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119 Proprietors Xing, New Canaan
$6,550,000
6 Beds ⋅ 10 Baths ⋅ 24156735 MLS
119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere. Spacious entertaining areas flow seamlessly to a tranquil terrace. The heart of the home includes a chef's kitchen that opens to a Great Room with a remarkable 35.5 foot vaulted ceiling, centered around a large quartz island with integrated audio. A formal dining room beneath another Baccarat chandelier sets the stage for memorable gatherings. The West wing hosts the primary suite, featuring a cozy retreat and a study with a hidden staircase leading to a gym and an 800-square-foot dressing room. An adjacent Junior Primary Suite has its own entrance and living area. Upstairs, four additional bedrooms include two ensuite and two with a jack-and-jill bath. The finished lower level boasts a media room, fitness center, and wine cellar. Outdoors, curated grounds offer a dining pavilion, outdoor kitchen, and a newly constructed pool and spa, with space for a tennis/pickle-ball court. Engineered for efficiency, the estate features commercial-grade systems, radiant heat, and a rare Welsh slate roof. A four-car garage and an elevator service complete this exceptional offering.

119 Proprietors Xing, New Canaan
276 Greenley Rd, New Canaan
$5,600,000
6 Beds ⋅ 7 Baths ⋅ 24141707 MLS
Nestled in one of Connecticut's most sought-after estate neighborhoods and just minutes from town, this spectacular 1939 Classic Colonial blends timeless elegance with every modern amenity. Set on nearly 5 bucolic acres of rolling lawns, perennial gardens, and mature trees, this pristine property offers unmatched privacy and beauty. The grand approach includes a stately driveway with a central fountain leading to an inviting paneled foyer. Inside, the gracious living room with fireplace and built-ins opens to a formal dining room that overlooks the magnificent grounds. The chef's kitchen, complete with eat-in area, is perfect for both everyday living and entertaining. Unique lifestyle features abound: a spacious game room with cigar ventilation ideal for cards or gatherings, a cozy wood-paneled office with extensive built-ins, and a secondary office featuring a charming circular window with a view of the sprawling front lawn. The luxurious primary suite offers a fireplace, dual walk-in closets, and a spa-inspired bath. Four additional bedrooms provide comfortable accommodations for family and guests. A modern gym and a bonus bunk room with sleeping quarters for up to eight make this home as functional as it is elegant. Outdoors, enjoy an expansive patio perfect for entertaining, a swimming pool, and a tennis/pickle ball/sport court-all surrounded by meticulously manicured landscaping that recalls a bygone era of quiet sophistication. A true Connecticut gem,

276 Greenley Rd, New Canaan
114 Adams Ln, New Canaan
$5,300,000
6 Beds ⋅ 10 Baths ⋅ 24169455 MLS
Experience timeless elegance and resort-style living in this extraordinary stone estate on 2+ spectacular acres overlooking a serene spring-fed pond with direct water access. Designed by architect Malcolm Robertson with interiors inspired by Rick Livingston Period Design, this home offers 9,369 SF of masterfully crafted living space blending architectural sophistication with modern luxury. Built in 2004, the home showcases Venetian plaster walls, cerused oak details, radiant heated stone floors, soaring ceilings, extensive custom millwork, and dramatic walls of glass framing breathtaking views of the pool, grounds, and pond. At the center of the home is a showstopping 3 story gourmet kitchen-a true culinary masterpiece-seamlessly blending architectural drama with top-tier functionality with limestone counters, oversized gathering island, and premium Miele, Wolf, Viking, and SubZero appliances. Designed for both grand entertaining and comfortable everyday living, the residence features 6 en-suite bedrooms, 8 full and 2 half baths, with spectacular first-floor primary suite with dressing rm and spa bath. Amenities incl media rm, billiard rm, sun rm, gym, professional office suite, Control4 smart home technology, surround sound, heated pool w/automatic cover, separate spa, Har-Tru tennis court, extensive landscape lighting, and beautifully manicured grounds. Rarely does a property of this caliber, privacy, and design become available just moments from town in a coveted location

114 Adams Ln, New Canaan
26 Pequot Ln, New Canaan
$5,250,000
6 Beds ⋅ 8 Baths ⋅ 170473214 MLS
THIS MAGNIFICENT ESTATE HAS BEEN FEATURED IN THE N.Y. TIMES MAGAZINE FOR ITS EXTRAORDINARY ENTRY AND CONSTRUCTION. BE IT THE OVERSIZED POOL, RARE CUSTOM ELEVATOR, SPORTS TENNIS COURT, MEDIA ROOM, HIS & HER SEPARATE BATHS, ALSO INCLUDED ARE SEVERAL PRACTICAL AND FUN AMENITIES THAT GRACE THIS ONE OF A KIND HOME. WITH PRIVACY ON ALL FOUR SIDES THIS HOME PRESENTS ONE OF THE BEST LOTS, SCHOOL SYSTEMS IN CT. STONE WALLS & SPECIMEN PLANTINGS ABOUND AND ONLY 1.8 MILES FROM POUND RIDGE N.Y. AND 4 MILES FROM THE TOWN OF NEW CANAAN CT. NEW CANAAN IS ONE OF THE SAFEST COMMUNITIES IN THE TRI STATE AREA, A MUST SEE IN THESE TIMES. THE REPLACEMENT COST OF THIS HOME IS ESTIMATED AT OVER 10 M, SO AT THIS ASKING PRICE IT IS CLEARLY A GREAT DEAL. IT CAN BE SOLD FURNISHED IF DESIRED. IN ADDITION A POOL TABLE, EXERCISE EQUIPMENT, DESK, A MAGNIFICENT CHANDELIER ARE INCLUDED. CUSTOM BUILT BY THE ONLY OWNER IT IS A MUST SEE. YOU WILL NOT BE DISAPPOINTED. ITS BEAUTIFUL MOLDINGS, VERANDA AND CLASSIC DESIGNS ARE RARE IN TODAYS BUILDING COMMUNITY. WITH THE HIGHEST QUALITY CONSTRUCTION & APPLIANCES IT WILL SERVE THE NEW OWNERS WELL.

26 Pequot Ln, New Canaan
42 Hillcrest Rd, New Canaan
$4,855,000
5 Beds ⋅ 8 Baths ⋅ 24134781 MLS
A masterpiece of modern luxury, this 8,400 sq ft estate by Arena Development has been meticulously crafted to elevate everyday living. Thoughtfully designed and majestically sited with a dynamic, light-filled layout, the home unfolds across four exquisitely finished levels, anchored by a spectacular chef's kitchen and expansive family room that form the true heart of the residence. Five beautifully appointed en suite bedrooms offer refined comfort, while the home's position on the coveted West Side places you just minutes from the transportation and village. Every detail speaks to sophistication and craftsmanship-soaring ceilings, four elegant fireplaces, graceful transitions between living spaces, and a stunning walkout lower level designed for recreation and relaxation. Outdoors, a brand-new pool and spa transform the property into a private resort, complemented by a three-car garage and serene, manicured grounds. Built to the highest standards of performance, the residence combines luxury with efficiency. Energy Star construction, a 7-zone dual-fuel heating system, and a suite of advanced smart-home technologies ensure effortless comfort in every season. High-performance insulation, intuitive smart thermostats, and integrated whole-home automation complete this exceptional offering. Refined, innovative, and beautifully executed-this is modern living at its most luxurious

42 Hillcrest Rd, New Canaan
73 Lake Wind Rd, New Canaan
$3,825,000
5 Beds ⋅ 10 Baths ⋅ 24160722 MLS
Located in the desirable Lake Wind / Ponus Ridge corridor, this custom Colonial estate offers over 9,000 square feet of living space, thoughtfully rebuilt in 2010 and designed for both scale and comfort. The home features 5 bedrooms, 7 full and 3 half baths, six fireplaces (including one outdoor), and multiple porches, with select rooms showcasing cathedral ceilings. Set on 2.74 acres, the property includes a saltwater pool and spa, pool house, expansive flagstone patio, and tennis court-creating a true estate setting with exceptional potential for outdoor living and entertaining. The interior presents with a clean, functional layout, including a recently installed boiler, while exterior amenities and select finishes offer a compelling opportunity for renovation and customization, allowing the next owner to fully realize the property's potential. A rare offering combining size, privacy, and long-term upside in one of New Canaan's premier estate areas.

73 Lake Wind Rd, New Canaan
113 Skyview Ln, New Canaan
$3,600,000
5 Beds ⋅ 6 Baths ⋅ 24127202 MLS
Just off Ponus Ridge and moments from Talmadge Hill Train Station, this exceptional Colonial home offers easy access to the Merritt and downtown amenities. Set on 1.67 acres of beautifully landscaped, gated grounds, the property boasts a newly renovated, resort-style gunite pool and spa, an oasis for outdoor living. The professionally manicured backyard is complemented by a stunning bluestone patio, complete with a dramatic fountain centerpiece, ideal for entertaining. This home welcomes you with a grand two-story foyer, leading to an open-concept Kitchen's By Deane chef's kitchen featuring high-end appliances, including dual refrigerator/freezers, a butler's pantry, and a sun-filled breakfast nook. The adjacent family room offers a cozy gas fireplace and French doors that open to a balcony overlooking the serene pool area. The second floor showcases a sophisticated primary suite with custom built-ins, a spacious walk-in closet, and an updated, spa-inspired bath complete with a heated floor and towel rack. Three additional bedrooms and two full baths provide ample family space. A private staircase leads to a bedroom suite, complete with a sitting room and full bath, ideal for an in-law or au pair suite. The lower level has 2334 addt'l finished SqFt with a gym area, a living space with a cozy fireplace, and a wine cellar. In addition, there is a 3-car garage, a full house generator and separate storage shed. This meticulously maintained estate is truly an extraordinary prope

113 Skyview Ln, New Canaan
1580 Ponus Rdg, New Canaan
$3,400,000
5 Beds ⋅ 6 Baths ⋅ 24118090 MLS
California meets New Canaan in this William Wurster inspired transitional-style masterpiece set on 2.54 private acres on New Canaan's desirable west side that's so convenient to town. This extensively renovated home has over 100 custom windows and 16 doors bringing the outside in from every room. Amazing sun-drenched living space with wonderful views from EVERYWHERE. French doors lead to expansive bluestone terraces, a beautiful gas fire pit for entertaining, meticulously manicured flower gardens, pool, spa and river. Five bedrooms, 4-car garages, au pair suite and an exceptionally designed layout make this home a sensational haven with the warmth of a colonial but so fresh!

1580 Ponus Rdg, New Canaan
39 Running Brook Ln, New Canaan
$2,885,000
6 Beds ⋅ 8 Baths ⋅ 24156338 MLS
At the end of a quiet cul-de-sac, surrounded by 2.7 acres of privacy, 39 Running Brook Lane combines gracious living with everyday convenience, moments from top schools, parks, Metro North and more. Soaring ceilings, and beautifully proportioned rooms make for inviting yet impressive everyday living and entertaining. The custom Deane kitchen anchors the home with top-tier appliances, a butler's pantry, walk-in pantry, and a sunlit circular breakfast area that flows seamlessly into the family room with fireplace. Formal living and dining rooms extend to bluestone patios, enhancing effortless indoor-outdoor entertaining. A richly paneled study, flexible first-floor guest suite or office, two powder rooms, and a well-appointed laundry room complete the main level. Upstairs, the expansive primary suite offers dual bathrooms and three custom walk-in closets, while four additional bedrooms and three full baths provide generous accommodations for family and guests. The walk-out lower level expands the lifestyle appeal with a brand-new sauna and Himalayan salt room, plus substantial space for a gym, media room, or recreation. Recent improvements include a brand-new high-efficiency boiler, freshly painted interiors and exterior and a resealed driveway. This is one you have to see to truly appreciate!

39 Running Brook Ln, New Canaan
77 Winfield Ln, New Canaan
$2,620,000
5 Beds ⋅ 5 Baths ⋅ 24138970 MLS
Located on a much sought-after cul-de-sac surrounded by estate properties, 77 Winfield Lane presents a compelling opportunity to re-envision a 4,100 square foot, 5-bedroom, 5-bath residence set on 2.88 acres of private grounds. The home's traditional architecture and balanced proportions create a strong framework for renovation, expansion, or enhancement. The property features a pool and generous outdoor space, offering privacy and flexibility for future improvements. Walkable to West School and nursery school, and offering easy access to New Canaan village, this is a rare opportunity to secure land, location, and long-term upside. Property is being sold in its present condition.

77 Winfield Ln, New Canaan
41 Lake Wind Rd, New Canaan
$2,600,000
5 Beds ⋅ 6 Baths ⋅ 24169105 MLS
Set on a beautifully scenic 2.35-acre lot on a tranquil circle near Laurel Reservoir, this exceptional property stands as the pinnacle of curb appeal, with a picturesque pond (and private island accessed by a footbridge) leading to the home's grand facade. Completely reimagined and remodeled in 1998 by distinguished architect, Carol Kurth, and renowned builder, Joseph Sisca, the home was awarded the Society of American Registered Architects' Design Award of Merit for superior achievement and professional design excellence. The gracious two-story foyer welcomes visitors into the open concept living and dining rooms. The spacious chef's kitchen, featuring an eat-in breakfast nook with panoramic windows, adjoins an inviting family room with fireplace. Privately positioned on the main level, the primary suite includes a fireplace, private deck, and large bathroom with radiant floor heating. The upper level provides four additional bedrooms; two with ensuite baths and private balconies. The expansive finished lower level adds a rec room with wet bar, gym, workshop, and wine cellar. Beautifully integrated with its natural surroundings, the property offers exceptional privacy, scenic views, and inviting indoor-outdoor living throughout the seasons. The garage is equipped with a Tesla charging station.

41 Lake Wind Rd, New Canaan
235 Hawks Hill Rd, New Canaan
$2,450,000
5 Beds ⋅ 6 Baths ⋅ 24185279 MLS
West Side Oasis Nestled on a quiet, highly desirable cul-de-sac on the West Side of New Canaan, this meticulously cared-for property offers the perfect blend of elegant living and secluded outdoor recreation. A sweeping circular driveway and an inviting covered front porch welcome you to this stunning wooded retreat. Step inside to a grand two-story foyer featuring an elegant balcony overlook. The sophisticated floor plan flows seamlessly for entertaining, highlighted by stately pillars that define the formal living and dining rooms. For those working from home or seeking a quiet retreat, the handsome library is appointed with custom cherry wood-built ins.The private backyard operates as your own personal resort. Step out onto the expansive rear deck, complete with a sunken hot tub, and take in the serene views of the heated pool and surrounding mature woods. There is a dedicated wine cellar for the discerning collector, whole-home generator for year-round peace of mind, an expansive walkout finished lower level

235 Hawks Hill Rd, New Canaan
12 Field Crest Rd, New Canaan
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 24146450 MLS
12 Field Crest Road is a bright, well-maintained Colonial offering the rare combination of walkability, convenience, and room to grow-just moments from downtown New Canaan, Metro-North, schools, and Waveny Park. The main level delivers an easy, everyday flow with a sun-filled living room and fireplace, a traditional dining room, and a renovated kitchen featuring updated appliances and crisp finishes. Just off the kitchen, a dramatic vaulted-ceiling great room is filled with natural light, creating a warm and inviting gathering space. A flexible playroom/office/den and a powder room complete the first floor. Upstairs, the primary suite offers a renovated bath and generous closet space, while three additional bedrooms share an updated hall bath. The unfinished lower level provides excellent potential for a gym, playroom, storage, or future finished living space. Outside, enjoy a level yard with deck and patio-ideal for play and entertaining-along with an attached garage, newer mechanicals, and thoughtful improvements throughout. A buried propane tank supplies gas to the generator, ensuring uninterrupted power during storms, and a gas line is already in place for future conversion or expansion (buyer to perform due diligence). A truly turnkey opportunity in a coveted in-town location where lifestyle, comfort, and convenience meet.

12 Field Crest Rd, New Canaan
496 Trinity Pass Rd, New Canaan
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 24073041 MLS
This 4 bedroom,3.5 bath tastefully renovated vintage home has an open floor plan,walls and windows with divided light and high ceilings, creating an instant sense of peace and well being. A stone hearth at the entry is surrounded by walls of bookshelves and a reading corner. The beamed living room and adjacent sun room overlook a romantic tiered garden and flat lawn. The fireplace's stone wall frames the dining space, and French doors open onto the garden patio and pergola. The warm polished wood island featuring a copper bar sink is the centerpiece of a perfect chef's kitchen. Down a private hall is the walk out first floor bedroom with full bath, walk in closet and adjacent laundry room. Upstairs an exercise/ gym space is conveniently located outside the primary suite with it's private office, high ceilings, walk in closet, and elegantly kitted bath (soaking tub, double sinks, walk in shower) Two additional generously proportioned bedrooms share a large hall bath. Convenient to charming Scott's Corners and just a few minutes to New Canaan town center, this is a special spot. Swing on the front porch, have morning coffee on the patio, wander the charming garden features, plant the enclosed garden with vegetables, flowers and herbs. Breathe. Zen living behind a stone wall on a rural street.This one is just right.

496 Trinity Pass Rd, New Canaan
349 Ponus Rdg, New Canaan
$1,550,000
3 Beds ⋅ 2 Baths ⋅ 24177673 MLS
Situated just moments from town, the train, schools, restaurants and shops, 349 Ponus Ridge offers one level living at its finest. The open floor plan consists of a formal living and dining room with stone fireplace, updated eat in kitchen with vaulted ceiling and exposed beams. The large primary suite has views of the backyard with full bathroom, walk in closet and laundry room. Two double bedrooms share a hall bath. A blue stone patio leads to the private backyard that has plenty of space for play, outdoor dining, and entertaining. Attached one car garage. Auxiliary generator adds peace of mind.

349 Ponus Rdg, New Canaan

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