perfect setting for entertaining. Out back, the sparkling pool is framed by a bluestone patio, as well as a pool house and even a charming tree house. Located in the Chappaqua School District. This is a home that feels both timeless and full of character. AO as of 5/7

PRE-CONSTRUCTION / available for summer 2026 move-in. Discover luxury living at Enclave at Armonk by Toll Brothers in esteemed Westchester County. This community is an intimate enclave of two-story townhomes offering luxury features from top brand-name manufacturers such as Kohler fixtures, Century cabinets, stainless steel appliances, and much more. This quick move-in home is a Saunders Farmhouse model in completely designed with the primary bedroom on the first floor. Enjoy open living with a wood-burning fireplace in great room and upper loft. You can walkout from your great room to a patio and enjoy the serene views of conservation land. Home site is situated on cul de sac street. This home has been thoughtfully designed by our Design Center. Home will be ready for Summer 2026 occupancy. Homeowners will enjoy low-maintenance living with lawn care and snow removal provided. Enclave at Armonk by Toll Brothers is ideally located close to major commuter routes, including 684, I-95, I-2

Take this Amazing opportunity to live in a private neighborhood with award winning Byram Hills School District. This spacious and versatile Ranch offers 3 bedrooms & 2 spacious baths, amazing open basement with sliding glass doors to private yard. The master bedroom suite located on the first floor along with 2 spacious bedrooms to accommodate a comfortable lifestyle. Sitting on one clean private acre allows your creativity to build your dream pool for entertainment or relaxation. Enjoy the brick fireplace on cold winter days to offer a comfortable lifestyle during any season. From the welcoming entry foyer flowing into the the spacious living room, opening to the private dining area and kitchen, the master bedroom suite and two additional bedrooms with linen closets and a specious jet bath just adding to the extras this home can offer. Plenty of parking in the driveway and the oversized attached 2-car garage can always be an added bonus. You can enjoy all of this in a quiet neighborho

Welcome to 26 Meadow Lane, a pristine 2,178-square-foot ranch set on over half an acre of flat, beautifully landscaped property in one of Chappaqua’s most coveted residential neighborhoods. A rocking chair front porch and Belgian block-lined driveway offer an immediate sense of arrival, while sidewalk-lined streets connect the neighborhood to the acclaimed village of Chappaqua, minutes from restaurants, shopping, playgrounds, the library, Metro-North rail service, and more. Situated within the highly sought-after Chappaqua Central School District, including Roaring Brook Elementary and Robert E. Bell Middle School. The sun-drenched main level features a cathedral-ceiling living room anchored by a dramatic stone fireplace that adds immediate texture, warmth, and luxury to the space. The formal dining room overlooks a stunning yard, while the expansive skylit eat-in kitchen with cathedral ceiling offers an abundance of counter space, a center island, and a built-in entertaining hutch wit

Charming front porch colonial on tree lined Street. Front door opens to entry hall, large dining room and living room with hardwood floors, arched walkways between rooms. Beautifully updated kitchen with island and stainless appliances, half bath. A first floor bonus room that can be used as a bedroom or den/office. Upstairs leads to three bedrooms, a full bath, hardwood floors throughout, updated fixtures. Basement has laundry and utilities and storage space plus a playroom. The big deck outback looks over the yard parking for 3+ cars Taxes do not reflect basic star exemption of $1,555

Welcome to this bright and spacious ranch-style home in the sought-after Greenburgh community. Filled with natural light, this well-maintained residence offers comfortable single-level living with a flexible floor plan designed to meet a variety of needs. The main level features three generously sized bedrooms, including a secondary bedroom with a private ensuite bath—a rare and convenient feature that provides additional privacy and versatility. The large kitchen is equipped with stainless steel appliances and offers plenty of space for cooking, dining, and entertaining. The finished lower level provides exceptional additional living space, complete with two bonus rooms, a full bathroom, a separate laundry area, and its own private entrance. Whether used for extended family, guests, a home office, fitness area, or recreation space, the possibilities are endless. Abundant natural light flows throughout the home, creating a warm and inviting atmosphere. Outside, enjoy a sprawling backya

A special opportunity to own and continue the story of a living piece of history. This magnificent 15,000 SF estate, set on 8 pristine acres, was built as the private residence for Walter Law, the founder of Briarcliff Manor and a titan of industry at the turn of the 20th century. The moment you enter the grounds you instantly feel the grandeur and charm of the property. A sweeping driveway flanked by stately stone pillars, each crowned with a lion statue, sets the tone for the regal character that defines this property. The lion motif carries throughout the house & grounds as a cohesive architectural signature. The exterior is a masterpiece of natural stone craftsmanship, crowned by an original slate roof and wrap-around front porch. Statues, walking paths, and multiple water features are woven throughout the landscape, all elements of a design vision conceived with the assistance of the Olmsted Brothers, the illustrious and world-renowned architects of New York City’s Central Park. B

Perfect for investor or end-user. Located in the heart of the village, the structure sits on a 4,356-square-foot lot and offers a classic architectural style characteristic of the historic downtown Ossining area. This multi-family, 2 family with accessory unit ground floor unit. Property features 7 bedrooms and 4 bathrooms

Beautiful like new 2001 4 bedroom 2.5 bathroom colonial with all the bells and whistles. Oak hardwood floors throughout the home. Living Room with gas fireplace/large EIK with separate eating area/sliders that give way to a slate patio enclosed with green plush shrubs and pines. Formal dining room/powder room. Second floor/primary bedroom with vaulted ceilings and walk in closets /bathroom, three additional bedrooms with full bathroom fully renovated and completed less then 1 year ago. Full attic with Besler stairs and plywood footing. Unfinished basement with washer/dryer. Great for playroom or office. Access to CLEAN two car garage. New roof with solar panels 2025 (paid for already). 2023 lamppost. Hallway bathroom and powder room renovated 2024. Tilt and turn windows with grids. Kitchen appliances and countertops upgraded in 2014 with tile backsplash. NEW driveway finished 3 weeks ago. New AC condensers installed 2025 Outside landscaping and additional stonework is METICULOUS and br

Move right into this sparkling, beautifully updated 4-bedroom Colonial, ideally located in the highly sought-after Chappaqua School District. Blending timeless pre-war charm with modern amenities, this home offers exceptional comfort and style. Freshly painted inside and out, the home features beautiful hardwood floors, recessed lighting, a renovated kitchen, updated bathrooms, a wood burning stove and more. A walk-up attic provides excellent storage or future expansion possibilities. Outside, enjoy a large, private property with mature landscaping and perennial gardens, a usable yard, and an expanded driveway accented by elegant Belgian block edging. Additional highlights include an above-ground oil tank and a convenient location close to schools, shopping, dining, transportation, and all that the area has to offer. A truly turnkey opportunity combining character, updates, and convenience