Refine Search
Sort by
24 Arrowhead Way, Darien
$6,250,000
5 Beds ⋅ 9 Baths ⋅ 24214699 MLS
In the prestigious Tokeneke Association, this elegant 8,300sf Colonial on 1.78 acres sits above lawns and beautiful gardens. Almost a 40% new addition and extensive renovations in 2006, the owners respected the architectural heritage while introducing the ease and refinement of contemporary living. The pool and spa sit within the back wraparound terrace, now an exceptional outdoor living sanctuary. A living room, sunroom, formal dining room, the connecting kitchen and family room with fireplace and the spectacular first floor primary wing all open through French doors onto the sunlit terrace and sweeping lawns. The vaulted primary suite with fireplace, his/her baths and dressing rooms leads to your own patio. Steps from the entry foyer is an elegant living and dining room, and a beautiful kitchen with an impressive nine-foot marble island opens onto the family room with fireplace and breakfast room all opening to the gardens, creating a natural flow from formal living to relaxed everyday life. Upstairs is a second primary suite with fireplace and sitting room and three additional en suite bedrooms. A cathedral ceiling great room with exposed beams and attached bath creates the ultimate in an entertaining space. A playroom is on the third floor. The walk-out lower level features a stone and wood office with bar and wine cellar and exercise room. A two car garage cottage has heated upstairs office/sleeping room. Serene and private. 47 miles NYC. The best of Darien

24 Arrowhead Way, Darien

6 Berry Ln, Darien
$5,025,000
6 Beds ⋅ 3 Baths ⋅ 24213301 MLS
There is a rare kind of magic when classic architecture meets a modern, artistic eye. Privately tucked at the end of a quiet cul-de-sac in Tokeneke School District. This stunning six-bedroom center-hall Colonial is surrounded by extraordinary grounds reminiscent of a private botanical garden. Mature specimen trees, sculpted greenery, flowering perennials and winding bluestone pathways create a breathtaking landscape in every season. Inside, sophisticated interiors blend timeless elegance with modern style. Sun-filled rooms, oversized windows, bespoke finishes and designer outdoor lighting frame spectacular garden views throughout. A beautifully remodeled eat-in kitchen serves as the heart of the home, flowing effortlessly into gracious living and entertaining spaces. Outdoors, an infinity-edge gunite pool and spa take center stage, surrounded by expansive bluestone terraces for dining, lounging and entertaining. A dedicated fire pit gathering area adds another enchanting dimension to this remarkable setting. Lush, mature landscaping provides exceptional privacy, creating a true resort-like retreat. Steps from Five Mile River, Rowayton and coastal Darien, this extraordinary property offers the perfect marriage of classic architecture, sophisticated design and unforgettable indoor-outdoor living. An exceptional property with the added luxury of flexibility, offering generous possibilities for future expansion.

6 Berry Ln, Darien

20 Lighthouse Way, 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

25 Pt O Woods Rd, Darien
$3,895,000
5 Beds ⋅ 6 Baths ⋅ 24214570 MLS
Classic character, exceptional space, and a setting you'll want to experience firsthand. Designed by architect Ed Wallace and built in 1933, 25 Point O Woods Road is a beautiful example of classic Center Hall Colonial craftsmanship, thoughtfully updated for today's lifestyle. Set on 1.15 beautifully landscaped acres, this inviting home blends timeless architecture with generous spaces and modern comfort. A gracious center hall leads to well-proportioned rooms and an impressive family room with a dramatic two-tier coffered ceiling. The recently renovated all-season sun porch, transformed from the original screened porch, offers a bright and comfortable space to enjoy the beauty of the grounds year-round. The flexible floor plan features five bedrooms, five full baths, and one half bath, with exceptional room for family and guests. Two additional rooms above the garage offer endless possibilities as home offices, a gym, guest spaces, or additional bedrooms. An expansive lower level includes a full bath, exercise room, and abundant storage. Outside, professionally landscaped grounds create a private setting for entertaining and everyday enjoyment. The level backyard is ideally sited for a pool, offering the opportunity to create a spectacular private retreat. With its architectural character, thoughtful updates, generous spaces, and exceptional setting, 25 Point O Woods Road is a home that feels special from the moment you arrive and one you won't want to leave!

25 Pt O Woods Rd, Darien

5 Cross Rd, 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

31 Hancock Ln, Darien
$3,595,000
3 Beds ⋅ 5 Baths ⋅ 24203056 MLS
Completely reimagined and renovated inside and out in 2023, 31 Hancock Lane is a remarkable English stone country residence where timeless architecture meets sophisticated modern living. Privately positioned on 1.5 beautifully landscaped acres, the property captures the romance and enduring character of a classic country estate while offering the refinement, comfort, and craftsmanship of a thoroughly renewed home. From the moment of arrival, the distinctive stone facade, cedar shingle roof, and mature, meticulously designed landscape establish an unmistakable sense of place. Inside, graciously scaled rooms unfold with a natural elegance, highlighted by handsome beamed ceilings, rich architectural detailing, and an inviting warmth throughout. The living room, centered around an impressive walk-in fireplace, flows effortlessly into the formal dining room, creating an ideal setting for both intimate occasions and grand entertaining. At the heart of the home, the beautifully appointed gourmet eat-in kitchen opens directly to a spectacular family room with vaulted ceilings and sweeping views of the park-like grounds. The main-level primary suite offers a private retreat, complete with his-and-her bathrooms and generous walk-in closets. Upstairs, two beautifully appointed en-suite bedrooms provide privacy and comfort for family and guests, while a versatile office or bonus room offers additional flexibility. A walk-up attic provides abundant storage and further potential.

31 Hancock Ln, Darien

72 Old Kings Hwy S, Darien
$3,499,000
5 Beds ⋅ 6 Baths ⋅ 24144031 MLS
Exceptional NEW CONSTRUCTION - Walk to Town - Experience a thoughtfully designed home by V&A Construction, a highly regarded local builder known for exceptional craftsmanship. Just a short walk to town, shops, restaurants and the train, the location is as convenient as it is desirable. The home features handcrafted cabinetry and millwork, wide-plank white oak floors and high ceilings throughout. Imported European windows and doors not only add a beautiful architectural element, but make the home feel exceptionally quiet and comfortable. A welcoming foyer opens to living and dining rooms, a private home office and a designer kitchen with breakfast nook, premium appliances and a fully equipped butler's pantry. The kitchen flows directly into a spacious family room with a wood-burning fireplace, creating an easy, open layout for everyday living and entertaining. The expansive mudroom offers generous storage, connects to a back staircase and leads to a spacious lower level that can accommodate a gym, media room and game room. The second floor includes five generously sized bedrooms, highlighted by a primary suite with dual walk-in closets and a spa-like bath with premium fixtures. A large third-floor loft provides flexible space for a playroom, additional office or a relaxed retreat. This award-winning builder is dedicated to creating homes of the highest quality. Rarely offered and not to be missed.

72 Old Kings Hwy S, Darien

30 Birch Rd, Darien
$2,895,000
4 Beds ⋅ 3 Baths ⋅ 24207661 MLS
Classic charm, updated for today. This distinctive English cottage offers over 4,000 square feet of gracious living space, set on over one acre of expansive, level grounds on one of the largest lots on the street-in one of Darien's most sought-after locations. Inside, generously proportioned, light-filled rooms blend timeless architectural character with an easy, comfortable flow. Rich hardwood floors, arched doorways, custom millwork and two beautiful stone fireplaces add warmth and distinction throughout. The heart of the home is the bright, spacious kitchen with a large center island, opening to a charming breakfast room wrapped in windows. The sun-filled family room features a handsome coffered ceiling and walls of windows overlooking the property, while gracious living and dining rooms provide wonderful spaces for everyday living and entertaining. Flexible first-floor space is ideal for a home office, den or playroom. This 4 bedroom and 2.5 bath home is complemented by approximately 1,100 square feet in the finished lower level, ideal for a playroom, media room, gym or recreation area. Outside, expansive level grounds surrounded by mature trees create a picturesque setting with plenty of space for outdoor entertaining, recreation and play. Thoughtfully maintained and improved over the years, this special home combines classic character and craftsmanship with the comfort of today's lifestyle. Located in the Ox Ridge School District, close to train, town and shops.

30 Birch Rd, Darien

53 Country Club Rd, Darien
$2,425,000
5 Beds ⋅ 5 Baths ⋅ 24210093 MLS
Rarely does a Darien Colonial of this caliber offer such an exceptional combination of space, quality, location and value. Nestled on a quiet cul-de-sac in the coveted Ox Ridge School District, this beautifully updated 5-bedroom, 4.5-bath home offers over 4,000 sq. ft. of gracious, move-in-ready living on the two main floors. Sunlight streams through soaring ceilings, illuminating a stunning two-story family room with fireplace and built-ins, opening to a remodeled eat-in kitchen and sunny breakfast area. Formal living and dining rooms, a private office and a bonus/playroom with fireplace complete the main level. Upstairs are five spacious bedrooms, three full baths and an oversized laundry room. The finished lower level features 1,000+ sq. ft., a full bath, mudroom, storage and flexible space for a sixth bedroom, gym or recreation room. Enjoy a welcoming neighborhood where neighbors gather and children play, just minutes from the Talmadge Hill train station, the Merritt Parkway and the shopping and dining in Darien, New Canaan, Stamford, and surrounding towns. At $2,425,000, appreciate the space, comfort and lifestyle of a substantial Darien home at a truly compelling price. An amazing opportunity seldom found in today's Darien real estate market. *Agents please see confidential remarks*

53 Country Club Rd, Darien

11 Highland Ave, Darien
$2,395,000
4 Beds ⋅ 4 Baths ⋅ 24208647 MLS
Ideally positioned just moments from downtown Darien and the train station, 11 Highland Avenue offers an exceptional blend of timeless New England architecture, classic sophistication, and effortless everyday comfort. Set on a tranquil street in a coveted neighborhood, this immaculate, light-filled residence presents a rare turn-key opportunity in one of Fairfield County's most desirable coastal enclaves. Thoughtfully reimagined for modern living, the main level unfolds with intuitive flow. Beautiful new hardwood floors sweep throughout, leading from the warm formal living room centered around a classic wood-burning fireplace to the heart of the home: a magnificent open-concept gourmet kitchen. Complete with quartz countertops and sleek stainless steel appliances, the kitchen seamlessly integrates with the dining and family rooms-creating the ultimate layout for both casual family gatherings and large-scale entertaining. The upper levels host four sun-drenched bedrooms, including a private primary retreat with an updated spa-inspired bath. A versatile finished lower level offers valuable additional living space, perfectly suited for a home gym and recreation area. Outdoors, the landscaped grounds serve as a private sanctuary. A spacious stone terrace provides an inviting backdrop for summer al fresco dining and relaxed outdoor enjoyment. A seamless combination of elevated style and prime proximity, this quintessential property captures the very best of Darien living.

11 Highland Ave, Darien

1644 Boston Post Rd, Darien
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 24201958 MLS
Rebuilt in 2007 by an award-winning builder and thoughtfully updated and maintained ever since, this exceptional home offers timeless design, quality craftsmanship, and a highly desirable location close to town, shopping, and everyday conveniences. A welcoming open floor plan features elegant living and dining spaces, a private home office, and a gourmet kitchen that seamlessly flows into the sun-filled family room with custom millwork and views of the professionally landscaped yard. The updated kitchen showcases new countertops, backsplash, refinished cabinetry, and updated appliances, creating a stylish and functional heart of the home. Upstairs, the renovated primary suite offers a luxurious retreat with a beautifully updated bath and generous walk-in closets, while three additional bedrooms and two full baths complete the second level. The finished lower level provides versatile space ideal for a playroom, media room, gym, or study area. Outside, a spacious terrace, outdoor grilling area, and newly fenced backyard create the perfect setting for entertaining and everyday enjoyment. Move-in ready and designed for today's lifestyle, this home offers the perfect blend of comfort, style, and convenience.

1644 Boston Post Rd, Darien

103 West Ave, Darien
$2,095,000
5 Beds ⋅ 4 Baths ⋅ 24201880 MLS
Turnkey living in the heart of Darien. Offering over 3,500 square feet of beautifully refreshed living space, this 5-bedroom Colonial combines generous proportions, exceptional outdoor space and one of Darien's most convenient locations, just steps from downtown's newest development and the train. Originally renovated and expanded in 2009 and thoughtfully improved ever since, the home underwent an extensive refresh in 2026 designed for effortless, move-in ready living. The expansive, open floor plan is anchored by an impressive great room and offers wonderful flexibility across four finished levels. Five bedrooms and 3.5 baths are complemented by finished third-floor bonus space and a versatile lower level currently configured as a mudroom, gym, and wine room. Outside is the home's unexpected showstopper. Set on a beautifully landscaped 0.40-acre property, the remarkably spacious and private backyard feels like its own retreat, complete with a stone patio, pool, and six-foot privacy fencing. An incredible amount of outdoor space for a home so close to the center of town. This is a rare opportunity to have it all: space, privacy, convenience, and truly turnkey living just a few minutes walk from all that downtown Darien has to offer.

103 West Ave, Darien

2 Stony Brook Rd S, Darien
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 24201408 MLS
Welcome home to effortless one-level living on a premier, lush one-acre lot in Darien. Available for the first time in 56 years, this beautifully maintained 4-bedroom, 2.5-bath ranch features a newer roof, windows, and driveway. The large classic footprint spans over 3000sf and allows for easy customization and personal upgrades to make this house your own. This sweet home is nestled in a neighborhood with homes valued up to $6M, which offers endless possibilities for improvements. The seamless layout flows across classic hardwood floors, anchored by two cozy fireplaces and massive picture windows in the formal living room, dining room, and den. Enjoy a casual eat-in kitchen, formal dining space for holiday gatherings, a large functional laundry room, and an attached 2-car garage with stepless entry directly into the home. Outside, your expansive private yard offers endless possibilities for entertaining or gardening. Centrally located just minutes from downtown shops, dining, the Darien and Noroton Heights train stations, and top-rated schools. Schedule your private showing today!

2 Stony Brook Rd S, Darien

9 Wilson Ridge Rd E, Darien
$1,895,000
4 Beds ⋅ 3 Baths ⋅ 24210698 MLS
Nestled at the end of a cul-de-sac in one of Darien's most desirable neighborhoods, 9 Wilson Ridge Road East offers a wonderful opportunity to create a home that's distinctly your own. This four bedroom two and a half bath home has a welcoming floor plan for today's lifestyle. The main level has a living room with a fireplace, a formal dining room and a spacious eat in kitchen with a generous family room. A separate Den offers a private space for work or relaxation while the Sunroom provides an inviting spot to relax and enjoy the outdoors. Upstairs the primary suite is joined by 3 additional bedrooms, hardwood floors throughout the home. A large unfinished basement offers exciting potential for additional living space. A two car attached garage adds everyday convenience. Set on a beautiful half acre lot, this home is just minutes from the Noroton Heights train station, Darien Commons, and Heights Crossing, with restaurants, cafes, shops and daily essentials close by. With its inviting setting and exceptional location, this is a rare opportunity!

9 Wilson Ridge Rd E, Darien

13 Chestnut St, 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

60 Middlesex Rd, Darien
$1,749,000
4 Beds ⋅ 3 Baths ⋅ 24197232 MLS
Experience the timeless allure of 60 Middlesex Road, a quintessential New England Colonial that perfectly captures the spirit of Darien living. This warm residence offers a serene escape while keeping the town center, top-rated schools, and commuter links just moments away. From the moment you step inside, the home feels both sophisticated and deeply welcoming. The expansive living room, anchored by a cozy fireplace, invites you to linger, while the formal dining room is bathed in natural light, setting the stage for memorable dinner parties. At the heart of the home, the kitchen is a true showpiece, outfitted with stainless steel appliances that will delight any chef. This space flows effortlessly into a butler's pantry and sun-drenched family room, complete with a convenient half-bath. Indoor-outdoor living is perfected here. Slide open the doors to discover a large deck overlooking a gracious sized fenced-in backyard-an ideal backdrop for alfresco dining or quiet afternoons surrounded by greenery. Retreat to the second floor, where the luxurious primary suite serves as a private haven with its own ensuite bath and a spacious walk-in closet. Three additional bright bedrooms and a well-appointed full bathroom provide plenty of space for everyone. For even more flexibility, the lower level offers a versatile area ready to adapt to your specific lifestyle needs, whether it's for a home gym or a quiet office. This is more than just a house; it's a place to truly feel at home.

60 Middlesex Rd, Darien

2435 Boston Post Rd, Darien
$1,699,900
5 Beds ⋅ 4 Baths ⋅ 24184615 MLS
Spacious Colonial in the sought-after Hindley Elementary School district! Offering over 2500sf on the main and upper levels, this 5-bedroom, 3 full and 1 half bath home is designed for comfortable everyday living and entertaining. The oversized primary suite is complemented by generous living spaces, while 500sf finished lower level with wet bar provides an ideal recreation room, media room, home gym, or entertaining space. The eat-in kitchen opens to a large deck overlooking a private, fully fenced backyard-perfect for outdoor dining, children, pets, and summer gatherings. Enjoy the convenience of sidewalks leading to Darien's train station, downtown shops, restaurants, parks, beaches, and the Darien YMCA with beach view just across the street, offering competitive swimming and outstanding gymnastic programs, nursery school and activities for all ages. Public transportation is nearby, and quick access to I-95 makes commuting a breeze. Move right in and experience the exceptional convenience and lifestyle that Darien has to offer.

2435 Boston Post Rd, Darien

27 Lakeside Ave, Darien
$1,649,000
3 Beds ⋅ 3 Baths ⋅ 24211645 MLS
A rare opportunity to live on Tilley Pond Park - with stunning park and water views, on a coveted street that offers a lifestyle like no other. This storybook blend of scenic beauty and coastal charm offers an idyllic walk to all, with newly expanded shopping and restaurants of downtown Darien and the train just steps away. Have it all with beautiful nearby beaches and award-winning schools. Take in one of Darien's most picturesque locations every day, from the ultimate place to curl up with a book or a morning coffee - your enchanting, heated front porch with wrap-around windows. Or choose a cozy spot in front of your beautiful living room fireplace. Everyday living and entertaining are a breeze with a bright and spacious open first floor that also includes a family room with built-ins and dining room with bay window. The newer kitchen with vaulted ceiling, Wolf range and breakfast bar has Carrera marble counters, heated floors and sliders to a generous bluestone patio, perfect for outdoor dining. The level fenced-in yard offers privacy, professionally maintained mature plantings and handy garden shed. A convenient first floor bedroom and full bath complete the first level. Find two more bedrooms on the second floor of this romantic cottage-style home, including a large sunny primary bedroom with skylight, walk-in closet and full bath. The finished lower level provides even more living space with another full bath, a recreation room with built-ins, laundry & generous storage

27 Lakeside Ave, Darien

29 Lynn Ct, Darien
$1,050,000
4 Beds ⋅ 2 Baths ⋅ 24202576 MLS
***HIGHEST AND BEST DUE 9/1 AT 10:00AM TO LISTING AGENT EMAIL*** Welcome to 29 Lynn Court, a charming four-bedroom home tucked away on a quiet cul-de-sac in the heart of Darien. Offering a wonderful combination of comfortable living spaces, a private setting and an exceptional neighborhood feel, this is a home designed for easy everyday living. Inside, a welcoming layout offers plenty of space to gather, relax and make your own. The kitchen features appliances that are less than a year old, while four bedrooms provide flexibility for family, guests or a home office. Outside, enjoy a lovely back deck, patio and yard and one of the best parts of Lynn Court, its true sense of community. Neighbors gather for an annual block party each September and welcome a special holiday visitor every December, beloved traditions that make this street feel especially warm and connected. Located in the highly desirable Holmes Elementary School district, 29 Lynn Court puts you close to everything that makes Darien such an incredible place to live. Enjoy award-winning schools, beautiful parks and beaches, a vibrant downtown, great restaurants and shopping, and an easy commute with Metro-North and I-95 just minutes away. With its cul-de-sac setting, welcoming neighborhood and unbeatable Darien location, 29 Lynn Court offers an opportunity to put down roots and enjoy all that this special community has to offer.

29 Lynn Ct, 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.

How much is your home worth?

Get instant property value now!