luxury houses with pool for sale Greenwich, United States

Vacation at home in this exceptional five bedroom residence, where refined design, resort inspired amenities and the flexibility of optional single level living create an extraordinary lifestyle. Tucked at the end of a quiet cul de sac on a spectacular 3.2 acre private parcel, property abuts conservation land with direct access to scenic walking trails offering tranquility and natural beauty. Designed for both elegant entertaining and everyday comfort, the outdoor living experience is highlighted by a new saltwater pool and spa. The breathtaking new main level primary suite serves as a private sanctuary complete with custom closets. Upstairs four additional bedrooms - including an optional second primary, accompany updated full baths. LL boasts wine lit wine closet, sauna and media room.

Set on over two acres of exquisitely manicured grounds, this exceptional six-bedroom Georgian estate offers approximately 8,500 square feet of elegant living space, including the finished lower level. Beautifully proportioned interiors feature refined formal rooms, a chef's kitchen with premium appliances and marble island, an inviting family room, library, and a luxurious primary suite with sitting room and spa-inspired bath. Designed for effortless indoor-outdoor living, the resort-style grounds showcase a spectacular pool and spa, expansive terraces, outdoor kitchen with pizza oven and grills, fire pit, greenhouse, and organic gardens. Complete with a heated three-car garage and approved seven-bedroom replacement area, this is a rare Greenwich offering.

LOCATION ,LOCATION, LOCATION! Striking, sophisticated, & contemporary w/a true WOW factor. This exceptional residence is tucked within the celebrated Golden Triangle, surrounded by some of Greenwich's most prominent estates. A rare blend of timeless modern sensibility, the home showcases stunning interiors, refined elegance, & impeccable craftmanship. Designed for today's lifestyle, the layout balances grand entertaining spaces w/ intimate, inviting rms. High ceilings, sun-filled interiors, & seamless indoor/outdoor flow create an atmosphere of effortless luxury. Every detail has curated to elevate daily living. Sited on 3 pvt acres across 2 sep. deeded lots, framed by lush landscaping, specimen trees, & vibrant seasonal gardens creating a one-of-a-kind paradise. Do not miss the apiary! Summer magic is unmatched. A delightful screeded porch ideal for lingering with the Sunday paper, a sparking pool, and al fresco dining at its best. A charming cottage offers exceptional flexibility for a guest retreat, home office, art studio, or fitness space. Capture your future memories in this dream that can come true!

DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive, manicured lawns with desirable western exposure, framed by stone walls, mature trees, and a pool. Completing the estate is a three-bedroom cottage, providing additional flexibility. Ideally serviced by public gas, water, and sewer allowing for ease of development. Perfectly positioned near schools, clubs, houses of worship, and Greenwich Avenue. Lot is 2.02 acres in RA-1. FAR = 11,878+/-

Exquisite custom Georgian manor perfectly situated on over 2 acres of park-like grounds in a gated Association. The manor boasts beautifully proportioned, light-filled rooms with high ceilings, stunning architectural details, and impeccable craftsmanship. Residence offers both sophisticated formal areas and comfortable family spaces, striking a unique balance for easy enjoyment. Magnificently scaled rooms include a mahogany library, and a spectacular Christopher Peacock kitchen with Calcutta marble double islands and an oversized breakfast room. Features include seven en-suite bedrooms, lounge & bar, wine cellar, gym and home theater. Property features stunning verandas overlooking gardens, fountains, terraces, and a pool with spa and waterfall. Square Footage is for 1st and 2nd levels. Lower Level: 2,262.58

A gated drive opens to this elegant six-bedroom Mid-Country Manor overlooking tranquil views of Horseneck Brook. A stone courtyard introduces the dramatic four-story residence with elegant foyer, where sweeping butterfly staircases and limestone floors create a striking architectural welcome. From the gracious gallery hall, beautifully proportioned formal and informal rooms unfold-including generous living and dining rooms, a family room, chef's kitchen with breakfast room and a private paneled library-all distinguished by hardwood floors, bespoke detailing, and soaring ceilings. A gracious ground floor guest suite completes this level. The serene primary suite offers a spacious retreat with fireplace, luxurious bathrooms, generous dressing rooms and complemented by an elegant sitting room with its own fireplace. Four additional en-suite bedrooms are located on the second floor. The third level offers versatile living space, including a custom home office, playroom, and full bathroom. The walk-out lower level is thoughtfully designed with a pool cabana, sauna and pool bathroom, wine cellar, gym, game room, mudroom, and direct access to the three-car garage. Outdoors, a pool, spa, and outdoor kitchen overlook the gently flowing brook and beautifully landscaped grounds. Ideally situated in the heart of Greenwich, this exceptional residence seamlessly blends privacy, architectural character, and convenience.

Overlooking Wilshire Pond, 35 Wilshire Road is a rare modern backcountry compound set on 5.29 private acres with a true resort-like feel. Designed by noted architect Gerald Schiff, the home offers approx. 7,884 sq ft, 8 total beds & baths, bold entertaining spaces, and dramatic architectural details throughout. Amenities include a natural pool with waterfall and 15+ ft deep diving well, stone pool house with guest suite, tennis court with stadium lighting, expansive sports lawn, renovated gym with floor-to-ceiling windows, 3-car garage and generator. Substantially improved by the current owners, with reimagined landscaping, enhanced living spaces & upgraded systems, this is a one-of-a-kind Greenwich retreat is designed for privacy, recreation and effortless entertaining.

Handsome brick Georgian just off Round Hill Road, renovated and expanded in 2010 with pool and spa, set on 2.41 landscaped and private acres. Custom built with exceptional attention to detail, this 5 bedroom, 6,200 +/-sq ft home embodies timeless architecture paired with a floor plan for modern living. A grand double-height reception hall creates a striking first impression, unveiling sun-drenched interiors and beautifully proportioned formal and informal spaces ideal for both entertaining and comfortable everyday living. The eat-in kitchen, accompanied by a butler's pantry, is designed to satisfy the most discerning chef. Paneled library with fireplace for work at home, or relaxation. Primary suite with fireplace and two walk in closets is complemented by four additional ensuite bedrooms. Third floor is flexible space in use as a large gym with spa bathroom. The lower level is fully finished and ready for customization. Completing this exceptional offering is a four-car garage, mudroom and laundry room. Enjoy resort-style outdoor living with pool and spa surrounded by mature plantings and exceptional landscaping providing a true sense of privacy and tranquility.

Timeless 1925 Colonial reimagined for modern living. Set on oversized, stunning 3.43 private acres in a coveted Mid-Country Greenwich location, this exceptional estate offers over 7,000 square feet of beautifully updated living space. Thoughtfully transformed, the home seamlessly blends the architectural character and craftsmanship of a bygone era with sleek contemporary design and today's most sought-after amenities. Elegant formal rooms, inviting gathering spaces, and 6 spacious bedrooms are complemented by 7 full baths, while 4 fireplaces add warmth and character throughout. The stunning grounds provide a true retreat, featuring a sparkling pool, expansive lawns, and exceptional privacy. A rare opportunity to enjoy historic charm and modern luxury!

GREAT INVESTMENT OPPORTUNITY-Bellavista is a 16,000+sf estate designed by architect Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus Long Island Sound views from the 2nd and 3rd floors, A truly sophisticated modern lifestyle.The residence is distinguished by its extensive integration of advanced technology systems, seamlessly embedded throughout the home. Smart-home infrastructure (lighting, climate, security,and entertainment).State-of-the-art environmental and wellness technologies (air, water, energy efficiency,and comfort). Attached 2 car garage + 5 car carriage house w lifts. 45'x20' pool. Features: Full house generator. Venetian plaster walls, bleached white oak and porcelain floors throughout, radiant heated floors (including garage), self cleaning glass beaded stucco exterior with composite slate roof, imported windows/doors and stone, and expansive property for sports and entertaining. Pet grooming room with separate laundry. Chef's kitchen and additional family kitchen. Plans for an additional indoor pool and underground parking garage for 8 more vehicles with car elevator. Separate staff quarters.

Welcome to one of Round Hill's most treasured historic properties. Originally established in 1795 as the community's first schoolhouse and later transformed into a picturesque mid-19th century center hall Colonial, this remarkable home is located within the Round Hill Historic District. Perched high on 4.6 fully fenced acres, the property enjoys broad western exposures and magnificent sunsets. The 5-bedroom main residence blends period character with modern comfort and is complemented by a separate garage cottage. Wide plank floors, sweeping lawns, mature landscaping, vegetable and flower gardens, a swimming pool, and enduring architectural details create a quintessential Greenwich country setting and a rare opportunity to own an authentic piece of local history.

Privately tucked away at the end of a tranquil lane in prestigious Mid-Country Greenwich, this custom-built stone manor is a rare offering of timeless architecture, exceptional craftsmanship, and resort-like amenities. Encompassing more than 11,373 square feet and set upon 3.2 exquisitely landscaped level acres, the estate is surrounded by sweeping lawns, mature specimen plantings, and beautifully curated gardens that create an atmosphere of complete serenity and privacy. Designed for both grand-scale entertaining and comfortable family living, the residence features six bedrooms, eight bathrooms, and elegant interiors defined by high ceilings, abundant natural light, and refined architectural detailing. The main level boasts impressive 11-foot ceilings, gracious formal and informal rooms, a gourmet kitchen and oversized windows framing picturesque views of the grounds, pool, pool house and cottage with kitchen. The second floor, with 10-foot ceilings, is highlighted by an extraordinary primary suite offering a private sitting room, dual spa-inspired bathrooms, and two generous walk-in dressing rooms and a home office. Four additional en-suite bedrooms and a spacious laundry room complete this level. The thoughtfully designed lower level provides exceptional recreational and lifestyle spaces, including a guest bedroom and bathroom, family room, media room, fitness center, powder room, and additional space perfectly suited for the creation of a world-class wine cellar. The estate's outdoor amenities rival those of a private resort. A charming stone pool house with soaring ceilings, a fireplace, inviting living and dining areas, a kitchenette, changing room, and a full bathroom overlooks the spectacular 30' x 60' swimming pool and spa. Completing the compound is a beautifully appointed 1,500-square-foot guest house with two bedrooms, one full and one half bathroom, living room with fireplace, dining area, kitchen, office and an attached two-car garage, providing luxurious accommodations for extended family and guests. Offering an unparalleled combination of privacy, scale, and sophistication in one of Greenwich's most coveted locations, this exceptional estate represents the very best of country estate living just moments from town, schools, and commuter access.

Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated and expanded, this warmly inviting residence offers 10,664± square feet with six bedrooms, six full and two half baths, plus eight fireplaces. Above the three-bay detached garage is a renovated two-bedroom, 903-square-foot apartment with full kitchen and laundry. Leafy views from every room overlook the enchanting landscape. There is a pool with spa, fenced vegetable garden and fenced chicken coop. With so many aspects of special distinction, this is a wonderfully unique compound that captures the feel of the English countryside in a tranquil mid-country location. Includes legally permitted medical office.

An approximately 8,000 SF Connecticut Colonial on more than seven acres in mid-country Greenwich, on one of the town's most established addresses. Seven bedrooms, eight fireplaces, a formal dining room, and a slate-tile roof -- a 1923 residence with period character on a scale of grounds increasingly rare in mid-country. A long private drive rises from the road, with the land revealing itself gradually: a nearly one-acre pond at the back of the property, a swimming pool, tennis court, two-bedroom guest cottage, and a detached three-car garage. The amenity stack -- pond, pool, tennis, cottage, garage -- is essentially irreplaceable on a single Greenwich parcel and reflects six decades of stewardship by one family. This is part of the four-parcel Spring Farms at Round Hill assemblage, brought to market for the after sixty years in one family. For buyers also considering renovation, expansion, or longer-term redevelopment, Workshop/APD -- leading architecture and interior design firm -- and Davis Chase Homes are available to design and build on the buyer's timeline. See the full Spring Farms at Round Hill brochure for context on the broader collection: https://issuu.com/workshopapd/docs/rhg_marketing_brochure

Privately set on more than 6 extraordinary acres within the prestigious Khakum Wood Association, this award-winning estate offers distinction, privacy, and architectural excellence in an A+ location. Clad in limestone, fieldstone, and stucco and crowned by a graduated slate roof, the residence is defined by timeless elegance and exceptional quality. Bright interiors feature soaring ceilings, imported natural materials, and superb craftsmanship throughout, while a modern floor plan is designed for both entertaining and daily living. Stone terraces on every level overlook sweeping level lawns. Complete with a separate apartment for guests or staff, 7 garage bays, pool, and bocce court, this is unlike anything else on the market.

Nature lovers look no more! Welcome to this very quiet private home nestled comfortably within its surrounding. Enjoy tranquility, mature trees and landscape from every room including a special screened-in patio with fireplace. Additionally, this well maintained and spacious 4 bed, 3 1/2 bath offers multiple floor plan uses for your very own enjoyment.

Serene living in this bright, turnkey 5-bedroom, 4.5-bath Colonial set on two private acres with a pool and entertaining terrace. Designed for comfort and flow, the home features abundant natural light and an open floor plan. The sun-filled family room opens to a newly renovated chef's kitchen, while a private study with fireplace offers a quiet retreat. Upstairs includes a spacious primary suite with spa-like bath, plus four additional bedrooms and two baths. The finished lower level with fireplace and full bath adds versatile living space. Mature landscaping, specimen trees, whole-house generator, and numerous upgrades complete this move-in-ready home.

Nestled on 4.09 acres in Greenwich, CT, this breathtaking 8-bedroom Georgian Colonial estate offers unparalleled elegance and privacy. Commanding spectacular big sky views from its perch 560' above sea level, the property features exquisite formal gardens, and pool. Inside, grand-scale rooms with soaring ceilings, masterful stonework, elegant millwork, and arches create a luxurious atmosphere. Highlights include a Beverly Ellsley gourmet kitchen, cherry library, solarium, and expansive living areas. The primary suite boasts two dressing rooms, spa baths, and a sitting room. A true modern-day ''Great Estate,'' just an hour from NYC.

Originally a turn of the century horse racing track named Field Point Park, the prestigious Field Point Circle Association is now one of Greenwich’s most coveted guard-gated enclaves. Distinguished by its exclusive address, this grandly proportioned French-inspired manor of 9,565 +/- square feet combines stately elegance on a level 2.2 acres with exquisite privacy and a pool with spa. Clad in limestone with a slate roof, the six bedroom, seven full and two bathroom residence is is distinguished by a flexible floor plan, offering a primary suite option on both the first and second floors. Principal entertaining spaces—an elegant living room, gracious dining room, and refined library—are enhanced by high ceilings and oversized windows that flood the home with natural light. Opening to a grand rotunda with a double-height curved staircase, the marble foyer is the intersection between the east and west wings of the house. On the east side, an elegant formal dining room adjoins the butler’s pantry and opens to the generously sized kitchen with pantry, breakfast area and powder room. There is an attached 3-car garage in this wing, with a laundry room. Formal rooms in the west wing include an airy living room with fireplace and cozy library with fireplace and concealed wet bar which opens through French doors to the private backyard terrace. The ground floor primary suite with dressing room and full bathroom also overlooks the peaceful backyard. There is another first floor en-suite bedroom across the hall. A great room that is perfect for entertaining adjoins the full pool bathroom, kitchenette, bar and dining area which serves as a “pool house” and opens to the main terrace and pool with spa. The great room was originally an indoor pool and the pool is intact below the floor and can be put back into use. Screened by greenery for ultimate privacy, the secluded backyard with verdant level lawn and pool with spa completes this idyllic retreat perfect for all lifestyles. The Field Point Circle Association consists of only 27 homes and offers 24-hour security, while its wide, tree-lined boulevards maintain its glamorous, Gilded Age legacy. In a treasured coastal location, this historic neighborhood offers a compelling mix of proximity to downtown Greenwich, as well as easy access to New York City vis Interstate 95 or the Metro North train.