Refine Search
Map
Sort by
$4,700,000
6 Beds ⋅ 7 Baths ⋅ 24180326 MLS
Private New Canaan Oasis: Bespoke Luxury can be found in this modern version of a traditional centerhall colonial in prestigious New Canaan's West School district. This custom-built Lukes Wood estate underwent a spectacular renovation by Award-winning RR Builders, updating the sophisticated main residence to over 7,000 square feet of turnkey luxury. The expansive floor plan boasts 6 generously appointed bedrooms - each featuring an ensuite bath and walk-in closet alongside elegant formal living and dining rooms, a private office, a wine cellar, a butler's pantry, and a finished walk-out lower level with a full bath. At the heart of the home, a fully appointed chef's kitchen with a double island and professional-grade appliances flows into a sun-drenched breakfast room and a magnificent great room, which showcases a floor-to-ceiling stone fireplace, cathedral ceilings, and rustic beams. French doors transition seamlessly to an outdoor sanctuary featuring a 45' x 22' heated gunite pool, an expansive terrace, a pavilion with a firepit, private walking trails, plus a custom-built barn that offers additional space for cars, equipment, a gym, art studio, or large office space delivering an unparalleled, ultra-private retreat close to New Canaan's top-tier schools and vibrant community.

81 Lukes Wood Rd, New Canaan
$4,700,000
5 Beds ⋅ 8 Baths ⋅ 24165514 MLS
Located on one of New Canaan's most desirable streets, here's a home that immediately feels welcoming from the moment you arrive. Its sophisticated style and understated elegance create a quiet sense of calm the moment you walk through the doors. Filled with natural light and designed for both everyday living and elegant entertaining, this exceptional property offers timeless appeal in a beautifully private setting, just moments from town and perfectly positioned for both privacy and convenience. Professionally landscaped grounds with specimen trees further enhance the home's sense of beauty and privacy. Soaring ceilings and airy, light-filled rooms flow naturally from one to another, while elegant French doors open to a lushly landscaped courtyard, allowing the fountain and sparkling pool to become an extension of the living spaces. The formal living and dining rooms flow naturally into the airy eat-in kitchen with two chef's islands and dual ovens to a family room with a soaring cathedral ceiling and dramatic fieldstone fireplace, equally suited for intimate evenings by the fire or relaxed entertaining with family and friends. Radiant heated stone floors add warmth and comfort throughout the home's thoughtfully designed living spaces.

146 Lambert Rd, New Canaan
$4,700,000
5 Beds ⋅ 6 Baths ⋅ 24165312 MLS
Step into timeless sophistication at this breathtaking Neoclassical estate, ideally located on over 4 pristine acres in one of New Canaan's most sought-after locations. Offering 6,557 square feet of beautifully refined living space, this extraordinary home effortlessly balances classic architectural elegance with the comforts of modern luxury. Thoughtfully redesigned and expanded between 2010 and 2017, the main residence features 5 spacious bedrooms and 4.1 bathrooms, alongside formal living and dining rooms, a chef-inspired kitchen, a sunlit mudroom, and multiple inviting family and gathering spaces. Every room showcases meticulous craftsmanship, bespoke millwork, and exceptional finishes-designed for both everyday living and elegant entertaining. A charming detached carriage house adds even more flexibility, perfect as a guest retreat, home office, fitness studio, or private residence for in-laws or an au pair. It includes its own bedroom, full bath, kitchen, and living area. Outside, the estate unfolds into sweeping lawns, curated gardens, specimen trees, and beautifully designed hardscapes, including a sparkling pool and spa. With top-to-bottom improvements-new windows and doors, updated utilities, a re-sealed roof, and more-this home is as turnkey as it is timeless. This is a rare opportunity to own an iconic and serene legacy property in the heart of New Canaan-an estate that truly must be seen to be appreciated.

1191 Oenoke Rdg, New Canaan
$4,700,000
6 Beds ⋅ 8 Baths ⋅ 24157440 MLS
Welcome to 66 Stanton Road. Set on 1.34 landscaped acres, this classic 1938 clapboard colonial blends architectural charm with thoughtful updates, including a full renovation and expansion completed in 2009. Designed for effortless living and entertaining, the home offers refined formal rooms and relaxed gathering spaces. A gracious foyer with sweeping curved staircase is flanked by sunlit living and dining rooms. The open kitchen and family room anchor the home, featuring Wolf and Sub-Zero appliances, double ovens, a walnut island, generous pantry, and casual dining area. A vaulted, wood-paneled family room with exposed beams, fireplace, and a wall of windows overlooks the backyard. A wet bar with second dishwasher and built-in desk sits just off the kitchen. Upstairs, the spacious primary suite offers a vaulted ceiling, dressing area, reading porch, and spa-like bath with steam shower and soaking tub. Five additional bedrooms include two en suites and a Jack-and-Jill layout, plus a flexible lounge/study area and walk-up attic storage. The lower level includes a bar, fireplace lounge, climate-controlled wine room, and full gym. Outdoor living shines with a screened porch, patio with grill, and a recently added gunite pool with spa and electric cover. Lush lawns and vibrant plantings create privacy and seasonal color for both quiet enjoyment and lively gatherings.

66 Stanton Rd, Darien
$4,650,000
5 Beds ⋅ 6 Baths ⋅ 24134303 MLS
Discover New Canaan as it was meant to be. This stunner on coveted St. John's Place was built in 1910 and occupied by the same family for 44 years. Every year, the home was improved, and stands today as a testament to the labor of love built and cared for over four decades. Fully modernized to today's high standards with hints of its storied history as one of the loveliest homes in New Canaan. This quintessential home boasts classic cedar shingle siding and roof, high ceilings, 4 wood-burning fireplaces, bay windows, custom plantation shutters and beautiful wainscoting and molding throughout. Prime location on St. John's Place, steps from Elm and Park Street and bordering God's Acre. The picturesque property abuts ACRES of wooded conservation land with a charming, tucked-away pool surrounded by lush plantings and trees. Militantly maintained interiors lovingly updated with four en-suite bedrooms PLUS versatile library/office space with enchanting private spaces throughout this gracious home.

71 Saint Johns Pl, New Canaan
$4,600,000
5 Beds ⋅ 6 Baths ⋅ 24156751 MLS
Ideally situated between the coveted town centers of Darien and New Canaan, this exceptionally and recently completely redesigned colonial rests on 2.4 acres of pristine, park-like grounds. Enveloped by a perimeter of mature trees, a rare sense of serenity is felt upon arrival. Finished with an uncompromising attention to detail, a sophisticated design aesthetic and superior craftsmanship throughout, curated to deliver both timeless elegance and modern comfort. The heart of the home is a stunning chef's kitchen complemented by a walk-in butler's pantry and an exquisitely appointed bar. Expansive walls of glass bathe the interiors in natural light while seamlessly connecting indoor and outdoor living. Large family room, living room and dining rooms are part of the open floor plan. French doors open to an impressive flagstone terrace - the perfect setting for al fresco dining, sunset gatherings, and tranquil mornings overlooking the private grounds. A dramatic recreation room with soaring cathedral ceilings provides a striking architectural statement and an abundance of space for leisure and relaxation. The oversized three-car garage offers generous storage and flexibility to accommodate today's lifestyle needs. A luxurious master and additional 3 bedrooms complete the second flr. A 5th Bedroom can be found on the third flr. 15 Marianne Rd represents a rare opportunity to acquire a meticulously renovated estate where luxury, privacy, and location converge in perfect harmony.

15 Marianne Rd, Darien
$4,597,500
5 Beds ⋅ 7 Baths ⋅ 24161616 MLS
Set at the end of a coveted Fox Hill cul de sac on a private 1 acre lot, this spectacular 5 bedroom, 6 bath home offers an exceptional lifestyle defined by luxury, comfort, and effortless entertaining. Completely redesigned, the home is surrounded by open, beautifully manicured grounds with a premium lawn and expansive feel, combining privacy and serenity with a setting that feels both special and inviting. Designed for modern living, the home features four fireplaces, a stunning chef's kitchen with soaring ceilings, a statement center island, and high end appliances, as well as a private home office, theater room, gym with sauna, and a first floor in law suite with full bath. Outside, the resort style backyard is the ultimate private retreat, complete with a pool, hot tub, outdoor fire pit, and expansive mahogany deck for seamless indoor outdoor living. Warm, inviting, and beautifully designed, this is a rare opportunity to own a private oasis in one of Darien's most sought after locations.

21 Fox Hill Ln, Darien
$4,555,000
5 Beds ⋅ 8 Baths ⋅ 24126368 MLS
Luxury New Construction in the Heart of New Canaan! Coming Soon 2026! Experience the finest in modern living with this exceptional new home by Kaeser Custom Homes, renowned for quality craftsmanship and timeless design. Ideally situated between South Ave and South School, this elegant residence offers the perfect blend of neighborhood, convenience, and luxury-with sidewalk access to town for ultimate enjoyment. Spanning over 6,200 square feet across four beautifully finished levels, this 5 ensuite bedroom, 6 full and 2 half-bath masterpiece is thoughtfully designed for both everyday living and stylish entertaining. Highlights include: Gourmet chef's kitchen with top-tier appliances opens to a spacious family room with a fireplace. Luxurious primary suite with personal sitting room, spa-like bath and walk-in closet. Private home office, formal dining, and flexible living spaces. Finished lower level ideal for a gym and media room. Set on a picturesque lot with professionally landscaped grounds, this home is a rare opportunity to own a newly built property in one of New Canaan's in-town neighborhoods.

25 Gower St, New Canaan
$4,500,000
5 Beds ⋅ 4 Baths ⋅ 24185736 MLS
Welcome to 20 Buttonwood, a timeless Darien classic showcasing a renovated 5 bed 3.5 bath meticulously maintained home w/ expansive property & ultimate privacy. Set on a level, 1.25 acres the property is bordered by protected Land Trust. The flat/dry fenced yard provides endless possibilities for play, entertaining, gardening, and future enhancements. At the heart of the home is a beautifully renovated gourmet kitchen designed for both everyday living & effortless entertaining. The adjoining family, dining, living & sunrooms all flow seamlessly to the outdoor terrace, creating an ideal setting for indoor-outdoor living. Rounding out the first floor is the home office, and the newly renovated mudroom with custom built in lockers, radiant herringbone brick floors, natural oak desk, full size washer dryer & oversized soapstone sink. The 2nd level is home to all 5 bedrooms, including the primary suite w/ large balcony & an in-law suite with separate staircase for flexible living arrangements. The finished LL includes a gym and secondary laundry. The unfinished walk up 3rd floor provides great space for easily accessible storage or the option to finish for an additional 400+ sq ft of living space. Ideally situated on one of Darien's most coveted streets, just moments from Cherry Lawn Park, downtown Darien, Metro-North, and Ox Ridge Elementary, 20 Buttonwood offers a rare combination of escape and convenience. Don't miss this opportunity to own a Darien classic!

20 Buttonwood Ln, Darien
$4,500,000
5 Beds ⋅ 6 Baths ⋅ 24147232 MLS
Nestled on more than two private acres, 6 Cloudy Lane presents an exceptional opportunity to own a classic estate property in one of Darien's most coveted neighborhoods. A thoughtful renovation by renowned designer Louise Brooks introduced timeless architectural elements that continue to define the home today. Expansive rooms, elegant detailing, and walls of windows fill the interiors with natural light while framing serene views of the surrounding property. With approximately 5,900 square feet on two levels, the layout is designed for both sophisticated entertaining and comfortable everyday living. An inviting living room with a fireplace and a light-filled dining room with a bay window create elegant gathering spaces. The generous kitchen, featuring double islands and an eat-in area, flows effortlessly into the expansive family room, where a coffered ceiling, wood-burning fireplace, and French doors open to the outdoors-perfect for indoor-outdoor entertaining. Upstairs, the primary suite serves as a private retreat with tranquil views of the property, while four additional bedrooms provide comfortable accommodations for family and guests. The beautifully landscaped grounds include a tennis/pickleball court as well as a charming brick potting shed, offering endless possibilities as a changing room for tennis or a future pool. With its expansive lawn and mature trees, the property offers the potential to create a truly resort-like outdoor setting.

6 Cloudy Ln, Darien
$4,475,000
5 Beds ⋅ 5 Baths ⋅ 24182478 MLS
Beautifully renovated in 2019, this exceptional 5-bedroom home offers a seamless open floor plan, generous living spaces, & the rare combination of privacy & convenience. Perched atop a knoll & set back from the street, the property enjoys a peaceful setting while remaining just minutes from downtown train, restaurants & shopping. Designed for both everyday living & effortless entertaining, the sun-drenched interior features spacious, beautifully proportioned rooms throughout. The chef's kitchen opens to the family room & flows through French doors to an inviting outdoor terrace, creating the perfect indoor/outdoor lifestyle. A formal DR w butler's pantry is ideal for hosting, while the elegant LR showcases a stunning marble fireplace. A charming sunroom provides a cozy retreat for relaxing/reading. The luxurious primary suite features a striking lacquered vaulted ceiling & spa-inspired bath w double vanities, soaking tub & shower. 4 Addl BRs are served by 3 beautifully renovated baths, while a private tucked-away office offers ideal work-from-home space. Set on a 1.69-acre property, the grounds have been thoughtfully reimagined by a landscape architect & include multiple terraces, fairy trails & secluded fire pit. Expansive sunny flat lawns provide ample room for play, pets, & outdoor enjoyment, all within a fenced setting rarely found so close to town. A truly special offering that combines modern updates, exceptional outdoor spaces & a coveted walk to town/train location

174 Leroy Ave, Darien
$4,450,000
6 Beds ⋅ 5 Baths ⋅ 24185753 MLS
Extraordinary property. Exceptional location. A once-in-a- generation offering in one of Greenwich's most desirable in-town neighborhoods. Magnificently sited on 1.17 park-like acres along the sweeping curve of one Greenwich's most coveted cul-de-sacs, this custom-built residence offers an unparalleled combination of privacy, scale and convenience, just moments from top-rated schools, downtown Greenwich, fine dining, shopping, and Metro-North. Designed with timeless architecture and gracious proportions, this elegant six-bedroom, five-bath home showcases exceptional craftsmanship and remarkable flexibility for today's lifestyle. A distinctive feature is the private suite with its own driveway, entrance, and parking area--ideal for an in-law or nanny suite, home office, or multigenerational living. The breathtaking grounds are equally impressive, featuring sweeping lawns and an expansive, level backyard perfectly suited for entertaining, recreation, or future enhancements. An exceptional opportunity to own a legacy property where timeless elegance, extraordinary grounds and limitless potential converge in the heart of Greenwich.

17 Kenilworth Ter, Greenwich
$4,400,000
5 Beds ⋅ 5 Baths ⋅ 24166678 MLS
Modern Luxury Meets Classic Charm on Elm Place - Experience sophisticated living in this spectacular masterpiece situated on one of the area's most coveted streets, where a dramatic, light-drenched three-story foyer flows effortlessly into a formal dining room and a sprawling front-to-back living room anchored by a classic fireplace. The heart of the home features an open-concept gourmet kitchen and an inviting family room complete with a rugged stone fireplace, custom wet bar, and sunny breakfast nook. Through elegant French doors, the living space extends to an unparalleled outdoor oasis; this private sanctuary is anchored by an expansive stone terrace and a pristine, heated Gunite pool and spa, all framed by lush, professional landscaping and a fully fenced perimeter for ultimate seclusion. The second level is home to a luxurious primary retreat with a gas fireplace, expansive walk-in closets, and a spa-like marble bath, alongside three additional en-suite bedrooms and a convenient laundry room. Versatility abounds on the finished third floor, which offers a dedicated office, family room, and a fifth bedroom, while the lower level provides a spacious gym or media room with integrated cabinetry. Ideally located just moments from award-winning schools, fine dining, and boutique shopping, with easy access to NYC and Boston, this home offers a masterclass in style, privacy, and convenience.

30 Elm Pl, New Canaan
$4,400,000
5 Beds ⋅ 6 Baths ⋅ 24152795 MLS
Tucked away on a quiet private cul-de-sac, 15 Waterbury Lane offers exceptional privacy on a beautiful one-acre property in the heart of Darien. This spacious residence features 5 bedrooms, 4 full bathrooms, and 2 half baths, with a thoughtful layout ideal for both everyday living and entertaining. Generous living spaces provide flexibility for work, gathering, and relaxation, while well-sized bedrooms offer comfort and retreat. Enjoy the rare combination of a peaceful, secluded setting with excellent proximity to Darien's highly regarded public schools, making this home a standout opportunity for those seeking space, privacy, and convenience.

15 Waterbury Ln, Darien
$4,362,500
5 Beds ⋅ 6 Baths ⋅ 24153851 MLS
One of New Canaan's distinguished landmark residences, this extraordinary home is gracefully sited on 2.6 acres of sweeping lawns and mature trees along coveted West Road, just under a mile from the village.A meticulous expansion and renovation have reimagined this home for modern living, while honoring the timeless elegance and architectural integrity of the original home. Sun-filled, graciously scaled interiors unfold through a series of beautifully proportioned rooms, where french doors throughout open seamlessly to an expansive bluestone terraces and the park-like grounds beyond.The residence offers five bedrooms and four newly renovated full baths, including a light-filled primary suite with private sitting room and walk-in closet.The ground floor features a stunning Great Room, a front to back living room, an elegant dining room and a beautifully refreshed chef's kitchen that opens to a light-filled breakfast room with its own private stone terrace. An expansive family room, framed by walls of windows, captures sweeping views of the landscape. Completing the first floor plan is a new bright and sunny laundry room, two beautifully appointed half baths and a thoughtfully designed mudroom leading to a brand-new second-floor home gym.The third floor boats a private home office and another bedroom suite with full bath. A truly rare and incomparable offering, combining vintage charm, modern luxury, and an exceptional West Road location; ready for the most discerning buyer.

32 West Rd, New Canaan
$4,350,000
6 Beds ⋅ 6 Baths ⋅ 24184857 MLS
Perfectly positioned in the heart of town & just a short walk from train, park and schools, Douglas Road is an extraordinary home built by Cognetta Homes. Thoughtfully designed to blend timeless craftsmanship with modern luxury. Offering over 7000 sq. ft. on four beautifully finished levels, this stunning residence features 6 bedrooms, 6 baths & a light-filled floor plan that seamlessly connects elegant interior spaces with outdoor living. Designed for both sophisticated entertaining & comfortable everyday living, the home showcases premium finishes, generous proportions with meticulous attention to detail throughout. At the heart of the home is a spectacular chef's kitchen featuring Wolf and Sub-Zero appliances, custom cabinetry, a spacious walk-in pantry & an adjoining dining area complete with a butler's station & wine bar. A dramatic floating staircase serves as a striking architectural focal point, while the glass-enclosed office provides an inspiring, private workspace. The luxurious primary suite offers a true retreat, highlighted by a spa-inspired bath with radiant heated floors. Abundance of light with impressing soaring ceilings on the third level & a finished lower level featureing a gym, spacious game room, lounge area, a private bedroom with full bath-ideal for guests, a home office & a playroom creating the perfect space for an au pair, or a sixth bedroom. One of a kind, luxury home in one of the area's most desirable locations with sidewalks to town and school

148 Douglas Rd, New Canaan
$4,350,000
5 Beds ⋅ 6 Baths ⋅ 24157816 MLS
Situated proudly on a knoll near the center of town, this beautifully crafted Nantucket-style Colonial blends timeless grandeur with effortless livability. A gracious front-to-back foyer welcomes guests and draws the eye upward to the belvedere, a hidden nook where sunlight pours in and creates a dramatic entrance. The library is wrapped in floor-to-ceiling bookshelves, creating an intimate space to read beside the fireplace, enjoy a drink from the wet bar or relax on the adjoining covered patio. The dining room, centered around a grand fireplace, is equally striking and complemented by a butler's pantry with wet bar for seamless entertaining. At the heart of the home, the well-appointed chef's kitchen features an expansive island with seating for five and opens to a great room, where a fireplace and sunlit dining area create a natural gathering place while opening up to the backyard patio for easy entertaining. Bathed in afternoon light, the formal living room is an elegant setting for fireside conversation and quiet relaxation. Upstairs, a thoughtfully designed office with built-in desks leads to 4 ensuite bedrooms, a huge rec room, laundry facilities and a gracious primary suite, complete with a sitting area, fireplace, dressing room and 2 primary baths for refined tranquility. An oversized three car garage has masterfully designed storage while an expansive unfinished basement offers abundant space and possibilities...all just steps from town, dining, and shopping.

44 Andrews Dr, Darien
$4,315,000
5 Beds ⋅ 7 Baths ⋅ 24148496 MLS
Welcome to 28 Crooked Mile Road! Privately sited at the end of a quiet cul-de-sac in North Darien on a private road in the Ox Ridge school district, this handsome cedar shingle-clad colonial sits on two beautifully manicured acres with mature trees and planting beds. The property offers wonderful western and southern exposure, the house is truly flooded with sunshine throughout the day. The home underwent a major renovation in 2007 and more recently, in 2020, the kitchen and bar area had a fabulous redo!. The classic shaker style kitchen shares an adjacent family room with a fireplace and access to the patio beyond. Formal living and dining rooms and an office anchor the first floor, along with a magazine worthy, newly renovated sunroom (complete with wet bar)! The second floor holds 5 bedrooms. Four are en-suite and positioned along the south side of the house, while a 5th (and potential 6th) bedroom sit on the North side - well suited for guests, older children or an au pair. Also, up the back stairs, is a generous bonus room, perfect for any number of activities! In 2025 the entire roof was replaced, and an array of solar panels were installed on the rear of the home. An electric car charger in the 3-car garage and generator complete this very well-equipped house. Don't miss the chance to make this well maintained and beautifully updated colonial your forever home!

28 Crooked Mile Rd, Darien
$4,250,000
5 Beds ⋅ 6 Baths ⋅ 24179208 MLS
Perched on a sunny knoll overlooking two acres of beautifully landscaped grounds, this thoughtfully expanded center hall colonial in coveted Hoyt Farms is a rare find. Mature specimen trees of remarkable scale anchor the property, lending an established presence that simply cannot be replicated. Inside, a seamless expansion honors the home's colonial origins while adding the generous proportions that today's living demands - five bedrooms, six baths, and a layout configured for both practical family life and gracious entertaining. The pool area is the undisputed centerpiece; a stunning pool and separate spa set the stage for effortless gatherings, while a fully equipped outdoor kitchen and wood-fired pizza oven make it a natural destination from spring through fall. At this scale, on these grounds, in Hoyt Farms - 83 Long Lots is a genuinely special offering.

83 Long Lots Rd, New Canaan
$4,250,000
6 Beds ⋅ 7 Baths ⋅ 24179792 MLS
Exquisite 6-Bedroom Colonial on Over 3 Private Acres - This is the one you've been waiting for-a timeless estate designed for gracious living, exceptional entertaining, and the creation of lifelong memories. Set at the end of a private lane on over 3 spectacular acres, this exceptional Colonial blends timeless elegance with modern luxury. A grand foyer with a sweeping curved staircase welcomes you into beautifully scaled rooms featuring soaring ceilings, exquisite millwork, and abundant natural light. Formal living and dining rooms, each with a fireplace, flow seamlessly into an impressive library w/custom built-ins and a sun-filled family room w/French doors opening to an expansive terrace. The gourmet kitchen overlooks the pool and adjoins a charming paneled breakfast room with a fireplace, creating the perfect setting for everyday living and entertaining. Upstairs, a gracious landing overlooks the dramatic foyer and leads to a luxurious primary suite with fireplace, custom cabinetry, and a spa-inspired bath. Three additional en-suite bedrooms, a spacious bonus room, and a private guest suite provide exceptional flexibility. The fully finished walk-out lower level offers a large playroom, guest suite with full bath, and a dedicated fitness room. Outside, enjoy the private, park-like grounds complete with stone walls, a new pool, fenced yard, and playset. Just minutes from town, train, and award-winning schools, this rare offering combines privacy, scale, and convenience.

225 Marvin Ridge Rd, New Canaan
$4,250,000
5 Beds ⋅ 5 Baths ⋅ 24158599 MLS
This exceptional 5-bedroom, 41/2-bath Nantucket-style Colonial blends refined architecture with relaxed coastal living. Thoughtfully renovated in 2012 by Steven Mueller Architects LLC and refreshed by the current owners in 2021, the home welcomes you with a dramatic two-story foyer and beautifully designed interiors filled with natural light. Crisp millwork, shiplap detailing, coffered ceilings, and custom built-ins create a timeless backdrop throughout. The elegant yet inviting living spaces include a serene living room centered around a sleek fireplace with symmetrical built-ins and wide-plank floors, ideal for both everyday living and entertaining. Water views from many rooms enhance the home's peaceful coastal setting, filling the interiors with light and openness. Outdoors, elegant bluestone patios, an elevated second-floor deck positioned for sunset views, and professionally landscaped grounds overlook the scenic Five Mile River-an idyllic setting for both quiet moments and memorable gatherings.

90 Five Mile River Rd, Darien
$4,200,000
5 Beds ⋅ 7 Baths ⋅ 24185083 MLS
A Masterpiece of Colonial Elegance and Resort-Style Living on Dunning Road - Perfectly positioned on a coveted cul-de-sac just moments from town on 2 perfectly flat acres, this stately 5-bedroom, 6.5-bath center hall colonial offers an unparalleled blend of sophisticated design and private resort living. Inside, the formal living room sets a dramatic tone with its stately fireplace and a breathtaking wall of windows framing views of the lushly landscaped backyard oasis, while a separate, sun-drenched solarium provides a tranquil and private retreat for quiet relaxation. The heart of the home is a designer kitchen equipped with professional-grade appliances, a massive center island, a walk-in pantry, and an adjacent breakfast room and separate command center-all seamlessly connecting to a formal dining room and opening through floor-to-ceiling glass French doors to the pool and cabana. For everyday gathering, a separate family room features custom built-ins and its own fireplace, complemented by an expansive finished lower level that boasts a third fireplace and endless recreation space. Outside, the property transforms into a premier entertainment venue, complete with a sparkling pool, a rare 2-room/2-bath cabana, and a private tennis court, making this exceptional estate a true sanctuary for modern living.

67 Dunning Rd, New Canaan
$4,200,000
5 Beds ⋅ 5 Baths ⋅ 24165314 MLS
The moment you step onto the inviting front porch, you'll feel the warmth and charm of this exceptional 5-bedroom, 4.5-bath Colonial perched on a quiet cul-de-sac. Experience sophisticated design, unparalleled comfort, and an unbeatable location. Welcome to your dream home in Darien. The heart of the home is the chef's kitchen, fully renovated and featuring top-of-the-line appliances, a leathered black quartz island, and space for everyone to gather. Flowing through french doors to the spacious family room, adorned with custom built-ins and the sun-drenched playroom that opens to the professionally landscaped backyard and terrace-your private oasis for outdoor living. Upstairs, the luxurious primary suite is a true retreat, boasting a cozy fireplace, an expansive walk-in closet, and a spa-inspired bathroom with a double vanity, oversized shower, and a classic clawfoot tub. The additional 4 bedrooms all gift generous size, oversized closets and 3 more fully renovated bathrooms. The great room wows with size and soaring exposed beams, a striking stone fireplace. A fun, warm and inviting spacee for all to enjoy. Don't forget the basement with finished space, workout area and a hockey shooting room. Situated just minutes from school, the train, parks, downtown shops, and acclaimed restaurants, this property offers luxury living along with convenience and a true sense of community.

2 Roland Dr, Darien
$4,100,000
5 Beds ⋅ 7 Baths ⋅ 24149920 MLS
Experience the perfect synergy of classic New England charm and forward-thinking design in this stunning 2024 renovated and expanded Colonial. At the heart of the home, a sun-drenched chef's kitchen with a cozy stone fireplace flows seamlessly into living spaces anchored by dual staircases and a family room featuring bespoke built-ins with window seats, a wet bar, and French doors leading to a vaulted sunroom. Retreat to a primary suite that rivals the finest boutique hotels, boasting a vaulted ceiling, private balcony, coffee station, and a spa-inspired wet room with a double shower. All bedrooms are en-suite with designer bathrooms and the flexible space of the billiards room or library offers space to suit any lifestyle. The finished lower level includes a bonus room and gym. Outside, your private oasis awaits with a brand-new 20x40 heated pool, stone terraces, and a premium grilling station nestled among lush, low-maintenance landscaping for total seclusion. Best of all, this home is powered for the future with solar panels providing energy independence and significant savings. Located just one mile from town and the train, this turn-key sanctuary offers a rare, eco-conscious lifestyle where casual entertaining meets high-end formal elegance.

295 Brushy Ridge Rd, New Canaan
$4,100,000
5 Beds ⋅ 6 Baths ⋅ 24041510 MLS
Built in 1885 as a Gilded Age summer retreat, Rock Gate is as well-known and celebrated in Washington as its architect: Ehrick Rossiter. Rossiter's generous rooms graced with restored carved butternut wood panels, walnut and fir floors, delicate turned spindles, alongside arched windows, porches, and turreted and gable roofs, define the Queen Anne shingle-style homes of the period. Updated and reconfigured for the 21st century, this magnificent home contains modern comforts without sacrificing historical significance and charm. Bathed in natural light, the kitchen invites cooking & conversation; a spacious mudroom with built-ins summons summer strolls; and a remodeled primary bath leads to a dressing room that suggests elegant ease. Reinvigoration of the interior also includes fresh paint, stylish wallpaper, and new carpeting. Ten fireplaces grace the 5-6 bedroom home that boasts 5 full baths, 1 powder room, a wine cave, and wide staircases. New boilers, hot water tanks, plumbing, lighting controls, chimney liners, a well pump and water treatment system, and new equipment for the heated gunite saltwater pool aid effortless living. In addition to a new 1-bay detached garage, a separate 3-bay garage with a large walk up loft awaits your vision. Understated landscaping compliments the outcropping of stones for which the house was named, and grounds are enhanced by stone pathways trimmed with greenery. A private rear terrace sits amid a nest of trees that embraces the property.

51 Ferry Bridge Rd, Washington
$4,000,000
5 Beds ⋅ 5 Baths ⋅ 24183935 MLS
Set on a beautifully manicured one-acre lot, this home welcomes you w/ soaring 9-foot coffered ceilings and a fabulous flow w/ bright, open, spacious rooms and wonderful natural sunlight, making every room feel both generous and livable. The heart of the home is a large gourmet kitchen featuring marble countertops, stainless steel appliances, and a center island, ideal for gatherings and everyday living. The kitchen opens to a casual dining space and a spacious family room w/ a fireplace. A formal living room, formal dining room w/ French doors, mudroom w/ great storage, powder room, and access to the 3-car garage, with ceiling height designed to accommodate double stacking for up to 6 vehicles, complete the main level. Step outside from the kitchen to a private deck overlooking an expansive yard w/ mature plantings and a separate outdoor firepit space, perfect for hosting friends or enjoying quiet evenings under the stars. Upstairs, the luxurious primary suite is a true retreat, boasting an expansive walk-in closet, his and hers spa-inspired bathrooms with a double marble-topped vanity, oversized shower, and a classic soaking tub, plus room for a private sitting area. 4 add'l bedrooms w/ great closets and a laundry room round out the second floor. As a bonus, an additional 1,000 square feet in the exceptional finished basement offers a second family room, home gym, and private office. Beyond the home itself, the location is second to none.

16 Overbrook Ln, Darien
$4,000,000
5 Beds ⋅ 5 Baths ⋅ 24165890 MLS
Gracious and light-filled, this stunning 5200 sq ft. classic, located on coveted Kimberly Place, offers the best of in-town living! This home has four fully finished floors, high ceilings, detailed millwork, hardwood floors, versatile floor plan, and lovely private rear yard with expansive terrace. This five bedroom, four full and one half bath home offers a gorgeous new custom-built kitchen with high end appliances, large island, and dining area that opens into a fabulous family room with fireplace and built-ins. The spacious, newly renovated lower level with full bath, has endless possibilities for play, exercise and work. Additional improvements include new cedar roof, copper gutters, complete painting of interior and exterior, new cedar fencing, and so much more. This desirable location offers a short walk to town and the New Canaan train station!

7 Kimberly Pl, New Canaan
$3,950,000
4 Beds ⋅ 4 Baths ⋅ 24146586 MLS
A Unique Opportunity! Sail Harbour Club, on Candlewood Lake, showcases this Rare Waterfront Find! Completely level property w/west exposure,195 ft frontage, dock, beach, IG pool & spa, on a private 1.44 acs. The stunning open plan exudes a casual elegance.The vaulted great room has a floor to ceiling stone fireplace, hand hewn beams, new hardwoods & amazing views from walls of windows, overlooking an idyllic yard. The expansive kitchen w/a large island bar overlooks both dining room & kitchen eat-in area surrounded by windows & sliders, bringing the outdoors in. Granite counters tops, white wood cabinets, stainless appliances & new hardwood floors, ideal for gathering. Sliders lead to the bluestone, canopied patio & lush lawn to lake with new dock & lakeside beach. The main level owner's suite offers a private oasis, grand bath with double sinks, granite counters, frameless glass shower & even a bidet.Two oversized bedrooms with newly renovated full baths flank the vaulted loft/office, all with dynamic lake views. wide plank floors, tiled baths, abundant closet space & custom built-ins with quality details. A 23 x 24 bedroom over the garage serves as an ideal guest space or bunk room. Another full bath, in the main level mudroom offers easy access from yard & pool. The lower level is ready for media/game room & is equipped with a maids quarters/office. Extensive custom renovations make this a true lake find! SHC amenities include:tennis, pickleball, clubhouse, beach & marina!

8 Heritage Island Rd, New Fairfield
$3,925,000
5 Beds ⋅ 5 Baths ⋅ 24178118 MLS
Perfectly positioned in one of Darien's most coveted neighborhoods, 8 Sunset Road is the home you've been waiting for. This elegantly updated Colonial seamlessly blends timeless architecture with the ease of modern living. Spanning over 4,800 square feet, this five-bedroom, four-and-a-half-bath residence offers an exceptional floor plan suited for both entertaining and everyday comfort. The sun-filled first floor flows from a formal living room and gracious dining room into a chef's kitchen that opens effortlessly to a sunken family room with wood-burning fireplace, high ceilings, and custom built-ins. Upstairs, the primary suite provides a true retreat, while three additional bedrooms and two full baths offer space and flexibility for family and guests alike. Above the garage you'll find the fifth bedroom, complete with en suite full bath - the perfect flex space for work, exercise, guests, or all of the above! The finished lower level makes for the perfect play or bonus room, and provides ample storage. Outside, a beautifully landscaped yard frames a private patio with a fire pit, creating the perfect backdrop for al fresco evenings and roasting marshmallows. With schools, train, and town, just a stone's throw away, this is a rare opportunity on a truly special street.

8 Sunset Rd, Darien
$3,912,000
4 Beds ⋅ 5 Baths ⋅ 24160428 MLS
This gracious Colonial blends timeless 1930s charm with thoughtful modern updates, ideally located on one of Darien's most sought-after in-town streets, known for its traditions and strong sense of community. Set on a level, one-acre property in a coveted half-acre zone, the home offers rare expansion potential and exceptional lifestyle appeal.Extensively renovated and expanded, the home features a reimagined layout designed for today's living. The updated kitchen with custom cabinetry, granite countertops, and high-end appliances opens seamlessly to the family room with fireplace. A butler's pantry, walk-in pantry, mudroom, and dedicated home office add both functionality and convenience. A versatile room above the garage offers flexible living space, ideal as a fifth bedroom, guest retreat, or potential in-law suite. Recent improvements include renovated bathrooms and a luxurious primary suite with spa-like bath featuring heated floors, soaking tub, marble walk-in shower, and custom built-ins. Mechanical upgrades include multiple air handlers, updated HVAC systems, full-house generator, new boiler and hot water heater, and replaced roof & windows. Classic details such as original hardwood floors and elegant millwork preserve the home's character throughout. The private, level property is framed by mature plantings and features a thoughtfully designed patio-ideal for entertaining, recreation, or future expansion. A rare combination of location, land, community & charm

12 Sunset Rd, Darien

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.