luxury houses with pool for sale Fairfield County, United States

Nestled down a long driveway on 2.53 lush acres in mid-country is this elegant sunlit 5-bedrom custom brick Georgian with a slate roof. The double-height entry, adorned with a limestone floor, leads to a charming living room with a coffered ceiling and fireplace, a formal dining room and a handsome paneled office. The stunning 2021 Christopher Peacock kitchen boasts marble countertops and high end appliances. Fabulous family room with vaulted ceiling and stone fireplace. Elegant primary suite with luxurious marble bathroom. Four additional bedrooms and two bathrooms. Walkout lower level offer play and exercise rooms. Spacious mudroom, 2 powder rooms, 2 laundry's and a 2 car garage. Outdoors, enjoy a beautiful pool, an expansive terrace with outdoor kitchen, and a brick walled garden. Property abuts the picturesque Fisher Field, a Greenwich Land Trust property that is permanently protected from development.

Nearly 12 glorious acres of privacy on ROUND HILL. (home with 4.20 acres + land 549 RHR 7.42 acres) This impressive spectacular estate welcomes you. Grandeur plus timeless elegance. Gates open to a lifestyle of memories, enjoyment, & pleasure. Premier location, rich w/history. Dignity & charm. Architectural Award in 2000. Alex Esposito, Southport. Custom blt. Majestic w/high ceilings & spacious public rms. Tischler windows/doors, beautiful custom millwork + more. Quality construction. 2 en suites, 1st fl. Sparkling pool with spa/cabana & Har-Tru tennis ct. that can be Pickleball. Fabulous 2 bedrooms Guest wing on 1st fl. Garaging for 6 cars with hse, 6 car garage with land. Perfect for the car aficionado. Bespoke French countryside setting is magical. Finished LL 4,607 +/- sq.ft. not inc

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 on ROUND HILL. 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

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.

Indulge in the epitome of luxurious living with this show stopping South facing 10,749 ft colonial style home located in the heart of mid country Greenwich. With soaring ceilings and exquisite design details throughout, this 6 bedroom, 7 full and 1 half bath home is nestled on 2.1 meticulously landscaped level acres with sweeping velvety lawns and an oversized pool. Experience the perfect balance of sophistication and comfort with a lavish primary bedroom suite, 5 oversized family bedroom suites and a sensational open concept lower level game room/exercise room. Every inch of this home exudes elegance and grandeur, offering impeccable room scale and flow for effortless entertaining and everyday living. Don't miss your chance to own this extraordinary piece of paradise!

PERFECTION: A down to the studs gut renovation by noted builder DiBico Inc. in 2020 created a modern floor plan with high end finishes for easy living over three finished levels. Project included all new windows, new HVAC, new flooring, new plumbing, new electrical, new siding, new roof, new custom gourmet kitchen, five stunning new bathrooms and more. The current owner then took the home to a whole new level of style and sophistication! Residence now features a fabulous gourmet kitchen with top of the line appliances, a sun-filled breakfast room plus family room opening to an expansive flagstone terrace spanning rear of the house. Dramatic living room with vaulted ceiling and fireplace. Spacious dining room with custom wine storage and spectacular Butler's Pantry. Luxurious primary suite with separate sitting room, large dressing and stylish bathroom. Four additional bedrooms and two full bathrooms. Lower level custom home theater, gym and game room. Enjoy a park-like oasis featuring over two acres of verdant lawn with heated pool in the heart of the mid-country estate area of Greenwich, Connecticut.

Magnificent backcountry estate on 4.65 beautifully landscaped acres with a timeless Georgian-style residence showcasing custom millwork, exquisite architectural detailing and high ceilings. The gracefully scaled floor plan encompasses 14,000+ square feet with 7 bedrooms, 10 bathrooms, 4 fireplaces, a home theater, 2,000-bottle wine cellar, kitchen pizza oven, billiard room, piano room and game room with full bar. Expansive owner's suite features a fireplace, balcony, dual closets and bathrooms-one with a sauna; a gym and a private library with built-in bookcases. Numerous French doors open to the south-facing bluestone terrace and beautifully landscaped backyard with fire pit, topiary garden and apple orchard. A pergola-covered pathway leads to the pool, tennis court and pool house.

CREAMER HILL FARM: Perched on a hillside overlooking 81+ undulating acres of seemingly remote woodlands, this substantial landed estate includes an extraordinary 14,200+ square foot main house with panoramic pond and treetop views, a three-bedroom guest cottage, a baseball field, tennis court, indoor and outdoor pools, a hot tub and a workshop/barn. Secluded at the end of two gated driveways with an exceptional sense of privacy, the estate also belongs to two private, gated associations: Partridge Hollow Association and Sterling Farm Association. Comprised of ten parcels, Creamer Hill Farm is one of the largest private land holdings in Greenwich. There are nine already subdivided, buildable lots for potential development. MAIN HOUSE: Tastefully expanded and remodeled by architects Blas and Elizabeth Bruno, the timber-clad home marries Arts and Crafts/Shingle-style exteriors with Japanese-influenced interiors. Port Orford cedar walls and oversized picture windows framing arboreal vistas bring warmth and light to grandly-scaled living spaces which include six bedrooms and eight full bathrooms. First Floor: One of the most theatrical entryways in Greenwich, the front door opens to a Japanese garden in a double-height foyer clad in cedar shingles with a vaulted glass ceiling. Framed by living palms, stone pavers create a path through a rock garden with a pond. Shoji screen-style frosted glass doors slide open to reveal the front hall with powder room and the open-plan main rooms. Anchored by a double-height stone fireplace, the dramatic living room opens to the dining room; both with double-height vaulted ceilings and floor to ceiling window walls overlooking the peaceful side yard with a terrace, pond and pool. The dining room adjoins the inviting breakfast room and cedar kitchen with high-end appliances, a marble island and beamed ceiling. French doors open to a deck for indoor/outdoor dining. Centered on a double-height stone fireplace, the sizeable family room offers multiple seating areas, a grand piano and large-scale sculptures under a soaring ceiling. A window wall looks out over a Zen garden backdropped by acres of trees. Equally impressive views are on display in the primary suite’s light-filled bathroom with picture windows overlooking the bucolic grounds. The vaulted-ceilinged bedroom with stone fireplace and dual wardrobe rooms opens to a luxurious bathroom with a sauna, steam shower, windowed shower and two soaking tubs – a nod to Japanese bathing culture. The sauna has a door to the exterior, allowing for a quick dip in the outside hot tub or pool. There are two more en-suite bedrooms on this floor as well as a two-car attached garage. Second Floor: This floor has an office, two ensuite bedrooms and an open sitting room. A skylit gallery walkway looking into the family room below leads to a one-bedroom apartment in its own wing. Lower Level: Recreation spaces abound on this finished, walk-out level with a stunning, 37-foot indoor lap pool, glassed-in gym, game room, and billiards room. Overlooking the Zen garden, the billiards room has a stone fireplace, a full bar and climate-controlled wine cellar. An office leads to a second family room with double-height stone fireplace and walls of windows looking out to verdant landscape views. There is also a pool bath, laundry room, a one-bedroom staff apartment and a second, attached two-car garage. The garage has its own thousand-gallon gas pump right outside. Guest Cottage: Bright and modern, the separate three-bedroom cottage has an open kitchen/family room, a first-floor en-suite bedroom, a powder room, laundry, and an office. The second floor has two bedrooms with a hall bath. In a sylvan paradise with ponds, streams, and woodlands, this is a rare opportunity to live in a staggeringly beautiful setting.

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!

DEER PARK ASSOCIATION: Classic English manor tastefully renovated and expanded for today's lifestyle. Highlights include original leaded windows, bespoke mantels and doors, plus antique hardwood flooring. Enter a foyer which opens to both beautifully scaled and light filled rooms. Spacious step-down living room with fireplace and carved oak mantel, formal dining room with handsome corner cabinets, cozy library with fireplace and a “bar room” ideal for both indoor and outdoor entertaining. Gourmet kitchen with large marble topped center island, butler's pantry and breakfast area all adjacent to new the family room/great room. The spectacular great room with coffered ceiling is perfect place and size for gatherings both formal and informal. French doors open to a terrace with an outdoor fireplace. A mudroom with custom built-ins and closets, two powder rooms and a full pool bathroom/changing room complete this level. Upstairs, a sophisticated primary suite with a vaulted ceiling, two bathrooms, multiple closets and a balcony overlooking the picturesque backyard and pool. Six additional bedrooms and five full bathrooms are spread-out on the second and third floors. A large playroom, a home office with custom shelves and laundry are also on the second level. The property includes 1.71 acres of professional landscaping, expansive verdant lawn, a private pool. Deer Park is a peaceful and private neighborhood coveted for its perfect setting for strolling, biking and easy access to Greenwich Avenue.

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.