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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

$24,210,000

A GOLD COAST opportunity: 6.6 acres of pristine estate living culminating at 400 ft of direct Long Island Sound waterfront.A winding drive from the famed Beachside Ave enclave leads past the tennis pavilion, through the shaded trees and into a cobblestone courtyard with fountain and perfectly manicured garden entry.Stepping through the front door, the striking view of blue water tops the lush green lawns like a painting. The main fl of this Roger Ferris shingle style colonial was designed for luxury coastal living, the main living room, sun room, and kitchen all pour out onto the gorgeous south facing patio through endless walls of windows & French doors.Each space meticulously finished to be comfortable for everyday living while also ready for seamless indoor/outdoor entertaining at a moment's notice with smart & almost sneaky placement of pocket doors, cocktail room & butler's pantry. The main house boasts spacious 5 bdrms. The primary suite, consisting of a spectacular bedroom with rustic barn wood ceilings & water views in every direction is balanced by the clean lines of a recently redesigned sleek sitting room & the modern bath + dressing room done in crisp whites. There are 2 multi room bedroom suites finished in New England resort style & a guest wing w/ 2 additional bedrooms, bath & separate entrance hall. The home has 4 garages + a covered bay, a full basement w hotel level laundry room, storage, catering prep room & immaculate utility rooms geothermal home heating.

5 Beds ⋅ 6 Baths ⋅ 24066972 MLS

A GOLD COAST opportunity: 6.6 acres of pristine estate living culminating at 400 ft of direct Long Island Sound waterfront.A winding drive from the famed Beachside Ave enclave leads past the tennis pavilion, through the shaded trees and into a cobblestone courtyard with fountain and perfectly manicured garden entry.Stepping through the front door, the striking view of blue water tops the lush green lawns like a painting. The main fl of this Roger Ferris shingle style colonial was designed for luxury coastal living, the main living room, sun room, and kitchen all pour out onto the gorgeous south facing patio through endless walls of windows & French doors.Each space meticulously finished to be comfortable for everyday living while also ready for seamless indoor/outdoor entertaining at a moment's notice with smart & almost sneaky placement of pocket doors, cocktail room & butler's pantry. The main house boasts spacious 5 bdrms. The primary suite, consisting of a spectacular bedroom with rustic barn wood ceilings & water views in every direction is balanced by the clean lines of a recently redesigned sleek sitting room & the modern bath + dressing room done in crisp whites. There are 2 multi room bedroom suites finished in New England resort style & a guest wing w/ 2 additional bedrooms, bath & separate entrance hall. The home has 4 garages + a covered bay, a full basement w hotel level laundry room, storage, catering prep room & immaculate utility rooms geothermal home heating.

122 Beachside Ave, Westport

$20,790,000

6.62 acres of Long Island Sound waterfront property. A stunning modern architectural masterpiece. The structure is anchored by a 75 ft indoor pool and wall of seamless glass windows that feel connected to the water beyond , the single story structure also holds a kitchen, lounge and bath. The Red Barn is a secondary structure in the orchard section of the property - designed as an artist's studio on the main floor, there is also a bedroom, bathroom and living area on the second floor.

1 Beds ⋅ 1 Baths ⋅ 24129357 MLS

6.62 acres of Long Island Sound waterfront property. A stunning modern architectural masterpiece. The structure is anchored by a 75 ft indoor pool and wall of seamless glass windows that feel connected to the water beyond , the single story structure also holds a kitchen, lounge and bath. The Red Barn is a secondary structure in the orchard section of the property - designed as an artist's studio on the main floor, there is also a bedroom, bathroom and living area on the second floor.

128 Beachside Ave, Westport

$16,500,000

Exceptional commanding luxury estate under development in prime mid country location. The 2.39 acre gated & elevated site includes a 13,326 SF main house with 6 bedrooms / 8.3 bathrooms across 4 levels of custom crafted living space with indoor parking for 7 cars - plus an outfitted 800 SF luxury pool house with vaulted ceilings, heated floors, stone fireplace & full bathroom overlooking a large terrace, 50 ft. pool with integrated spa & sundeck plus a sprawling lawn area with sunken fire pit & Bocce court. Designed by the SOHO Group, this striking transitional home with soaring ceilings & tremendous light is perfectly layered in clapboard, hand chiseled fieldstone & oversize glass. A 3-stop elevator plus an amenity-filled lower level complete the offering. Est. completion date: Dec. 2025

6 Beds ⋅ 12 Baths ⋅ 24113844 MLS

Exceptional commanding luxury estate under development in prime mid country location. The 2.39 acre gated & elevated site includes a 13,326 SF main house with 6 bedrooms / 8.3 bathrooms across 4 levels of custom crafted living space with indoor parking for 7 cars - plus an outfitted 800 SF luxury pool house with vaulted ceilings, heated floors, stone fireplace & full bathroom overlooking a large terrace, 50 ft. pool with integrated spa & sundeck plus a sprawling lawn area with sunken fire pit & Bocce court. Designed by the SOHO Group, this striking transitional home with soaring ceilings & tremendous light is perfectly layered in clapboard, hand chiseled fieldstone & oversize glass. A 3-stop elevator plus an amenity-filled lower level complete the offering. Est. completion date: Dec. 2025

382 N St St, Greenwich

$15,500,000

Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of parklike grounds and over 200 feet of waterfront, including a waterfront pool, well-equipped pool house, and 3-bedroom guest cottage. Approach through the gated stone walls and travel the tree-lined drive, enjoying the unfolding Sound views. Rich with original character, the main residence evokes the grace of a bygone era with leaded glass windows, impressive millwork, and grand gathering spaces featuring soaring ceilings designed to showcase the breathtaking views. Included in the home's magic is this wonder: a sailing ship imported from England, reconstructed on site to create a one-of-a-kind study. Generations have hosted parties on these magnificent grounds, enjoyed quiet mornings by the seawall or spent a day boating from the mooring off its private beach. This former longtime home of Lucie Bedford and her husband, Briggs Cunningham - race car driver and America's Cup winner - is a landmark opportunity to own a storied piece of Westport's history along prestigious Beachside Avenue. A one-of-one opportunity to carry on this legacy of luxury and history at this iconic waterfront estate.

8 Beds ⋅ 9 Baths ⋅ 24130997 MLS

Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of parklike grounds and over 200 feet of waterfront, including a waterfront pool, well-equipped pool house, and 3-bedroom guest cottage. Approach through the gated stone walls and travel the tree-lined drive, enjoying the unfolding Sound views. Rich with original character, the main residence evokes the grace of a bygone era with leaded glass windows, impressive millwork, and grand gathering spaces featuring soaring ceilings designed to showcase the breathtaking views. Included in the home's magic is this wonder: a sailing ship imported from England, reconstructed on site to create a one-of-a-kind study. Generations have hosted parties on these magnificent grounds, enjoyed quiet mornings by the seawall or spent a day boating from the mooring off its private beach. This former longtime home of Lucie Bedford and her husband, Briggs Cunningham - race car driver and America's Cup winner - is a landmark opportunity to own a storied piece of Westport's history along prestigious Beachside Avenue. A one-of-one opportunity to carry on this legacy of luxury and history at this iconic waterfront estate.

92 Beachside Ave, Westport

$14,600,000

Sited on over two acres of private, west-facing land in the heart of Greenwich's coveted Golden Triangle, this architectural modern masterpiece commands attention. Designed in collaboration with renowned architect William D. Earls, this 11,000+ sq ft six-bedroom estate showcases timeless design, masterful craftsmanship, and refined sophistication. Completed in 2018, the residence blends bold contemporary lines with warm, livable elegance. Inside, soaring ceilings, dramatic steel-framed windows, and sunlit open spaces create an extraordinary sense of volume and light. The chef's kitchen is a showpiece, featuring Sub-Zero, Wolf, and Bosch appliances, HR Woodworking custom cabinetry, and bespoke finishes throughout. The luxurious primary suite serves as a serene retreat, featuring a spa-like bath, dual dressing rooms, fireplace, a private terrace, and sweeping sunset views. Expansive walls of glass open to a resort-style backyard with a Groppa saline pool and spa, sculpted gardens designed by Joseph Pajonas Studio and multiple terraces offering the ultimate in indoor-outdoor living and entertaining.

6 Beds ⋅ 10 Baths ⋅ 24156495 MLS

Sited on over two acres of private, west-facing land in the heart of Greenwich's coveted Golden Triangle, this architectural modern masterpiece commands attention. Designed in collaboration with renowned architect William D. Earls, this 11,000+ sq ft six-bedroom estate showcases timeless design, masterful craftsmanship, and refined sophistication. Completed in 2018, the residence blends bold contemporary lines with warm, livable elegance. Inside, soaring ceilings, dramatic steel-framed windows, and sunlit open spaces create an extraordinary sense of volume and light. The chef's kitchen is a showpiece, featuring Sub-Zero, Wolf, and Bosch appliances, HR Woodworking custom cabinetry, and bespoke finishes throughout. The luxurious primary suite serves as a serene retreat, featuring a spa-like bath, dual dressing rooms, fireplace, a private terrace, and sweeping sunset views. Expansive walls of glass open to a resort-style backyard with a Groppa saline pool and spa, sculpted gardens designed by Joseph Pajonas Studio and multiple terraces offering the ultimate in indoor-outdoor living and entertaining.

30 Meadowcroft Ln, Greenwich

$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

$12,900,000

Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.13 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light, highlighting the breathtaking water views that can be enjoyed from nearly every room. Outside, indulge in the serene beauty of a sparkling pool and a private dock, perfect for those who love the water, while westward-facing vistas offer stunning sunsets. A walk-out lower level elevates the home's functionality, making it a rare fine in Riverside!

6 Beds ⋅ 7 Baths ⋅ 24127692 MLS

Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.13 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light, highlighting the breathtaking water views that can be enjoyed from nearly every room. Outside, indulge in the serene beauty of a sparkling pool and a private dock, perfect for those who love the water, while westward-facing vistas offer stunning sunsets. A walk-out lower level elevates the home's functionality, making it a rare fine in Riverside!

52 Carriglea Dr, Greenwich

$12,000,000

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every space has been curated with an uncompromising attention to detail-from custom millwork to premium finishes-creating an environment that is as functional as it is beautiful. Set on one of the most coveted streets in Southport, this property offers the perfect balance of privacy and proximity. Just a short stroll to the harbor and Long Island Sound, the setting recalls the charm of Nantucket or the Hamptons while retaining the unmistakable character of Southport. The transformation of the entire estate-including the main house, guest house, pool, and pool house-is nothing short of remarkable. The extensive list of upgrades and enhancements is too comprehensive to list here; this is a home that must be seen to be fully appreciated. Experience 260 Willow Street-a residence that invites you to live beautifully, entertain effortlessly, and enjoy the best of coastal village life.

7 Beds ⋅ 7 Baths ⋅ 24109531 MLS

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every space has been curated with an uncompromising attention to detail-from custom millwork to premium finishes-creating an environment that is as functional as it is beautiful. Set on one of the most coveted streets in Southport, this property offers the perfect balance of privacy and proximity. Just a short stroll to the harbor and Long Island Sound, the setting recalls the charm of Nantucket or the Hamptons while retaining the unmistakable character of Southport. The transformation of the entire estate-including the main house, guest house, pool, and pool house-is nothing short of remarkable. The extensive list of upgrades and enhancements is too comprehensive to list here; this is a home that must be seen to be fully appreciated. Experience 260 Willow Street-a residence that invites you to live beautifully, entertain effortlessly, and enjoy the best of coastal village life.

260 Willow St, Fairfield

$11,895,000

Perched at the point of Saugatuck Island, Seven Sandpiper Road is pure New England perfection. The three story Nantucket style home is meticulously designed by architect Peter Cadoux to soak up the sparkling Long Island Sound views from all angles. The main floor holds the horizon directly at eye level from the open concept living areas - a light and bright gourmet kitchen with island seating, a breakfast nook and butler's pantry leads into the spacious family room with stone fireplace and deck access, but the show stopping sun room wins for best seat in the house where the floor to ceiling windows feel like the bow of a ship. The formal dining room also opens to the deck set for both lounging and grilling. In the primary wing, a breathtaking bedroom looks over the gorgeous grounds and water beyond, while the beautiful his and hers combined bath takes in the south facing Sound view. There are dual walk-in wardrobe closets as well as a second laundry closet. An stunning office rounds out the main floor, while the third floor holds a guest suite/media room with balcony and one of the most spectacular "roof" level decks in all of Westport! On the ground level, there are two bedrooms of generous size, each with their own ensuite bath and custom closets as well as a true library style office. Across the foyer, the cabana kitchenette and bath are conveniently located close to the pool and beach! Peaceful and private, the "backyard" consists of the covered grotto spilling right on

4 Beds ⋅ 6 Baths ⋅ 24167574 MLS

Perched at the point of Saugatuck Island, Seven Sandpiper Road is pure New England perfection. The three story Nantucket style home is meticulously designed by architect Peter Cadoux to soak up the sparkling Long Island Sound views from all angles. The main floor holds the horizon directly at eye level from the open concept living areas - a light and bright gourmet kitchen with island seating, a breakfast nook and butler's pantry leads into the spacious family room with stone fireplace and deck access, but the show stopping sun room wins for best seat in the house where the floor to ceiling windows feel like the bow of a ship. The formal dining room also opens to the deck set for both lounging and grilling. In the primary wing, a breathtaking bedroom looks over the gorgeous grounds and water beyond, while the beautiful his and hers combined bath takes in the south facing Sound view. There are dual walk-in wardrobe closets as well as a second laundry closet. An stunning office rounds out the main floor, while the third floor holds a guest suite/media room with balcony and one of the most spectacular "roof" level decks in all of Westport! On the ground level, there are two bedrooms of generous size, each with their own ensuite bath and custom closets as well as a true library style office. Across the foyer, the cabana kitchenette and bath are conveniently located close to the pool and beach! Peaceful and private, the "backyard" consists of the covered grotto spilling right on

7 Sandpiper Rd, Westport

$11,375,000

Nestled privately, and surrounded by matured trees, on 1.82 bucolic mid-country acres, sits this seven bedroom, seven full and three half bath, gorgeous estate! Extraordinary stone & shingle construction, built by Aberdeen Properties, and gardens magnificently designed by Rutherford & Associates. Dramatic front to back, double height entry, exquisite millwork throughout, 10' ceilings, and a comfortable open flow. Ideal for both everyday living and grand scale entertaining! Fabulous primary suite, with sitting area, plus five other spacious ensuite bedrooms, and a separate guest suite with f/p. Gourmet kitchen with sun-filled breakfast area and large pantry, formal dining room, family room, living room and magnificent office/library that is privately located at the end of the first floor. Finished lower level with gym/extra ensuite bedroom, another family/hang out room, home theater & spectacular wine room. Outside is a private, resort like oasis, with a large flagstone patio, fire pit, pizza oven, jacuzzi and a magnificent pool, overlooking the gorgeous manicured lawn! Minutes to shops, five-star restaurants, beaches, parks, train and major highways for an easy commute to NYC. Luxury, comfort, privacy and convenience...this one has it all!

7 Beds ⋅ 10 Baths ⋅ 24120527 MLS

Nestled privately, and surrounded by matured trees, on 1.82 bucolic mid-country acres, sits this seven bedroom, seven full and three half bath, gorgeous estate! Extraordinary stone & shingle construction, built by Aberdeen Properties, and gardens magnificently designed by Rutherford & Associates. Dramatic front to back, double height entry, exquisite millwork throughout, 10' ceilings, and a comfortable open flow. Ideal for both everyday living and grand scale entertaining! Fabulous primary suite, with sitting area, plus five other spacious ensuite bedrooms, and a separate guest suite with f/p. Gourmet kitchen with sun-filled breakfast area and large pantry, formal dining room, family room, living room and magnificent office/library that is privately located at the end of the first floor. Finished lower level with gym/extra ensuite bedroom, another family/hang out room, home theater & spectacular wine room. Outside is a private, resort like oasis, with a large flagstone patio, fire pit, pizza oven, jacuzzi and a magnificent pool, overlooking the gorgeous manicured lawn! Minutes to shops, five-star restaurants, beaches, parks, train and major highways for an easy commute to NYC. Luxury, comfort, privacy and convenience...this one has it all!

10 Copper Beech Rd, Greenwich

$11,000,000

Welcome to Mead Farm - exquisitely renovated and transformed midcountry Greenwich estate that blends historic character with modern luxury. Set on nearly 6 acres in a 2 acre zone, this 9,189 SF residence offers 6 bedrooms, 6 full and 2 half baths. A recent multi-year renovation by renowned designer Thom Filicia, paired with award-winning landscaping by James Doyle, elevates the property to a rare level of refinement, harmonizing timeless design with modern comfort. Originally built in 1846, the home features wide-plank floors, copper gutters, 7 fireplaces, and a wraparound porch. The rebuilt water tower adds a gym, wine room, full bath, and dramatic double-height office. Outdoors, enjoy gardens, terraces, pool with autocover, pond and a barn with loft and garages - just minutes from town.

6 Beds ⋅ 8 Baths ⋅ 24128794 MLS

Welcome to Mead Farm - exquisitely renovated and transformed midcountry Greenwich estate that blends historic character with modern luxury. Set on nearly 6 acres in a 2 acre zone, this 9,189 SF residence offers 6 bedrooms, 6 full and 2 half baths. A recent multi-year renovation by renowned designer Thom Filicia, paired with award-winning landscaping by James Doyle, elevates the property to a rare level of refinement, harmonizing timeless design with modern comfort. Originally built in 1846, the home features wide-plank floors, copper gutters, 7 fireplaces, and a wraparound porch. The rebuilt water tower adds a gym, wine room, full bath, and dramatic double-height office. Outdoors, enjoy gardens, terraces, pool with autocover, pond and a barn with loft and garages - just minutes from town.

411 Stanwich Rd, Greenwich

$11,000,000

Welcome to your dream home on Westport's premier Compo Beach cul-de-sac - an extraordinary 2+ acre estate offering privacy, luxury, and resort-style living in one of Fairfield County's most coveted coastal neighborhoods. Custom-built by Schmiedeck Construction with interiors by Havilande Whitcom Design, this modern farmhouse blends stunning architecture with high function and comfort. Steps from Longshore Club CC & Compo Beach, the home centers around a dramatic infinity-edge pool, expansive patios, sculpted parterres, outdoor kitchen, multi-level decks, and a large screened porch. Meticulously landscaped with fruit orchard, raised garden w/ fireside seating, sprawling lawns, ambient lighting, firepit - every detail was curated for elevated indoor-outdoor living. Inside, enjoy sleek, state-of-the-art finishes: a show-stopping primary suite with balcony and spa bath, and a walk-out LL with media room, wine cellar, rec room, gym, kitchenette, and pool bath w/ changing room. Flexible spaces incl separate guest quarters and au pair suite - ideal for multigenerational living. Smart systems, 3-stop elevator, LED lighting, generator and energy-efficient HVAC add comfort and convenience. Room for a TC or guesthouse, plus rare sub-dividable potential in one of Westport's most prestigious enclaves.

6 Beds ⋅ 9 Baths ⋅ 24130871 MLS

Welcome to your dream home on Westport's premier Compo Beach cul-de-sac - an extraordinary 2+ acre estate offering privacy, luxury, and resort-style living in one of Fairfield County's most coveted coastal neighborhoods. Custom-built by Schmiedeck Construction with interiors by Havilande Whitcom Design, this modern farmhouse blends stunning architecture with high function and comfort. Steps from Longshore Club CC & Compo Beach, the home centers around a dramatic infinity-edge pool, expansive patios, sculpted parterres, outdoor kitchen, multi-level decks, and a large screened porch. Meticulously landscaped with fruit orchard, raised garden w/ fireside seating, sprawling lawns, ambient lighting, firepit - every detail was curated for elevated indoor-outdoor living. Inside, enjoy sleek, state-of-the-art finishes: a show-stopping primary suite with balcony and spa bath, and a walk-out LL with media room, wine cellar, rec room, gym, kitchenette, and pool bath w/ changing room. Flexible spaces incl separate guest quarters and au pair suite - ideal for multigenerational living. Smart systems, 3-stop elevator, LED lighting, generator and energy-efficient HVAC add comfort and convenience. Room for a TC or guesthouse, plus rare sub-dividable potential in one of Westport's most prestigious enclaves.

39 Compo Pkwy, Westport

$10,300,000

Experience the unparalleled luxury of this exquisite Compo Beach seaside home,a masterpiece of design and craftsmanship, designed by renowned architect Peter Cadoux. Just steps from a private beach, this architectural gem is bathed in natural light and boasts breathtaking panoramic water views from nearly every room.The full chef's kitchen opens to a radiant sunroom with a glass ceiling, perfect for quietly enjoying the seaside ambiance. Entertain guests in the adjoining family room with a grand fireplace, the elegant dining room, and the striking music room all featuring wrap-around windows that showcase panoramic views of the Long Island Sound.The upstairs primary suite is a sanctuary with front and back balconies,a spa-like primary bath,an upstairs office and stunning views. Two additional bedrooms with a shared bath and a guest room with a private bath and balcony overlooking the Sound complete the second floor.The third floor offers two more bedrooms or flex space, a balcony overlooking the Sound, and a full bath.The exquisite craftsmanship continues on the lower level, a recreational paradise featuring a full gym, a lounge area with a fireplace, a media room, a pool table area with a bar, a fabulous wine room, and an extraordinary aquarium! Enjoy working from home in your private office or relax by the heated pool and spa. An outdoor kitchen enhances your charming and private backyard and also includes access to two tennis courts. Live every day like you're on vacation!

5 Beds ⋅ 8 Baths ⋅ 24134169 MLS

Experience the unparalleled luxury of this exquisite Compo Beach seaside home,a masterpiece of design and craftsmanship, designed by renowned architect Peter Cadoux. Just steps from a private beach, this architectural gem is bathed in natural light and boasts breathtaking panoramic water views from nearly every room.The full chef's kitchen opens to a radiant sunroom with a glass ceiling, perfect for quietly enjoying the seaside ambiance. Entertain guests in the adjoining family room with a grand fireplace, the elegant dining room, and the striking music room all featuring wrap-around windows that showcase panoramic views of the Long Island Sound.The upstairs primary suite is a sanctuary with front and back balconies,a spa-like primary bath,an upstairs office and stunning views. Two additional bedrooms with a shared bath and a guest room with a private bath and balcony overlooking the Sound complete the second floor.The third floor offers two more bedrooms or flex space, a balcony overlooking the Sound, and a full bath.The exquisite craftsmanship continues on the lower level, a recreational paradise featuring a full gym, a lounge area with a fireplace, a media room, a pool table area with a bar, a fabulous wine room, and an extraordinary aquarium! Enjoy working from home in your private office or relax by the heated pool and spa. An outdoor kitchen enhances your charming and private backyard and also includes access to two tennis courts. Live every day like you're on vacation!

260 Hillspoint Rd, Westport

$10,025,000

A rare opportunity to own a legacy estate that would command over $50 million to recreate in today's market. Orchard's End, built in 1929 designed by New York architect William B. Tubby, his outstanding designs include Waveny House in New Canaan, Dunnellen Hall in Greenwich and the William H. Childs House in Brooklyn. Beginning in 2014, the current owners retained world renowned architect Dinyar Wadia to embark on a 3-year 6 million dollar renovation perfecting the already expansive 10,000 square foot addition completed by the previous owners. Not only was the main residence improved and expanded upon a brand new 2,000 square foot 4-bedroom guest house, along with a custom designed 5,000 square foot wellness center, a custom pool with spa and new terraces transformed Orchard's End Estate into a true masterpiece. The main residence's addition includes a new kitchen, great room, outdoor courtyard, and study. Providing the inspiration for the great room was Castle Duart, located on the Isle of Mull and featured in the 1999 movie Entrapment in which Sean Connery and Catherina Zeta-Jones, playing art thieves, practice their moves for a high-tech heist. FURNISHED option available for separate pricing.

12 Beds ⋅ 16 Baths ⋅ 24084025 MLS

A rare opportunity to own a legacy estate that would command over $50 million to recreate in today's market. Orchard's End, built in 1929 designed by New York architect William B. Tubby, his outstanding designs include Waveny House in New Canaan, Dunnellen Hall in Greenwich and the William H. Childs House in Brooklyn. Beginning in 2014, the current owners retained world renowned architect Dinyar Wadia to embark on a 3-year 6 million dollar renovation perfecting the already expansive 10,000 square foot addition completed by the previous owners. Not only was the main residence improved and expanded upon a brand new 2,000 square foot 4-bedroom guest house, along with a custom designed 5,000 square foot wellness center, a custom pool with spa and new terraces transformed Orchard's End Estate into a true masterpiece. The main residence's addition includes a new kitchen, great room, outdoor courtyard, and study. Providing the inspiration for the great room was Castle Duart, located on the Isle of Mull and featured in the 1999 movie Entrapment in which Sean Connery and Catherina Zeta-Jones, playing art thieves, practice their moves for a high-tech heist. FURNISHED option available for separate pricing.

544 Oenoke Rdg, New Canaan

$10,000,000

Rarely does an opportunity arise to own a home in the coastal enclave of Shorehaven, and 10 Shorehaven Road is a true masterpiece. This Nantucket-inspired estate blends timeless elegance with relaxed coastal charm, offering unmatched luxury and tranquility. Set along the serene waterfront, the lush, landscaped grounds feature a sparkling pool, spa, and private dock-perfect for boating adventures or peaceful moments by the tide. Inside, a grand curved staircase greets you, leading to beautifully appointed spaces. Formal living and dining rooms offer sophistication, while the gourmet chef's kitchen and adjoining family room, with a coffered ceiling, fireplace, and French doors, invite effortless indoor-outdoor living. Five ensuite bedrooms, including the second-floor primary suite provide private retreats. The primary features two spa-like baths and a balcony with breathtaking water views. A custom office with its own balcony and a richly paneled study complete the home's refined interiors. Expansive windows flood the home with natural light, while the veranda, spanning the length of the house, is perfect for entertaining or quiet relaxation. Minutes from Shorehaven Golf Club and local amenities, this property offers the pinnacle of coastal living.

5 Beds ⋅ 10 Baths ⋅ 24172989 MLS

Rarely does an opportunity arise to own a home in the coastal enclave of Shorehaven, and 10 Shorehaven Road is a true masterpiece. This Nantucket-inspired estate blends timeless elegance with relaxed coastal charm, offering unmatched luxury and tranquility. Set along the serene waterfront, the lush, landscaped grounds feature a sparkling pool, spa, and private dock-perfect for boating adventures or peaceful moments by the tide. Inside, a grand curved staircase greets you, leading to beautifully appointed spaces. Formal living and dining rooms offer sophistication, while the gourmet chef's kitchen and adjoining family room, with a coffered ceiling, fireplace, and French doors, invite effortless indoor-outdoor living. Five ensuite bedrooms, including the second-floor primary suite provide private retreats. The primary features two spa-like baths and a balcony with breathtaking water views. A custom office with its own balcony and a richly paneled study complete the home's refined interiors. Expansive windows flood the home with natural light, while the veranda, spanning the length of the house, is perfect for entertaining or quiet relaxation. Minutes from Shorehaven Golf Club and local amenities, this property offers the pinnacle of coastal living.

10 Shorehaven Rd, Norwalk

$9,750,000

Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acres with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors, marble fireplaces and high ceilings. Dramatic double height entry leads into formal rooms with fireplaces, chef's kitchen with breakfast nook, family room with fireplace, library with wet bar and sunroom. Second floor boasts primary suite with balcony, walk-in closets; plus five bedrooms and four full baths. Play/rec room, gym, full bath and attached three-car garage complete lower level.

6 Beds ⋅ 8 Baths ⋅ 24091355 MLS

Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acres with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors, marble fireplaces and high ceilings. Dramatic double height entry leads into formal rooms with fireplaces, chef's kitchen with breakfast nook, family room with fireplace, library with wet bar and sunroom. Second floor boasts primary suite with balcony, walk-in closets; plus five bedrooms and four full baths. Play/rec room, gym, full bath and attached three-car garage complete lower level.

35 Club Rd, Greenwich

$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

$9,050,000

"Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of privacy, presence, and provenance. Designed in 1927 by renowned architect Francis Hamilton, the home was later owned by Broadway producer John C. Wilson and his partner, the celebrated English playwright Noel Coward. Over the years, "Pebbles" became a summer retreat for a remarkable circle of artists and tastemakers, including Vivien Leigh, Laurence Olivier, Diana Vreeland, Jean Schlumberger, and Richard Rodgers. Lovingly maintained and thoughtfully updated by each subsequent owner, the estate retains its grand-scale interiors, period details, and refined elegance. Expansive formal rooms, high ceilings, and sunlit living spaces open to terraces that overlook the water and the meticulously landscaped grounds, anchored by a striking pool featured in the 1968 film *The Swimmer* starring Burt Lancaster. This is more than a home-it's a rare opportunity to own a landmark property with architectural pedigree, cinematic history, and enduring coastal beauty-all within minutes of Southport Village, beaches, and NYC-bound trains.

6 Beds ⋅ 9 Baths ⋅ 24090854 MLS

"Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of privacy, presence, and provenance. Designed in 1927 by renowned architect Francis Hamilton, the home was later owned by Broadway producer John C. Wilson and his partner, the celebrated English playwright Noel Coward. Over the years, "Pebbles" became a summer retreat for a remarkable circle of artists and tastemakers, including Vivien Leigh, Laurence Olivier, Diana Vreeland, Jean Schlumberger, and Richard Rodgers. Lovingly maintained and thoughtfully updated by each subsequent owner, the estate retains its grand-scale interiors, period details, and refined elegance. Expansive formal rooms, high ceilings, and sunlit living spaces open to terraces that overlook the water and the meticulously landscaped grounds, anchored by a striking pool featured in the 1968 film *The Swimmer* starring Burt Lancaster. This is more than a home-it's a rare opportunity to own a landmark property with architectural pedigree, cinematic history, and enduring coastal beauty-all within minutes of Southport Village, beaches, and NYC-bound trains.

828 Sasco Hill Rd, Fairfield

$9,000,000

Modern Luxury New Construction residence sits on .78 acres combines privacy with elegant design. Moments from Greenwich Ave. built by an award winning builder. This home features soaring 10ft ceilings, light filled rooms, wide white-oak wood-floors throughout, and seamless indoor-outdoor living. A few highlights of many, are a Rooftop deck with Long Island Sound views that crowns the residence, a 3-car garage (+900 sq. Ft.) with 14-ft ceilings, and a serious top-of-the-line chef's kitchen. The Chef's kitchen features, Sub-Zero refrigeration,Wolf cooking, 2 sinks, and 2 dishwashers. A grand center island, Custom cabinetry, and thoughtful storage, providing effortless daily living and elevated entertaining. The primary suite offers a double-sided fireplace, creating a warm ambient enjoyed from both the bedroom and the spa-like bath. A private balcony extends the retreat, while the spa-inspired bathroom features a steam shower and radiant heated floors. 4 additional light filled en-suite bedrooms, share the same level, alongside a full laundry suite equipped with custom built-ins including steam/Iron drawer, a dry rack drawer, and stacked double washers and dryers. A 4-stop hydraulic elevator serves every level-from the versatile finished attic to a finished expansive lower level, you'll find a dedicated room for a gym, guest/au pair en-suite, and pre-wired theater/Golf simulator, ample space for a wine cellar, storage, and protected living space.

6 Beds ⋅ 9 Baths ⋅ 24127923 MLS

Modern Luxury New Construction residence sits on .78 acres combines privacy with elegant design. Moments from Greenwich Ave. built by an award winning builder. This home features soaring 10ft ceilings, light filled rooms, wide white-oak wood-floors throughout, and seamless indoor-outdoor living. A few highlights of many, are a Rooftop deck with Long Island Sound views that crowns the residence, a 3-car garage (+900 sq. Ft.) with 14-ft ceilings, and a serious top-of-the-line chef's kitchen. The Chef's kitchen features, Sub-Zero refrigeration,Wolf cooking, 2 sinks, and 2 dishwashers. A grand center island, Custom cabinetry, and thoughtful storage, providing effortless daily living and elevated entertaining. The primary suite offers a double-sided fireplace, creating a warm ambient enjoyed from both the bedroom and the spa-like bath. A private balcony extends the retreat, while the spa-inspired bathroom features a steam shower and radiant heated floors. 4 additional light filled en-suite bedrooms, share the same level, alongside a full laundry suite equipped with custom built-ins including steam/Iron drawer, a dry rack drawer, and stacked double washers and dryers. A 4-stop hydraulic elevator serves every level-from the versatile finished attic to a finished expansive lower level, you'll find a dedicated room for a gym, guest/au pair en-suite, and pre-wired theater/Golf simulator, ample space for a wine cellar, storage, and protected living space.

3 Anderson Rd, Greenwich

$9,000,000

NEWLY PRICED! Oversized 3.30 Private Waterfront Acres with 254 feet of Long Island Sound frontage located on the Premier Gold Coast of Connecticut is ready to be molded into your PERFECT Home... 26 Beachside Avenue is both a most sought after Westport address and NOW has over 254 feet of Direct Long Island Sound frontage. This southern facing, cleared, and elevated land is direct water front with private beach access as well as an expansive seawall. The possibilities are endless for this oversized lot. Transform these panoramic views into your perfect vision and start enjoying spectacular sunrises everyday. Located in the heart of Green Farms, Westport, walking distance to train station, close to schools and shopping. This lot is Builder Ready. Create Your Dream Today.

24035347 MLS

NEWLY PRICED! Oversized 3.30 Private Waterfront Acres with 254 feet of Long Island Sound frontage located on the Premier Gold Coast of Connecticut is ready to be molded into your PERFECT Home... 26 Beachside Avenue is both a most sought after Westport address and NOW has over 254 feet of Direct Long Island Sound frontage. This southern facing, cleared, and elevated land is direct water front with private beach access as well as an expansive seawall. The possibilities are endless for this oversized lot. Transform these panoramic views into your perfect vision and start enjoying spectacular sunrises everyday. Located in the heart of Green Farms, Westport, walking distance to train station, close to schools and shopping. This lot is Builder Ready. Create Your Dream Today.

26 Beachside Ave, Westport

$8,986,000

Like-new custom modern home with open-concept living designed for comfort and entertaining. The main level connects the family room, dining room, office, and chef's kitchen featuring Sub-Zero and Wolf appliances, invisible speakers, quartzite countertops, custom cabinetry, two large islands and multiple sliding glass doors leading to an outdoor oasis. The spacious pantry includes custom shelving, an ice maker, and built-in water dispenser. The primary suite features cathedral ceilings, gas fireplace, a private balcony, expansive walk-in closet, and a spa-inspired bath with radiant heated floors, steam shower, soaking tub, and wet bar with refrigerator. The second level also includes four additional en-suite bedrooms and a spacious laundry room with double washer and dryer and custom cabinetry. The third-floor lounge with wet bar and roof deck provides additional entertaining space along with another bedroom and full bath. The finished lower level offers a great room with wet bar, temperature-controlled wine room, gym, media/playroom, and en-suite guest bedroom. Outdoor spaces feature bluestone patios, a heated covered porch with fireplace, built-in grill, heated Gunite pool and spa and heated walkways. Additional highlights include Savant smart home system, Lutron lighting, whole-home audio, radiant heat, multi-zone HVAC, generator, and three-car garage with electric vehicle charger. Walk to Burying Hill Beach, Greens Farms Academy, and Greens Farms train station.

7 Beds ⋅ 9 Baths ⋅ 24158698 MLS

Like-new custom modern home with open-concept living designed for comfort and entertaining. The main level connects the family room, dining room, office, and chef's kitchen featuring Sub-Zero and Wolf appliances, invisible speakers, quartzite countertops, custom cabinetry, two large islands and multiple sliding glass doors leading to an outdoor oasis. The spacious pantry includes custom shelving, an ice maker, and built-in water dispenser. The primary suite features cathedral ceilings, gas fireplace, a private balcony, expansive walk-in closet, and a spa-inspired bath with radiant heated floors, steam shower, soaking tub, and wet bar with refrigerator. The second level also includes four additional en-suite bedrooms and a spacious laundry room with double washer and dryer and custom cabinetry. The third-floor lounge with wet bar and roof deck provides additional entertaining space along with another bedroom and full bath. The finished lower level offers a great room with wet bar, temperature-controlled wine room, gym, media/playroom, and en-suite guest bedroom. Outdoor spaces feature bluestone patios, a heated covered porch with fireplace, built-in grill, heated Gunite pool and spa and heated walkways. Additional highlights include Savant smart home system, Lutron lighting, whole-home audio, radiant heat, multi-zone HVAC, generator, and three-car garage with electric vehicle charger. Walk to Burying Hill Beach, Greens Farms Academy, and Greens Farms train station.

19 Beachside Cmn, Westport

$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

$8,750,000

This exquisite 7 bedroom & 11 bath residence set on 4.78 flat acres offers old world aesthetics with modern artistry. The craftsmanship of the millwork, finishes and features is unparalleled including reclaimed oak flooring imported from France and Hope's custom designed steel windows and doors. The living room w/fireplace leads to billiards room and sunroom w/access to back patio w/fireplace. The formal dining room includes custom designed hand painted Gracie wallpaper, and the open gourmet kitchen enjoys luxury appliances, eating area w/ fireplace, pantry, home office & French doors for a seamless indoor-outdoor flow. The family room has a soaring double-height ceiling surrounded by floor to ceiling windows, double doors & fireplace. The primary bedroom suite is a sanctuary on the second-floor w/double doors leading to terrace, two separate bathrooms w/dressing areas and walk in closets. There are 4 ensuite bedrooms, home office, study and laundry area on the second level. A playroom & media room occupy the top floor. The harmonious transition between interior and outdoors is facilitated by numerous access points, connecting the elegant indoor spaces to expansive outdoor spaces, including guest house/pool house leading out to the pool & spa with pergola. The lower level offers versatile space with golf simulator & putting green, bar area, gym/yoga studio, wine cellar & home theatre. Renovated barn w/inlay hardwood floor & sport court is next to tennis court. Prop in CT & NY

7 Beds ⋅ 11 Baths ⋅ 24084362 MLS

This exquisite 7 bedroom & 11 bath residence set on 4.78 flat acres offers old world aesthetics with modern artistry. The craftsmanship of the millwork, finishes and features is unparalleled including reclaimed oak flooring imported from France and Hope's custom designed steel windows and doors. The living room w/fireplace leads to billiards room and sunroom w/access to back patio w/fireplace. The formal dining room includes custom designed hand painted Gracie wallpaper, and the open gourmet kitchen enjoys luxury appliances, eating area w/ fireplace, pantry, home office & French doors for a seamless indoor-outdoor flow. The family room has a soaring double-height ceiling surrounded by floor to ceiling windows, double doors & fireplace. The primary bedroom suite is a sanctuary on the second-floor w/double doors leading to terrace, two separate bathrooms w/dressing areas and walk in closets. There are 4 ensuite bedrooms, home office, study and laundry area on the second level. A playroom & media room occupy the top floor. The harmonious transition between interior and outdoors is facilitated by numerous access points, connecting the elegant indoor spaces to expansive outdoor spaces, including guest house/pool house leading out to the pool & spa with pergola. The lower level offers versatile space with golf simulator & putting green, bar area, gym/yoga studio, wine cellar & home theatre. Renovated barn w/inlay hardwood floor & sport court is next to tennis court. Prop in CT & NY

358 Lukes Wood Rd, New Canaan

$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

$8,700,000

Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house. Dramatic interiors feature soaring ceilings, expansive windows, and multiple stone fireplaces that frame the natural beauty of the surrounding landscape. Generous living and entertaining spaces flow effortlessly to outdoor terraces and landscaped grounds designed for both relaxation and gathering. The property includes a waterside pool overlooking the water, a private dock for boating, and a gated driveway set among mature plantings that enhance the estate's sense of privacy. Additional amenities include the potential for an indoor pool and spa, offering an opportunity to further elevate the home's resort-like experience. A rare offering combining scale, versatility, and waterfront living in one of Westport's most sought-after coastal settings.

8 Beds ⋅ 10 Baths ⋅ 24159043 MLS

Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house. Dramatic interiors feature soaring ceilings, expansive windows, and multiple stone fireplaces that frame the natural beauty of the surrounding landscape. Generous living and entertaining spaces flow effortlessly to outdoor terraces and landscaped grounds designed for both relaxation and gathering. The property includes a waterside pool overlooking the water, a private dock for boating, and a gated driveway set among mature plantings that enhance the estate's sense of privacy. Additional amenities include the potential for an indoor pool and spa, offering an opportunity to further elevate the home's resort-like experience. A rare offering combining scale, versatility, and waterfront living in one of Westport's most sought-after coastal settings.

2 Judy Point Ln, Westport

$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

$8,650,000

Set on one of New Canaan's highest elevations, this iconic country estate offers a rare combination of architectural distinction, modern functionality, and understated luxury. Exquisitely restored by renowned architects Wadia Associates, the 14-room manor balances timeless design with contemporary ease. A grand reception hall introduces a sequence of formal rooms with soaring ceilings, curved glass windows, lacquered finishes, and classic French doors that open seamlessly to the outdoors. At the heart of the home, the Smallbone of Devizes kitchen with walls of Calacatta marble and top-tier appliances flows seamlessly into a light-filled family room overlooking four stunning sculpted acres. The primary wing, is a private retreat of more than 1,100 square feet, featuring a spa-style bath and expansive dressing room. Four additional en-suite bedrooms graciously complete the second floor with an additional spacious & sunny room/office on the third floor. Thoughtfully equipped as a smart home, the property places technology and convenience at your fingertips. Outside, landscaped grounds unfold with an expansive terrace, covered porch, heated pool, and cabana-an environment designed equally for quiet weekends or refined entertaining. Every detail reflects a commitment to craftsmanship and lifestyle, creating a residence that is both stately and livable. This is New Canaan at its most elevated-a rare opportunity to own a property where design, privacy, and comfort converge.

5 Beds ⋅ 8 Baths ⋅ 24125629 MLS

Set on one of New Canaan's highest elevations, this iconic country estate offers a rare combination of architectural distinction, modern functionality, and understated luxury. Exquisitely restored by renowned architects Wadia Associates, the 14-room manor balances timeless design with contemporary ease. A grand reception hall introduces a sequence of formal rooms with soaring ceilings, curved glass windows, lacquered finishes, and classic French doors that open seamlessly to the outdoors. At the heart of the home, the Smallbone of Devizes kitchen with walls of Calacatta marble and top-tier appliances flows seamlessly into a light-filled family room overlooking four stunning sculpted acres. The primary wing, is a private retreat of more than 1,100 square feet, featuring a spa-style bath and expansive dressing room. Four additional en-suite bedrooms graciously complete the second floor with an additional spacious & sunny room/office on the third floor. Thoughtfully equipped as a smart home, the property places technology and convenience at your fingertips. Outside, landscaped grounds unfold with an expansive terrace, covered porch, heated pool, and cabana-an environment designed equally for quiet weekends or refined entertaining. Every detail reflects a commitment to craftsmanship and lifestyle, creating a residence that is both stately and livable. This is New Canaan at its most elevated-a rare opportunity to own a property where design, privacy, and comfort converge.

561 Smith Ridge Rd, New Canaan

$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