luxury houses for sale Greenwich, United States (page 2)

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.

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+/-

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.

Serene & Private Escape. With a trending modern sensibility, this light-filled residence showcases oversized windows and doors, and soaring ceilings throughout the home. Designed for one-level living, the layout features 3 bedrooms, 2.5 baths with more potential, and a generous primary overlooking tranquil woodland views. A fireplace anchors the living room, while a sun-drenched south-facing kitchen and dining room, along with a gracious reception hall, create a nice open flow for living and entertaining. Set along a private lane just minutes from schools, shops, downtown Greenwich, and NYC express trains. Extras: Central AC, town water, and a 2-car garage.

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

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.

An extraordinary newly constructed residence in the heart of Greenwich, Seven Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously designed living space. Inside, soaring ceilings and stylish lighting illuminate refined interiors, including a dramatic great room with vaulted ceiling and fireplace, formal living and dining rooms. The chef’s kitchen appointed with custom cabinetry with walnut interiors and Sub-Zero Designer Series appliances is complimented by a Butler’s Pantry with wet bar. A generous mudroom with washer and dryer in addition to informal and formal powder rooms complete this level. A floating glass staircase rises through the home, connecting to the upper levels where the primary suite dazzles with a fireplace, coffee bar, spa-like marble bathroom with radiant heated floor, steam shower, soaking tub and two water closets plus two boutique-style dressing rooms. Three additional ensuite bedrooms on this level, each with custom closets and rich hardwood floors- as well as an oversized laundry room with built in drying racks. A second-floor covered deck overlooks the rear of the property for easy enjoyment. The third floor houses a fifth ensuite bedroom, a flexible room for an office or sixth bedroom, large walk-in cedar closet, and a coffee bar with refrigerator. Lower-level amenities include high ceilings with a floor plan designed for entertaining. A gym prewired for a golf simulator with 11-foot ceilings, custom humidity-controlled wine room, home office with built-ins, full bathroom with heated floor, and a lower-level great room with full bar are complimented by ample storage spaces. Outdoor living is equally impressive with a new heated 20x40 pool with auto cover with 2 ft coping and smart controls. Two covered terraces with infrared heaters plus the second-floor covered deck overlook the manicured grounds with 100 14-16 ft Arborvitae Trees enclosed by a 300-ft stone wall and motorized gates. A permeable paver motor court accommodates 12+ vehicles behind the gates plus a 3-car heated garage. Whole-house generator and property wide sprinkler system. Every detail—from the slab marble finishes to integrated smart home systems—has been thoughtfully curated for the most discerning buyer. A rare opportunity for luxury, privacy, and proximity to downtown Greenwich.

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.

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.

Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage with sleeping loft, kitchenette, and full bath -the only remaining structure from one of Greenwich's Great Estates. Tremendous potential to build new 10,584 sq.ft. house offering unparalleled waterfront living. Close proximity to Byram Park with a public pool, beach, marina and boat launch for Greenwich residents. Easy access to downtown Greenwich as well as Manhattan.

Exquisite 1942 washed brick colonial, in the highly coveted ''Golden Triangle'' abutting Rockwood Lane. Flanked by stone pillars and a circular drive set back from the road, the sprawling 3-acre lawn adorned with specimen trees and plantings ensures privacy and serenity. Step inside and be captivated by the elegant and sophisticated ambiance that permeates every corner of this home. The large formal rooms are perfect for entertaining with French doors that open to the expansive flagstone terrace. The wood paneled library and cozy den both with fireplaces offer 2 spaces for work or reading. The magnificent family room and bonus recreation room over the garage, both with walls of windows provide amazing spaces for leisure. The heart of the home is the European inspired kitchen w/ exposed rustic beams, soaring ceiling, stainless steel appliances, white cabinets and granite counters. Adjacent is a family room & breakfast area w/ fireplace. Upstairs, the separate primary suite w/ tray ceiling overlooks the rear garden and features a luxury bath and walk-in closets. Four additional en-suite bedrooms complete the 2nd floor, one accessible by the back staircase. The finished lower level has endless potential and access to backyard. This property epitomizes the timeless charm and elegance that Greenwich is renowned for, making it a cherished residence not to be missed in one of the most prestigious locations in Greenwich.

Classic 6/7 bedroom 1925 colonial on a picturesque lane minutes to downtown Greenwich. The oversized 1.5 acre lot features verdant level lawn with all town utilities. Inside embrace the modern floor plan seamlessly tied in with classic architectural details and high ceilings. Front to back living room opens to the solarium with terrace access. A handsome library with flows to the oversized formal dining room for seamless entertaining. The kitchen with breakfast room and ample storage steps down to the family room with access to the terrace, yard, mudroom, and 2 car garage. Upstairs find a generous primary suite with dressing room and bathroom. Five additional bedrooms, four full bathrooms, playroom and laundry room on 2nd and 3rd floor. Bonus staff apartment over garage. One of a kind!

Beautifully maintained & stylishly reimagined for today's lifestyle, this exceptional 7-bedroom home offers privacy, comfort & resort-style living on 4 gated acres with pool, spa, terraces & expansive lawn. Designed for both everyday living & entertaining, the floor plan features generously sized rooms, dramatic double-height family room, sophisticated bar area & updated kitchen with 2 oversized islands. The luxurious primary suite includes dual walk-in closets & spa-like bath, while all additional bedrooms are en-suite. A first-floor guest suite, mudroom, collector's garage, finished lower level with family room & gym, plus third-floor storage add flexibility. Thoughtfully designed indoor & outdoor spaces create the perfect setting for enjoying the privacy of this extarordinary home.

A rare opportunity to own a newly built 2027 residence just mins from Greenwich's finest shops, restaurants + schools. Set on .72 acres, 3 finished levels connected by elevator offer exceptional craftsmanship throughout. Main level features formal living + dining rooms, private office, family room w fireplace and a chef's kitchen w walk-in butlers pantry. The family room opens to a covered terrace w FP, Phantom screens + heaters -- ideal for year-round entertaining. Upstairs, primary suite features a FP, private deck + spa bath w wet room, accompanied by 3 additional en-suite bedrooms with walk-in closets. Finished lower level offers a gym, sauna, cold plunge, kitchenette, pool bath, guest suite + exterior access. A private yard + pool complete this exceptional in-town offering. NSS + CMS.

Beautifully refreshed, this inviting 4-bedroom home blends classic character with modern comfort just moments from downtown Greenwich. As one of only two homes in a Planned Unit Development, this charming home features an updated kitchen that opens to a comfortable family room, along with a welcoming living room and formal dining room - ideal for both everyday living and entertaining. The second floor hosts a lovely primary bedroom suite, 2 additional bedrooms, a full bath and a spacious laundry room. The third floor bedroom with it's own full bath provides a perfect retreat for guests or flexible bonus space. With a detached garage and parking, plus a prime location minutes from Metro-North, local restaurants, and shops, this home offers the best of Greenwich living.

Set on 1.21 acres, this beautifully maintained home has exceptional indoor and outdoor living designed for entertaining. Home was completely taken down to the studs in 2017. The freshly painted interior offers top-of-the-line finishes and a flexible floor plan. The main level features a private office with Murphy bed, dining room with soaring ceilings, and a cozy living room with wet bar and fireplace. Open-plan gourmet kitchen, breakfast area, and family room flow seamlessly to an expansive terrace with multiple seating areas, an outdoor kitchen, and fire pit, creating an ideal setting for gatherings throughout the year. The gorgeous primary suite features a spa bath with sauna, walk-in closet, and floor-to-ceiling windows overlooking the property. Two additional bedrooms share a full bath, while two versatile bonus rooms can be customized to fit your needs. They would make a great nursery, playroom, second office, or gym. Other highlights include an outdoor shower, space for a climbing frame and golf net, and an attached two-car garage. This property provides privacy and convenience to everything Greenwich has to offer.

Beautifully reconstructed and expanded modern home in downtown Greenwich offering 4-5 bedrooms, 5 baths, and four levels of light-filled living. The open floor plan features a designer kitchen with quartz island, gas range, walk-in pantry, family room with fireplace, dining room, living room with fireplace, and a mudroom. The luxurious primary suite includes vaulted ceilings, dual walk-in closets, fireplace, and a balcony. Four additional bedrooms, finished lower level with full bath, and outdoor terraces with fireplace provide exceptional living and entertaining space. A separate 416 sq. ft. climate-controlled studio/office plus detached garage make this a rare in-town opportunity just moments from train, parks, dining, and shopping. Sonos ready speaker system and generator ready panel.

Sport Lovers Dream - Set at end of a quiet cul-de-sac on Stillman Lane, this custom-built 2013 residence offers 4 finished levels of thoughtfully designed living space on 1.2 level acres w putting green. High ceilings, abundant natural light and seamless flow define the main level, where formal living and dining rooms connect effortlessly to an expansive open-concept kitchen and family room with fireplace. Upstairs, find a primary suite with spa-inspired bath with heated floors, whirlpool tub + steam shower plus 4 en-suite bedrooms. The walkout LL is centered around recreation + wellness w gym, golf simulator, indoor putting area, glice for skating on, rec room + wine rooms. Professionally designed landscaping by James Doyle, expansive flat lawn + outdoor kitchen complete the property.

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors and sunlit living space. A grand foyer opens to a gracious floor plan of spacious rooms perfect for formal entertaining and casual living. Highlights include an airy sunroom, coffered ceiling family room & breakfast room, all opening to a expansive terrace with stunning lawn and garden views. Generous space for a new custom kitchen. Luxurious primary suite features two marble Waterworks bathrooms, walk in closets and a sitting room with access to a private balcony. An additional private guest suite provides enhanced comfort for guests. A welcoming garden level offers a media room, wet bar, wine cellar, gym with full bath and playroom with access to a private outdoor covered terrace. The main residence has a three car garage. There is a charming two story carriage house with storage for two more cars. This stately home, located on a quiet cul-de-sac, is close to downtown Greenwich with fine shopping and dining and transportation to NYC.

Set on 4.1 beautifully landscaped acres at the corner of Locust Road and Carpenters Brook, this exceptional Greenwich estate blends timeless elegance, privacy, and resort-style living. A sweeping circular driveway leads to the approximately 8,300-square-foot main residence, surrounded by mature trees, flowering gardens, stone walls, and expansive lawns designed by Wesley Stout Landscape Architects. Sun-filled formal and informal spaces feature coffered ceilings, antique oak floors, a dramatic double-height family room, chef's kitchen, and four fireplaces. The home offers six bedrooms, including a luxurious primary suite with spa-like bath, gym, walk-in closet, and private balcony. The finished lower level includes a wine cellar, home theater, recreation room, craft room, and cabana area. Outdoors, enjoy a heated gunite pool, vine-covered pergola, stone fireplace, multiple entertaining terraces, and a private par-three golf hole. A separate guest house with full bath and private driveway provides flexibility for guests, extended family, or a home office, all conveniently located to town, schools, dining, and transportation.

Classic four bedroom Colonial in a convenient Riverside location has been thoughtfully renovated and expanded over the years. Entertain in the spacious living room with fireplace and the sun-filled dining room leading to the open plan kitchen, breakfast area, and family room. Step out from both main rooms through French doors to the beautiful covered deck with fireplace and flagstone surround leading out to the professionally landscaped English country grounds. Primary suite with walk-in closet, large bath, gas fireplace, and expansive windows. Three additional bedrooms, three additional full baths, and laundry room complete the second level. Special features include new Marvin windows and exterior doors throughout, new chimney, noise reduction exterior walls, and updated electrical and plumbing. Exterior painting of the house and oversized two-car garage completed in 2025.