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Homes for Sale with a Pool in Tarrytown, NY

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Welcome to your dedicated resource for homes for sale with a pool in Tarrytown, NY. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Tarrytown, NY agent, Jeremy Zucker specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Tarrytown, NY

$3,295,000
9 Beds ⋅ 5 Baths ⋅ 1047567 MLS
Gracing an impressive 4.28 acres overlooking the Hudson River, this exceptional nine-bedroom Tarrytown estate offers a rare combination of historic character, resort-style living, modern sophistication, and timeless elegance. Built in 1929 and affectionately known as Whitehall, the residence has been meticulously updated and maintained, preserving its architectural integrity while embracing the comforts, style, and expectations of today’s most discerning buyer. Spectacular water views span the entire home, providing an extraordinary backdrop for Hudson River sunsets. Distinctive gates mark the entrance to a private approach through beautifully landscaped grounds designed for a resort-caliber lifestyle, featuring a private pool and hot tub, expansive terraces, an impressive pool house with full kitchen, recreation room, steam and outdoor showers, private tennis court, tranquil pond, mature gardens, and winding stone paths. Inside the 8,329-square-foot haven, stained glass, arched openings, sweeping verandas, striking wood paneling, stately fireplaces, wrought-iron details, hidden doors, and other distinctive architectural elements preserve the home’s heritage, while thoughtful updates create a seamless blend of historic character and contemporary luxury. At the heart of the home is a magnificent, all-new kitchen with exquisite hand-selected quartz countertops, custom cabinetry, and top-of-the-line appliances. The generous floor plan offers gracious spaces for everyday living and entertaining, including a formal dining room, butler’s pantry, breakfast area, expansive screened porch overlooking the Hudson, and versatile spaces ideally suited for home offices or studies. All nine bedrooms are beautifully appointed, while the luxurious primary suite features a spacious ensuite bathroom with high-end finishes, a walk-in closet with custom built-ins, a meditative sitting room, a wood-burning fireplace, and a Juliet balcony with spectacular water views. New windows were recently installed complementing the home’s thoughtful updates, including beautifully refinished wood flooring, a reverse-osmosis water filtration system, and an eero mesh Wi-Fi system providing seamless whole-home connectivity. A sophisticated climate-control system with 17 HVAC zones provides year-round comfort throughout and a generator offers added peace of mind. A three-car garage, upper-level laundry, and expansive driveway add modern convenience. With direct access to the Old Croton Aqueduct and close proximity to Patriots Park, Wilson Park, Tarrytown Lakes, Tarrytown, and Sleepy Hollow, Whitehall is an unparalleled private Hudson River oasis offering a lifestyle of extraordinary beauty, privacy, and distinction.

57 Cobb Lane, Tarrytown
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 1017900 MLS
Welcome to 16 Stephen Drive, beautifully situated on .40 acres along a wide, picturesque street in the desirable Pennybridge neighborhood in Tarrytown, NY. This classic center hall Colonial offers generous space throughout in a wonderful setting with an exceptional backyard. A proper entry foyer sets the tone, opening to a gracious living room with wood-burning fireplace and a formal dining room. Continue through to the heart of the home, where the open, dine-in kitchen features crisp white cabinetry, quartz countertops, a Thermador range, Thermador refrigerator, breakfast bar and plenty of room for casual meals. A sliding glass door opens directly to the backyard patio, creating an easy connection to the heated pool and outdoors. Just beyond the kitchen, a cozy, tucked-away family room offers another comfortable place to unwind, while the side-entry mudroom with laundry and storage makes everyday living easy. Upstairs are three spacious bedrooms, including a generous primary suite with a bright, expansive primary bath with double vanity, large whirlpool style tub, and excellent closet space. Hardwood floors throughout, crown molding, wainscoting and two-zone central air add to the home’s classic appeal. Outside is where this property truly shines. The expansive, fully fenced backyard feels like a private retreat, complete with an in-ground heated pool and sport court. Backyard pickleball anyone? There's plenty of room to play and entertain, this is the yard where everyone gathers. An oversized two-car garage, connected to the mudroom by a covered breezeway, provides even more room for cars, bikes, gear and storage. All this in the Irvington School District, with Tarrytown’s vibrant shops, restaurants and waterfront close by. Enjoy Tarrytown recreation opportunities (tennis, pool, fitness center, parks), plus resident train parking and a 40-minute weekday express to Grand Central, while the nearby Old Croton Aqueduct trail offers miles of nature just moments from home. A special opportunity to bring your vision to a home with the space, setting and location you have been waiting for.

16 Stephen Drive, Tarrytown
$695,000
2 Beds ⋅ 2 Baths ⋅ 1040128 MLS
Welcome to Watch Hill of Tarrytown! This fully updated, turnkey townhome is ready for you to move right in. The inviting foyer provides convenient garage access and opens to a spacious living room, perfect for relaxing and entertaining. The exquisite kitchen is truly magazine-worthy, featuring high-end finishes, beautiful cabinetry, and stainless-steel appliances. The adjacent dining area leads to the sliding glass doors to a private patio and charming rock garden. A beautifully renovated half bath and laundry area complete the first level. Upstairs, the spacious primary bedroom offers both a walk-in closet and an additional closet, while the generously sized second bedroom provides plenty of room for family or guests. Beautifully appointed spa-like bathrooms complete the second level. Recessed lighting throughout, along with beautiful laminate and tile flooring, adds to the home’s fresh and modern vibe. A full crawl space provides excellent additional storage. The attached garage, private driveway, and ample guest parking offer exceptional convenience. Enjoy summer days at the community’s seasonal pool and take advantage of the close proximity to historic Tarrytown Village, with its wonderful selection of restaurants, shopping, entertainment, and Metro-North Railroad service for an easy NYC commute. Convenient access to major parkways and the Tappan Zee Bridge makes this an ideal location for commuters and those looking to enjoy all that Westchester has to offer.

204 Watch Hill Drive, Tarrytown
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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.