luxury houses with pool for sale Fairfield County, United States

Discover a rare gem in the heart of Greenwich's prestigious ''golden triangle.'' This stunning 2.83-acre property, available for the first time since 1988, boasts a private, picturesque, level and beautifully landscaped oversized property in the RA-1 zone, complete with town water, gas, and sewer—an exceptional find. The classic 1962 home features 3,231 sq. ft. of elegant living space, offering 4 spacious bedrooms, 4 full bathrooms and 1 half bath perfect for family living and entertaining. The property also includes an impressive guest/pool house with guest bedroom, ideal for hosting friends and family, along with a lighted tennis court for active outdoor enjoyment. This property not only offers a unique lifestyle opportunity but also a chance for future development. Don't miss out on this unique opportunity to create your dream home in one of Greenwich's most sought-after locations!

Discover the epitome of luxury living in this stunning, rare custom-built Riverside waterfront home, available to the market for the first time. Spanning an impressive 9,418 square feet on 1.45 acres, this remarkable property designed by renowned architect Cormac Byrne features breathtaking interiors with an open concept design that ensures a great flow throughout. High ceilings and oversized windows enhance the sense of space and light, creating an inviting atmosphere with sweeping water views throughout. Enjoy a beautiful pool and a private dock, perfect for water enthusiasts, all while soaking in west-facing views that provide a picturesque backdrop for sunsets. The walk-out lower level adds convenience and elegance, ideal for entertaining or relaxation.

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.

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.

Discover this beautifully expanded and renovated shingle-style home, expertly reimagined by award-winning RS Granoff Architects. Featuring 5 spacious bedrooms and 4 1/2 baths, this hidden gem is nestled in a private in-town setting within the coveted Rock Ridge Association, just moments from downtown Greenwich and its vibrant offerings. Set on a stunning 1.45-acre park-like lot, the property boasts professionally landscaped mature gardens, creating a serene oasis. Enjoy the luxurious outdoor experience with a beautiful pool and spa, perfectly complementing the home's timeless style and modern living. This exceptional residence offers the ideal blend of elegance and comfort, all within close proximity to the amenities you desire.

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.

Set high above Lake Avenue on 4 secluded acres, this bright and airy contemporary residence offers an open floor plan, high ceilings and large picture windows overlooking the tranquil backyard with a pool. A 1st floor primary suite makes for easy one-floor living. First floor spaces include the skylit kitchen with breakfast area, family room with fireplace and dining room. The living room and office both have fireplaces and there is a first floor en-suite guest bedroom. Sliding doors open to the terrace with inviting freeform pool and spa looking out to a dining pergola. Upstairs are 3 more en-suite bedrooms, a 2nd office and a home theater. Walk-out lower level has an exercise room, sauna and full bath. Peaceful gated retreat with its own guard house on a private cul-de-sac off Lake Ave.

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.

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.

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.

Like a dream come true for anyone passionate about horses & luxurious living. Picture waking up to serene mornings with coffee in hand, gazing out over your horses peacefully grazing in the paddocks—a perfect start to the day. The main house, updated in 2024, offers spacious & elegant living space making it ideal for hosting family & friends. The open floor plan ensures a great flow between rooms, perfect for entertaining. Imagine gatherings in the family room, warmed by the stunning floor-to-ceiling stone fireplace, with views of the heated in-ground pool & expansive backyard. The lower level adds even more appeal, with a large game rm, a study, a wine cellar & an expansive unfinished area that offers endless possibilities. This estate blends luxury, comfort & the equestrian lifestyle. The equestrian facilities are equally impressive, with 2 barns accommodating up to 10 horses, and a 2-bedroom apartment above one barnperfect for staff, guests, or extended family members. The ample turn-outs, ring, and extensive fenceable land offer plenty of room for your horses to roam and thrive. And being so close to Silverman's Farm and other equestrian facilities, you'll enjoy the best of both worlds: a beautiful, private homestead and a vibrant equestrian community. An opportunity not to be missed!

This original 1954 modern craftsman home has undergone a complete transformation with keen attention to detail. Exuding charm and sophistication, this gated property spans 3.8 acres and features a 4,146 square foot, 4-bedroom, 3.5-bathroom residence showcasing contemporary architecture, and an indoor custom Endless Pool. Savor the natural beauty of inspiring gardens and farm fresh eggs from your own chickens. The grand foyer welcomes you with curved glass windows and a sweeping wrought iron staircase, complemented by exquisite artistic decor. The living room boasts vaulted ceilings, stunning floor-to-ceiling windows, and a cozy wood-burning fireplace. The recently updated chef's kitchen features a seamless flow to the dining room and outdoor patio. Custom European cabinetry with high-end amenities, granite countertops, a porcelain backsplash, and premium appliances (Wolf, Bosch, Sub-Zero + wine cooler) make this kitchen the ideal entertaining hub. The newly renovated primary bedroom suite is a true retreat, featuring a large walk-in closet, plus spa-like bath with radiant floor heating and thermostatic shower. This home features a rare second primary suite on the main level (also ideal for in-law or guests), complete with a walk-out patio, hot tub, spa bath, laundry, and kitchenette. Additional bedrooms provide ample space, large closets, and one with custom cabinetry, ideal for a home office. Finished basement with bar, 2 car detached garage, and top location just 60 miles to Midtown

HOMEWOOD - This remarkable country compound is one of the precious few 18th/19th century shingle style colonial revival estates remaining in Fairfield County. Dating back to 1750, the original pre-revolutionary war home captivated the attention of prominent NYC banker, George Haven, who purchased the home in 1890 and expanded it significantly including a glorious 50 foot ballroom designed by Elsie de Wolfe, 19th century designer, rivaling the best of her work in NYC. Today, after $2M of extensive and thoughtful updates over the past decade, Homewood is unparalleled in its historical detail and state-of-the-art features. Total 12,853 square feet on 3 levels with 20+ rooms, 13 original fireplaces, 8+ bedrooms, 7/2 baths; pool house with kitchen, full bth, and changing rooms; heated gunite pool and spa; 3 carriage style garages with porte-cochere; multiple porches/terraces; set on 3.22 manicured and level acres. Highest attention to detail: front to back Great Hall with ingenious ceremonial mahogany staircases; expansive chef's kitchen/butler's pantry; over-sized formal dining room with breakfast alcove; plus primary suite with private balcony, multiple closets and 2 sumptuous bathrooms offering radiant heated floor, steam shower, and jetted tub. Vast 3rd floor with additional bedrooms, artist studios, even a cook book library, plus elevator to all levels in the home. Additional: 9 zones HVAC; 3 zones radiant; generator; irrigation; Glen Gate designed stone terraces, flowering gardens/orchard; all in premier Silver Spring location, just moments to the NY border.

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!

Set back and private, this meticulously crafted, custom-built home is impeccably well maintained with beautiful hardwood floors, exquisite custom woodwork and 9 ft ceilings that add a touch of style to every room. Inside, you will find stunning craftsmanship and a beautiful design throughout the home. The main living area provides a great open floor plan with vaulted ceilings, stone fireplace, high end kitchen complete with stainless steel appliances, gas Viking stove, extra deep granite countertops, custom cabinetry, and a family room with expansive views of the beautiful backyard. A huge recreation room, laundry room, 1/2 bath, and a mudroom round out the main living spaces. Down the hall you will find a fabulous master suite featuring an oversized bedroom with a full walk-in closet and a beautiful ensuite bath. Upstairs are three large bedrooms, a beautifully appointed Jack and Jill bathroom, an additional hall bath, a versatile office/5th bedroom. Outside, discover a spectacular custom patio with a large stone fire pit, perfect for all your entertaining needs. A 20x40 ft built-in pool, two pool houses and plenty of yard space for whatever games or gardens your heart desires. This is a one of a kind private oasis just waiting for endless outdoor enjoyment! Located minutes to ample shopping, restaurants, Route 7 and I-84. A 5 minute walk to the Old Bridge Sanctuary, a 25 acre park with hiking trails and kayaking. 75 minutes to NYC.

Ideally located on a premier private lane in the Greenwich estate area, this historic stone Georgian has undergone a major renovation and restoration highlighting its elegant old world details while creating a dynamic floor plan over four levels for today's lifestyle. Sun-filled, open and airy, the residence features a spectacular front to back entry hall leading to entertaining rooms with high ceilings and antique fireplaces including a formal dining room, gracious living room and a paneled library. A new gourmet kitchen and butler's pantry adjoin the family room with fireplace and casual dining area. There are seven bedrooms over the second and third floors, including a spectacular master suite with two bathrooms, two dressing rooms and a sitting room/office. Noteworthy for its oversized 4.85 acre, parklike property, this estate includes a pool and tennis court. This is an extraordinary opportunity is just minutes to Greenwich Avenue.