Darien CT Real Estate & Homes for Sale

Welcome to this beautifully remodeled home in one of Darien's most sought-after neighborhoods, offering over 4,000 square feet of living space. This classic colonial has been thoughtfully updated twice, first in 2012 and again in 2022, where it was expanded and meticulously redesigned. The main floor features a spacious layout, perfect for both everyday living and entertaining. A stunning dining room with bay windows flows seamlessly into the newly renovated kitchen. The kitchen boasts a large island, a walk-in pantry, and a dedicated dining area, all with easy access to a cozy covered deck. The first floor also includes a charming formal living room, offering a warm space to unwind, a private office, and a fabulous family room off the kitchen. Upstairs, the master suite is a true retreat, featuring a beautifully renovated bathroom and a walk-in closet. Three additional generously sized bedrooms provide ample space for family and guests, complemented by a full, modern bathroom. The third floor offers a finished extra space, perfect for a playroom, home gym, or additional living area, while the fully finished walk-out lower level provides even more room for fun and hanging out! 6 Chester Road combines classic charm with tasteful updates, offering a perfect blend of comfort, style, and functionality.

Walk to train and town from this 4-bedroom sun filled home with soaring 9 foot ceilings and hardwood floors throughout. The generous entry foyer welcomes you to a spacious family room with beautiful moldings, an electric fireplace and sunlight galore! The formal dining room with gorgeous, detailed molding is great for holiday gatherings and is adjacent to the gourmet kitchen with a large island, lots of storage and access to the terrace and yard behind. The 4th bedroom/office is conveniently located on the first floor with a newly renovated full bath. Up the stairs the gracious primary suite boasts a large walk-in closet and a huge spa bath with soaking tub, private shower and double vanity. 2 additional sunny large bedrooms each with large custom-fitted closets and a lovely full bath complete the second floor. The lower level features a separate laundry room and a large rec room for active play and access to outdoors. A fully fenced back yard includes a large terrace for entertaining and a flat private yard for pooch and play. Walk to train/town in minutes. Convenient to everything, this amazing home with soaring ceilings won't last! Completely rebuilt in 2009

Welcome to 250 Tokeneke Road, a breathtaking 7,500 sq. ft. custom-built home that blends luxury, comfort, and convenience just minutes from Rowayton Village, the Corbin District, and downtown Darien. New construction at its finest! Step inside to soaring ceilings, exquisite millwork, and high-end finishes that create an elegant yet inviting atmosphere. The open-concept design seamlessly connects the gourmet kitchen-featuring top-tier appliances, custom cabinetry, and an oversized island-to the family room with a cozy fireplace. French doors open to a private backyard retreat, complete with a heated gunite pool and spa. The luxurious primary suite boasts a spa-like bath and a spacious walk-in closet, while five additional bedrooms provide ample comfort for family and guests. Enjoy a vibrant, walkable lifestyle just steps from the heart of Rowayton, where you can explore the farmers market, indulge in top-tier dining, and browse charming boutiques. With downtown Darien and Metro-North also just a five-minute drive away, you'll experience the best of both worlds. Schedule your private showing today!

Just Perfect! Nestled in the heart of the prestigious Tokeneke Association, 10 Winding Lane is a masterfully remodeled smart home, designed for effortless luxury and year-round comfort. Freshly painted and meticulously maintained, this turnkey 4-bedroom, 3 1/2-bath retreat blends timeless elegance with modern convenience. At the heart of the home, the gourmet DEANE-designed kitchen is a chef's dream, featuring premium appliances, marble countertops, a spacious island, and exquisite craftsmanship. French doors from both the kitchen and living room open to expansive deck and lushly landscaped gardens, creating a seamless indoor-outdoor connection. For year-round enjoyment, a three-season screened-in porch with a wood-burning fireplace offers the perfect setting-whether for crisp autumn evenings or breezy summer nights. Upstairs, the luxurious primary suite is a private sanctuary, complete with his-and-hers walk-in closets and a spa-inspired natural stone bath, featuring heated floors, a soaking tub and a spacious walk-in shower. Outside, a picturesque natural landscape and a charming stone pathway enhance the home's appeal. Move right in and embrace the unparalleled lifestyle of living in Tokeneke.

Welcome to 15 Allwood Road, an elegant Colonial residence that beautifully combines timeless charm with modern luxury. Set on a sprawling 2.54-acre lot within the private Allwood Association, this property is an opportunity you won't want to miss. Upon entering, you will be immediately captivated by the front-to-back foyer, sophisticated design, and thoughtful layout. The first level and upstairs bathrooms feature custom reclaimed antique wide plank wood floors. The gourmet kitchen stands as the heart of the home, complete with a spacious center island that is perfect for casual meals or hosting grand gatherings. High ceilings, sunlit rooms, cozy screened-in porch and four working fireplaces are just a few of the many highlights of this exceptional home. With six beautifully appointed bedrooms and five and a half bathrooms (including four ensuite), there is no shortage of space for comfort and privacy. The primary suite serves as a true sanctuary, offering a dressing area, a large walk-in closet, and a spacious bath. The finished basement adds an extra layer of luxury, featuring a 1,000-bottle wine cellar, a fully equipped gym, a playroom, a full bath, a cozy wood-burning fireplace, and plenty of storage space. 15 Allwood Road is not just a home; it represents a lifestyle. A perfect blend of elegance, comfort, and modern amenities awaits you!

Welcome to 10 Holly Lane, a custom modern Colonial built in 2019 by Fox Hill Builders nestled in one of Darien's most sought-after neighborhoods. This exquisite residence offers the perfect blend of elegance and comfort. Its 10' ceilings on the first floor allow natural light to stream throughout the home making it an ideal sanctuary for discerning homeowners. Boasting approximately 6,012 square feet of meticulously designed living space, this home features 5 generously sized bedrooms and 5 well-appointed en suite bathrooms with 2 half baths providing ample room for family and guests. Situated in a tranquil and prestigious area of Darien, the property offers peace and privacy while being part of a vibrant community. The home is conveniently located within walking distance to Darien HS and Middlesex Middle School, shopping centers, dining establishments, and recreational facilities. With easy access to major highways and public transportation, commuting to nearby cities is seamless. Experience the epitome of luxury living at 10 Holly Lane. This property is a testament to refined taste and thoughtful design, offering a lifestyle of unparalleled comfort and sophistication.

An exceptional and unique opportunity awaits - rarely, if ever, does land of this quality and location come to market! Dream, create and escape to your sanctuary with this breathtaking and flat 7.62-acre property nestled in coveted Darien, CT. Boasting 2.74 buildable acres, this one-of-a-kind parcel offers an unparalleled canvas to create your custom masterpiece. Imagine waking up to serene and panoramic vistas, entertaining like no one else can, and multiple generations playing in the natural and private landscape. Whether you envision a family compound, a minimalist retreat or a timeless country estate, this property offers endless possibilities to bring your architectural dreams to life. Located in one of Connecticut's most sought-after enclaves, you'll enjoy the perfect balance of tranquility and accessibility - one hour from Manhattan, and just minutes from the vibrant towns of Darien and New Canaan, top-rated schools, country and riding clubs, town beaches and the sparkling Long Island Sound. This is more than a property; it's an invitation to create your masterpiece and provide the landscape to build memories with family and friends. Don't just build a house - create a legacy on this extraordinary land. Your dream starts here.

Welcome to 2 Driftway, a stunning 5-bedroom, 8,239 sq. ft. New England Colonial set on 2 acres in Darien's sought-after Tokeneke neighborhood. Built with A+ construction and high-end European craftsmanship, this home features cathedral ceilings, a dramatic dining room with two-story windows and radiant floor heating, and 18+ foot vaulted ceilings in the formal living, and family rooms, flooding the space with natural light. Designed for year-round entertaining, the gourmet kitchen boasts a Sub-Zero refrigerator, Diva de Provence stove, Wolf convection wall oven, wine chiller, and water filtration system. The kitchen and family rooms share a dual-sided wood-burning fireplace, and a private office includes a dry bar. Upstairs, the primary suite offers a spa-like bath, sauna, and a large walk-in closet, alongside three generously sized bedrooms and a spacious playroom. The fifth bedroom provides exceptional privacy and could serve as an additional primary suite or ADU with its' own entrance. The home also includes a gym, an expansive basement ready to be partially finished, and a 3-car heated garage. Enjoy direct pond frontage, perfect for ice skating in winter and kayaking in summer. Just a short walk to downtown Darien, the train, schools, and The Tokeneke Beach Club. This home is a rare opportunity. Schedule your showing today!

HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom, seven-bathroom main house is adorned with exquisite millwork, high-end finishes, and six fireplaces. An infinity-edge pool overlooks one of two sandy beaches and the glittering waves, with the historic Greens Ledge Lighthouse in the distance. The island also includes a two-bedroom guest house, a pool house equipped with a kitchenette and full bathroom, a dock, separate spa and a freshwater pond. First Floor: The front-to-back foyer leads to a waterside veranda that spans the back of the house, inviting in the salty breezes. Walls of windows in the formal dining and living rooms, both featuring masonry fireplaces, offer stunning shoreline views over the extensive lawn. The paneled library, with veranda access, includes custom bookshelves, window seats, a wet bar, and a fireplace. A serene guest bedroom suite with a marble bathroom also has its own water views. The spacious chef's kitchen, featuring a coffered ceiling, includes a sunny breakfast room with a fireplace, a large butler's pantry, and a kitchen office. It adjoins the sun-filled family room, which has a fireplace and coffered ceiling. Ideal for summer dining, the family room opens to a screened-in porch with water views extending to Long Island. A stone terrace off the breakfast room, complete with an outdoor fireplace, built-in barbecue, spa and outdoor shower, serves as the hub for dining and entertainment from spring to fall. A mudroom with a full bathroom leads to a workshop and an attached three-car garage with a large playroom and exercise room above. Second Floor: Strategically positioned, the elegant primary suite opens to a spacious balcony, perfect for savoring sunrise views over the water. It also includes a luxurious marble bathroom with a soaking tub and two custom dressing rooms. This level also houses two additional en-suite bedrooms with splendid water views and a convenient laundry room. Third Floor: Resembling a ship captain's quarters, the bay-windowed office offers the highest vantage point in the house with its private balcony, showcasing dramatic views over the Long Island Sound. Completing this floor are two more en-suite bedrooms each with breathtaking water views. Guest House: Embracing the charm of a summer cottage, the guest house includes a fully-equipped kitchen with a breakfast area, a private office, a powder room, and a family room with a dining area and stone fireplace. The family room opens onto a stone terrace with outdoor fireplace that overlooks the serene backyard and the water of Ziegler Cove. Upstairs, there are two en-suite bedrooms and a laundry room. Protected by a rocky shoreline and shaded by mature trees on 18.15 acres, Hay Island is the ultimate private retreat. Two sandy beaches offer perfect spots for swimming, sunbathing, fishing, or launching kayaks, with a sheltered dock for further water adventures. The beachfront infinity pool with its own pool house enhances the resort-like experience for guests of all ages. Verdant lawns, a garden, a spring fed fresh water pond and winding pathways traverse the property, leading to private vantage points with spectacular water views in every direction. For those well-versed in luxury properties, this coastal retreat is a prime addition to any real estate portfolio.

HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom, seven-bathroom main house is adorned with exquisite millwork, high-end finishes, and six fireplaces. An infinity-edge pool overlooks one of two sandy beaches and the glittering waves, with the historic Greens Ledge Lighthouse in the distance. The island also includes a two-bedroom guest house, a pool house equipped with a kitchenette and full bathroom, a dock, separate spa and a freshwater pond. ELEVATIONS: Main House Door Sill Elevation is 19.38 Cottage Door Sill Elevation is 16.31 Pool House Door Sill Elevation is 14.68

Spacious and spotless! This is a private end unit condo at Darien Close in the heart of downtown Darien. Walk to shops,restaurants and Tilley Park. The unit is full of light in every room. It's all freshly painted and baths have been updated with new vanities and showers.This is an open floor plan with two story ceilings in every room. There is new carpet in the bedrooms,a new oven and new flooring throughout. The living room sliding doors lead to a private,enclosed area with a bluestone patio. Home includes electric car charging station in the garage.

PRICE IMPROVEMENT. Stunning Colonial. Enjoy low-maintenance living in a spacious, custom-built home on one of Darien's most sought-after streets.7 bedrooms and 6 fulls baths all with detailed millwork make this elegant home an exceptional find. The open, light-filled kitchen with a center island is the heart of the main floor, effortlessly flowing into the gracious family room on one side and a charming breakfast nook on the other. The formal dining room is also attached to the kitchen through the butlers pantry, ideal for entertaining. The formal living room with coffered ceilings and hardwood herringbone floors leads to a flexible space for either a home office or main floor bedroom, as well as a full bath. The second floor boasts four large bedrooms and three full baths, while the third floor has a generous guest suite and open playroom with vaulted ceilings. An additional 544 square feet of finished, walk-out basement space has a full bath and a bedroom or home gym, as well as a play area. The attached, 2-car garage and copious storage complete the expansive home. Beautifully choreographed seasonal plantings from a renowned landscape design company add a 3-season burst of color to the yard, where the bluestone patio offers a perfect outdoor dining place. Close proximity to beach, train, and the new Darien Commons development make 15 Gardiner Street the ideal location for enjoying Darien's top amenities.

Premier Darien Waterfront Residence on Contentment Island Road, in the private Tokeneke Association! This exquisitely renovated estate seamlessly blends classic beauty with modern amenities, catering to the desires of today's discerning homebuyers. This property boasts abundant space, featuring direct water access complemented by a private dock and moorings, as well as a charming guest house, nestled within its expansive two acre grounds. Features include: 7 fireplaces, heart of pine flooring, and 9+ ceilings throughout. The Main Level boasts spacious open living areas with direct views of the water, gourmet Chef's Kitchen and Family Room, custom Library, lovely Living Room, Dining Room with beautiful coffered ceiling, and a stunning Sunroom with panoramic water views. The Second floor offers: 4 large Bedrooms and three Full Baths with direct water views, including a Primary suite with a lovely Sitting Room/Office. The Third Floor includes a large Media room, an additional Bedroom, two Bonus Rooms (Gym and Office) and a Full Bath. Minutes to downtown Darien, Rowayton, shops, restaurants, trains, and Award Winning Schools! A rare opportunity for coastal living just 40 miles from NYC. Also, enjoy outstanding evening sunsets!

Home by the Sea is set majestically behind stone pillars and gates on one of the largest Long Neck Point parcels, affording its residents 3.2 landscaped acres of privacy. As you enter, the peaceful setting of the secluded cove takes your breath away. There are wrap-around decks, velvet lawns, flowering gardens and water views for miles. Nature lovers will be in Heaven. The acclaimed architect Sean O'Kane and esteemed builder Hobbs, Inc, who took 2 years to complete the residence, were awarded the most prestigious CT Home Builders (HOBI) award for Best Custom Home. There are 12K sq.ft. of finished space on four floors. Formal and informal living spaces of detailed craftsmanship and millwork are absolute perfection for family and friends. All bedrooms are ensuite, including the Zen-like primary w/fireplace, private deck, 2 walk-in closets and 5 star hotel-like bath. An oversized domed room w/beams and full bath over the four car garage is an ideal WFH setting or an incredible in-law/nanny quarters. The home offers state of the art lighting and technology, a dock for your boat, a lower level w/theatre, wine cellar, gym, billiards room w/mahogany bar, and sunroom. There's even an area to wash your pooch. The pool area is gorgeous with ample patio areas. Home by the Sea represents an opportunity for the savvy, as homes of this quality and premier location rarely come on the market.

This stunning custom-designed waterfront shingle-style home, built from the ground up in 2013, sits on 1.03 acres in the highly sought-after Noroton Bay neighborhood. Located on a quiet cul-de-sac, this exceptional property offers deeded access to a private beach, mooring field, clubhouse, snack bar, pier, and dock. The 7,600 sq. ft. residence boasts 6 bedrooms and 6.5 baths, all filled with natural light through expansive windows. The beautifully designed kitchen by Kitchens by Deane features high-end appliances, including a 42-inch Sub-Zero refrigerator, a 48-inch Wolf Range, and additional Sub-Zero refrigeration drawers. A bar area with a Sub-Zero wine fridge, refrigerator drawers, and a dishwasher makes entertaining effortless. The home's open layout flows seamlessly onto 1,700 sq. ft. of covered porches, perfect for indoor-outdoor gatherings. A wood-burning fireplace anchors the spacious living room, while hardwood floors extend throughout all levels, including the third floor. Outside, the professionally landscaped lawn leads to a private dock overlooking a serene pond with wildlife and views of Long Island Sound. With additional bonus rooms and exceptional craftsmanship throughout, this is coastal living at its finest.

Oversize 5+ acre lot with charming home in 2 acre zone. Home features a 1st floor primary suite and adjacent solarium. Gracious living room with large fireplace, home office with fireplace, formal dining room and step down sun room/family room opens to the terrace and swimming pool. Mud room with laundry and powder room as well as rear entrance from the pool sits adjacent to the cooks kitchen. Upstairs are 3 additional bedrooms and hall bath. The adjacent 2 level barn can be finished to complement the home as you wish. A party barn, artist studio, fitness area could nicely fit.

Sweet and Petite! Move to a private road in desirable Darien... Easy one level living includes updated appliances. Large sliders in kitchen open to fenced rear yard with storage shed. This is a marvelous alternative to restrictive condominium living so bring your pets! Enjoy "as is" or expand and grow your home on this double lot in the popular Noroton Heights area. Around the corner is Darien Commons where there's an array of fine shops and eateries. It's just steps to the Noroton station with express trains to NYC. The Darien lifestyle offers award winning schools, scenic beaches, gourmet dining and much more. This is a rare opportunity so come visit soon!

Proposed site plan and new construction drawings by Hatley Homes Design. Are you looking for a private, waterfront haven to build your dream home? Look no further than 1 Pratt Island. This 1 acre property is at the end of a private association with sunrise and sunset views. The lot comes with easements to a deep water dock and an incredible sandy beach steps away. With gorgeous mature trees, this property overlooks Darien Harbor in one direction and Stamford's Shippan Point in the other. Come find your paradise! Taxes will be calculated once property has been subdivided.

World class one of a kind newly constructed modern masterpiece designed by award winning architect Vita Design with stunning unobstructed water views from every room in the house. This custom coastal build sets luxury to the highest level. The home features tall ceilings with an abundance of open space filled with natural light coming in through the floor to ceiling oversized European style windows. The home was thoughtfully designed to form an effortless flow between indoor and outdoor living. Intimately private, yet close to all the great amenities of Darien and Rowayton town center and a convenient drive or train ride to New York City. Set on a spacious 1 acre lot with a pool this home is the perfect setting for coastal living. The master suite has its own scenic balcony where you can wake up to your own amazing ocean views. The gourmet kitchen and exquisite bathrooms are all fitted with carefully designed, high end finishes. The home feature all bedrooms with ensuite baths, home office, dining room, mud room, and a basement with space for a recreation room and bar. This luxury modern property reflects the best Darien has to offer in an amazing seashore oasis.

This newly constructed Nantucket-Style Colonial, exudes timeless elegance. The 6 bedroom and 6.2 bathroom home is meticulously designed with high-end finishes and exquisite millwork throughout. An impressive 3-story foyer anchors the expansive main level as formal living and dining rooms seamlessly flow to the family room and gourmet kitchen. While French doors lead to a patio overlooking the heated pool and spa. With a luxurious primary suite, and 5 additional bedrooms with en-suite baths, there is abundant living space. A bonus room with loft and a partially finished lower level add further versatility. Situated on 2.99 park-like acres, conveniently located to downtown Darien, this property is ready for its new owners to call it home!

Combining refined elegance with complete privacy, this 9.5-acre estate is the quintessential sanctuary for those seeking an elevated, sophisticated lifestyle in a tranquil and secluded setting. Situated at the end of a gravel drive lined with Bradford Pear trees, the compound features a 10,000-square-foot main house, a luxurious pool and pool house, a charming two-bedroom guest cottage, and an exceptional field house that truly takes your breath away. Renowned architect Louise Brooks has seamlessly blended the main home's historic charm with sleek, contemporary living spaces designed for modern needs. Positioned below the main house, the Brooks-designed field house offers a versatile space for casual recreation and entertainment. Highlights include an indoor batting cage with retractable steel windows, a two-lane bowling alley, and a resistance pool, all complemented by stylish social areas crafted for relaxation and enjoyment. Merging classic American style with cutting-edge design, 856 Hollow Tree Ridge Road is a home run for anyone who loves to entertain.

Nestled within the prestigious Tokeneke Association, this exceptional modern farmhouse is a masterpiece of design, offering a luxurious lifestyle on a grand scale. Boasting 9872 square feet of exquisitely crafted living space, this architectural gem seamlessly combines the timeless charm of a farmhouse with the sophistication of modern luxury. Upon entering, you are greeted by an impressive foyer with soaring ceilings, setting the tone for the grandeur that awaits within. The home features wonderful living space including four finished floors. Entertaining is a delight in the thoughtfully designed easy flow including spacious light filled rooms with 10 foot ceilings creating a wonderful ambiance for daily life and gatherings. The heart of the home, the gorgeous white and light wood kitchen, is a culinary dream featuring top-of-the-line appliances, custom cabinetry, butlers pantry and a generous island, perfect for family meals and large parties. The home offers 6 bedrooms and 7.5 baths, each meticulously designed to offer a blend of comfort and easy living. The primary suite is a private retreat, complete with a spa-like bath and expansive walk-in closets. The allure of this property extends beyond the interior, as the home sits on 2 acres of lush, manicured grounds, providing a serene and private oasis. A sparkling pool invites relaxation on warm summer days, while the expansive outdoor area offers ample space for al fresco dining and entertaining. Do not miss this one!