New Canaan Real Estate

Welcome to New Canaan, Connecticut – a charming town nestled in the heart of Fairfield County. Renowned for its picturesque landscapes and vibrant community, New Canaan offers a unique blend of suburban tranquility and urban convenience. With its tree-lined streets, historic architecture, and a thriving downtown area, this town is a hidden gem that captures the essence of New England living.

New Canaan boasts a rich history dating back to the 1700s, evident in its beautifully preserved colonial homes and landmarks. The town is home to a diverse array of cultural attractions, including the renowned New Canaan Nature Center, which offers educational programs and scenic trails for outdoor enthusiasts. Art lovers will appreciate the Philip Johnson Glass House, a masterpiece of modern architecture that draws visitors from around the globe.

Families are drawn to New Canaan for its top-rated schools and close-knit community atmosphere. The town’s commitment to education is evident in its exceptional public and private schools, providing children with a solid foundation for their future. The local parks, playgrounds, and recreational facilities further enhance the family-friendly environment, making it an ideal place to raise children.

In addition to its natural beauty and community spirit, New Canaan offers a vibrant shopping and dining scene. From boutique shops to gourmet restaurants, residents enjoy a variety of options to explore. Whether you’re sipping coffee at a local café or strolling through the charming downtown, New Canaan exudes a warm and welcoming charm that makes it feel like home.

Discover the allure of New Canaan, where every corner tells a story, and the community embraces a lifestyle of comfort and connection. Your dream home awaits in this enchanting town!

Newest Listings in New Canaan

$875,000

ACTIVE Status ⋅ 24206578 MLS

Here is a wonderful opportunity to purchase a .24 acre parcel on Weed Street and build the home you have been dreaming of. Enjoy a lovely yard and an exceptionally convenient location close to everything New Canaan has to offer, including top rated schools, Waveny Park, Metro-North train service to NYC, outstanding restaurants, boutique shopping, and the vibrant village center.

127 Weed St, New Canaan

$2,995,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24206664 MLS

Experience the pinnacle of in-town living in this meticulously reimagined New Canaan residence. Situated in the heart of the village, this home has undergone a complete rebuild and expansion, resulting in a stunning transformation that mirrors the quality of new construction. Spanning three finished floors, the interior offers five bedrooms and 4.5 luxurious baths. The open light filled floor plan was thoughtfully designed to balance modern practical functionality with exquisite design aesthetic. Outside, the property boasts a rare, large backyard and deck-a private oasis perfect for relaxation or play. Enjoy the ultimate convenience of "walk-to-everything" capability, with a back gate to sidewalk access leading you directly to the schools, Y, Waveny Park with town pool, local shops, world-class dining, library, and metro north express train to NYC, This turn-key beauty offers the perfect blend of sophisticated design and an unbeatable location.

16 Grace St, New Canaan

$4,999,999

6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24206656 MLS

THIS IS THE ONE YOU'VE BEEN WAITING FOR! Under constuction very close to completion. Brand new construction opportunity by highly regarded Lecher Development, on a prime, quiet in-town cul-de-sac. This exceptional luxury home offers 8000 + SF of high quality finishes, light-filled, living space across four finished levels. Highlights include: Gourmet Kitchen: A state-of-the-art kitchen featuring a large center island, premium stainless steel appliances, and an open layout that flows seamlessly into the family room with a fireplace and French doors leading to a covered porch. Flexible Main-Level Living: The first floor includes a private main floor space that can serve as a home office or sixth bedroom, complete with a full bath. Finished Third Floor: Ideal for a second office, playroom, guest suite, or au pair quarters. Spacious Lower Level: Featuring 10-foot ceilings, full bath, plenty of options to crate the perfect gym, media room, playroom, or additional recreation space. Generous Ceiling Heights: 9-foot ceilings on the main and second floors enhance the home's open, airy feel. Additional amenities include a 24-kW generator, five-zone heating and cooling, town water and gas. Set on a level property with a designated pool site, this home combines luxury, comfort, and customization in an unbeatable location. Don't miss the opportunity to make this exceptional property your dream home

19 Orchard Ln, New Canaan

$2,395,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205042 MLS

Welcome to 94 Field Crest Road, where turnkey living meets an exceptional resort-style lifestyle. Tucked away on a quiet New Canaan cul-de-sac just minutes from town, top-rated schools, Waveny Park and the YMCA, this beautifully renovated home offers the rare combination of privacy, convenience and effortless luxury. Fresh, sophisticated interiors are completely move-in ready. Complete w beautifully updated kitchen and bathrooms and thoughtfully designed living spaces, ideal for both everyday living and entertaining. The spacious primary suite features a large walk-in closet and en-suite bath, while the three additional bedrooms offer fabulous natural light and generous space. The lower level and basement provide valuable bonus space with endless possibilities for a media room, home office, gym, playroom, guest or in-law space. Outside is where this property truly sets itself apart. The private backyard has been transformed into a spectacular resort-style retreat featuring a Gunite pool and spa with waterfall, an expansive putting lawn with pitching spots throughout the yard, a built-in bocce court, and a stunning custom stone outdoor kitchen and bar with tv, creating the ultimate space for poolside dining and entertaining. Whether hosting summer gatherings, relaxing poolside, practicing your short game or enjoying an evening with friends, every element has been designed to make home feel like a getaway.

94 Field Crest Rd, New Canaan

$1,595,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24206440 MLS

Charm Of A Cape With A Unique Layout That Lives Like A Split-Level. The inviting floor plan features a step-down living room and dining room, creating distinct spaces for entertaining and everyday living. Offering three bedrooms and three full baths, the spacious primary suite includes two walk-in closets and a private full bath. Additional highlights include a first-floor family room, some hardwood flooring, two fireplaces, central air conditioning, and a propane generator for added peace of mind. The finished lower level provides flexible space for a recreation room, home office, gym, or guest area. Situated on a beautiful, approximately half-acre lot on a private road, this property offers a peaceful setting while remaining conveniently close to town, shopping, restaurants, and the train station. Completing the package is an attached two-car garage and plenty of space both inside and out to enjoy. A wonderful opportunity to own a charming home in a desirable location with comfort, convenience, and versatile living spaces throughout.

21 Hampton Ln, New Canaan

$1,995,000

4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24203948 MLS

Privately set at the end of a quiet cul-de-sac, this classic Colonial offers exceptional privacy, beautifully proportioned living spaces and a one-of-a-kind detached barn on a level 2-acre lot. The 4-bedroom home features a warm, timeless floor plan designed for both everyday living and entertaining. An open foyer leads to an inviting living room with built-in bookshelves and window seating, while the cozy den is ideal for work or study. A dedicated dining room, eat-in kitchen and sun-filled breakfast nook flow seamlessly to the patio and private backyard. The family room is filled with natural light and anchored by one of two first-floor fireplaces. Upstairs, the spacious primary suite features a large bath and oversized walk-in closet, along with three additional bedrooms and a full bath. The lower level offers flexible space and future potential. The true bonus feature is the detached barn, built in 2019 with workshop and finished living space. From an entertaining space to artist's studio, home office, gardening retreat or workshop, the possibilities are endless. Together, the cul-se-sac location, private setting, traditional layout, plus barn create something truly special.

20 Gray Squirrel Dr, New Canaan

$5,895,000

6 Beds ⋅ 5 Baths ⋅ COMING SOON Status ⋅ 24196978 MLS

A truly exceptional private estate, this country compound set on more than three private acres, blends timeless character, refined design, and modern luxury. Anchored by a beautifully preserved 1932 main residence and an extraordinary 2,300-square-foot poolside entertainment barn, the property is designed for both everyday living and effortless entertaining. The main residence offers five bedrooms and three full baths, including a luxurious primary suite with spa-like bath, expansive walk-in closet, and private deck overlooking the grounds. Gracious formal living and dining rooms complement a chef's kitchen opening to the family room and breakfast area. A finished lower level provides additional living and entertaining space. The poolside barn is a destination unto itself, with a dramatic Great room, wet bar and kitchenette, private gym, home office, full bath, and outdoor shower. Expansive lawns, perennial gardens, multiple outdoor fireplaces, a spectacular swimming pool, and gracious dining veranda complete the grounds. Distinct living and entertaining spaces flow effortlessly together, creating an experience like no other.

474 Brookside Rd, New Canaan

$2,795,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204690 MLS ⋅ Richmond Mews BLDG.

This beautiful townhouse with an elevator at Richmond Mews offers an easy, low-maintenance lifestyle just a short walk from town, with views of Mead Park and thoughtful design throughout. Inside, 9+ foot ceilings and oversized windows make the home feel bright and open, with hardwood floors throughout. The double-height entry welcomes you right in. The floor plan is very flexible, allowing for a formal dining room, family room, and living room depending on your needs. The gourmet kitchen has a large center island with French doors opening to a private patio. The spacious primary suite offers bedroom views of the park paired with a large sitting room or office, plus 2 walk-in closets and ensuite bath. Two additional bedrooms and a full bath complete the upper level. The finished lower level adds valuable, versatile square footage - ideal as a home gym, playroom, or additional office space. There is ample storage throughout and an attached 2-car garage. The cedar roof was replaced in 2025. Located close to New Canaan's shops, restaurants, and train station, 30 Richmond Hill Road offers a convenient, well-designed home in a sought-after location.

30 Richmond Hill Rd, New Canaan

$1,900,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24205495 MLS

A rare opportunity in New Canaan! This impeccably maintained two-family home features a unique back-to-back configuration, giving each residence exceptional privacy, its own outdoor space, garage, central air, separate parking and utilities. The property also benefits from a New roof and ideal location close to the train, shops, restaurants and highly regarded schools. Unit A offers the space and feel of a single-family home. Updated kitchen with granite counters, stainless appliances and sliders to a private deck. Stunning living room with hardwood floors, Palladian windows, soaring ceilings, skylights and exposed brick. A separate dining room with fireplace and terrace enhance the layout. Primary bedroom features a newly renovated en-suite bath, plus 2 additional spacious bedrooms and 3 full baths total. The finished walk-out lower level includes a family room, bonus space ideal for an office or guest area, full bath and a private entrance. Unit B features a kitchen updated with stainless appliances, open-concept dining and oversized living room, newer hardwood floors, 2 spacious bedrooms, 1.5 updated baths and in-unit laundry. Private patio and large backyard add to it's appeal. Ideal for investors looking to capitalize on the income potential or an owner-occupant seeking the benefit of rental income. Live in one and generate income from the other!

115 Parade Hill Rd, New Canaan

$8,995,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24201619 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 7,000 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

$1,150,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205553 MLS

Welcome to 145 Weed Street, a meticulously maintained Colonial offering a flexible floor plan, four finished levels and a convenient location just minutes from the heart of New Canaan. Built in 1995, this 4-bedroom, 3-bath home combines spacious, light-filled living with the benefits of newer construction and thoughtfully updated mechanical systems. The dramatic living room features soaring ceilings and an abundance of natural light, creating a bright and inviting space. The kitchen offers recently upgraded stainless steel appliances, a propane range and generous cabinet storage, with direct access to a large deck ideal for dining al fresco and entertaining. The deck overlooks the fully fenced backyard, providing a private and versatile outdoor setting. Four finished levels allow the home to adapt easily to a variety of needs, including a finished lower-level recreation room. Originally designed with a three-car garage, One of the three garage bays is currently used as a mudroom and storage area, with the original garage door track and opener still in place, adding everyday convenience while retaining two garage bays. Pride of ownership is evident throughout, with significant recent improvements including a new boiler and electrical panel in 2023, two new HVAC condensers in 2022 and a repaved driveway in 2024. With its 1995 construction, refreshed major systems and south-of-town location offering convenient access for commuters while remaining just minutes from downtown NC.

145 Weed St, New Canaan

$4,395,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24205057 MLS

Custom construction meets effortless in-town living at 16 Orchard Lane, a 2019 HOBI Award winner for Best In-Town Custom Home. Built by acclaimed New Canaan builder RR Builders, the residence reflects a level of craftsmanship and consideration evident throughout, from the architectural detailing and carefully selected materials to the integrated systems and sophisticated mechanicals. A gracious entry introduces interiors defined by soaring ceilings, oversized windows and abundant natural light. Wide-plank white oak floors, custom cabinetry and substantial architectural detailing bring warmth and character, while generously scaled rooms and an easy, connected flow allow the home to feel both substantial and comfortable. At the heart of the home, the chef's kitchen features custom cabinetry, premium appliances and an oversized gathering island, opening naturally to the family room, dining area and rear porch. A generous pantry, functional back hall and extensive built-in storage bring organization and purpose to everyday living. Four finished levels provide exceptional flexibility. The primary suite features a dramatic vaulted ceiling and three exposures, complemented by a generous walk-in closet and bath with radiant heat, steam shower and soaking tub. The finished third floor offers additional airy, flexible space, while oversized windows bring unexpected natural light to the lower level, with recreation space and a dedicated gym.

16 Orchard Ln, New Canaan

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