luxury houses with pool for sale Greenwich, United States

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.

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.

Ideally located on a premier private lane in the Greenwich estate area, this historic stone Georgian has undergone a major renovation and restoration highlighting its elegant old world details while creating a dynamic floor plan over four levels for today's lifestyle. Sun-filled, open and airy, the residence features a spectacular front to back entry hall leading to entertaining rooms with high ceilings and antique fireplaces including a formal dining room, gracious living room and a paneled library. A new gourmet kitchen and butler's pantry adjoin the family room with fireplace and casual dining area. There are seven bedrooms over the second and third floors, including a spectacular master suite with two bathrooms, two dressing rooms and a sitting room/office. Noteworthy for its oversized 4.85 acre, parklike property, this estate includes a pool and tennis court. This is an extraordinary opportunity is just minutes to Greenwich Avenue.

New England Charm! Oasis on a quiet private lane with verdant low maintenance perennial gardens. Glorious landscaping. Allure of a period home & offers large spacious rooms. The orientation to the beautiful backyard with lush gardens will provide opportunities for endless entertaining. Pool, terrace, level spaces for swing sets/games. Pool is hidden from view unless you are enjoying your morning coffee on the fabulous screened-in porch off the luxurious primary suite w/abundance of closets, French doors, cozy sitting room with gas fireplace. A relaxing place to watch & daydream. MAGICAL & totally private. Spectacular family room with adjoining gourmet Chef's kitchen, top-of-the-line appliances. Lots of BIG surprises await. Wonderful convenient mid-country. A pleasure to show!

SUPERB renovation! Nestled in Greenwich's coveted mid-country, a romantic haven has been transformed by NYC Designer MATTHEW KOWLES. Originally built in 1893, this treasure of fieldstone, timber and stucco epitomizes modern luxury while preserving its historic charm. The extraordinary double-height entrance hall with a wrap-around second-story balcony sets a tone of grandeur, opening to a unique octagonal living room and a banquet size dining room with fireplace. The kitchen and family room, both with fireplaces have a true wow factor with their beautifully curated details. 5/6 bedrooms, solarium off primary, office, gym, laundry room add warmth and character to the ambience. Outside, expansive terraces invite alfresco dining and entertaining overlooking beautifully landscaped gardens and pool. Sparing no detail, with updated electrical, heating and air conditioning systems. Encompassing three levels of a light-filled modern floor plan with contemporary living set to an incredible standard, all within minutes to town, schools and train.

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.

SOUNDVIEW: A coastal paradise where you wake to dazzling sunrises and live your best life every day. Enjoy resort living year-round in this idyllic respite seconds from a private beach and private deep-water dock. This classic Colonial enjoys shimmering water views of the Long Island Sound in the private, guard-gated Mead Point Association offering exclusive rights to the Windrose Way deep-water dock and the picturesque Windrose Park, plus a private beach all secured by a staffed gatehouse. Architect Rick Moisan designed this custom-built six-bedroom residence as an entertaining mecca over three levels of renovated, light-filled interiors with captivating water views overlooking two acres of verdant lawn, classic gardens, a sparkling pool with year-round spa and pool house. This unprecedented package is a once in a life time opportunity. First Floor: Stunning two-story front to back reception hall hosts the main staircase and formal powder room. Transporting water views highlight all of the main rooms many of which open through French doors to the magnificent porch and expansive terrace spanning the rear of the house. Elegant living room with fireplace lends itself to formal gatherings and family get-togethers. A handsome paneled library appointed with built-ins opens to the porch. Served by a butler's pantry, the formal dining room with adjacent wet bar is perfectly suited for hosting summer soirees. A sunny breakfast bay flows off the open-plan chef's kitchen equipped with a marble topped island and top of the line stainless steel appliances. A stone fireplace anchors the open-plan family room off the kitchen. Perfect for indoor/outdoor entertaining, a French door opens from the family room to the terrace. A mudroom with built-ins and a full bathroom leads to the porte- cochere three-car garage Second Floor: The exquisite primary suite features a bedroom and spacious sitting room both enjoying coastal views and breezes. Two marble bathrooms also enjoy water views and there is storage aplenty in the two custom dressing rooms. There are four additional bedrooms and bathrooms on this level, as well as a laundry room. Third Floor: The Sky Lounge is fashioned for family fun and entertaining. It is a media room, a lounge and a bar all in one! Last, but not least, is the bunk room outfitted for the comfort of four guests and new full bathroom. Location: Mead Point is one of the pre-eminent private associations in Greenwich, located on the Gold Coast of Connecticut. Mead Point is steps to Bruce Park and to 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.

THE COLUMNS: An Architectural masterpiece combining the best of old and new in central Greenwich. The original Greek Revival mansion dates back to 1905. Noted architect Allan Greenberg designed a glass and steel addition, interior designer Victoria Hagan added her talented touch and Stephen Stimson did the landscaping plan. This exalted team landed the project in Architectural Digest. On 3.70 parklike acres, this in town compound has it all. The main house features four stories of light filled rooms with high ceilings, walls of glass, nine bedrooms replete with its own squash court and basketball court on over 15,000 square feet. Spacious two story, two bedroom guest house. Tennis court, pool and spa. Elevator, generator, SMART house features. Option for most furnishings to be included.

England's CANTERBURY ESTATE, ''AS IS'' first time on the market. Family owned for more than 100 years by the Meads of Greenwich & the Scofields of Stamford. Many generations of pleasure, enjoyment & wonderful memories. Loved & cherished home with a lot of charm. Mostly hardwood floors. High ceilings. 3rd floor possibilities. Needs updating or build your ''dream home''. One of the largest oversized parcels with flat level land, privacy plus an original Shoreline Pool with a small pool cabana. Coveted Riverside location. Close to schools, train, tennis, & park. Customize this treasure. Calling ALL builders & investors. Owner believes the property can be subdivided.

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.

Stylish and chic six-bedroom Colonial set on a coveted Greenwich mid-country cul-de-sac. Three light filled levels overlook private, professionally landscaped lawn with new heated pool. Classic center hall floor plan with spacious rooms, bespoke millwork and high ceilings. Double height foyer seamlessly leads to a formal living room with fireplace and elegant dining room with butler's pantry. Carrera marble eat-in kitchen opens to large family room with fireplace and the expansive deck with outdoor kitchen. Secluded office with Palladian style windows and fireplace and cozy library with custom bookshelves. Second level primary suite with sitting room, dressing room, and luxury bathroom. Four additional ensuite bedrooms on this level. Walk out garden level with home theater, family room, home gym and sixth bedroom leading to the outdoor oasis. Stylish and chic six-bedroom Colonial set on a coveted Greenwich mid-country cul-de-sac. Three light filled levels overlook private, professionally landscaped lawn with new heated pool. Classic center hall floor plan with spacious rooms, bespoke millwork and high ceilings. Double height foyer seamlessly leads to a formal living room with fireplace and elegant dining room with butler's pantry. Carrera marble eat-in kitchen opens to large family room with fireplace and the expansive deck with outdoor kitchen. Secluded office with Palladian style windows and fireplace and cozy library with custom bookshelves. Second level primary suite with sitting room, dressing room, and luxury bathroom. Four additional ensuite bedrooms on this level. Walk out garden level with home theater, family room, home gym and sixth bedroom leading to the outdoor oasis.

Harmoniously combining a handsome Tudor style residence, with a fabulous floor plan, this 2003 build home is supremely livable and modern. Brilliantly executed, the 7,259+/- square feet layout offers six bedrooms and five bathrooms over four levels. A dramatic foyer leads to the kitchen and adjacent family room, anchored by a limestone fireplace. Outfitted with high end appliances, the kitchen with adjoining breakfast room is a true chef’s delight with four ovens, a six-burner stove, two sinks, a commercial-grade refrigerator and two beverage drawers. Connected to the kitchen via the butler’s pantry with wine refrigerator is the formal dining room. French doors open from the kitchen, breakfast room and family room to the rear terrace. The main level also includes an elegant, formal living room and a library with bespoke built-ins, both with stately limestone fireplaces. A mudroom adjoins the three-car double height garage. On the second floor, the spacious owner’s suite overlooks the beautifully landscaped backyard and offers a dressing room with custom wardrobes, two walk-in closets and a stylish and 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. On the third floor is a playroom, a generous cedar closet and storage. Serving as a family hideaway, the 2,640 +/- square feet of lower level with exterior access boasts a full pool bathroom and laundry room, family room/media room and gym. Outside, stunning formal landscaping showcases architectural topiary trees and boxwoods, along with a fenced vegetable garden and flower beds brimming with native plantings. The house is flanked by a stone patio with dining and seating areas, a spa and a generously-sized pool. On a tree-lined bucolic street, this property enjoys the benefits of being in the private Calhoun Drive association and minutes to downtown Greenwich.

Gorgeous architect's country home compound that exudes elegance and sophistication. Desirable Round Hill area location. Evoking classic & timeless design that was custom built for owner. Bursting with charm of a period home, but all the luxuries &features of a newer home. Rich in details. Stunning estate in a peaceful setting. High ceilings, spacious public rooms, updated and so inviting. Private location with sparkling pool PLUS enchanting 1800's guest house with 3/4 bedrooms, approximately 2,000 -/+ sq.ft. perfect for home office/in-law/au pare/guests. Lasting memories of a great lifestyle. A pleasure to show. (5 bedroom septic)

Beautiful stone and shingle style 2005/6 built home on a little over one acre, on Stanwich Road on the corner of Jeffrey Road. 5 bedrooms/6.2 baths, extra height ceilings. Chef's dream kitchen adjacent to generous sized family room with extra height tray ceiling. Stone terrace across the back of the house with multiple seating areas. Stone steps lead to the pool and lounging area with pergola. Wolf, Sub-Zero and (2)Miele appliances. Luxurious primary suite with white marble bath and generous sized walk in closet. 4 other ensuite bedrooms on the second floor.Other room on the first floor is a screened in stone porch with a fireplace. Tax card says 6,021 sq ft without the lower level. Appraiser measured the lower level, 960 sq ft, total sq ft 6,981. Audio and video cameras on the property.

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 waterfront community.

Mid-Country Greenwich at its BEST. This classic colonial is private, quiet and central to town/schools/train. The heart of this elegant home is the custom chef's kitchen - designed for home cooks who like to entertain - and open to the family room where the ceilings soar to 18 feet. South-facing french doors/windows span the entire back of the home - including the formal living room, dining room and sun room - opening up to an expansive terrace. Perfect for outdoor dining and parties overlooking the pool and the private backyard with indoor/outdoor bath. Two-car attached garage plus a fully-equipped three-car carriage house/apartment just off the family room and next to the pool. 6/7 bedrooms and 2 home offices.

Modern country home on Lake Ave. Recently renovated. Flexible first floor plan, offering dramatic views through large picture window. New Eat-in kitchen opens to 620 sq.ft. custom deck leads to new heated inground pool & spa, equipped w/automatic cover & outdoor shower. Perfect for entertaining. Generous primary suite w/stunning bath & walk-in closet. Three add'l bedrooms on second floor share new hall bath. Huge 5th bedroom w/fabulous en-suite bath has separate back stair, ideal as guest or in-law suite. Expansive finished lower level can be used as family/playroom or additional guest area w/fireplace & full bath. Sliding doors lead to stone terrace & pool. Great closets & storage space, whole house generator, & heated 2-car garage. Close to Whitby IB & Parkway Schools. Private retreat.

Desirable Windrose Way Estate-Mead Point, 24 hr guard-gated assoc. w private beach on LI Sound. Exclusively for the 12 Windrose Way Assoc homes is a 160' deep water dock w access to Long Island Sound + shared ownership of 5-acres of waterfront parkland overlooking Chimney Cove. 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 + spectacular sunrise and sunset colors. Heated pool/spa surrounded by expansive bluestone terraces, large stone fireplace, pergola, expansive grass play areas, covered bluestone seating area w ceiling fans/lights. All-weather tennis court w 2 pickle ball courts + stone patio viewing area. The completely usable property plus the mix of formal and open plan interior makes this the perfect home for living comfortably/entertaining. Renovate or build new. Prime property and location. 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 space w door to deck overlooking tennis court; additional office 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.

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.