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Classic Colonial 5 Bedroom 5 - 1/2 Bath set on over 1 acre with a Gunite Swimming Pool on Westport's longest and perhaps, most sought after Cul-De-Sac! Almost 4700 sq ft on 1st & 2nd floors (hardwood flooring throughout), Plus 1400 sq ft in the fully finished, daylight, walk-out lower level. On the Main level the Gracious Living Room with Fireplace & Box Bay Window, is so large it easily accommodates the grand piano. Stroll through the Cocktail Lounge with built-ins, wet-bar & wine fridge to the delightful sunny, oversized Dining Room with dozens of windows & French Doors that lead to the rear deck. Circle back to the large Eat-In Kitchen with Island that seats four and a dedicated Dining Area by the Bay Window, this all seamlessly flows into the Family Room with Fireplace, Built-In Bookshelves and French Doors opening to the rear deck with views of the pool below. Rounding out the first floor are a Home Office, Ensuite Guest Bedroom with a Full Bath and Walk-In Closet, Half Bath in hall. The 2nd floor has an Enormous Primary Suite with Spa Bath, 3 Walk-In closets & Office or Dressing Room attached to the suite. The 2nd level has 3 more spacious family bedrooms, including one with an ensuite bath and walk-in closet and two more that have ample closet space and share a hall bath. The daylight, walkout lower level has a full bath, tv/media room, gym/playroom with sink, d/w, and fridge and a bonus storage room. Generac Generator! Walls freshly painted! Newer -Roof, HVAC, Septic!

5 Beds ⋅ 6 Baths ⋅ 24213615 MLS

Classic Colonial 5 Bedroom 5 - 1/2 Bath set on over 1 acre with a Gunite Swimming Pool on Westport's longest and perhaps, most sought after Cul-De-Sac! Almost 4700 sq ft on 1st & 2nd floors (hardwood flooring throughout), Plus 1400 sq ft in the fully finished, daylight, walk-out lower level. On the Main level the Gracious Living Room with Fireplace & Box Bay Window, is so large it easily accommodates the grand piano. Stroll through the Cocktail Lounge with built-ins, wet-bar & wine fridge to the delightful sunny, oversized Dining Room with dozens of windows & French Doors that lead to the rear deck. Circle back to the large Eat-In Kitchen with Island that seats four and a dedicated Dining Area by the Bay Window, this all seamlessly flows into the Family Room with Fireplace, Built-In Bookshelves and French Doors opening to the rear deck with views of the pool below. Rounding out the first floor are a Home Office, Ensuite Guest Bedroom with a Full Bath and Walk-In Closet, Half Bath in hall. The 2nd floor has an Enormous Primary Suite with Spa Bath, 3 Walk-In closets & Office or Dressing Room attached to the suite. The 2nd level has 3 more spacious family bedrooms, including one with an ensuite bath and walk-in closet and two more that have ample closet space and share a hall bath. The daylight, walkout lower level has a full bath, tv/media room, gym/playroom with sink, d/w, and fridge and a bonus storage room. Generac Generator! Walls freshly painted! Newer -Roof, HVAC, Septic!

14 High Point Rd, Westport

$4,250,000

Tucked along a tranquil lane, mere steps from the soft sands of Westport's coveted Compo Beach, 19 Roosevelt Road is coastal living at its most refined. This picture-perfect residence of four bedrooms and three and a half baths pairs timeless elegance with effortless comfort. It was reimagined from the studs up in 2019 and is fully FEMA-compliant, with two light-filled levels and every modern convenience. On the main level, a gracious living room sets the tone, framed by custom built-in bookcases and warmed by a gas fireplace. The chef's kitchen is the heart of the home. It has a generous center island, a Sub-Zero refrigerator, a Wolf gas range and a dedicated wine refrigerator. Beyond it, a sun-drenched dining area flows into a step-down family room wrapped in windows, opening directly to the patio for seamless indoor-outdoor living. A private den or home office and an elegant powder room complete the floor. Upstairs are four bedrooms. The serene primary suite has its own balcony overlooking the professionally designed grounds. Three additional bedrooms of generous proportion share two beautifully appointed baths. Outside, lush gardens unfold around two stone patios, an enchanting setting for alfresco dining and summer entertaining. The home also includes a whole-house generator, a security system and irrigation. A new roof (2019), natural gas, city water and sewer complete the picture. An exceptional offering moments from the shore, ready to be enjoyed in every season.

4 Beds ⋅ 4 Baths ⋅ 24213343 MLS

Tucked along a tranquil lane, mere steps from the soft sands of Westport's coveted Compo Beach, 19 Roosevelt Road is coastal living at its most refined. This picture-perfect residence of four bedrooms and three and a half baths pairs timeless elegance with effortless comfort. It was reimagined from the studs up in 2019 and is fully FEMA-compliant, with two light-filled levels and every modern convenience. On the main level, a gracious living room sets the tone, framed by custom built-in bookcases and warmed by a gas fireplace. The chef's kitchen is the heart of the home. It has a generous center island, a Sub-Zero refrigerator, a Wolf gas range and a dedicated wine refrigerator. Beyond it, a sun-drenched dining area flows into a step-down family room wrapped in windows, opening directly to the patio for seamless indoor-outdoor living. A private den or home office and an elegant powder room complete the floor. Upstairs are four bedrooms. The serene primary suite has its own balcony overlooking the professionally designed grounds. Three additional bedrooms of generous proportion share two beautifully appointed baths. Outside, lush gardens unfold around two stone patios, an enchanting setting for alfresco dining and summer entertaining. The home also includes a whole-house generator, a security system and irrigation. A new roof (2019), natural gas, city water and sewer complete the picture. An exceptional offering moments from the shore, ready to be enjoyed in every season.

19 Roosevelt Rd, Westport

$2,000,000

Tucked away at the end of a quiet cul-de-sac in Westport's desirable Charcoal Hill neighborhood, this beautiful one-level ranch offers the perfect blend of comfort, privacy, and easy living. Situated on 2.03 acres bordering a 7-acre land trust preserve, the home provides a peaceful setting with plenty of room to enjoy the outdoors. Thoughtfully updated throughout, the home features 3 bedrooms, 3 full bathrooms, and 2 additional flexible rooms. The bright, open layout includes a beautifully appointed kitchen with Bertazzoni appliances, Marvin windows, Kohler fixtures, and two wood-burning fireplaces. The primary suite opens to a private deck overlooking the property, while a covered deck offers a wonderful space for relaxing or entertaining. The spacious finished walk-out lower level provides additional living space, a full bathroom, and versatile rooms perfect for guests, home offices, or recreation. Additional features include a 2-car garage, high-efficiency HVAC, and smart-home technology. Conveniently located just half a mile from Coleytown schools, with easy access to the Merritt Parkway and downtown Westport. A wonderful opportunity to enjoy comfortable, move-in-ready living in a private and convenient Westport location.

3 Beds ⋅ 3 Baths ⋅ 24213937 MLS

Tucked away at the end of a quiet cul-de-sac in Westport's desirable Charcoal Hill neighborhood, this beautiful one-level ranch offers the perfect blend of comfort, privacy, and easy living. Situated on 2.03 acres bordering a 7-acre land trust preserve, the home provides a peaceful setting with plenty of room to enjoy the outdoors. Thoughtfully updated throughout, the home features 3 bedrooms, 3 full bathrooms, and 2 additional flexible rooms. The bright, open layout includes a beautifully appointed kitchen with Bertazzoni appliances, Marvin windows, Kohler fixtures, and two wood-burning fireplaces. The primary suite opens to a private deck overlooking the property, while a covered deck offers a wonderful space for relaxing or entertaining. The spacious finished walk-out lower level provides additional living space, a full bathroom, and versatile rooms perfect for guests, home offices, or recreation. Additional features include a 2-car garage, high-efficiency HVAC, and smart-home technology. Conveniently located just half a mile from Coleytown schools, with easy access to the Merritt Parkway and downtown Westport. A wonderful opportunity to enjoy comfortable, move-in-ready living in a private and convenient Westport location.

2 Charcoal Ln, Westport

$2,795,000

Lovingly cherished by the same family for over 50 years, this 1965 five bedroom home presents a wonderful opportunity to create something truly special in one of Westport's most desirable neighborhoods. Ideally situated within walking distance to the water and train, the location offers the perfect blend of coastal charm, convenience, and community. Recent updates, including fresh interior paint, refinished or new hardwood flooring, provide a refreshed starting point, while the home's abundant potential invites you to bring your vision to life. Whether you choose to thoughtfully renovate, reimagine, or create your dream home, this is a rare chance to invest in a property with a special history and an exceptional setting on a quiet street near Longshore Club Park. This treasured property is ready for its next chapter, just moments from everything that makes Westport living so special.

5 Beds ⋅ 4 Baths ⋅ 24213304 MLS

Lovingly cherished by the same family for over 50 years, this 1965 five bedroom home presents a wonderful opportunity to create something truly special in one of Westport's most desirable neighborhoods. Ideally situated within walking distance to the water and train, the location offers the perfect blend of coastal charm, convenience, and community. Recent updates, including fresh interior paint, refinished or new hardwood flooring, provide a refreshed starting point, while the home's abundant potential invites you to bring your vision to life. Whether you choose to thoughtfully renovate, reimagine, or create your dream home, this is a rare chance to invest in a property with a special history and an exceptional setting on a quiet street near Longshore Club Park. This treasured property is ready for its next chapter, just moments from everything that makes Westport living so special.

4 Surrey Ln, Westport

$2,950,000

A rare opportunity to own an exceptional woodland estate, where space, serenity, and natural beauty converge. Set beyond a long, gracefully winding driveway, this expansive residence is surrounded by mature trees, creating a remarkable sense of arrival and seclusion. Thoughtfully suited for multigenerational living, the home features a separate wing offering flexibility for extended family, an in-law suite, or long-term guests, allowing for both privacy and connection under one roof. Generous living spaces provide an ideal setting for sophisticated entertaining and relaxed everyday living, while tranquil woodland views create a peaceful backdrop throughout the seasons. Outdoors, a stunning natural gunite pool offers a private, resort-like oasis, beautifully integrated into the wooded landscape and perfect for summer entertaining and relaxation. Combining versatile living arrangements, exceptional space, and a truly serene setting, this distinctive property offers a rare opportunity to experience the best of private estate living. Pre-inspection items have been completed and repaired, providing added peace of mind for the next owner.

5 Beds ⋅ 6 Baths ⋅ 24212624 MLS

A rare opportunity to own an exceptional woodland estate, where space, serenity, and natural beauty converge. Set beyond a long, gracefully winding driveway, this expansive residence is surrounded by mature trees, creating a remarkable sense of arrival and seclusion. Thoughtfully suited for multigenerational living, the home features a separate wing offering flexibility for extended family, an in-law suite, or long-term guests, allowing for both privacy and connection under one roof. Generous living spaces provide an ideal setting for sophisticated entertaining and relaxed everyday living, while tranquil woodland views create a peaceful backdrop throughout the seasons. Outdoors, a stunning natural gunite pool offers a private, resort-like oasis, beautifully integrated into the wooded landscape and perfect for summer entertaining and relaxation. Combining versatile living arrangements, exceptional space, and a truly serene setting, this distinctive property offers a rare opportunity to experience the best of private estate living. Pre-inspection items have been completed and repaired, providing added peace of mind for the next owner.

142 Easton Rd, Westport

$6,975,000

Experience waterfront living at 233 Hillspoint Road, a striking new construction home located directly on Old Mill Beach with panoramic water views. A private elevator is planned to serve all three floors, providing convenient access from the garage to the living areas and up to the private rooftop deck. The planned home combines clean architectural lines with an open floor plan, 9 and 10 foot ceilings and expansive walls of glass that capture natural light and showcase Long Island Sound throughout. The design includes four bedrooms, each with an en-suite bath, highlighted by a spectacular primary suite. The very private rooftop deck offers an exceptional setting for entertaining, enjoying sea breezes and watching sailboats and fireworks over the Sound. The lower level is designed to accommodate a hot tub spa and cold plunge pool, complemented by an outdoor shower. A beach-level covered terrace provides a seamless connection to the beach. A rare opportunity to bring your vision to an extraordinary Westport waterfront setting.

4 Beds ⋅ 5 Baths ⋅ 24212594 MLS

Experience waterfront living at 233 Hillspoint Road, a striking new construction home located directly on Old Mill Beach with panoramic water views. A private elevator is planned to serve all three floors, providing convenient access from the garage to the living areas and up to the private rooftop deck. The planned home combines clean architectural lines with an open floor plan, 9 and 10 foot ceilings and expansive walls of glass that capture natural light and showcase Long Island Sound throughout. The design includes four bedrooms, each with an en-suite bath, highlighted by a spectacular primary suite. The very private rooftop deck offers an exceptional setting for entertaining, enjoying sea breezes and watching sailboats and fireworks over the Sound. The lower level is designed to accommodate a hot tub spa and cold plunge pool, complemented by an outdoor shower. A beach-level covered terrace provides a seamless connection to the beach. A rare opportunity to bring your vision to an extraordinary Westport waterfront setting.

233 Hillspoint Rd, Westport

$3,295,000

Turnkey 2013 Contemporary Oasis | 5 Beds | Pool | Prime Westport Flawless execution meets ultimate convenience at 4 Turkey Hill Lane. Built in 2013 and meticulously maintained, this 5,318sqft. contemporary offers the ultimate turnkey experience in Westport's highly sought-after Long Lots neighborhood. The Interiors: An open-concept, light-filled layout designed for modern living. The centerpiece is a spectacular 2-story great room with a floor-to-ceiling stone fireplace. The seamless flow leads right into a high-end chef's kitchen featuring Sub-Zero appliances, double wall ovens, a wine chiller, and a massive walk-in pantry. Upstairs, the primary suite delivers with dual walk-in closets, a luxe en-suite, and a private balcony. Three additional upper-level bedrooms feature smart Jack-and-Jill setups, while a massive third-floor rec room handles everything from billiards to a home gym. The Grounds: 1.07 level acres of unparalleled outdoor living. Highlights include a heated gunite pool & spa, custom stone patio with pergola, and an outdoor stone fireplace. Beyond the pool, the expansive flat lawn rolls gently down to a private brook. Solar, a 3-car attached garage, and city utilities ensure effortless homeownership. Enjoy privacy without sacrificing convenience-you are just minutes from Westport's downtown dining, high-end retail, beaches, and the Metro-North station. Note: Listing Agent is related to a principal/member of the selling entity.

5 Beds ⋅ 5 Baths ⋅ 24212748 MLS

Turnkey 2013 Contemporary Oasis | 5 Beds | Pool | Prime Westport Flawless execution meets ultimate convenience at 4 Turkey Hill Lane. Built in 2013 and meticulously maintained, this 5,318sqft. contemporary offers the ultimate turnkey experience in Westport's highly sought-after Long Lots neighborhood. The Interiors: An open-concept, light-filled layout designed for modern living. The centerpiece is a spectacular 2-story great room with a floor-to-ceiling stone fireplace. The seamless flow leads right into a high-end chef's kitchen featuring Sub-Zero appliances, double wall ovens, a wine chiller, and a massive walk-in pantry. Upstairs, the primary suite delivers with dual walk-in closets, a luxe en-suite, and a private balcony. Three additional upper-level bedrooms feature smart Jack-and-Jill setups, while a massive third-floor rec room handles everything from billiards to a home gym. The Grounds: 1.07 level acres of unparalleled outdoor living. Highlights include a heated gunite pool & spa, custom stone patio with pergola, and an outdoor stone fireplace. Beyond the pool, the expansive flat lawn rolls gently down to a private brook. Solar, a 3-car attached garage, and city utilities ensure effortless homeownership. Enjoy privacy without sacrificing convenience-you are just minutes from Westport's downtown dining, high-end retail, beaches, and the Metro-North station. Note: Listing Agent is related to a principal/member of the selling entity.

4 Turkey Hill Ln, Westport

$1,199,000

Ideally situated in a highly walkable in-town location, this charming 1928 home offers a rare opportunity to create something truly special in the heart of Westport. Set on a lovely private lot, the property combines classic character with a wonderfully convenient setting close to shops, restaurants, schools, and all that downtown Westport has to offer. Owned and cherished by the same family for approximately 40 years, the home retains the warmth and architectural details that give an older house its distinctive appeal. Oak floors, gracious proportions, and timeless character provide a wonderful foundation for its next chapter. A first-floor in-law/primary bedroom suite, thoughtfully added in the 1960s, offers convenient one-level living and adds flexibility to the original floor plan. Upstairs, two roomy bedrooms share a generously sized bathroom that presents an exciting renovation opportunity: the space could be reconfigured to create two en-suite bathrooms, one for each bedroom, adding modern functionality while preserving the home's charm and character. While the house is in need of renovation, its established setting, private grounds, classic details, and highly desirable in-town location make it an exceptional opportunity for those looking to restore, renovate, and make the home their own. For buyers seeking in-town convenience, privacy, and authentic Westport character, this is a special property with tremendous potential.

3 Beds ⋅ 3 Baths ⋅ 24211260 MLS

Ideally situated in a highly walkable in-town location, this charming 1928 home offers a rare opportunity to create something truly special in the heart of Westport. Set on a lovely private lot, the property combines classic character with a wonderfully convenient setting close to shops, restaurants, schools, and all that downtown Westport has to offer. Owned and cherished by the same family for approximately 40 years, the home retains the warmth and architectural details that give an older house its distinctive appeal. Oak floors, gracious proportions, and timeless character provide a wonderful foundation for its next chapter. A first-floor in-law/primary bedroom suite, thoughtfully added in the 1960s, offers convenient one-level living and adds flexibility to the original floor plan. Upstairs, two roomy bedrooms share a generously sized bathroom that presents an exciting renovation opportunity: the space could be reconfigured to create two en-suite bathrooms, one for each bedroom, adding modern functionality while preserving the home's charm and character. While the house is in need of renovation, its established setting, private grounds, classic details, and highly desirable in-town location make it an exceptional opportunity for those looking to restore, renovate, and make the home their own. For buyers seeking in-town convenience, privacy, and authentic Westport character, this is a special property with tremendous potential.

280 Main St, Westport

$4,299,000

Welcome to BAYBERRY FARMS- a refined oasis of style, comfort and custom amenities begins to unfold upon arrival at this property in an area known for fine estates. A gated drive welcomes you home, first to an ample motor court and then you will pass through carefully landscaped gardens. Inside, the creative and energetic spirit of this home begins to reveal the array of quality features that define it. Sensitively blending the character of a country retreat w/bold modern vision, this 5-BR residence was completely reimagined in 2025. The large living room w/built-ins, bay window & fpl is ideal for grand entertaining. The large sunroom/office is lined w/windows & glass doors. The gourmet kitchen has custom exotic wood cabinetry, Viking appliances & a breakfast area with a folding glass wall that leads to the pool terrace. The DR has a wall of glass, unique corner fpl & original built-ins. The family rm has a modern fpl feature wall & large-scale space for any gathering. Flexible layout w/2nd sunny office. A bonus area over the garage has an incredible game room & gym. The primary ste is an incredible retreat- you will not find another like it. This five-star space has an amazing glass-lined bedroom, two custom walk-in dressing rms w/full glass-fronted built-ins, & a stunning bath w/massive glass shower, soaking tub & more. The rear property rivals boutique hotels w/very large stone terrace, full summer kitchen w/pizza oven, gunite pool w/auto cover, hot tub, porch, garden

5 Beds ⋅ 5 Baths ⋅ 24212297 MLS

Welcome to BAYBERRY FARMS- a refined oasis of style, comfort and custom amenities begins to unfold upon arrival at this property in an area known for fine estates. A gated drive welcomes you home, first to an ample motor court and then you will pass through carefully landscaped gardens. Inside, the creative and energetic spirit of this home begins to reveal the array of quality features that define it. Sensitively blending the character of a country retreat w/bold modern vision, this 5-BR residence was completely reimagined in 2025. The large living room w/built-ins, bay window & fpl is ideal for grand entertaining. The large sunroom/office is lined w/windows & glass doors. The gourmet kitchen has custom exotic wood cabinetry, Viking appliances & a breakfast area with a folding glass wall that leads to the pool terrace. The DR has a wall of glass, unique corner fpl & original built-ins. The family rm has a modern fpl feature wall & large-scale space for any gathering. Flexible layout w/2nd sunny office. A bonus area over the garage has an incredible game room & gym. The primary ste is an incredible retreat- you will not find another like it. This five-star space has an amazing glass-lined bedroom, two custom walk-in dressing rms w/full glass-fronted built-ins, & a stunning bath w/massive glass shower, soaking tub & more. The rear property rivals boutique hotels w/very large stone terrace, full summer kitchen w/pizza oven, gunite pool w/auto cover, hot tub, porch, garden

191 Bayberry Ln, Westport

$5,995,000

Magnificent new construction by AR Luxury Homes on a flat, private acre at the end of a coveted cul-de-sac in Greens Farms. Thoughtfully designed finishes by Tara Benet Design of Greenwich, this 6-bedroom, 6 full/2 half bath residence offers 7,874 sq ft across the first and second floors, plus a finished 1,950+/- sq ft walk-out lower level. Soaring 10' first-floor ceilings anchor an open plan with a great room, custom kitchen, formal dining room, living room, office, wet bar, and mudroom. The primary suite offers a spa bath and walk-in closet, with four additional ensuite bedrooms. The walk-out lower level includes a bedroom, full bath, playroom, gym, and ample storage. Outside, enjoy a 20' x 40' heated pool with spa and automatic cover on a bucolic property. City water, septic, and propane service the home. There is space for an elevator to all floors that can be added, and 1,800 sq ft can be finished on the walk up third floor at additional cost. A rare opportunity, with time to customize select finishes. Home to be completed late spring 2027.

6 Beds ⋅ 9 Baths ⋅ 24199970 MLS

Magnificent new construction by AR Luxury Homes on a flat, private acre at the end of a coveted cul-de-sac in Greens Farms. Thoughtfully designed finishes by Tara Benet Design of Greenwich, this 6-bedroom, 6 full/2 half bath residence offers 7,874 sq ft across the first and second floors, plus a finished 1,950+/- sq ft walk-out lower level. Soaring 10' first-floor ceilings anchor an open plan with a great room, custom kitchen, formal dining room, living room, office, wet bar, and mudroom. The primary suite offers a spa bath and walk-in closet, with four additional ensuite bedrooms. The walk-out lower level includes a bedroom, full bath, playroom, gym, and ample storage. Outside, enjoy a 20' x 40' heated pool with spa and automatic cover on a bucolic property. City water, septic, and propane service the home. There is space for an elevator to all floors that can be added, and 1,800 sq ft can be finished on the walk up third floor at additional cost. A rare opportunity, with time to customize select finishes. Home to be completed late spring 2027.

19 Harding Ln, Westport

$2,895,000

A masterclass in modern coastal architecture, this four-level waterfront retreat delivers a seamless connection to the Saugatuck River. Floor-to-ceiling glass anchors the open-concept main floor, filling it with natural light and showcasing broad river views. Recent high-end infrastructure and tech upgrades make the home as smart as it is stylish--featuring custom Lutron automated window shades throughout, a fully integrated audio/video system, custom window and retractable door screens, and EV charger pre-wiring. Outdoors, enjoy an automatic irrigation system, a conservation-approved custom wire and rail fence, and dock approvals nearing completion, clearing the path to launch your boat into Long Island Sound. An adjacent park further preserves the home's scenic setting and surrounding privacy. Spanning 1,841 intelligently planned square feet, the layout offers ideal space separation and turn-key, lock-and-go convenience: a private second-floor primary suite with walk-in closet and en suite bathroom with tub and steam shower, a third-floor guest suite with a private balcony, and a lower-level family room next to a third bedroom with ensuite bathroom and walk-in closet. Just outside, a water's edge terrace offers effortless riverfront entertaining--all in a prime Westport setting moments from downtown, offering immediate access to local dining, shops and parks.

3 Beds ⋅ 4 Baths ⋅ 24211839 MLS

A masterclass in modern coastal architecture, this four-level waterfront retreat delivers a seamless connection to the Saugatuck River. Floor-to-ceiling glass anchors the open-concept main floor, filling it with natural light and showcasing broad river views. Recent high-end infrastructure and tech upgrades make the home as smart as it is stylish--featuring custom Lutron automated window shades throughout, a fully integrated audio/video system, custom window and retractable door screens, and EV charger pre-wiring. Outdoors, enjoy an automatic irrigation system, a conservation-approved custom wire and rail fence, and dock approvals nearing completion, clearing the path to launch your boat into Long Island Sound. An adjacent park further preserves the home's scenic setting and surrounding privacy. Spanning 1,841 intelligently planned square feet, the layout offers ideal space separation and turn-key, lock-and-go convenience: a private second-floor primary suite with walk-in closet and en suite bathroom with tub and steam shower, a third-floor guest suite with a private balcony, and a lower-level family room next to a third bedroom with ensuite bathroom and walk-in closet. Just outside, a water's edge terrace offers effortless riverfront entertaining--all in a prime Westport setting moments from downtown, offering immediate access to local dining, shops and parks.

79 Riverside Ave, Westport

$2,049,000

Welcome to Saugatuck Shores, where you're not simply purchasing a home, you're embracing a lifestyle. This exceptional beach house offers an inviting floor plan, luxurious modern finishes, custom millwork, incredible water views, and a spacious private backyard. Enjoy your favorite wine al fresco from the charming screened-in front porch, expansive rear deck, or your private balcony off the primary suite. Step inside to a spacious living room anchored by a beautiful stone fireplace, an elegant formal dining room, and a stunning kitchen featuring custom white cabinetry, professional-grade stainless steel appliances, a large center island, and Carrara marble countertops. Coffered ceilings and custom millwork add character throughout the main level, which is completed by a beautiful full bath with an elegant glass-enclosed shower. Upstairs, the impressive primary suite boasts panoramic water views, a luxurious en-suite bath, walk-in closet, and access to its own private balcony. Two additional generously sized bedrooms feature beautiful wood beams that add warmth and distinctive character, while a full hallway bath is finished with marble tile and a tub/shower combination. Perfectly positioned to enjoy everything this sought-after waterfront community has to offer, while remaining just minutes from exceptional restaurants, shopping, nightlife, major highways, and the train. A rare opportunity to enjoy coastal living in one of Saugatuck's most desirable settings.

3 Beds ⋅ 3 Baths ⋅ 24212313 MLS

Welcome to Saugatuck Shores, where you're not simply purchasing a home, you're embracing a lifestyle. This exceptional beach house offers an inviting floor plan, luxurious modern finishes, custom millwork, incredible water views, and a spacious private backyard. Enjoy your favorite wine al fresco from the charming screened-in front porch, expansive rear deck, or your private balcony off the primary suite. Step inside to a spacious living room anchored by a beautiful stone fireplace, an elegant formal dining room, and a stunning kitchen featuring custom white cabinetry, professional-grade stainless steel appliances, a large center island, and Carrara marble countertops. Coffered ceilings and custom millwork add character throughout the main level, which is completed by a beautiful full bath with an elegant glass-enclosed shower. Upstairs, the impressive primary suite boasts panoramic water views, a luxurious en-suite bath, walk-in closet, and access to its own private balcony. Two additional generously sized bedrooms feature beautiful wood beams that add warmth and distinctive character, while a full hallway bath is finished with marble tile and a tub/shower combination. Perfectly positioned to enjoy everything this sought-after waterfront community has to offer, while remaining just minutes from exceptional restaurants, shopping, nightlife, major highways, and the train. A rare opportunity to enjoy coastal living in one of Saugatuck's most desirable settings.

7 Marsh Rd, Westport

$2,500,000

Tucked away on 1.25 serene acres in Westport's sought-after Coleytown neighborhood, this timeless 5-bedroom Georgian Colonial seamlessly blends grand architectural elegance with comfortable everyday living. Welcomed by an inviting, large front porch this impressive home offers exceptional space both inside and out. Inside, the grand main level flows effortlessly between a large formal living room, a gracious formal dining room, and a designated home office. At the heart of the home, a spacious, sunny kitchen connects directly to a casual den/TV room, while double doors lead from both the kitchen and dining room onto a lovely patio ideal for outdoor dining and entertaining. One of the home's most show-stopping features is the massive bonus room,expertly crafted from real barn wood and complete with exposed timber beams, wide plank wood floors, and a dedicated fireplace, perfect for cozy evenings or hosting large gatherings. Throughout the main house, you will find a total of 3 fireplaces creating a warm, inviting atmosphere. Upstairs, the expansive primary suite serves as a peaceful retreat featuring a massive walk-in closet and a remarkably large primary bathroom. A second spacious bedroom functions as its own suite, featuring a private bathroom and an exclusive balcony overlooking the grounds. The resort-style backyard oasis centers around an inground pool and a fun, fully equipped pool house featuring a private bathroom and its own fireplace for chilly evening gathering.

5 Beds ⋅ 5 Baths ⋅ 24212307 MLS

Tucked away on 1.25 serene acres in Westport's sought-after Coleytown neighborhood, this timeless 5-bedroom Georgian Colonial seamlessly blends grand architectural elegance with comfortable everyday living. Welcomed by an inviting, large front porch this impressive home offers exceptional space both inside and out. Inside, the grand main level flows effortlessly between a large formal living room, a gracious formal dining room, and a designated home office. At the heart of the home, a spacious, sunny kitchen connects directly to a casual den/TV room, while double doors lead from both the kitchen and dining room onto a lovely patio ideal for outdoor dining and entertaining. One of the home's most show-stopping features is the massive bonus room,expertly crafted from real barn wood and complete with exposed timber beams, wide plank wood floors, and a dedicated fireplace, perfect for cozy evenings or hosting large gatherings. Throughout the main house, you will find a total of 3 fireplaces creating a warm, inviting atmosphere. Upstairs, the expansive primary suite serves as a peaceful retreat featuring a massive walk-in closet and a remarkably large primary bathroom. A second spacious bedroom functions as its own suite, featuring a private bathroom and an exclusive balcony overlooking the grounds. The resort-style backyard oasis centers around an inground pool and a fun, fully equipped pool house featuring a private bathroom and its own fireplace for chilly evening gathering.

23 Punch Bowl Dr, Westport

$1,990,000

Tucked away in Westport's coveted Greens Farms neighborhood, this beautifully updated home is set on over 2 acres and offers the perfect balance of comfort, flexibility, and modern living. Beloved by its owners for many years, it has been the setting for countless family gatherings, celebrations, and cherished memories and is now ready for its next chapter. The renovated kitchen features an induction cooktop, abundant pantry space, and a bright eat-in area with sliders to a newly built deck, creating an effortless connection to the beautifully landscaped backyard. The adjoining family room, with its soaring cathedral ceiling and inviting fireplace, is the perfect place to gather. The spacious primary suite offers a renovated ensuite bath, while four additional bedrooms, including one ideal for a home office, provide ample space for family and guests. A renovated hall bath features a double vanity. A private wing with its own full kitchen and separate entrance provides flexibility for an in-law or au pair suite. The walk-out lower level adds a bedroom, full bath, and generous storage for guests, recreation, or extended living. Major improvements include the roof, replacement windows and doors, exterior repainting, high-efficiency furnace, hot water heater, and oil tank. Lovingly cared for and thoughtfully updated, this special home offers space, privacy, and versatility. Just minutes from schools, beaches, train, shopping, and all that Westport has to offer

7 Beds ⋅ 5 Baths ⋅ 24197538 MLS

Tucked away in Westport's coveted Greens Farms neighborhood, this beautifully updated home is set on over 2 acres and offers the perfect balance of comfort, flexibility, and modern living. Beloved by its owners for many years, it has been the setting for countless family gatherings, celebrations, and cherished memories and is now ready for its next chapter. The renovated kitchen features an induction cooktop, abundant pantry space, and a bright eat-in area with sliders to a newly built deck, creating an effortless connection to the beautifully landscaped backyard. The adjoining family room, with its soaring cathedral ceiling and inviting fireplace, is the perfect place to gather. The spacious primary suite offers a renovated ensuite bath, while four additional bedrooms, including one ideal for a home office, provide ample space for family and guests. A renovated hall bath features a double vanity. A private wing with its own full kitchen and separate entrance provides flexibility for an in-law or au pair suite. The walk-out lower level adds a bedroom, full bath, and generous storage for guests, recreation, or extended living. Major improvements include the roof, replacement windows and doors, exterior repainting, high-efficiency furnace, hot water heater, and oil tank. Lovingly cared for and thoughtfully updated, this special home offers space, privacy, and versatility. Just minutes from schools, beaches, train, shopping, and all that Westport has to offer

11 Turkey Hill Cir, Westport

$4,050,000

Privately set in Westport's coveted Old Hill neighborhood, this like-new sophisticated residence designed by famed architect Peter Wormser pairs striking architecture with timeless, understated elegance. Soaring ceilings, beautifully curated spaces and abundant natural light define the stylish interiors, creating a home that is at once impressive and inviting. 4 finished levels provide exceptional space for everyday living, entertaining, work and guests. The primary suite stuns with its 20-foot ceilings, fireplace, 2 walk-in closets and spa bath. 4 additional bedrooms each feature walk-in closets, while 2 private offices offer dedicated work-from-home space. A 3rd-floor recreation room with full bath adds more flexibility, while the beautifully finished lower level has a home theater, gym, space for play, plus storage. Outdoors, the magical setting unfolds through multiple entertaining spaces, from inviting covered porches to an expansive stone patio with a fully-equipped outdoor kitchen, built-in grill and Big Green Egg, offering an exceptional backdrop for gatherings large and small. Lush, established landscaping creates a remarkable sense of privacy, yet the home is just over a mile to Westport's vibrant downtown. Whole-house generator, solar and level 2 EV charger! The NYC-bound train is just 9 minutes away. Distinctive, sophisticated and effortlessly livable, this exceptional Old Hill residence is a rare offering of inspired architecture, privacy and a prime location.

5 Beds ⋅ 6 Baths ⋅ 24211806 MLS

Privately set in Westport's coveted Old Hill neighborhood, this like-new sophisticated residence designed by famed architect Peter Wormser pairs striking architecture with timeless, understated elegance. Soaring ceilings, beautifully curated spaces and abundant natural light define the stylish interiors, creating a home that is at once impressive and inviting. 4 finished levels provide exceptional space for everyday living, entertaining, work and guests. The primary suite stuns with its 20-foot ceilings, fireplace, 2 walk-in closets and spa bath. 4 additional bedrooms each feature walk-in closets, while 2 private offices offer dedicated work-from-home space. A 3rd-floor recreation room with full bath adds more flexibility, while the beautifully finished lower level has a home theater, gym, space for play, plus storage. Outdoors, the magical setting unfolds through multiple entertaining spaces, from inviting covered porches to an expansive stone patio with a fully-equipped outdoor kitchen, built-in grill and Big Green Egg, offering an exceptional backdrop for gatherings large and small. Lush, established landscaping creates a remarkable sense of privacy, yet the home is just over a mile to Westport's vibrant downtown. Whole-house generator, solar and level 2 EV charger! The NYC-bound train is just 9 minutes away. Distinctive, sophisticated and effortlessly livable, this exceptional Old Hill residence is a rare offering of inspired architecture, privacy and a prime location.

11 Woodside Ln, Westport

$1,699,000

Set on a stunning, meticulously manicured, lush, one-acre property in the heart of Greens Farms and approx. 1 mile to the beach. This inviting 4 bedroom, 3.5 bath home is a jewel box with endless potential to personalize, expand and create your ideal retreat or simply enjoy it's current curated beauty. The property's expansive grounds, mature landscaping and beautiful garden create a peaceful backdrop for everyday living. Conveniently located in the heart of Westport, just minutes from beaches, train, shopping, dining, schools, and everyday amenities. 4 Lookout Lane offers an exceptional opportunity to enjoy the beauty, convenience, and a coastal community lifestyle that that is the essence of Westport. **Please see addendum for a full list of upgrades, including new roof in 2021, new oil tank 2025, newer windows and furnace and full house generator among multiple other improvements.**

4 Beds ⋅ 4 Baths ⋅ 24204801 MLS

Set on a stunning, meticulously manicured, lush, one-acre property in the heart of Greens Farms and approx. 1 mile to the beach. This inviting 4 bedroom, 3.5 bath home is a jewel box with endless potential to personalize, expand and create your ideal retreat or simply enjoy it's current curated beauty. The property's expansive grounds, mature landscaping and beautiful garden create a peaceful backdrop for everyday living. Conveniently located in the heart of Westport, just minutes from beaches, train, shopping, dining, schools, and everyday amenities. 4 Lookout Lane offers an exceptional opportunity to enjoy the beauty, convenience, and a coastal community lifestyle that that is the essence of Westport. **Please see addendum for a full list of upgrades, including new roof in 2021, new oil tank 2025, newer windows and furnace and full house generator among multiple other improvements.**

4 Lookout Ln, Westport

$1,999,999

TO BE SOLD AS-IS AND ONLY WITH #29 BRIDGE STREET together for $1,999,999....Rare opportunity to own two parcels including a 2 br cottage on the rear lot and a 6br 2-family on the front lot for investment, owner-occupant, renovation, or potential subdivision possibilities. Buyer to do own due dilligience.

2 Beds ⋅ 2 Baths ⋅ 24209600 MLS

TO BE SOLD AS-IS AND ONLY WITH #29 BRIDGE STREET together for $1,999,999....Rare opportunity to own two parcels including a 2 br cottage on the rear lot and a 6br 2-family on the front lot for investment, owner-occupant, renovation, or potential subdivision possibilities. Buyer to do own due dilligience.

33 Bridge St, Westport

$6,595,000

Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning four levels, this six-bedroom home features an airy layout with refined finishes throughout. The open-concept kitchen flows seamlessly into the main living spaces, highlighted by a statement fireplace. A glass-enclosed office offers privacy, while additional living and dining areas, a stylish scullery, and an oversized mudroom add everyday functionality. A dramatic pivot door opens to a gallery-style entry. Upstairs, the primary suite is a serene retreat with its own fireplace, dual walk-in closets, a dressing area, and a spa-like bath. Four en-suite bedrooms and a laundry room complete the second floor, while the top level offers a private sixth suite, office, and flexible open spaces. The walk-out lower level expands the home with walls of glass, a terrace, gym, bar, wine cellar, media/playroom, and additional office. Outside, a 16'x32' pool, multiple terraces, and a grilling area create effortless summer living, complemented by a three-car garage with EV charging. (Agent is owner)

6 Beds ⋅ 9 Baths ⋅ 24211630 MLS

Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning four levels, this six-bedroom home features an airy layout with refined finishes throughout. The open-concept kitchen flows seamlessly into the main living spaces, highlighted by a statement fireplace. A glass-enclosed office offers privacy, while additional living and dining areas, a stylish scullery, and an oversized mudroom add everyday functionality. A dramatic pivot door opens to a gallery-style entry. Upstairs, the primary suite is a serene retreat with its own fireplace, dual walk-in closets, a dressing area, and a spa-like bath. Four en-suite bedrooms and a laundry room complete the second floor, while the top level offers a private sixth suite, office, and flexible open spaces. The walk-out lower level expands the home with walls of glass, a terrace, gym, bar, wine cellar, media/playroom, and additional office. Outside, a 16'x32' pool, multiple terraces, and a grilling area create effortless summer living, complemented by a three-car garage with EV charging. (Agent is owner)

8 Loretta Ct, Westport

$2,050,000

HIGHEST & BEST OFFERS REQUESTED BY NOON TUESDAY 10/13, THANK YOU! Distinctive Dream Home in Coveted Westport, CT! Colorful gardens and a circular drive welcome you to a home with its own personality on an established cul-de-sac lane. Within walking distance of neighborhood eateries and award-winning schools and minutes of all that Westport has to offer, enjoy primetime living year-round. Double glass entry doors open to a gracious Foyer and impressive Great Room with a dramatic stone fireplace, vaulted ceiling, original beams and captivating garden views that surround the living and dining spaces. The culinary hub in the renovated Kitchen features white granite counters, an oversized stainless refrigerator and freezer, and an enviable spice pantry. The sunny Breakfast Area and Family Room flow to the Office, Screened Porch, and Deck. The private Primary Suite with a renovated bath and double walk-in closets completes the main level. Upstairs are four Guest Bedrooms and two full baths, including access to the front balcony and a partially finished walk-up attic.

5 Beds ⋅ 5 Baths ⋅ 24208459 MLS

HIGHEST & BEST OFFERS REQUESTED BY NOON TUESDAY 10/13, THANK YOU! Distinctive Dream Home in Coveted Westport, CT! Colorful gardens and a circular drive welcome you to a home with its own personality on an established cul-de-sac lane. Within walking distance of neighborhood eateries and award-winning schools and minutes of all that Westport has to offer, enjoy primetime living year-round. Double glass entry doors open to a gracious Foyer and impressive Great Room with a dramatic stone fireplace, vaulted ceiling, original beams and captivating garden views that surround the living and dining spaces. The culinary hub in the renovated Kitchen features white granite counters, an oversized stainless refrigerator and freezer, and an enviable spice pantry. The sunny Breakfast Area and Family Room flow to the Office, Screened Porch, and Deck. The private Primary Suite with a renovated bath and double walk-in closets completes the main level. Upstairs are four Guest Bedrooms and two full baths, including access to the front balcony and a partially finished walk-up attic.

1 Melon Patch Ln, Westport

$3,695,000

Exceptional new construction, 9 Berkeley Road presents a sophisticated interpretation of modern Westport living, blending timeless architecture with beautifully considered spaces and an exceptional floor plan. Gracious proportions, abundant natural light and 9-foot ceilings create an immediate sense of understated luxury throughout the main level. At the heart of the home, an expansive chef's kitchen with separate scullery and breakfast area opens seamlessly to a stunning family room accented by oak ceiling beams. Formal living and dining rooms provide elegant settings for entertaining, while a private home office offers a quiet retreat. A beautifully designed first-floor guest suite with full bath and walk-in closet provides privacy and flexibility for family and guests. Expansive doors extend the living spaces outdoors to a generous rear deck, complemented by a bluestone-covered porch for effortless indoor-outdoor entertaining. Upstairs, the luxurious primary suite is a private sanctuary featuring a spacious bedroom, dressing area, walk-in closet and beautifully proportioned bath. Three additional bedrooms, multiple baths, generous closets, a dedicated laundry room and loft complete the second level. Sophisticated yet inviting, and an exceptional opportunity to own a thoughtfully designed new residence where elevated style, modern luxury and effortless livability come together in one of Westport's most desirable settings. *REPRESENTAIVE IMAGES* Agent/owner

5 Beds ⋅ 5 Baths ⋅ 24209539 MLS

Exceptional new construction, 9 Berkeley Road presents a sophisticated interpretation of modern Westport living, blending timeless architecture with beautifully considered spaces and an exceptional floor plan. Gracious proportions, abundant natural light and 9-foot ceilings create an immediate sense of understated luxury throughout the main level. At the heart of the home, an expansive chef's kitchen with separate scullery and breakfast area opens seamlessly to a stunning family room accented by oak ceiling beams. Formal living and dining rooms provide elegant settings for entertaining, while a private home office offers a quiet retreat. A beautifully designed first-floor guest suite with full bath and walk-in closet provides privacy and flexibility for family and guests. Expansive doors extend the living spaces outdoors to a generous rear deck, complemented by a bluestone-covered porch for effortless indoor-outdoor entertaining. Upstairs, the luxurious primary suite is a private sanctuary featuring a spacious bedroom, dressing area, walk-in closet and beautifully proportioned bath. Three additional bedrooms, multiple baths, generous closets, a dedicated laundry room and loft complete the second level. Sophisticated yet inviting, and an exceptional opportunity to own a thoughtfully designed new residence where elevated style, modern luxury and effortless livability come together in one of Westport's most desirable settings. *REPRESENTAIVE IMAGES* Agent/owner

9 Berkeley Rd, Westport

$7,399,000

With views over rooftops and to the Long Island Sound, this extraordinary new residence brings a new level of luxury to Westport's coveted Compo Beach area. Inspired by its coastal setting, the design from esteemed architect Bruce Beinfield layers organic materials, warm woods and stone with exquisite bespoke details and best-in-class finishes. Soaring 10-foot ceilings, walls of glass, limewash walls and abundant natural light create an ethereal feel. Imported Poggenpohl and Shinoki cabinetry and a showstopping kitchen with luminous Cristallo countertops reflect the uncompromising quality. A 1st floor lounge opens to the pool and spa, while an oversized outdoor kitchen and cantilevered covered patio create a dramatic setting for entertaining. The primary suite is a private sanctuary with 15-ft ceiling, gas fireplace, spectacular spa bath and dual custom-fitted closets. A generous 3rd-floor guest retreat has a lounge, roof deck and Sound views. The finished lower level offers an oversized gym, steam shower bath, bar with 100-inch TV and walk-out to the pool. Control4 Smart Home tech operates HVAC, security, cameras, lighting, blinds, music, pool, irrigation. Room for an elevator. Oversized garage has room for car lift. The private, fenced property is enveloped in lush professional landscaping. Walk to Compo Beach, Longshore and NYC train, an extraordinary expression of modern coastal luxury and serenity in a premier Fairfield County location.

6 Beds ⋅ 7 Baths ⋅ 24205429 MLS

With views over rooftops and to the Long Island Sound, this extraordinary new residence brings a new level of luxury to Westport's coveted Compo Beach area. Inspired by its coastal setting, the design from esteemed architect Bruce Beinfield layers organic materials, warm woods and stone with exquisite bespoke details and best-in-class finishes. Soaring 10-foot ceilings, walls of glass, limewash walls and abundant natural light create an ethereal feel. Imported Poggenpohl and Shinoki cabinetry and a showstopping kitchen with luminous Cristallo countertops reflect the uncompromising quality. A 1st floor lounge opens to the pool and spa, while an oversized outdoor kitchen and cantilevered covered patio create a dramatic setting for entertaining. The primary suite is a private sanctuary with 15-ft ceiling, gas fireplace, spectacular spa bath and dual custom-fitted closets. A generous 3rd-floor guest retreat has a lounge, roof deck and Sound views. The finished lower level offers an oversized gym, steam shower bath, bar with 100-inch TV and walk-out to the pool. Control4 Smart Home tech operates HVAC, security, cameras, lighting, blinds, music, pool, irrigation. Room for an elevator. Oversized garage has room for car lift. The private, fenced property is enveloped in lush professional landscaping. Walk to Compo Beach, Longshore and NYC train, an extraordinary expression of modern coastal luxury and serenity in a premier Fairfield County location.

8 Tar Rock Rd, Westport

$1,399,000

Don't let the square footage fool you - this home lives large. Tucked into a lovely, walkable neighborhood perfect for evening strolls and bike rides, this is a home that punches well above its size, with all the essentials thoughtfully in place. The main level sets the tone, LR w/high ceilings opens to the kitchen for an open flow that feels bright and spacious. Just a short flight up, three bedrooms share their own private level. Downstairs, a large family room with a fireplace anchors the lower level, alongside a fourth bedroom that flexes easily as a home office. The basement adds laundry and abundant storage, with plenty of untapped potential to finish. Outside, a cozy screened-in porch is made for lazy summer evenings and movie nights. And there's room to grow: expand above the oversized two-car garage for a primary suite retreat, or enclose the porch to create a formal dining room - the footprint here has real potential to stretch further. Best of all, the hard work is already done. Fresh exterior paint, a new roof, and many recent updates mean this home is truly move-in ready. With 5mins to train and I95, 6mins to Compo beach, 5mins to downtown Main St. this location is hard to beat. agent is owner

4 Beds ⋅ 2 Baths ⋅ 24206112 MLS

Don't let the square footage fool you - this home lives large. Tucked into a lovely, walkable neighborhood perfect for evening strolls and bike rides, this is a home that punches well above its size, with all the essentials thoughtfully in place. The main level sets the tone, LR w/high ceilings opens to the kitchen for an open flow that feels bright and spacious. Just a short flight up, three bedrooms share their own private level. Downstairs, a large family room with a fireplace anchors the lower level, alongside a fourth bedroom that flexes easily as a home office. The basement adds laundry and abundant storage, with plenty of untapped potential to finish. Outside, a cozy screened-in porch is made for lazy summer evenings and movie nights. And there's room to grow: expand above the oversized two-car garage for a primary suite retreat, or enclose the porch to create a formal dining room - the footprint here has real potential to stretch further. Best of all, the hard work is already done. Fresh exterior paint, a new roof, and many recent updates mean this home is truly move-in ready. With 5mins to train and I95, 6mins to Compo beach, 5mins to downtown Main St. this location is hard to beat. agent is owner

38 Guyer Rd, Westport

$2,885,000

Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four additional bedrooms are ample in scale - one en-suite, with a Jack-and-Jill bath connecting two others - while a full bath and a dedicated office complete the first level. Outdoors, an expansive terrace invites al fresco dining and entertaining above a manicured, secluded yard set on a coveted corner lot. Beyond the door: sunrise strolls to the water, sunsets over the boardwalk, Longshore Club, downtown shops, dining, and the library, plus a straightforward Manhattan commute via Saugatuck Metro-North. Homes in this enclave seldom surface.

5 Beds ⋅ 4 Baths ⋅ 24209324 MLS

Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four additional bedrooms are ample in scale - one en-suite, with a Jack-and-Jill bath connecting two others - while a full bath and a dedicated office complete the first level. Outdoors, an expansive terrace invites al fresco dining and entertaining above a manicured, secluded yard set on a coveted corner lot. Beyond the door: sunrise strolls to the water, sunsets over the boardwalk, Longshore Club, downtown shops, dining, and the library, plus a straightforward Manhattan commute via Saugatuck Metro-North. Homes in this enclave seldom surface.

4 Bradley St, Westport

$1,800,000

Storybook charm meets comfortable living in this enchanting 3 bedroom, 4 bath home. Located at the end of a quiet block you will find exposed beams, character-rich details, and a warm, inviting atmosphere create a home that feels truly special. Thoughtfully designed spaces blend timeless charm with everyday functionality, offering room to gather, relax, and entertain. A spacious deck extends the living space outdoors, perfect for morning coffee, al fresco dining, or enjoying the surrounding setting. Each bedroom provides its own sense of retreat, while four full baths add exceptional convenience. From its distinctive architectural details to its cozy, welcoming feel, this is a home with personality and a true sense of place. Convenient central location close to trains and the beach.

3 Beds ⋅ 4 Baths ⋅ 24206830 MLS

Storybook charm meets comfortable living in this enchanting 3 bedroom, 4 bath home. Located at the end of a quiet block you will find exposed beams, character-rich details, and a warm, inviting atmosphere create a home that feels truly special. Thoughtfully designed spaces blend timeless charm with everyday functionality, offering room to gather, relax, and entertain. A spacious deck extends the living space outdoors, perfect for morning coffee, al fresco dining, or enjoying the surrounding setting. Each bedroom provides its own sense of retreat, while four full baths add exceptional convenience. From its distinctive architectural details to its cozy, welcoming feel, this is a home with personality and a true sense of place. Convenient central location close to trains and the beach.

27 Rayfield Rd, Westport

$7,250,000

The home offers timeless and classic New England, the charm you have been seeking. Set up on a quiet hill in the heart of Green Farms, this picturesque shingle home checks every box! In 2021, the home underwent a major renovation, with every room updated and all mechanicals and cedar roof replaced. Sited on nearly two acres of manicured property, there are extensive stone walls, multiple patio areas, mature plantings, and distant Long Island Sound views. The flexible floor plan offers 5 bedrooms on the 2nd floor, plus additional bedroom spaces on the 3rd floor and lower walkout level. A new detached outbuilding, currently used as a gym, offers exceptional flexibility as a private guest suite, home office, or dedicated space for a trading team. The home features a wrap-around porch, gunite pool, outdoor kitchen, fire pit, dog grooming station in the garage, guest suite, theatre, gym, and whole-house audio system. Refined design, exceptional quality, and thoughtful details throughout.

5 Beds ⋅ 9 Baths ⋅ 24206974 MLS

The home offers timeless and classic New England, the charm you have been seeking. Set up on a quiet hill in the heart of Green Farms, this picturesque shingle home checks every box! In 2021, the home underwent a major renovation, with every room updated and all mechanicals and cedar roof replaced. Sited on nearly two acres of manicured property, there are extensive stone walls, multiple patio areas, mature plantings, and distant Long Island Sound views. The flexible floor plan offers 5 bedrooms on the 2nd floor, plus additional bedroom spaces on the 3rd floor and lower walkout level. A new detached outbuilding, currently used as a gym, offers exceptional flexibility as a private guest suite, home office, or dedicated space for a trading team. The home features a wrap-around porch, gunite pool, outdoor kitchen, fire pit, dog grooming station in the garage, guest suite, theatre, gym, and whole-house audio system. Refined design, exceptional quality, and thoughtful details throughout.

20 Turkey Hill Cir, Westport

$7,200,000

Exceptional coastal living in Westport's coveted Compo Beach neighborhood. Built in 2024, 51 Compo Beach Road is a stunning four-bedroom home with spectacular Long Island Sound views, a private heated pool, and an extraordinary rooftop deck-moments from Compo Beach. Designed to embrace its setting, this striking residence is filled with natural light and captivating water views. Expansive windows frame the ever-changing coastal scenery, with beautiful sunrises over Long Island Sound and spectacular sunsets. The bright, open interior is sophisticated yet relaxed, with clean architectural lines and effortless flow for living and entertaining. Four bedrooms and four full baths offer space for family and guests, and an elevator connects all levels. Main living floors were built to FEMA-compliant standards, important for newer coastal construction. Outside, the private heated pool is a true summer retreat-a rare amenity this close to the beach. The rooftop deck is a showstopper, with panoramic water views for sunrise coffee, sunset cocktails, entertaining, and evenings under the stars. Plus smart-home technology, a two-car garage and a whole-house generator. Moments from Compo Beach, the marina and Longshore Club Park, with downtown Westport, restaurants, shopping and Metro-North to NYC within easy reach. A rare opportunity for newer construction, a private pool, extraordinary water views and sunrise-to-sunset vistas in one of Westport's most iconic coastal neighborhoods.

4 Beds ⋅ 4 Baths ⋅ 24204128 MLS

Exceptional coastal living in Westport's coveted Compo Beach neighborhood. Built in 2024, 51 Compo Beach Road is a stunning four-bedroom home with spectacular Long Island Sound views, a private heated pool, and an extraordinary rooftop deck-moments from Compo Beach. Designed to embrace its setting, this striking residence is filled with natural light and captivating water views. Expansive windows frame the ever-changing coastal scenery, with beautiful sunrises over Long Island Sound and spectacular sunsets. The bright, open interior is sophisticated yet relaxed, with clean architectural lines and effortless flow for living and entertaining. Four bedrooms and four full baths offer space for family and guests, and an elevator connects all levels. Main living floors were built to FEMA-compliant standards, important for newer coastal construction. Outside, the private heated pool is a true summer retreat-a rare amenity this close to the beach. The rooftop deck is a showstopper, with panoramic water views for sunrise coffee, sunset cocktails, entertaining, and evenings under the stars. Plus smart-home technology, a two-car garage and a whole-house generator. Moments from Compo Beach, the marina and Longshore Club Park, with downtown Westport, restaurants, shopping and Metro-North to NYC within easy reach. A rare opportunity for newer construction, a private pool, extraordinary water views and sunrise-to-sunset vistas in one of Westport's most iconic coastal neighborhoods.

51 Compo Beach Rd, Westport

$3,400,000

In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. The main level flows beautifully and showcases dramatic interiors with large gathering spaces, gourmet kitchen facilities and incredible entertaining capabilities. The main floor primary suite serves as a luxurious private retreat with his and her bathrooms and separate sitting room/office. Upstairs, three additional bedrooms continue the home's commitment to comfort and privacy. The finished lower level extends the home's appeal with numerous recreational spaces and a full bath. Beyond the impressive interiors, the grounds are truly breathtaking. A rhythm of blooming flowers and mature landscaping creates a sense of beauty throughout all four seasons, thoughtfully designed to offer year-round color and serenity. Located on a private cul-de-sac, this home is a true compound-balanced, gracious, and masterfully executed, offering unparalleled living inside and out. Once you have arrived, it will be hard to leave!

6 Beds ⋅ 7 Baths ⋅ 24208426 MLS

In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. The main level flows beautifully and showcases dramatic interiors with large gathering spaces, gourmet kitchen facilities and incredible entertaining capabilities. The main floor primary suite serves as a luxurious private retreat with his and her bathrooms and separate sitting room/office. Upstairs, three additional bedrooms continue the home's commitment to comfort and privacy. The finished lower level extends the home's appeal with numerous recreational spaces and a full bath. Beyond the impressive interiors, the grounds are truly breathtaking. A rhythm of blooming flowers and mature landscaping creates a sense of beauty throughout all four seasons, thoughtfully designed to offer year-round color and serenity. Located on a private cul-de-sac, this home is a true compound-balanced, gracious, and masterfully executed, offering unparalleled living inside and out. Once you have arrived, it will be hard to leave!

9 N Ridge Rd, Westport

$7,489,000

UPDATED SURVEY. Set on one acre of waterfront property, One Driftwood Point holds views from every room of the Long Island Sound and Saugatuck Harbor on three sides and a perfect overlook of the backyard tennis court to complete this property as of one of the most unique and stunning spots in Westport! Stretched out into the harbor, the modern contemporary style home is designed to feel immersed in the sparkle of water and sea breeze from each deck, every room, and all levels of open living space. The layout opens with a double height entry and leads upstairs to the massive living spaces that maximize the gorgeous light and waterfront surroundings - with a front to back living room set with multiple conversation areas and easy deck flow, the space is mirrored with a matching family room holding a lounge area, billiard room and 3 fireplaces in the house. An office and half bath finish off the top floor. On the main level, the dining room & kitchen enjoy the view of boats in the harbor. The primary bedroom suite with 2 bathrooms, and a walk-in closet/dressing room steps out to the main level deck overlooking the front yard & water beyond. The 2 main level bedrooms share a full bath. The professionally landscaped property is surrounded by plantings, includes beach, tennis court & potential dock for boating! Driftwood Point lives like a full retreat, while it's actually moments from Saugatuck dining, shopping & train station conveniences and all Westport amenities.

3 Beds ⋅ 4 Baths ⋅ 24208381 MLS

UPDATED SURVEY. Set on one acre of waterfront property, One Driftwood Point holds views from every room of the Long Island Sound and Saugatuck Harbor on three sides and a perfect overlook of the backyard tennis court to complete this property as of one of the most unique and stunning spots in Westport! Stretched out into the harbor, the modern contemporary style home is designed to feel immersed in the sparkle of water and sea breeze from each deck, every room, and all levels of open living space. The layout opens with a double height entry and leads upstairs to the massive living spaces that maximize the gorgeous light and waterfront surroundings - with a front to back living room set with multiple conversation areas and easy deck flow, the space is mirrored with a matching family room holding a lounge area, billiard room and 3 fireplaces in the house. An office and half bath finish off the top floor. On the main level, the dining room & kitchen enjoy the view of boats in the harbor. The primary bedroom suite with 2 bathrooms, and a walk-in closet/dressing room steps out to the main level deck overlooking the front yard & water beyond. The 2 main level bedrooms share a full bath. The professionally landscaped property is surrounded by plantings, includes beach, tennis court & potential dock for boating! Driftwood Point lives like a full retreat, while it's actually moments from Saugatuck dining, shopping & train station conveniences and all Westport amenities.

1 Driftwood Point Rd, Westport

$10,985,000

100% FEMA compliant & storm friendly AND 100% completed, this special new construction Bluewater Home is priced to SELL. Located steps from Compo Beach on prestigious Owenoke Park, a 6050 sqft true coastal gem which checks every box and delivers the ultimate Westport lifestyle with pool and spa, Gray's Creek waterfront access, Long Island Sound views, and a rare 3+ car garage. 5 ensuite bedrooms, custom kitchen with double-islands and scullery, elevator, primary suite sauna, multiple balconies and decks, large lower-level indoor/outdoor loggia area built for entertaining and PLENTY of PARKING for everyone!! Truly beach living at its finest.

5 Beds ⋅ 7 Baths ⋅ 24207610 MLS

100% FEMA compliant & storm friendly AND 100% completed, this special new construction Bluewater Home is priced to SELL. Located steps from Compo Beach on prestigious Owenoke Park, a 6050 sqft true coastal gem which checks every box and delivers the ultimate Westport lifestyle with pool and spa, Gray's Creek waterfront access, Long Island Sound views, and a rare 3+ car garage. 5 ensuite bedrooms, custom kitchen with double-islands and scullery, elevator, primary suite sauna, multiple balconies and decks, large lower-level indoor/outdoor loggia area built for entertaining and PLENTY of PARKING for everyone!! Truly beach living at its finest.

14 Owenoke Park, Westport

$1,399,000

Set on over two private acres at the end of a peaceful cul-de-sac in Westport, this traditional center-hall Colonial with four bedrooms and 2.5 baths offers a wonderful combination of privacy, space and potential. A circular driveway framed by stone walls, Belgian block and exterior lighting creates a welcoming arrival. Inside, hardwood floors run throughout the main living spaces, including a spacious living room and dining room, while the family room is anchored by a classic brick fireplace and opens to a standout screened porch with a vaulted wood ceiling, exposed beams and skylights. This inviting porch is the perfect place for seasonal dining, relaxing and entertaining while overlooking the expansive backyard and mature landscape. Upstairs, the primary bedroom features an en-suite bath, walk-in closet and additional closet. Hardwood floors are found beneath the carpeting upstairs. With plenty of opportunity to update and personalize, this well-loved home is ready for its next chapter. It's a special place to create your own vision while enjoying all that Westport has to offer on lovely Primrose Lane.

4 Beds ⋅ 3 Baths ⋅ 24200486 MLS

Set on over two private acres at the end of a peaceful cul-de-sac in Westport, this traditional center-hall Colonial with four bedrooms and 2.5 baths offers a wonderful combination of privacy, space and potential. A circular driveway framed by stone walls, Belgian block and exterior lighting creates a welcoming arrival. Inside, hardwood floors run throughout the main living spaces, including a spacious living room and dining room, while the family room is anchored by a classic brick fireplace and opens to a standout screened porch with a vaulted wood ceiling, exposed beams and skylights. This inviting porch is the perfect place for seasonal dining, relaxing and entertaining while overlooking the expansive backyard and mature landscape. Upstairs, the primary bedroom features an en-suite bath, walk-in closet and additional closet. Hardwood floors are found beneath the carpeting upstairs. With plenty of opportunity to update and personalize, this well-loved home is ready for its next chapter. It's a special place to create your own vision while enjoying all that Westport has to offer on lovely Primrose Lane.

9 Primrose Ln, Westport