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$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

$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

$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

$2,895,000
4 Beds 4 Baths ACTIVE Status 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 ACTIVE Status 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 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

$4,000,000
5 Beds 6 Baths ACTIVE Status 24178727 MLS
Welcome to a property where a collector's garden of Japanese maples, rhododendrons, and azaleas - in every shade from gold to crimson to blush pink - announces something extraordinary before you've even reached the front door. A circular drive leads to this classic New England white Colonial, set on nearly three and a half acres on prestigious Turtle Back Road, where grounds shaped with the care of a private arboretum unfold: flagstone terraces, fieldstone walls, and specimen plantings set against a canopy of mature trees. From its copper roof to its storied gardens, every element of this five-bedroom, six-bath New Canaan property feels distinctive. With nearly 5,200 square feet of living space, the home offers generous accommodations while maintaining real warmth and character. Positioned to embrace its surroundings, sun-filled interiors and tranquil views from nearly every room create a seamless connection between indoors and out. Whether entertaining on a grand scale or savoring the simple pleasures of everyday life, the property offers a rare sense of space, comfort, and retreat. Just minutes from the heart of New Canaan, this exceptional home provides easy access to downtown amenities, award-winning schools, parks, and Metro-North - while feeling worlds away from it all. Seldom does a property offer such a rare combination of privacy, beauty, and one of Fairfield County's most sought-after addresses.

248 Turtle Back Rd, New Canaan

$1,399,000
3 Beds 3 Baths ACTIVE Status 24202379 MLS Hathaway Common BLDG.
Have you ever imagined living on prestigious South Avenue and strolling into town for dinner, shopping or ice cream on a beautiful New England evening? Welcome to highly sought-after Hathaway Common, where convenience, community and a peaceful setting come together. This bright and spacious 3-bedroom, 2.5-bath home offers a wonderful floor plan with a dedicated dining area, fireplace and finished lower-level space, currently used as a home office. A private garage, central air and smart-home features add everyday ease. Enjoy private outdoor space, expansive lawns, abundant guest parking, a community pool and clubhouse, all without the worry of yard work or snow removal. Best of all is the exceptional location. Flat, walkable sidewalks connect you to New Canaan's vibrant village, award-winning restaurants, shops, library and Metro-North, as well as local schools and the YMCA. Mead Park is just moments away for tennis, pickleball, baseball and skating. A rare combination of space, tranquility and extraordinary convenience, this is New Canaan living at its best.

179 S Ave Unit 9, New Canaan

$2,349,000
4 Beds 4 Baths ACTIVE Status 24196988 MLS Down River Condominiums BLDG.
6 Down River pairs new construction with privacy and walkability - the scale of a single-family home, without the maintenance. Built in 2024 and further refined in by the developer in 2025, this 4-bedroom residence offers over 3,000 square feet across four finished levels, conceived for an effortless lock-and-leave lifestyle. The main level is open and light-filled, built for entertaining: the kitchen with custom cabinetry, high-end appliances and a large center island connects seamlessly to dining and living areas anchored by a gas fireplace and bar. Upstairs, the primary suite includes a spa-like bath and generous walk-in closet, alongside two well-proportioned bedrooms, additional baths and a laundry room on the same level. The finished third floor delivers a fourth bedroom - suited to a home office, bunk room, or playroom. What sets 6 Down River apart: Finished third floor - fourth bedroom, office, bunk room or play space. Finished lower level - recreation area with a glass-enclosed gym or office Private terrace and lawn. Attached 2-car garage A move-in-ready path to newer construction, minutes to the village and the train.

6 Down River Rd Unit 2, New Canaan

$4,595,000
6 Beds 7 Baths ACTIVE Status 24203624 MLS
A remarkable home where historic charm has been completely reimagined for modern living, set on over two acres in one of New Canaan's most coveted locations. Impeccably cared for and thoughtfully updated throughout, this stately residence offers over 7,000 square feet of beautifully appointed interiors with six bedrooms, six-and-a-half bathrooms, custom millwork and moldings, soaring ceilings, and exceptional attention to detail. A welcoming entry and adjoining office open to an elegant living room with double-sided gas fireplace and formal dining room with butler's pantry. Designed equally for effortless entertaining and everyday living, the heart of the home is an extraordinary custom kitchen with ample storage opening to an impressive, light-filled family room. Multiple French doors extend the living spaces outdoors to the rear porches, sweeping lawns, and pool. A powder room, two bedrooms, full bath, and mudroom provide added flexibility on the main level. Upstairs, the luxurious primary suite is a true retreat with fireplace, balcony, spa-like bath, and three walk-in closets. Three additional bedrooms, three bathrooms, a second family room, and laundry room complete the second level. The lower level offers additional living space with a bonus room, access to the three-car garage, and a fabulous cabana room with wet bar, updated full bath, and sliding doors opening directly to the pool for effortless summer entertaining.

125 West Rd, New Canaan

$11,500
4 Beds 2 Baths ACTIVE Status 24202954 MLS
Redesigned for elevated living, this fully renovated 4-bedroom home combines open-concept style with seamless functional flow, offering near single-level living on a private, scenic lot. An inviting entry opens into an informal living room with a cozy fireplace, a high-impact great room featuring soaring cathedral ceilings, stylish beams, and French doors that flood the space with natural light. At the heart of the home, the chef's kitchen boasts exceptional counter space, professional-grade appliances, and a massive center island with seating for effortless entertaining or ease of everyday living. The main living space opens to a private wrap-around back porch with built-in corner seating & planters, perfect for outdoor relaxation overlooking the tranquil, tree-lined yard with an area for a garden.A separate wing houses the private primary suite-a serene retreat styled with shiplap walls, vaulted ceilings, large picture window, and spa-inspired bath complete with dual sinks, a freestanding soaking tub, a custom marble shower, and skylights. Three additional light-filled bedrooms and a full bath provide comfortable accommodations for guests or family.Complete with an attached 2-car garage, lower level flexible space and laundry, storage shed, and a lush, rolling lawn.This turnkey residence offers easy living just minutes from everyday conveniences, award-winning New Canaan schools, the Nature Center, Waveny Park, designer boutiques, NYC-inspired dining & the Metro North train

99 Weed St, New Canaan

$3,495,000
3 Beds 5 Baths ACTIVE Status 24200998 MLS
This luxury custom designed home in a private country setting offers maximum privacy and comfortable living. The main level offers single floor living featuring a private primary suite with dressing room, full bath and French doors to a full screened porch with fireplace. The living room under a cathedral ceiling with fireplace and its own terrace access. An eat in kitchen with bay windows, breakfast nook, granite counters, Sub-Zero and Wolf range, powder room. A private office with bay windows. Laundry off a stone floored mudroom with built ins. Upstairs, a loft family room under a vaulted ceiling. Additional 2nd floor space includes a bedroom with full bath, and recreation room with adjoining bedroom and full bath that functions as a self-contained guest suite. The lower level adds a media room with wet bar, built ins and half bath, plus a second recreation room. Each room thoughtfully designed without compromise. Geothermal heating and cooling, whole house generator, noise reduction windows, cedar siding, stone exterior, wood shingle roof, three car attached heated garage and two fireplaces set the stage for effortless living.

700 N Wilton Rd, New Canaan

$1,739,000
3 Beds 3 Baths ACTIVE Status 24198972 MLS Stepping Stones BLDG.
A rare opportunity to own a truly unique residence in a granite and limestone estate of historic significance, just moments from the heart of downtown New Canaan. Set on three beautifully landscaped acres, Stepping Stones is a distinguished community of only eight bespoke condominiums offering an impressive castle like setting with exceptional period craftsmanship throughout. This spacious 2,090sf residence features 3 bedrooms and 2.1 bathrooms, soaring ceilings, European millwork and distinctive Hope steel windows. The updated kitchen opens to beautiful hardwood flooring that continues through the living room and two bedrooms. The living room is highlighted by a fireplace and impressive architectural details. The primary suite features slate flooring, a private full bathroom and built in closets. Step outside to an amazing private rear patio surrounded by the beautifully maintained grounds, creating a peaceful setting for relaxing or entertaining. Rich in character and architectural detail, this one of a kind residence offers a combination of history, charm and convenience that is rarely found.

705 Weed St Unit 2, New Canaan

$1,249,000
4 Beds 2 Baths ACTIVE Status 24195032 MLS
Well maintained 4-bedroom, 2-bath raised ranch, ideally situated on a quiet cul-de-sac just minutes from downtown New Canaan, schools, and much more! Offering a wonderful combination of comfort, location, and future potential, this home features a spacious, functional layout and a fantastic backyard perfect for entertaining, outdoor play, or simply enjoying the peaceful setting. Recent updates include a freshly painted interior, new light fixtures, door hardware, and refinished hardwood floors. Even better, all of the major improvements have already been completed, including a newer roof, gutters, siding, windows, 200-amp electrical service, water heater, and A/C compressor.With its extensive recent improvements and thoughtful updates throughout, this home is truly move-in ready and ready to welcome its next owners.

20 Lincoln Dr, New Canaan

$475,000
2 Beds 1 Baths ACTIVE Status 24197833 MLS Oenoke BLDG.
Welcome to easy in-town living at Oenoke Condominiums! This sun-filled, immaculate two-bedroom residence on the 2nd floor enjoys a wonderful location overlooking the large, inviting pool, making a refreshing summer dip just steps from your door. Freshly painted and move-in ready, the home features a spacious living room, an easy-flow floor plan, two generously sized bedrooms with large closets, and abundant natural light throughout. Recent updates include a new GE five-burner glass-top range and Whirlpool over-the-range microwave. Replacement windows were installed in 2014 and include a limited lifetime warranty. Additional conveniences include private storage and laundry facilities in the basement, while heat and hot water are included in the common charges. Best of all, leave the car behind! Enjoy an easy stroll to the heart of New Canaan for exceptional dining, unique shops, parks, the library, and Metro-North service to NYC. With New Canaan's highly regarded schools, beautiful parks and outstanding recreational amenities nearby, this bright and beautifully maintained home offers the perfect combination of comfort, convenience and an exceptional in-town lifestyle.

114 Heritage Hill Rd Unit C, New Canaan

$6,750
4 Beds 2 Baths ACTIVE Status 24197645 MLS
Experience refined living in this beautifully renovated townhouse-style condominium, ideally situated in the heart of New Canaan. Offering four bedrooms, two full bathrooms, and a finished third floor, this exceptional residence combines timeless elegance with modern comfort and effortless functionality. The thoughtfully updated interior features a designer-inspired kitchen with elegant quartz countertops conviniently opens to an expansive deck. Beautifully renovated bathrooms, pristine hardwood floors, and an abundance of natural light throughout. The spacious and versatile layout provides plenty of room for both everyday living and entertaining. The first floor offers a private bedroom and full bathroom, perfect for guests, a home office, or flexible living arrangements. The finished third floor provides additional space that can be tailored to your lifestyle. Ideally located just moments from New Canaan's brand-new library, charming downtown, acclaimed restaurants and shops, and the train station, this home offers the rare combination of sophisticated living and unparalleled convenience. Plenty of parking space. A truly exceptional opportunity to enjoy the best of New Canaan living. Qualified tenants only. Good credit, verifiable income, and strong references required. Two months' security deposit and one month's rent in advance required.

123 East Ave, New Canaan

$1,559,000
3 Beds 3 Baths ACTIVE Status 24197328 MLS Leefair BLDG.
Sophisticated one-level living awaits in this beautifully renovated three bedrooms,three full bathrooms coveted end unit in the desirable Leefair community. The sunny interior features an open, thoughtfully designed floor plan with a generous living room with fireplace flanked by book shelves which is open to the dining room with its French doors to the outdoors, a sleek updated eat-in kitchen, a spacious primary ensuite, another bedroom and an open family room. Plantation shutters add a touch of elegance throughout. The lower level has a large office, second family room, third large bedroom and a full bath, along with your laundry. There's an attached two car garage, too. From the dining room French doors, step outside to your own fenced and private patio~just perfect for outdoor dining, entertaining and relaxing in a peaceful setting. The gate allows access to a path for your walk into the heart of downtown New Canaan and the Metro North station. This exceptional turnkey home combines timelessness, along with modern comfort in one of the town's most desirable condo enclaves.

59 Bank St Unit 59, New Canaan

$3,500
2 Beds 1 Baths ACTIVE Status 24196874 MLS
Amazing opportunity to live in the heart of New Canaan! This charming two-bedroom apartment offers a wonderful combination of comfort, character, and convenience. The inviting living room features a handsome wood-burning fireplace, while the well-appointed kitchen includes a built-in washer and dryer. Two bright bedrooms and a full bath complete the home. New energy-efficient propane heating adds to the comfort and efficiency. Enjoy the charming grounds, including a delightful private yard and garden setting-an appealing outdoor retreat rarely found so close to town. Ideally located within easy walking distance to New Canaan's vibrant downtown, with its exceptional restaurants, boutique shopping, parks, library, cultural attractions, and Metro-North train station with direct service to Grand Central Terminal. A wonderful opportunity to enjoy all that New Canaan has to offer in a highly desirable in-town location. There is also an adjoining garage available for rent for an additional $250 month.

19 Urban St, New Canaan

$1,095,000
3 Beds 2 Baths ACTIVE Status 24195555 MLS
The Ultimate Canvas on the Cul-de-Sac: Shine Bright in the Village Corridor! Tucked away on one of the neighborhood's most coveted, postcard-worthy cul-de-sacs, this rare gem serves up the ultimate blend of peaceful seclusion and unbeatable village convenience-complete with sidewalks taking you right to the heart of the action! Perched on a flat, dry, and bathed-in-sunlight .32-acre parcel, the south-facing orientation floods the property with natural light all day long. Whether you choose to reimagine the existing, 3-bedroom, 1.5-bath home or bring your dream team to build a custom masterpiece from the ground up, the possibilities here are endless. Set among a gorgeous tapestry of mature landscaping, meticulous existing homes, and impressive multi-million-dollar new construction, you are investing in a premier street where location is king and the upside is limitlessly bright. Just minutes from the train, vibrant village life, and top-rated New Canaan schools.

19 S Down River Rd, New Canaan

$1,095,000
ACTIVE Status 24195736 MLS
The Ultimate Canvas on the Cul-de-Sac: Build Your Vision in the Village Corridor! Tucked away on one of the neighborhood's most coveted, postcard-worthy cul-de-sacs, this rare 0.32-acre land opportunity serves up the ultimate blend of peaceful seclusion and unbeatable village convenience-complete with sidewalks leading right to the heart of town. Perched on a flat, dry, and sun-drenched south-facing parcel, the site provides an optimal level footprint with all-day natural light, ready for you to bring your dream team and build a custom masterpiece from the ground up. Set among a gorgeous tapestry of mature greenery and impressive multi-million-dollar new construction, you are investing in a premier street where location is king, upside is limitlessly bright, and top-rated New Canaan schools and the train are just minutes away.

19 Down River Rd, New Canaan

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