New Canaan Real Estate

Welcome to New Canaan, Connecticut—a picturesque town nestled in the heart of Fairfield County, where charm meets sophistication. Known for its stunning landscapes and vibrant community, New Canaan offers a unique blend of suburban tranquility and urban convenience, making it an ideal place to call home.

With a rich history dating back to the 18th century, New Canaan boasts a delightful mix of historic architecture and modern amenities. The town is renowned for its beautifully preserved Colonial and Victorian homes, alongside contemporary designs that reflect the area’s commitment to innovation and style. Stroll through the tree-lined streets, and you’ll discover a thriving downtown area filled with boutique shops, gourmet restaurants, and inviting cafes, perfect for a leisurely afternoon.

Nature enthusiasts will appreciate the town’s abundance of parks and recreational spaces. Waveny Park, with its expansive grounds and picturesque pond, is a favorite spot for families and outdoor lovers alike. For those who enjoy hiking, the nearby nature preserves offer scenic trails that showcase the area’s natural beauty throughout the seasons.

Education is a cornerstone of New Canaan, with highly-rated schools that prioritize academic excellence and a well-rounded experience for students. The community is also known for its active arts scene, featuring galleries, theater productions, and cultural events that engage residents of all ages.

Whether you're drawn to New Canaan for its serene lifestyle, strong sense of community, or exceptional quality of life, this charming town is sure to capture your heart. Come and discover the magic of New Canaan, where every day feels like a retreat!

Newest Listings in New Canaan

$6,295,000

5 Beds ⋅ 6 Baths ⋅ 24217097 MLS

Hidden away at the end of a coveted West Side cul-de-sac, 48 Driftway Lane is a private estate tucked among the winding back roads of New Canaan. Perched atop 1.62 beautifully landscaped acres and surrounded by nature, the setting offers a rare sense of peace and privacy, yet remains just minutes from downtown New Canaan and approximately one hour from New York City. Newly constructed from the ground up in 2017 and offering over 10,000 square feet of thoughtfully curated living space, the home unfolds through a series of light-filled rooms where architectural detail, craftsmanship, and connection take center stage. A grand central foyer showcases a statement staircase framed by glass railings, creating a stunning focal point from the moment you enter. At the heart of the home, a sunlit gathering space serves as the natural connection point between the designer kitchen, soaring two-story family room, and outdoor living spaces beyond. Anchored by a stunning 10-foot quartzite waterfall island and matching custom quartzite hood, the kitchen balances beauty and function with Thermador appliances, Sub-Zero refrigeration and wine storage, custom cabinetry, and a walk-in pantry. The dramatic family room draws the eye upward with soaring ceilings, extensive architectural detailing, automated Lutron shades, and walls of windows that flood the space with natural light.

48 Driftway Ln, New Canaan

$2,895,000

4 Beds ⋅ 5 Baths ⋅ 24212560 MLS

Fabulous in-town location on a charming cul-de-sac, with sidewalks to downtown New Canaan, Mead Park, South School, Saxe and NCHS! This beautifully appointed home impresses with its scale, high ceilings and exceptional millwork, offering over 6,000 square feet across four finished levels, with 5 generous bedrooms and 4.5 baths. The gorgeous kitchen opens to the family room, and the elegant dining room flows into the sunroom and out to the updated deck overlooking the fully fenced backyard, just steps from the Bristow Bird Sanctuary. The finished walkout lower level features 9-foot ceilings, an open layout, a full bath and a movie room. The light-filled third floor offers flexible space for a gym, playroom and office. Public water and sewer. A rare combination of scale, craftsmanship and convenience in the heart of New Canaan!

7 Park Ln, New Canaan

$1,295,000

2 Beds ⋅ 3 Baths ⋅ 24213922 MLS

Charming Cape Cod Retreat Tucked away on six secluded acres of lush woods with a picturesque pond, this delightful home offers the perfect blend of privacy and convenience. Located on prestigious Smith Ridge Road in New Canaan, you're just minutes from the Village, Irwin Park, Waveny Park, and the Merritt Parkway. Enjoy serene strolls along a scenic path bordered by historic stone walls that lead to your very own pond - a perfect escape from the everyday. This delightful home features two spacious bedrooms, three full baths, a home office or study, a cozy family room, a welcoming living room, and a bright eat-in kitchen. An attached garage, ample attic and storage space provide practical living, while a large back patio invites outdoor entertaining and special moments with friends and family. Live the exceptional New Canaan lifestyle, known for its vibrant community and top-rated schools. Lots of possibilities are here for you to make this home your own and really enjoy the New Canaan lifestyle or build your own dream home in this peaceful, private setting.

792 Smith Ridge Rd, New Canaan

$8,740,000

7 Beds ⋅ 10 Baths ⋅ 24214442 MLS

A private world of its own. Newly built and set behind a gated entrance on 2.25 landscaped acres, this Scandinavian-inspired contemporary estate pairs thoughtful architecture and exceptional craftsmanship with custom-stained Accoya siding, a pool and spa, attached pool house and full guest house-all remarkably close to the heart of New Canaan. Inside, generous rooms, seven fireplaces and an elevator set the stage for interiors rich in detail. Limewashed walls, designer lighting, custom millwork and distinctive architectural elements give each room its own personality, while natural light and views of the grounds are a constant. Control4 home automation, whole-home audio and California Closets add modern convenience. The primary suite lives like a five-star hotel-the kind of retreat you may not want to leave. Downstairs, the "club level" is anything but a typical basement, anchored by a substantial bar with room for cocktails, games and movie nights. Outside, the pool and spa are joined by an attached pool house with indoor grill, while the fully equipped guest house gives family and friends their own private escape. Landscape lighting transforms the grounds after dark. 259 Frogtown Road is designed to be enjoyed-every bit as fun as it is impressive.

259 Frogtown Rd, New Canaan

$4,295,000

6 Beds ⋅ 8 Baths ⋅ 24212180 MLS

Masterfully reimagined in 2026 through a complete renovation and expansion by GreenDay Co., this 6,529SF modern estate spans 2.43 scenic acres, incorporating refined architecture in an extraordinary natural sanctuary. Historic stone walls, walking trails, mature specimen plantings and a tranquil pond frame the private grounds once home to George Valchar, author of the book "My Connecticut Garden." Inside, an organic-modern aesthetic unfolds with wide-plank white oak flooring, bespoke limewash finishes, seamless flush baseboards and expansive glass windows filling the interior with natural light. The chef's kitchen features custom white oak millwork, Dolce Vita stone surfaces, a 60-inch Wolf range, Sub-Zero refrigeration, Miele coffee system and a built-in breakfast banquette. A well-appointed butler's pantry, formal living and dining rooms and dedicated executive office complete the main level. Upstairs, the vaulted primary retreat boasts a dual-sided gas fireplace, sitting room, two walk-in closets and a spa-inspired bath finished in Taj Mahal stone. Four additional upper en-suite bedrooms feature radiant-heated baths, joined by a bespoke laundry room. The finished lower level includes a 6th bedroom, full bath and versatile gym/recreation space. Future elevator potential plus attached pool cabana with grill kitchen and full bath features accordion-style glass doors opening to a bluestone terrace, heated gunite pool and integrated spa for seamless indoor-outdoor entertaining.

311 S Bald Hill Rd, New Canaan

$9,250,000

7 Beds ⋅ 8 Baths ⋅ 24213848 MLS

Hidden behind gates and surrounded by 5.5 acres of pristine, rolling lawns, this extraordinary stone manor estate is a masterclass in old-world craftsmanship and cutting-edge modern innovation. Anchored by a separately deeded 2 acre lot with a guest house, the property presents rare flexibility and long-term value, perfectly suited for multi-generational living, guests, or future expansion. Originally constructed in 1927, the residence has been comprehensively reimagined and renovated from the inside out, preserving its architectural integrity while delivering a fully modernized, high-tech smart home experience. With all new systems, infrastructure, and finishes including new HVAC, electrical, plumbing, septic, irrigation, generator, propane tank, fencing, landscaping and all new mechanicals offering the confidence of new construction wrapped in timeless stone. Inside, over 8,500 square feet of refined living space unfolds with remarkable craftsmanship. Radiant heated floors span the first level, complemented by hand-selected reclaimed pumpkin wood, and museum-quality lighting throughout. The heart of the home is a striking new kitchen with soaring ceilings, custom concrete countertops, a bespoke island, and hand-selected bleu chinois tilework that adds depth and character throughout the first floor. Designed to entertain and inspire, the home also features an 800+ bottle wine cellar, a private fitness and training studio, and a beautifully appointed home office/library

78 & 92 Pastures Ln, New Canaan

$3,195,000

5 Beds ⋅ 6 Baths ⋅ 24213150 MLS

Set on over two private acres in one of New Canaan's most coveted neighborhoods, this elegant center hall Colonial, designed by renowned architect Dinyar Wadia, offers timeless architecture, gracious living spaces, and spectacular grounds. A circular driveway framed by stone pillars creates an impressive arrival, while a picturesque pond with fountain, charming footbridge, and rolling grassy knoll provides a breathtaking backdrop. The grand entry foyer offers captivating views through the French doors of the formal dining room to the spectacular fountain and shimmering pond beyond. An elegant living room with fireplace leads to a wet bar and magnificent oversized library, featuring custom built-ins, a marble fireplace, ample space for a grand piano, and walls of French doors opening to an expansive deck spanning the rear of the home. The spacious kitchen, also featuring French doors to the outdoors, flows into a welcoming family room with fireplace. Upstairs, the luxurious primary suite overlooks the serene grounds and features a charming window seat, spa-like bath with soaking tub, and generous walk-in closet. Three additional bedrooms, including two en-suites, complete the second floor. An expansive bonus room with lounge area and full bath offers exceptional flexibility as a playroom, guest retreat, or au pair suite. Additional highlights include a three-car garage, exceptional privacy, and beautifully landscaped grounds. Ideally located just minutes from downtown

67 W Hills Rd, New Canaan

$880,000

3 Beds ⋅ 1 Baths ⋅ 24211841 MLS

Opportunity knocks in New Canaan! Set on .33 acres in a convenient location close to the heart of town, 38 Urban Street offers an exciting opportunity for a buyer with vision. This three-bedroom ranch is ready for its next chapter and will require significant updating, but the possibilities are well worth exploring. For a first-time buyer willing to roll up their sleeves, this could be a chance to enter the New Canaan market, renovate over time, and create a home of their own. For those with a bigger vision, consider partnering with a builder or architect to explore renovation, expansion or redevelopment possibilities, subject to town approvals. The existing home features one-level living, a full unfinished basement and basement garage, all on a .33-acre parcel. The location adds tremendous appeal, with New Canaan's vibrant village, restaurants, shops and Metro-North train station nearby. Bring your contractor, your imagination and your vision. 38 Urban Street is ready for someone to see the possibilities and make it their own.

38 Urban St, New Canaan

$6,200,000

6 Beds ⋅ 5 Baths ⋅ 24209323 MLS

Set high above West Road on nearly five sunlit acres, the Leuthold House embraces south and west light and looks out over its own spring-fed pond from every room. Allan Gelbin, the Frank Lloyd Wright apprentice who supervised the building of Tirranna, designed it in 1966 with an unlimited budget and considered it his finest work. Offered for the first time in 29 years. A long curve of glass, white plaster and mahogany follows the land beneath deep overhangs and two planted green roofs. Life flows easily inside and out. The generous living room, with clerestory windows, fireplace and wet bar, opens through walls of glass to the terrace and a pool that traces the curve of the house. The dining room opens to the kitchen and its curved breakfast nook, or closes off for formal evenings. The first-floor primary suite spans its own wing with dressing room, two mahogany closets, spa bath and a private terrace with the best view in the house. Upstairs, four bedrooms and three baths open to a roof terrace. The office hides its files behind a disappearing mahogany wall and steps out to a private garden. Gelbin's teak and mahogany millwork runs throughout. A covered breezeway connects the private guest house with bedroom, bath, kitchenette and living area. 150 specimen trees, gardens and landscape lighting. Restored by Hobbs Inc. and JMK Architects with geothermal radiant heat and cooling. Cover of Connecticut Cottages & Gardens. Architecturally important and completely livable.

631 West Rd, New Canaan

$1,600,000

6 Beds ⋅ 5 Baths ⋅ 24203385 MLS

Opportunity knocks for investors and homebuyers with this meticulously updated and maintained side-by-side multifamily duplex, offering comfort, convenience, and strong investment potential. Built in 1986, the property includes two spacious units, each with a private entrance. Unit 164 offers 4 bedrooms 2 .5 bathrooms, finished lower and private deck. Unit 166 offers 2 bedrooms and 1.5 bathrooms, finished lower level and private deck. Ideal for investors or owner-occupants, driveway parking, in-unit washer and dryer, hardwood floors and updated kitchen and bathrooms. Whether you want to generate rental income or live in one unit while renting the other, this turnkey duplex is a rare find in an unbeatable location.

164 New Norwalk Rd, New Canaan

$3,695,000

6 Beds ⋅ 8 Baths ⋅ 24203727 MLS

Gracious colonial set on 3.74 private acres along a quiet west-side cul-de-sac. This cherished estate setting offers an exceptional blend of privacy, recreation, and convenience, just two miles from town and the train. The private grounds feature a Glengate Gunite pool, cabana with bath, and a barn with stables where the owners once kept horses for riding on nearby Land Trust trails. Offered for the first time in more than 50 years, this center-hall Colonial features six bedrooms, five full and three half baths, with 6,300 square feet of living space, and an additional 800 square feet of finished lower-level space. Thoughtfully renovated and expanded by Judith Larsen designs in 2005, the residence includes a beautifully appointed kitchen, an open family room with vaulted ceilings, lovely breakfast room overlooking grounds and a private in-law suite with its own entrance . Other features are 4 car garage, full house generator, pond views and driveway alert. Beautifully proportioned interiors and multiple gathering spaces make the home equally suited to comfortable everyday living and gracious entertaining. French doors spanning the rear of the residence open directly to the grounds, creating a seamless connection among the home, pool, cabana, and expansive property. A truly rare and treasured offering in one of New Canaan's most desirable west-side settings.

34 Sherwood Ln, New Canaan

$2,975,000

3 Beds ⋅ 4 Baths ⋅ 24208523 MLS

An elegant Regency-style residence with dramatic architectural presence is positioned in a premier location just moments from the village. Inside, ten-foot ceilings and Palladian windows flood the home with natural light. From the barrel-vaulted living room-a true Grand Salon-to the striking onyx-floored dining room, the interior spaces flow effortlessly to an expansive terrace, creating an unforgettable setting for both grand entertaining and quiet family relaxation. Offering a rare opportunity for luxurious, SINGLE-LEVEL living, the home seamlessly pairs grand scale with absolute privacy. The thoughtfully designed floor plan features a chef's kitchen, a sun-drenched breakfast room, a recreation/playroom, three en-suite bedrooms, and an elegant powder room. Outside, 1.25 acres of sweeping private lawns surround an impressively sized swimming pool, offering a private oasis. This exceptional residence is located in New Canaan, widely considered the most beautifully preserved New England town within one hour of New York City. Renowned for its unique design, the town's vibrant boutiques, fine dining, outstanding schools, and services are clustered in one charming, walkable center, with the residential community radiating outward in quiet, leafy tranquility.

321 Oenoke Rdg, New Canaan

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New Canaan Real Estate

Newest Listings in New Canaan

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