333 houses for sale in Rye Brook

Unique and charming, this Sears kit home, model Collingwood from 1927, brings one back to a by-gone era. Located in the Pemberwick neighborhood, this unique home features beautiful woodwork and simple beauty. This inviting property is very near Pemberwick Park, offering direct access to tennis courts, baseball fields, basketball courts, open green space and nature trails - perfect for active lifestyles. This home blends timeless character with modern comfort, ideal for buyers seeking community, convenience and charm. Opportunity to add value to a classic home in a serene setting with unbeatable recreational access. Close proximity to schools. Fenced in yard, perfect for a garden

Wonderfully updated family Colonial in private King Merritt, set on 1.39 acres in Greenwich. Offering nearly 5,300 square feet of living space, this 4-bedroom, 4-full-bath home features a spacious, light-filled layout with multiple living areas ideal for everyday living and entertaining. The updated kitchen serves as the heart of the home, while a large private office with beautiful custom built-ins provides an impressive work-from-home setting. Generously proportioned rooms, multiple fireplaces and a three-car garage add to the home's appeal, while the beautifully situated property offers exceptional privacy. Convenient to Glenville, schools, shopping, dining and major commuting routes. First and second floor +/- 3,935 square ft. Lower level +/- 1,327 square ft of finished space

The best of brand-new living! Set on 1.4+ beautifully level acres in Greenwich's coveted Bailiwick Association, this 5,400+ SF custom transitional Colonial offers exceptional craftsmanship, extraordinary natural light and the ease of move-in-ready living. A welcoming front porch opens to a dramatic double-height foyer, while elegant living and dining rooms feature custom millwork, soaring ceilings and walls of sliding glass doors leading to expansive decks and patios. At the heart of the home, a stunning chef's kitchen with double islands, Sub-Zero and Wolf appliances, and a butler's pantry opens to a sun-filled vaulted breakfast area and family room. A first-floor ensuite bedroom with deck access, mudroom and two powder rooms complete the main level. Upstairs, the luxurious primary suite features vaulted ceilings, a gas fireplace, two walk-in closets and a marble bath with double vanities and an oversized rainfall shower. Four additional bedrooms, three full baths, an office, sitting

A striking expression of modern luxury, 8 Hickory Drive delivers sophisticated design, exceptional craftsmanship and high-end finishes across four beautifully finished levels. Set on 0.8 acres, the home pairs dramatic, light-filled living spaces with effortless indoor-outdoor flow. A deluxe chef's kitchen anchors the main level with open concept living to family room with fireplace. The primary suite is spacious and romantic with large walk in closet and spa bathroom. Four additional spacious bedrooms offer refined comfort and privacy. The finished third floor provides flexible space for work or retreat, and the lower level impresses with a private theater, gym and recreation spaces. Every detail has been thoughtfully considered, creating a home that feels extraordinary

Original farm house (unit 1) was renovated in 2018. The tiled entry leads to the family room w adjoining dining room and full bath. Kitchen features modern white cabinets, quartz countertops, stainless steel appliances and separate pantry. Second floor features a landing leading to the bedroom with ensuite bath and large office/WIC. Separate laundry area and door to access the rear yard. 3rd floor has bonus finished attic space. Unit 2 (rear) was built in 2023. First floor comprises a family room, kitchen with quartz countertops, stainless steel appliances, mudroom, 1/2 bath, separate pantry and door to rear yard. The second floor features a bedroom with luxurious ensuite bathroom, WIC with laundry. Third floor has bonus finished attic space Landscaped front, side and rear yard

Set on 3.13 acres just off Round Hill Road, 8 Sheffield Way brings Modern Greenwich Living to one of Greenwich's most desirable mid-country locations. Here, striking architecture and warm, inviting interiors set the scene for sunlit mornings, long dinners with friends and evenings that drift onto the terrace, with the quiet of the woodland beyond. Davis Chase Homes will build your home, and you can work with Workshop/APD to further personalize the design, finishes and amenities. The current design encompasses approximately 9,500 square feet above grade, including the three-car garage, plus a fully finished lower level featuring a private wellness center and dedicated entertainment spaces. The home offers seven bedrooms in all, including six en-suite, seven full baths and three powder room A dramatic double-height central living hall frames views through the home to the backyard, while an expansive kitchen opens directly to the family room. A separate dining room, library, main-floor gu

Set high on two exceptional acres in the coveted Golden Triangle, this custom-built home offers a great lifestyle just minutes from town and schools. The sun-filled six-bedroom residence features 10-foot ceilings and is designed for effortless indoor-outdoor living. Elegant formal rooms, casual living spaces, a gourmet eat-in kitchen, and family room open to an expansive terrace with an outdoor fireplace and built-in grill. The beautiful pool overlooks magnificent grounds designed for recreation and entertaining. A vaulted second family room, first-floor office, and separate au pair suite provide flexibility, while the third-floor playroom and walk-out lower level with cabana bath, wine room, gym, two laundry rooms, and new roof complete this remarkable Round Hill property

2026 NEW CONSTRUCTION - CAN FULLY CUSTOMIZE AT THIS STAGE - Set on 4.35 private and quiet acres in backcountry Greenwich, this modern farmhouse offers over 10,000 sq ft of refined living. Designed for today's lifestyle, the home blends classic architecture with modern accents -steep gables, expansive windows, and natural stone accents. Light-filled interiors feature 6 en-suite bedrooms, 8 full and 2 half baths, soaring ceilings, and custom finishes. The chef's kitchen with professional-grade appliances opens to multiple living and dining spaces. Outside, a heated Gunite pool, spa, and outdoor fireplace create an effortless indoor-outdoor flow. Every detail reflects modern luxury and timeless design, minutes to Greenwich town and schools as well as easy proximity to Westchester and NYC. Photos are renderings. 2026 NEW CONSTRUCTION - CAN FULLY CUSTOMIZE AT THIS STAGE. Specs subject to change

A rare offering where timeless architecture, exceptional scale and resort-style living come together in a spectacular private setting. Designed for both gracious entertaining and everyday living, this classic expansive residence offers beautifully proportioned interiors, multiple gathering spaces and a seamless connection to the outdoors. The heart of the home features a spacious eat-in kitchen opening to the breakfast area and family room with fireplace, while elegant formal living and dining spaces provide an ideal backdrop for entertaining. A private office, generous bedroom accommodations and an expansive primary suite with dual walk-in closets and dual spa-like baths complete the thoughtfully designed interiors. The exceptional grounds create a true private retreat. A stunning pool and expansive terraces are surrounded by mature specimen trees, lush landscaping and sweeping level lawn. At the center of the outdoor experience is an extraordinary four season pool house, a destinatio

Ideally located in the heart of Old Greenwich, just moments from the train, village shops, restaurants, and Binney Park, this sophisticated Colonial-style farmhouse offers an open, airy floor plan designed for modern living. High ceilings, detailed moldings, and hardwood floors create timeless appeal throughout. The gourmet kitchen with marble countertops flows seamlessly into the family room, providing the perfect space for everyday living and entertaining. The finished lower level features a media room, recreation space, and flexible bedroom, gym, or office. Outside, enjoy a spacious level backyard and deck. A rare opportunity in one of Old Greenwich's most sought-after neighborhoods

Enjoy the best of Old Greenwich living in Shorelands, a private waterfront association ideally located near the Village's restaurants, shops, schools, parks, train station, and Greenwich Point Beach. This beautifully updated three+ bedroom home offers an inviting blend of comfort and coastal charm. Residents enjoy access to the association's private beach and dock, perfect for summer watersports, relaxing by the water, and socializing at neighborhood gatherings. This home offers an exceptional lifestyle in a coveted waterfront community. Not included in sq. footage is partially finished basement. (Totals around 2800 sq. ft.)

A rare opportunity to own an authentic Mid-Century Modern home set on 2 picturesque, private acres in a quiet sought-after neighborhood of Cos Cob. This contemporary residence presents endless possibilities-move right in or create your dream estate. One-level living showcases the timeless appeal with oak floors throughout, featuring soaring ceilings, expansive windows, and sun-drenched living spaces that seamlessly connect with the surrounding landscape. Nestled in complete privacy, this architectural gem is designed to bring the outdoors in. The dramatic living room is anchored by a wood-burning fireplace and opens to an expansive deck overlooking the tranquil backyard perfect for a pool! A truly special setting offering privacy

Welcome to 61 Center Drive, a move-in-ready Old Greenwich home at the end of a cul de sac. Thoughtfully updated across two levels, this 5-bedroom, 3-full bath home offers approximately 2,300 square feet with bright gathering spaces, renovated finishes, and multiple areas to work, host, or just relax. The main level features hardwood floors, a newly updated kitchen that easily flows into a spacious dining and living room overlooking the foyer with generous natural light. Three bedrooms and two newly renovated full bathrooms complete this level. The finished lower level adds meaningful versatility with a spacious bedroom, renovated full bathroom, fireside recreation room, and an additional flex room that can function as a bedroom, office, gym, or playroom

Set on a private, gated 1.6-acre waterfront point in Old Greenwich, this charming Shore Colonial captures beautiful water views and spectacular sunsets. Freshly painted and thoughtfully refreshed, the 5,351-square-foot home offers 5 bedrooms, 5 full and 1 half baths, and water views from nearly every room. Classic architectural details lend timeless character to gracious living and dining spaces. The spacious kitchen opens to the family room, while French doors lead to a covered porch for relaxing and entertaining. Expansive grounds lead to a private dock, and an elevated widow's walk offers panoramic shoreline views. An exceptional blend of charm, privacy and waterfront living. Also available for rent

Embrace the Old Greenwich lifestyle in this beautifully updated 4500 sf home. Set back on a quiet street in a desirable neighborhood, the house was thoroughly remodeled in 2000 and has received continuous high-end updates. A sun-filled, double-height foyer flows into open spaces, including a fully renovated custom kitchen and dining room. The main floor upstairs features 4 spacious bedrooms, a newly renovated primary bath and a private office. Downstairs a spectacular family room with custom wet bar opens to an expansive outdoor deck and private level yard overlooking Binney Park Nature Trails. Enjoy peace of mind with an elegant stone facade, renovated siding, twin new high-efficiency HVACs, and an EV charger. All this within easy reach to the park, train, and top schools

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree unobstructed water views from every bedroom and living space, with beautiful NYC skyline views. Designed for modern coastal living, the home spans three levels with six decks and seamless indoor-outdoor flow. Walls of glass and Nano folding doors open the main level directly to the water, leading to a newly built private dock ideal for boating and entertaining. The interior features 5 bedrooms, 5 full baths, and 2 powder rooms, with wide 10-inch plank floors throughout. The chef's kitchen is centered around a 22-foot quartz island and equipped with Wolf and Sub-Zero appliances, including double ovens, double dishwashers, and additional refrigerated drawers. A third-floor full kitchen offers added flexibility for guests or extended living. Spa-like baths include Lusso Stone fixtures, heated floors, towel warmers, and a

Opportunity awaits in one of Greenwich's most desirable communities. Located on a quiet residential street in Cos Cob, this spacious home offers 3,597 square feet of living space across two levels, featuring 4 bedrooms and 3 full bathrooms. A new roof and recently painted interior provide added value, while the generous floor plan offers exceptional flexibility for today's lifestyle. The generous footprint provides exceptional flexibility for modern living, entertaining, or future customization. Enjoy the benefits of Greenwich ownership, including access to top-rated schools, parks, beaches, and convenient proximity to Cos Cob village, Riverside, Old Greenwich, Metro-North, and major commuting routes. A rare chance to secure a substantial home in a sought-after Greenwich location

Experience exceptional new construction by Build Casa Tua on Halsey Drive. Spanning four finished levels, this home blends timeless architecture with modern luxury. A dramatic double-height foyer opens to sun-filled living spaces with soaring ceilings, wide-plank white oak floors, and walls of glass leading to a covered deck and private fenced backyard. The custom white oak kitchen features Thermador appliances, quartz countertops, bespoke cabinetry, and a walnut wet bar. Five en-suite bedrooms include a luxurious primary suite with vaulted ceilings, heated bath floors, and a steam shower. Ideally located near Riverside Commons, Metro-North, beaches, downtown Old Greenwich, parks, and top-rated schools

A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one of Old Greenwich's most sought after waterfront settings. The.28 acre property sits within a private association that includes sandy beach access, a boat launch ramp for paddle boarding, kayaking and boating and a large communal waterfront lawn. The current home features a large living room with direct Sound views, a formal dining room, a kitchen and family room opening to a stone patio facing Long Island Sound, and a primary bedroom suite with private bath. Three additional bedrooms and full bath occupy the upper level, sharing the same water views. Gas heating, central air conditioning and an attached 2-car garage are in place. A beautiful and serene location in a private waterfront association, Long Island Sound views and steps to Tod's Point - all within minutes of the Old Greenwich train station, Old Greenwich sh

Discover the timeless appeal of Old Greenwich in this beautifully restored 1910 barn, tucked away off West End Ave in this incredibly convenient and private location. Soaring ceilings, wide-plank floors, and light-filled interiors create a fresh and original space. In the country kitchen a fabulous Aga oven anchors the space truly creating the heart of the home. Multi-access to a large wrap-around deck, overlooking beautifully landscaped gardens and level yard. An oversized one-car detached garage with extra storage and ample courtyard parking. This lovely tucked away gem is moments from the village, train station, schools, shops, restaurants and the popular Tod's Point Beach. A rare offering that captures the charm of Old Greenwich while enjoying the best of outdoor coastal living

Idyllic south of the village location in coveted Shorelands Association offers deeded private beach and dock rights, perfect for kayaking/boating, and a sprawling five-bedroom Colonial. Set on a level.26 acre just one house in from the water on a quiet yet convenient cul-de-sac providing very easy access to shopping, dining, trains and schools and a short distance to Tod's Point. Enjoy this house as is or renovate to create your dream coastal destination. Generous 2,762 sq. ft. floor plan features a large eat-in kitchen, dining room, den/office and family room with fireplace, access to a huge deck which spans the length of the house. Half bath, mudroom and attached two-car garage round out main level. Second floor boasts primary suite, four bedrooms, two full baths and half bath

Unique opportunity to own a charming multi-unit property with a separate cottage. The main house features a welcoming wraparound porch and is currently configured as a two-family home, with the option to convert it back to a single-family residence. The cottage offers flexible possibilities as an accessory dwelling unit, guest house, or income-producing rental. The possibilities are endless. Recent updates include a newer roof and siding, and central air throughout. Set on a level 0.2-acre lot, the property is conveniently located near the train station, Binney Park, and the village

Exquisite Center Hall Colonial home situated on the apex of a quiet circular lane in sought after Riverside neighborhood. Constructed by the builder for his family using pre-war materials and craftsmanship. Meticulously maintained, expanded and renovated over the last 25 years by the current owner. The land is a flat rectangle, professionally landscaped in a truly park like manner

Enjoy coastal living in this extraordinary east-facing 6-bedroom waterfront residence set on 1.5 acres, with spectacular views and natural light throughout. The renovated interior features white oak floors, a sophisticated new bar flowing into the living/dining area with double-height ceilings and extra-tall windows. A private office with double exposure, and an elegant library add versatility for working at home. The luxurious primary suite offers a renovated bath, balcony and walk-in closets, while 3 additional ensuite bedrooms, 2 with balconies, complete the second floor. The walk-out lower level includes a rec room, 2 en-suite bedrooms plus a terrace overlooking rolling slopes and Thrushwood Lake perfect for kayaking and paddleboarding. The garage apartment is ideal for guests

Completely reimagined and expanded to nearly twice its original footprint, this exceptional Riverside residence is the result of a meticulous gut renovation by Abode Interiors NYC, where sophisticated design meets effortless modern living. Graceful arches, soaring 9- and 10-foot cathedral ceilings, wide-plank Brazilian oak floors and a marble fireplace establish a refined architectural language, while all-new windows bathe the interiors in natural light. At the heart of the home, an Architectural Digest-worthy custom kitchen pairs Calacatta Gold marble, quartz countertops, Bosch appliances and bespoke millwork with an expansive eat-in peninsula. The adjoining dining area opens through dramatic 12-foot sliding doors to an oversized deck, creating a seamless connection between indoor and outdoor entertaining. A light-filled, lofted family room offers a striking second living space, while the privately positioned primary suite is a serene retreat with a custom-designed dressing room and s

Thoughtfully updated and truly move-in ready, 38 Amherst Road offers a fresh, design-forward take on Riverside living. The light-filled main level brings together the kitchen, dining and living spaces in an easy, open flow, with direct access to an expansive deck that extends the living space outdoors. Four bedrooms are thoughtfully arranged across the upper levels, including a private primary suite with a spacious walk-in closet and en-suite bath. A generous family room provides a separate space to relax, work or gather, while the finished lower level offers additional flexibility for a playroom, gym or home office. Recent improvements throughout the home pair a clean, considered aesthetic with everyday functionality, creating a home that feels both polished and comfortable. The home offers multiple spaces for entertaining, playing and enjoying the outdoors. Convenient to schools, train, shopping and everything Greenwich has to offer, 38 Amherst Road is ready for its next chapter. Age

Direct waterfront with dock. This is one of the most stunning water views in Greenwich. a rare combination of both south and western exposures that provides views all the way to Long Island but also fabulous afternoon light and evening sunsets. Add to that, the property is completely out of the flood-zone and has a highly functional dock. The house is a classic antique 'Captain's house', which can be renovated/expanded or build new. Lot size = 24,402 sq.ft. so FAR calculation suggests around 5,500 sq.ft plus additional 3rd floor square footage and full-basement square footage. Includes separate garage building. Wonderful neighborhood, off the beaten path, but extremely close to schools, train, and Yacht Club

Presenting a rare Riverside home, this SBP Homes masterpiece, custom-built in 2009, is now on the market for the first time. Designed to capture breathtaking water views and stunning sunsets. Situated in a peaceful private association within the desirable 1-acre zone off Indian Head Road. Manhattan skyline in the distance, regular Summer firework displays can be seen from Rye Playland as the perfect dinner or outside fireplace back drop. Egrets, herons and duck will share your view year round! The main level boasts a spacious eat-in kitchen and family room, leading to a butler's pantry, dining room, and light filled formal living room. A beautifully appointed oak-paneled office with Long Island Sound views adds a touch of sophistication. Upstairs, the primary suite offers panoramic view accompanied by three family bedrooms and a convenient laundry room. The third floor features an additional office, guest space, and a full bathroom. The finished basement includes a wine room, playroom/

Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside's prestigious Indian Head Association, this storied property occupies the historic grounds of railroad magnate Henry Francis Shoemaker's former compound-a Gilded Age legacy that later served as the backdrop for the iconic Cedar Cliff Beach Club of the 1920s. The estate bears the name Shoemaker originally gave his villa, 'Cedar Cliff'-a designation that eventually defined the very road on which it stands. Elevated high above the flood zone and offering 1,250+ feet of direct water frontage the property unfolds with extraordinary scale and privacy. A sweeping, manicured lawn rolls gracefully toward the shoreline, creating a striking foreground to the panoramic coastal vistas and an exceptio

Move right into this beautifully updated Colonial, tucked away on a peaceful cul-de-sac in the highly desirable Riverside neighborhood. Designed for today's lifestyle, this sun-filled home offers an open floor plan with spacious living and dining areas flowing seamlessly into a stunning chef's kitchen featuring quartz countertops, a large center island, stainless steel appliances, and abundant cabinetry. Upstairs offers comfortable bedrooms, including a spacious primary suite. Enjoy a private backyard perfect for entertaining, relaxing, or outdoor play. Conveniently located just minutes from Riverside train station, top-rated schools, parks, shopping, restaurants, beaches, and all that Greenwich has to offer. A wonderful opportunity to enjoy comfort, style, and an exceptional location