Luxury houses with pool for sale Old Greenwich, United States

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.

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.

Private 3.5-acre ''Caritas Island'' on Long Island Sound with 300-degree cinematic waterfront views. Accessed by a gated causeway, the expansive compound includes: a c1909 stone main house with 12 bedrooms and 10 baths, stunning waterside terraces and a lap pool; a c1870 3-bedroom stone guest cottage and a 6-car detached garage with 2 staff apartments above. Protected by a stone breakwater, the extraordinary 200-foot pier with 13-foot draft can accommodate a 75 to 150-foot boat. Property deed shows total of 4+ acres and also includes a greenhouse, pond, sandy beach and natural swimming cove. Unique opportunity to renovate or build new exquisite compound. Can be subdivided into 2 lots; also zoned RA1 for nonprofit use.

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.

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.

Unparalleled Waterfront Estate in Greenwich. Immerse yourself in year-round resort living at this captivating waterfront property. Witness breathtaking sunrises from your private deep-water dock, perfect for mooring a boat exceeding 30 feet. The exquisite Victorian residence is nestled on nearly an acre of meticulously manicured gardens, complemented by a sparkling infinity pool and a charming 2-bedroom guest cottage. Prepare culinary masterpieces in the brand-new Italian kitchen, boasting mesmerizing water views.This expansive home offers 6 luxurious bedrooms, each with captivating water vistas, and 7 full and 2 half bathrooms, ensuring privacy and comfort for everyone. Unwind in the private gym or explore the well-stocked wine cellar, both conveniently located in the basement. Embrace an idyllic lifestyle on Byram Shore Road, a prestigious location with effortless access to New York City.

Set in a serene cul-de-sac within the coveted Glenville School District,this elegant bright and sunny colonial home seamlessly blends classic charm with modern amenities. Spanning 4,400 sq. ft., it offers four spacious bedrooms and four and a half bathrooms on a level .37-acre lot. The bright sunny gourmet kitchen features premium Thermador appliances and large quartz island. Enjoy 9-foot ceilings on the main AND in the large finished walkout lower level with...

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.

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.

4 Elm Hill Drive is the second home of the three lot subdivision, Homes at Crawford Park. This sophisticated 6 Bedroom modern new construction colonial home situated for privacy on the corner lot is sure to please all discerning buyers. Be greeted by the inviting front porch and then as you enter the home you will be wowed by the 10 foot ceilings, grand entry foyer, soaring floor to ceiling windows and custom designer finishes throughout. The large open family room is sure to impress. Large family bedrooms all with en-suite bathrooms, big closets, walk out lower level and open concept living areas make this home truly special. You have the ability to have an in-ground heated pool. This attractive .55 acre private landscape is located in the coveted Pine Ridge section of Rye Brook and only seconds from the beautiful Crawford Park. This home gets so much natural sunlight. Enjoy indoor/outdoor living with the impressive eat in kitchen with big sliders to the porcelain patio or Trex Deck. Special features include white oak hardwood floors, hardi plank siding/AZEK trim, Anderson windows, granite front walkway, porcelain patio,Thermador Kitchen Appliances, spray foam insulation, high efficiency mechanicals, recessed LED lighting throughout, solid core doors, quartz countertops in kitchen, custom designer bathrooms and a walk out basement. This stylish home is the second home of the 3 home subdivision which abuts to Crawford Park. Enjoy water views of the sound. This lot is very private. Expected completion is Early Winter 2025.

One of the most luxurious properties in Westchester – Stone Hill Manor. This impeccably kept 7-bedroom, 8-bathroom center hall colonial is situated on a serene 2.5-acre lot. This private estate with mature landscaping, located in both the Blind Brook (Rye Brook) and Harrison School districts, is close to town and train and only minutes from shopping and dining. Highlights Include: • 35 minutes to NYC • 10 minutes to Westchester County Airport • 15 minutes to Rye Beach • Shoreline Heated In-ground Pool and Spa • Bluestone Patio with Outdoor Kitchen and Fireplace • 22' High Entry Foyer • Mudroom with Side Door and Garage Entry • Bonus Room over Garage • 1st Floor Bedroom • All Bedrooms are En-suite • California Closets • Hardwood Floors • Three-car Garage • Finished Walkout Lower Level with 10' Ceiling • Custom Built Wine Cellar - One the Largest and Most Aesthetic in Westchester • RING and DMP Security Systems • Sonos Central Stereo System • 2012 Renovation • Low Taxes • Natural Gas Generator for Uninterrupted Power

This timeless center hall colonial situated on a majestic 2.5-acre lot, is a suburban oasis located just 35 minutes from NYC and 10 minutes from Westchester County Airport. Providing exceptional privacy and tranquility, this impeccable estate masterfully blends luxury and comfort featuring 7 bedrooms, 6 full and 2 half-bathrooms, including a convenient first-floor ensuite bedroom. Mature landscaping provides this resort-like property the quintessential backdrop to enjoy the heated in-ground Shoreline pool and spa, and bluestone patio with outdoor kitchen, retractable awning and wood burning fireplace, perfect for outdoor entertaining. The home offers generous living space with well-proportioned rooms and exquisite architectural details, including extensive millwork and custom built-ins, and California Closets throughout. Enter to find a 22' high entry foyer with raised panel wainscoting flanked by the formal living room with gas fireplace and the formal dining room that the butler's pantry seamlessly connects to the open-concept chef's kitchen/family room equipped with upscale appliances. The second-floor luxe primary suite is a sanctuary, complete with 2 gas fireplaces, walk-in closets, pool-view balcony, spa shower and tub, sitting room/gym. Four additional ensuite bedrooms await on the second floor as does a 900 square foot bonus room above the three-car garage. Retreat to the exquisite finished lower level with 10' ceilings for movie nights, billiards, card games or a wine tasting starring your exceptional custom built wine cellar, one the largest and most aesthetic cellars in Westchester. Modern technology lets you conveniently control major systems from your phone including the RING and DMP security systems, Sonos central stereo system, heating and cooling systems and even your Thermador double-oven, with the ability to add your irrigation and pool controls. An added benefit is a natural gas generator for uninterrupted power. If that wasn't enough, this home also includes the option to enroll with either Blind Brook or Harrison school district, a truly golden opportunity. Enjoy the ultimate in shopping & dining experience which is only minutes away in Rye and Greenwich. For golf enthusiasts, Purchase is home to many premier golf clubs. Make your dream a reality!

Welcome to 20 The Crossing, located in the most desirable gated community in Westchester County. The Crossing offers a 24 hour manned gatehouse for security and a full-time on-site Property Manager. In addition, Homeowners' dues cover gardening, snow removal, gutter cleaning and maintenance of the common areas. The ideal location is convenient to Rye, Harrison, White Plains and Greenwich with easy access to train stations, major highways, Westchester County Airport and the many local private country clubs. Additional Information: Amenities:Dressing Area,Marble Bath,Stall Shower,ParkingFeatures:3 Car Attached,

FINALLY, ENTIRE ESTATE OFFERING OF NOW OVER 4.2 ACRES IS AVAILABLE FOR SALE, AND AT AN INCREDIBLE PRICE. One of the most special properties in lower Westchester, perfect as a convenient get away compound, horse property or just a spectacular year round estate. Set back with a private gated approach, this incredible country estate, under 45 minutes to NYC, combines privacy & convenience, grandeur & natural beauty + every possible amenity. Lovingly restored with the finest finishes, modern amenities, old world charm and over 9000 sq. ft. of luxuriously appointed living space. Ample living/working/entertaining space plus overnight guest quarters including a separate 2 bedroom guest house included on the property plus an enormous horse barn/ancilary building and partial sports court. Rolling lawns, magnificent plantings, greenhouse, fountains, reflecting pond, summer kitchen, inviting front porch & so many special extras too numerous to list. A treasure property to be had for generations. Additional Information: Amenities:Guest Quarters,Storage,ParkingFeatures:3 Car Attached,

'Robin Hill Farm' and 'Smokey Hill Farm' are situated at one of the highest points in Greenwich in bucolic backcountry. This magnificent estate encompasses the main house, represented in this listing data sheet, two cottages, stables and gorgeous paddocks, Indoor and outdoor pools, tennis house, tennis court, and two ethereal fountains. Originally designed in 1937 by Augusta L.Noel (designer of the Whitney Museum) and completely restored with additions constructed over the years to create a majestic family compound. The grounds which take your breath away, were designed by landscape architect, Jacqueline Osty, known for beautifying many of the great parks and boulevards in Paris.

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.

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.

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.

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.