New Canaan Real Estate

Welcome to New Canaan, Connecticut – a picturesque gem nestled in the heart of Fairfield County. Renowned for its stunning landscapes and vibrant community, New Canaan offers a unique blend of suburban charm and urban sophistication. With its tree-lined streets, historic architecture, and an array of local boutiques and eateries, this quaint town is a perfect haven for families, professionals, and retirees alike.

New Canaan boasts a rich history, reflected in its beautifully preserved buildings and landmarks, including the iconic Glass House designed by architect Philip Johnson. The town is also home to a thriving arts scene, with numerous galleries and cultural events that celebrate creativity and community spirit. Outdoor enthusiasts will appreciate the extensive parks and nature reserves, including Waveny Park, which offers miles of trails, sports facilities, and scenic picnic spots.

Education is a top priority in New Canaan, with highly-rated public and private schools that consistently rank among the best in the state. Families are drawn to the community not only for its excellent educational opportunities but also for its safe and welcoming environment.

Conveniently located just a short train ride from New York City, New Canaan provides residents with easy access to the bustling metropolis while maintaining the tranquility of suburban living. Whether you’re looking to explore the local farmers' market, enjoy a leisurely stroll through the charming downtown area, or connect with neighbors at community events, New Canaan is a place where you can truly feel at home. Discover the enchanting lifestyle that awaits you in this idyllic Connecticut town!

Newest Listings in New Canaan

$1,595,000

3 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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

$2,895,000

4 Beds ⋅ 4 Baths ⋅ 24204760 MLS

This stunning Mid-Century Modern home combines striking architecture, sophisticated designer finishes and exceptional indoor-outdoor living in a private setting with sweeping views and spectacular sunsets. Thoughtfully expanded and extensively rebuilt in 2015, the home features a light-filled open floor plan, walls of glass and high-quality finishes throughout. At the heart of the home, the dramatic living and dining areas feature soaring vaulted ceilings and expansive windows that frame breathtaking vistas and flood the interiors with natural light. The first-floor primary suite offers a private sanctuary with a spacious walk-in closet and dressing room. Three additional bedrooms provide generous accommodations, while the fabulous lower-level great room opens directly to the terrace and pool area and features an entertainment bar-perfect for relaxed gatherings and entertaining. Multiple outdoor living spaces take full advantage of the home's beautiful natural setting. A stunning infinity-edge pool with waterfall creates a resort-like focal point, complemented by an outdoor shower, expansive terraces and gorgeous perennial gardens. A truly special home offering privacy, dramatic views and exceptional modern living.

250 Dans Hwy, New Canaan

$1,995,000

5 Beds ⋅ 4 Baths ⋅ 24201426 MLS

Nestled at the end of a long private drive south of the Merritt Parkway, this classic Colonial offers timeless character, generous living space, and a highly convenient location. Beautifully expanded and thoughtfully updated 15 years ago, the home showcases exceptional craftsmanship, enduring quality, and solid construction described as having "great bones." The main level is rich with architectural detail - an elegant front-to-back Living Room with fireplace and exquisite custom built-in cabinetry and the Dining Room with beautiful built-in details. At the heart of the home is an expansive Kitchen featuring high-end appliances, custom built-ins, and a second fireplace in the casual dining area-an inviting space for morning coffee, relaxed meals, or entertaining. The adjacent light-filled Family Room offers beautiful views of the changing seasons and provides a comfortable extension of the main living areas. The house includes four spacious bedrooms and 2.5 baths, while a private suite above the garage adds a fifth bedroom with full bath, offering flexibility for guests, a private office or additional living space. Finished recreational space on the lower level provides room to work, play, exercise and the generous terrace creates an inviting setting for outdoor dining and entertaining. With its distinctive architecture, thoughtful layout, and quality details, the home offers an exceptional foundation for personalization, including some cosmetic updating to the exterior.

523 Brookside Rd, New Canaan

$3,895,000

5 Beds ⋅ 6 Baths ⋅ 24197589 MLS

Set on 1.5 beautifully landscaped acres along coveted Gerrish Lane, this 1948 Colonial compound pairs timeless architecture with thoughtful updates and an effortless connection between indoors and out. Mature plantings and distinctive gardens surround the residence, creating a rare sense of privacy and tranquility just minutes from town. Generous living spaces and refined details define the home throughout. The first floor offers a gracious and versatile layout, with an open family room and kitchen at the heart of the home. French doors connect the family room and living room to the surrounding grounds, creating an easy flow between indoor and outdoor living. A formal dining room provides an elegant setting for entertaining, while a step down library offers a more intimate retreat. A first floor bedroom with full bath can serve as an alternate primary suite or home office. The primary suite is a true retreat, featuring separate baths, walk-in closets, and a balcony overlooking the lawn and gardens. Above the garage, a studio with full bath and kitchenette offers flexibility as an au pair suite, playroom, office, or guest quarters. A separate 1,146 square foot cottage includes a living room, bedroom, full kitchen, and 1.5 baths, ideal for guests, extended family, or a private workspace. A charming storage shed completes the property. 38 Gerrish Lane offers a rare balance of pastoral serenity and modern day ease in one of New Canaan's

38 Gerrish Ln, New Canaan

$850,000

2 Beds ⋅ 3 Baths ⋅ 24203278 MLS ⋅ Graystone BLDG.

This charming two-bedroom, 2.5-bath condo is located just minutes from the center of town. The newly renovated kitchen is fresh, bright, and thoughtfully designed, with an easy flow into the living and dining areas. The private outdoor deck extends the living space and is an ideal spot for morning coffee or gathering with friends for dinner outside. The two bedrooms offer comfortable, private spaces, while the fully finished lower level provides flexible additional space for a family room, home office, gym, or guest area. With a full bath and laundry on this level, it adds both functionality and convenience. A detached one-car garage provides private parking and extra storage. Turnkey and ideally situated within the well-maintained Graystone Circle complex, this condo offers exceptional convenience, flexibility, and easy living just minutes from town.

68 Lakeview Ave Unit 5, New Canaan

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