New Canaan Connecticut homes for sale starting at Fifty Thousand Dollars

$25,500,000 - New Canaan, CT

104 Dans Highway New Canaan, CT - 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 infusion of bespoke finishes, quiet luxury and comfort connecting with the natural light and views beyond. Surrounded by open meadows, gentle streams and woodlands, the extraordinary property has been thoughtfully enhanced amid rolling lawns, wildflower gardens, specimen trees, a gorgeous pool and tennis court. Also includes 2 cottages; a 2 BR caretakers cottage - 1096 sq ft and an exercise pavilion 1296 sqft. This enchanting compound remains one of Fairfield County's last great private estates.

$12,400,000 - New Canaan, CT

544 Oenoke Ridge New Canaan, CT - A rare opportunity to own a legacy estate that would command over $50 million to recreate in today's market. 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 addition completed by the previous owners. Not only was the main residence improved and expanded upon a brand new 2,000 square foot 4-bedroom guest house, along with a custom designed 5,000 square foot wellness center, a custom pool with spa and new terraces transformed Orchard's End Estate into a true masterpiece. The main residence's addition includes a new kitchen, great room, outdoor courtyard, and study. Providing the inspiration for the great room was Castle Duart, located on the Isle of Mull and featured in the 1999 movie Entrapment in which Sean Connery and Catherina Zeta-Jones, playing art thieves, practice their moves for a high-tech heist. FURNISHED option available for separate pricing.

$12,400,000 - New Canaan, CT

$10,995,000 - New Canaan, CT

358 Lukes Wood Road New Canaan, CT - 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 access points, connecting the elegant indoor spaces to expansive outdoor spaces, including guest house/pool house leading out to the pool & spa w/pergola. The lower level offers versatile space with golf simulator & putting green, bar area, gym/yoga studio, wine cellar and home theatre. Renovated barn w/inlay hardwood floor & sport court is next to tennis court. Full house generator. Prop in CT & NY.

$8,995,000 - New Canaan, CT

928 West Road New Canaan, CT - 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 proportioned rooms. Glorious primary suite with stunning bath including radiant heat floors & cathedral ceiling. Paneled library, custom millwork throughout, bright chef's kitchen with adjacent breakfast room, family room with coffered ceiling, finished lower level and 3rd floor, large mudroom with radiant heat floors. Elevator to all 4 floors. Design services provided by Haley Design Company to customize this spectacular home. All photos are examples from a prior building project. Woodcrest Homes has a stellar reputation and a roster of highly satisfied clients. The lucky buyer has the ability to fully customize this property to meet their preferences. This is a dream estate with many possibilities to create your own compound on this private 6.5 acre West Road property.

$8,688,000 - New Canaan, CT

119 Proprietors Crossing New Canaan, CT - 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 offers a refined retreat, while the study, with a coffered ceiling and secret staircase, connects to the primary suite. The formal dining room glows under another Baccarat chandelier. Adjacent is the chef's kitchen, now complemented by the family kitchen in the Great Room featuring an enormous leathered quartz island. This room, with a 35.5-ft vaulted ceiling, boasts integrated high-end speakers as part of a whole-home audio system. The primary suite showcases a new 800 sq. ft. dressing room and a gorgeous two level bathroom with freestanding tub. The lower level of the home offers a media room, gym and wine grotto. The outdoor space includes a dining pavilion, outdoor kitchen, and a brand-new pool with spa. Built for luxury and efficiency, the home has commercial-grade systems, SIP walls, a Welsh slate roof, radiant heat, and 14 temperature zones for your comfort. Additional features include a four car garage and an elevator accessing all levels of the home. This newly restored gem incorporates enhanced functionality for today's buyers, built to last for gener

$8,688,000 - New Canaan, CT

119 Proprietors Crossing New Canaan, CT - Welcome to 119 Proprietors Crossing, a dramatic estate by architect James E. Gearity. Set on four acres, this restored six-bedroom home blends elegance with modern function. A grand foyer with a sweeping staircase and Baccarat chandelier leads to refined living spaces, including the immaculate Blue Room, study with a secret staircase, and great room with 35+ ft vaulted ceilings and integrated speakers. The chef's kitchen is now complemented by the Great Room's family kitchen with a enormous quartz island. The primary suite boasts a new wetroom with a freestanding tub and an 800 sq. ft. dressing room. Outdoor spaces include a new pool/spa and a dining pavilion. Built for comfort, the home offers commercial-grade systems, SIP walls, a Welsh slate roof, radiant heat, and 14 temperature zones

$7,695,000 - New Canaan, CT

1227 Ponus Ridge New Canaan, CT - 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 roof and a harmonious palette offers the perfect oasis for comfortable living, working and entertaining. Highlights include 10 ft. ceilings, 6 fireplaces, private study/office, 1st and 2nd floor family rooms, dramatic two story entry, and a new show-stopping Christopher Peacock custom kitchen and butler's pantry with furniture quality cabinetry, super sized island, major high end appliances and a sun-drenched dining area. All seven spacious ensuite bedrooms have gorgeous new bathrooms. The fabulous master suite with sitting area/fireplace has an amazing custom dressing room and extraordinary bath. Just completed lower level has a wine cellar, gym, media room, ensuite bedroom, cabana bath and is walk out to the pool area. The expansive bluestone terrace with fireplace abuts the glorious pool area with spa that is surrounded by lush landscaping and nature's beauty. This is a forever turnkey home ready to warmly welcome its new owners.

$6,195,000 - New Canaan, CT

945 Oenoke Ridge New Canaan, CT - Tucked along the coveted crest of Oenoke Ridge in New Canaan, this extraordinary country estate unfolds across five secluded acres, a masterful transformation of an 1890's cow barn that bridges agrarian heritage with refined architectural vision. Thoughtfully reimagined by the Hobbs family in collaboration with acclaimed architects Joeb Moore and Louise Brooks, the residence honors its pastoral roots while embracing a timeless, contemporary elegance.A stately approach, lined with linden trees and subtly lit by bespoke landscape lighting, sets the stage for what lies within. At the heart of the home, a soaring two-story great room stuns with a dramatic floor-to-ceiling stone fireplace, framed by original post-and-beam construction and antique pine floors.

$6,195,000 - New Canaan, CT

945 Oenoke Ridge 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 gracious tone on arrival. Inside, the dramatic two-story great room features a soaring stone fireplace, post-and-beam framing, and antique pine floors. A storybook catwalk leads to a second-floor library, while the sunlit gourmet kitchen flows into a breakfast room and formal entertaining spaces. The six-bedroom layout includes a first-floor primary suite with a sitting room ideal for a nursery or office. The walk-out lower level offers a wine cellar, playroom, bedroom, and full bath. A detached three-car garage includes a guest apartment with its own entrance, living room, bedroom, and bath-perfect for in-laws or extended stays. Outdoor living is elevated with a heated gunite pool overlooking the reservoir, a fireplace, meditation pool, and secret garden path. Designed by Kathryn Herman Design, the award-winning landscape features terraced gardens, meadows, specimen trees, and a producing apple orchard. Just minutes from town, this is a rare opportunity to own a timeless piece of New Canaan's history.

New Canaan, Connecticut listings for sale

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