luxury houses with pool for sale Connecticut, United States

Set on over 20 breathtaking, wooded acres, this property offers a rare blend of privacy, natural beauty, and flexible living. This contemporary split-level home is filled with natural light and thoughtfully positioned to capture sweeping hillside views from nearly every angle. With five bedrooms and 3.5 baths, including a private in-law suite with its own entrance, the home provides exceptional versatility for multi-generational living or guest accommodations. Outdoors, the property unfolds into a true retreat-meandering private hiking trails, a serene spring-fed pond, and open fields dotted with fruit trees create an idyllic country setting. Entertain with ease around the in-ground cement pool, surrounded by a stamped concrete patio, or host unforgettable gatherings beneath the stunning pergola dining area. Recent improvements, including a new roof make this move in ready. With its unmatched acreage, scenic vistas, and boundless potential, this is a unique opportunity to create a truly special lifestyle property in the heart of Durham.

Welcome to this quintessential Greenwich home, fabulously refurbished and sited on a generous and private .91 acre in central Greenwich. Within an easy reach to schools, train stations and all of the amenities the town has to offer, this 4 bedroom home is move-in ready. The formality of the living and dining room is complemented by the open eat-in kitchen and family room. There are several home ''offices'' from which to chose! Perfect for the summer months, the heated pool is naturally shaped and acts as the centerpiece to the mature and landscaped garden. Two car garage is a benefit.

Nestled in Westbrook, Connecticut, 331 Dennison Road is a quintessential private retreat that seamlessly blends indoor comfort with outdoor splendor. This casual residence features a bright, open floor plan highlighted by a grand great room with a cozy fireplace, perfect for quiet evenings or lively gatherings. The kitchen opens directly onto a charming patio, ideal for alfresco dining overlooking the pool and woods. Outside, an inviting inground pool is encircled by a meticulously curated flower garden, while a dedicated, fenced-in vegetable garden with raised beds and a custom shed awaits the home gardener. With the convenience of a spacious first-floor primary suite, this home offers a thoughtful layout designed for modern living in a serene, park-like setting. Offering geothermal heating/cooling system and owner owned solar panels for a very efficient low cost utilities.

**7/26/26 Open House Cancelled** Updated, 4-bedroom, 2-bathroom New England gem boasting 2,348 square feet of thoughtfully designed living space. Pride of ownership shines through with improvements already completed for you, including a new roof (2026), freshly painted exterior (2026), a replaced septic system (2021), and a new well (2020). Interior features include a gorgeous remodeled kitchen with quartzite counters and stainless steel appliances that flows into a family room featuring dramatic cathedral ceilings and easy access to the rear yard entertaining space. The exterior is a true staycation paradise. The level backyard hosts a pristine in-ground pool paired with a dedicated pool shed equipped with electricity-ideal for pool storage. Peace of mind thanks to an upgraded 200-amp electrical service complete with a generator transfer switch. Perfectly situated just north of Route 1, this home offers the ultimate shoreline lifestyle. Enjoy being just a 5-minute drive to Madison's quintessential town center and a quick 8-minute drive to the beach. Move right in and start enjoying summer by the pool!

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.

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.

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.

Welcome to your private rural sanctuary in scenic Warren. Tucked away on expansive acreage with its own serene pond and gorgeous grounds, this unique, single-level ranch offers the ultimate blend of privacy, natural beauty, and incredible potential. Being sold entirely as-is, this estate is ready for its next steward to bring their creative vision and make it truly shine. The primary residence features a comfortable two-bedroom layout designed for easy, single-level living, which flows effortlessly out to an in-ground pool and dedicated pool house-perfect for summer entertaining or quiet afternoons soaking in the pastoral views. Adding immense value and versatility is a fully self-contained, two-bedroom in-law apartment complete with its own private kitchen, full bathroom, and independent laundry. Embrace the very best of Litchfield County living; you are minutes from pristine lakes, hiking trails, and endless outdoor recreation, all while enjoying close proximity to the historic charm, fine dining, and boutique shopping of nearby Kent, Litchfield, and Washington Depot. Opportunities to own significant acreage with these multi-generational amenities in a prime, low-tax Warren location are rare. Bring your imagination and your updates, and claim this countryside haven as your own. All this just 2 hours from Manhattan. Bedroom count includes legal in-law unit.

A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

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.

'La Gentilhommière' is a unique property in North Stamford, inspired by Château de Givenchy-le-Noble in France. Built 20 years ago, this property exudes an authentic French charm with imported materials gracing its construction. From the stately Pierre de Bourgogne limestone that adorns its exterior to the exquisite 18th-century French elements found within, every detail evokes a sense of timeless elegance. Inside, you'll discover the beauty of Versailles wood parquet flooring and the comfort of double-paned insulated windows, each adorned with brass European-style handles that enhance the estate's allure. The heart of the home showcases a Smallbone kitchen, complete with a La Cornue Château range, while radiant-heated floors and numerous other exceptional features elevate this property to a class of its own. Bordering the Helene Altschul Land Trust, ensuring no adjacent construction, the privacy in this estate is second to none. The property includes 2 newly built guest houses, one pool house featuring a kitchen with a private bathroom, and a studio house with an inspiring view to stimulate the mind. The newly built 12 meter pool is surrounded by amazing landscapes, as the large schist boulders are reminiscent of Central Park. Combining historical aspects that cannot be duplicated, in addition to the modernized renovations, this property will appeal to anybody with its unprecedented versatility. Conveniently close to the Merritt Parkway and Manhattan, it offers a rare opportunity for discerning buyers looking for quick access to the city.

Private New Canaan Oasis: Bespoke Luxury can be found in this modern version of a traditional centerhall colonial in prestigious New Canaan's West School district. This custom-built Lukes Wood estate underwent a spectacular renovation by Award-winning RR Builders, updating the sophisticated main residence to over 7,000 square feet of turnkey luxury. The expansive floor plan boasts 6 generously appointed bedrooms - each featuring an ensuite bath and walk-in closet alongside elegant formal living and dining rooms, a private office, a wine cellar, a butler's pantry, and a finished walk-out lower level with a full bath. At the heart of the home, a fully appointed chef's kitchen with a double island and professional-grade appliances flows into a sun-drenched breakfast room and a magnificent great room, which showcases a floor-to-ceiling stone fireplace, cathedral ceilings, and rustic beams. French doors transition seamlessly to an outdoor sanctuary featuring a 45' x 22' heated gunite pool, an expansive terrace, a pavilion with a firepit, private walking trails, plus a custom-built barn that offers additional space for cars, equipment, a gym, art studio, or large office space delivering an unparalleled, ultra-private retreat close to New Canaan's top-tier schools and vibrant community.

The Dean House, a/k/a The Horsford Homestead, a/k/a The Howe's Home is arguably the oldest residence in Falls Village (Canaan), CT. The original structure was built in 1735, with a major, two story addition added in 1804. Many details have withstood the test of time, and this home is a stunning statement for any old-house enthusiast. If you envy the history as a preservationist, conservationist, or restorationist, you just found your personal Xanadu. From the original fireplaces and paneling to the structural bones in the attic and basement, all the right features are here, as spacious rooms, cozy environs, and heartfelt warmth are the mantras. Much of the original trim, flooring, doors, and moldings are prevalent, and that impact speaks volumes. The bathrooms are recently updated, and there are newer appliances. The cedar roofs are no more than 7 years old. The outdoor environment is lush and well maintained. There's a kidney shaped in-ground pool, beautiful gardens, and even a large flat lawn that once served as a home to a full-sized English croquet court. The large old barn dates well back in time, and there's a gazebo for quiet reflection and outdoor meals. Several other smaller buildings exist for all types of storage. And then there's the newer building (1997) - a combination of a two-car garage, a huge studio/workshop, a smaller storage room, and a roughly 1700 sq. ft. in-law apartment on the second floor. Approximately 30 acres of farmland is organic. Drive-bys are welcomed, but please do not pull in the driveway without a confirmed appointment.

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.

This magical light-filled New England 7,945 s.f. cottage takes full advantage of its private waterfront location overlooking LIS and a wildlife estuary. Sited in a private community on 1.27 acres with 300' of water frontage provides panoramic water views of sunrises and sunsets from most rooms. A heated swimming pool, two beaches and mooring rights guarantee outdoor pleasures. There is also room for a tennis court. The house was expanded from its original 1912 footprint and fully renovated over 3 years (1987-1990) with the best curated materials including Tischler high impact windows throughout. French doors in the 18' ceilinged living room, dining room and family room all open to a flagstone terrace. The 6+ bedrooms, all but one with ensuite bathrooms, can be accessed by elevator or front and back stairs. There is also a separate handicapped accessible apartment. The impressive, newly renovated kitchen with table sitting up to eight is equipped with top of the line appliances. Privacy, gracious living space and endless recreation possibilities make this special property an ideal retreat. Check floor plans for more details.

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!

This antique home, originally built in the 1700s, has been thoughtfully expanded into a home where antique bones meet mid-century ambition. The original structure anchors the property with a country kitchen open to a casual dining area, with wide board floors, a hand-hewn beam overhead, and blue-and-white tile that gives the space real personality. The kitchen flows into a living room with fireplace; up a level, a bedroom (currently used as a closet) and a full bath.The mid-century addition shifts the mood entirely: a dramatic great room with vaulted ceiling, exposed redwood paneling and beams, stone fireplace, and a sense of scale you don't expect until you're standing in it. A sunroom and two additional bedrooms sharing a bath round out the wing. Outside, the in-ground pool sits tucked behind a white picket fence with mature trees all around. A detached two-car garage and backup generator complete the package. Set on 6+ private acres in the Taconic section of Salisbury, this is the perfect country retreat with genuine character.

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!