luxury houses with pool for sale Fairfield County, United States

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.

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.

Welcome to 1 Lawson Lane, a fantastic opportunity to own a main-level, end-unit condo in the heart of downtown Ridgefield, just steps from historic Main Street! This freshly painted 2-bedroom, 1-bath unit boasts a large living room, a separate dining area, and generously sized bedrooms with plenty of closet space. There is an in-unit laundry as well as additional machines in the building's basement along with additional storage. Step out from the living room sliders onto a private back patio, perfect for relaxing. The unit also comes with a dedicated parking space (#405) right outside the front door, with ample visitor parking available. The Casagmo complex offers wonderful amenities, including an outdoor inground pool, tennis, pickleball, basketball courts, a clubhouse, shuffleboard, and a fitness room. Monthly fees include heat, hot water, AC, grounds maintenance, trash pickup, and snow removal, ensuring convenience and comfort with the special assessment for new roofs, windows, siding, parking, and hallways adding further value. Enjoy Ridgefield's vibrant community, with easy access to shopping, dining, the library, art galleries, and concerts in Ballard Park, and Ridgefield's award-winning theaters. If you're looking for the perfect blend of privacy and prime location, and a chance to make this home your own, this condo is a must-see! Seller is requesting that all offers be submitted through Final Offer. Go to williampitt.com and enter the property address to proceed.

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.

Antique lover's dream...If you love authentic features and appreciate excellent craftsmanship, this house is the one! The home features wide board floors, plaster walls, hand-blown glass-paned windows, latched doors, nine fireplaces, and antique charm; truly a piece of history. Two stunning 18th/19th-century homes were combined to create this antique masterpiece. The original Dawson house was built in 1856, beautifully maintained and restored. The current owners wanted to be true to the historic nature of the property and dismantled and moved another period home for the addition. Built in 1750, The Ring Family Homestead from Bridgeton, Maine was painstakingly deconstructed and delivered in 1985. It was meticulously reconstructed to seamlessly join the front house, offering a spacious, natural, authentic home. High ceilings grace every room; the exposed beams, nine fireplaces, and lovely details enhance the historic feel. There are close to six acres of bucolic land (on two separate lots), three post & beam outbuildings, a garage, paths through the woods, a stream, and more to enhance the experience. The attention to detail and commitment to historical accuracy is evident in details such as the bricks in the fireplaces that came via truck from Maine, the historical Old Village paint colors, original doors, many antique sconces and so much more.

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.

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.

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.

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.

''OWL'S NEST'' Magical mini estate with privacy, lush verdant landscaping, sparkling pool & pool house, plus charming garage apartment/cottage. Country home compound with blooming flowers and offering the best lifestyle of memories. This stunning & special home welcomes enjoyment, endless entertainment, with an oasis of a screen porch for lemonade sipping! Bursting with charm of a period home with a peaceful setting. Recent updates enhance its allure. Sophistication nestled sanctuary of style & comfort. Paradise awaits this rare one-of-a-kind. This is a forever home!

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.

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.

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.