Nestled in the heart of Rye's coveted Greenhaven waterfront community, with DEEDED RIGHTS TO THE PRIVATE BEACH AND PIER located just steps away - at the end of the street, minutes from Greenwich, this exceptional 5-bedroom, 5.1 bathroom residence offers an extraordinary opportunity to enjoy luxury living in one of Westchester County's most prestigious neighborhoods. Situated on an expansive half acre lot, this lovingly maintained home boasts 3,804 square feet of beautifully designed living space, which does not include the lower level offering an additional 1300 sq ft of endless potential possibilities for recreation, a home gym, media room, guest quarters, or multigenerational living. Built in 1988, the home showcases a timeless brick colonial design with spacious, light-filled rooms, gracious entertaining spaces, and a seamless flow ideal for both everyday living and elegant gatherings. The generous floor plan offers oversized bedrooms, multiple living and entertaining areas with fireplaces. Outside, the level landscaped grounds create a private retreat with plenty of room for outdoor entertaining, or the addition of a pool. Set on over half an acre in the sought-after Greenhaven neighborhood, you'll enjoy a serene residential setting and moments from Milton Harbor, marinas, parks, beaches, and scenic waterfront walks. Residents appreciate Greenhaven's unique waterfront lifestyle while remaining just minutes from downtown Rye's vibrant restaurants, boutique shopping, Metro-North station, award-winning schools, and major highways, providing an effortless commute to Manhattan. House has been updated with new forced air heating system/central air and new H/W heater.

90 Greenhaven 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

$3,095,000

3 Beds ⋅ 4 Baths ⋅ 1022311 MLS

Public Remarks Experience unparalleled luxury at The St. Regis Residences, Rye, an exclusive 55+ condominium community offering legendary St. Regis service and world-class amenities. This rare three-bedroom, three-bath patio residence features a gracious open floor plan with seamless indoor-outdoor living and direct access to a private patio. Elegant finishes include contemporary Italian kitchen and bath cabinetry, stone and quartz countertops, a spa-inspired primary bath with heated floors, Kohler fixtures, a gas fireplace, hardwood and stone tile flooring, oversized windows, Sub-Zero, Wolf, and Bosch appliances, a wine refrigerator, spacious walk-in closet, and a private butler's closet. Residents enjoy exceptional amenities including full-service staff, three club rooms, an indoor pool, fitness center, screening room, golf simulator, and beautifully landscaped grounds with walking paths, water features, outdoor fire pits, and flowering gardens. Experience the ultimate in luxury, comfort, and convenience in one of Rye's most prestigious residential communities.

120 Old Post Road Unit #C107, 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

$1,650,000

1010775 MLS

Attention Investors, Developers & Those Who Want to Build Their Dream Home in One of Westchester's Most Coveted Areas! IMAGINE: A blank canvas to build your dream home in the prestigious enclave of Rockledge Road. Private, yet convenient to downtown Rye and nearby White Plains. Fans of Apple TV's FRIENDS and NEIGHBORS might recognize this exclusive, tree lined street! Easy access to major highways and Metro North Rye train station. Close to highly acclaimed Rye Country Day School and world renowned Westchester Country Club. Take control of your lifestyle! Be creative, add beauty and live life on your own terms! Make your appointment today!

15 Rockledge Road, Rye

$1,795,000

4 Beds ⋅ 5 Baths ⋅ 1008360 MLS

NEW 4 bedroom 4.5 bath townhome in the city of Rye close to all. This home features over 2,800 sq feet of living space with an open floor plan, The main level has a beautiful kitchen with large center island, stainless steel appliances, quartz countertop and backsplash, living room with fireplace, powder room, and sliding glass doors to a private deck overlooking the back yard. The second floor has a magnificent primary bedroom with a full bath, and spacious closets, 2 additional bedrooms, a hall bath, and washer/dryer. The 3rd level has a 4th bedroom, family room and a full bath, it can also be utilized as a private office, guest suite, or additional play area. The lower level is a large finished recreational room, with a gym, a full bath, natural light, and high ceilings.

86 B Maple Avenue, Rye

$1,795,000

4 Beds ⋅ 5 Baths ⋅ 1008358 MLS

NEW 4 bedroom 4.5 bath townhome in the city of Rye close to all. This home features over 2,800 sq feet of living space with an open floor plan, The main level has a beautiful kitchen with large center island, stainless steel appliances, quartz countertop and backsplash, living room with fireplace, powder room, and sliding glass doors to a private deck overlooking the back yard. The second floor has a magnificent primary bedroom with a full bath, and spacious closets, 2 additional bedrooms, a hall bath, and washer/dryer. The 3rd level has a 4th bedroom, family room and a full bath, it can also be utilized as a private office, guest suite, or additional play area. The lower level is a large finished recreational room, with a gym, a full bath, natural light, and high ceilings.

86 A Maple Avenue, Rye

$1,525,000

1008303 MLS

Beautiful, elegant, community fully developed, Well established homes and landscaping throughout the entire community. A dream spot to build your once in a life time home. Close to town and parkways .

20 Mt. Holly, 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

$1,539,500

4 Beds ⋅ 2 Baths ⋅ 988403 MLS

Lovely Coonial Homewalk to Beach & Park & Schools: Midland Elementary School & Rye High. Winter Water View on tree lined street. House is larger than appears in listing. Livingroom, Formal Diningroom, Den, Home Office/Playroom, 4 Bedrooms. Cute EIK. Hardwood Floors, Ceramic Tiles. Dry painted Large basement with new oil tank & door to garden. NO flooding & no flood insurance required. Lots of Flowering Trees. Two large car Garages.

15 Roosevelt Avenue, Rye

$3,295,000

6 Beds ⋅ 6 Baths ⋅ 986082 MLS

Stunning New home in a great location within walking distance to the Rye train station and town. This well designed 1st floor features an open floor plan with an eat in kitchen, large center island, family room with fireplace, living room, dining room, private study and powder room. The second floor has a large Primary bedroom suite with a vaulted tray ceiling, custom finished walk in closets, and marble bath with a heated floor. Four additional bedrooms, 2 en/suite with a private bath, a hall bath, and laundry room complete the 2nd floor. The lower level is finished with a recreation room, bedroom, full bath and mud room. Other amenities include high efficiency heating and cooling system, custom transitional moldings, maintenance free exterior, 9 ft ceiling, custom craftsmanship and detail throughout by long time local Westchester developer. House will be completed by the end of the 2026 still time to customize and make it your own.

233 Highland Road, 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

Homes for Sale in Rye City, NY Between $5,00,000 to $25,000,000

All Rye City, NY Homes for Sale Between $5,00,000 to $25,000,000

Jeremy Zucker, ABR, RENE, SRES

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