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(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

$8,500,000

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

$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

$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

$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