luxury houses for sale Pleasantville, United States

Welcome to the intersection of style and functionality located within one of the Chappaqua School District's most-coveted neighborhoods. 2 Point Place was built in 2017, and numerous improvements over the past few years have dramatically enhanced the home's appeal. Upon entering, the scale of the rooms and the abundance of natural light is immediately apparent throughout. Main level highlights include a vast kitchen with dining nook and opens to a spacious family room accented by a wood-burning fireplace. Remarkable detailing is evident in the adjoining living room with transom windows and a coffered ceiling, while the sun-drenched, formal dining room is complete with a tray ceiling. The second level features four large bedrooms including the recently improved primary bedroom suite with a voluminous bath and capacious walk-in closet equipped with custom cabinetry and flanked by a hidden reading room. Three large bedrooms and two full baths complete the upstairs, while the recently renovated lower level will entice individuals of all ages. The space includes a temperature-controlled wine room, viewing room, office large enough to double as a guest bedroom, and a two-tiered bar with Italian tile-flooring and French doors leading to the adjacent bluestone patio outside. The awe-inspiring outdoor spaces feature a main level-adjoining covered deck with a built-in grill, gas fireplace, and custom low-profile hurricane shutters. The recently completed stone patio is an ideal backdrop for watching the sun set into the valley beyond and is complete with a pizza oven, a custom firepit and a multi-functioning gas and wood-burning fireplace. Other recent improvements include an 11-zone irrigation system, mahogany garage doors, extensive landscaping with privacy screening and outdoor lighting, and a whole-house generator. Don't miss your chance to see a truly phenomenal home. This is the one you've been waiting for!

Nestled on two-acres of lush, private landscape at the end of a serene cul-de-sac in the Byram Hills School district and in the lovely hamlet of Thornwood, this exquisite residence offers 6,331 square feet of warm, inviting living space and an array of outdoor entertainment areas set against a stunning backdrop of natural beauty only 36 miles from New York City. Lives like a six bedroom and is a two acre parcel in a one acre zone. The light and airy Chef's kitchen flows easily to the grand family room with 22' ceilings and oversized windows, the living room creates a warm ambiance at the heart of the home with original wood burning fireplace. Double French doors open onto an expansive deck overlooking the pool and private grounds for an enjoyable alfresco dining experience. Ascend to the upper level to take in the magnificent sunsets from the upstairs balcony adjoining the primary suite or indulge in the private sanctuary of the main spa bathroom, set thoughtfully apart from the four upstairs bedrooms. Explore your creative pursuits in the gatehouse studio or enjoy relaxed living in the gracious sunroom overlooking perennial gardens and flowering trees. On the lower level, the seamless connection between the generous wet bar, full gym and recreational room to the outdoor provides the ideal setting for effortless entertaining. Ready for summer here at 27 Sunset Drive! Discover refined living in this masterfully expanded and renovated five bedroom, 4.1 bath estate, perfectly balancing historic charm with modern comforts.Welcome home!

Who's ready to refresh the cutest Tudor in the world? Curb appeal, spacious lot, beautiful garden, attached garage, are all ready for you. As is an ideal location in quiet neighborhood just blocks from Hawthorne Elementary School. Inside, behold great bones- entry foyer, hardwood floors, cozy fireplace, bonus sunroom, formal dining room plus eat-in-kitchen, 3 bedrooms and 1 full bathroom upstairs, plus a stone patio, walk-up unfinished attic for storage, and a huge unfinished basement to grow into. Why share walls with neighbors when you can have your own house and yard? Bring your contractor and make this your home sweet home!

Just completed! In-town location ready to move in. This state of the art offering, by esteemed builder Tavo Development, lives like a 4 or 5 bedroom house. An incredible opportunity in Chappaqua for a refreshing new build with the convenience of in-town living, where you can walk to school, town and train. A serene setting, overlooking Duck Pond, offers open concept living with highlights that includes a covered porch off the Family Room for entertaining, an office/library and large gourmet Kitchen with Dining Area. The second floor provides a private spacious primary suite with a sitting room, dressing room and a large bath. Two additional ensuite bedrooms, laundry and an incredible bonus room with endless opportunities complete this level. The third floor showcases as a potential workout, office or lounge space. The finished lower level, featuring a wine closet, offers additional space for recreational enjoyment. Future hookup to sewer. Minutes to Chappaqua, highways and a 50-minute drive to NYC. Super convenient to all.

Indulge in the ultimate luxury living experience in this exquisite dream home, nestled in its own compound, within a private 4-acre botanical garden. This exceptional property is designed for entertainment and outdoor living, featuring resort-like amenities including an inground gunite pool with a spa, a hard-court tennis/pickleball/basketball court, and a personal 140+ yard par 3 golf hole complete with bunkers and multiple tee boxes for various shot perspectives. A country club experience, without leaving home. This is a truly spectacular, one-of-a-kind trophy property to call home. Step into luxury as you enter the main residence, spanning over 6,000 square feet across three levels, with 5 bedrooms, 4 full bathrooms, and a powder room. The first floor sets the stage for indoor entertainment with a massive, sun-filled great room, a large formal dining room, and a den set off the eat-in, chef's kitchen. The massive deck running the full length of the house seamlessly blends indoor and outdoor living, connecting you from the first level to the pool area down below. The finished lower level features a nice recreation area, an au Pair Suite with a full bath & shower, and is highlighted by a 4500-bottle wine cellar. The property also boasts a remarkable 1362-square-foot freestanding office, perfect for those who desire a dedicated workspace separate from the main house, above the detached 3-car garage. A perfect space for an office/game room/guest suite, equipped with a summer kitchen and full bath - ideal for work, play, entertaining, or hosting guests. A whole house generator ensures uninterrupted power supply, and every corner of this sanctuary exudes thoughtful sophistication, from the manicured grounds to the breathtaking vistas. This unparalleled estate offers a harmonious blend of work and leisure, making it truly one of a kind. Approx. FULL square footage = 7,388 including Studio above the garage Main House = 6,026sf Studio above Garage = 1,362sf

Welcome home to this beautiful two bedroom, two bathroom townhouse with all new appliances. With more than 1500 square feet on three levels, a wood burning fireplace, sliders to a lovely outdoor area and a spacious primary suite with walk in closet, this townhouse is ready for you. Chestnut Oaks is steps from Downtown Chappaqua village with shops, train and every convenience just down the street! This particular home has a very private primary suite on its own level. The second bedroom is also private on its own level as you have three separate levels with this property. The open kitchen and dining area are also open to the very large and bright living room. The development offers pool and tennis and easy parking. 377 North Greeley Avenue offers space, natural light and an outstanding location. Welcome home!

Seize this rare opportunity to own an iconic estate rich in history, dating back to the 1890s. This distinguished property, known as The Manor House, was built for and live in by Walter Law, the founder of The Village of Briarcliff Manor. Constructed on Brier Cliff Farms, originally acquired from James Stillman, then-President of National City Bank (now Citibank), the estate at 139 Scarborough Rd exudes a blend of historical charm and opulence. Spanning over 9 acres, the expansive 15,000+ sq. ft. residence features 14 bedrooms, 7.1 bathrooms, a private entertainment hall, a bar, an atrium, and an indoor pool, all highlighted by distinctive architectural elements. The wood paneling throughout the estate, imported from The Baxter Church in England, has been meticulously preserved. In 1928, The Manor House served as a clubhouse for the Metropolitan Masons with a golf course on property and was once the venue for a notable boxing match between Jack Sharkey and Carl Brisson in the early 1930s. Designed with input from the Olmstead Brothers, renowned landscape architects behind Manhattan's Central Park, the estate still features remnants of their work, including waterfalls, retaining walls, statues, gazebos, and greenhouses. Neighbors to the Manor House have included prominent families such as the Rockefellers, Shepherds, Speyers, Macys, Webbs, and Astors. This is a rare opportunity to restore and own a significant piece of history. Don't miss the chance to make this extraordinary estate your own.

For the first time in five decades, this delightful brick cape cod colonial home nestled on a cul de sac presents the perfect setting for your next chapter. Step inside and find a spacious living room featuring a wood burning fireplace, an adjacent eat in kitchen and dining room with easy access to the lush level yard. A primary bedroom, a versatile den/fourth bedroom alongside a full bath offer convenience for guests or a home office space. Upstairs, discover two additional bedrooms and a hall bathroom, plus an unfinished bonus space await your personal touch. The large walk out basement offers a large recreation room, dedicated laundry area, ample workspace, and endless potential for storage or future finishing. Enjoy the convenience of an attached one-car garage, providing both parking and additional storage options. Located minutes away from the breathtaking Kensico Dam and all the best that Valhalla has to offer, this lovingly maintained home is the ONE you have been waiting for!

A sweeping drive leads to this cedar shake, Hamptons-style estate sited on 2+ magnificent, lush, landscaped acres in one of Armonk's most coveted locales. This elegant five-bedroom home is imbued with style and fine craftsmanship, apparent as you stroll through gracious rooms. The foyer opens to formal spaces segueing to the gourmet kitchen with breakfast room and family room boasting an impressive floor-to-ceiling stone fireplace. A den looking into the screened-in sunroom with fireplace, opens to the idyllic backyard. Set apart from the main living spaces is a separate first floor three-bedroom suite. Completing this level, you'll find a study, laundry, and mudroom accessing a 3-car garage. The upper level offers a private primary suite with balcony, dressing room and spa bath with steam shower. Passing through the loft is a lounge, full bath, and bedroom. The lower level offers a large rec room, and for the wine and cigar enthusiast, a walk-in wine room with seating for four. The backyard, a highlight of the property, encompasses an oversized patio with built-in stone kitchen, heated pool with spa and stone walls amidst verdant greenery. An exceptional offering minutes to town and schools. 50 minutes to NYC.

Boldly elegant 1930's manor in the Whippoorwill estates area. Periodic character is juxtaposed with contemporary flair creating a distinct luxury that is full of personality. The brightly renovated interiors feature perfect proportions and a sought-after layout for today's lifestyle. A welcoming entry hall opens up to an expansive slate terrace overlooking sweeping lawns and Armand Benedek-designed pool. The main level presents a grand living room, library, formal dining room, butler's pantry, kitchen with breakfast room and sun porch, and au pair suite. A wide staircase leads to the upper level offering a primary suite with dressing room, bath with steam room and sauna, four additional bedrooms, a guest wing, and sitting room. The lower-level great room and wine cellar create added space for stylish entertainment. Majestically set on three acres, with a gated entry on a cul-de-sac street plus a service entrance from Whippoorwill Rd. Close to downtown Armonk, highways and 45 mins to NYC.

Welcome to 15 Shelley Avenue! Must see in person to truly appreciate all this home has to offer. Lovely and charming four bedroom home with amazing bonus space of ~500 sqft in the finished basement. The first floor greets you with a bright and airy living room which opens up to the formal dining room with beautiful built-in cabinetry and views of the level yard. The kitchen has all of the essentials with newer appliances and direct access to the long driveway which can accommodate four standard vehicles not including one in the garage. Two generously-sized bedrooms and a full bathroom with newer vanity round out the first floor. On the second floor, you will find two additional spacious bedrooms and a recently renovated full bathroom with a walk-in shower. Ample storage lines the upstairs hallway and inviting nooks can be found on each side of the hallway which can be used as a seating area or a fun place for kids to gather. All interior walls have been recently painted and beautiful hardwood floors are installed throughout. Close to the Valhalla Metro North station (

3-bedroom townhouse style coop lovingly maintained. This end unit with three sided exposures, one side facing the woods, offers amazing sunlit rooms and convenience to all sources of transportation. The spacious 3-bedroom unit is conveniently located for shopping, restaurants, and more; yet offers a quiet residential setting. Private path leads to no step entry of #91 Charter Circle, with eat-in kitchen with LG stainless steel refrigerator and GE Dishwasher and Oven with Flat top electric range, and powder room. Step further inside to an open concept living room and dining room, with gleaming hardwood floors and flooded with natural light. The 2nd floor offers 3 generously sized bedrooms with amazing floor to ceiling closet space & full bath. This one-of-a-kind complex offers 2 playgrounds, basketball court, two storage areas and assigned parking (in addition to street parking right in front). First time on the market in over 30 years. Must see!

Calling all antique lovers! On the hilltop of Ryder Road in Ossining sits an historic property going back centuries, on the market for the first time in decades. The 33 Ryder Road 1826 farmhouse, claimed to be Ossining's oldest residence by The Citizen Register of 1936, is oozing with original charm, including its huge rocking chair front porch, 7' high ceilings, wide plank hardwood floors and four working fireplaces. Built in two sections, the one and a half story smaller house is believed to be the oldest section, built in the late 1700s. The larger two-story section was connected to the original, added on in 1826 to house the workers of the farm. Built on a stone foundation with brick construction and a timber frame, all the wood in the house was felled and hewn on the farm. In addition to the expansive living space shown in the photos and described, there are many more rooms likely used for the workers as noted. Create your own farmhouse dream-come-true with this once in a lifetime opportunity, frozen in time but close to all that wonderful Westchester has to offer: trains, restaurants, parks, great schools and shopping. A lifestyle like no other. Taxes with STAR approx $18,032.

Attention Investors! Introducing an exceptional income-generating 4 unit property of superb architectural design and amenities. Walk to town, Metro-North, Hudson River. Plenty of parking with 2 driveway entrances on both Lincoln Place and Cedar Place, artistically designed mason work enhance the property with stately pillars at the entrance. A large brick garage plus a large area for a second garage on this .6 lot! Apt#4 enters through the main entrance into a double height foyer with a dramatic curved staircase leading to a spacious landing on the second floor setting the stage for luxury living with a formal dining room, stunning updated chef's kitchen with top of line appliances and 3 bedrooms. This unit has access to a large attic for storage or can be finished with multiple rooms and river views. Apts, 1 & 3 open to the community courtyard while apt #2 has a Trex front porch. 2 Laundry rooms, one community and one for Unit #4. 7 Lincoln Place in Ossining, New York, was originally built in 1836 and served as a single-family mansion before being converted into a multi-family residence. The home is notable for its historical architecture, constructed with Brick, Limestone, Cedar, Copper and other materials typical of the period. It retains its historical charm and significance in the local community. A second lot, #5 Lincoln is part of the same tax record and can hold a new garage structure with 4 possible garage spaces. Short commute, Metro North Train to NYC is walkable.

Location, Location, Location...on the Majestic Hudson River! Situated in the desirable Scarborough area of Briarcliff Manor, this home boasts spectacular unobstructed views of the Hudson River, providing breathtaking scenery with direct views of Hook Mountain and serene surroundings. This Center Hall Colonial sits on a generous .90-acre lot, offering ample space for outdoor activities and relaxation. The interior features five bedrooms and 5 1/2 baths, providing plenty of accommodation for families or guests. The main level comprises a living room, dining room, dine-in kitchen, family room, bedroom/office, and a full bath, offering a perfect flow for everyday living and entertaining. On the 2nd level you will find the Primary Suite with full bath, 3 additional bedrooms and hall bath. The walk-out lower level, spanning over 1330+ square feet, offers versatile space that can be tailored to suit various needs, such as a gym, office, or recreation area. Residents can savor magnificent sunsets from the comfort of their own home, enhancing the overall ambiance and appeal of the property. The area offers a wealth of amenities, including the Rockefeller State Park Preserve, Briarcliff Village Recreation, Stone Barns Center, and various historic sights, providing opportunities for outdoor recreation and cultural enrichment. This location provides easy access to Metro North train services, convenient shopping and Sleepy Hollow Country Club. Overall, this property presents an enticing combination of scenic beauty, functional space, and convenient location, making it an ideal choice for those seeking a tranquil yet accessible lifestyle!

When only EXCEPTIONAL will do.. This custom Georgian colonial designed by Nasser Nakib Architect PLLC offers the ultimate in fine details, design and materials. 11' ceilings, open flow and walls of windows set the tone for this luxurious lifestyle home. A front to back foyer with floating staircase, wide wood floors, slate roof and smart house technology are amongst some of the many special features. A gourmet kitchen with state-of-the-art appliances, hidden walk-in pantry, and double islands flow to a sun-lit breakfast room and family room with fireplace, all accessing the rear covered patio with views to the pool and fabulous sunsets. An upper-level primary suite offers double spa-like baths, each with soaking tub. One bath offers a refined dressing room with island, the other, an oversized rain head and steam shower. All rooms of the suite lead to the terrace. Three ensuite bedrooms and laundry reside on the upper level as well. The lower level provides a cabana bath for the pool area with shower, double WCs and a laundry. There is a rec room, large gym and conditioned wine cellar along with a large unfinished area here as well. The verdant grounds offer wonderful opportunities for outdoor enjoyment with a large slate patio overlooking the pool and spa. Located in the Chappaqua school district, this is a AAA location offering convenience to train, town and highways.

Rarely available one bedroom plus den and one car attached garage. Living room with fireplace, vaulted dining room ceiling and sliding glass doors to a private deck facing woods provide for a spacious yet cozy feel in this move-in ready condo. Upgrades throughout include wood floors, updated kitchen with stainless steel appliances (2022), updated bathrooms, new windows and vinyl siding. New HVAC and Nest thermostat in 2022. Plenty of private parking in your garage or driveway, plus lots of visitor parking across from the unit (for all those barbeques you're waiting to have). From the driveway, the Belgium block pathway welcomes you into this beautifully appointed unit. Enjoy an easy, fun lifestyle with Fox Hill's great amenities including pool, tennis, and clubhouse. Close to parks (right next to complex), restaurants, train, shopping and all the joys of Westchester living, less than an hour from NYC. Property tax w/ STAR approximately $4,619.