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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

$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

$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

$11,000,000

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

$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

$8,700,000

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

$7,750,000

This exceptional Modern estate, originally crafted by Skyview as the builder's own residence, is available in as-new condition and enhanced by inspired customization. Set on 2+/- private acres in Coleytown, adjacent to the Paul Newman-Poses Nature Preserve, the home is approached by a long, gated drive that opens to a motorcourt ideal for grand entertaining. Triple-glazed Klar Studio windows frame the natural surroundings, creating a seamless indoor-outdoor connection. ICF construction, a lifetime Davinci roof & Viessmann boiler with radiant heat throughout ensure enduring quality. Tall ceilings, dramatic glass-lined stairs, curated lighting & a warm minimalist aesthetic define the interiors. The Great Room offers three exposures & the 1st of four fireplaces. The Miele-appointed kitchen features custom cabinetry & a pantry that flows to the dining rm w/illuminated ceil. The fam rm opens to a heated porch w/fireplace; the vast rear skylit porch leads to the pool, summer kitchen & spa. The finished LL now includes a gym, speakeasy-style pub & a kids climbing gym. Epic primary suite. Freshly painted and meticulously maintained throughout, offered in true move-in-ready condition. No new construction compares.

6 Beds ⋅ 8 Baths ⋅ 24136529 MLS

This exceptional Modern estate, originally crafted by Skyview as the builder's own residence, is available in as-new condition and enhanced by inspired customization. Set on 2+/- private acres in Coleytown, adjacent to the Paul Newman-Poses Nature Preserve, the home is approached by a long, gated drive that opens to a motorcourt ideal for grand entertaining. Triple-glazed Klar Studio windows frame the natural surroundings, creating a seamless indoor-outdoor connection. ICF construction, a lifetime Davinci roof & Viessmann boiler with radiant heat throughout ensure enduring quality. Tall ceilings, dramatic glass-lined stairs, curated lighting & a warm minimalist aesthetic define the interiors. The Great Room offers three exposures & the 1st of four fireplaces. The Miele-appointed kitchen features custom cabinetry & a pantry that flows to the dining rm w/illuminated ceil. The fam rm opens to a heated porch w/fireplace; the vast rear skylit porch leads to the pool, summer kitchen & spa. The finished LL now includes a gym, speakeasy-style pub & a kids climbing gym. Epic primary suite. Freshly painted and meticulously maintained throughout, offered in true move-in-ready condition. No new construction compares.

319 Bayberry Ln, Westport

$7,300,000

Introducing an exceptional new construction home by Redcoat Homes. Spanning over 8,000 square feet, this stunning property is situated on a flat, one-plus acre lot in the desirable Old Hill neighborhood of Westport. The location is private yet conveniently close to I-95 and the Merritt Parkway, just minutes from the beach and town. It also borders Earth Place, one of the top family-friendly hiking destinations in Connecticut. This beautiful six-bedroom home has been thoughtfully designed by renowned architect Judith Larson, showcasing impeccable taste throughout. The first level features a designer kitchen, a formal dining room, a spacious great room with a fireplace, and a large office with signature Redcoat oversized windows and doors. On the second level, you'll find five bedrooms, a laundry room, and a secondary office. The lower level includes a playroom, gym, sixth bedroom, and a wine room. The property also boasts a three-car garage, a gunite pool, and a full house generator for added convenience.

6 Beds ⋅ 7 Baths ⋅ 24064356 MLS

Introducing an exceptional new construction home by Redcoat Homes. Spanning over 8,000 square feet, this stunning property is situated on a flat, one-plus acre lot in the desirable Old Hill neighborhood of Westport. The location is private yet conveniently close to I-95 and the Merritt Parkway, just minutes from the beach and town. It also borders Earth Place, one of the top family-friendly hiking destinations in Connecticut. This beautiful six-bedroom home has been thoughtfully designed by renowned architect Judith Larson, showcasing impeccable taste throughout. The first level features a designer kitchen, a formal dining room, a spacious great room with a fireplace, and a large office with signature Redcoat oversized windows and doors. On the second level, you'll find five bedrooms, a laundry room, and a secondary office. The lower level includes a playroom, gym, sixth bedroom, and a wine room. The property also boasts a three-car garage, a gunite pool, and a full house generator for added convenience.

3 Tanglewood Ln, Westport

$7,000,000

109 Morningside Drive South is an exceptional and rare offering in the highly sought- after Greens Farms neighborhood in Westport CT. Spanning 12.3 acres, this expansive property presents a unique opportunity to create a one-of-a-kind estate in one of Fairfield county's most desirable locations. Nestled amongst prestigious homes, this property offers endless potential for those seeking to build something special. Whether you envision a grand single-family residence or a private compound, the parcel provides an extraordinary canvas for your vision.

24137565 MLS

109 Morningside Drive South is an exceptional and rare offering in the highly sought- after Greens Farms neighborhood in Westport CT. Spanning 12.3 acres, this expansive property presents a unique opportunity to create a one-of-a-kind estate in one of Fairfield county's most desirable locations. Nestled amongst prestigious homes, this property offers endless potential for those seeking to build something special. Whether you envision a grand single-family residence or a private compound, the parcel provides an extraordinary canvas for your vision.

109 Morningside Dr S, Westport

$6,750,000

Welcome to 27 Owenoke Park, a timeless direct waterfront retreat, offering sweeping views where history, nature and Long Island Sound converge. Tucked away from NYC's hustle, yet close enough to commute, Owenoke Park has always been one of Westport's most coveted neighborhoods. Set directly on the Long Island Sound shoreline with over 80' of water frontage, including private access to the tidal beach for boating and swimming, this New England Coastal Gambrel style home offers front-row seats to mesmerizing panoramic sunrises and sunsets, Compo Beach fireworks and beautiful existing gardens. Year-round, you'll marvel at the magnificent sights of birds soaring, fish jumping, and sailors and boaters gliding across the water. Take a stroll to Westport's Compo Beach or Marina to board your yacht at the dock, or paddle around Westport's Longshore Country Club for golf, tennis or sailing lessons. Nestled in a welcoming and picturesque community, you'll enjoy access to top-ranked schools and Westport's vibrant downtown, known for its exceptional dining, shopping and cultural experiences. 27 Owenoke Park isn't just a home-it's a lifestyle defined by natural beauty, a tight-knit community and the endless allure of Long Island Sound. Don't miss this rare opportunity to own a piece of Owenoke Park's legacy.

6 Beds ⋅ 4 Baths ⋅ 24150724 MLS

Welcome to 27 Owenoke Park, a timeless direct waterfront retreat, offering sweeping views where history, nature and Long Island Sound converge. Tucked away from NYC's hustle, yet close enough to commute, Owenoke Park has always been one of Westport's most coveted neighborhoods. Set directly on the Long Island Sound shoreline with over 80' of water frontage, including private access to the tidal beach for boating and swimming, this New England Coastal Gambrel style home offers front-row seats to mesmerizing panoramic sunrises and sunsets, Compo Beach fireworks and beautiful existing gardens. Year-round, you'll marvel at the magnificent sights of birds soaring, fish jumping, and sailors and boaters gliding across the water. Take a stroll to Westport's Compo Beach or Marina to board your yacht at the dock, or paddle around Westport's Longshore Country Club for golf, tennis or sailing lessons. Nestled in a welcoming and picturesque community, you'll enjoy access to top-ranked schools and Westport's vibrant downtown, known for its exceptional dining, shopping and cultural experiences. 27 Owenoke Park isn't just a home-it's a lifestyle defined by natural beauty, a tight-knit community and the endless allure of Long Island Sound. Don't miss this rare opportunity to own a piece of Owenoke Park's legacy.

27 Owenoke Park, Westport

$6,649,000

Now complete! Set on over 2 acres in one of Westports's most desired neighborhoods, this stunning new construction by HOBI award winner, Rick Benson, blends modern luxury with timeless design. Surrounded by mature trees, this home offers privacy & serenity minutes from trains, town, shopping & beaches. Discover luxurious living spaces, 6 ensuite bedrooms, 7 full/1 half baths, seamless flow between open-concept living & refined formal spaces. The gourmet kitchen is a chef's dream, featuring 60" Wolf range, Sub-Zero appliances, galley sink, fridge drawers, hidden shelves next to range, & a working pantry. Elevator-ready for 5 stops, the home is built for long term comfort. Entertain effortlessly in the family room containing a full wet bar with wine column & beverage center; the room opens to the covered porch & outdoor kitchen & dining area. The resort-style backyard is anchored by a 20'x40' foot pool with internal spa & sunning platform, looking over the extensive graceful lawn. The sumptuous primary suite is marked by vaulted ceiling, spacious deck with glass railings & wellness room. Additional highlights include 10" ft ceilings on the 1st floor, 9" on other floors, Lutron lighting, 2 instant hot water heaters, 4 gas fireplaces, fabulous walk-out lower level with full bar, gym, large gathering space & wine tasting area. Space exists for a 1000 sq ft ADU or 300 sq ft pool house, huge unfinished 3rd floor awaiting your ideas. Schedule your private tour today.

6 Beds ⋅ 8 Baths ⋅ 24102877 MLS

Now complete! Set on over 2 acres in one of Westports's most desired neighborhoods, this stunning new construction by HOBI award winner, Rick Benson, blends modern luxury with timeless design. Surrounded by mature trees, this home offers privacy & serenity minutes from trains, town, shopping & beaches. Discover luxurious living spaces, 6 ensuite bedrooms, 7 full/1 half baths, seamless flow between open-concept living & refined formal spaces. The gourmet kitchen is a chef's dream, featuring 60" Wolf range, Sub-Zero appliances, galley sink, fridge drawers, hidden shelves next to range, & a working pantry. Elevator-ready for 5 stops, the home is built for long term comfort. Entertain effortlessly in the family room containing a full wet bar with wine column & beverage center; the room opens to the covered porch & outdoor kitchen & dining area. The resort-style backyard is anchored by a 20'x40' foot pool with internal spa & sunning platform, looking over the extensive graceful lawn. The sumptuous primary suite is marked by vaulted ceiling, spacious deck with glass railings & wellness room. Additional highlights include 10" ft ceilings on the 1st floor, 9" on other floors, Lutron lighting, 2 instant hot water heaters, 4 gas fireplaces, fabulous walk-out lower level with full bar, gym, large gathering space & wine tasting area. Space exists for a 1000 sq ft ADU or 300 sq ft pool house, huge unfinished 3rd floor awaiting your ideas. Schedule your private tour today.

7 Roshab Ln, Westport

$6,550,000

Appraisers please take note: closing price does not fully represent offer price. **Sellers request all offers to be submitted by Sunday 6/28 at noon.** A WATERFRONT offering in one of Westport's most coveted enclaves. This beautifully composed estate is gracefully sited on more than two private, tree-lined acres, encompassing sweeping views of Sasco Creek, Southport Beach, and Long Island Sound while preserving an exceptional sense of seclusion. Designed to maximize its remarkable setting, the home captures water views from nearly every room and showcases timeless architectural details including custom millwork, random-width hardwood flooring, three fireplaces, cathedral ceilings, and formal and informal living spaces rarely seen in today's homes. Set amid beautifully landscaped grounds with perennial gardens and expansive entertaining terraces, this private oasis invites alfresco dining beneath breathtaking sunsets and sunrises. The home features five bedrooms including two primary suites, a guest suite, chef's kitchen, great room, sunroom, and more. Located between prestigious Beachside Avenue and historic Southport Village, you are moments from beaches, boutique shopping, acclaimed restaurants, and the enduring charm of Connecticut's Gold Coast. Framed by mature evergreens, flowering dogwoods, mountain laurel, and rhododendron, the property delivers an exceptional combination of privacy, scale, and proximity - just 55 miles from NY

5 Beds ⋅ 5 Baths ⋅ 24184591 MLS

Appraisers please take note: closing price does not fully represent offer price. **Sellers request all offers to be submitted by Sunday 6/28 at noon.** A WATERFRONT offering in one of Westport's most coveted enclaves. This beautifully composed estate is gracefully sited on more than two private, tree-lined acres, encompassing sweeping views of Sasco Creek, Southport Beach, and Long Island Sound while preserving an exceptional sense of seclusion. Designed to maximize its remarkable setting, the home captures water views from nearly every room and showcases timeless architectural details including custom millwork, random-width hardwood flooring, three fireplaces, cathedral ceilings, and formal and informal living spaces rarely seen in today's homes. Set amid beautifully landscaped grounds with perennial gardens and expansive entertaining terraces, this private oasis invites alfresco dining beneath breathtaking sunsets and sunrises. The home features five bedrooms including two primary suites, a guest suite, chef's kitchen, great room, sunroom, and more. Located between prestigious Beachside Avenue and historic Southport Village, you are moments from beaches, boutique shopping, acclaimed restaurants, and the enduring charm of Connecticut's Gold Coast. Framed by mature evergreens, flowering dogwoods, mountain laurel, and rhododendron, the property delivers an exceptional combination of privacy, scale, and proximity - just 55 miles from NY

6 Gray Ln, Westport

$6,219,419

Elegant new construction home by Mattera Construction sits on one of the most sought after streets with a cul-de-sac in Westport. Dramatic 5 Bedroom home offers 6 full baths and 2 half baths with room for a pool. An oversized custom Kitchen with Breakfast area, Family Room, Office, Living Room , Dining Room, Mudroom and 2 half baths complete the main level. On the 2nd level the oversized Primary Suite features 2 large closets and private bath. 4 more en-suite Bedroom/Baths plus a Laundry Room are also on the 2nd floor. The Lower Level additional Family Room, Gym and a Full Bath, plus a the finished 3rd level complete this special property. Custom details and finishes throughout! ROOM FOR POOL. Ready Summer of 2024

5 Beds ⋅ 8 Baths ⋅ 170584528 MLS

Elegant new construction home by Mattera Construction sits on one of the most sought after streets with a cul-de-sac in Westport. Dramatic 5 Bedroom home offers 6 full baths and 2 half baths with room for a pool. An oversized custom Kitchen with Breakfast area, Family Room, Office, Living Room , Dining Room, Mudroom and 2 half baths complete the main level. On the 2nd level the oversized Primary Suite features 2 large closets and private bath. 4 more en-suite Bedroom/Baths plus a Laundry Room are also on the 2nd floor. The Lower Level additional Family Room, Gym and a Full Bath, plus a the finished 3rd level complete this special property. Custom details and finishes throughout! ROOM FOR POOL. Ready Summer of 2024

5 Brookside Dr, Westport

$6,100,000

Looking for a sensational home just a short walk to the beach, Longshore, train, and restaurants in trendy Saugatuck? This exceptional home by Walter Mattera is a masterclass in blending traditional design with contemporary style. Expansive interiors feature grand gathering spaces that flow naturally into intimate retreats, creating a home equally suited for entertaining and everyday living. Thoughtfully designed across 4 floors, the home offers 5 bedrooms, 6 full/3 half baths. A gracious foyer opens to large scale living spaces, including an oversized kitchen with breakfast nook that connects seamlessly to the family room with a striking stone fireplace. Formal dining with butlers pantry, private office, and multiple indoor outdoor connections create a dynamic and inviting environment. The second level is highlighted by the luxurious primary suite featuring a fireplace, spa inspired bath, and boutique caliber closet designed as a calming retreat. Four additional en suite bedrooms, laundry, and bonus room complete the level. Third floor and walk out lower level recreation spaces reflect a modern approach to luxury where work, wellness, and entertainment coexist effortlessly. Outside, the chic and ethereal setting continues with a pool, spa, covered patio, fireplace, and expansive bluestone terrace that seamlessly integrate indoor and outdoor living. Every detail has been carefully considered to deliver comfort, sophistication, privacy, and connection to the best of Westport.

5 Beds ⋅ 9 Baths ⋅ 24175264 MLS

Looking for a sensational home just a short walk to the beach, Longshore, train, and restaurants in trendy Saugatuck? This exceptional home by Walter Mattera is a masterclass in blending traditional design with contemporary style. Expansive interiors feature grand gathering spaces that flow naturally into intimate retreats, creating a home equally suited for entertaining and everyday living. Thoughtfully designed across 4 floors, the home offers 5 bedrooms, 6 full/3 half baths. A gracious foyer opens to large scale living spaces, including an oversized kitchen with breakfast nook that connects seamlessly to the family room with a striking stone fireplace. Formal dining with butlers pantry, private office, and multiple indoor outdoor connections create a dynamic and inviting environment. The second level is highlighted by the luxurious primary suite featuring a fireplace, spa inspired bath, and boutique caliber closet designed as a calming retreat. Four additional en suite bedrooms, laundry, and bonus room complete the level. Third floor and walk out lower level recreation spaces reflect a modern approach to luxury where work, wellness, and entertainment coexist effortlessly. Outside, the chic and ethereal setting continues with a pool, spa, covered patio, fireplace, and expansive bluestone terrace that seamlessly integrate indoor and outdoor living. Every detail has been carefully considered to deliver comfort, sophistication, privacy, and connection to the best of Westport.

28 Ferry Ln E, Westport

$5,995,000

Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak floors, soaring ceilings, and custom Italian cabinetry create a warm and sophisticated interior. The chef's kitchen features L'Ottocento cabinetry, Thermador appliances, and Compac Quartz surfaces, complemented by a fully equipped butler's pantry with a second dishwasher and wine refrigeration. An open-concept family room with a sleek linear gas fireplace flows seamlessly to the covered outdoor terrace overlooking the heated pool and landscaped grounds-perfect for both quiet evenings and entertaining. Upstairs, vaulted bedrooms include fully furnished custom closets. A sun-filled lounge opens to a private rooftop deck with a gas fireplace and seasonal views of Long Island Sound. The primary suite offers a private terrace, dual walk-in closets with custom Italian millwork, and a spa-inspired bath designed for relaxation. Set moments from the shoreline while offering easy access to Manhattan via train, this newly completed residence presents a rare opportunity to enjoy modern coastal living in one of Westport's most desirable neighborhoods.

5 Beds ⋅ 5 Baths ⋅ 24158799 MLS

Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak floors, soaring ceilings, and custom Italian cabinetry create a warm and sophisticated interior. The chef's kitchen features L'Ottocento cabinetry, Thermador appliances, and Compac Quartz surfaces, complemented by a fully equipped butler's pantry with a second dishwasher and wine refrigeration. An open-concept family room with a sleek linear gas fireplace flows seamlessly to the covered outdoor terrace overlooking the heated pool and landscaped grounds-perfect for both quiet evenings and entertaining. Upstairs, vaulted bedrooms include fully furnished custom closets. A sun-filled lounge opens to a private rooftop deck with a gas fireplace and seasonal views of Long Island Sound. The primary suite offers a private terrace, dual walk-in closets with custom Italian millwork, and a spa-inspired bath designed for relaxation. Set moments from the shoreline while offering easy access to Manhattan via train, this newly completed residence presents a rare opportunity to enjoy modern coastal living in one of Westport's most desirable neighborhoods.

22 Apple Tree Trl, Westport

$5,945,000

Custom built by Mattera Construction, this exceptional home offers over 11,000 sq ft+/- of refined living on 1.3 private acres in the highly sought-after Sturges Commons neighborhood, known for its strong sense of community and block gatherings. Recently enhanced w/ a brand-new, top-of-the-line cedar wood roof, the home blends timeless craftsmanship w/ modern luxury. The main level is ideal for both elegant entertaining & everyday living, featuring a chef's kitchen with Wolf/Subzero appliances, an inviting family room w/ fireplace, a richly detailed library w/ custom cabinetry, a gracious living room, & large sun filled dining room that can comfortably accommodate 12. Upstairs, the luxurious primary suite features architectural ceilings, fireplace, a stunning dressing room, a spa-like bath, & private study. Four additional en-suite bedrooms & a second family room complete the level. The third floor offers a large playroom w/ a walk-in closet & full bath. The walk-out lower level delivers exceptional recreation w/ a private theater, gym, & multiple spaces for games, crafts, & entertaining. Outdoor living rivals a resort, featuring a pool w/ spa, covered terrace w/ fireplace, outdoor kitchen w/ BBQ, & a full-size sport court. A rare opportunity to own a thoughtfully designed home offering scale, comfort, & lifestyle in one of Westport's most desirable neighborhoods. Minutes from all amenities yet situated on a lot with exceptional privacy, this home is not to be missed!

6 Beds ⋅ 9 Baths ⋅ 24146477 MLS

Custom built by Mattera Construction, this exceptional home offers over 11,000 sq ft+/- of refined living on 1.3 private acres in the highly sought-after Sturges Commons neighborhood, known for its strong sense of community and block gatherings. Recently enhanced w/ a brand-new, top-of-the-line cedar wood roof, the home blends timeless craftsmanship w/ modern luxury. The main level is ideal for both elegant entertaining & everyday living, featuring a chef's kitchen with Wolf/Subzero appliances, an inviting family room w/ fireplace, a richly detailed library w/ custom cabinetry, a gracious living room, & large sun filled dining room that can comfortably accommodate 12. Upstairs, the luxurious primary suite features architectural ceilings, fireplace, a stunning dressing room, a spa-like bath, & private study. Four additional en-suite bedrooms & a second family room complete the level. The third floor offers a large playroom w/ a walk-in closet & full bath. The walk-out lower level delivers exceptional recreation w/ a private theater, gym, & multiple spaces for games, crafts, & entertaining. Outdoor living rivals a resort, featuring a pool w/ spa, covered terrace w/ fireplace, outdoor kitchen w/ BBQ, & a full-size sport court. A rare opportunity to own a thoughtfully designed home offering scale, comfort, & lifestyle in one of Westport's most desirable neighborhoods. Minutes from all amenities yet situated on a lot with exceptional privacy, this home is not to be missed!

29 Sturges Commons, Westport

$5,899,000

The home of your dreams that exceeds every expectation awaits at this spectacular, like-new residence built w/the finest quality & elevated design. Perfectly sited on one of Long Lots' top cul-de-sacs behind a stone wall, the manicured acre w/saltwater gunite pool/spa offers a serene backdrop for this exceptional property. The impressive, soaring foyer w/exquisite millwork introduces interiors w/ 10-ft ceilings on the main level incl the grand LR w/modern marble fpl & DR w/architectural ceiling. Well-appointed library/home office w/built-ins, fireplace & French doors to side & rear porches. The show-stopping chef's kitchen dazzles w/custom cabinetry, marble counters & island, backsplash w/subtle bronze inlay, Sub Zero & Wolf appliances, walk-in pantry, butler's pantry to DR & sunlit dining area, flowing into the stunning fam rm w/French doors & gorgeous fireplace. Expansive rear hall w/full pool bath, mudroom w/ample storage, 3-car garage access, back stairs to 2nd & 3rd flrs. With 7 BRs, 8 full & 2 half baths, there is space for all. Luxe primary suite w/spacious BR, sitting area w/fpl, dressing rm, coffee bar, 2 incredible walk-in clsts, marble bath. Bonus rms on 2nd flr w/built-ins & 3rd flr w/climbing structure. Incredible LL w/media rm, gym, wine cellar, bar, game rm w/fpl, sauna. Resort-style property w/covered porch, pergola, firepit, outdoor kitchen & level lawns framing the 45-ft pool. Generator, Savant smart home system & much more. Impeccable & move-in ready.

7 Beds ⋅ 10 Baths ⋅ 24130004 MLS

The home of your dreams that exceeds every expectation awaits at this spectacular, like-new residence built w/the finest quality & elevated design. Perfectly sited on one of Long Lots' top cul-de-sacs behind a stone wall, the manicured acre w/saltwater gunite pool/spa offers a serene backdrop for this exceptional property. The impressive, soaring foyer w/exquisite millwork introduces interiors w/ 10-ft ceilings on the main level incl the grand LR w/modern marble fpl & DR w/architectural ceiling. Well-appointed library/home office w/built-ins, fireplace & French doors to side & rear porches. The show-stopping chef's kitchen dazzles w/custom cabinetry, marble counters & island, backsplash w/subtle bronze inlay, Sub Zero & Wolf appliances, walk-in pantry, butler's pantry to DR & sunlit dining area, flowing into the stunning fam rm w/French doors & gorgeous fireplace. Expansive rear hall w/full pool bath, mudroom w/ample storage, 3-car garage access, back stairs to 2nd & 3rd flrs. With 7 BRs, 8 full & 2 half baths, there is space for all. Luxe primary suite w/spacious BR, sitting area w/fpl, dressing rm, coffee bar, 2 incredible walk-in clsts, marble bath. Bonus rms on 2nd flr w/built-ins & 3rd flr w/climbing structure. Incredible LL w/media rm, gym, wine cellar, bar, game rm w/fpl, sauna. Resort-style property w/covered porch, pergola, firepit, outdoor kitchen & level lawns framing the 45-ft pool. Generator, Savant smart home system & much more. Impeccable & move-in ready.

9 Burr Farms Rd, Westport

$5,775,000

Experience the pinnacle of Compo Beach living at 9 Pond Edge Road, a rare coastal sanctuary offering immediate beach access with the peace of mind of an elevated, flood-safe setting. Spanning 6,100 square feet across four impeccably finished levels, this 6-bedroom home is designed for effortless entertaining and everyday relaxation. Sunlight fills the open great room (with WBF) and dining area, where a wall of French doors opens to a private backyard oasis featuring a heated gunite pool, stone patio, and built-in BBQ, all surrounded by mature landscaping. A cozy living room with a gas fireplace provides the perfect setting for intimate gatherings or quiet evenings at home. At the heart of the home is the eat-in Chef's Kitchen, complete with luxury appliances, two dishwashers, three ovens, and an oversized center island. A flexible main-level suite offers ideal space for an executive office or guest accommodations. The second floor showcases a serene primary suite with a gas fireplace, dual dressing rooms, and a spa-inspired bath, along with three additional en-suite bedrooms and a laundry room. The third level features a secluded guest suite with private balcony and a skylight-filled bath. The lower level is a destination of its own, offering a home theater, dedicated gym, recreation room, and full bath with direct access to the pool. Complete with a whole-home generator and attached garage, this turn-key property delivers laid-back luxury just moments from the sand.

6 Beds ⋅ 7 Baths ⋅ 24143533 MLS

Experience the pinnacle of Compo Beach living at 9 Pond Edge Road, a rare coastal sanctuary offering immediate beach access with the peace of mind of an elevated, flood-safe setting. Spanning 6,100 square feet across four impeccably finished levels, this 6-bedroom home is designed for effortless entertaining and everyday relaxation. Sunlight fills the open great room (with WBF) and dining area, where a wall of French doors opens to a private backyard oasis featuring a heated gunite pool, stone patio, and built-in BBQ, all surrounded by mature landscaping. A cozy living room with a gas fireplace provides the perfect setting for intimate gatherings or quiet evenings at home. At the heart of the home is the eat-in Chef's Kitchen, complete with luxury appliances, two dishwashers, three ovens, and an oversized center island. A flexible main-level suite offers ideal space for an executive office or guest accommodations. The second floor showcases a serene primary suite with a gas fireplace, dual dressing rooms, and a spa-inspired bath, along with three additional en-suite bedrooms and a laundry room. The third level features a secluded guest suite with private balcony and a skylight-filled bath. The lower level is a destination of its own, offering a home theater, dedicated gym, recreation room, and full bath with direct access to the pool. Complete with a whole-home generator and attached garage, this turn-key property delivers laid-back luxury just moments from the sand.

9 Pond Edge Rd, Westport

$5,700,000

Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a pool with spa, expansive lounging areas, full outdoor kitchen, and a rare post-tension concrete tennis court - the premier surface used at elite clubs and college facilities. A truly extraordinary amenity rarely found in residential homes. The home offers an open floor plan filled with natural light and thoughtfully designed spaces. The gourmet chef's kitchen features high-end appliances, abundant workspace, and two dishwashers. Main-level highlights include elegant entertaining spaces, a private meditation room, and seamless indoor-outdoor flow. The primary suite is a retreat with a spa-inspired bath, steam shower, and dressing room with abundant closets. Upstairs, an incredible playroom with six built-in beds creates the perfect sleepover space or playroom. The walk-out lower level offers versatility with a media room, gym, office, and guest suite ideal for extended family, au pair, or guests. Rarely does a Westport luxury home offer resort-style amenities, premier tennis facilities, flexible living space, and walk-to-school convenience in such a private setting.

6 Beds ⋅ 7 Baths ⋅ 24168601 MLS

Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a pool with spa, expansive lounging areas, full outdoor kitchen, and a rare post-tension concrete tennis court - the premier surface used at elite clubs and college facilities. A truly extraordinary amenity rarely found in residential homes. The home offers an open floor plan filled with natural light and thoughtfully designed spaces. The gourmet chef's kitchen features high-end appliances, abundant workspace, and two dishwashers. Main-level highlights include elegant entertaining spaces, a private meditation room, and seamless indoor-outdoor flow. The primary suite is a retreat with a spa-inspired bath, steam shower, and dressing room with abundant closets. Upstairs, an incredible playroom with six built-in beds creates the perfect sleepover space or playroom. The walk-out lower level offers versatility with a media room, gym, office, and guest suite ideal for extended family, au pair, or guests. Rarely does a Westport luxury home offer resort-style amenities, premier tennis facilities, flexible living space, and walk-to-school convenience in such a private setting.

6 Twin Circle Dr, Westport

$5,500,000

Stunning 6 Bedroom 9600SF (including all 4 levels) Colonial in the heart of Westport. Built by Bluewater Home Builders, this stunning custom residence is situated on a private cul-de-sac in the central Hunt Club area. The traditional design boasts exceptional interior details, including soaring ceilings, beamed and coffered accents, shiplap paneling, and sleek millwork throughout all finished levels. The state-of-the-art gourmet Kitchen flows seamlessly into the grand Family Room, both opening to a covered bluestone patio featuring a fireplace, remote-controlled phantom screens, and a built-in outdoor kitchen-perfect for entertaining.The 1st floor office also opens to the peaceful yard and Patio. A 20'x45' saltwater Pool with automatic cover and sun ledge add a resort-like touch, complemented by mature landscaping, a koi pond, multiple gathering areas and a fire pit. Luxurious Primary Suite offers a soaring 11' ceilings, a fireplace, dressing/sitting room, and a marble spa bath. Five additional en-suite Bedrooms provide ample space for family and guests. The finished Lower Level includes a Game Room, Media Room with stadium seating, Gym, Wine Center and an 6th Bedroom. Finished 3rd floor offers bunk beds for sleep overs, a stage, an art area, lounge,cedar closet & abundant storage. Modern amenities include a generator and Lutron lighting system throughout. Located on a perfect acre, this home combines elegance, comfort, and convenience-just moments from all Westport amenity.

6 Beds ⋅ 9 Baths ⋅ 24131564 MLS

Stunning 6 Bedroom 9600SF (including all 4 levels) Colonial in the heart of Westport. Built by Bluewater Home Builders, this stunning custom residence is situated on a private cul-de-sac in the central Hunt Club area. The traditional design boasts exceptional interior details, including soaring ceilings, beamed and coffered accents, shiplap paneling, and sleek millwork throughout all finished levels. The state-of-the-art gourmet Kitchen flows seamlessly into the grand Family Room, both opening to a covered bluestone patio featuring a fireplace, remote-controlled phantom screens, and a built-in outdoor kitchen-perfect for entertaining.The 1st floor office also opens to the peaceful yard and Patio. A 20'x45' saltwater Pool with automatic cover and sun ledge add a resort-like touch, complemented by mature landscaping, a koi pond, multiple gathering areas and a fire pit. Luxurious Primary Suite offers a soaring 11' ceilings, a fireplace, dressing/sitting room, and a marble spa bath. Five additional en-suite Bedrooms provide ample space for family and guests. The finished Lower Level includes a Game Room, Media Room with stadium seating, Gym, Wine Center and an 6th Bedroom. Finished 3rd floor offers bunk beds for sleep overs, a stage, an art area, lounge,cedar closet & abundant storage. Modern amenities include a generator and Lutron lighting system throughout. Located on a perfect acre, this home combines elegance, comfort, and convenience-just moments from all Westport amenity.

10 Debra Ln, Westport

$5,450,000

Experience refined coastal living in this exceptional hilltop residence, just a short walk to Compo Beach. Built by celebrated Bluewater Home Builders, this stunning Nantucket-style home set on a rare & secluded .92-acre property on a quiet cul-de-sac is ideally positioned on one of the area's most prestigious & sought-after streets, offering an unparalleled blend of privacy & lifestyle. This home is surrounded by beautiful landscaped grounds and features a gunite pool, spa & water views of Mill Pond. Spanning 4 finished levels, the home offers 6 bedrooms, 7 baths, including 2 home offices-perfect for today's lifestyle. The grand foyer leads to the Dining Room with Butler's Pantry and the Living Room with fireplace. At the heart of the home is the Gourmet Kitchen with upscale appliances and an open floor plan to the Family Room. There is a screened in 3 season porch off the kitchen. On the second floor the luxurious Primary Suite features its own private office and a 2nd floor balcony with water views. 3 additional bedrooms are ensuite. A private third floor offers a bedroom, full bath and balcony ideal for guests, family or a secluded work space. The finished above ground walk-out lower level to the pool/patio is designed for both relaxation and fun, complete with a Playroom, Exercise Room, Bedroom, Full Bath, Wine Cellar, second laundry area and extensive storage. There is a full house generator. NO flood insurance is needed. Minutes to train station. Vacation year round.

6 Beds ⋅ 7 Baths ⋅ 24168754 MLS

Experience refined coastal living in this exceptional hilltop residence, just a short walk to Compo Beach. Built by celebrated Bluewater Home Builders, this stunning Nantucket-style home set on a rare & secluded .92-acre property on a quiet cul-de-sac is ideally positioned on one of the area's most prestigious & sought-after streets, offering an unparalleled blend of privacy & lifestyle. This home is surrounded by beautiful landscaped grounds and features a gunite pool, spa & water views of Mill Pond. Spanning 4 finished levels, the home offers 6 bedrooms, 7 baths, including 2 home offices-perfect for today's lifestyle. The grand foyer leads to the Dining Room with Butler's Pantry and the Living Room with fireplace. At the heart of the home is the Gourmet Kitchen with upscale appliances and an open floor plan to the Family Room. There is a screened in 3 season porch off the kitchen. On the second floor the luxurious Primary Suite features its own private office and a 2nd floor balcony with water views. 3 additional bedrooms are ensuite. A private third floor offers a bedroom, full bath and balcony ideal for guests, family or a secluded work space. The finished above ground walk-out lower level to the pool/patio is designed for both relaxation and fun, complete with a Playroom, Exercise Room, Bedroom, Full Bath, Wine Cellar, second laundry area and extensive storage. There is a full house generator. NO flood insurance is needed. Minutes to train station. Vacation year round.

32 Burnham Hl, Westport

$5,396,000

Elegant new construction home by Mattera Construction sits in the middle of one of the most centrally located neighborhoods in Westport. Dramatic 6 Bedroom home, features an inground Gunite Pool, while offering 6 full baths and 3 half baths on 4 finished levels. An oversized custom Kitchen with Breakfast area, Family Room, Office, Living Room , Dining Room, Mudroom and 2 half baths complete the main level. On the 2nd level the oversized Primary Suite features 2 large walk in closets and a private bath. 4 more en-suite Bedrooms and Baths plus a Laundry Room are also on the 2nd floor. The Lower Level boasts an additional Family Room, Gym and a Bedroom with Full Bath. The finished 3rd level offers an additional Playroom or Office plus a half bath. Custom details and finishes throughout!

6 Beds ⋅ 9 Baths ⋅ 170618303 MLS

Elegant new construction home by Mattera Construction sits in the middle of one of the most centrally located neighborhoods in Westport. Dramatic 6 Bedroom home, features an inground Gunite Pool, while offering 6 full baths and 3 half baths on 4 finished levels. An oversized custom Kitchen with Breakfast area, Family Room, Office, Living Room , Dining Room, Mudroom and 2 half baths complete the main level. On the 2nd level the oversized Primary Suite features 2 large walk in closets and a private bath. 4 more en-suite Bedrooms and Baths plus a Laundry Room are also on the 2nd floor. The Lower Level boasts an additional Family Room, Gym and a Bedroom with Full Bath. The finished 3rd level offers an additional Playroom or Office plus a half bath. Custom details and finishes throughout!

19 Joann Cir, Westport

$5,375,000

A RARE SECOND CHANCE. This estate drew multiple offers within days, then sellers pressed pause. With plans now finalized, it's back on the market. Charming. Unique. Soulful. These are the words the current owner uses to describe this exceptional estate-and from the moment you arrive, you'll understand why. Poised on 2.85 private acres, this exceptional estate seamlessly weaves timeless heritage with modern luxury. At its core: a preserved 1930 Frazier Peters stone cottage-now a 2-bed, 2-bath guest house. At its heart: a 2007 custom-built main residence by Coastal Construction, echoing Peters' signature stonework with scale and sophistication. Step inside and you'll understand why guests so often say, "Every room tells a story." A just-completed interior redesign has curated every finish, light fixture, and wall covering to create warmth and quiet elegance. The flow between rooms is not just open-it's meaningful, revealing itself gradually like a favorite novel. The barrel-ceilinged primary suite, sunlit kitchen, cozy living room, hidden reading nooks, and versatile third-floor retreat all invite you to live more slowly, more beautifully. A gym, media room, and music studio offer space to move, create, and unwind. Outside, a pool/spa, pool house, and terrace with fireplace and outdoor kitchen extend the experience. Offered fully furnished at an additional cost if desired. Where every detail invites you to live with intention, comfort and quiet luxury.

7 Beds ⋅ 9 Baths ⋅ 24112473 MLS

A RARE SECOND CHANCE. This estate drew multiple offers within days, then sellers pressed pause. With plans now finalized, it's back on the market. Charming. Unique. Soulful. These are the words the current owner uses to describe this exceptional estate-and from the moment you arrive, you'll understand why. Poised on 2.85 private acres, this exceptional estate seamlessly weaves timeless heritage with modern luxury. At its core: a preserved 1930 Frazier Peters stone cottage-now a 2-bed, 2-bath guest house. At its heart: a 2007 custom-built main residence by Coastal Construction, echoing Peters' signature stonework with scale and sophistication. Step inside and you'll understand why guests so often say, "Every room tells a story." A just-completed interior redesign has curated every finish, light fixture, and wall covering to create warmth and quiet elegance. The flow between rooms is not just open-it's meaningful, revealing itself gradually like a favorite novel. The barrel-ceilinged primary suite, sunlit kitchen, cozy living room, hidden reading nooks, and versatile third-floor retreat all invite you to live more slowly, more beautifully. A gym, media room, and music studio offer space to move, create, and unwind. Outside, a pool/spa, pool house, and terrace with fireplace and outdoor kitchen extend the experience. Offered fully furnished at an additional cost if desired. Where every detail invites you to live with intention, comfort and quiet luxury.

9 Greenbrier Rd, Westport

$5,300,000

An impeccable home in an incredible location! Just a stone's throw to Compo Beach, Ned Dimes Marina and Longshore Club Park, this gorgeous 4 bedroom, 4.5 bath modern Colonial with a pool is beach neighborhood perfection. The main floor is beautifully arranged, the family, dining area and kitchen span the back of the house creating a great room - with French doors to the patio and pool just beyond. The gorgeous kitchen is down in white oak, with a massive island, top appliances and smart storage. Gorgeous custom details throughout include built ins, dramatic modern millwork, sleek fireplaces and high end stone surfaces plus an elevator. Upstairs, the primary suite is a dream - a bright and airy bedroom, two walk in closets, and an oversized bath with soaking tub, steam shower and radient flooring. There are two additional bedrooms on the second floor, plus an office and laundry room. The third floor holds a bedroom and full bath. Tucked on a quiet side street steps to the water and all the Compo/Longshore area amenities like beach, boating, golf and tennis, while also being just a quick ride into town or to the train!

4 Beds ⋅ 5 Baths ⋅ 24174513 MLS

An impeccable home in an incredible location! Just a stone's throw to Compo Beach, Ned Dimes Marina and Longshore Club Park, this gorgeous 4 bedroom, 4.5 bath modern Colonial with a pool is beach neighborhood perfection. The main floor is beautifully arranged, the family, dining area and kitchen span the back of the house creating a great room - with French doors to the patio and pool just beyond. The gorgeous kitchen is down in white oak, with a massive island, top appliances and smart storage. Gorgeous custom details throughout include built ins, dramatic modern millwork, sleek fireplaces and high end stone surfaces plus an elevator. Upstairs, the primary suite is a dream - a bright and airy bedroom, two walk in closets, and an oversized bath with soaking tub, steam shower and radient flooring. There are two additional bedrooms on the second floor, plus an office and laundry room. The third floor holds a bedroom and full bath. Tucked on a quiet side street steps to the water and all the Compo/Longshore area amenities like beach, boating, golf and tennis, while also being just a quick ride into town or to the train!

15 Roosevelt Rd, Westport

$5,199,000

Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living with a Westport nostalgic feel. This 7,000+ square-foot home showcases unparalleled design and meticulous construction across two main levels that optimize light and space. Redcoat homes construction is several grades above spec builders, attention to detail , light, and space that work for today's living are imperative in his homes. The main level features a designer kitchen, formal dining room, family room, office, and living room. An additional laundry and changing room are on the first floor. Enhanced by Redcoat's signature oversized windows, doors, and 10-foot ceilings. The second level boasts 4 bedrooms, including a luxurious primary suite, along with the main laundry area. The third floor includes an additional family space and an office. The lower level includes a sixth bedroom, gym, and playroom. Additional amenities comprise: a three-car garage, an approved pool site.

6 Beds ⋅ 7 Baths ⋅ 24165045 MLS

Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living with a Westport nostalgic feel. This 7,000+ square-foot home showcases unparalleled design and meticulous construction across two main levels that optimize light and space. Redcoat homes construction is several grades above spec builders, attention to detail , light, and space that work for today's living are imperative in his homes. The main level features a designer kitchen, formal dining room, family room, office, and living room. An additional laundry and changing room are on the first floor. Enhanced by Redcoat's signature oversized windows, doors, and 10-foot ceilings. The second level boasts 4 bedrooms, including a luxurious primary suite, along with the main laundry area. The third floor includes an additional family space and an office. The lower level includes a sixth bedroom, gym, and playroom. Additional amenities comprise: a three-car garage, an approved pool site.

36 Maple Ave S, Westport

$5,150,000

Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is a new construction lux home from CCO Habitats. 3 levels of finished living space with 10 foot ceilings on the 1st floor give an amazing sense of openness, as well as better functionality than 4 level homes. Think about it. Who really wants to walk up to the third floor every day? That's right; no one. And you don't want anyone walking past your bedroom to get to a finished third floor either. The family bedroom floor should be private. Wider homes are much more desirable & functional than taller homes. The home has a generous first floor guest bedroom & full bath. Much better. It's not just for grandma you know, although she will love it. Who knows when you're going to tear your meniscus or ACL?? Pickleball hurts! :) Or - it's a great, convenient play room for little ones. Or a gamers' paradise for the older set. #Choices. We also have two designated offices; one on the first floor & a second in a private wing with its own staircase on the second floor. Three wet bars and a dry bar. Custom cabinetry & built-ins throughout. There's a 20x40 salt water pool. Oversized, tilting European windows & sliders drench the home in natural light. Organic modern; warm & functional. A true walk out lower level that easily doubles as a pool house with a full bath, second laundry and entertaining spaces. A full house generator and even an EV outlet. It's all here. Come visit. Come home

6 Beds ⋅ 8 Baths ⋅ 24177071 MLS

Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is a new construction lux home from CCO Habitats. 3 levels of finished living space with 10 foot ceilings on the 1st floor give an amazing sense of openness, as well as better functionality than 4 level homes. Think about it. Who really wants to walk up to the third floor every day? That's right; no one. And you don't want anyone walking past your bedroom to get to a finished third floor either. The family bedroom floor should be private. Wider homes are much more desirable & functional than taller homes. The home has a generous first floor guest bedroom & full bath. Much better. It's not just for grandma you know, although she will love it. Who knows when you're going to tear your meniscus or ACL?? Pickleball hurts! :) Or - it's a great, convenient play room for little ones. Or a gamers' paradise for the older set. #Choices. We also have two designated offices; one on the first floor & a second in a private wing with its own staircase on the second floor. Three wet bars and a dry bar. Custom cabinetry & built-ins throughout. There's a 20x40 salt water pool. Oversized, tilting European windows & sliders drench the home in natural light. Organic modern; warm & functional. A true walk out lower level that easily doubles as a pool house with a full bath, second laundry and entertaining spaces. A full house generator and even an EV outlet. It's all here. Come visit. Come home

4 Sycamore Dr, Westport

$5,050,000

Carefully crafted Connecticut modern farmhouse by award-winning Heine Development, this exceptional 6-bedroom residence blends timeless architecture with refined contemporary living amongst 4 finished levels on 2 private, level acres in one of Westport's most convenient luxury locations. Designed with perfection in symmetry, detail, and craftsmanship, the home pairs classic farmhouse inspiration with sophisticated modern finishes, including wide-plank white oak floors, curated lighting, and elegant interiors by renowned House of Clement. The stunning chef's kitchen features Sub-Zero and Wolf appliances, seamlessly connecting to beautifully scaled living and entertaining spaces filled with natural light with Southern exposure and beautiful sunsets. Outdoors, enjoy a resort-style ozone maintained 20'x 50'pool with automatic safety cover, sun shelf, and expansive flat lawns enhanced by organic vegetable beds. The extraordinary lower level offers the ultimate lifestyle experience with a gym, sauna, full bath and a custom treehouse, playroom, and second laundry room, creating flexible spaces for wellness, recreation, and everyday convenience. Additional highlights include natural gas heat, a generator, and exceptional indoor-outdoor flow designed for effortless living and entertaining. A rare offering that combines privacy, luxury, and modern farmhouse elegance just moments from town, train, beaches, and all that Westport has to offer.

6 Beds ⋅ 9 Baths ⋅ 24178890 MLS

Carefully crafted Connecticut modern farmhouse by award-winning Heine Development, this exceptional 6-bedroom residence blends timeless architecture with refined contemporary living amongst 4 finished levels on 2 private, level acres in one of Westport's most convenient luxury locations. Designed with perfection in symmetry, detail, and craftsmanship, the home pairs classic farmhouse inspiration with sophisticated modern finishes, including wide-plank white oak floors, curated lighting, and elegant interiors by renowned House of Clement. The stunning chef's kitchen features Sub-Zero and Wolf appliances, seamlessly connecting to beautifully scaled living and entertaining spaces filled with natural light with Southern exposure and beautiful sunsets. Outdoors, enjoy a resort-style ozone maintained 20'x 50'pool with automatic safety cover, sun shelf, and expansive flat lawns enhanced by organic vegetable beds. The extraordinary lower level offers the ultimate lifestyle experience with a gym, sauna, full bath and a custom treehouse, playroom, and second laundry room, creating flexible spaces for wellness, recreation, and everyday convenience. Additional highlights include natural gas heat, a generator, and exceptional indoor-outdoor flow designed for effortless living and entertaining. A rare offering that combines privacy, luxury, and modern farmhouse elegance just moments from town, train, beaches, and all that Westport has to offer.

5 W Branch Rd, Westport

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