luxury houses with pool for sale Fairfield County, United States

Presenting the historic Landis Gores House, an architectural masterpiece epitomizing post-WWII Modernism. Designed in 1946 by Harvard Five architect Landis Gores for his own family, it stands proudly as one of New Canaan's first Modern homes. Gores was at that time working in association with Philip Johnson. He set his own home on a narrow granite ridge astride a majestic 4-acre wooded lot; the residence brilliantly leavens the glass-walled austerity of the International Style with the natural warmth of Wrightian organic architecture.The 130-foot long, single-story form is defined by sweeping horizontal planes, full-height plate glass walls, grey-stained cypress siding, and by natural stone fireplaces, walls and terracing. Its informal, open plan is divided into three distinct pavilions, anchored by the dramatic central living and dining area featuring a raised roof and tall ceilings. Original exterior lighting design by Richard Kelly enhances the seamless integration between the avant-garde interior and its environment. An expansive rear terrace, added by Gores himself in the 1980s, features circular seating areas and an elegant oval swimming pool.Listed on the National Register of Historic Places in 2002 and held by the Gores family since its inception. The Gores family granted a perpetual preservation easement to the National Trust for Historic Preservation. This iconic property offers a once-in-a-lifetime opportunity to own a foundational piece of architectural history

Welcome to Vermont in Wilton! 1.5+ acres + I/G SW Pool! 3 Bedroom New England Cape sanctuary tucked away in a peaceful pocket of North Wilton. One meticulous owner since built in 1973, this rare find offers a charmingly rustic, soul-warming lifestyle combined with the refined convenience of Wilton living. A true testament to quality craftsmanship and generations of pride of ownership. Now, freshly painted and prepared for the next chapter. Warm hardwood floors on Main level and 4 panel sliders invite the outside in and create a panoramic view of the natural surroundings and parade of wildlife. Primary first floor Bedroom continues with hardwood, walk in closet and en suite Full bathroom. With 2 Bedrooms upstairs and 2nd Full Bath, there is no shortage of closet space with hidden closet storage! The exceptional grounds offer an incredible level of privacy on your own secret park. The in ground heated salt water pool is perfect to beat the summer heat or for outdoor poolside gatherings, framed by nature's bounty.Properties with this level of soul, history and privacy are a rare find in Wilton. If you've been dreaming of a serene escape without sacrificing proximity to town, this cherished single owned property is ready to welcome you home. Award winning schools, seconds to Rt. 7, shopping, trains, restaurants and the up and coming Georgetown revivial with fun night life, this home offers a singular, affordable lifestyle. Awaiting your updates! Property is an Estate, sold AS IS

Prestigious Hoyt Farm Tudor: An Elegant Two-Acre Oasis Near the Village. Nestled on two beautifully landscaped, ultra-private acres in the highly coveted Hoyt Farm neighborhood, this exceptional Tudor offers over 7,400 square feet of sophisticated luxury and warmth. A grand, two-story foyer welcomes you into a seamless, light-filled layout featuring a formal living room with dramatic vaulted ceilings, a handsome wood-paneled library, and an open chef's kitchen that flows effortlessly into a spacious family room with a fireplace. The primary suite is a true sanctuary, boasting its own cozy fireplace, a private balcony overlooking the grounds, a generous dressing room, and a sun-drenched, spa-like bath. Four additional bedrooms and four-and-a-half baths ensure plenty of space and comfort for everyone. Outside, your personal resort awaits: host gatherings on the tranquil brick terrace by the outdoor fireplace, swim in the stunning heated pool, or simply enjoy the park-like property framed by mature specimen trees. Complete with a three-car garage, this magnificent estate offers unparalleled privacy and convenience, located just minutes from the train, vibrant village life, and top-rated New Canaan schools.

Set on over two acres of exquisitely manicured grounds, this exceptional six-bedroom Georgian estate offers approximately 8,500 square feet of elegant living space, including the finished lower level. Beautifully proportioned interiors feature refined formal rooms, a chef's kitchen with premium appliances and marble island, an inviting family room, library, and a luxurious primary suite with sitting room and spa-inspired bath. Designed for effortless indoor-outdoor living, the resort-style grounds showcase a spectacular pool and spa, expansive terraces, outdoor kitchen with pizza oven and grills, fire pit, greenhouse, and organic gardens. Complete with a heated three-car garage and approved seven-bedroom replacement area, this is a rare Greenwich offering.

Vacation at home in this exceptional five bedroom residence, where refined design, resort inspired amenities and the flexibility of optional single level living create an extraordinary lifestyle. Tucked at the end of a quiet cul de sac on a spectacular 3.2 acre private parcel, property abuts conservation land with direct access to scenic nature trails offering tranquility and natural beauty. Designed for both elegant entertaining and everyday comfort, the outdoor living experience is highlighted by a new saltwater pool and spa. The breathtaking new main level primary suite serves as a private sanctuary complete with custom closets. Upstairs four additional bedrooms - including an optional second primary, accompany updated full baths. LL boasts wine lit wine closet, sauna and media room.

Nestled in the heart of Silvermine, tucked away, yet close to it all, this Condo and complex are truly one of a kind. This 2 bed, 2.5 bath unit has been beautifully renovated. It's sophisticated with timeless style! The sun filled, open concept floor plan is designed for both everyday comfort and entertaining. The main floor features a generously sized Living Room with sliders to a private deck with skylines views of the well manicured grounds. This room anchors the Condo with its wood burning fireplace. The Dining Room is highlighted by a gorgeous, big window and opens to the completely renovated, modern and chic Kitchen. Granite counters, stainless appliances, elegant tile work and ample cabinetry make this space shine. Upstairs you'll find the oversized Primary Bedroom that is sophisticated and relaxing. The Primary Bath is well sized and updated with a large linen closet and gorgeous tub and shower. The Guest Room is private with a full bath, making it ideal for living or as a home office. The laundry is conveniently located on this floor and adds to the condo's smart functionality. Additional amenities include an attached one-car Garage and a Storage Room conveniently located just off the garage. Residents enjoy beautifully landscaped grounds, a sparkling swimming pool, and a pet-friendly community. Just moments from the Merritt 7 Metro-North station and close to and all that Norwalk has to offer. Asking for all offers by July 16th at 9pm. Please use the SMART MLS P&S.

Overlooking Wilshire Pond, 35 Wilshire Road is a rare modern backcountry compound set on 5.29 private acres with a true resort-like feel. Designed by noted architect Gerald Schiff, the home offers approx. 7,884 sq ft, 8 total beds & baths, bold entertaining spaces, and dramatic architectural details throughout. Amenities include a natural pool with waterfall and 15+ ft deep diving well, stone pool house with guest suite, tennis court with stadium lighting, expansive sports lawn, renovated gym with floor-to-ceiling windows, 3-car garage and generator. Substantially improved by the current owners, with reimagined landscaping, enhanced living spaces & upgraded systems, this is a one-of-a-kind Greenwich retreat is designed for privacy, recreation and effortless entertaining.

Handsome brick Georgian just off Round Hill Road, renovated and expanded in 2010 with pool and spa, set on 2.41 landscaped and private acres. Custom built with exceptional attention to detail, this 5 bedroom, 6,200 +/-sq ft home embodies timeless architecture paired with a floor plan for modern living. A grand double-height reception hall creates a striking first impression, unveiling sun-drenched interiors and beautifully proportioned formal and informal spaces ideal for both entertaining and comfortable everyday living. The eat-in kitchen, accompanied by a butler's pantry, is designed to satisfy the most discerning chef. Paneled library with fireplace for work at home, or relaxation. Primary suite with fireplace and two walk in closets is complemented by four additional ensuite bedrooms. Third floor is flexible space in use as a large gym with spa bathroom. The lower level is fully finished and ready for customization. Completing this exceptional offering is a four-car garage, mudroom and laundry room. Enjoy resort-style outdoor living with pool and spa surrounded by mature plantings and exceptional landscaping providing a true sense of privacy and tranquility.

Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance. Designed by Hunt & Hunt Architects and completed in 1914 for inventor Thomas Robins, the main residence has been thoughtfully renovated and modernized throughout, including new electrical and plumbing systems, an expanded eat-in chef's kitchen, and beautifully reimagined open living and dining spaces designed for both grand entertaining and everyday living. Exceptional fixtures, finishes, and craftsmanship complement the home's historic pedigree, while every room is carefully oriented to capture sweeping panoramic water views. The main level is further enhanced by a stunning solarium with fireplace, offering a year-round retreat immersed in the surrounding waterfront landscape. The second floor is anchored by a newly improved primary suite featuring a private balcony with panoramic views across the gardens and Long Island Sound, a luxurious spa-inspired bath, and an expansive dressing room. Three additional bedrooms, a private office, and a versatile bonus room complete this level, providing exceptional flexibility for family living, guests, and work-from-home needs. A charming gatehouse with guest quarters above welcomes guests to the gated and professionally landscaped 1.67± acre property, where prominent rock outcroppings, manicured lawns, walking paths, and specimen trees create a spectacular waterfront setting. Private waterfront access accommodates kayaks and paddleboards, while a staircase on the opposite side of the property leads directly into the Long Island Sound, offering an exceptional setting for open-water swimming. Resort-inspired outdoor amenities are equally inviting, centered around a saltwater pool, pool bath, and a waterfront spa positioned to capture sweeping views in every direction. This remarkable estate offers an unparalleled lifestyle and endless opportunities for recreation, entertaining, and enjoying one of the most extraordinary settings on the Connecticut coastline.

One level living at its best! A gated drive introduces this beautifully appointed stone residence, gracefully set on over two exquisitely landscaped Mid-Country acres. Light-filled interiors offer a rare combination of scale and comfort, and are defined by dramatic ceiling heights, expansive windows, and beautifully proportioned spaces. A generous entry flows to the formal dining and living rooms, as well as the eat-in kitchen. French doors are showcased throughout the main level to create a seamless connection to the surrounding grounds and deck. The main-floor primary suite is thoughtfully positioned for privacy and features dual walk-in closets, a sumptuous bathroom that has just been renovated with spa-like finishes, and direct access to the terrace and gardens beyond. Three additional bedrooms on the main level, each with their own bathroom, provide exceptional flexibility for family and guests. Upstairs, a versatile suite with extensive built-ins, full bathroom, and adjoining exercise room offers ideal space for a home office or private guest space. A walk-out lower level includes a generous family room, anchored by a gas fireplace, and a full pool bathroom. A recently installed cedar shingle roof with copper flashing underscores the property's enduring quality and attention to detail. Outside, mature landscaping, a pool with spa, and a waterfall provide a tranquil backdrop for this one-of-a-kind offering.

Timeless 1925 Colonial reimagined for modern living. Set on oversized, stunning 3.43 private acres in a coveted Mid-Country Greenwich location, this exceptional estate offers over 7,000 square feet of beautifully updated living space. Thoughtfully transformed, the home seamlessly blends the architectural character and craftsmanship of a bygone era with sleek contemporary design and today's most sought-after amenities. Elegant formal rooms, inviting gathering spaces, and 6 spacious bedrooms are complemented by 7 full baths, while 4 fireplaces add warmth and character throughout. The stunning grounds provide a true retreat, featuring a sparkling pool, expansive lawns, and exceptional privacy. A rare opportunity to enjoy historic charm and modern luxury!

Welcome to waterfront living at its finest in sought-after Dolphin Cove. Perfectly positioned on the Long Island Sound, this beautifully renovated 4-bedroom, 3.5-bath residence offers a rare blend of coastal elegance, modern luxury, and resort-style amenities. Extensively updated throughout, the home features a stunning custom kitchen with Sub-Zero, Wolf, Bosch, and Thermador appliances, custom cabinetry, designer finishes, and an open-concept layout ideal for entertaining. The first floor has been completely reimagined with new flooring, custom millwork, a bespoke bar with wine refrigeration, updated lighting, a redesigned fireplace feature wall, and enhanced sight-lines capturing water views from the moment you enter. The luxurious primary suite was fully renovated and includes a s inspired bath, custom closets, tray ceiling with lighting, marble shower, designer tilework, and refined finishes throughout. Additional improvements include new HVAC, interior and exterior paint, updated bathrooms, upgraded electrical systems, new front entry, landscaping enhancements, sprinkler system upgrades, and countless thoughtful upgrades throughout the home.

LOCATION ,LOCATION, LOCATION! Striking, sophisticated, & contemporary w/a true WOW factor. This exceptional residence is tucked within the celebrated Golden Triangle, surrounded by some of Greenwich's most prominent estates. A rare blend of timeless modern sensibility, the home showcases stunning interiors, refined elegance, & impeccable craftmanship. Designed for today's lifestyle, the layout balances grand entertaining spaces w/ intimate, inviting rms. High ceilings, sun-filled interiors, & seamless indoor/outdoor flow create an atmosphere of effortless luxury. Every detail has curated to elevate daily living. Sited on 3 pvt acres across 2 sep. deeded lots, framed by lush landscaping, specimen trees, & vibrant seasonal gardens creating a one-of-a-kind paradise. Do not miss the apiary! Summer magic is unmatched. A delightful screeded porch ideal for lingering with the Sunday paper, a sparking pool, and al fresco dining at its best. A charming cottage offers exceptional flexibility for a guest retreat, home office, art studio, or fitness space. Capture your future memories in this dream that can come true!

GREAT INVESTMENT OPPORTUNITY-Bellavista is a 16,000+sf estate designed by architect Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus Long Island Sound views from the 2nd and 3rd floors, A truly sophisticated modern lifestyle.The residence is distinguished by its extensive integration of advanced technology systems, seamlessly embedded throughout the home. Smart-home infrastructure (lighting, climate, security,and entertainment).State-of-the-art environmental and wellness technologies (air, water, energy efficiency,and comfort). Attached 2 car garage + 5 car carriage house w lifts. 45'x20' pool. Features: Full house generator. Venetian plaster walls, bleached white oak and porcelain floors throughout, radiant heated floors (including garage), self cleaning glass beaded stucco exterior with composite slate roof, imported windows/doors and stone, and expansive property for sports and entertaining. Pet grooming room with separate laundry. Chef's kitchen and additional family kitchen. Separate staff quarters. Plans available for an additional indoor pool and underground parking garage for 8 more vehicles with a car elevator.

A classic 4-bedroom colonial in one of North Stamford coveted neighborhoods, Laurel Ledge Park. The main level of the home features a large, fire-lit, living room that opens to the dining room, anchored with matching built-in hutches. The eat-in kitchen has granite counters and stainless appliances. The island has seating for a morning cup of coffee. The paneled family room features a wall of glass inviting splashes of sunlight throughout the day. The home office could also serve as a first-floor bedroom if needed. A powder room and laundry room complete the first floor. Upstairs you will find four generous sized bedroom including the primary bedroom suite, with walk-in closet. There are beautiful oak floors in almost every room. The heated lower level has a massive game room complete with a fireplace, bar, and built in shelving. The game room has sliders leading outside to a flagstone patio. There is also a large unfinished portion of the basement available to be finished or used for storage. The property has an irrigation system and a propane-powered, whole-house generator. Recent upgrades to the home include the furnace and AC units. The 1-acre yard is tastefully landscaped and features a spacious terrace bathed in filtered sunshine for daytime fun, and equipped with landscape lighting for evening entertainment. Laurel Ledge Park Association is one of the few associations with a pool for its residents. They also host casual social events, for al LLPA annual dues are $700 for pool maintenance.

Welcome to one of Round Hill's most treasured historic properties. Originally established in 1795 as the community's first schoolhouse and later transformed into a picturesque mid-19th century center hall Colonial, this remarkable home is located within the Round Hill Historic District. Perched high on 4.6 fully fenced acres, the property enjoys broad western exposures and magnificent sunsets. The 5-bedroom main residence blends period character with modern comfort and is complemented by a separate garage cottage. Wide plank floors, sweeping lawns, mature landscaping, vegetable and flower gardens, a swimming pool, and enduring architectural details create a quintessential Greenwich country setting and a rare opportunity to own an authentic piece of local history.

Panoramic vistas of Long Island Sound extend from this gated, resort-style estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawn, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Secluded outdoor shower with exterior access powder room. Separate 2-bedroom guest cottage with kitchen, laundry and one-car attached garage. Full house generator.

DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive, manicured lawns with desirable western exposure, framed by stone walls, mature trees, and a pool. Completing the estate is a three-bedroom cottage, providing additional flexibility. Ideally serviced by public gas, water, and sewer allowing for ease of development. Perfectly positioned near schools, clubs, houses of worship, and Greenwich Avenue. Lot is 2.02 acres in RA-1. FAR = 11,878+/-

Privately tucked away at the end of a tranquil lane in prestigious Mid-Country Greenwich, this custom-built stone manor is a rare offering of timeless architecture, exceptional craftsmanship, and resort-like amenities. Encompassing more than 11,373 square feet and set upon 3.2 exquisitely landscaped level acres, the estate is surrounded by sweeping lawns, mature specimen plantings, and beautifully curated gardens that create an atmosphere of complete serenity and privacy. Designed for both grand-scale entertaining and comfortable family living, the residence features six bedrooms, eight bathrooms, and elegant interiors defined by high ceilings, abundant natural light, and refined architectural detailing. The main level boasts impressive 11-foot ceilings, gracious formal and informal rooms, a gourmet kitchen and oversized windows framing picturesque views of the grounds, pool, pool house and cottage with kitchen. The second floor, with 10-foot ceilings, is highlighted by an extraordinary primary suite offering a private sitting room, dual spa-inspired bathrooms, and two generous walk-in dressing rooms and a home office. Four additional en-suite bedrooms and a spacious laundry room complete this level. The thoughtfully designed lower level provides exceptional recreational and lifestyle spaces, including a guest bedroom and bathroom, family room, media room, fitness center, powder room, and additional space perfectly suited for the creation of a world-class wine cellar. The estate's outdoor amenities rival those of a private resort. A charming stone pool house with soaring ceilings, a fireplace, inviting living and dining areas, a kitchenette, changing room, and a full bathroom overlooks the spectacular 30' x 60' swimming pool and spa. Completing the compound is a beautifully appointed 1,500-square-foot guest house with two bedrooms, one full and one half bathroom, living room with fireplace, dining area, kitchen, office and an attached two-car garage, providing luxurious accommodations for extended family and guests. Offering an unparalleled combination of privacy, scale, and sophistication in one of Greenwich's most coveted locations, this exceptional estate represents the very best of country estate living just moments from town, schools, and commuter access.

Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated and expanded, this warmly inviting residence offers 10,664± square feet with six bedrooms, six full and two half baths, plus eight fireplaces. Above the three-bay detached garage is a renovated two-bedroom, 903-square-foot apartment with full kitchen and laundry. Leafy views from every room overlook the enchanting landscape. There is a pool with spa, fenced vegetable garden and fenced chicken coop. With so many aspects of special distinction, this is a wonderfully unique compound that captures the feel of the English countryside in a tranquil mid-country location. Includes legally permitted medical office.

An approximately 8,000 SF Connecticut Colonial on more than seven acres in mid-country Greenwich, on one of the town's most established addresses. Seven bedrooms, eight fireplaces, a formal dining room, and a slate-tile roof -- a 1923 residence with period character on a scale of grounds increasingly rare in mid-country. A long private drive rises from the road, with the land revealing itself gradually: a nearly one-acre pond at the back of the property, a swimming pool, tennis court, two-bedroom guest cottage, and a detached three-car garage. The amenity stack -- pond, pool, tennis, cottage, garage -- is essentially irreplaceable on a single Greenwich parcel and reflects six decades of stewardship by one family. This is part of the four-parcel Spring Farms at Round Hill assemblage, brought to market for the after sixty years in one family. For buyers also considering renovation, expansion, or longer-term redevelopment, Workshop/APD -- leading architecture and interior design firm -- and Davis Chase Homes are available to design and build on the buyer's timeline. See the full Spring Farms at Round Hill brochure for context on the broader collection: https://issuu.com/workshopapd/docs/rhg_marketing_brochure

Privately set on more than 6 extraordinary acres within the prestigious Khakum Wood Association, this award-winning estate offers distinction, privacy, and architectural excellence in an A+ location. Clad in limestone, fieldstone, and stucco and crowned by a graduated slate roof, the residence is defined by timeless elegance and exceptional quality. Bright interiors feature soaring ceilings, imported natural materials, and superb craftsmanship throughout, while a modern floor plan is designed for both entertaining and daily living. Stone terraces on every level overlook sweeping level lawns. Complete with a separate apartment for guests or staff, 7 garage bays, pool, and bocce court, this is unlike anything else on the market.

Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside’s prestigious Indian Head Association, this storied property occupies the historic grounds of railroad magnate Henry Francis Shoemaker’s former compound—a Gilded Age legacy that later served as the backdrop for the iconic Cedar Cliff Beach Club of the 1920s. The estate bears the name Shoemaker originally gave his villa, ‘Cedar Cliff’—a designation that eventually defined the very road on which it stands today. Elevated high above the flood zone and offering 1,250 +/- feet of direct water frontage, the property unfolds with extraordinary scale and privacy. A sweeping, manicured lawn rolls gracefully toward the shoreline, creating a striking foreground to the panoramic coastal vistas and an exceptional setting for grand-scale entertaining. Each of the eight oversized bedrooms is oriented to capture breathtaking water views, while interiors blend the romance of pre-war craftsmanship with modern refinement—soaring ceilings, intricate millwork, antique wood floors, a three-level elevator and a professional recording studio. The East Wing, constructed in the early 2000s, introduces a new dimension of contemporary luxury, anchored by a sophisticated primary suite and complemented by a custom office, wine cellar, and private theater capable of accommodating up to twenty guests. The grounds rival those of a world-class private resort. A substantial stone pier and deep-water dock provide immediate access to open water, while a seaside tennis court with pergola and lighting offers championship-level play. At the water’s edge, a pool and spa are paired with a fully realized cabana featuring a fitness center, kitchenette, full bathroom and changing rooms. Sculpted into the eastern landscape, a series of stone terraces with a bluestone bar directly overlook Greenwich Cove and the vast protected expanse of Greenwich Point Park. Meticulously maintained and thoughtfully enhanced, the estate includes a newly installed Ludowici terra cotta roof, rebuilt sun decks, custom East Wing windows, and a full-property generator—ensuring seamless comfort and continuity. With access to a private beach and watercraft facilities, and located less than an hour from Manhattan and minutes from Westchester County Airport, the property offers a rare convergence of seclusion, scale, and global accessibility. Cedar Cliff is a singular offering for the most discerning buyer—an incomparable experience of refined luxury, inviting residents and their guests to revel in the natural beauty of one of the finest estates on the East Coast of the United States.