5-Bedroom Homes for Sale in New Canaan, CT

Set on over five private acres along New Canaan's coveted Oenoke Ridge, this extraordinary estate is a reimagined 1890s cow barn masterfully transformed by the Hobbs family with architects Joeb Moore and Louise Brooks. Blending agrarian charm with refined modern design, the residence honors its heritage while offering sophisticated comfort. A tree-lined drive and landscape lighting set a

Danielle Scialpi-Malloy Serhant Connecticut, LLC

Tucked at the end of a long, sweeping driveway in one of New Canaan's most coveted enclaves, this stately residence is a masterclass in timeless design and exceptional craftsmanship. Created for both elevated entertaining and everyday comfort, the home unfolds with sophisticated ease-from the grand front entry to the beautifully curated interiors. Every space is thoughtfully scaled and

Rita Kirby William Pitt Sotheby's Int'l

A stunning newer construction home in the most sought after location in town, 183 Hemlock Hill represents the classic Connecticut aesthetic fused with every modern amenity. This property promises an unparalleled living experience with its over 12,000 square feet of artfully designed space, set on over two acres just minutes from downtown New Canaan. Step inside and be instantly captivated by the

Christine Saxe Compass Connecticut, LLC

UNDERSTATED GRANDEUR. UNFORGETTABLE LIVING. At the end of a quiet New Canaan cul-de-sac stands a rare blend of timeless elegance and modern livability. Architect-designed and set amidst landscape architect-crafted gardens, this stone and shingle estate is grand yet understated with every inch reflecting thoughtful design & refined materials. The gracious foyer leads to a sunlit living room,

Rita Kirby William Pitt Sotheby's Int'l

Timeless, magical and serene, this exceptionally elegant and beautifully appointed country estate is perfection! Driving through the gated entry, you are immediately struck by the harmonious beauty of the 4.5 professionally landscaped acres and gracious stone and shingle style residence with handsome architectural details. With amazing natural light and exquisite millwork, each well proportioned

Mary Higgins Brown Harris Stevens

Stylish, sophisticated and fun, this stunning 10,000 SF westside country estate borders two acres of land trust for total privacy, and is conveniently located close to town and schools. Extensive and impeccable renovations in 2023 with exquisite details and millwork, superior quality craftsmanship, luxurious amenities, smart home technology, designer light fixtures, new mechanicals, new cedar

Mary Higgins Brown Harris Stevens

Step into a world of elegance and history at Orchard Ridge, an extraordinary estate with an illustrious past. This magnificent property has been home to notable figures such as Faith Hill & Tim McGraw during the filming of Stepford Wives, GE CEO, Jack Welch, and the philanthropic Dunning family, known for their contributions to NC's Dunning Field/Stadium. Property Highlights: 6.6 acres of

Hannelore Kaplan William Raveis Real Estate

NEW CONSTRUCTION To Be Built!! Enjoy modern living with an open floor plan in this stunning 5 Bedroom, 6 & 1/2 bath custom home designed by the renowned CAH Architects. Constructed by HOBI award winning builder with 35+ years of experience, the team is dedicated to building long-term relationships with their clients through creativity, attention to detail, budget oversight & timeliness. The home

Mitchell Moore Brown Harris Stevens

NEW CONSTRUCTION To Be Built!! Enjoy modern living with an open floor plan in this stunning 5 Bedroom, 4/2 bath custom home designed by the renowned CAH Architects. Constructed by HOBI award winning builder with 35+ years of experience, the team is dedicated to building long-term relationships with their clients through creativity, attention to detail, budget oversight & timeliness. The home

Mitchell Moore Brown Harris Stevens

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

Susan Morelli Coldwell Banker Realty

Discover a stunning modern sanctuary nestled privately on 2 acres, with 5 bedrooms and 4.5 baths. Floor-to-ceiling glass windows invite nature indoors, while the spacious backyard features a covered terrace with fireplace, dining & seating entertaining patios, an outdoor grill, outdoor wood fireplace and TV. The spacious chef's kitchen with island and breakfast room is a show stopper and leads to

Hannelore Kaplan William Raveis Real Estate

Nestled on the highly desirable Adams Lane, this stunning 5-bedroom, 4.5-bathroom Cape Cod home boasts over 5,500 square feet of thoughtfully designed living space with floor-to-ceiling windows throughout which embraces the 2 sprawling acres. The gourmet kitchen features a vaulted & paneled ceiling, marble countertops, top-of-the-line appliances, a spacious walk-in pantry, and a central

Jaime Sneddon William Pitt Sotheby's Int'l

Elegant 5-Bedroom Estate on 2.57 Acres at the End of a Cul-de-Sac This exceptional 5-bed, 5.5-bath estate offers over 5,400 sq ft of above-grade living space on a professionally landscaped 2.57-acre lot in a private cul-de-sac. The main level features a spacious primary suite, a home office with fireplace, a vaulted great room filled with natural light, and a beautifully renovated kitchen with

Roslyn Reed Houlihan Lawrence

Nestled on a private cul-de-sac in a pristine neighborhood, this like-new renovated 5-bedroom, 5.5-bathroom residence offers polished luxury and modern convenience just steps from schools and Waveny Park. The parking courtyard leads to a glass enclosed entry with formal living and dining rooms at either end. The white custom kitchen with quartz countertops and new high- end appliances, has a

Leslie Razook William Pitt Sotheby's Int'l

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

Kelly Defrancesco William Raveis Real Estate

Crafted from mahogany, steel and stucco with exterior design by renowned Bassam and Fellowes, this striking contemporary is sited high on Ponus Ridge. The light filled interior features custom designed walls of glass that open to lovely courtyards. Throughout you'll appreciate the attention to detail and high end finishes. All 5 bedrooms, including 2 master suites, are on the main level. The

Kelly Kraus Houlihan Lawrence

Nestled at the end of a private lane and set on 4.4 beautifully landscaped acres, this stunning brick colonial-crafted by award-winning builder Kaali-Nagy-offers nearly 7,000 square feet of luxurious living space. A dramatic three-story entryway fills the home with natural light, leading into a formal living room with a fireplace and French doors. A richly paneled office tucked just behind the

Melissa Rwambuya William Raveis Real Estate

Discover timeless elegance in this beautifully expanded and meticulously renovated Center Hall Colonial, set on two private acres abutting Audubon Society land. Nestled on a coveted cul-de-sac on a private lane in the West School district, this sophisticated home combines classic charm with modern updates and a superb location close to town. Featuring 5 spacious bedrooms and 3.5 well-appointed

Jaime Sneddon William Pitt Sotheby's Int'l

Modern Elegance Meets Timeless Charm in Prime West Side Location. Welcome to the one you've been waiting for-where location, lifestyle, and luxury converge. Perfectly situated on 2 lush acres in a quiet neighborhood minutes from New Canaan village, this completely reimagined five-bedroom, four and a half bath home is the epitome of turnkey sophistication.Property Highlights include:The new

Hannelore Kaplan William Raveis Real Estate

Gracious and Private Estate with Timeless Finishes..... Custom built in 2005 for the current owners, sited high on a private 1.16-acre lot, this exceptional residence blends classic New England charm with modern comfort. Tucked away off the road and constructed with clapboard and stone, the home offers both privacy and presence. A rare four-car garage adds convenience and distinction. Step

Janis Hennessy William Raveis Real Estate

This exquisite 7 bedroom & 11 bath colonial residence & compound set on 4.78 acres offers old world aesthetics with modern artistry. The craftsmanship of the millwork, finishes and features is unparalleled including reclaimed oak flooring imported from France and Hope's custom designed steel windows and doors. The harmonious transition between interior and outdoors is facilitated by numerous

Jennifer Crowley Douglas Elliman of Connecticut

Orchard's End, built in 1929 designed by New York architect William B. Tubby, his outstanding designs include Waveny House in New Canaan, Dunnellen Hall in Greenwich and the William H. Childs House in Brooklyn. Beginning in 2014, the current owners retained world renowned architect Dinyar Wadia to embark on a 3-year 6 million dollar renovation perfecting the already expansive 10,000 square foot

Danielle Scialpi-Malloy Serhant Connecticut, LLC

Showcasing the unparalleled 637 Valley Road estate, a majestic stone Georgian Colonial that offers an enchanting lifestyle along the tranquil banks of the Silvermine River. Spanning over 7.04 acres of idyllic park-like grounds, this 12,000 square foot masterpiece with a charming guest cottage is a treasure not to be missed. The estate boasts an expansive chef's kitchen, a stately home library,

JoAnne Fisher William Pitt Sotheby's Int'l

Welcome to this exquisite stone and shingle home, an extraordinary masterpiece built in the timeless English Cotswold tradition. Updated in 1999 and again in the early 2000's, this impeccably designed home showcases unparalleled craftsmanship, and captivates with its attention to every detail, offering a truly custom living experience. As you step inside, you'll be greeted by the allure of

Melissa Engel Douglas Elliman of Connecticut

Nestled in an exceptional location close to town, 181 Lambert Rd offers an unparalleled living experience. Architecturally enhanced, this estate exudes timeless elegance while embracing modern luxury. Built like a fortress & with the highest standards, it is designed to entertain on a grand scale. A two-story foyer welcomes you with front-to-back views of the meticulously manicured grounds.

Paola Carey Houlihan Lawrence

Welcome to Pemberly Hill, a truly exceptional home of unparalleled grandeur and sophistication. Boasting 8 bedrooms on 4 acres of pristine grounds on desirable Brushy Ridge, this magnificent property is a true masterpiece. This classic home has been thoughtfully designed to the highest standards, seamlessly blending its rich history with modern luxury. The result is an extraordinary residence

Michele Murray-Sloan Houlihan Lawrence

Welcome to Extown Farm, a stunning 17.5-acre estate that once served as New Canaan's historic farm. This rare property offers 3 separate residences, making it perfect for discerned buyers seeking a private compound. At the heart of the estate is the crown jewel: a meticulously restored 7,000 sqft farmhouse that masterfully combines modern luxury with timeless charm. This whole house renovation,

Chau Ngo Compass Connecticut, LLC

Exquisite, Stylish & Exceptional! Set on two private acres in a picturesque west-side cul-de-sac just moments from town, this stunning home offers an unparalleled blend of sophistication & comfort. Thoughtfully designed & beautifully built, it features three levels of impeccably finished living space with an open & inviting layout. The generous living room with fireplace creates a warm &

Bettina Hegel Brown Harris Stevens

Welcome to Le Beau Chateau, a grand French-style manor house originally built in 1937 on a 52 acre property restored and reimagined by Reed & Delphine Krakoff to perfection. Boasting pedigree, provenance and stunning design, this timeless and priceless estate (formerly owned by copper heiress Huguette Clark) has been magically transformed with a deep respect for its history, and a seamless

Robert Johnson Brown Harris Stevens CT, LLC

119 Proprietors Crossing is a breathtaking estate by architect James E. Gearity. Set on four acres, this fully restored six-bedroom home blends timeless elegance with modern function. A private drive and grand fountain lead you in to a soaring foyer with a sweeping staircase beneath a dramatic Baccarat chandelier. The parlor, with one of seven fireplaces, flows to a serene terrace. The Blue Room

Ashlei De Souza Serhant Connecticut, LLC

The beloved 1925 Elmstone Estate situated on over 4 acres in the heart of Ferris Hill has been lovingly restored w/ high-end finishes that blend original charm and modern-day luxury. A gated drive leads to a spectacular iconic stone home anchored by a breathtaking historic elm tree. A welcoming Dutch door leads to the expansive foyer. A second staircase leads to the masterfully designed custom

Marsha Charles Coldwell Banker Realty

Drive through the electronic iron gates to a breathtaking 16,000+ SF, 3-story Iconic Chateau of handcrafted brick and imported French slate capped roof conveying a sense of permanence, substance & Old World quality reminiscent of grand European homes. On 6+ acres, this refined style home is met inside w/a balanced mix of classic luxury and relaxed modern-day conveniences & furnishings accentuated

ileana Barns William Raveis Real Estate

Stunning proposed new transitional home nestled on 2.78 acres in private nature setting with reservoir views. This exquisite home will be stylishly designed with high end finishes and gracious open living spacious. Additional 2000+sqft can be finished in lower level. Plans and specifications can be customized to your specific needs. Pool site available.

Bettina Hegel Brown Harris Stevens

Stunning new proposed Colonial Farmhouse sited on just over 2 acres on corner of private west side cul de sac close to town. This lovely home will feature 3 stylishly finished floors of modern and sophisticated high end finishes and gracious open living spaces. Additional 2000+ sqft can be finished in lower level. Plans and specifications can be customized to your specific needs. Pool site

Bettina Hegel Brown Harris Stevens

Stunning New Construction with Scenic Views Near Town Center. Be captivated by this state-of-the-art new construction, just weeks from completion. Perched on a beautifully landscaped one-acre lot with sweeping views of God's Acre steeples, this 6,500 sq ft residence offers the perfect blend of modern design, luxury finishes, and prime location. Designed with light-filled, open-concept living in

Hannelore Kaplan William Raveis Real Estate

The Ultimate Compound! Exceptional new construction by custom home builder, Woodcrest Homes. Ultra-Prime West Road Location on 6.5 flat & dry private acres with room for a Pool, Pool House, Sports Court and Guest House (with special permit application). Seven ensuite bedrooms, transitional style throughout with beautiful finishes & clean lines. Four fireplaces with a wonderful flow & generously

Jaime Sneddon William Pitt Sotheby's Int'l

Luxury New Construction in the Heart of New Canaan **Professional Photos Coming Soon** Experience the finest in modern living with this exceptional new home by Kaeser Custom Homes, renowned for quality craftsmanship and timeless design. Ideally situated near Mead Memorial Park and Bristow Bird Sanctuary, this elegant residence offers the perfect blend of nature, convenience, and luxury-with

Jared Kuehner William Pitt Sotheby's Int'l

Originally constructed in 1937 by Philadelphia architect Julian A. Fay, this 10,000+ square-foot Georgian Colonial has been meticulously restored, renovated, and expanded by its current owners.Renowned architect Louise Brooks skillfully preserved the home's historic charm while seamlessly integrating contemporary living spaces to meet today's lifestyle demands.Situated at the end

Ashley Dineen Compass Connecticut, LLC