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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
$7,995,000
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
$5,995,000
6 Beds ⋅ 7 Baths ⋅ 915702 MLS
A rare offering in Rye: a newly constructed residence of exceptional scale and craftsmanship, graced with sweeping golf course views. Set on 1.37 acres, this 7,584 sq. ft. home is unlike anything else on the market, offering modern innovation on one of the most coveted private roads in Rye. The dramatic entry hall, crowned by a 21-foot ceiling and anchored by a Venetian plaster fireplace, introduces interiors of remarkable light and proportion. Expansive Marvin windows frame the verdant vistas, while wide-plank white oak floors and refined architectural detailing lend a sense of understated sophistication throughout. At the heart of the home, the kitchen showcases DOCA cabinetry imported from Spain, professional-grade Wolf and Sub-Zero appliances, and a full scullery enclosed by steel-and-glass doors. A butler’s pantry and bespoke dining room cabinetry further elevate the entertaining experience. Six ensuite bedrooms include a first-floor guest suite and a magnificent primary retreat with a private terrace, dual custom closets, and a spa-inspired Porcelanosa bath with radiant heated floors. The lower level offers a generous family room with bar, private guest suite, and space prepared for a golf simulator and/or home theater. Outdoors, a stone terrace and level grounds—engineered to accommodate a future pool—create endless possibilities for leisure and entertaining. Additional features include a full Sonos and Lutron lighting system, radiant-heated bathrooms, multiple laundry rooms, and a standing seam metal roof. A smart-home security system, mudroom, and three-car garage provide both convenience and peace of mind. A home of rare distinction, 11 Boxwood Lane pairs new construction with an unparalleled setting—an extraordinary opportunity in the heart of Rye. *Image of pool is a rendering of potential pool site. Plans were approved by town*

11 Boxwood Lane, 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
$4,795,000
6 Beds ⋅ 6 Baths ⋅ 1021670 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 porch with kitchen and 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
$4,550,000
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 without sacrificing proximity to the city. 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, and whole-house Sonos 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
$4,495,000
7 Beds ⋅ 10 Baths ⋅ 873606 MLS
$15 Million Dollar value being sold in an estate sale for an amazing price! Unrivaled grandeur with an idyllic Tuscan-countryside vibe! Introducing one of Westchester County’s most magnificent Estates, beautifully situated high on an exquisite tree-lined rise just minutes from Rye. This private sanctuary is nestled on 5.2 acres of manicured grounds with distant water views of Long Island Sound. There’s nothing quite like it: an infinity pool, pool house, guest house, indoor-outdoor jacuzzi, sauna, sun-drenched patios, clay tennis court, bowling alley, gym, wine cellar and a seven-car garage. The possibilities are endless! A masterpiece of design, this stunning residence features a soaring 40-foot-high central atrium with a barrel-vaulted ceiling and a suspended walkway. Bathed in natural light from towering walls of glass, this home unfolds gracefully over 4 levels. It offers a welcoming reception room, a stately library, grand living room, a chic dining room and a spacious executive office with built-ins. Multiple rooms open to a glorious rear patio with built-in grill including the chef’s kitchen, sunny breakfast room and the breathtaking Great Room with wet-bar and one of this home’s four fireplaces. The main residence boasts 7 bedrooms, 8 full bathrooms and 2 powder rooms. The primary suite is one-of-a-kind with a stunning private sundeck, 2 marble ensuites and a myriad of boutique-like dressing rooms and closets. Nothing has been overlooked - there’s an elevator to all floors, 2 laundries, and a heated driveway for snow melt. This prestigious Estate is minutes from downtown Rye, convenient to Metro-North train and highways to NYC!

7 Rockledge Road, Rye
$3,995,000
6 Beds ⋅ 5 Baths ⋅ 1027898 MLS
A rare offering in the heart of Rye in sought after Beaumont Park~ perfectly positioned in one of Rye's most coveted "in-town" neighborhoods, this exceptional 6 Bedroom, 4.1 bath colonial offers GENEROUS everyday living space on both the first and second floors with high ceilings; offering a rare three car garage. This proud Center Hall Colonial offers an uncommon combination of refined elegance, generous scale, and peaceful privacy. Just steps from downtown Rye, top rated schools, parks, restaurants, and the train, the home enjoys a premier location while feeling like a secluded retreat, surrounded by mature trees and lush landscaping defined by stone walls and patios, and last but not least, established hydrangeas ~ a slice of Nantucket in your very own backyard :). Features a coveted first floor study and a first floor en-suite bedroom which provides ideal accommodations for a guest, multigenerational living, au pair, or an additional home office. Options galore! This home combines timeless architecture and exceptional craftsmanship~ from its stone patios, inviting circular driveway, to it's lead coated copper gutters and so much more. Pure sunset bliss from your own backyard :))

21 Loder Street, Rye
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