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$4,400,000
8 Beds ⋅ 8 Baths ⋅ 1031136 MLS
A truly rare opportunity in Rye. Set on nearly 5 spectacular, estate-like acres in the Rye City School District, this is one of those properties that simply cannot be replicated today. The breathtaking grounds create a private retreat complete with an in-ground pool, expansive lawns, mature landscaping, and endless space to entertain, relax, or play. At the heart of the outdoor experience is an exceptional pool house that lives like a true second home—a pristine, newer residence featuring approximately 1,600+ square feet, three bedrooms, three full baths, a beautiful modern kitchen, spacious living area with fireplace, and covered patio overlooking the pool. Whether used for extended family, guests, an au pair, home office, or multigenerational living, it is a remarkable amenity rarely found at this level. The stately Colonial offers nearly 5,000 square feet with an outstanding floor plan, generous room sizes, sun-filled living spaces, a grand foyer, formal living and dining rooms, private office, spacious family room with stone fireplace and wet bar, sunroom, and five bedrooms including a gracious primary suite. The home has been meticulously maintained and presents the perfect opportunity to update and customize to your own style while preserving its exceptional layout and timeless character. An added bonus—and a major value enhancement—is the property's new connection to public sewer, eliminating one of the biggest concerns associated with estate properties while providing long-term peace of mind. Just minutes from downtown Rye, beaches, parks, marinas, restaurants, Metro-North, and award-winning Rye City Schools, this is a once-in-a-generation opportunity to own an estate-sized property with a true second residence in one of Westchester's most sought-after communities. Properties offering this combination of acreage, privacy, flexibility, and location are extraordinarily rare.

415 Grace Church Street, Rye
$7,995,000
6 Beds ⋅ 6 Baths ⋅ 1015115 MLS
Tucked away at the end of a long private drive, hidden from view and unknown to many who pass nearby, this extraordinary waterfront estate offers a rare combination of privacy, history, and lifestyle in one of Rye’s most coveted neighborhoods. Originally built in 1856 as part of the area’s original homestead and thoughtfully expanded and enhanced over the years, the property spans 1.59 spectacular acres along Milton Harbor with direct access to Long Island Sound. A world apart from the ordinary, the 5,233-square-foot residence is surrounded by breathtaking gardens, mature specimen plantings, and a series of enchanting outdoor spaces that unfold from one destination to the next. Multiple terraces invite al fresco dining and entertaining—from morning coffee overlooking the water, to sunset cocktails by the pool, to gatherings at the dock as boats return from a day on the Sound. With six bedrooms, five full and one half baths, four garage bays, a waterside pool, and a private dock accommodating a vessel up to approximately 32 feet, the property delivers an unrivaled waterfront lifestyle. The setting evokes a distinctive “Bedford meets the water” feel—an uncommon blend of estate-like grounds, privacy, and natural beauty rarely found on the shoreline. While the home enjoys all the benefits of the vibrant Hix Park neighborhood community, it lives as its own private sanctuary. This is not a cookie-cutter property. It is for the buyer seeking something truly unique: a place with history, character, extraordinary land, stunning gardens, a dock, pool, water access, and a sense of discovery that cannot be replicated.

87 Hix Avenue, Rye
$7,995,000
6 Beds ⋅ 7 Baths ⋅ H6317077 MLS
A rare opportunity to own one of Westchester Country Club’s most elegant estates- a completely renovated, move-in ready 1926 Tudor that effortlessly marries storybook charm with modern luxury. Boasting over 8,500 square feet of masterfully renovated living space, this residence seamlessly blends historic architectural character with modern sophistication, offering a rare opportunity for refined suburban living. Enter through a grand foyer into formal living spaces defined by intricate millwork, elegant arches, leaded glass windows, and Rumford fireplaces. The spacious dining room flows effortlessly into a designer chef’s kitchen, featuring custom cabinetry, marble countertops, a Wolf six-burner range with pot filler, a Sub-Zero refrigerator/freezer, and a built-in pantry. The massive teak center island is ideal for entertaining, complete with a Sub-Zero wine refrigerator and cooling drawers. Adjacent, the expansive family room is bathed in natural light, with custom woodwork and a grand fireplace, overlooking serene estate grounds. The private primary suite is a sanctuary of luxury, with high ceilings, a fireplace, custom closets, and a spa-inspired bath with radiant heated floors, tumbled marble, soaking tub, steam shower, and dual vanity. Additional bedrooms are generously sized with high ceilings and elegant finishes, complemented by beautifully appointed baths. The lower level offers a world-class retreat, including a well-equipped gym, custom wine room, an additional bedroom, two full baths with direct pool access, and abundant storage. Outdoor living is equally spectacular, with an expansive patio, in-ground pool, and meticulously maintained grounds framed by the estate’s timeless slate roof and copper gutters. A three-car garage with a bonus/media room completes this extraordinary property. Located in one of Westchester’s most desirable enclaves, 19 Park Drive South provides unparalleled privacy, proximity to world-class amenities, and effortless access to New York City via Metro-North and major parkways. Whether enjoying the serene estate, hosting elegant gatherings, or taking advantage of the Westchester Country Club’s prestigious grounds, this home embodies the ultimate luxury lifestyle.

19 Park Drive S, Rye
$3,495,000
6 Beds ⋅ 11 Baths ⋅ 911637 MLS
Major reduction . Home owner wishes to move on. Nestled on over two acres of secluded, picturesque grounds, this exceptional, one-of-a-kind contemporary estate is a rare opportunity for luxury living. It boasts a stunning pool with hot tub ,waterfall, a pavilion with full bath and changing rooms, and a tennis court. The striking architecture seamlessly blends indoor and outdoor living. Expansive spaces are accentuated by soaring ceilings and glass walls, creating the perfect environment for intimate gatherings and large-scale entertaining. The home offers every imaginable amenity, ensuring a lifestyle of comfort and elegance. This beautifully constructed and maintained residence offers modernized heating and air conditioning systems, ensuring optimal comfort year-round. The pool and tennis court have been meticulously maintained. near downtown Rye, shops and restaurants, and Harrison, White Plains, and Greenwich, easy commute to NYC. Come and visit 40 Poly Park Road. Additional Guest Quarters, Tennis, 3 Car Attached, extra parking

40 Polly Park Road, Rye

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.