Darien Real Estate

Welcome to Darien, Connecticut, a picturesque coastal town nestled in the heart of Fairfield County. Known for its stunning waterfront views and charming New England ambiance, Darien offers a perfect blend of suburban tranquility and vibrant community life. With a population of around 20,000 residents, this town is renowned for its exceptional schools, making it a prime location for families seeking a nurturing environment for their children.

Darien boasts a rich history, reflected in its beautifully preserved architecture and quaint downtown area. Here, you’ll find an array of boutique shops, delightful cafes, and fine dining establishments that cater to every palate. The town’s proximity to Long Island Sound means that outdoor enthusiasts can indulge in a variety of activities, from sailing and fishing to enjoying leisurely walks along the scenic shores.

For those commuting to New York City, Darien offers convenient access via the Metro-North Railroad, making it an ideal choice for professionals seeking a peaceful retreat from the hustle and bustle of urban life. The community is also home to numerous parks and recreational facilities, providing ample opportunities for outdoor activities, including hiking, biking, and picnicking.

In addition to its natural beauty and community spirit, Darien hosts various events throughout the year, fostering a strong sense of belonging among its residents. From summer concerts in the park to festive holiday celebrations, there’s always something happening in this vibrant town.

Discover the charm of Darien, where picturesque landscapes meet a welcoming community, and find your dream home in this idyllic Connecticut gem!

Newest Listings in Darien

$5,650,000

6 Beds ⋅ 6 Baths ⋅ 24210704 MLS

A rare opportunity for high-end new construction in the Tokeneke School district, 237 Tokeneke Road features a custom design by the immensely talented Nick Demaio of Demaio Design Group. Set on an exceptionally private, elevated lot, the home offers four floors of light-filled living with a thoughtful, functional layout. A grand foyer opens to a direct sightline into the expansive chef's kitchen. To the left of the entry is a cozy living room that flows into the formal dining room and ultimately back to the kitchen, creating an effortless connection for entertaining. A bar and butler's pantry complement the kitchen/ dining room spaces. A very large family room and dedicated office (one of two in the home) complete the main floor. There are 4 bedrooms on the second floor, including a primary suite with a spacious private bath and his and hers walk-in closets. The second bedroom has a private en suite bath, and the remaining 2 bedrooms sharing a Jack-and-Jill bath. The third floor offers flexible space, customizable based on your needs; the current design plan has a bedroom, full bath and second office space. The lower level is not to be missed. There is a 2 car garage with direct access to a very large mudroom, a guest bedroom and full bathroom, and large recreation room. Private, bright and beautifully designed, this custom home pairs generous living spaces with versatility on every level.

237 Tokeneke Rd, Darien

$1,795,000

4 Beds ⋅ 2 Baths ⋅ 24210835 MLS

Step into a storybook setting at 150 Holmes Avenue, where the timeless elegance of a classic Victorian meets a meticulous, top-to-bottom modernization. From the moment you approach you'll feel the historic charm that defines this Darien gem. Inside, the transformation is striking. The entire interior has been freshly painted in a crisp, sophisticated palette, perfectly complementing the hardwood floors throughout. The heart of the home is a beautifully updated kitchen, blending contemporary convenience with the home's original soulful character. Every corner of this residence shines with pride of ownership; it is exceptionally clean, bright, and truly move-in ready. Whether you are hosting a formal dinner or enjoying a quiet morning in the sun-drenched living spaces, the atmosphere is one of effortless grace. Beyond the main house, discover a feature that sets this property apart: a detached two-car garage designed for the serious hobbyist. Equipped with a professional grade industrial hook and hoist system for engine work, this space is a dream come true for car enthusiasts or anyone needing a heavy duty workshop. It's a rare find that adds a layer of practical luxury to this enchanting estate. Experience the perfect blend of 19th-century personality and 21st-century peace of mind. Walking neighborhood, including to school and the train. Top of the line efficient mechanicals including a Buderus Oil Burner. Quality, comfort and convenience. Your new chapter starts here..

150 Holmes Ave, Darien

$3,795,000

4 Beds ⋅ 5 Baths ⋅ 24210059 MLS

Set within Darien's coveted private Tokeneke Association, 5 Cross Road is a quintessential stone Colonial gracefully positioned on a private .70 acre property. Timeless architectural character, exceptional privacy, and inviting living spaces define this distinctive residence in one of the town's most sought-after coastal neighborhoods.The thoughtfully updated kitchen serves as the heart of the home, while an extraordinary family room with soaring ceilings and abundant natural light offers a dramatic yet welcoming setting for everyday living and entertaining. A desirable first-floor primary suite provides comfort and convenience, creating an ideal layout for modern living. Classic details and generous rooms throughout complement the home's enduring stone facade and beautifully secluded grounds. Enjoy the rare combination of a tranquil residential setting, private association lifestyle, and convenient access to Darien's village, schools, train, beaches, and waterfront. A special Tokeneke offering where classic New England charm meets effortless, refined living.

5 Cross Rd, Darien

$2,200,000

5 Beds ⋅ 4 Baths ⋅ 24209736 MLS

Welcome to your private urban oasis. This meticulously updated home seamlessly blends sleek, contemporary design with massive, functional spaces. Property Highlights: Expansive Space: Enjoy 4,600 square feet of freshly renovated interior space. Modern Design: Features an open-concept layout outfitted with high-end, premium finishes. Storage: Includes a massive attic for all your extra storage needs. Prime Location While the property itself is engineered for exceptional privacy and quiet relaxation, you are only steps away from local conveniences: Downtown Dining: Vibrant restaurants and entertainment are just around the corner. Family Friendly: Located within short walking distance to the local elementary school. Commuter's Dream: Quick, easy access to the nearby train station.

13 Silver Lakes Dr, Darien

$3,995,000

24209317 MLS

Opportunities to build fresh on Long Neck Point are vanishingly rare, making this lush, one-acre parcel a true crown jewel in Darien's most prestigious enclave. This isn't just a piece of land; it's a seamless path to an extraordinary lifestyle. If you've been dreaming of a bespoke estate but dread the years of red tape, your solution has arrived. The property comes with preapproved architectural plans for a stunning Center Hall Colonial. The design features 7,500 square feet of sophisticated living space across the first and second floors alone, with additional square footage thoughtfully planned for both the third floor and the expansive basement level. Imagine sweeping interiors and a layout that flows effortlessly from one sun-drenched room to the next. With all permits in place and a premier builder ready to break ground, you can bypass the typical delays and start construction immediately. The lot itself is absolutely gorgeous, offering a level, expansive canvas that invites creative landscape design. Elevating this opportunity even further is the exclusive inclusion of waterfront access. A shared dock is currently being built for the four properties in this enclave, reachable via a dedicated pathway that leads directly to the water at Pear Tree Point Road. It is the ultimate amenity for those who wish to embrace the coastal lifestyle. This is a rare invitation to secure a foothold in a legendary location without the wait.

74 Long Neck Point Rd, Darien

$850,000

24207966 MLS

A unique opportunity for builders, investors, or those looking to create a home of their own in Darien. This .20-acre parcel offers the potential to build in a sought-after location convenient to schools, shopping, restaurants, major highways, and all that Darien has to offer. Bring your builder or bring your vision and create a home that is uniquely yours. Buyers are encouraged to conduct their own due diligence regarding zoning, building requirements, approvals, and regulations.

69 Hecker Ave, Darien

$16,495,000

10 Beds ⋅ 12 Baths ⋅ 24186570 MLS

Set on 2.93 private acres along coveted Long Neck Point, this extraordinary waterfront Colonial offers a rare combination of sweeping water views, privacy, and direct access to the water. Spanning more than 10,000 square feet, the residence is designed to embrace its spectacular setting, with expansive living spaces and breathtaking vistas from nearly every room. The eight-bedroom main residence features seven full and three half baths, eight fireplaces, and an effortless flow between gracious entertaining spaces and comfortable everyday living. A pool and private dock extend the experience outdoors, creating an idyllic setting for waterfront living and entertaining. A charming two-bedroom, two-bath guest cottage offers additional space and privacy for family and guests. Distinguished by its scale, setting, and direct water access, this remarkable Long Neck Point estate offers a rare opportunity to experience the quintessential coastal lifestyle.

155 Long Neck Point Rd, Darien

$3,600,000

5 Beds ⋅ 5 Baths ⋅ 24182550 MLS

Welcome to this beautifully maintained 1994 Colonial, perfectly situated on a premier, flat, dry acre at the end of a quiet, Private Cul-de-Sac. The experience begins the moment you turn down the picturesque driveway, offering a beautiful approach and an immediate sense of privacy upon arrival. Boasting 4,423 square feet of above-grade living space, this home is bathed in incredible natural light throughout. The thoughtfully designed layout features 5 spacious bedrooms and 4.5 well-appointed baths, offering plenty of room for family and guests alike. The heart of the home provides a seamless flow and an incredible space for entertaining friends and family, whether hosting formal dinners or casual weekend gatherings. A massive, versatile bonus recreation room sits privately over the 3-car garage-perfect for a playroom, media center, home gym, or an expansive home office. Step outside to enjoy the sprawling, level backyard, a rare find that offers endless possibilities for outdoor fun, gardening, or relaxation. Impeccably cared for - freshly painted inside and out and ready for its next chapter, this exceptional Darien property is just waiting for its new owners to move in and start making memories. Turnkey convenience meets timeless elegance in an unbeatable location!

18 Bates Farm Ln, Darien

$1,895,000

4 Beds ⋅ 3 Baths ⋅ 24206839 MLS

Charming bungalow-style home offering easy one-floor living, abundant natural light, high ceilings and character throughout. A welcoming front porch sets the tone, while freshly painted interiors provide a bright, fresh backdrop. The spacious great room features a striking stone fireplace, built-in bookcases and generous proportions for everyday living and entertaining. The kitchen enjoys views across the expansive, level backyard, and three bedrooms and two full baths complete the main level. The walk-out lower level adds exceptional flexibility with a family room featuring French doors opening directly to the patio, plus an additional bedroom and full bath. Turn-key and ready to enjoy today, the home also offers exciting expansion potential and flexibility to grow over time. A standout feature is the convenient location-just a short walk to Noroton Heights shopping, restaurants, amenities and train station, as well as Middlesex Middle School and Darien High School. An extensive network of neighborhood streets offers additional opportunities for walking and outdoor activity. A place to call HOME!

13 Chestnut St, Darien

$1,200,000

3 Beds ⋅ 2 Baths ⋅ 24205494 MLS

Move right in to this delightful cape style home offering effortless and modern upgrades on a private, fully fenced lot in prime Darien. Highlights include classic hardwood floors, a bright living room, a main-level bedroom, a den/office and two completely renovated full baths-one on each floor. The window lined dining room features a skylight and direct access to the deck which is perfect for entertaining. The second level boasts two flexible bedrooms with built-in storage and the second, completely renovated, full bath. The partially finished lower level offers a finished room which is currently used as a TV room, new washer and dryer, updated mechanicals, tankless hot water system and plenty of room for storage. This home is conveniently located minutes from downtown Darien, schools, restaurants and train stations.

145 West Ave, Darien

$3,925,000

4 Beds ⋅ 4 Baths ⋅ 24204574 MLS

Welcome to 20 Lighthouse Way, where coming home means stepping straight into a waterfront lifestyle. With a private boat mooring and the Long Island Sound at your doorstep, the transition from the workday to the water is effortless. Launch a paddleboard for a sunset outing, hop in a kayak, take the boat out for a spontaneous cruise, or enjoy waterskiing-all from your own backyard. Here, the best part of the day may be what happens after you get home. The heart of the home is a newly renovated, crisp white kitchen that flows effortlessly into a sun-drenched dining area and spacious family room centered around a cozy fireplace. Whether hosting a summer soiree or enjoying a quiet morning coffee, the open floor plan feels airy and intuitive. For those who need space to spread out, the first floor is versatile, featuring a bright living room with fireplace, dedicated office, oversized playroom, and functional mudroom with ample storage to keep coastal life organized. Upstairs, the primary suite and a second bedroom offer breathtaking water views, serving as private sanctuaries to watch the sun sparkle on the water. With four bedrooms and three updated baths, there is ample space, plus the flexibility to easily convert back to a five-bedroom layout. Outdoor living is elevated here-literally. Expansive decks on both levels overlook the water, providing the ultimate backdrop for alfresco dining and family gatherings.

20 Lighthouse Way, Darien

$5,995,000

6 Beds ⋅ 9 Baths ⋅ 24191678 MLS

Privately set on 2.15 beautifully landscaped, park-like acres just minutes from town, this exceptional six-bedroom residence offers a rare blend of timeless elegance, everyday comfort, and complete privacy. Thoughtfully designed for the way people truly live, the home is filled with light, gracious proportions, and inviting spaces that welcome both intimate gatherings and memorable celebrations. The heart of the home is a beautifully appointed chef's kitchen with a sunlit breakfast area that opens seamlessly to the spacious family room, where French doors invite you outdoors to expansive lawns and peaceful sunsets. Formal living and dining rooms provide the perfect backdrop for entertaining, while a butler's pantry and generous mudroom bring effortless function to everyday life. The tranquil primary suite is a retreat of its own, featuring a cozy fireplace, a private balcony overlooking the grounds, and a luxurious spa-inspired bath. Five additional en suite bedrooms offer exceptional comfort and privacy for family and guests. A finished third level provides a flexible bedroom and bonus space ideal for a home office, playroom, or creative studio, while the expansive lower level offers endless possibilities for recreation, fitness, media, or entertaining. Outside, sweeping lawns, mature landscaping, and exceptional privacy create a setting that feels worlds away, yet is only moments from town, schools, and everything Darien has to offer.

67 Peach Hill Rd, Darien

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