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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

6 Beds ⋅ 8 Baths ⋅ 24078034 MLS

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

Hay Island, Darien

$13,000,000

Set on 9.4 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, a two-bedroom guest cottage, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house delivers a one-of-a-kind recreational and entertaining experience, featuring an indoor batting cage, two-lane bowling alley, resistance pool, and stylish lounge spaces. This offering is for all three parcels, each with its own address and private entrance, offering rare flexibility, exclusivity, and privacy.

5 Beds ⋅ 10 Baths ⋅ 24148914 MLS

Set on 9.4 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, a two-bedroom guest cottage, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house delivers a one-of-a-kind recreational and entertaining experience, featuring an indoor batting cage, two-lane bowling alley, resistance pool, and stylish lounge spaces. This offering is for all three parcels, each with its own address and private entrance, offering rare flexibility, exclusivity, and privacy.

865 Hollow Tree Ridge Rd, Darien

$9,420,000

Introducing one of Tokeneke's most iconic waterfront estates-available for the first time in 50 years. This rare and storied compound is set on 2.4 acres of exquisitely landscaped grounds with 180 feet of private shoreline along Long Island Sound. It offers an unrivaled blend of historic charm, timeless elegance, and breathtaking coastal beauty. A sweeping two-story paneled foyer leads to a gracious formal living and dining rooms with soaring ceilings, fireplaces, and uninterrupted views of the water. Sunlight pours into the sophisticated sunroom-an ideal setting for quiet mornings or refined entertaining. The expansive kitchen and breakfast area open seamlessly to a family room with a granite fireplace, while a discreet back stairway leads to a stunning double-height billiards room with vaulted, beamed ceilings. The second floor is anchored by a grand primary suite with an oversized waterfront balcony, offering a private vantage point for sunsets over the Sound. Two additional bedrooms complete this level, with three more on the top floor to accommodate family or guests in style. A separate three-car garage includes a fully finished upper level with a full bath-ideal for a guest suite, gym, or private office. This exceptional estate embodies the quiet prestige of a bygone era, offering privacy, beauty, and unparalleled access to the water-all in the heart of Darien's most coveted private enclave. A once-in-a-generation opportunity to own a true coastal masterpiece.

6 Beds ⋅ 5 Baths ⋅ 24115997 MLS

Introducing one of Tokeneke's most iconic waterfront estates-available for the first time in 50 years. This rare and storied compound is set on 2.4 acres of exquisitely landscaped grounds with 180 feet of private shoreline along Long Island Sound. It offers an unrivaled blend of historic charm, timeless elegance, and breathtaking coastal beauty. A sweeping two-story paneled foyer leads to a gracious formal living and dining rooms with soaring ceilings, fireplaces, and uninterrupted views of the water. Sunlight pours into the sophisticated sunroom-an ideal setting for quiet mornings or refined entertaining. The expansive kitchen and breakfast area open seamlessly to a family room with a granite fireplace, while a discreet back stairway leads to a stunning double-height billiards room with vaulted, beamed ceilings. The second floor is anchored by a grand primary suite with an oversized waterfront balcony, offering a private vantage point for sunsets over the Sound. Two additional bedrooms complete this level, with three more on the top floor to accommodate family or guests in style. A separate three-car garage includes a fully finished upper level with a full bath-ideal for a guest suite, gym, or private office. This exceptional estate embodies the quiet prestige of a bygone era, offering privacy, beauty, and unparalleled access to the water-all in the heart of Darien's most coveted private enclave. A once-in-a-generation opportunity to own a true coastal masterpiece.

17 Contentment Island Rd, Darien

$8,850,000

(Don't miss the spectacular waterfront video). On the water in the Tokeneke Association, Short Rocks Manor is poised at the very tip of Arrowhead Way, high above Scotts Cove and Long Island Sound. This breathtaking, updated 1925 English-style stone manor sits on 2.11 acres which includes .362 acres of designated OPEN SPACE. The 5,823 square feet of exquisite craftmanship houses five bedrooms - including a private-entrance apartment perfect for guests or family. Up the circular drive, you enter through a private stone rose-filled courtyard into the fabulous foyer with fireplace and step in the soaring two-story great room with floor to ceiling windows of glass that open directly onto your waterfront terrace, with the cove and Sound shimmering beyond. Every principal room has been oriented to capture the water. The primary bedroom suite window wall overlooks the ever-changing beauty of the sea. The kitchen leads to a private patio. Acres of landscaped gardens unfold across multiple levels, a private swimming pool is nestled within its own secluded garden sanctuary, and a whimsical Fairy Path winds upward to a hidden garden perched high above the cove creating a bird and wildlife sanctuary. The separate viewing terrace overlooks the water and your own private dock and is perfect for evening cocktails or simply watching the sun set over Long Island Sound. This home and property are rare. Make it your own.

5 Beds ⋅ 6 Baths ⋅ 24180009 MLS

(Don't miss the spectacular waterfront video). On the water in the Tokeneke Association, Short Rocks Manor is poised at the very tip of Arrowhead Way, high above Scotts Cove and Long Island Sound. This breathtaking, updated 1925 English-style stone manor sits on 2.11 acres which includes .362 acres of designated OPEN SPACE. The 5,823 square feet of exquisite craftmanship houses five bedrooms - including a private-entrance apartment perfect for guests or family. Up the circular drive, you enter through a private stone rose-filled courtyard into the fabulous foyer with fireplace and step in the soaring two-story great room with floor to ceiling windows of glass that open directly onto your waterfront terrace, with the cove and Sound shimmering beyond. Every principal room has been oriented to capture the water. The primary bedroom suite window wall overlooks the ever-changing beauty of the sea. The kitchen leads to a private patio. Acres of landscaped gardens unfold across multiple levels, a private swimming pool is nestled within its own secluded garden sanctuary, and a whimsical Fairy Path winds upward to a hidden garden perched high above the cove creating a bird and wildlife sanctuary. The separate viewing terrace overlooks the water and your own private dock and is perfect for evening cocktails or simply watching the sun set over Long Island Sound. This home and property are rare. Make it your own.

82 Arrowhead Way, Darien

$8,775,000

Perched high on the bluff of Long Neck Point, this 6680sf custom-built brick estate offers you unmatched privacy and panoramic water views, all in this captivating natural environment where land and sea converge in harmony. Set on 1.38 acres with 175 feet of shoreline, the home enjoys 180-degree views over Long Island Sound, with main floor rooms capturing the stunning scenery and the ever-changing water. The home opens with a dramatic marble foyer and circular staircase. Graciously scaled rooms feature 9-foot ceilings, an oversized arched window and sliding glass door walls that flood the interiors with light. A long flat backyard, with a 20 X 40 ft concrete pool, slopes gently toward the water, leading to a private dock. The home offers five bedrooms, a luxurious primary suite with its own wing, dual bathrooms and two large walk-in closets. Indoor 38x6 ft lap pool in a separate glass room with sliders to the garden and sea. Separate in-law apartment has a private entrance, kitchen, and sitting room. The lower level has a great room with fireplace, home office with built ins, gym, and a newly renovated pool bathroom and dressing room. Three-car garage, a new slate-style DaVinci roof, new furnace, new A/C units, 45 " Viking cooktop, new oil tanks, full property landscaping and a partially finished attic with cedar closet. This is a rare opportunity to own a truly special waterfront home where every detail was thoughtfully designed to elevate daily living.

5 Beds ⋅ 7 Baths ⋅ 24112893 MLS

Perched high on the bluff of Long Neck Point, this 6680sf custom-built brick estate offers you unmatched privacy and panoramic water views, all in this captivating natural environment where land and sea converge in harmony. Set on 1.38 acres with 175 feet of shoreline, the home enjoys 180-degree views over Long Island Sound, with main floor rooms capturing the stunning scenery and the ever-changing water. The home opens with a dramatic marble foyer and circular staircase. Graciously scaled rooms feature 9-foot ceilings, an oversized arched window and sliding glass door walls that flood the interiors with light. A long flat backyard, with a 20 X 40 ft concrete pool, slopes gently toward the water, leading to a private dock. The home offers five bedrooms, a luxurious primary suite with its own wing, dual bathrooms and two large walk-in closets. Indoor 38x6 ft lap pool in a separate glass room with sliders to the garden and sea. Separate in-law apartment has a private entrance, kitchen, and sitting room. The lower level has a great room with fireplace, home office with built ins, gym, and a newly renovated pool bathroom and dressing room. Three-car garage, a new slate-style DaVinci roof, new furnace, new A/C units, 45 " Viking cooktop, new oil tanks, full property landscaping and a partially finished attic with cedar closet. This is a rare opportunity to own a truly special waterfront home where every detail was thoughtfully designed to elevate daily living.

101 Long Neck Point Rd, Darien

$8,745,000

Privately set within Darien's Tokeneke School District , 45 Old Farm is a remarkable custom estate by award-winning builder Oliver Wilson. A tree-lined drive framed by natural stone pillars sets the tone for this exceptional property. Inside, every room is thoughtfully composed with striking sight lines and abundant natural light. The chef's kitchen is a true centerpiece, anchored by a dramatic 17-foot honed Calacatta Picasso marble waterfall island, and flows seamlessly into the family room with floor-to-ceiling custom windows and a striking travertine fireplace. The resort-style exterior features a custom 45-foot pool and spa, outdoor kitchen, and fireplace designed for effortless indoor-outdoor living. The upper levels offer five spacious bedrooms, including a serene primary suite with a bespoke dressing room and spa-like bath. A separate private wing offers ideal flexibility as an office or sixth bedroom, complete with a wet bar, full bath, and private terrace. The lower level impresses with soaring 11-foot ceilings, expansive recreation space, wine room, private gym, sauna, full bath, and space for a golf simulator. Defined by timeless design, impeccable craftsmanship, and extraordinary attention to detail, 45 Old Farm Road is THE listing of 2026.

5 Beds ⋅ 8 Baths ⋅ 24175610 MLS

Privately set within Darien's Tokeneke School District , 45 Old Farm is a remarkable custom estate by award-winning builder Oliver Wilson. A tree-lined drive framed by natural stone pillars sets the tone for this exceptional property. Inside, every room is thoughtfully composed with striking sight lines and abundant natural light. The chef's kitchen is a true centerpiece, anchored by a dramatic 17-foot honed Calacatta Picasso marble waterfall island, and flows seamlessly into the family room with floor-to-ceiling custom windows and a striking travertine fireplace. The resort-style exterior features a custom 45-foot pool and spa, outdoor kitchen, and fireplace designed for effortless indoor-outdoor living. The upper levels offer five spacious bedrooms, including a serene primary suite with a bespoke dressing room and spa-like bath. A separate private wing offers ideal flexibility as an office or sixth bedroom, complete with a wet bar, full bath, and private terrace. The lower level impresses with soaring 11-foot ceilings, expansive recreation space, wine room, private gym, sauna, full bath, and space for a golf simulator. Defined by timeless design, impeccable craftsmanship, and extraordinary attention to detail, 45 Old Farm Road is THE listing of 2026.

45 Old Farm Rd, Darien

$8,695,000

25 Tokeneke Trail - Where the Sky meets the Sea. Wake up to breathtaking sunrises, spend afternoons on the water, and end each day with sunset views from your private terrace. 25 Tokeneke Trail isn't just a home-it's a lifestyle. Perfectly perched above the shoreline and not in a flood zone, this stunning waterfront retreat offers direct access to the water with its own private beach and dock. Designed for seamless indoor-outdoor living, nearly every room frames panoramic water views. Multiple stone terraces, a firepit, and lush landscaping create the perfect setting for entertaining or quiet relaxation. Inside, over 6,000 sq. ft. of refined living space includes five bedrooms, seven baths, and a private studio suite over the detached garage ideal for a guest house or private retreat. Minutes from downtown Darien and the train to NYC, this rare property blends the serenity of coastal living with the best of modern luxury.

5 Beds ⋅ 8 Baths ⋅ 24126696 MLS

25 Tokeneke Trail - Where the Sky meets the Sea. Wake up to breathtaking sunrises, spend afternoons on the water, and end each day with sunset views from your private terrace. 25 Tokeneke Trail isn't just a home-it's a lifestyle. Perfectly perched above the shoreline and not in a flood zone, this stunning waterfront retreat offers direct access to the water with its own private beach and dock. Designed for seamless indoor-outdoor living, nearly every room frames panoramic water views. Multiple stone terraces, a firepit, and lush landscaping create the perfect setting for entertaining or quiet relaxation. Inside, over 6,000 sq. ft. of refined living space includes five bedrooms, seven baths, and a private studio suite over the detached garage ideal for a guest house or private retreat. Minutes from downtown Darien and the train to NYC, this rare property blends the serenity of coastal living with the best of modern luxury.

25 Tokeneke Trl, Darien

$8,500,000

This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately combine the best of an elegant and storied past of the original grandeur of its early twentieth century origins with new and soaring modern spaces. They meticulously recreated the splendor of the arches, moldings, windows, light fixtures and even the original sweeping driveway while updating it for the state-of-the-art fine living of today. Round Meadows' totally renovated 19 room home has 7 bedrooms, 7 full baths, including a spectacular primary suite with spa, 3 half baths, library, office and guest suite. Enter through the 2 story foyer with soaring ceilings to the 3 large entertaining rooms, comprised of the living room, sunroom with bar, and an elegant formal dining room with fireplace. The inviting gourmet kitchen is seamlessly connected to a cozy family room with a fireplace which opens onto extensive terraces that overlook acres of manicured lawns and gardens. Add the 3 car garage off a grand mud hall with bath and laundry. Round Meadows honors the past as it pays forward an aspirational essence in the new construction feel, anchored by old world sophistication.

7 Beds ⋅ 10 Baths ⋅ 24122386 MLS

This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately combine the best of an elegant and storied past of the original grandeur of its early twentieth century origins with new and soaring modern spaces. They meticulously recreated the splendor of the arches, moldings, windows, light fixtures and even the original sweeping driveway while updating it for the state-of-the-art fine living of today. Round Meadows' totally renovated 19 room home has 7 bedrooms, 7 full baths, including a spectacular primary suite with spa, 3 half baths, library, office and guest suite. Enter through the 2 story foyer with soaring ceilings to the 3 large entertaining rooms, comprised of the living room, sunroom with bar, and an elegant formal dining room with fireplace. The inviting gourmet kitchen is seamlessly connected to a cozy family room with a fireplace which opens onto extensive terraces that overlook acres of manicured lawns and gardens. Add the 3 car garage off a grand mud hall with bath and laundry. Round Meadows honors the past as it pays forward an aspirational essence in the new construction feel, anchored by old world sophistication.

18 Tokeneke Trl, Darien

$8,195,000

Your homestead starts here-welcome to 30 Shipway Road, a private waterfront retreat set on 1.49 incredible acres in sought-after Noroton Bay. Designed by renowned architect Chad Nehring, with coastal interiors by Pear Tree Point Design, this 5 bedroom home blends timeless style with modern comfort. Nearly every room takes in sweeping, unobstructed views of the harbor and Long Island Sound, creating a peaceful, picture-perfect setting all year long. The main living spaces flow easily outdoors to a deep water dock, beautiful pool and spa, lush grounds, and gas fire pit - perfect for relaxing or entertaining by the water. The primary suite is a true escape, with vaulted ceilings and its own private balcony overlooking the water-ideal for morning coffee. There's also a two-car attached garage, plus a detached three-car garage with a well-appointed apartment above, great for guests or extended family. A rare opportunity in one of Darien's most desirable waterfront neighborhoods, this home truly captures the best of coastal living.

5 Beds ⋅ 8 Baths ⋅ 24167751 MLS

Your homestead starts here-welcome to 30 Shipway Road, a private waterfront retreat set on 1.49 incredible acres in sought-after Noroton Bay. Designed by renowned architect Chad Nehring, with coastal interiors by Pear Tree Point Design, this 5 bedroom home blends timeless style with modern comfort. Nearly every room takes in sweeping, unobstructed views of the harbor and Long Island Sound, creating a peaceful, picture-perfect setting all year long. The main living spaces flow easily outdoors to a deep water dock, beautiful pool and spa, lush grounds, and gas fire pit - perfect for relaxing or entertaining by the water. The primary suite is a true escape, with vaulted ceilings and its own private balcony overlooking the water-ideal for morning coffee. There's also a two-car attached garage, plus a detached three-car garage with a well-appointed apartment above, great for guests or extended family. A rare opportunity in one of Darien's most desirable waterfront neighborhoods, this home truly captures the best of coastal living.

30 Shipway Rd, Darien

$7,200,000

Nestled within the highly coveted Tokeneke Association, this custom-designed English country manor embodies understated elegance and timeless craftsmanship. Ideally located near Scott's Cove and featuring a private dock, the five-bedroom residence was created with meticulous attention to detail throughout. An impressive foyer sets the tone, revealing the dining room's classic period charm and a richly paneled hallway that leads to an exquisite private office. The expansive family room, highlighted by soaring ceilings, flows seamlessly into a finely crafted gourmet kitchen, a newly designed mudroom, and a well-appointed guest suite. The second floor is anchored by an oversized primary suite with a custom walk-in closet and spa like bath, complemented by three additional on suite bedrooms and an oversized great room. Impeccably appointed throughout, this exceptional home offers a refined balance of sophistication and comfort, perfectly suited for both elegant entertaining and everyday living.

5 Beds ⋅ 8 Baths ⋅ 24081666 MLS

Nestled within the highly coveted Tokeneke Association, this custom-designed English country manor embodies understated elegance and timeless craftsmanship. Ideally located near Scott's Cove and featuring a private dock, the five-bedroom residence was created with meticulous attention to detail throughout. An impressive foyer sets the tone, revealing the dining room's classic period charm and a richly paneled hallway that leads to an exquisite private office. The expansive family room, highlighted by soaring ceilings, flows seamlessly into a finely crafted gourmet kitchen, a newly designed mudroom, and a well-appointed guest suite. The second floor is anchored by an oversized primary suite with a custom walk-in closet and spa like bath, complemented by three additional on suite bedrooms and an oversized great room. Impeccably appointed throughout, this exceptional home offers a refined balance of sophistication and comfort, perfectly suited for both elegant entertaining and everyday living.

76 Arrowhead Way, Darien

$6,510,000

Set on a beautifully landscaped and expansive property, 28 Old Farm Road offers a rare blend of refined elegance and modern comfort. Thoughtfully designed with impeccable attention to detail, the residence features five spacious bedrooms, each with its own en suite bathroom. An exceptional primary suite was designed as a private retreat. This serene space includes a separate lounge area, an oversized walk-in closet, and a spa-inspired bathroom with views of a manicured, sprawling lawn and a beautifully designed pool complete with a safety cover, ideal for both relaxation and entertaining. Every outdoor element has been carefully curated to enhance the sense of luxury and privacy. Inside, the home has been recently reimagined by renowned designer Naomi Stroh, whose sophisticated vision brings a fresh, elevated aesthetic to every room. The finished lower level offers versatile space perfect for recreation, a home gym, or additional living, all complemented by ample storage. The interiors seamlessly blend timeless style with contemporary finishes, resulting in a warm yet striking living environment. This is a rare opportunity to own a move-in-ready, design-forward home in one of Darien's most desirable locations in the private Tokeneke Association.

5 Beds ⋅ 8 Baths ⋅ 24162725 MLS

Set on a beautifully landscaped and expansive property, 28 Old Farm Road offers a rare blend of refined elegance and modern comfort. Thoughtfully designed with impeccable attention to detail, the residence features five spacious bedrooms, each with its own en suite bathroom. An exceptional primary suite was designed as a private retreat. This serene space includes a separate lounge area, an oversized walk-in closet, and a spa-inspired bathroom with views of a manicured, sprawling lawn and a beautifully designed pool complete with a safety cover, ideal for both relaxation and entertaining. Every outdoor element has been carefully curated to enhance the sense of luxury and privacy. Inside, the home has been recently reimagined by renowned designer Naomi Stroh, whose sophisticated vision brings a fresh, elevated aesthetic to every room. The finished lower level offers versatile space perfect for recreation, a home gym, or additional living, all complemented by ample storage. The interiors seamlessly blend timeless style with contemporary finishes, resulting in a warm yet striking living environment. This is a rare opportunity to own a move-in-ready, design-forward home in one of Darien's most desirable locations in the private Tokeneke Association.

28 Old Farm Rd, Darien

$6,500,000

10 Cross Road is custom built and thoughtfully designed by Louise Brooks & Artisan Builders. No expense has been spared...extensive millwork and moldings, soaring 10-foot and cathedral ceilings! In the heart of the private Tokeneke Assoc. on a hilltop with southern exposure, multiple French doors create a seamless indoor-outdoor lifestyle. Enjoy a custom pool, spa, & waterfall beautifully integrated into lush gardens and refined hardscaping. Meticulously maintained, this private backyard offers a true oasis - you won't want to leave! A chef's kitchen appointed with Wolf and Sub-Zero appliances, a dble. island and a cozy dining area with expansive windows and fireplace is open to a grand family room. Formal living and dining room with entertaining butlers parlor and mature office complete the main floor. Upstairs, the spacious primary suite offers a sitting area, walk-in closets and serene bathroom. 3 ensuite bedrooms provide luxurious accommodations. The 3rd floor offers a large playroom space with 2 adjacent bedrooms sharing a jack-and-jill bathroom. Additional amenities include a 3-car heated garage, theater, gym, sauna and partial heated driveway. Many recent improvements - including a new cedar roof, newly paved driveway, full exterior painting, new front stone wall, and pool enhancements - further elevate the home's turnkey appeal. Come experience the beauty, history, and prestige of Tokeneke at its finest, a private coastal community just a short distance from town.

6 Beds ⋅ 8 Baths ⋅ 24153454 MLS

10 Cross Road is custom built and thoughtfully designed by Louise Brooks & Artisan Builders. No expense has been spared...extensive millwork and moldings, soaring 10-foot and cathedral ceilings! In the heart of the private Tokeneke Assoc. on a hilltop with southern exposure, multiple French doors create a seamless indoor-outdoor lifestyle. Enjoy a custom pool, spa, & waterfall beautifully integrated into lush gardens and refined hardscaping. Meticulously maintained, this private backyard offers a true oasis - you won't want to leave! A chef's kitchen appointed with Wolf and Sub-Zero appliances, a dble. island and a cozy dining area with expansive windows and fireplace is open to a grand family room. Formal living and dining room with entertaining butlers parlor and mature office complete the main floor. Upstairs, the spacious primary suite offers a sitting area, walk-in closets and serene bathroom. 3 ensuite bedrooms provide luxurious accommodations. The 3rd floor offers a large playroom space with 2 adjacent bedrooms sharing a jack-and-jill bathroom. Additional amenities include a 3-car heated garage, theater, gym, sauna and partial heated driveway. Many recent improvements - including a new cedar roof, newly paved driveway, full exterior painting, new front stone wall, and pool enhancements - further elevate the home's turnkey appeal. Come experience the beauty, history, and prestige of Tokeneke at its finest, a private coastal community just a short distance from town.

10 Cross Rd, Darien

$6,100,000

Set on two private acres in coveted northern Darien, this exceptional Colonial offers refined living, timeless design, and superior craftsmanship throughout. A gracious living room with fireplace provides a warm and sophisticated gathering space, while the formal dining room is perfectly complemented by an adjacent butler's pantry, ideal for seamless entertaining. A richly appointed study/library with its own fireplace offers a quiet and distinguished retreat.At the heart of the home, the expansive kitchen and family room open effortlessly to the spectacular outdoor living areas, creating the perfect setting for both everyday living and large-scale entertaining. Outside, the grounds have been transformed into a true private retreat featuring a pool, renovated pool house, outdoor kitchen, BBQ pit, pergola and fire pit - offering an exceptional backdrop for entertaining and year-round enjoyment. The fully remodeled lower level is thoughtfully designed for recreation and relaxation, featuring a custom theater room, walk-in wine cellar, and luxurious sauna. This remarkable property seamlessly combines luxury, comfort, and modern functionality in one of Darien's most desirable locations.

5 Beds ⋅ 7 Baths ⋅ 24173379 MLS

Set on two private acres in coveted northern Darien, this exceptional Colonial offers refined living, timeless design, and superior craftsmanship throughout. A gracious living room with fireplace provides a warm and sophisticated gathering space, while the formal dining room is perfectly complemented by an adjacent butler's pantry, ideal for seamless entertaining. A richly appointed study/library with its own fireplace offers a quiet and distinguished retreat.At the heart of the home, the expansive kitchen and family room open effortlessly to the spectacular outdoor living areas, creating the perfect setting for both everyday living and large-scale entertaining. Outside, the grounds have been transformed into a true private retreat featuring a pool, renovated pool house, outdoor kitchen, BBQ pit, pergola and fire pit - offering an exceptional backdrop for entertaining and year-round enjoyment. The fully remodeled lower level is thoughtfully designed for recreation and relaxation, featuring a custom theater room, walk-in wine cellar, and luxurious sauna. This remarkable property seamlessly combines luxury, comfort, and modern functionality in one of Darien's most desirable locations.

38 Three Wells Ln, Darien

$6,095,000

Architecturally stunning six-bedroom Colonial graces 2.29 level acres designed for resort-style living with pool, pool house, outdoor shower, stone terrace with kitchen & garden masterfully built in 2014. Beautifully appointed 6,117 sq ft interior brimming with exquisite details including high coffered ceilings, transom topped doorways & box molding. Striking double height foyer introduces ideal floor plan, perfect for everyday living & entertaining, anchored by chef's marble-clad kitchen which opens to large family room with fireplace flanked by doors to magnificent screened porch with industrial grade heaters & fireplace. Elegant dining room with fully equipped butler's pantry, stylish living room & office both with fireplaces, mudroom & two powder rooms round out this level. Sumptuous primary suite with fireplace, his/her walk-in closets, deluxe bath with radiant heated floors; two en-suite bedrooms, two bedrooms with Jack/Jill bath, homework area, laundry room comprise 2nd floor. Generous lower-level boasts media room with projector, game room, wine room with wine refrigerator, bedroom, full bath & generator. Unfinished top floor features ample storage & unlimited potential. Outdoor Kalamazoo gourmet kitchen is fitted with grill, pizza oven, smoker & kegerators. Incredible pool house (add'l 860 sq ft) includes custom kitchenette, half bath with outdoor shower & loft. Ideally located on professionally landscaped, private lot with fenced-in yard near all Darien offers.

6 Beds ⋅ 8 Baths ⋅ 24158797 MLS

Architecturally stunning six-bedroom Colonial graces 2.29 level acres designed for resort-style living with pool, pool house, outdoor shower, stone terrace with kitchen & garden masterfully built in 2014. Beautifully appointed 6,117 sq ft interior brimming with exquisite details including high coffered ceilings, transom topped doorways & box molding. Striking double height foyer introduces ideal floor plan, perfect for everyday living & entertaining, anchored by chef's marble-clad kitchen which opens to large family room with fireplace flanked by doors to magnificent screened porch with industrial grade heaters & fireplace. Elegant dining room with fully equipped butler's pantry, stylish living room & office both with fireplaces, mudroom & two powder rooms round out this level. Sumptuous primary suite with fireplace, his/her walk-in closets, deluxe bath with radiant heated floors; two en-suite bedrooms, two bedrooms with Jack/Jill bath, homework area, laundry room comprise 2nd floor. Generous lower-level boasts media room with projector, game room, wine room with wine refrigerator, bedroom, full bath & generator. Unfinished top floor features ample storage & unlimited potential. Outdoor Kalamazoo gourmet kitchen is fitted with grill, pizza oven, smoker & kegerators. Incredible pool house (add'l 860 sq ft) includes custom kitchenette, half bath with outdoor shower & loft. Ideally located on professionally landscaped, private lot with fenced-in yard near all Darien offers.

304 Brookside Rd, Darien

$5,660,000

This exceptional Shingle Style Colonial blends form and function to inspire elegant everyday living. Set on a private 1.4-acre lot, it offers four levels of thoughtfully designed space by Daniel Conlon Architects with refined millwork details & finishes throughout. The main level features a two-story foyer, formal living and dining rooms, a chef's kitchen with walk-in pantry, and a great room opening to an expansive terrace overlooking the heated pool and spa. Highlights include a library, home office, 1st floor guest suite, and elevator. The primary suite offers a fireplace, spa-like bath, dressing room, and two walk-in closets. Three additional ensuite bedrooms and laundry complete the second floor. A flexible upper level includes a fifth bedroom/Flex room and large walk-in storage. The full walkout lower level offers a playroom, gym, full bath, wet bar, mudroom with direct access to the three-car garage, pool & terrace. All just minutes to downtown, train station, beaches and the many amenities Darien has to offer that make this gold coast community so desirable.

6 Beds ⋅ 8 Baths ⋅ 24125071 MLS

This exceptional Shingle Style Colonial blends form and function to inspire elegant everyday living. Set on a private 1.4-acre lot, it offers four levels of thoughtfully designed space by Daniel Conlon Architects with refined millwork details & finishes throughout. The main level features a two-story foyer, formal living and dining rooms, a chef's kitchen with walk-in pantry, and a great room opening to an expansive terrace overlooking the heated pool and spa. Highlights include a library, home office, 1st floor guest suite, and elevator. The primary suite offers a fireplace, spa-like bath, dressing room, and two walk-in closets. Three additional ensuite bedrooms and laundry complete the second floor. A flexible upper level includes a fifth bedroom/Flex room and large walk-in storage. The full walkout lower level offers a playroom, gym, full bath, wet bar, mudroom with direct access to the three-car garage, pool & terrace. All just minutes to downtown, train station, beaches and the many amenities Darien has to offer that make this gold coast community so desirable.

10 Stony Brook Rd, Darien

$5,625,000

Just in time for summer-this exceptional property offers the ultimate in luxury living and outdoor enjoyment. Imagine relaxing poolside by your new heated pool and spa, surrounded by beautifully landscaped grounds and sweeping views of the golf course. Inside, the home is equally impressive. The expansive primary suite is a true retreat, featuring a private sitting room that opens onto a deck overlooking the pool-perfect for morning coffee or evening unwinding. The suite also boasts a beautifully updated bath and two spacious walk-in closets. The second level is thoughtfully designed with four additional en-suite bedrooms and a versatile playroom, offering comfort and privacy for family and guests alike. At the heart of the home is a stunning new gourmet kitchen, outfitted with top-of-the-line appliances including a Wolf range, two Sub-Zero refrigerators, a separate freezer, and three dishwashers-an entertainer's dream. The lower level is equally striking, featuring an elite gym, a playroom, and abundant open space for recreation and play-perfect for entertaining, relaxing, or staying active without ever leaving home. This remarkable colonial seamlessly blends elegance, comfort, and modern convenience-perfect for making unforgettable summer memories and beyond.

5 Beds ⋅ 7 Baths ⋅ 24167771 MLS

Just in time for summer-this exceptional property offers the ultimate in luxury living and outdoor enjoyment. Imagine relaxing poolside by your new heated pool and spa, surrounded by beautifully landscaped grounds and sweeping views of the golf course. Inside, the home is equally impressive. The expansive primary suite is a true retreat, featuring a private sitting room that opens onto a deck overlooking the pool-perfect for morning coffee or evening unwinding. The suite also boasts a beautifully updated bath and two spacious walk-in closets. The second level is thoughtfully designed with four additional en-suite bedrooms and a versatile playroom, offering comfort and privacy for family and guests alike. At the heart of the home is a stunning new gourmet kitchen, outfitted with top-of-the-line appliances including a Wolf range, two Sub-Zero refrigerators, a separate freezer, and three dishwashers-an entertainer's dream. The lower level is equally striking, featuring an elite gym, a playroom, and abundant open space for recreation and play-perfect for entertaining, relaxing, or staying active without ever leaving home. This remarkable colonial seamlessly blends elegance, comfort, and modern convenience-perfect for making unforgettable summer memories and beyond.

316 Mansfield Ave, Darien

$5,500,000

This Dockside home is a short paddle away from Five Mile River. Quietly iconic. Effortlessly cool. Live large without living complicated. This is the rare waterfront home that offers the lifestyle of a grand estate with the ease of a true lock-and-leave retreat. Set on just over an acre in the private Tokeneke Association it's designed for living well not maintaining endlessly. There are four private bedrooms in the main house and several places to kick back. Escape whenever you choose a weekend, a week, or all the days in between. Paddle over to Rowayton for lunch, entertain under the stars by the fire, or spend an afternoon with a great book by the pool. A private guest cottage with multiple sleep configurations offers family and friends their own retreat while preserving yours. Waterfront homes that live this effortlessly are incredibly rare. A manageable home, beautiful grounds, a dock, freeform pool, an abundant vegetable garden and even a chicken coop, all within the security of Tokeneke including optional home check-ins while you're away. Make coming and going completely carefree, an easy house, an extraordinary life.

5 Beds ⋅ 5 Baths ⋅ 24171365 MLS

This Dockside home is a short paddle away from Five Mile River. Quietly iconic. Effortlessly cool. Live large without living complicated. This is the rare waterfront home that offers the lifestyle of a grand estate with the ease of a true lock-and-leave retreat. Set on just over an acre in the private Tokeneke Association it's designed for living well not maintaining endlessly. There are four private bedrooms in the main house and several places to kick back. Escape whenever you choose a weekend, a week, or all the days in between. Paddle over to Rowayton for lunch, entertain under the stars by the fire, or spend an afternoon with a great book by the pool. A private guest cottage with multiple sleep configurations offers family and friends their own retreat while preserving yours. Waterfront homes that live this effortlessly are incredibly rare. A manageable home, beautiful grounds, a dock, freeform pool, an abundant vegetable garden and even a chicken coop, all within the security of Tokeneke including optional home check-ins while you're away. Make coming and going completely carefree, an easy house, an extraordinary life.

13 Edgehill Dr, Darien

$5,200,000

Exquisitely renovated center hall colonial set on two perfectly manicured acres at end of quiet, private cul-de-sac, offering exceptional space & timeless appeal for both everyday living & entertaining. Renovated in 2023 by ERI Building & Design, this stunning six-bedroom home with private office, four full & two half baths showcases impeccable craftsmanship & sophisticated design throughout. Dramatic open-concept kitchen features two oversized islands, walk-in pantry, Sub-Zero refrigerator & freezer, & an inviting breakfast area flowing seamlessly into soaring great room overlooking expansive rear lawn & tennis court with room for pool - perfect setting for gathering with family & friends. Light-filled sunroom provides ideal spot for relaxing with morning coffee while enjoying peaceful views of property. Designed for elegant entertaining, the home features gracious formal living room with fireplace, stunning bar & lounge area, wine pantry, & formal dining room with butler's pantry. Luxurious first-floor suite provides exceptional comfort & privacy for visitors. Upstairs luxurious primary suite with fireplace & spa-like ambiance, creates peaceful retreat. Four additional generously sized bedrooms feature beautifully appointed jack-jill baths. Private office just across hall creates ultimate work-from-home setting. Thoughtfully designed lower level provides flexible, ample space for gym or playroom. This truly exceptional home offering elegance & an unparalleled lifestyle.

6 Beds ⋅ 6 Baths ⋅ 24175837 MLS

Exquisitely renovated center hall colonial set on two perfectly manicured acres at end of quiet, private cul-de-sac, offering exceptional space & timeless appeal for both everyday living & entertaining. Renovated in 2023 by ERI Building & Design, this stunning six-bedroom home with private office, four full & two half baths showcases impeccable craftsmanship & sophisticated design throughout. Dramatic open-concept kitchen features two oversized islands, walk-in pantry, Sub-Zero refrigerator & freezer, & an inviting breakfast area flowing seamlessly into soaring great room overlooking expansive rear lawn & tennis court with room for pool - perfect setting for gathering with family & friends. Light-filled sunroom provides ideal spot for relaxing with morning coffee while enjoying peaceful views of property. Designed for elegant entertaining, the home features gracious formal living room with fireplace, stunning bar & lounge area, wine pantry, & formal dining room with butler's pantry. Luxurious first-floor suite provides exceptional comfort & privacy for visitors. Upstairs luxurious primary suite with fireplace & spa-like ambiance, creates peaceful retreat. Four additional generously sized bedrooms feature beautifully appointed jack-jill baths. Private office just across hall creates ultimate work-from-home setting. Thoughtfully designed lower level provides flexible, ample space for gym or playroom. This truly exceptional home offering elegance & an unparalleled lifestyle.

27 Hillsley Rd, Darien

$5,200,000

Spectacular quintessential New England home in Darien has it all! Step into a world of refined elegance with this stately 8,000+SF Colonial masterpiece. Set back on nearly two acres of manicured grounds, boasting a custom 2021 Gunite pool, outdoor kitchen, new patio, huge backyard and firepit, this treasured residence is the ultimate venue for indoor & outdoor living and entertaining. The main level features a soaring 2-story foyer that transitions into a formal living room w/fireplace & stunning formal dining room w/ butlers pantry, wet bar, wine fridge & food pantry. Step into the chef's kitchen w/ 16ft marble island, Miele range, dual Sub-zeros & sun-drenched breakfast area. The kitchen flows into a massive family room w/ stone fireplace & adjoining sunroom w/ 25ft stone fireplace w/French doors to backyard & pool. There's a large, office w/ custom paneling & coffered ceiling, a mudroom w/built-ins, plus a full bath, a powder room and back staircase to upper level rooms. The 2nd floor primary suite is a private sanctuary, defined by 11-foot barrel vaulted ceilings, a fireplace, 2 walk-in closets and a spa-inspired marble bath w/double sink, soaking tub & steam shower. There are 4 additional en-suite bedrooms, a laundry room & open space for study/gaming. The 3rd floor has over 2,400sqft of storage/ potential living space!

5 Beds ⋅ 8 Baths ⋅ 24156548 MLS

Spectacular quintessential New England home in Darien has it all! Step into a world of refined elegance with this stately 8,000+SF Colonial masterpiece. Set back on nearly two acres of manicured grounds, boasting a custom 2021 Gunite pool, outdoor kitchen, new patio, huge backyard and firepit, this treasured residence is the ultimate venue for indoor & outdoor living and entertaining. The main level features a soaring 2-story foyer that transitions into a formal living room w/fireplace & stunning formal dining room w/ butlers pantry, wet bar, wine fridge & food pantry. Step into the chef's kitchen w/ 16ft marble island, Miele range, dual Sub-zeros & sun-drenched breakfast area. The kitchen flows into a massive family room w/ stone fireplace & adjoining sunroom w/ 25ft stone fireplace w/French doors to backyard & pool. There's a large, office w/ custom paneling & coffered ceiling, a mudroom w/built-ins, plus a full bath, a powder room and back staircase to upper level rooms. The 2nd floor primary suite is a private sanctuary, defined by 11-foot barrel vaulted ceilings, a fireplace, 2 walk-in closets and a spa-inspired marble bath w/double sink, soaking tub & steam shower. There are 4 additional en-suite bedrooms, a laundry room & open space for study/gaming. The 3rd floor has over 2,400sqft of storage/ potential living space!

7 Buttonwood Ln, Darien

$5,000,000

Welcome to 473 Hollow Tree Ridge Road in Darien - a custom built, stone and shingle Colonial set on 1.3 professionally landscaped acres offering exceptional indoor and outdoor living. This 5-bedroom smart home blends timeless architecture with extensive upgrades and modern technology throughout. The resort-style backyard features a pool with spa, pool house with nano doors, outdoor shower, custom outdoor bar, Lynx grill, fireplace, and covered patio. A slate roof, horseshoe driveway, whole-house 25kW Generac generator, and oversized 3-car garage with heated epoxy floors, built-ins, and wainscoting provide both convenience and peace of mind. The fully remodeled kitchen includes a Wolf range, additional wall oven, Sub-Zero double refrigerator/freezer, double islands with prep sink and second dishwasher, Negresco granite and quartz countertops, island seating, and a wet bar with glass dishwasher and ice maker. A paneled office, homework stations, guest/au pair suite with private access, oversized mudroom, laundry, and two powder rooms complete the main level. Upstairs, the primary suite features a renovated spa bath with heated floors, freestanding tub, oversized shower with rain head, and custom walk-in closets. Two additional ensuite bedrooms, a fourth bedroom with hall bath, game room with full wet bar, media room, and office/workstations provide flexible living.

5 Beds ⋅ 8 Baths ⋅ 24157029 MLS

Welcome to 473 Hollow Tree Ridge Road in Darien - a custom built, stone and shingle Colonial set on 1.3 professionally landscaped acres offering exceptional indoor and outdoor living. This 5-bedroom smart home blends timeless architecture with extensive upgrades and modern technology throughout. The resort-style backyard features a pool with spa, pool house with nano doors, outdoor shower, custom outdoor bar, Lynx grill, fireplace, and covered patio. A slate roof, horseshoe driveway, whole-house 25kW Generac generator, and oversized 3-car garage with heated epoxy floors, built-ins, and wainscoting provide both convenience and peace of mind. The fully remodeled kitchen includes a Wolf range, additional wall oven, Sub-Zero double refrigerator/freezer, double islands with prep sink and second dishwasher, Negresco granite and quartz countertops, island seating, and a wet bar with glass dishwasher and ice maker. A paneled office, homework stations, guest/au pair suite with private access, oversized mudroom, laundry, and two powder rooms complete the main level. Upstairs, the primary suite features a renovated spa bath with heated floors, freestanding tub, oversized shower with rain head, and custom walk-in closets. Two additional ensuite bedrooms, a fourth bedroom with hall bath, game room with full wet bar, media room, and office/workstations provide flexible living.

473 Hollow Tree Ridge Rd, Darien

$4,800,000

Located on a peaceful cul-de-sac yet just minutes from town, the train, and top-rated schools, this stunning home offers the perfect balance of tranquility and convenience. Inside, you'll find high ceilings, beautiful moldings, custom built-ins, and an open floor plan designed for modern living. The large, renovated kitchen is a true centerpiece, featuring high-end finishes and generous space for cooking, dining, and gathering. The first floor also includes a beautifully updated living room, dining room, private office and a comfortable guest room, ideal for visitors or extended family. Upstairs, you'll find four spacious bedrooms, including a luxurious primary suite, plus a versatile great room perfect for a playroom, gym, or additional lounge space. Set on a full acre of landscaped, fenced-in property, the outdoor area is ideal for both relaxation and entertaining. Enjoy the heated pool, unwind by the outdoor fireplace, or host memorable gatherings in your private backyard retreat. This home combines elegance, comfort, and an unbeatable location.

5 Beds ⋅ 5 Baths ⋅ 24131779 MLS

Located on a peaceful cul-de-sac yet just minutes from town, the train, and top-rated schools, this stunning home offers the perfect balance of tranquility and convenience. Inside, you'll find high ceilings, beautiful moldings, custom built-ins, and an open floor plan designed for modern living. The large, renovated kitchen is a true centerpiece, featuring high-end finishes and generous space for cooking, dining, and gathering. The first floor also includes a beautifully updated living room, dining room, private office and a comfortable guest room, ideal for visitors or extended family. Upstairs, you'll find four spacious bedrooms, including a luxurious primary suite, plus a versatile great room perfect for a playroom, gym, or additional lounge space. Set on a full acre of landscaped, fenced-in property, the outdoor area is ideal for both relaxation and entertaining. Enjoy the heated pool, unwind by the outdoor fireplace, or host memorable gatherings in your private backyard retreat. This home combines elegance, comfort, and an unbeatable location.

6 Priscilla Ln, Darien

$4,795,000

Set on nearly 2 private acres in coveted northern Darien, this exceptional custom Colonial offers refined living with timeless design and superior craftsmanship throughout. Detailed with exquisite custom moldings, the home exudes elegance in every space. A dramatic step-down living room with fireplace creates a warm and inviting atmosphere, while the spacious formal dining room is perfectly complemented by an adjacent butler's pantry-ideal for effortless entertaining. A richly appointed library with its own fireplace provides a quiet retreat. The gourmet kitchen opens seamlessly to a generous family room with fireplace, forming the heart of the home, and is supported by two conveniently located powder rooms. Upstairs, a second family room offers additional flexible living space, an office and five well-proportioned bedrooms and four full baths, including a luxurious primary suite. The lower level is designed for both recreation and lifestyle, featuring a walk-in wine cellar, a large level playroom/craft room with double sinks, and a dedicated workout room. Outdoors, the professionally landscaped grounds provide a private oasis with a beautiful pool and an outdoor fireplace-perfect for relaxing and entertaining year-round. Complete with a three-car garage, this remarkable property combines elegance, comfort and functionality in one of Darien's most desirable settings.

5 Beds ⋅ 6 Baths ⋅ 24164236 MLS

Set on nearly 2 private acres in coveted northern Darien, this exceptional custom Colonial offers refined living with timeless design and superior craftsmanship throughout. Detailed with exquisite custom moldings, the home exudes elegance in every space. A dramatic step-down living room with fireplace creates a warm and inviting atmosphere, while the spacious formal dining room is perfectly complemented by an adjacent butler's pantry-ideal for effortless entertaining. A richly appointed library with its own fireplace provides a quiet retreat. The gourmet kitchen opens seamlessly to a generous family room with fireplace, forming the heart of the home, and is supported by two conveniently located powder rooms. Upstairs, a second family room offers additional flexible living space, an office and five well-proportioned bedrooms and four full baths, including a luxurious primary suite. The lower level is designed for both recreation and lifestyle, featuring a walk-in wine cellar, a large level playroom/craft room with double sinks, and a dedicated workout room. Outdoors, the professionally landscaped grounds provide a private oasis with a beautiful pool and an outdoor fireplace-perfect for relaxing and entertaining year-round. Complete with a three-car garage, this remarkable property combines elegance, comfort and functionality in one of Darien's most desirable settings.

74 Salisbury Rd, Darien

$4,750,000

This quintessential colonial sits on a quiet cul-de-sac only minutes from town. The main level consists of an updated kitchen, multiple family/living rooms that serve as functional gathering spaces with three wood burning fireplaces, a dining room, two powder rooms and a large three car garage. Front and back staircases lead you up to six bedrooms which includes a primary bedroom with gas fireplace and four full bathrooms. Finished lower level is perfect for a playroom/theater room with a gym and workshop. French doors lead you out back where you will find a large saltwater pool with a beautifully landscaped lawn, a new fence and an outdoor firepit - the perfect space to entertain. New roof in 2025. Don't miss this meticulously maintained home!

6 Beds ⋅ 6 Baths ⋅ 24167376 MLS

This quintessential colonial sits on a quiet cul-de-sac only minutes from town. The main level consists of an updated kitchen, multiple family/living rooms that serve as functional gathering spaces with three wood burning fireplaces, a dining room, two powder rooms and a large three car garage. Front and back staircases lead you up to six bedrooms which includes a primary bedroom with gas fireplace and four full bathrooms. Finished lower level is perfect for a playroom/theater room with a gym and workshop. French doors lead you out back where you will find a large saltwater pool with a beautifully landscaped lawn, a new fence and an outdoor firepit - the perfect space to entertain. New roof in 2025. Don't miss this meticulously maintained home!

8 Haskell Ln, Darien

$4,750,000

Set along a picturesque stretch in one of Darien's most sought-after neighborhoods, 234 Brookside Road offers a rare blend of timeless architecture, privacy, and modern comfort. Surrounded by mature trees and beautifully landscaped grounds, this exceptional property provides a serene, retreat-like setting just minutes from town, top-rated schools, and the coastline. This HOBI award-winning residence welcomes you with a gracious entry that opens into expansive, light-filled interiors designed for both elegance and ease. A thoughtfully planned, free-flowing layout connects formal living and dining rooms-ideal for entertaining-with inviting casual spaces suited to everyday living. The well-appointed kitchen serves as the heart of the home, featuring high-end appliances and seamless flow to family gathering areas and outdoor living spaces. Upstairs, the tranquil primary suite features a vaulted ceiling, dual walk-in closets, and a spacious spa-inspired bath. Each of the four additional bedrooms offers an en suite bath, ensuring comfort and privacy for family and guests. Complementing the approximately 5,700-square-foot main house is a fully equipped 1,100-square-foot guest house with living and dining areas, a full kitchen, a wood-burning fireplace, and a private suite with a full bathroom. Set on 1.4 level acres, the outdoor spaces include a gunite pool and spa, outdoor kitchen, and fireplace-perfect for entertaining or relaxing in complete privacy year-round.

6 Beds ⋅ 7 Baths ⋅ 24164395 MLS

Set along a picturesque stretch in one of Darien's most sought-after neighborhoods, 234 Brookside Road offers a rare blend of timeless architecture, privacy, and modern comfort. Surrounded by mature trees and beautifully landscaped grounds, this exceptional property provides a serene, retreat-like setting just minutes from town, top-rated schools, and the coastline. This HOBI award-winning residence welcomes you with a gracious entry that opens into expansive, light-filled interiors designed for both elegance and ease. A thoughtfully planned, free-flowing layout connects formal living and dining rooms-ideal for entertaining-with inviting casual spaces suited to everyday living. The well-appointed kitchen serves as the heart of the home, featuring high-end appliances and seamless flow to family gathering areas and outdoor living spaces. Upstairs, the tranquil primary suite features a vaulted ceiling, dual walk-in closets, and a spacious spa-inspired bath. Each of the four additional bedrooms offers an en suite bath, ensuring comfort and privacy for family and guests. Complementing the approximately 5,700-square-foot main house is a fully equipped 1,100-square-foot guest house with living and dining areas, a full kitchen, a wood-burning fireplace, and a private suite with a full bathroom. Set on 1.4 level acres, the outdoor spaces include a gunite pool and spa, outdoor kitchen, and fireplace-perfect for entertaining or relaxing in complete privacy year-round.

234 Brookside Rd, Darien

$4,725,000

Tucked in the Delafield Island Association and moments from the beach, town, train, & schools, this custom built 5-bedroom residence offers an ideal blend of timeless elegance & modern comfort. Thoughtfully designed with soaring ceilings, an open floor plan & sun-filled interiors, nearly every main living space enjoys beautiful views of the pool & private backyard. A dramatic two-story foyer welcomes you into gracious dining room and parlor, creating a dramatic first impression. At the heart of the home is a spectacular eat in chef's kitchen featuring two expansive islands, abundant custom cabinetry, & seamless flow into the spacious family room & opens to a covered terrace with built-in heaters, creating the perfect setting for year-round indoor/outdoor entertaining. 2 home offices, breakfast nook, 2 powder rooms, & a large mudroom, complete the 1st fl. The luxurious primary suite is a true retreat, highlighted by a vaulted ceiling, lg walk-in closet & spa-inspired bath w radiant heated floors, soaking tub, double vanity, & oversized shower. An adjoining sitting room offers the perfect space for a private lounge, gym or nursery. 4 addl generously sized BRs & 3 full baths provide room for all, while the spacious 2nd fl landing is an inviting area for reading/relaxing. Finished huge basement w high ceilings has versatile space to add a golf simulator. 3rd fl is framed & plumbed, offering an outstanding opportunity to create a bedroom suite w bath tailored to your needs

5 Beds ⋅ 6 Baths ⋅ 24194430 MLS

Tucked in the Delafield Island Association and moments from the beach, town, train, & schools, this custom built 5-bedroom residence offers an ideal blend of timeless elegance & modern comfort. Thoughtfully designed with soaring ceilings, an open floor plan & sun-filled interiors, nearly every main living space enjoys beautiful views of the pool & private backyard. A dramatic two-story foyer welcomes you into gracious dining room and parlor, creating a dramatic first impression. At the heart of the home is a spectacular eat in chef's kitchen featuring two expansive islands, abundant custom cabinetry, & seamless flow into the spacious family room & opens to a covered terrace with built-in heaters, creating the perfect setting for year-round indoor/outdoor entertaining. 2 home offices, breakfast nook, 2 powder rooms, & a large mudroom, complete the 1st fl. The luxurious primary suite is a true retreat, highlighted by a vaulted ceiling, lg walk-in closet & spa-inspired bath w radiant heated floors, soaking tub, double vanity, & oversized shower. An adjoining sitting room offers the perfect space for a private lounge, gym or nursery. 4 addl generously sized BRs & 3 full baths provide room for all, while the spacious 2nd fl landing is an inviting area for reading/relaxing. Finished huge basement w high ceilings has versatile space to add a golf simulator. 3rd fl is framed & plumbed, offering an outstanding opportunity to create a bedroom suite w bath tailored to your needs

13 Sunswyck Rd, Darien

$4,700,000

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.

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

$4,602,000

In-ground pool - Cul-de-Sac - Tennis courts - Wine cellar - Gym -Firepit - Finished attic and basement

4 Beds ⋅ 7 Baths ⋅ 24150779 MLS

In-ground pool - Cul-de-Sac - Tennis courts - Wine cellar - Gym -Firepit - Finished attic and basement

5 Shields Ln, Darien

$4,600,000

Welcome to this classic Coastal Connecticut colonial, ideally situated in the coveted Tokeneke Association - offering space, comfort, and versatility for every member of the family. With 5 bedrooms - including a convenient first-floor guest suite and four bedrooms on the second level - this home is designed for gracious everyday living. The main floor features a formal living room, elegant dining room, casual dining area, and a spacious office, all flowing effortlessly together. The chef's kitchen opens to both casual dining and a warm, fireplace-lit gathering room, the heart of the home. A large mudroom with garage and back-entrance access, plus a separate laundry room, adds everyday ease. Retreat to the private primary suite, complete with an en-suite bath and two walk-in closets. The second floor also offers a second en-suite bedroom, two additional bedrooms sharing a beautifully renovated hall bath, a versatile sitting/work area, and abundant storage throughout. The finished basement boasts a spectacular wine room, that holds 1600 bottles, and casual sitting area - perfect for relaxing or entertaining. The attached garage holds two-cars plus, and a third bay is in the "barn" - a blank canvas ready to become a guest quarters, entertaining space, second-floor hangout, studio, or whatever you can imagination. Outside, unwind on the beautiful stone patio, set against an expansive, green yard. A rare opportunity in one of the most sought-after associations.

5 Beds ⋅ 5 Baths ⋅ 24190513 MLS

Welcome to this classic Coastal Connecticut colonial, ideally situated in the coveted Tokeneke Association - offering space, comfort, and versatility for every member of the family. With 5 bedrooms - including a convenient first-floor guest suite and four bedrooms on the second level - this home is designed for gracious everyday living. The main floor features a formal living room, elegant dining room, casual dining area, and a spacious office, all flowing effortlessly together. The chef's kitchen opens to both casual dining and a warm, fireplace-lit gathering room, the heart of the home. A large mudroom with garage and back-entrance access, plus a separate laundry room, adds everyday ease. Retreat to the private primary suite, complete with an en-suite bath and two walk-in closets. The second floor also offers a second en-suite bedroom, two additional bedrooms sharing a beautifully renovated hall bath, a versatile sitting/work area, and abundant storage throughout. The finished basement boasts a spectacular wine room, that holds 1600 bottles, and casual sitting area - perfect for relaxing or entertaining. The attached garage holds two-cars plus, and a third bay is in the "barn" - a blank canvas ready to become a guest quarters, entertaining space, second-floor hangout, studio, or whatever you can imagination. Outside, unwind on the beautiful stone patio, set against an expansive, green yard. A rare opportunity in one of the most sought-after associations.

6 Searles Rd, Darien

$4,600,000

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.

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

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.

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