luxury houses with pool for sale Greenwich, United States

Discover a rare gem in the heart of Greenwich's prestigious ''golden triangle.'' This stunning 2.83-acre property, available for the first time since 1988, boasts a private, picturesque, level and beautifully landscaped oversized property in the RA-1 zone, complete with town water, gas, and sewer—an exceptional find. The classic 1962 home features 3,231 sq. ft. of elegant living space, offering 4 spacious bedrooms, 4 full bathrooms and 1 half bath perfect for family living and entertaining. The property also includes an impressive guest/pool house with guest bedroom, ideal for hosting friends and family, along with a lighted tennis court for active outdoor enjoyment. This property not only offers a unique lifestyle opportunity but also a chance for future development. Don't miss out on this unique opportunity to create your dream home in one of Greenwich's most sought-after locations!

Discover the epitome of luxury living in this stunning, rare custom-built Riverside waterfront home, available to the market for the first time. Spanning an impressive 9,418 square feet on 1.45 acres, this remarkable property designed by renowned architect Cormac Byrne features breathtaking interiors with an open concept design that ensures a great flow throughout. High ceilings and oversized windows enhance the sense of space and light, creating an inviting atmosphere with sweeping water views throughout. Enjoy a beautiful pool and a private dock, perfect for water enthusiasts, all while soaking in west-facing views that provide a picturesque backdrop for sunsets. The walk-out lower level adds convenience and elegance, ideal for entertaining or relaxation.

AUCTION: BID 20-26 NOVEMBER. Listed for $20M. Showings By Appointment and with Proof of Funds. A scenic drive through iron gates leads to a stately shingle-style home. Set high with stunning Western views, this exquisitely renovated 5-bedroom/5.2 bath home with 7 fireplaces must be seen to be appreciated. The magnificent French country kitchen with intricately designed wood-inlay floors is just the appetizer to this masterfully designed home with orchards, a vineyard, raised vegetable garden and expansive fields. There is a 1-bedroom guest cottage that does triple duty as a garage and pool house for the infinity edge pool with spa. Don't miss this one-of-a-kind masterpiece. House sold furnished except for some exclusions. Can be purchased with 38-48 Quaker as an equestrian's paradise.

Cinematic equestrian estate and family compound on 16+ acres with three residential structures providing a total of 11 bedrooms and 13 bathrooms in backcountry Greenwich, Connecticut. Enter through custom 20 foot tall wrought iron gates that meander down the drive to the handsome shingle-style main residence perfectly nestled on the private park-like property. Completely renovated in 2023, the main residence features an adjoining one bedroom guest house/pool cabana alongside the infinity edge pool, an aviary, multiple paddocks, vineyards, vegetable gardens and fruit orchards. Designed by award-winning architect Rich Granoff and built by Drake Builders LLC for lavish entertaining, the heart of the main residence is a magnificent French eat-in kitchen with a wall of custom designed copper La Cornue stoves, cathedral ceilings, a spectacular wood inlay floor artistically crafted by John Yarema, a gas-fired fireplace and large folding glass wall that bring the outside in. Formal dining room, elegant living room, large entertainment room with an extraordinary bar with game room and a spectacular great room, all with unique fireplaces make this home perfect for hosting any event. Almost every room in the house, including the spacious library with fireplace open through French doors to a wraparound deck with breathtaking Western and Southern vistas. The front hall leading to the second floor overlooks a dramatic wax-based fiber-finished photograph of upcoming dressage horse Derek, a stunning bay, photographed and installed by National Geographic photographer Ali Darvish. Behind the wall is the unparalleled primary bedroom suite with cathedral ceilings, its polished White Zebrino marble fireplace, Super Crystal Verde marble shower wall and a backlit white quartz vanity wall. Three ample en suite bedrooms complete the second floor. The third floor is comprised of a very generous suite with sitting room, bedroom and bath with a backlit pink onyx shower wall. There is a large, walk-out unfinished lower level with stone fireplace that can be finished to taste. The French Country guest house is ideal as guest, staff or grooms quarters and offers five bedrooms and five bathrooms. It includes a dramatic eat-in country kitchen and large family room, which opens out to an expansive stone veranda with an outdoor fireplace overlooking the orchards. The lower level has been outfitted with a tack room and an après riding lounge with fireplace and kitchenette. The picturesque French Country style stables accommodate twelve horses and includes a manure management system. The property features a laser-leveled dressage arena with FootingFirst’s signature dust-free blend, TravelRight footing installed and maintained by Lawton Adams. There is also a viewing area overlooking the ring in addition to multiple paddocks with run-in sheds. The property benefits from access to the Greenwich Riding Trails located nearby. The vineyards produce merlot and cabernet wine grapes. The orchard features apple, pear, peach and cherry trees. The gardens are dedicated to growing many different vegetables. The present owner has a peacock enclosure with waterfall, but it can be used for any type of fowl or small animal. This extraordinary masterpiece available for the first time and presents unprecedented opportunity to acquire a hard to find compound with both a first-class equestrian facility and multiple dwellings.

Classic brick Georgian updated for today's lifestyle. Just renovated, the residence features high ceilings, oversized windows, hardwood flooring, tasteful stone and tile throughout three levels, a splendid backdrop for both formal and casual entertaining. One of a kind first-floor primary suite with two stunning bathrooms and two dressing rooms. Elegant formal rooms open to a west-facing brick terrace with outdoor dining area. Second floor features 4 generous ensuite bedrooms. Lower level with gym, play space, staff bedroom and bathroom, climate-controlled wine cellar and model train room. This distinguished estate overlooks 4 park-like, level acres with a stunning pool and parterre gardens in the exclusive and gated Andrews Farm private association for maximum privacy and security.

Chic, sophisticated and contemporary luxury best describes this spectacular backcountry retreat. Fully renovated 2023 classic shingle style residence w/pool, pool house, and tennis court has it all. Iron gates, long driveway and large courtyard offer the perfect approach to 5 bed/6.3 bath masterpiece wi/high ceilings, beautiful floors, exquisite wall coverings, dramatic staircase, amazing kitchen, perfect bathrooms, private office, and full gym. Soaring stone fireplace in Great room, stunning glass wine wall in adjacent game room & solarium w/ flr to ceiling windows set the tone for both elegant entertaining and family gatherings. 2nd Level: primary suite w/sitting room & luxury bath w/infrared sauna, 4 en-suite bedrooms w/custom walk-in closets and separate bonus wing. 3rdLevel: gym Amenities include pool, pool house, tennis court /pickleball lines), Koi pond, 5 car garage and private walking trail. This estate is the epitome of modern luxury, offering an unmatched lifestyle amid Greenwich's country estates.

Discover this beautifully expanded and renovated shingle-style home, expertly reimagined by award-winning RS Granoff Architects. Featuring 5 spacious bedrooms and 4 1/2 baths, this hidden gem is nestled in a private in-town setting within the coveted Rock Ridge Association, just moments from downtown Greenwich and its vibrant offerings. Set on a stunning 1.45-acre park-like lot, the property boasts professionally landscaped mature gardens, creating a serene oasis. Enjoy the luxurious outdoor experience with a beautiful pool and spa, perfectly complementing the home's timeless style and modern living. This exceptional residence offers the ideal blend of elegance and comfort, all within close proximity to the amenities you desire.

Set high above Lake Avenue on 4 secluded acres, this bright and airy contemporary residence offers an open floor plan, high ceilings and large picture windows overlooking the tranquil backyard with a pool. A 1st floor primary suite makes for easy one-floor living. First floor spaces include the skylit kitchen with breakfast area, family room with fireplace and dining room. The living room and office both have fireplaces and there is a first floor en-suite guest bedroom. Sliding doors open to the terrace with inviting freeform pool and spa looking out to a dining pergola. Upstairs are 3 more en-suite bedrooms, a 2nd office and a home theater. Walk-out lower level has an exercise room, sauna and full bath. Peaceful gated retreat with its own guard house on a private cul-de-sac off Lake Ave.

Sited on 5.3 private acres above Wilshire Pond, this move-in ready 7-bedroom modern country estate blends serene backcountry living with contemporary luxuries. Spend summers playing on the stadium-lit tennis court or relaxing with family and friends by the heated grotto-like pool with waterfall. Cozy up in the winter months enjoying water views from nearly every room in the main house or roasting s'mores in the guest house fireplace nook. This one-of-a-kind property is comprised of a beautiful and bright main house, an impossible-to-replicate stone guest house, and park-like grounds dotted with stone walkways. The main house features a large living room with fireplace, formal dining room, and a new gourmet kitchen with Wolf and SubZero appliances. The primary bedroom suite boasts a welcoming sitting room with fireplace, private balcony, and three walk-in closets. There are four additional en-suite bedrooms, a kids playroom, gym, study/office, and au-pair quarters. The awe-inspiring guest house is a masterpiece in stonework with a family room, living room, bedroom suite, media room, and kitchen with walk-up pool patio bar. This remarkable estate located on a prestigious backcountry Greenwich cul-de-sac is a hidden gem.

Impressive & spectacular estate in ROUND HILL area. Grandeur plus timeless elegance. Gates open to a lifestyle of memories, enjoyment, & pleasure. Premier location with rich history. Dignity & charm. Architectural award in 2000. Alex Esposito, Southport. Custom built. Majestic with high ceilings & spacious public rooms. Tischler windows/doors, beautiful custom millwork. 2 bedrooms en suite on 1st fl. Quality construction. Sparkling pool with spa/cabana & Har-Tru tennis ct. that can be converted to Pickleball. Fabulous LL 4,607+/- not inc. Can buy extra land. SECOND FL has 3 bedrooms.

An idyllic coastal resort, this distinguished stone Georgian enjoys shimmering waterfront views of Long Island Sound and the NYC skyline in the private, guard-gated Mead Point Association. On a peaceful cove with its own private beach, waterfront pool and dock, this magnificent home was tastefully designed in 2014 with inspiration from the original 1928 stone house by architect Cormac Byrne and builder Matt Matthews of Significant Homes. This eminently livable residence offers 12,492± square feet of living space with six bedrooms, six full and two half bathrooms. First Floor: Inside the classic entry, the front-to-back foyer hosts the main staircase and formal powder room with onyx tile flooring. Transporting water views highlight all of the main rooms which open through French doors to the magnificent waterside terraces spanning the width of the house. A beautiful reading room appointed with built-ins opens to the water, as does the generously-sized, paneled library with fireplace, bar and built-in bookshelves. The real centerpiece of the house is the double-height living room with dramatic barrel ceiling and mezzanine balcony. Centered on a stately fireplace and backdropped by water views, this show-stopping room lends itself to large formal gatherings and family get-togethers. Served by a butler’s pantry, the formal dining room with adjacent wet bar and fine dentil molding opens to a covered outdoor dining area, perfectly suited for hosting summer beachfront soirees. A sunny breakfast bay lined with French doors to the terrace flows off the open-plan Christopher Peacock chef’s kitchen equipped with a monumental marble island, Sub-Zero refrigerator and freezer, double refrigerator drawers, two Miele dishwashers, and a luxurious La Cornue range. A fireplace anchors the open-plan family room off the kitchen, with a convenient office with built-in desk adjacent. Perfect for indoor/outdoor entertaining, French doors open from the family room to the terrace with outdoor kitchen, featuring a pizza oven, built-in grill and dining area. Second Floor: In its own wing, the exquisite primary suite with two spacious dressing rooms is clad in Venetian plaster with hand-painted detailing. French doors in the vaulted, tray-ceilinged bedroom open to coastal breezes from the private balcony overlooking the water. The lavish marble bathroom with built-in sauna and steam shower enjoys water views from the soaking tub. There are four additional en-suite bedrooms on this floor as well as a laundry room with double washers and dryers. Third Floor: There is a sixth en-suite bedroom and a playroom. Lower Level: A mudroom with built-ins leads to the attached three-car garage. There is built-in wine storage, a mirrored exercise room and a utility room. Property: This 1.6-acre property is oriented to outdoor living with a pool, beach, dock and backyard fire pit. In addition to its own private beach, the property comes with deeded access to the Mead Point Association’s community beach. There is a full house generator. Location: Mead Point is one of the preeminent private associations in Greenwich, located on a waterfront peninsula with 24hr guard-gated security for its residents. Mead Point is close to Bruce Park and to downtown Greenwich Avenue, noted for its excellent shopping and dining. Greenwich has easy access into Manhattan via Metro North, while the nearby Westchester Airport offers convenient private and commercial aviation.

On a tree-lined bucolic street in the private Calhoun Drive Association just minutes to downtown Greenwich, is this brilliantly executed six bedroom home featuring light filled living space on four spacious levels. Tasteful décor and custom improvements enhanced the fabulous floor plan and high quality construction of this residence built in 2003. A dramatic foyer is a prelude to the high ceilings, custom millwork, handsome wood flooring and three limestone fireplaces featured throughout the home. The main level includes an elegant living room, formal dining room and a library with bespoke built-ins. Outfitted with high end appliances, the custom Smallbone kitchen with separate breakfast room is a true chef's delight with four ovens, a six-burner stove, two sinks, a commercial-grade refrigerator, two beverage drawers and a butler's pantry with wine refrigeration. The family room, anchored by a limestone fireplace, features French doors to the expansive flagstone terrace. A ground floor bedroom and full bathroom, mudroom and access to the three-car double height garage complete this level. On the second floor, the spacious owner's suite overlooks the beautifully landscaped backyard and offers a sophisticated dressing room with custom wardrobes, two walk-in closets and a luxurious bathroom with soaking tub and shower. There are four more bedrooms on this level, as well as a family room, private office and laundry room. The third floor includes a playroom, a generous cedar closet and storage. Serving as a family hideaway, the lower level with exterior access boasts a family room/media room, gym, full pool bathroom and laundry room. Outside, stunning formal landscaping showcases architectural topiary trees and boxwoods, along with a fenced vegetable garden, a berry patch, flower beds brimming with native plantings and verdant lawn. The house is flanked by a stone patio with dining and seating areas, a spa and a generously-sized pool with an automatic cover. Opportunity to live in a premier established estate area of Greenwich in a house that is turnkey and ready for immediate occupancy.

CREAMER HILL FARM: Perched on a hillside overlooking 81+ undulating acres of seemingly remote woodlands, this substantial landed estate includes an extraordinary 14,200+ square foot main house with panoramic pond and treetop views, a three-bedroom guest cottage, a baseball field, tennis court, indoor and outdoor pools, a hot tub and a workshop/barn. Secluded at the end of two gated driveways with an exceptional sense of privacy, the estate also belongs to two private, gated associations: Partridge Hollow Association and Sterling Farm Association. Comprised of ten parcels, Creamer Hill Farm is one of the largest private land holdings in Greenwich. There are nine already subdivided, buildable lots for potential development. MAIN HOUSE: Tastefully expanded and remodeled by architects Blas and Elizabeth Bruno, the timber-clad home marries Arts and Crafts/Shingle-style exteriors with Japanese-influenced interiors. Port Orford cedar walls and oversized picture windows framing arboreal vistas bring warmth and light to grandly-scaled living spaces which include six bedrooms and eight full bathrooms. First Floor: One of the most theatrical entryways in Greenwich, the front door opens to a Japanese garden in a double-height foyer clad in cedar shingles with a vaulted glass ceiling. Framed by living palms, stone pavers create a path through a rock garden with a pond. Shoji screen-style frosted glass doors slide open to reveal the front hall with powder room and the open-plan main rooms. Anchored by a double-height stone fireplace, the dramatic living room opens to the dining room; both with double-height vaulted ceilings and floor to ceiling window walls overlooking the peaceful side yard with a terrace, pond and pool. The dining room adjoins the inviting breakfast room and cedar kitchen with high-end appliances, a marble island and beamed ceiling. French doors open to a deck for indoor/outdoor dining. Centered on a double-height stone fireplace, the sizeable family room offers multiple seating areas, a grand piano and large-scale sculptures under a soaring ceiling. A window wall looks out over a Zen garden backdropped by acres of trees. Equally impressive views are on display in the primary suite’s light-filled bathroom with picture windows overlooking the bucolic grounds. The vaulted-ceilinged bedroom with stone fireplace and dual wardrobe rooms opens to a luxurious bathroom with a sauna, steam shower, windowed shower and two soaking tubs – a nod to Japanese bathing culture. The sauna has a door to the exterior, allowing for a quick dip in the outside hot tub or pool. There are two more en-suite bedrooms on this floor as well as a two-car attached garage. Second Floor: This floor has an office, two ensuite bedrooms and an open sitting room. A skylit gallery walkway looking into the family room below leads to a one-bedroom apartment in its own wing. Lower Level: Recreation spaces abound on this finished, walk-out level with a stunning, 37-foot indoor lap pool, glassed-in gym, game room, and billiards room. Overlooking the Zen garden, the billiards room has a stone fireplace, a full bar and climate-controlled wine cellar. An office leads to a second family room with double-height stone fireplace and walls of windows looking out to verdant landscape views. There is also a pool bath, laundry room, a one-bedroom staff apartment and a second, attached two-car garage. The garage has its own thousand-gallon gas pump right outside. Guest Cottage: Bright and modern, the separate three-bedroom cottage has an open kitchen/family room, a first-floor en-suite bedroom, a powder room, laundry, and an office. The second floor has two bedrooms with a hall bath. In a sylvan paradise with ponds, streams, and woodlands, this is a rare opportunity to live in a staggeringly beautiful setting.

Harkaway: A captivating retreat in the heart of Greenwich with a storied pedigree, this distinguished Georgian Colonial was home to the late Mary Tyler Moore. Following a meandering stream to Oakley Pond, the long, gated drive leads to the quietly secluded stone house on 7.37 acres of private, sweeping grounds landscaped by Janice Parker and buffered by 5 acres of conservation. Exquisitely expanded and renovated, the 13,825 sq ft floor plan designed by architect Stephen Wang features 2,000+ sq ft primary suite with dual baths, dressing rooms and generous closets. Separate 1-bdrm apartment with kitchen and bath above 3-bay garage. Exceptional amenities include 23' x 23' glass conservatory, gym with spa facilities: jacuzzi, steam shower & sauna, elevator, 65-ft pool with outdoor fireplace.

''OWL'S NEST'' Magical mini estate with privacy, lush verdant landscaping, sparkling pool & pool house, plus charming garage apartment/cottage. Country home compound with blooming flowers and offering the best lifestyle of memories. This stunning & special home welcomes enjoyment, endless entertainment, with an oasis of a screen porch for lemonade sipping! Bursting with charm of a period home with a peaceful setting. Recent updates enhance its allure. Sophistication nestled sanctuary of style & comfort. Paradise awaits this rare one-of-a-kind. This is a forever home!

Down the meandering driveway off prestigious Round Hill Road awaits your own private oasis in the heart of horse-country. This incredible 4+ acre estate boasts a 6-bedroom brick and clapboard Georgian Colonial featuring classic architectural details w/pool and modern amenities. A 4-horse stable w/separate office/gym round off this compound. Perfect for relaxing or entertaining friends and family, the land is spectacular. Adjacent to conservation, this unparalleled property offers unsurpassed privacy and tranquil views. Imagine yourself watching nature in its full wonder over the expansive fields while your horses graze peacefully as you sit by the pool and sip a cool iced tea. Additional land available. It doesn't get better than this.

Discover your dream country escape with this enchanting 14 acre property comprised of 3 separate lots on prestigious Round Hill Road offering unparalleled tranquility & charm. The main house, a Georgian classic Greenwich estate containing 6 bedrooms & 6.5 baths exudes timeless appeal, spacious interiors, modern kitchen & breathtaking views. A 3 bedroom cottage, separate office/gym & stables round off this compound. The meandering driveway through lush landscapes & quaint pond enhance the sense of unsurpassed privacy & splendorous views of nature adjacent to conservation land. This unique estate is a rare find, combining the best of country living with convenient access to nearby amenities. This property boasts a 4-horse stable & lush acreage for paddocks.

The Desirable Khakum Wood Association offers a magnificent lakefront property comprising two lots, representing one of the most significant estates in the Round Hill area. This legendary Grande Dame Landmark, situated at a high elevation, features a floating staircase and a panoramic vista of the lake. The noble-sized public rooms and the spectacular pool house add to the property's grandeur. Featured in The Modern Estate, this Georgian Revival home was designed in 1940 by the famous master architect Mott Schmidt, known for his stately homes for the Rockefellers, Astors, Vanderbilts, Gracie Mansion, and other prominent owners. In recent years, the property has been completely renovated by Allan Greenberg and Barry Bronfman, adding a modern touch to its rich historical essence. The lower level of the home includes a finished walk-out area, offering an additional 2,000 square feet not included in the official square footage. The second floor hosts a wellness room, office, and exercise area. The property provides seasonal activities such as canoeing in the summer and ice skating in the winter. Recent renovations also include updates to the primary suite and kitchen.

In the heart of the Belle Haven Association this stunning Federal Colonial Revival is situated on a secluded lane with western water views over Byram Harbor. The estate underwent a multi-million dollar rebuild in 2020. The resort-like property with a pool and tennis court includes a spectacular wrap around porch overlooking expansive lawns and landscaping designed by Janice Parker Assoc. Large scale family entertaining rooms with exceptional light and scale (10' ceilings). A short distance to the Belle Haven Club with access to a deep water pier and moorings. Available for the first time in 50 years, this is a rare opportunity to secure the perfect family retreat in this premier in-town private gated waterfront community.

Windrose Way-Mead Point, 24 hr guard-gated association w private beach on LI Sound. 9,000+sf brick home w slate roof on 2 level acres, 30+ feet above sea level with year-round water views of Long Island Sound, heated pool w spa and all-weather tennis court w 2 pickle ball courts. Expansive bluestone terraces, large outdoor stone fireplace, pergola, expansive grass play areas, covered outdoor seating area. 160' deep water boat dock + shared ownership of 5-acres of waterfront parkland overlooking Chimney Cove for Windrose Way residents. Clearly an investment beyond the property lines. (1st Floor-Double height entrance hall; spectacular two story custom oak wood paneled great room w impressive structural wood trusses and built in bar, double mantle fireplace; beautiful wood paneled living room w coffered ceiling and fireplace; formal dining room; large gourmet kitchen with adjacent family rooms, wood beamed ceiling and fireplace; exercise room w french doors out to 2nd pergola covered bluestone terrace; 2 powder rooms; sauna + changing room w large double head shower, access to mud room area and attached two car garage; wood and stone floors throughout. 2nd Floor-Primary bedroom w turret space surrounded w windows and extra height ceiling, primary luxury bath w steam and rain shower, spa tub, 2 toilets, 2 sinks and walk in closet space; 4 additional bedrooms; 3 full baths; laundry room; balcony overlooking great room; very large office/2nd floor family room w door to deck overlooking tennis court; plus additional office space adjacent to primary bedroom. Finished lower level with storage rooms. Security system, sprinkler system, central AC, generator. The quiet and serene location gives residents the feeling of being away from it all, but also have easy access to Greenwich Ave, I95, MetroNorth Train, 10 mins to Stamford, and 20 mins to Westchester Airport. Enjoy boating, kayaking, paddle boarding, fishing or just relaxing. The residents who live here say, 'Welcome to paradise.