Greenwich CT Real Estate & Homes for Sale

Pristine, rolling 2.68 acres on backcountry cul-de-sac off of Cliffdale Road. Set high above the road, the property features stone walls, meandering driveway through flowering trees, and beautiful sun-drenched flat yard. Start anew and build up to slightly over 7,000 square feet (according to FAR calculations) or renovate and expand the existing 2-bedroom 2-bathroom Cape Cod style house with attached 2-car garage. Present house structure, if maintained, requires considerable work and is sold as is. Probable pool site. Gorgeous barn can be kept as is or would be a great candidate for conversion to a pool house or guest house.

Lower Lake Avenue family compound, enter through a historic courtyad, foyer boasts hardwood and marble floors. All main house rooms open from the foyer: living room with built-ins and French doors to one of the many terraces. Dining room with 3 exposures is light filled and has gorgeous views of the 1-acre beautifully landscaped property. The sunroom offers a quiet oasis. The open, eat-in kitchen and family room are perfect for entertaining, access to multiple terraces. The stately colonial main house was built in 1900 and expanded in the 1970's, 5 bedrooms 4.1 baths. New addition for guest suite was built in 2018, additional 2 bedrooms/2.1 baths. 7,148 sq ft. in total. Located just minutes from downtown and the shops, restaurants and lifestyle that it offers!

Introducing a timeless Round Hill estate, on the market for the first time in over 50 years. Nestled midway along a quiet cul-de-sac, this pastoral property spans over 10 sweeping, private acres, overlooks a tranquil pond, and offers access to riding trails. The main residence features beautifully proportioned, sun-filled rooms, 5 bedrooms, 4 full and 2 half baths, and a walk-out lower level that opens to a terrace and pool. Additional highlights include a greenhouse, a 6-stall barn with lounge, tack room, staff apartment, and expansive paddocks. An exceptional offering in the heart of Round Hill experience the privacy and legacy of this remarkable estate.

Extraordinary, custom-built 5 bedroom stone + shingle Colonial is tucked away on 10 beautifully landscaped gated acres in serene backcountry. Sunlit 8685SF interior boasts generously scaled rooms with high ceilings + stunning details including four wood burning fireplaces + wide plank floors. The house is designed to take full advantage of picturesque setting bringing the outside in from all rooms. 1st floor has an open flow for entertaining including a year-round solarium + wood-paneled library. Gourmet kitchen / family room opens to expansive stone terrace. 4 suites on second floor include an impressive primary suite with library & balcony. Walk-out lower level withgame room, full bath + exercise or 5th bed. Extremely peaceful setting abutting a 50-acre private art foundation. Specimen trees + mature plantings, gated courtyard + 3 car garage. Finished 3767SF lower level not included in total house square footage.

Spectacular custom limestone manor house situated on prestigious Round Hill Club Rd. Set on a prime, level, 3 acre parcel in the heart of sought after mid-country Greenwich. Meticulously landscaped and gated property is an extremely private, park-like oasis. Pear tree lined driveway leads to a stately formal entry or though the archway to the rear court and garages. The main house features ~ 11,500 ft of finished space. Impressive marble entry foyer with views through to the rear lawn and leading to multiple formal and informal areas including a well equipped, light-filled kitchen and breakfast room which connect to the dramatic double height family room. Butlers pantry with custom wine cabinets leads to a spacious dining room perfect for large scale entertaining. Formal living room with elegant bar and custom paneled billiard room. Multiple home office/study and den options on this floor. Private first floor guest suite. Dramatic curved staircase leads to a well proportioned primary suite with generous custom closet space, serene bathroom and coffee/bar area. 3 additional guest suites on this floor along with a playroom that could be converted to an additional bedroom. Recently finished lower level offers endless entertainment including Dolby Atmos home theatre, game room, gym and a custom spa with sauna, steam room and massage tables. Pool with separate spa surrounded by expansive granite patios and served by a well-equipped outdoor kitchen and covered seating area with fireplace and TV. Stone and crystal fire pit for late nights under the stars. Elegant tennis court blending perfectly into the lawn. Guest house (~600 sf) features bedroom/2 bathrooms/kitchen and outdoor shower. Home interior was meticulously designed and curated by Gilles Clement Designs - this is the ultimate one of a kind estate in an exceptional location. Home is on a 7 bedroom septic.

Neighboring Greenwich's most significant equestrian property, this peerless estate sits less than one short mile from the Banksville shopping center where the acclaimed gourmet & coffee shop entices locals to linger and chat. A 3-story entry is flooded with natural light from the glass dome above, and open plan living flows seamlessly. Formal living & dining rooms give way to the kitchen/great room with massive central island, wide open dining area, & family room with fireplace. It's the space you'll never leave. The primary suite is a welcome escape with dual baths, walk-in closets & a private balcony overlooking the gorgeous grounds. 3 additional very private en suite bedrooms with custom closets & a laundry room are on this 2nd level. The 3rd floor is fully finished bonus space, perfect for a sleepovers and an additional home office or two (or more!). The lower level is terrific featuring very high ceilings, 2 spacious en suite bedrooms (which can easily serve a nanny or staff as there is a private exterior entrance), the massage room, a huge gym, and additional storage. A 3-car garage with a full, walk up attic above for easy storage is an added bonus. Recently built to the very highest standards, and incorporating the latest in tech, this newer construction home makes it easy to move right in. Generator & whole house water filtration system.

Welcome to this tastefully renovated and meticulously maintained condo in the highly sought-after Greenwich Hills community-where comfort, convenience, and a touch of luxury come together. Recently remodeled, this home features a chef-friendly kitchen with top-of-the-line appliances, custom cabinets, and sleek Caesarstone countertops. The main level offers a bright, open floor plan with a sun-filled living room, newly redone powder room, dining area, and dine-in kitchen-all with peaceful views of the surrounding preserve land. Step outside through the sliding glass doors to your own private yard, complete with a bluestone patio and mature shrubs-an ideal spot to relax or dine alfresco. Upstairs, you'll find three spacious bedrooms, including a bright primary suite with lots of closet space and two additional bedrooms on the backside of the home with an updated full bath. additional full bath. The finished lower level adds even more flexible space with a family room featuring custom built-ins, an extra bedroom or home office, and a full bath-perfect for guests or working from home. Enjoy the park-like grounds with amenities including a heated pool. Show-off your competitive side or let loose on the tennis/pickle ball courts with friends. Experience resort-style living in one of Greenwich's most desirable communities-just minutes from shops, schools, and transportation. 1-car garage and additional unmarked parking is available.

In Town Location. Built in 2019. 3 Bedroom/2.5 Bath Townhouse. Open Floor Plan w/High Ceilings. 2 Story Foyer. Hardwood Floors. Gourmet Kitchen with Marble Counters. Formal Dining Room. Family Room w/ Fireplace Adjacent to Kitchen. Large Sunlit Living Room. Master Suite with Walk-In Closet and Marble Master Bath. Finished Lower Level for Exercise Room/Playroom. Stone Terrace, Great for Entertaining or Relaxing. 2 Car Attached Heated Garage. Close to Shopping, Transportation, and Schools.

Remarkably, 78 Khakum Wood has been treasured by only 2 owners. Built in 1906, this was the first structure in the private community envisioned by Newton Phelps Stokes in collaboration with the esteemed landscape firm of Olmstead Brothers. Sited on 2.95 acres , this was the original gate house for the Stokes estate serving as the stables, the kennels and staff living quarters. The unique Tudor style is charming with the characteristic pitched gabled roof, decorative wood, stonework and leaded windows. Stone walls and a substantial Belgian block courtyard create a private elegant entrance. A welcoming vestibule opens to the graciously scaled rooms with French doors to the terrace and beautiful gardens designed to respect the natural topography.

Re-built in 2008 using the highest level of craftsmanship, located in the desirable Calhoun Drive Association, this residence sits gracefully elevated, offering sweeping views of expansive lawns with mature specimen trees. Step through bespoke double mahogany doors into a grand foyer featuring tall ceilings, hardwood floors and exquisite millwork throughout. Designed for both gracious everyday living and stylish entertaining, the home offers a seamless flow between generously proportioned spaces. A sun-drenched sunroom, family room, and a kitchen with adjoining breakfast area all open onto an expansive terrace perfect for indoor-outdoor living and dining. There are multiple office spaces and incredible storage throughout. Upstairs, the luxurious primary suite offers a serene retreat with sitting room, private terrace, walk in closets and two baths. There are five additional sun-filled double bedrooms each with its own Waterworks bathroom. An additional private guest suite provides added comfort and privacy. The walk-out lower level is designed for recreation and relaxation, featuring a family room, gym, wine cellar, and a spacious entertainment area including kitchenette that opens to a covered patio. 55 Calhoun also includes a charming two-story original carriage house currently used for additional garaging (five in total) adding both character and versatility to the property. This distinguished and private home is a rare opportunity to enjoy refined living with close proximity to all the town of Greenwich, Connecticut has to offer.

Charming Greenwich country compound offers an inviting, updated 1900 farmhouse with beautiful gardens on 2+ level acres. This gracious 3,264 sq. ft. home blends modern amenities with original details such as hardwood floors and high ceilings. Main level features a granite-clad kitchen open to breakfast room/lounge; dining room with French doors to the side yard; wood-beamed living room with fireplace; a library and family rooms with terrace access; plus, two powder rooms and a laundry room. Second floor has the primary suite with sliding barn door entrance, walk-in fitted closet and bath; plus, an en-suite bedroom; two additional bedrooms and another bath. A barn with two-car garage has a studio above. Potential expansion and pool site. Within one hour of NYC.

BELLE HILL FARM. Reminiscent of the great country estates of Normandy. Long drive through manicured grounds to circle surrounding a majestic Sargent's Weeping Hemlock. Absolutely breathtaking grounds with specimen trees & manicured gardens. Impressive Brick & Stucco European Manor, circa 1942. Spectacular restoration & addition using the finest materials. Rooms of perfect proportion with incredible detailing. Meticulously appointed living space. Formal rooms for entertaining. Chef's Kitchen. Incredible Primary Suite. 4 additional Bedrooms. Gym & 2 Home Offices. Pool, Spa & beautiful Pool House. 3 Stall Barn, paddocks & riding trail access. Garden & Greenhouse. Nearly 9 acres including Caretaker's Cottage on separate parcel. Backs up to protected Greenwich Land Trust. Remarkable!

Welcome to your dream retreat! Discover this stunning, brightly illuminated home built in 1986 and thoughtfully renovated in 2024. Offering an expansive 4,044 sqft of beautifully designed living space, this residence features 4 bedrooms with the potential for a 5th on the main level and 5 bathrooms all nestled on a serene 1.37-acre lot in a desirable mid-country location, just minutes from town, train & schools. Inside, soaring ceilings, skylights, and oversized windows flood the home with natural light and invite the outdoors in. The open-plan living and dining spaces showcase warm hardwood floors, a stone fireplace, and a seamless flow onto a multi-tiered decks perfect for entertaining or enjoying the peaceful wooded surroundings. Enjoy the indoor-outdoor lifestyle with several decks overlooking a private yard, tranquil pond, and lush greenery. The west-facing backyard offers breathtaking sunsets to enjoy each evening, providing a picturesque backdrop for relaxation. The walk-out lower level has been recently remodeled to include an exercise room, office, playroom, two bathrooms, a stunning stone fireplace, along with additional multifunctional spaces that offer ample room for relaxation, work, and recreation. The front yard is beautifully framed by a new stone wall, evergreen landscaping, and a bluestone patio enhancing both curb appeal and privacy. This exceptional property combines modern updates with timeless charm - a perfect retreat in a peaceful yet convenient setting. Don't miss out on the opportunity to make this unique home yours!

Discover refined living in this elegant center hall colonial, ideally set on a private cul-de-sac just minutes from downtown Greenwich. Meticulous attention to detail is evident throughout, from sophisticated coffered ceilings to exceptional craftsmanship. The open-concept gourmet kitchen is the heart of the home, with generous counter space and a seamless flow into the spacious family room. Five ensuite bedrooms offer comfort and privacy, highlighted by a luxurious primary suite with its own sitting room for a serene retreat. Versatile living areas provide endless options for a home office, study, playroom, or home theatre. Additional features include a three-car garage, finished basement, and fenced yard.

This New Construction single family in Downtown Greenwich is smart, alluring and sophisticated. The layout and architectural design blend seamlessly with uncompromising quality and details, both inside and out. Sundrenched with floor to ceiling windows, wide planked hardwood floors and an open floor plan make this home a true Gem. Complimented with state-of-the-art gourmet kitchen appliances and finishes, this is the consummate chefs dream. Exceptional primary suite hosts private balcony, two walk in closets and a luxurious bath. The large rear yard is amazing for downtown living. Glowing masterpiece, a true pinnacle of architectural harmony. This spectacular home is in a prime location a few blocks from "The Ave" know for its stunning shops, restaurants and easy proximity to the train.

Modern Luxury Meets Tranquil Living in North Greenwich. Discover the perfect blend of sophistication and comfort in this stunning 5-bedroom, 4 1/2- bath modern residence, set on 4 private acres in desirable North Greenwich-just 11 minutes to downtown. Built in 2019, this thoughtfully designed home offers a bright and open floor plan ideal for both everyday living and entertaining. The dramatic Great room features soaring cathedral ceilings, a sleek gas fireplace, and seamless access to the patio and pool area with outdoor shower-your personal outdoor retreat. The chef's kitchen is a dream with a generous island, dual ovens, and two dishwashers-perfect for hosting and holiday gatherings. The adjacent dining room with dry bar adds a stylish touch for dinner parties and casual entertaining. With two spacious primary bedroom suites, both with radiant heated bathroom floors, including one on the main level, multigenerational living or guest accommodations are easy and elegant. The fully finished walkout lower level adds 1200 SF with another bedroom, full bathroom, and recreation, or fitness space. Laundry on 2 levels completes this gorgeous home. This is the modern lifestyle you've been waiting for-privacy, design, and convenience in one of Greenwich's most sought-after locations.

Spectacular Modern Farmhouse in Greenwich This newly built Modern Farmhouse blends timeless design with energy-efficient construction and high-end finishes across three sunlit levels. Featuring 4 spacious bedrooms and 4.5 baths, it's the ultimate family retreat. The chef's kitchen impresses with Thermador appliances, floor-to-ceiling custom cabinetry, a 10' waterfall island, designer lighting, and generous dining area. A 25' x 30' great room boasts 10' ceilings, 6' windows, white oak floors, and elegant millwork. The first floor also includes a custom mudroom, large pantry, and designer powder room. The serene primary suite offers his-and-hers walk-in closets, a sitting area, and spa-like bath with double shower and custom linen cabinet. A second bedroom has an en-suite bath; two more bedrooms share a full bath and open to a rooftop deck with sleek glass surround. The lower level adds a 26' x 24' rec room, full bath, and storage. Designer touches throughout: brushed nickel hardware, Calcutta stone, white oak floors, Gessi Faucets, and Giorgio Armani tile and central vacuum. Enjoy a landscaped yard, glass-surround deck, oversized garage, and app-controlled irrigation. Close to beach, shops, train, and highways.

HIGHEST AND BEST DEADLINE MONDAY MAY 19th AT 5PM. Tucked away on a quiet Riverside cul-de-sac, this beautifully updated home offers effortless living and timeless appeal. A sunlit living room flows into a flexible space-perfect for dining, play, or work. The double-height family room with skylights opens to a modern eat-in kitchen, ideal for daily life and entertaining. Sliding glass doors reveal a serene patio and in-ground pool, creating the perfect backyard escape. Smart and sustainable, this home features solar panels that eliminate the electricity bill. Upstairs, the primary suite offers a walk-in closet, spa bath with jacuzzi tub, and glass-enclosed shower. Three spacious bedrooms and a full hall bath complete the second floor. With thoughtful upgrades throughout, this move-in-ready gem is just minutes from North Mianus School, beaches, parks, train, and shops. This is the one you've been waiting for, don't miss it!

Recent stylish updates elevate this sundrenched four-bedroom Colonial on 1.17 acres in an unbeatable, central Greenwich location on a quiet cul-de-sac five minutes from town. Each well-proportioned room in the spacious 3,796 sq. ft. interior transitions easily to the next, ideal for entertaining. Amazing chef's eat-in kitchen with lovely breakfast area leads to a large family room, great for everyday living. Spacious dining room and living room with fireplace comprise the formal rooms. Adjacent, a den enhanced by fireplace and separate designated office. An added feature is a guest bedroom and full bath, always a plus on the main level. Attached garage connects to mudroom and powder room. Upstairs allows for complete relaxation in primary suite with sitting room that could be turned into an extra large closet. Two bedrooms, play/ homework area, laundry, and full bath are all on the second level. Finished lower level with open plan ideal for playroom or gym. Landscape feasibility plans for pool.

Delightful two-bedroom townhouse located in the heart of downtown Greenwich. Recently refreshed and perfect for immediate occupancy. Features an open living room with a cozy fireplace, seamlessly connected to the dining area and kitchen. Enjoy your own private outdoor space, a one-car garage with additional driveway parking, and a storage unit. This is a fantastic opportunity to reside in town, just a short distance from Greenwich Avenue, shops, restaurants, and the Metro-North Train Station.