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Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush landscape inside. At the heart of the home, a newly updated gourmet kitchen serves as a culinary showpiece. The primary suite is a true retreat, offering a private balcony, fireplace, and the rare luxury of dual bathrooms. Each of the six bedrooms in the main house features an ensuite bath, ensuring absolute privacy for family and guests alike. The amenities rival the world's finest resorts: a walk-out lower level equipped with a theater and wine room, and a 30x50 lagoon-style pool. The 2020-built pool house (700+ sq. ft.) provides a full guest experience with its own kitchen, bath, and flexible sleeping quarters-all just five minutes from the boutiques and bistros of New Canaan's vibrant village center.

7 Beds ⋅ 10 Baths ⋅ 24163175 MLS

Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush landscape inside. At the heart of the home, a newly updated gourmet kitchen serves as a culinary showpiece. The primary suite is a true retreat, offering a private balcony, fireplace, and the rare luxury of dual bathrooms. Each of the six bedrooms in the main house features an ensuite bath, ensuring absolute privacy for family and guests alike. The amenities rival the world's finest resorts: a walk-out lower level equipped with a theater and wine room, and a 30x50 lagoon-style pool. The 2020-built pool house (700+ sq. ft.) provides a full guest experience with its own kitchen, bath, and flexible sleeping quarters-all just five minutes from the boutiques and bistros of New Canaan's vibrant village center.

1421 Oenoke Rdg, New Canaan

$4,395,000

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.

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

$4,000,000

An icon of American modernism, the celebrated Celanese House presents a rare opportunity to own one of New Canaan's most architecturally significant residences. Designed in 1959 by acclaimed architect Edward Durell Stone, this internationally recognized masterpiece has been admired for decades for its timeless design. Meticulously restored to honor Stone's original vision while embracing contemporary living, the home showcases his signature architectural vocabulary-from the striking lattice facade and sculptural glass roof pyramids to soaring walls of glass that dissolve the boundary between indoors and out. Light becomes an architectural element, filling every space and transforming the home throughout the day. Nearly 5,000 square feet of thoughtfully curated living space blend historic integrity with refined modern luxury. Satin-bleached oak floors, floating walls, museum-quality lighting and a dramatic illuminated glass entry create interiors that feel simultaneously iconic and effortlessly livable. Four bedrooms, four-and-a-half baths and beautifully proportioned entertaining spaces provide exceptional comfort without compromising the purity of the original design. Set on 2.06 private acres along a distinguished road, the landscape complements the architecture with tranquil views and remarkable privacy. More than a residence, the Celanese House is an enduring work of architecture-offering the privilege of becoming the next steward of a true design landmark.

4 Beds ⋅ 5 Baths ⋅ 24189751 MLS

An icon of American modernism, the celebrated Celanese House presents a rare opportunity to own one of New Canaan's most architecturally significant residences. Designed in 1959 by acclaimed architect Edward Durell Stone, this internationally recognized masterpiece has been admired for decades for its timeless design. Meticulously restored to honor Stone's original vision while embracing contemporary living, the home showcases his signature architectural vocabulary-from the striking lattice facade and sculptural glass roof pyramids to soaring walls of glass that dissolve the boundary between indoors and out. Light becomes an architectural element, filling every space and transforming the home throughout the day. Nearly 5,000 square feet of thoughtfully curated living space blend historic integrity with refined modern luxury. Satin-bleached oak floors, floating walls, museum-quality lighting and a dramatic illuminated glass entry create interiors that feel simultaneously iconic and effortlessly livable. Four bedrooms, four-and-a-half baths and beautifully proportioned entertaining spaces provide exceptional comfort without compromising the purity of the original design. Set on 2.06 private acres along a distinguished road, the landscape complements the architecture with tranquil views and remarkable privacy. More than a residence, the Celanese House is an enduring work of architecture-offering the privilege of becoming the next steward of a true design landmark.

565 Oenoke Rdg, New Canaan

$3,995,000

Ideally located on a private lot in close proximity to public and private schools, 25 Hillcrest Rd. is located on a low traffic street on New Canaan's lower west side within minutes of the Merritt Parkway, Talmadge Hill train station and down town New Canaan. Spanning close to 8,000 sq ft, the transitional floor plan masterfully blends open concept spaces with more intimate, private spaces. Featuring 9' ceilings throughout and a clean, contemporary design aesthetic, the gracious home is perfect for entertaining large crowds while at the same time comfortable for everyday living. Entering through the custom designed front door, you are welcomed by a grand foyer with unobstructed views through the living room to the private backyard. As you move through the home, the centrally located family room is connected to both the large formal dining room and the gourmet kitchen which is flooded with natural light through six over sized windows. Featuring a clean, white design aesthetic the kitchen is as functional as it is beautiful. With a large 8.5' island coupled with two sinks and two dishwashers, prep and clean-up is easy. The adjacent pantry with lots of cabinetry and mudroom provide a place for everything, keeping the main living area neat and tidy. Not to be missed on the 1st floor is the large en suite guest bedroom (which could also serve as the primary bedroom) and a large private office.

6 Beds ⋅ 7 Baths ⋅ 24169909 MLS

Ideally located on a private lot in close proximity to public and private schools, 25 Hillcrest Rd. is located on a low traffic street on New Canaan's lower west side within minutes of the Merritt Parkway, Talmadge Hill train station and down town New Canaan. Spanning close to 8,000 sq ft, the transitional floor plan masterfully blends open concept spaces with more intimate, private spaces. Featuring 9' ceilings throughout and a clean, contemporary design aesthetic, the gracious home is perfect for entertaining large crowds while at the same time comfortable for everyday living. Entering through the custom designed front door, you are welcomed by a grand foyer with unobstructed views through the living room to the private backyard. As you move through the home, the centrally located family room is connected to both the large formal dining room and the gourmet kitchen which is flooded with natural light through six over sized windows. Featuring a clean, white design aesthetic the kitchen is as functional as it is beautiful. With a large 8.5' island coupled with two sinks and two dishwashers, prep and clean-up is easy. The adjacent pantry with lots of cabinetry and mudroom provide a place for everything, keeping the main living area neat and tidy. Not to be missed on the 1st floor is the large en suite guest bedroom (which could also serve as the primary bedroom) and a large private office.

25 Hillcrest Rd, New Canaan

$3,495,000

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.

3 Beds ⋅ 5 Baths ⋅ 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

$3,450,000

A rare find in the heart of New Canaan - walkable to both town and train - this beautifully renovated (2012-2014) 4/5 bedroom, 5 bath home features a backyard oasis few properties can match. Inside, a beamed cathedral ceiling soars above the great room, where a grand arched hearth of rare scale invites long fireside evenings. Mornings, gather around the marble island in the chef's kitchen, outfitted with top-of-the-line appliances and open to the family room. A den/study, bedroom or office, full bath, powder room, huge mudroom, and laundry complete this level's easy flow. The upper floors feature a primary bedroom with its own fireplace, walk-in closet and marble bath; two additional bedrooms; a third-floor suite with bath - and there's even an exercise room over the garage. Then comes the surprise: behind the house, towering evergreens and fieldstone walls enclose a secret garden so private you'd never guess that town is steps away. As dusk falls, the heated pool and spa glow, while the fire pit flickers. This special property is not to be missed.

5 Beds ⋅ 5 Baths ⋅ 24207854 MLS

A rare find in the heart of New Canaan - walkable to both town and train - this beautifully renovated (2012-2014) 4/5 bedroom, 5 bath home features a backyard oasis few properties can match. Inside, a beamed cathedral ceiling soars above the great room, where a grand arched hearth of rare scale invites long fireside evenings. Mornings, gather around the marble island in the chef's kitchen, outfitted with top-of-the-line appliances and open to the family room. A den/study, bedroom or office, full bath, powder room, huge mudroom, and laundry complete this level's easy flow. The upper floors feature a primary bedroom with its own fireplace, walk-in closet and marble bath; two additional bedrooms; a third-floor suite with bath - and there's even an exercise room over the garage. Then comes the surprise: behind the house, towering evergreens and fieldstone walls enclose a secret garden so private you'd never guess that town is steps away. As dusk falls, the heated pool and spa glow, while the fire pit flickers. This special property is not to be missed.

284 Park St, New Canaan

$2,785,000

Set back at the end of a private lane and only 1.5 miles from the center of New Canaan, this enchanting 1924 Cape exudes timeless elegance and undeniable charm. Set on 2.2 lush, flat acres, the property offers a serene retreat with expansive grounds ideal for relaxation and hosting. The chef's kitchen features top tier appliances and quartz countertops that balance beauty with functionality, and it opens seamlessly into the family room for effortless everyday living. The spacious living room showcases French doors that lead to a breathtaking park-like setting with a built-in outdoor grill and stone fireplace. The first-floor primary suite is approached through a cozy sitting room with a fireplace, creating an intimate and inviting entry. Four beautifully finished bedrooms complete the home, each crafted with thoughtful detail and classic appeal. The expansive bonus room above the garage-complete with a full bathroom and steam shower-offers exceptional versatility, perfect for a home gym, recreation room, private office, or guest suite. Brand new septic system!

5 Beds ⋅ 5 Baths ⋅ 24193634 MLS

Set back at the end of a private lane and only 1.5 miles from the center of New Canaan, this enchanting 1924 Cape exudes timeless elegance and undeniable charm. Set on 2.2 lush, flat acres, the property offers a serene retreat with expansive grounds ideal for relaxation and hosting. The chef's kitchen features top tier appliances and quartz countertops that balance beauty with functionality, and it opens seamlessly into the family room for effortless everyday living. The spacious living room showcases French doors that lead to a breathtaking park-like setting with a built-in outdoor grill and stone fireplace. The first-floor primary suite is approached through a cozy sitting room with a fireplace, creating an intimate and inviting entry. Four beautifully finished bedrooms complete the home, each crafted with thoughtful detail and classic appeal. The expansive bonus room above the garage-complete with a full bathroom and steam shower-offers exceptional versatility, perfect for a home gym, recreation room, private office, or guest suite. Brand new septic system!

758 Smith Ridge Rd, New Canaan

$2,695,000

Experience elevated living in the heart of downtown New Canaan with this exquisite boutique enclave offering just 7 luxury residences. Built with the best finishes in mind, this home features 3,351 sq ft of finished space, Elevator, large-pane oversized windows, and a thoughtfully designed layout that centers around your gourmet kitchen featuring custom cabinetry, gorgeous island with 2" countertops, chefs appliances, and breakfast area that opens to the family room with gas fireplace and sliders overlooking the fabulous terrace creating the perfect indoor/outdoor living experience. Exquisite mill work, white oak floors, custom staircases, and built-ins truly show meticulous attention to detail. Absolutely spectacular primary bedroom with walk-in closet, and spa inspired bathroom that will take your breath away featuring a 8ft x 4ft walk in shower, soaking tub, floating vanity, and heated floors. Take the elevator or stairs to the finished 3rd floor and enjoy sunsets from your private rooftop deck overlooking Mead Park. "The Enclave on Richmond" offers privacy, elegance, and convenience with just a few steps to New Canaan's shops, restaurants, and Metro-North station. Truly a one-of-a-kind residence.

4 Beds ⋅ 5 Baths ⋅ 24185149 MLS ⋅ Enclave On Richmond - Pending Verification BLDG.

Experience elevated living in the heart of downtown New Canaan with this exquisite boutique enclave offering just 7 luxury residences. Built with the best finishes in mind, this home features 3,351 sq ft of finished space, Elevator, large-pane oversized windows, and a thoughtfully designed layout that centers around your gourmet kitchen featuring custom cabinetry, gorgeous island with 2" countertops, chefs appliances, and breakfast area that opens to the family room with gas fireplace and sliders overlooking the fabulous terrace creating the perfect indoor/outdoor living experience. Exquisite mill work, white oak floors, custom staircases, and built-ins truly show meticulous attention to detail. Absolutely spectacular primary bedroom with walk-in closet, and spa inspired bathroom that will take your breath away featuring a 8ft x 4ft walk in shower, soaking tub, floating vanity, and heated floors. Take the elevator or stairs to the finished 3rd floor and enjoy sunsets from your private rooftop deck overlooking Mead Park. "The Enclave on Richmond" offers privacy, elegance, and convenience with just a few steps to New Canaan's shops, restaurants, and Metro-North station. Truly a one-of-a-kind residence.

14 Richmond Hill Rd Unit 4, New Canaan

$2,550,000

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.

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

$2,500,000

Experience elevated living in the heart of downtown New Canaan with this exquisite boutique enclave offering just 7 luxury residences. Built with the best finishes in mind, this home features 2,998 sq ft of finished space, Elevator, large-pane oversized windows, and a thoughtfully designed layout that centers around your gourmet kitchen featuring custom cabinetry, gorgeous island with 2" countertops, chefs appliances, and breakfast area that opens to the family room with gas fireplace and sliders overlooking the fabulous terrace creating the perfect indoor/outdoor living experience. Exquisite mill work, white oak floors, custom staircases, and built-ins truly show meticulous attention to detail. Absolutely spectacular primary bedroom with walk-in closet, and spa inspired bathroom that will take your breath away featuring a 8ft x 4ft walk in shower, soaking tub, floating vanity, and heated floors. Take the elevator or stairs to the finished 3rd floor and enjoy sunsets from your private rooftop deck overlooking Mead Park. "The Enclave on Richmond" offers privacy, elegance, and convenience with just a few steps to New Canaan's shops, restaurants, and Metro-North station. Truly a one-of-a-kind residence.

4 Beds ⋅ 5 Baths ⋅ 24189509 MLS ⋅ Enclave On Richmond - Pending Verification BLDG.

Experience elevated living in the heart of downtown New Canaan with this exquisite boutique enclave offering just 7 luxury residences. Built with the best finishes in mind, this home features 2,998 sq ft of finished space, Elevator, large-pane oversized windows, and a thoughtfully designed layout that centers around your gourmet kitchen featuring custom cabinetry, gorgeous island with 2" countertops, chefs appliances, and breakfast area that opens to the family room with gas fireplace and sliders overlooking the fabulous terrace creating the perfect indoor/outdoor living experience. Exquisite mill work, white oak floors, custom staircases, and built-ins truly show meticulous attention to detail. Absolutely spectacular primary bedroom with walk-in closet, and spa inspired bathroom that will take your breath away featuring a 8ft x 4ft walk in shower, soaking tub, floating vanity, and heated floors. Take the elevator or stairs to the finished 3rd floor and enjoy sunsets from your private rooftop deck overlooking Mead Park. "The Enclave on Richmond" offers privacy, elegance, and convenience with just a few steps to New Canaan's shops, restaurants, and Metro-North station. Truly a one-of-a-kind residence.

20 Richmond Hill Rd Unit 1, New Canaan

$2,495,000

Highly sought-after Leefair end unit offering true ranch-style living with exceptional privacy and a first-floor layout designed for comfort and convenience. This 4-bedroom, 3.5 bath home features a first-floor primary suite plus an additional first-floor bedroom with its own full bath-ideal for guests, multigenerational living, or a private office suite. The second floor adds two additional bedrooms, a full bath, and a generous sitting room that creates a perfect retreat for guests, teens, or flexible bonus space. The main level enjoys garden and patio views, with three separate entrance points and direct terrace access from both the living room and the primary suite. The living room stands out with coffered ceilings, soaring height, abundant natural light, and custom built-ins that elevate both style and functionality. A spacious two-car garage with built-in cabinetry offers organized storage, and a brand-new AC system ensures year-round comfort. Set within the coveted Leefair community-known for its convenience, beautifully maintained grounds, and low maintenance lifestyle-this end unit presents a rare opportunity to enjoy generous square footage, thoughtful design, and a premier in-town location.

4 Beds ⋅ 4 Baths ⋅ 24204076 MLS ⋅ Leefair BLDG.

Highly sought-after Leefair end unit offering true ranch-style living with exceptional privacy and a first-floor layout designed for comfort and convenience. This 4-bedroom, 3.5 bath home features a first-floor primary suite plus an additional first-floor bedroom with its own full bath-ideal for guests, multigenerational living, or a private office suite. The second floor adds two additional bedrooms, a full bath, and a generous sitting room that creates a perfect retreat for guests, teens, or flexible bonus space. The main level enjoys garden and patio views, with three separate entrance points and direct terrace access from both the living room and the primary suite. The living room stands out with coffered ceilings, soaring height, abundant natural light, and custom built-ins that elevate both style and functionality. A spacious two-car garage with built-in cabinetry offers organized storage, and a brand-new AC system ensures year-round comfort. Set within the coveted Leefair community-known for its convenience, beautifully maintained grounds, and low maintenance lifestyle-this end unit presents a rare opportunity to enjoy generous square footage, thoughtful design, and a premier in-town location.

39 Bank St Unit 39, New Canaan

$2,300,000

Classic Connecticut! Welcome to this spacious 5 bedroom Connecticut home in New Canaan. Stunning pastoral and romantic scenery, stone walls, and stunning heritage trees throughout your private 2 acre property on Cul-de-sac Street. The beautiful and historic Selleck's Chapel is right around the corner. Enjoy your very own post-and-beam detached barn which offers a two-car garage additional flex space, and a loft inside. Inground gunite pool with cabana and patio receive direct sunlight, allowing for fantastic entertaining flow. It's a 7 minute picturesque drive to town on Oenoke Ridge. Brought up to today's standards with new solar panels paid in full, EV charger and a house generator. Guests approach through a circular driveway, with an additional driveway leading to the gorgeous barn for everyday living and mudroom access. This center hall colonial features a gourmet kitchen adjacent to a family room with a fireplace, vaulted ceilings and natural light. Large dining room and living room with wood burning fireplace, lead into an office or bonus room featuring exquisite antique barn floors and vaulted ceilings. 500 ADDITIONAL square feet in lower level! That has a private guest suite with full bath, large laundry room, and playroom or gym. Primary bedroom with ensuite bath on the second floor has balcony overlooking the property grounds perfect for sunsets or morning coffee. 3 additional bedrooms round out the second floor with a shared, renovated bath. Welcome to New Canaan!

5 Beds ⋅ 4 Baths ⋅ 24204185 MLS

Classic Connecticut! Welcome to this spacious 5 bedroom Connecticut home in New Canaan. Stunning pastoral and romantic scenery, stone walls, and stunning heritage trees throughout your private 2 acre property on Cul-de-sac Street. The beautiful and historic Selleck's Chapel is right around the corner. Enjoy your very own post-and-beam detached barn which offers a two-car garage additional flex space, and a loft inside. Inground gunite pool with cabana and patio receive direct sunlight, allowing for fantastic entertaining flow. It's a 7 minute picturesque drive to town on Oenoke Ridge. Brought up to today's standards with new solar panels paid in full, EV charger and a house generator. Guests approach through a circular driveway, with an additional driveway leading to the gorgeous barn for everyday living and mudroom access. This center hall colonial features a gourmet kitchen adjacent to a family room with a fireplace, vaulted ceilings and natural light. Large dining room and living room with wood burning fireplace, lead into an office or bonus room featuring exquisite antique barn floors and vaulted ceilings. 500 ADDITIONAL square feet in lower level! That has a private guest suite with full bath, large laundry room, and playroom or gym. Primary bedroom with ensuite bath on the second floor has balcony overlooking the property grounds perfect for sunsets or morning coffee. 3 additional bedrooms round out the second floor with a shared, renovated bath. Welcome to New Canaan!

23 Jonathan Rd, New Canaan

$2,000,000

PLEASE SUBMIT ALL OFFERS BY 5PM TUESSStep into a seamless blend of historic charm and modern luxury, ideally located in the heart of New Canaan. Nestled on 1.46 lush, private acres, this beautifully maintained Farmhouse Colonial offers the quintessential New England lifestyle. Spanning 3,383 square feet, this unique home has been thoughtfully updated to feature 5 spacious bedrooms and 5 full bathrooms. From the moment you step inside, you are greeted by pristine interiors and gleaming refinished floors. The inviting, sun-drenched layout is tailor-made for both relaxed everyday living and elegant entertainment. Outside, a true sanctuary awaits. Spend your summers enjoying the sparkling pool, running across the expansive play space, or picking fruit from your very own apple trees. Attached is a year-round pool house featuring a full bath and a gym room. A standout feature of this property is the spectacular detached guest house. Complete with a kitchenette, a spacious great room, and a beautifully appointed bathroom, it offers unmatched versatility. Whether you envision a welcoming suite for extended family and au pairs, a quiet home office away from the main house, or a creative studio for music and art, this space easily adapts to your imagination. Ideally located just minutes from the train, the Merritt Parkway, and award-winning schools, this move-in-ready gem delivers absolute convenience without sacrificing tranquility.

5 Beds ⋅ 5 Baths ⋅ 24206478 MLS

PLEASE SUBMIT ALL OFFERS BY 5PM TUESSStep into a seamless blend of historic charm and modern luxury, ideally located in the heart of New Canaan. Nestled on 1.46 lush, private acres, this beautifully maintained Farmhouse Colonial offers the quintessential New England lifestyle. Spanning 3,383 square feet, this unique home has been thoughtfully updated to feature 5 spacious bedrooms and 5 full bathrooms. From the moment you step inside, you are greeted by pristine interiors and gleaming refinished floors. The inviting, sun-drenched layout is tailor-made for both relaxed everyday living and elegant entertainment. Outside, a true sanctuary awaits. Spend your summers enjoying the sparkling pool, running across the expansive play space, or picking fruit from your very own apple trees. Attached is a year-round pool house featuring a full bath and a gym room. A standout feature of this property is the spectacular detached guest house. Complete with a kitchenette, a spacious great room, and a beautifully appointed bathroom, it offers unmatched versatility. Whether you envision a welcoming suite for extended family and au pairs, a quiet home office away from the main house, or a creative studio for music and art, this space easily adapts to your imagination. Ideally located just minutes from the train, the Merritt Parkway, and award-winning schools, this move-in-ready gem delivers absolute convenience without sacrificing tranquility.

327 Jelliff Mill Rd, New Canaan

$1,995,000

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.

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 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

$1,595,000

Enjoy living in this beautifully renovated end-unit townhouse in the heart of New Canaan. This sun-filled home has it all with wide-plank white oak flooring, stunning eat-in kitchen with quartz countertops, Thermador appliances, dry bar and a custom pantry and laundry room. The spacious living room has a gas fireplace, dining area and opens seamlessly to a private fully fenced patio- perfect for a morning coffee, outdoor dining or relaxed entertaining. The upper level offers two large en-suite bedrooms with walk-in closets. The finished expansive lower level with a half bath provides exceptional living space for a family room, private office, fitness area or media room. All major mechanical systems were newly installed in 2023 including Bosch central air conditioning, a Weil-McLain boiler and a Bradford White hot water heater. Located steps to the train station, dining, boutique shopping, cafes and the vibrant downtown that New Canaan has to offer. This turn-key townhouse with three reserved parking spaces and a attached garage is not to be missed. A must see!

2 Beds ⋅ 3 Baths ⋅ 24209252 MLS ⋅ Maple Park Commons BLDG.

Enjoy living in this beautifully renovated end-unit townhouse in the heart of New Canaan. This sun-filled home has it all with wide-plank white oak flooring, stunning eat-in kitchen with quartz countertops, Thermador appliances, dry bar and a custom pantry and laundry room. The spacious living room has a gas fireplace, dining area and opens seamlessly to a private fully fenced patio- perfect for a morning coffee, outdoor dining or relaxed entertaining. The upper level offers two large en-suite bedrooms with walk-in closets. The finished expansive lower level with a half bath provides exceptional living space for a family room, private office, fitness area or media room. All major mechanical systems were newly installed in 2023 including Bosch central air conditioning, a Weil-McLain boiler and a Bradford White hot water heater. Located steps to the train station, dining, boutique shopping, cafes and the vibrant downtown that New Canaan has to offer. This turn-key townhouse with three reserved parking spaces and a attached garage is not to be missed. A must see!

1 Maple St Unit 1, New Canaan

$1,559,000

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.

3 Beds ⋅ 3 Baths ⋅ 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

$1,395,000

Welcome to a Garden Paradise. Canaan Close is admired as the most beautifully landscaped Townhouse complex in New Canaan. With views and the "music" of the 5 mile river, heated pool retreat, fountain gardens and even a meandering River Walk, this is indeed one of New Canaan's most sought-after communities. This sophisticated 3 bedroom 3 bath end unit is bathed in sunlight and lives like a single family home. Entertaining and relaxing is a delight in your large light-filled living room and doors opening to your private balcony. What a better way to enjoy your coffee & croissants with views of the 5 mile river! Dine in your sophisticated dining room with crown molding or in your updated Decorator kitchen with a charming window seat and table. Your first floor spacious sitting room is also a first floor bedroom with bath. Great feature for family or guests! Upstairs there is an impressive balcony with dining and seating areas, two additional bedrooms -a beautiful Primary bedroom with large closets and updated bath. The lower level has a large family room and reading alcove, both opening to a lovely patio surrounded by lush gardens. Enjoy a short stroll to New Canaan's vibrant village center with its fine & fun restaurants, boutique shopping, library, parks, and train station. New Canaan's award winning schools are each close by. Canaan Close is a treasure in the Heart of New Canaan

3 Beds ⋅ 3 Baths ⋅ 24193137 MLS ⋅ Canaan Close BLDG.

Welcome to a Garden Paradise. Canaan Close is admired as the most beautifully landscaped Townhouse complex in New Canaan. With views and the "music" of the 5 mile river, heated pool retreat, fountain gardens and even a meandering River Walk, this is indeed one of New Canaan's most sought-after communities. This sophisticated 3 bedroom 3 bath end unit is bathed in sunlight and lives like a single family home. Entertaining and relaxing is a delight in your large light-filled living room and doors opening to your private balcony. What a better way to enjoy your coffee & croissants with views of the 5 mile river! Dine in your sophisticated dining room with crown molding or in your updated Decorator kitchen with a charming window seat and table. Your first floor spacious sitting room is also a first floor bedroom with bath. Great feature for family or guests! Upstairs there is an impressive balcony with dining and seating areas, two additional bedrooms -a beautiful Primary bedroom with large closets and updated bath. The lower level has a large family room and reading alcove, both opening to a lovely patio surrounded by lush gardens. Enjoy a short stroll to New Canaan's vibrant village center with its fine & fun restaurants, boutique shopping, library, parks, and train station. New Canaan's award winning schools are each close by. Canaan Close is a treasure in the Heart of New Canaan

289 New Norwalk Rd Unit 23, New Canaan

123 Richmond Hill Rd Unit 21, New Canaan

$1,369,000

Experience the perfect blend of townhouse convenience and single-family privacy in this beautifully updated home at Orchard Hills. Boasting an open-concept main floor, the residence features a gourmet kitchen complete with granite countertops, rich hardwood floors, and premium stainless steel appliances. The inviting living room, anchored by a classic marble fireplace, flows seamlessly into the dining area-creating an ideal space for hosting family and friends. Upstairs, you will find two spacious en-suite bedrooms, including a luxurious Primary Suite featuring a brand-new, spa-like bath and custom closet. The bright, walk-out lower level is a versatile haven, offering a family room with custom built-ins, ample space for a quiet home office, and a dedicated laundry room with abundant storage. Swing open the French doors to your private bluestone terrace, perfect for al fresco dining overlooking the manicured grounds. With the complex recently undergoing extensive renovations-including all-new siding, roofs, drainage, and landscaping-this home offers total peace of mind. Enjoy lazy afternoons by the community pool, or take a short, scenic stroll to Mead Park and the world-class dining and shopping in the Village of New Canaan.

2 Beds ⋅ 3 Baths ⋅ 24194602 MLS ⋅ Orchard Hills BLDG.

Experience the perfect blend of townhouse convenience and single-family privacy in this beautifully updated home at Orchard Hills. Boasting an open-concept main floor, the residence features a gourmet kitchen complete with granite countertops, rich hardwood floors, and premium stainless steel appliances. The inviting living room, anchored by a classic marble fireplace, flows seamlessly into the dining area-creating an ideal space for hosting family and friends. Upstairs, you will find two spacious en-suite bedrooms, including a luxurious Primary Suite featuring a brand-new, spa-like bath and custom closet. The bright, walk-out lower level is a versatile haven, offering a family room with custom built-ins, ample space for a quiet home office, and a dedicated laundry room with abundant storage. Swing open the French doors to your private bluestone terrace, perfect for al fresco dining overlooking the manicured grounds. With the complex recently undergoing extensive renovations-including all-new siding, roofs, drainage, and landscaping-this home offers total peace of mind. Enjoy lazy afternoons by the community pool, or take a short, scenic stroll to Mead Park and the world-class dining and shopping in the Village of New Canaan.

123 Richmond Hill Rd Unit 21, New Canaan

$1,249,000

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.

4 Beds ⋅ 2 Baths ⋅ 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

$1,150,000

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.

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