luxury houses with pool for sale Connecticut, United States (page 5)

YOUR OWN PRIVATE COUNTRY CLUB! Enjoy the expansive 3500 sf granite terrace, a heated saltwater swimming pool, a deep water dock and a pool house with a full kitchen and seating for 10! This modern masterpiece, sited to take full advantage of a private 1.6 acre waterfront location overlooking North Cove and the Connecticut River has been constructed with the best curated materials. 20 Saltus Drive offers a luxurious, comfortable lifestyle with panoramic water views from almost every room. The great room (30' x 40') has soaring ceilings, a remarkable, double sided stone fireplace and a window wall creating an expanse of glass facing picture perfect water views. Glass pocket doors open to the dining room which flows into the impressive kitchen with table and counter seating. Additional notable spaces on this level are a home theater with an 8'+ screen and two bedroom suites (all five bedrooms have ensuite baths; four also enjoy separate sitting rooms). Access the second level either by elevator or a striking marine stainless steel, floating staircase. To the left are two additional bedroom suites while to the right is the palatial primary suite which includes a bedroom with fireplace, a large bathroom, walk-in closets, a laundry, an office and a sitting room. These three suites also have water view decks. Nearby is downtown Old Saybrook with its restaurants, shops and the Hepburn Cultural Arts Center.

'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.

Welcome to 14 Cook Street, a charming circa-1900 Victorian located in the heart of Washington Depot. Rich in history, this home was once known as Cook's Boarding House, a local inn that helped shape the character of this picturesque New England village. Offering approximately 1,800 square feet of living space, this 4-bedroom, 2-bath home features a traditional layout with a living room, dining room, den, and kitchen with pantry. Period details blend seamlessly with comfortable living, providing both character and functionality. Set on 1.3+ acres, the property offers a rare combination of in-town convenience and private outdoor space. The level lot is enhanced by mature landscaping and includes a fenced in-ground pool-ideal for summer entertaining or quiet relaxation. Located just steps from the village center, enjoy easy access to local shops, cafes, and everyday conveniences. Washington Depot is widely known for its scenic beauty, historic charm, and proximity to Lake Waramaug, Steep Rock Preserve, and numerous outdoor recreation opportunities. Ideally situated between New York City and Boston, this property is well-suited as a full-time residence or weekend retreat. A unique opportunity to own a historic home in one of Litchfield County's most desirable towns. Buyer backed out 1 week before closing for personal reasons! Brand new pool liner, ready to move in!

Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a 2014 transformation. The volume of the rooms, soaring ceilings, proportion of the windows and quality of light create a sense of serenity and openness. Stately yet modern, this is a house that can be lived in with comfort and ease. Adjacent to the dining room gallery is a walled garden with a custom pavilion for entertaining. The 52 acres were transformed in collaboration with noted landscape architect Perry Guillot into a private park with a dramatic meandering approach, a great lawn, and woodland trails amongst streams and waterfalls. A 60 x 22 pool and tennis court were also added. At the discrete entrance to the property are twin cottages; a caretaker residence and a gym. Privacy and proximity to NYC and airports along with this caliber of property make this a world class offering and a rarity by any standards.

Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the open, landscaped property. Lofty ceilings and walls of glass create magical interior spaces, a perfect setting for an art collector. Private wings radiating off the house center accommodate guests comfortably. A hidden theater and a stunning Moroccan lounge with bar are some of the special features of this extraordinary property. The barn-style pool house with full kitchen, bath and spacious gym, the pool, and a heated paddle tennis court are all easily accessible from the main residence. The updated stone gatehouse accommodates guests or staff. A two story office pavilion is tucked in a private garden area. The landscape offers open vistas, meadows and an orchard. There is potential for equestrian use. Live in ultimate style and easy elegance at this private retreat just a quick commute to NYC and airports. Fairfield and Westport town centers are in close vicinity. Enclosed behind a stone wall and surrounded by a 155 acre nature preserve, this is a uniquely private haven. Main residence 9129 sq ft. Barn 2400 sq ft., Guest House 2800 approx. Total 14,329 sq ft. Whole property generator. Solar and geothermal systems. Water filtration system. Two laundries. Slate roof. Heated parking. Dog washing station. Wine room. Orchard. This offering encompasses three lots: 4800 Congress St consists of main residence, 10.92 acres, office pavilion, pool/barn pool house and heated paddle court. 4900 Congress St consists of stone guesthouse on 25.87 acres with fields, meadows and pond. 5010 Congress St is open land: 2.12 acres with potential for barn or tennis courts and tennis pavilion. Equestrian use potential for entire property. All measurements approximate.

Experience the perfect blend of timeless character and contemporary convenience in this stunning colonial. The residence welcomes you with an open-concept floor plan and an expertly updated chef's kitchen, featuring premium Sub-Zero refrigeration for an upscale culinary experience. Designed for both relaxation and entertaining, the home offers four bedrooms and three full baths, including a cozy family room ideal for intimate gatherings. The upper level is anchored by a generous primary suite, complete with a private home office and expansive closets accented with stylish barn doors. The lifestyle continues outdoors in a private, fenced-in backyard oasis featuring a pool, a cabana and lush green space. The town center, schools, library and beaches are just a walk from this gorgeous home offering a pleasant walkable lifestyle. At 24 Cottage Place, you can enjoy the soul of the past with every modern creature comfort at your fingertips. Disclaimer: Field card states 3 bedrooms but there are 4 bedrooms in this home.

You don't look at your home...you look out from it. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering and execution where every material, finish and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a faade clad in premium Thermory wood siding beneath a Spanish slate roof an exterior that feels both grounded and enduring..Walls of Aluprof glass dissolve the boundary between interior and Long Island Sound, drawing light deep into nearly every principal room. The result is a seamless connection to the water, with unobstructed views that are impossible to replicate. Inside, large-scale radiant-heated Porcelanosa tiles grace the main and lower levels, setting a warm, modern foundation. At the heart of the home, a statement kitchen delivers both performance and presence; featuring custom Vimora cabinetry, top-of-the-line Gaggenau appliances and a fully equipped secondary prep kitchen designed for effortless entertaining at scale.Upstairs, European white oak introduce warmth, while radiant heat continues throughout all main spaces and baths reinforcing a consistent commitment to comfort and precision. The primary suite is conceived as a private retreat, oriented entirely toward the water. A fireplace anchors the space, while a private deck leads directly to the heated pool below. The bath offers a spa-like experience, featuring a sculptural soaking tub positioned toward the view and a separate steam shower. Custom Italian wardrobes complete the suite, incorporating bespoke detailing, opaque glass, and integrated features throughout. Additional bedrooms on this level are all ensuite, each perfectly positioned to capture water views.nThe lower level opens into a fully realized entertaining environment featuring a wine room, fitness center with sauna, guest accommodations, and a dramatic lounge anchored by an illuminated marble bar and a 162-inch screen.nA concealed underground car gallery, accessed by hydraulic lift, offers a discreet and highly engineered space designed for discerning collectors. Outdoors, an expansive terrace and heated waterfront pool overlook the cove, creating a setting defined by privacy and open water. Minutes from Tod's Point, Metro North, and the village of Old Greenwich, the property occupies that rare overlap of seclusion and convenience. With five bedrooms, five baths, and two powder rooms, every element has been resolved with intention. This is a rare chance to own a crown jewel waterfront property that stands in a league of its own. A defining waterfront residence where design, setting, and permanence align at the highest level.

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see.

This incredible modern Mediterranean Villa offers incredible view of the State capital from almost every room. This Home is a showstopper!!So much detail, Custom floor to ceiling windows. This home is one of a kind in State of CT, One of the most desirable area of town. 4 bedrooms and 4 and a half bathrooms. Included is a 4-car garage with double-wide black garage doors that has glass windows and very bright LED lights throughout. Up to a 6-car garage located under the home. Located on over 7 acres of land and has a private driveway. The home offers a stunning front entry with beautiful, suspended lighting, front steps are blue stone, front stairs, and a patio in Italian Slate pressed concrete. The elegant exterior of the home features white stucco with black trim. Stunning courtyard with gardens, heated inground pool surrounded by AstroTurf, pool house that is attached to the home, and an outdoor kitchen with 3 refrigerators, bar station as well as extra burners in addition to the full grill by Paradise Grill. Built-in lights and speakers. And the second island gives bar seating for 5 comfortably. The living room/dining room is open concept with double back French doors to both sides of the house for maximum light, with exposed black beams. A 70-inch 3-sided fireplace by Davinci with a wine room off of it and an 85-inch LED TV above for maximum entertainment.

Welcome to 145 Pine Hill Rd. A renovated Organic Modern home mixing both modern amenities and rustic charm. Adorned with random plank flooring, hand-hewn beams and massive field stone fireplace. The 12ft sliders in the Living Room allow for access onto the spacious deck. The culinary space is a chef's haven, equipped with state-of-the-art appliances & premium finishes that inspire culinary creativity. With southern exposure, the house offers plenty of opportunities for sunlight, expansive views off the deck along with a great setting for gardening. Each of the 4 bedrooms provides a unique space, while the 4 baths feature refined fixtures & chic designs, ensuring every personal convenience is met. Off the primary bedroom is a retreat unto itself, featuring a circular patio where one can reflect in the joyful sounds of the water fountain or unwind in the private hot-tub. The lower level is another entertainment area with full bathroom and spacious family room with wet-bar which opens to the swimming pool and deck areas. Great for the avid outdoor enthusiast where there is plenty of hiking, mountain biking and fishing.

Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and informal living spaces, a dramatic entry, private library, expansive kitchen, first-floor guest suite, elevator, and finished walkout lower level with golf simulator, wet bar, wellness gym, and cold plunge. Outdoor amenities include terraced landscaping, stone walls, a 20x40 pool with integrated spa, and a separate pool house with kitchenette, bath, and fireplace. Unique opportunity to customize select finishes and layout while in current stage. Renderings, plans, specifications, and features subject to change. A singular offering for those seeking a generational Greenwich estate with privacy, provenance, and architectural permanence. Merrit to Round Hill Road

Custom designed and built to exacting standards, this phenomenal backcountry lakefront compound was built to exacting standards, offering fabulous privacy and flexibility for families, guests, and staff. A prominent local design-build firm created a masterpiece that combines pre-war elegance with substantial entertaining and modern lifestyle amenities. Multiple structures, including a large pool house/sep guest house and a renovated original stone house set on Topping Pond-a perfect getaway. Gated driveway opens to mature landscaping and classic New England exterior elevations. The first floor features a generous, light-filled kitchen and informal/formal dining, his and hers offices, a large mudroom with a pet area and a traditional flower 'cutting' room, a 4-car garage, and separate stairs to a 2-bed/2-bath guest area with a sitting room. The second floor contains a primary suite with a balcony, a generous WIC, laundry, and 2/3 further family bedrooms. Finished the 3rd floor with a bed/bath/yoga room. Enormous lower level with triple-height basketball court, gym, entertaining area, and staff suite. The guest house includes a generous bed/bath and living area along with a pool house/bar/changing area and laundry. Last but not least is the private and charming lakefront cottage as a flexible 'escape from it all' den/office or entertaining/further guest area. Superbly decorated and maintained, this unique home has to be seen!

Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and informal living spaces, a dramatic entry, private library, expansive kitchen, first-floor guest suite, elevator, and finished walkout lower level with golf simulator, wet bar, wellness gym, and cold plunge. Outdoor amenities include terraced landscaping, stone walls, a 20x40 pool with integrated spa, and a separate pool house with kitchenette, bath, and fireplace. Unique opportunity to customize select finishes and layout while in current stage. Renderings, plans, specifications, and features subject to change. A singular offering for those seeking a generational Greenwich estate with privacy, provenance, and architectural permanence. Merrit to Round Hill Road

A rare blend of scale, privacy and value, this beautifully maintained Redding retreat offers over 6,000 square feet of flexible living space. From the gracious front entry, the home unfolds with purpose and ease. To the right, a private library/home office creates a quiet place to work. Straight ahead, the living room frames peaceful views of the pool and grounds, while the formal dining room leads toward the heart of the home: a large eat-in gourmet kitchen open to an impressive family room with soaring ceilings, walls of windows, and abundant natural light overlooking the property. The traditional second floor offers a spacious primary suite with walk-in closets and serene backyard views, along with three additional bedrooms. The finished lower level adds tremendous versatility, featuring a large suite and lounge area ideal for guests, au pair, or in-law living, with direct access to the mudroom, garages and a separate exterior entrance. A second exterior entrance leads to a fully private studio or workshop. Outdoor living is a standout, with an expansive deck surrounding the pool and generous space for entertaining, relaxing and enjoying the private setting. The detached pool house/guest house adds incredible flexibility with a living area, kitchenette, bedroom and loft space. With exceptional square footage, privacy, lifestyle amenities and tremendous value compared with pricing being achieved in surrounding Fairfield County towns, this is a must see property.

A four-season retreat-where open lawns, a beautiful pool, and the surrounding landscape create a sense of quiet luxury. Set along the Saugatuck River on a quiet private Lower Weston Cul de Sac, this architecturally distinctive contemporary is privately sited on 2.49 acres, offering scale, light, and direct river access in one of Weston's most desirable settings. A soaring cathedral ceiling Great Room anchors the home, defined by dramatic vertical volume, expansive glass, and extraordinary natural light. A central fireplace adds warmth and balance to the openness, creating a space equally suited for entertaining or quiet evenings at home. The kitchen is thoughtfully positioned at the heart of daily living, opening seamlessly to the family room with fireplace. French doors lead directly to the deck, Gunite pool, and BBQ terraces, creating effortless indoor outdoor flow and making summer gatherings and everyday living feel connected to the landscape. A striking three season porch with cathedral ceilings extends the architectural expression and provides a serene transitional space overlooking the natural surroundings. A substantial private office with fireplace offers an exceptional work from home retreat. The primary suite is a sanctuary featuring its own fireplace and a newly renovated spa bath. 3/4 additional bedrooms provide comfort and flexibility. The grounds unfold toward the Saugatuck River, offering direct access for kayaking, fishing, or simply enjoying the peaceful waterfront setting. In winter months, upper level glimpses of the river add seasonal dimension. Additional highlights include a three-car garage and solar for energy efficiency. Architecturally expressive yet comfortably livable, this lower Weston contemporary blends light, privacy, and natural beauty just minutes from Westport amenities, commuting access, and Weston's award-winning schools.

Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft ceilings, custom paneling, character grade oak floors, refined millwork, and expansive windows. Sun-filled living and dining rooms complement the great room with a sleek 60inch fireplace and reclaimed beams. The chef's kitchen includes full size SubZero refrigerator and freezer, Wolf cooktop and double ovens, quartzite waterfall island, custom cabinetry, and walk-in pantry. A private office with built ins enhances work from home convenience. Outdoor living shines with a covered porch, granite patio, outdoor kitchen, and direct access to the 20x40 saltwater pool. The luxurious primary suite offers vaulted ceilings with antique beams, oversized walk ins, and a spa bath with custom vanities and textured tile. All five second floor bedrooms are ensuite. The finished third floor adds a full bath, office/craft room, and playroom. The walkout lower level includes a bedroom and bath, gym, wet bar, media room with raised platform, and large recreation area. **Images with exterior are AI Altered. House is complete inside. Exteriors complete 6/15/26.** **See Addendum**

A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and well-proportioned spaces create an environment that feels both elevated and effortlessly comfortable. At the center of the home, a beautifully designed kitchen opens to expansive living and dining areas, creating a seamless flow for both everyday living and entertaining. The layout flows easily with ample room for work-from-home, multi-generational living, and evolving lifestyle needs. A main-level suite with a full bath provides privacy and versatility-ideal for guests, a dedicated office, or an extended family. Every detail accentuates comfort, function, and understated luxury. A back yard patio with pool abutting a nature preserve offers privacy with open space and the ease of in-town living. Positioned near Nash Pond and close to local nature trails and amenities, the home also offers exceptional convenience-walkable to the Post Road and just minutes to downtown Westport, shopping, dining, and Metro-North train service to New York City. Luxury new construction in Old Hill, Westport, CT-where location, design, and lifestyle align in one of the town's most desirable settings.

The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by noted architects Visscher and Burley, this Colonial Revival style home has undergone thoughtful renovations over the years to preserve and enhance its original character. High ceilings, oversized windows, detailed millwork and sun-filled rooms create a sense of warmth and sophistication. Recent renovations include a new cedar roof on both house and barn, a like-new pool, spa & mechanicals, refinished hardwood floors, updated HVAC and new appliances. A unique highlight of this estate is its location across from Nyala Farms, offering scenic views of 50 acres of open meadows and fields with a deed restriction preventing any further development. Enjoy the ultimate lifestyle, minutes to the train, beaches, schools, shops and fine dining.

Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn. Designed for both grand entertaining and everyday living, the home features an extraordinary backyard anchored by a stunning pool and attached pool house, creating the ultimate resort-style setting. Inside, the thoughtfully designed floor plan includes a sought-after first-floor bedroom, expansive sun-filled living spaces, and seamless flow throughout. The dramatic family room showcases soaring 20-foot ceilings with striking wood beams, while the modern renovated kitchen beautifully blends contemporary style with everyday functionality. The second floor offers five spacious bedrooms along with an oversized playroom/flex space. A partially finished basement provides additional recreation room and storage possibilities. Zoned for highly desirable Long Lots Elementary and Bedford Middle School, this exceptional property combines timeless architecture, incredible outdoor living, and an unbeatable cul-de-sac location in the heart of Westport. Sturges Hwy to Daniel Court

61 High Ridge Ave is an extraordinary estate in the heart of Ridgefield's Historic District, set atop one of the town's highest elevations with sweeping skies, radiant sunsets, and far-reaching views beyond the Hudson River. Custom built in 1997, this distinguished Stone Manor blends timeless elegance with exceptional craftsmanship. Encompassing more than 8,000 square feet across three levels, the residence showcases a stone facade, slate shingle roof, five generously sized bedrooms, and 6.1 baths. A dramatic two-story foyer opens to refined formal rooms and a handsome library, enriched by mahogany windows and doors, hardwood floors, and exquisite millwork. The expansive eat-in kitchen flows seamlessly into the inviting family room with fireplace, creating an effortless setting for everyday living and gracious entertaining. Upstairs, the serene primary suite offers two walk-in closets, a fireplace, and a private balcony, while additional ensuite bedrooms provide comfort and privacy. A finished third floor adds versatile space for wellness, work, or leisure. Beyond the main house, a separate studio cottage with full bath and fireplace offers elegant guest or flexible accommodations. Set on 2.61 landscaped acres, the estate is further enhanced by a pool, tennis court, and four garage bays, completing this rare and luxurious retreat.

A truly unforgettable and exceptionally rare offering-Rogers Island presents an exciting opportunity to own a private island paired with a mainland residence, delivering the perfect balance of seclusion and convenience. The mainland property includes its own dock, parking, and support space, making access to the island with a 5-minute boat ride, seamless and effortless. Just offshore, the island unfolds into a peaceful, panoramic retreat surrounded by water views in every direction. Designed for both relaxation and entertaining, the estate features a 10-bedroom main residence with 6 full and 2 half baths, a 4-bedroom/2.5 bathroom guest house, artist's studio with half bath, and dedicated staff quarters. A mahogany wraparound porch invites you to take in the scenery, while meandering granite pathways guide you thru the grounds which offer an exceptional collection of amenities: an in-ground heated pool with pool house and separate bath house, tennis court, Nicklaus-designed putting green, koi pond, greenhouse and two docks. A charming gazebo sits at the edge of the property-perfectly positioned to capture sweeping views for miles. Quiet, expansive and thoughtfully designed, Rogers Island is a legacy property where generations can gather with ease, hosting everything from intimate weekends to large-scale entertaining, all set against a backdrop of uninterrupted water views, timeless coastal beauty and a sense of privacy that's increasingly impossible to find.

Timeless Tudor architecture defines this residence, offering over 5,400 sqft of living space on a spacious, fenced lot with sweeping views in every direction. Intricate woodwork and refined detailing highlight the home's rich character throughout. A grand foyer introduces the home's scale, leading to an exquisite living room with hardwood floors and fireplace. Adjacent, a private office featuring built-in bookcases and French doors. Beyond, the expansive dining room is ideal for hosting, flowing seamlessly into the updated kitchen, featuring a custom walnut island with workstation sink, new appliances, and a sun-filled eating area overlooking a tranquil pond. Next, the great room showcases 20-foot ceilings, exceptional woodwork, a floor-to-ceiling stone fireplace, and a wet bar. Above, an open balcony walkway overlooks the lower level, offering a dramatic vantage point that enhances the home's openness while creating a graceful connection between floors. A main-level bedroom and full bath offer flexibility for guests or a secondary office. The second floor offers a primary suite with generous proportions, complete with fireplace, and custom walk in closet. The primary bath includes an open shower with multiple spray features, a water closet, and soaking tub. Outdoor amenities include a Gunite pool and hot tub, along with a 3-car garage, new oil tanks, new well pump, and irrigation system. Defined by craftsmanship, scale, and setting, this home leaves a lasting impression.

20 Cherry Lane is a rare Georgian Colonial estate set on nearly 2.5 flat, manicured acres bordering 50 acres of protected conservation land and hiking trails. Offering over 7200 sqft, with an additional 2100+ sqft lower level, this home combines exceptional scale, modern updates, and long-term value. Designed for entertaining and everyday living, the renovated chef's kitchen features double marble islands, double ovens, dual dishwashers, navy subway tile, and a custom coffee/wine bar, flowing into the oversized Great Room with a massive stone fireplace, full bar, and direct access to the resort style pool area. The flexible layout includes 6 bedrooms, a luxurious primary suite with private balcony and oversized walk-in closets, double office/conference spaces, library, homework zone, first floor guest suite, and a fully self contained in-law/au pair suite with private entrance, kitchen, and living area. The renovated lower level offers a gym, infrared sauna, indoor hot tub, wine cellar, spa lounge, oversized playroom, and custom bunk room. Outdoors enjoy a restored pool and spa, sports courts, playground, gazebo, fire pits, and multiple entertaining areas. Major upgrades include a new 2024 roof, updated HVAC, plumbing, electrical, and a renovated 4 car garage with smart-tech doors. Move in ready with the option to be sold fully furnished, this exceptional estate offers incredible space, infrastructure, and upside in a premier school district.

Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary suite offers its own stone fireplace and a luxurious bath with radiant heated floors. The kitchen is equipped with Wolf, Bosch, and Liebherr appliances. The dining room features a hidden dry bar and a glassware cabinet, with sliders to the top deck for outdoor dining if desired. Upstairs, there are three additional bedroom suites with updated baths, plus a smaller third-floor bedroom ideal for an office or flex space. The finished walk-out lower level includes radiant heat, a bedroom, a full bath, an office, a gym, laundry, and a kitchenette. Outdoors, enjoy a heated Gunite pool and spa with a bluestone patio, surrounded by serene woodland views. Additional features include the Sonos system, whole-house generator, and air purification. Minutes to town and top-rated schools, this move-in-ready retreat is ideal for weekend or year-round living.

Set on over four and a half acres of private, level grounds in one of New Canaan's most sought after locations, this exceptional estate offers a rare combination of scale, privacy, and close to town convenience. Originally built in 1962 and thoughtfully expanded, the property unfolds as a true compound. The main residence features five bedrooms, seven baths, and beautifully proportioned living spaces anchored by three fireplaces. A seamless connection between the chef's kitchen and family room creates the heart of the home, designed for both everyday living and effortless entertaining. The kitchen is fully equipped with a six burner Wolf gas range, second Wolf oven, Miele dishwasher, Sub Zero refrigerator and freezer, wine cooler, beverage drawers, marble island, and double sinks. Beyond the main residence, the estate continues to impress. A separate antique guest house with full kitchen, 3 bedroom and 1-1/2 bath provides ideal accommodations for extended family or guests. The heated gunite pool and pool house, added in 1991, offer a true retreat setting, complete with a party room, kitchen, bedroom, bath, and sauna for a resort like experience. A rare opportunity to own a private New Canaan estate with exceptional grounds, flexibility of living, and proximity to town.