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Rye, New York Homes for Sale

The Town of Rye includes the villages of Rye, Port Chester, and Rye Brook, and is surrounded the Byram River and Long Island Sound, providing a picturesque panorama. Several major highways make Rye easily accessible to Connecticut and all points north, as well as New York City.

Rye is the oldest permanent settlement in Westchester County. It began in 1660 when Peter Disbrow, John Coe and Thomas Studwell came from Greenwich with a small group of settlers. They were joined by John Budd the following year. Their first treaty with the Mohegan Indians gave them the land between Milton Point and the Byram River (Peningoe Neck); then the mile-long “Manussing” Island. Within several years their combined purchases comprised all of what is now the City of Rye, Town of Rye, Harrison, White Plains, parts of Greenwich, North Castle, and Mamaroneck.

In 1665, Connecticut merged these settlements under the name of Rye after ancestors in Rye, England. In 1683, Rye was ceded unwillingly to the Province of New York by King Charles II as a gift to his brother, the Duke of York. But when a New York court severed the Harrison area from the settlement in 1695, the Rye colonists rejoined Connecticut in protest. In 1700, Rye again became part of New York by royal decree, this time permanently. The New York State Legislature officially established the Town of Rye boundaries in 1788. For two centuries, Rye remained a secluded community. Land was cleared for farming and cattle grazing. Docks were built on Long Island Sound, and oystering was an important occupation. Homes along Mill Town Road, now Milton, led to grist mills on Blind Brook.

In the late nineteenth century, Rye experienced its first real growth and change. The era of the trolley made surrounding communities accessible. By 1904, there were two schools, five churches, a library, and a lively population of 3,500 residents. As Rye developed, the residents began to desire complete independence from the Town government. City status offered many advantages, one being relief from paying a disproportionate share of the Town welfare tax. In 1940, the Legislature approved the Rye City Charter which was adopted by the residents 1,172 to 34. On January 1, 1942, Rye became Westchester’s sixth and smallest city.

Playland’s opened in 1928 and offered a waterfront area along the Long Island Sound. It was also a site of growing collection of recreational developments, including hotels, resorts and “amusement areas.” The original design included a boardwalk, ice-skating rinks, a swimming pool, and two beaches as well as amusement park rides. Some of those amusement park rides, such as the Dragon Coaster that serves as the park’s mascot, are still in use. The Dragon Coaster is one of roughly 100 wooden roller coasters still in operation in the United States. In 1987, Playland was declared a National Historic Landmark.

Today, the City of Rye is a unique blending of the old and the new. Now a residential, suburban community with every facility for modern living, it still retains its traditional atmosphere of tranquil village life as well as many historic landmarks that bind it to its three-hundred year history. Rye is primarily a place in which to live rather than to make a living. One-third of Rye’s working residents commute to New York City, 25 railroad miles away. Others are employed in Westchester, Connecticut, New Jersey, and Long Island as well as in the 200 small businesses and several large firms located here.

The Village of Rye maintains the feel of a quaint New England town, while at the same time, offering everything to the resident in the way of modern amenities. Its charming downtown is home to an eclectic mix of small shops, upscale eateries, as well as the Metro North station, providing convenient service for Manhattan commuters and weekend travelers. Beautiful, residential neighborhoods blend with estates to make this area so attractive.

The Rye City School District includes three National Blue Ribbon elementary schools of Excellence serving grades K-5. Rye Middle School, also a National Blue Ribbon School of Excellence, serves students grades 6-8, and Rye High School, ranked among the top high schools in the country by U.S. News and World Report and Newsweek Magazine, provides a full range of curriculum opportunities at Regents, honors and Advanced Placement levels for ninth through twelfth graders. The Rye School of Leadership, part of Rye High School, serves high school students who learn best in a non-traditional educational environment. The mission of the Rye City School District, in partnership with the community, is to ensure that every student is capable of becoming a life-long learner who can thrive in a global environment as a self-reliant and socially responsible citizen.

City of Rye: www.ryeny.gov
Rye City School District: www.ryeschools.org
Rye Neck School District: http://www.ryeneck.k12.ny.us/

 

Rye Homes for Sale

$9,250,000
4 Beds ⋅ 4 Baths ⋅ 925675 MLS
Rare waterfront opportunity offering both sunrise, sunset and a protected deep water dock! Enjoy panoramic vistas providing an incredible array of breathtaking water views. Perfectly situated, protected, bucolic 2.58 acres of natural beauty and over 200 feet of direct harbor waterfront. Whether you choose to renovate, build anew or pursue subdivision potential, explore the optionality. Site plan and surveys offer inspiration for potential subdivision or secure the perfect family compound close to all. Protected deep water dock that can handle multiple boats as well as existing marina offering 50 slips, only a 5 minute boat ride to the L.I. Sound. Enjoy a vacation lifestyle year round only 35 miles to Midtown, 5 minutes by car to town, train and all major highways. Unleash the value of this coveted location Where else can you experience a prime waterfront location with the opportunity to create your own dream home? Unique, like no other.

191 Kirby Lane, 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
$7,495,000
6 Beds ⋅ 7 Baths ⋅ H6317077 MLS
The pinnacle of turn-key modern luxury, this masterfully transformed 8,500+ SF estate delivers the ultimate resort lifestyle directly within the prestigious Westchester Country Club enclave, just 35 minutes from NYC. Effortlessly marrying classic architectural character with modern sophistication, light-filled living spaces are defined by intricate millwork, elegant arches, leaded glass, and warming Rumford fireplaces. The social heart of the residence is a bespoke designer chef’s kitchen featuring custom cabinetry, marble surfaces, and a dramatic teak entertaining island that flows seamlessly into an expansive great room overlooking serene grounds. The primary suite is an elevated sanctuary with high ceilings, a fireplace, boutique dressing room, and a spa bath with radiant heated floors and a steam shower. Designed for whole-body wellness and grand hosting, the lower level features a fitness gym, custom wine room, and dedicated pool baths leading out to sweeping stone terraces and an in-ground pool framed by a timeless slate roof and copper gutters. Complete with a three-car garage and private upper media lounge, this peaceful retreat offers unrivaled proximity to championship golf, tennis, vibrant village dining, premier schools, and express rail service to Manhattan.

19 Park Drive S, Rye
$6,995,000
7 Beds ⋅ 9 Baths ⋅ 1048484 MLS
Set high on 2.08 serene, private acres within the prestigious Westchester Country Club grounds (Rye PO / Harrison), this reimagined stone manor blends modern turnkey luxury with timeless architectural pedigree. Spanning 9,300+ SF of pristine, light-filled living space, the residence is curated for effortless everyday living and entertaining. The heart of the home is a culinary chef’s kitchen featuring a Carrara marble island, top-tier appliances, dual dishwashers, and a butler’s pantry, opening directly to an expansive coffered-ceiling family room with outdoor access to sizable deck and expansive grounds. Work from home in a quiet executive office or unwind in formal living room, framed by original leaded-glass doors and hand-hewn millwork. Upstairs, the vaulted primary retreat boasts custom closets, a spa bath with steam shower and radiant heat, a gas fireplace, and a private, screened sleeping porch capturing open views of the lush grounds. Designed for active wellness and recreation, the radiant-heated walkout lower level features a custom sauna, full bath, second laundry and flexible area ideal for lounge and fitness. For the automotive and sports enthusiast, an iconic porte-cochere leads to an extraordinary 4-car garage setup, in conjunction with a climate-controlled 3-car auxiliary garage. Complete with Marvin windows, energy-efficient systems, and elevator-ready access across all levels. An unmatched lifestyle location: tucked away in privacy, yet minutes to top-ranked public and private schools, downtown dining, golf, major highways, and a 40-minute commute to Manhattan. Move-in ready perfection.

4 Commodore Avenue, Rye
$5,395,000
5 Beds ⋅ 6 Baths ⋅ 941230 MLS
THE ULTIMATE MODERN MASTERPIECE. Brand new, complete, and meticulously engineered, this sleek farmhouse is a masterclass in high-performance luxury. Built for the buyer who demands "best-in-class" quality, this home features a low-maintenance James Hardie exterior, an Atlas Pinnacle Pristine roof, and professional-grade Marvin windows and doors. Inside, the engineering is unrivaled: a high-efficiency gas-fired boiler powers a 20-zone radiant heating system, ensuring silent, precision comfort in every room. The main level boasts 10' ceilings and wide-plank white oak floors. A breathtaking family room with soaring cathedral ceilings serves as the architectural heart, while the sleek chef’s kitchen features a waterfall quartz island and European cabinetry. A versatile first-floor bedroom/office and a custom-outfitted mudroom cater to modern lifestyle needs. The second level is a study in scale, headlined by a primary suite with custom closets and three additional ensuite bedrooms. The true "showstopper" is the massive 25x36 game room, offering endless possibilities for a home theater or golf simulator. The fully-equipped lower level is complete with a dedicated playroom, home gym, and wine cellar—offering the space, sophistication, and peace of mind today’s discerning buyer deserves! Outside, the completely flat, oversized backyard is a rare find, ready for a pool, sports court, and outdoor kitchen. Ready for homeowners now, this house is a must-see!

144 Wendover Road, Rye
$4,795,000
6 Beds ⋅ 6 Baths ⋅ 1024563 MLS
Introducing an iconic Milton Point treasure that best combines true architectural mastery alongside a coveted waterfront location. This stunning Victorian has been fully renovated, expanded and thoughtfully improved, inside and out, sparing no expense to preserve and enhance the historic details now blended perfectly with all imaginable modern amenities. An unreplicable home in a premier Rye location, offering partial water views and shared deep water dock. A rare find not to be missed.

731 Forest Avenue, Rye
$4,595,000
6 Beds ⋅ 6 Baths ⋅ 1048123 MLS
Spectacular transitional home, custom built in 2023 with the highest level of craftsmanship and attention to detail by esteemed local developer, Landmark Construction. Sun filled rooms with 20 foot vaulted ceilings and a continuous wall of glass provides a stunning view of the idyllic landscape. The open floor plan features a gorgeous 10 foot island that bridges the living room with gas fireplace and the dining area and includes a state of the art sound system making it perfect for entertaining. Outdoors is a covered heated kitchen with entertainment system, leading to an extensive bluestone patio with an outdoor wood-burning fireplace and salt water hot tub. The main floor includes a bedroom with en suite bath and an office. Upstairs is a primary suite, with spa bath and 2 WICs, a bedroom with en suite bath, 2 bedrooms, hall bath and laundry. The lower level with high ceilings, expansive recreation area with multi media walls, custom bar, gym, bedroom and full bath complete this dream home.

9 Kirby Lane N, Rye
$4,480,000
6 Beds ⋅ 10 Baths ⋅ 1004420 MLS
A rare convergence of privacy, scale, and effortless sophistication, this commanding Contemporary Colonial stands behind its own gated entry on 1.47 manicured, fully fenced acres. Located 23 miles from midtown Manhattan and moments from the storied grounds of Westchester Country Club, this one-of-a kind home offers privacy and tranquility, just 1.5 miles from the Rye train station, boutiques and dining. Soaring 10-foot ceilings and a dramatic 21-foot double-height living room set an architectural tone of quiet grandeur from the moment you arrive. Six ensuite bedrooms, including a main-floor second primary suite with spa-inspired bath, offer privacy at every turn, ideal for multi-generational living or distinguished guests. A media room, fully renovated chef's kitchen, newly built recreation room and whole-house Sonos system complete an interior conceived for both grand entertaining and unhurried everyday living. Outside, a private resort campus completed in 2020 anchors the grounds: a heated saltwater pool and spa, professional outdoor kitchen, two designer cabanas, and a tranquil cascading waterfall create a sense of year-round escape. Below grade, a finished lower level unfolds as a world unto itself, complete with a home gym, custom bar and multiple entertaining areas. An oversized three-car garage and full-house generator round out an offering defined by both luxury and ease — with taxes that significantly undercut comparable estates.

23 Pheasant Drive, Rye
$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
$3,650,000
5 Beds ⋅ 5 Baths ⋅ 1047867 MLS
Set well back from the road on 1 private acre, this home offers a sense of space and seclusion rarely found in the heart of Rye. Generously scaled rooms define the main level, beginning with a gracious front-to-back living room and a dining room where textured walls and a statement chandelier add character. The family room is centered around a distinctive stone fpl and flows naturally into the 2023 renovated custom kitchen by renowned JWH Design & Cabinetry, complete with a breakfast area, island & top-tier appliances. Large windows and doors throughout these primary living spaces bring in abundant natural light and open to the rear patio, creating a wonderful connection between the interiors and the surrounding property. A newly designed JWH mudroom and laundry room off the kitchen bring the same attention to detail to everyday living. Upstairs, the primary suite offers a spa-like ensuite bath and generous WIC. Four add’l bedrooms, one with an ensuite, are bright and well proportioned, with excellent closet space and a well-appointed hall bath w/double vanity completes the space. The expansive lower level with a full bath adds another dimension to the home, with a flexible layout ready for recreation, media, play and entertaining. Recent updates include a new roof and HVAC units, new lower-level flooring, refinished hardwood floors, fresh interior paint, new carpeting on the stairs and second floor, and new window treatments throughout. What truly sets this property apart is its exceptional setting. Tucked back on a private acre, the home feels wonderfully removed while remaining within walking distance of the train, schools, parks and downtown Rye. An oversized rear patio framed by a stone wall extends the living space outdoors, creating an inviting spot for alfresco dining and entertaining. It’s a rare combination of privacy, space and in-town convenience.

140 Grace Church Street, Rye
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