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Welcome to this beautifully maintained 1945 stone-front Cape in the heart of Old Hill. Loved by the same family for 22 years, it radiates warmth and character. With 5 bedrooms, 5.5 baths, and two flexible spaces for home offices, it offers comfort and versatility, including a first-floor suite ideal for guests or in-laws. The light-filled kitchen flows into an inviting dining area and cozy sunken family room with a stunning river-rock fireplace-perfect for gatherings or quiet evenings. French doors open to a level backyard with a bluestone terrace, outdoor fireplace, and grilling area, creating an ideal setting for entertaining. A 3-car tandem heated garage, mudroom, pantry, and laundry room add practicality, while a gracious dining room and front-to-back living room with built-ins and a second fireplace set the stage for special occasions. Upstairs, the serene primary suite offers a balcony, spa-inspired bath, and dressing room. Three additional bedroom, 2 additional full baths and a loft provide space for everyone. The finished lower level features a playroom, gym area, full bath, and ample storage with walk-out access to the Garage . Move-in ready with room to personalize, this special home invites you to start your next chapter in one of Westport's most desirable neighborhoods. Don't miss the chance to make it yours!

5 Beds ⋅ 6 Baths ⋅ 24115085 MLS

Welcome to this beautifully maintained 1945 stone-front Cape in the heart of Old Hill. Loved by the same family for 22 years, it radiates warmth and character. With 5 bedrooms, 5.5 baths, and two flexible spaces for home offices, it offers comfort and versatility, including a first-floor suite ideal for guests or in-laws. The light-filled kitchen flows into an inviting dining area and cozy sunken family room with a stunning river-rock fireplace-perfect for gatherings or quiet evenings. French doors open to a level backyard with a bluestone terrace, outdoor fireplace, and grilling area, creating an ideal setting for entertaining. A 3-car tandem heated garage, mudroom, pantry, and laundry room add practicality, while a gracious dining room and front-to-back living room with built-ins and a second fireplace set the stage for special occasions. Upstairs, the serene primary suite offers a balcony, spa-inspired bath, and dressing room. Three additional bedroom, 2 additional full baths and a loft provide space for everyone. The finished lower level features a playroom, gym area, full bath, and ample storage with walk-out access to the Garage . Move-in ready with room to personalize, this special home invites you to start your next chapter in one of Westport's most desirable neighborhoods. Don't miss the chance to make it yours!

20 Old Hill Rd, Westport

$2,780,000

Nestled in Westport's coveted Old Hill neighborhood, this stunning residence blends classic Colonial design w/modern amenities. You're greeted by the centerpiece of the home - an impressive foyer w/soaring ceilings. The spacious office w/lacquer-finished built-ins includes a fireplace and access to the veranda. For more intimate gatherings, go through the French doors to a sitting room, w/pocket-door to the wet bar. Or head to the main open-floor plan for the kitchen, dining, and living rooms. The chef's kitchen boasts an expansive Marble and Farrow & Ball island, Miele dishwashers, ovens, and warming drawer, Thermador fridge, Viking range, large walk-in pantry, and bay window seating. Easily sit ten in the dining area. From the living room, access the veranda, complete w/grill, built-in speakers, and ceiling fans. Plenty of room to play in the beautiful fenced in yard, w/curated plantings in bloom Apr-Oct. Upstairs, the massive primary suite includes a wood-burning fireplace, terrace, ensuite bath w/heated floors and two walk-in closets. The walk-ins include special surprises and numerous built-ins. 3 other large beds, 2 full baths, and laundry room complete this floor. Ascend to the upper level, w/large finished room, huge 5th bed, & full bath w/walk-in closets. Features: 9ft ceilings, 3-car garage, numerous smart-home features, Lutron lighting, irrigation system, custom millwork, whole-house generator, wetlands-free 1.07 acres. Extraordinary, meticulous, move-in ready.

5 Beds ⋅ 5 Baths ⋅ 24098607 MLS

Nestled in Westport's coveted Old Hill neighborhood, this stunning residence blends classic Colonial design w/modern amenities. You're greeted by the centerpiece of the home - an impressive foyer w/soaring ceilings. The spacious office w/lacquer-finished built-ins includes a fireplace and access to the veranda. For more intimate gatherings, go through the French doors to a sitting room, w/pocket-door to the wet bar. Or head to the main open-floor plan for the kitchen, dining, and living rooms. The chef's kitchen boasts an expansive Marble and Farrow & Ball island, Miele dishwashers, ovens, and warming drawer, Thermador fridge, Viking range, large walk-in pantry, and bay window seating. Easily sit ten in the dining area. From the living room, access the veranda, complete w/grill, built-in speakers, and ceiling fans. Plenty of room to play in the beautiful fenced in yard, w/curated plantings in bloom Apr-Oct. Upstairs, the massive primary suite includes a wood-burning fireplace, terrace, ensuite bath w/heated floors and two walk-in closets. The walk-ins include special surprises and numerous built-ins. 3 other large beds, 2 full baths, and laundry room complete this floor. Ascend to the upper level, w/large finished room, huge 5th bed, & full bath w/walk-in closets. Features: 9ft ceilings, 3-car garage, numerous smart-home features, Lutron lighting, irrigation system, custom millwork, whole-house generator, wetlands-free 1.07 acres. Extraordinary, meticulous, move-in ready.

20 Crawford Rd, Westport

$2,750,000

Located on a quiet cul-de-sac in the heart of Westport, this beautiful timeless Colonial is located at the top of one of the town's most picturesque streets, directly across from the scenic Saugatuck River. The gourmet kitchen features island seating, custom cabinetry, a serving peninsula, and a breakfast room with an abundance of natural light. The front-to-back living room with fireplace and high ceilings is adjacent to the kitchen and is also the heart of the home. Two recently renovated (Trex) decks off the kitchen and living room, along with an expansive terrace, overlook the private backyard-perfect for entertaining and outdoor enjoyment. All bedrooms are located on the second level along with two fully renovated baths. The lower level includes a family room, home gym, full bathroom and a lot of storage. The lower level has potential for a fifth bedroom. Offering 3,674 sq ft of finished living space, 23 Harborview Rd provides both comfort and flexibility, with additional unfinished space to expand within the existing footprint, if desired. Additional highlights include natural gas, public water and sewer, central air, two-car garage with room for storage, and new blue stone front walk. Commuters will appreciate the south of the Post Rd location, just 1.8 miles to the Westport Station. Harborview offers a walkable lifestyle-minutes to town 'over the foot bridge' to the library, Farmer's market, Levitt Pavillion, and restaurants. Audio/Visual

4 Beds ⋅ 4 Baths ⋅ 24163587 MLS

Located on a quiet cul-de-sac in the heart of Westport, this beautiful timeless Colonial is located at the top of one of the town's most picturesque streets, directly across from the scenic Saugatuck River. The gourmet kitchen features island seating, custom cabinetry, a serving peninsula, and a breakfast room with an abundance of natural light. The front-to-back living room with fireplace and high ceilings is adjacent to the kitchen and is also the heart of the home. Two recently renovated (Trex) decks off the kitchen and living room, along with an expansive terrace, overlook the private backyard-perfect for entertaining and outdoor enjoyment. All bedrooms are located on the second level along with two fully renovated baths. The lower level includes a family room, home gym, full bathroom and a lot of storage. The lower level has potential for a fifth bedroom. Offering 3,674 sq ft of finished living space, 23 Harborview Rd provides both comfort and flexibility, with additional unfinished space to expand within the existing footprint, if desired. Additional highlights include natural gas, public water and sewer, central air, two-car garage with room for storage, and new blue stone front walk. Commuters will appreciate the south of the Post Rd location, just 1.8 miles to the Westport Station. Harborview offers a walkable lifestyle-minutes to town 'over the foot bridge' to the library, Farmer's market, Levitt Pavillion, and restaurants. Audio/Visual

23 Harborview Rd, Westport

$2,725,000

A rare Westport retreat blending serenity, sophistication & resort-style living. Privately set at the end of a quiet cul-de-sac off Bayberry Lane, this elegant four-bedroom, three-and-a-half-bath home offers over 4,600 sq ft of sun-filled living space surrounded by beautifully landscaped grounds. The property's two private acres feel like a personal park-complete with mature trees, curated plantings & a koi pond with exotic blooms that showcase the home's four-season appeal. At its heart is an updated gunite pool with electric cover, stone patio & gated backyard designed for both entertaining & everyday enjoyment. The open layout flows from the two-story foyer to the vaulted great room with gas fireplace & French doors to the expansive deck overlooking the pool & gardens. The bright, stone-floored kitchen features high-end appliances, beverage drawers & a wine chiller, connecting seamlessly to the dining, family & breakfast areas. Two home offices-one with vaulted ceilings & another with a private porch-make work-from-home effortless. The serene primary suite includes dual walk-in closets, a custom built-in dressing area, private laundry, a full fitness room & a spa-inspired bath. A separate first-floor guest suite with a new full bath & private entrance offers additional living space ideal for guests, in-laws or an au pair-beyond the home's four bedrooms. The finished lower level provides added versatility with a wine room, recreation area & abundant storage.

4 Beds ⋅ 4 Baths ⋅ 24133128 MLS

A rare Westport retreat blending serenity, sophistication & resort-style living. Privately set at the end of a quiet cul-de-sac off Bayberry Lane, this elegant four-bedroom, three-and-a-half-bath home offers over 4,600 sq ft of sun-filled living space surrounded by beautifully landscaped grounds. The property's two private acres feel like a personal park-complete with mature trees, curated plantings & a koi pond with exotic blooms that showcase the home's four-season appeal. At its heart is an updated gunite pool with electric cover, stone patio & gated backyard designed for both entertaining & everyday enjoyment. The open layout flows from the two-story foyer to the vaulted great room with gas fireplace & French doors to the expansive deck overlooking the pool & gardens. The bright, stone-floored kitchen features high-end appliances, beverage drawers & a wine chiller, connecting seamlessly to the dining, family & breakfast areas. Two home offices-one with vaulted ceilings & another with a private porch-make work-from-home effortless. The serene primary suite includes dual walk-in closets, a custom built-in dressing area, private laundry, a full fitness room & a spa-inspired bath. A separate first-floor guest suite with a new full bath & private entrance offers additional living space ideal for guests, in-laws or an au pair-beyond the home's four bedrooms. The finished lower level provides added versatility with a wine room, recreation area & abundant storage.

6 Nutcracker Ln, Westport

$2,700,000

Set on a quiet, private cul-de-sac very close to town and Winslow Park, this custom five-bedroom Colonial offers an exceptional opportunity for a new owner to leave their mark and add significant value. Designed with best-in-class materials and a thoughtfully planned layout, the home retains its gracious scale, natural flow, and exceptional character. Deferred maintenance has created the chance to elevate a well-loved property and return it to the signature splendor that defined it. The main level features a gourmet kitchen with Sub Zero & Viking appliances, stone counters, custom cabinetry and an adjacent breakfast room leading to a large family room, living room with fireplace, formal dining room, and two private offices with built-ins. French doors from most main floor rooms open to a balcony overlooking a heated Gunite pool and a large, level play area. The walkout lower level has a wall of French doors and is an exquisite poolside space that includes a fully-equipped wet bar, rec/game rm, gym and a full guest suite. Upstairs, the spacious bedroom layout provides comfort and flexibility for a variety of needs. Set on 1.16 +/- acres moments from shopping and recreation, the home is being offered as-is. ***Listing photos include a mix of current 2026 images and select photos from 2009 to illustrate the full potential of the property. Please note that showings are welcomed and booked by appointment, and no open houses are planned.***

5 Beds ⋅ 6 Baths ⋅ 24159517 MLS

Set on a quiet, private cul-de-sac very close to town and Winslow Park, this custom five-bedroom Colonial offers an exceptional opportunity for a new owner to leave their mark and add significant value. Designed with best-in-class materials and a thoughtfully planned layout, the home retains its gracious scale, natural flow, and exceptional character. Deferred maintenance has created the chance to elevate a well-loved property and return it to the signature splendor that defined it. The main level features a gourmet kitchen with Sub Zero & Viking appliances, stone counters, custom cabinetry and an adjacent breakfast room leading to a large family room, living room with fireplace, formal dining room, and two private offices with built-ins. French doors from most main floor rooms open to a balcony overlooking a heated Gunite pool and a large, level play area. The walkout lower level has a wall of French doors and is an exquisite poolside space that includes a fully-equipped wet bar, rec/game rm, gym and a full guest suite. Upstairs, the spacious bedroom layout provides comfort and flexibility for a variety of needs. Set on 1.16 +/- acres moments from shopping and recreation, the home is being offered as-is. ***Listing photos include a mix of current 2026 images and select photos from 2009 to illustrate the full potential of the property. Please note that showings are welcomed and booked by appointment, and no open houses are planned.***

2 Ledgemoor Ln, Westport

$2,700,000

Welcome to Brookside, the amazing new project by GreenDay and Co. Get ready to be captivated by this home's transformation-a breathtaking fusion of classic European charm and modern luxury that will leave you speechless. This isn't just your typical modern farmhouse; it's a beautiful reimagining of a European-style estate, carefully rebuilt from the ground up to inspire and impress. it's a magnificent reimagining of a European-style residence, meticulously rebuilt from the ground up! Step inside this breathtaking five-bedroom masterpiece, where an oversized kitchen paired with a spacious pantry awaits to inspire culinary adventures and unforgettable gatherings! The primary bedroom features a luxurious en suite, and the additional junior suite enhances the already perfectly designed layout. Nestled in an idyllic downtown Westport location on a picturesque cul-de-sac, you'll fall in love with the tranquil ambiance, complemented by the soothing sounds of the delightful mandarin brook bordering the property. Picture yourself savoring your morning coffee on the walk-out deck, effortlessly accessible from both the dining room and kitchen. Everything here is brand new, thoughtfully designed, and ready for the next lucky owners to create beautiful memories. With chic modern finishes, elegant white oak hardwood floors, and a charming front covered porch, this home

5 Beds ⋅ 5 Baths ⋅ 24093563 MLS

Welcome to Brookside, the amazing new project by GreenDay and Co. Get ready to be captivated by this home's transformation-a breathtaking fusion of classic European charm and modern luxury that will leave you speechless. This isn't just your typical modern farmhouse; it's a beautiful reimagining of a European-style estate, carefully rebuilt from the ground up to inspire and impress. it's a magnificent reimagining of a European-style residence, meticulously rebuilt from the ground up! Step inside this breathtaking five-bedroom masterpiece, where an oversized kitchen paired with a spacious pantry awaits to inspire culinary adventures and unforgettable gatherings! The primary bedroom features a luxurious en suite, and the additional junior suite enhances the already perfectly designed layout. Nestled in an idyllic downtown Westport location on a picturesque cul-de-sac, you'll fall in love with the tranquil ambiance, complemented by the soothing sounds of the delightful mandarin brook bordering the property. Picture yourself savoring your morning coffee on the walk-out deck, effortlessly accessible from both the dining room and kitchen. Everything here is brand new, thoughtfully designed, and ready for the next lucky owners to create beautiful memories. With chic modern finishes, elegant white oak hardwood floors, and a charming front covered porch, this home

26 Hitchcock Rd, Westport

$2,700,000

Set on more than two acres of exquisite, park-like property in the coveted Red Coat estate section of Westport, this spectacular modern home with a glorious gunite pool offers an ideal lifestyle. A designer's own residence, this home showcases uncompromising quality with intuitive features. The landscaped approach begins with a large stone parking court that accommodates entertaining on a grand scale. The dramatic entrance leads to a soaring foyer with custom stairs, where the sun-filled interiors begin to unfold and glimpses of the glorious rear property and pool come into view. The grand-scale Great Room w/gas fireplace has windows & doors on three sides, brining in light and views. The fam rm has a professional media system to bring your favorite shows and games to the big screen, and access to the serene screened-in porch. The gourmet kitchen has style and flair w/concrete center island, stone counters, Sub Zero & Viking appls, wet bar w/beverage chiller, lrg pantry, built-in desk, dining area & access to the deck. The dining room has a custom built-in server, 3D ceiling design & doors to a covered deck. The flexible 2nd level has 5 BRs incl a grand primary suite w/two balconies, excellent closet space & a luxe bth w/glass shower & spa tub. All baths have been updated. The apt/guest wing w/priv entry, 2 rms, kitchenette & laundry is ideal for multi-generational living or anyone seeking privacy. Finished walk-out LL w/rec & office spaces. Many new improvements. Generator.

5 Beds ⋅ 6 Baths ⋅ 24132128 MLS

Set on more than two acres of exquisite, park-like property in the coveted Red Coat estate section of Westport, this spectacular modern home with a glorious gunite pool offers an ideal lifestyle. A designer's own residence, this home showcases uncompromising quality with intuitive features. The landscaped approach begins with a large stone parking court that accommodates entertaining on a grand scale. The dramatic entrance leads to a soaring foyer with custom stairs, where the sun-filled interiors begin to unfold and glimpses of the glorious rear property and pool come into view. The grand-scale Great Room w/gas fireplace has windows & doors on three sides, brining in light and views. The fam rm has a professional media system to bring your favorite shows and games to the big screen, and access to the serene screened-in porch. The gourmet kitchen has style and flair w/concrete center island, stone counters, Sub Zero & Viking appls, wet bar w/beverage chiller, lrg pantry, built-in desk, dining area & access to the deck. The dining room has a custom built-in server, 3D ceiling design & doors to a covered deck. The flexible 2nd level has 5 BRs incl a grand primary suite w/two balconies, excellent closet space & a luxe bth w/glass shower & spa tub. All baths have been updated. The apt/guest wing w/priv entry, 2 rms, kitchenette & laundry is ideal for multi-generational living or anyone seeking privacy. Finished walk-out LL w/rec & office spaces. Many new improvements. Generator.

40 Hermit Ln, Westport

$2,650,000

One of Westport's premiere CUL-DE-SACS, WALKING DISTANCE TO ALL 3 SCHOOLS (Long Lots, Bedford, Staples), and 2.3 MILES TO GREENS FARMS TRAIN STATION, this beautifully renovated (2016/2017) 5-bedroom, 4.5-bath home perfectly blends modern luxury with timeless charm. Set on a full acre of manicured grounds, this property offers a serene retreat just minutes from every essential. The open floor plan is designed for effortless entertaining, centered around a gourmet eat-in kitchen with high-end appliances. The main level hosts three bedrooms and 2.5 baths, while the upper level serves as a private sanctuary-a lavish primary suite featuring two expansive walk-in closets, a spa-inspired bath, and a cozy lounge. The light-filled, walk-out lower level is exceptionally versatile, offering a 5th bedroom/gym, full bath, rec room, mudroom, and a dedicated home office with three separate entrances-ideal for remote work. Outside, your personal oasis awaits: a sprawling deck overlooks an inviting in-ground pool/spa, surrounded by lush greenery and a yard perfect for recreation. Unbeatable location complete with natural gas, public water, and easy access to vibrant shopping and dining. This isn't just a home-it's a lifestyle.

5 Beds ⋅ 5 Baths ⋅ 24164819 MLS

One of Westport's premiere CUL-DE-SACS, WALKING DISTANCE TO ALL 3 SCHOOLS (Long Lots, Bedford, Staples), and 2.3 MILES TO GREENS FARMS TRAIN STATION, this beautifully renovated (2016/2017) 5-bedroom, 4.5-bath home perfectly blends modern luxury with timeless charm. Set on a full acre of manicured grounds, this property offers a serene retreat just minutes from every essential. The open floor plan is designed for effortless entertaining, centered around a gourmet eat-in kitchen with high-end appliances. The main level hosts three bedrooms and 2.5 baths, while the upper level serves as a private sanctuary-a lavish primary suite featuring two expansive walk-in closets, a spa-inspired bath, and a cozy lounge. The light-filled, walk-out lower level is exceptionally versatile, offering a 5th bedroom/gym, full bath, rec room, mudroom, and a dedicated home office with three separate entrances-ideal for remote work. Outside, your personal oasis awaits: a sprawling deck overlooks an inviting in-ground pool/spa, surrounded by lush greenery and a yard perfect for recreation. Unbeatable location complete with natural gas, public water, and easy access to vibrant shopping and dining. This isn't just a home-it's a lifestyle.

1 Angora Rd, Westport

$2,650,000

Sparkling river views from four floors of the most modern, chic spaces. With three bedrooms, three and a half baths, gorgeous natural light and the smartest use of 1800 sqft this waterfront home by Vita Design Group has been crafted to truly enjoy its surroundings - a perfect blend of slow tides and vibrant downtown. The main level enjoys a full wall of windows spanning the kitchen, dining area and living room. Upstairs, the primary suite fills the second floor with a serene bedroom, beautiful bath, walk in wardrobe and convenient laundry. A third floor bedroom and bath also offer a bird's eye balcony to take in the sun and sounds of rowers gliding by during the day or live Levitt tunes on a summer evening. A full lower level includes both a den/office and an en-suite bedroom. Sit riverside on the patio or cruise the river straight to the Long Island Sound.

3 Beds ⋅ 4 Baths ⋅ 24147214 MLS

Sparkling river views from four floors of the most modern, chic spaces. With three bedrooms, three and a half baths, gorgeous natural light and the smartest use of 1800 sqft this waterfront home by Vita Design Group has been crafted to truly enjoy its surroundings - a perfect blend of slow tides and vibrant downtown. The main level enjoys a full wall of windows spanning the kitchen, dining area and living room. Upstairs, the primary suite fills the second floor with a serene bedroom, beautiful bath, walk in wardrobe and convenient laundry. A third floor bedroom and bath also offer a bird's eye balcony to take in the sun and sounds of rowers gliding by during the day or live Levitt tunes on a summer evening. A full lower level includes both a den/office and an en-suite bedroom. Sit riverside on the patio or cruise the river straight to the Long Island Sound.

79 Riverside Ave, Westport

$2,645,000

Nestled in the heart of Westport's coveted Old Hill neighborhood, this home offers the charm of an English cottage and a thoughtful design that blends classic character with the modern desire for open, connected living. Encompassing nearly 4,000 square feet, it features four ensuite bedrooms, walk-in closets, and a curated layout that combines timeless architectural details with contemporary comfort. At its center, a sunlit great room anchors the home, seamlessly connecting the custom kitchen, dining area, and living room-ideal for casual family living. While the open-concept design fosters connection, the home also offers refined spaces for formal entertaining. A versatile third-floor retreat provides a spacious bedroom or office that opens to a generous outdoor deck-perfect for morning coffee, remote work, or unwinding under the stars. Meticulous millwork, bespoke cabinetry, and finely crafted finishes are paired with a clean, modern aesthetic, creating a home both rooted in tradition and refreshingly current. Outside, an expansive bluestone patio invites alfresco dining and relaxed gatherings. Mature evergreen trees and fragrant plantings surround the property offering exceptional privacy. Just a short stroll to downtown Westport's restaurants, shopping, library, and the Levitt Pavilion, this home offers historic charm, modern ease, and in-town living.

4 Beds ⋅ 5 Baths ⋅ 24136796 MLS

Nestled in the heart of Westport's coveted Old Hill neighborhood, this home offers the charm of an English cottage and a thoughtful design that blends classic character with the modern desire for open, connected living. Encompassing nearly 4,000 square feet, it features four ensuite bedrooms, walk-in closets, and a curated layout that combines timeless architectural details with contemporary comfort. At its center, a sunlit great room anchors the home, seamlessly connecting the custom kitchen, dining area, and living room-ideal for casual family living. While the open-concept design fosters connection, the home also offers refined spaces for formal entertaining. A versatile third-floor retreat provides a spacious bedroom or office that opens to a generous outdoor deck-perfect for morning coffee, remote work, or unwinding under the stars. Meticulous millwork, bespoke cabinetry, and finely crafted finishes are paired with a clean, modern aesthetic, creating a home both rooted in tradition and refreshingly current. Outside, an expansive bluestone patio invites alfresco dining and relaxed gatherings. Mature evergreen trees and fragrant plantings surround the property offering exceptional privacy. Just a short stroll to downtown Westport's restaurants, shopping, library, and the Levitt Pavilion, this home offers historic charm, modern ease, and in-town living.

11 Old Hill Rd, Westport

$2,630,000

Exceptional new build just completed by SIR Development, Westport's premier builder w/ 30+ yrs experience & 300+ homes. Leave the city for the burbs but keep the conveniences. Just a short walk to Starbucks, Stiles Market, Aux Delice, Little Barn & Big Y Plaza. Short ride to great schools, train & beach. This award winning layout and design has 5 BDRMs and is beautifully detailed across 4 finished levels with top SIR SIGNATURE HOME finishes - Custom Eat-in Kitchen with sleek white cabinetry, oak accents, quartz countertops & backsplash, stainless steel appliances opens to spacious Family Rm w/ fireplace and sliding glass drs lead to granite patio w/ level fenced backyard w/room for pool. 1st flr study with custom built-ins, generous formal DR, mudroom & powder rm. Spacious Master BR Suite has spa bath and 2 Walk-in Closets. Fin 3rd Flr w/5th BR and full bath. Fin walk-out LL has custom built-ins, gym, media room, bonus room & full bath. Terrific layout, style, property & neighborhood. City water, sewer & propane gas. Move-in ready with beautiful landscaping & fence to ensure privacy, perfectly sized to appreciate suburban life. Taxes TBD. Builder's 1 year warranty included.

5 Beds ⋅ 6 Baths ⋅ 24147552 MLS

Exceptional new build just completed by SIR Development, Westport's premier builder w/ 30+ yrs experience & 300+ homes. Leave the city for the burbs but keep the conveniences. Just a short walk to Starbucks, Stiles Market, Aux Delice, Little Barn & Big Y Plaza. Short ride to great schools, train & beach. This award winning layout and design has 5 BDRMs and is beautifully detailed across 4 finished levels with top SIR SIGNATURE HOME finishes - Custom Eat-in Kitchen with sleek white cabinetry, oak accents, quartz countertops & backsplash, stainless steel appliances opens to spacious Family Rm w/ fireplace and sliding glass drs lead to granite patio w/ level fenced backyard w/room for pool. 1st flr study with custom built-ins, generous formal DR, mudroom & powder rm. Spacious Master BR Suite has spa bath and 2 Walk-in Closets. Fin 3rd Flr w/5th BR and full bath. Fin walk-out LL has custom built-ins, gym, media room, bonus room & full bath. Terrific layout, style, property & neighborhood. City water, sewer & propane gas. Move-in ready with beautiful landscaping & fence to ensure privacy, perfectly sized to appreciate suburban life. Taxes TBD. Builder's 1 year warranty included.

10 Wakenor Rd, Westport

$2,625,000

Discover this stunning 6-bedroom single-family home-a modern masterpiece designed for today's lifestyle. Perched on a private cul-de-sac just minutes from downtown Westport, dog parks, beaches, award-winning restaurants, and even a 24-hour CVS for those late-night essentials, this residence perfectly blends convenience with serenity. Step inside and experience Westport luxury redefined-a striking contemporary design surrounded by lush, landscaped grounds that create a peaceful, retreat-like setting. Once home to a celebrated local artist, the interiors exude creativity and sophistication, featuring clean lines, light-filled spaces, and flexible living areas ideal for entertaining or everyday living. Enjoy sweeping natural views, a rooftop deck made for sunsets, and versatile spaces suited for an in-law suite, au pair, or private studio. With a separate-entry studio for creative or professional use, this home adapts to your lifestyle-whether you're a growing family seeking space or a downsizer who refuses to compromise on style.Whether you're hosting family on the fabulous rooftop deck, enjoying the privacy, or welcoming guests to their own separate suite, this home delivers the perfect balance of connection and calm. Note: Town records do not include the heated/cooled first-floor office studio and lower-level art studio in the official square footage. Combined with the finished basement, these areas bring the total living space to approximately 7,734 sq ft.

6 Beds ⋅ 8 Baths ⋅ 24121310 MLS

Discover this stunning 6-bedroom single-family home-a modern masterpiece designed for today's lifestyle. Perched on a private cul-de-sac just minutes from downtown Westport, dog parks, beaches, award-winning restaurants, and even a 24-hour CVS for those late-night essentials, this residence perfectly blends convenience with serenity. Step inside and experience Westport luxury redefined-a striking contemporary design surrounded by lush, landscaped grounds that create a peaceful, retreat-like setting. Once home to a celebrated local artist, the interiors exude creativity and sophistication, featuring clean lines, light-filled spaces, and flexible living areas ideal for entertaining or everyday living. Enjoy sweeping natural views, a rooftop deck made for sunsets, and versatile spaces suited for an in-law suite, au pair, or private studio. With a separate-entry studio for creative or professional use, this home adapts to your lifestyle-whether you're a growing family seeking space or a downsizer who refuses to compromise on style.Whether you're hosting family on the fabulous rooftop deck, enjoying the privacy, or welcoming guests to their own separate suite, this home delivers the perfect balance of connection and calm. Note: Town records do not include the heated/cooled first-floor office studio and lower-level art studio in the official square footage. Combined with the finished basement, these areas bring the total living space to approximately 7,734 sq ft.

19a Darbrook Rd, Westport

$2,620,000

Steeped in history yet thoughtfully reimagined for modern living, this expanded and recently updated antique home offers the rare combination of timeless character, exceptional functionality, and a coveted location just an easy stroll to downtown Westport. Designed for both everyday living and easy entertaining, the home features warm gathering spaces and private retreats. A chef's kitchen with Thermador range and walk-in pantry opens to the home's inviting living and dining areas. Over $600K of recent updates including the stunning, newly-redesigned primary suite - a true sanctuary, with a new focal wall with custom cabinetry and gas fireplace, a well-equipped bath with dual sinks, tub and shower, plus a distinctive turreted sitting room, an idyllic space to relax. Multiple home office options. A new outbuilding elevates the property to an entirely new level. Designed as a private wellness retreat, this extraordinary Onsen-inspired space features hot and cold plunge pools, a sauna, shower, gas fireplace, and loft, creating a resort-quality experience. Outside, the sunny, level property features a new, walled-garden, crushed-stone patio and a 2nd patio, allowing for entertaining, gardening, and enjoying the peaceful surroundings. Room for pool! Town water/gas/sewer. Rich in character, beautifully updated, and uniquely equipped for modern wellness and work-from-home living, this exceptional residence offers a lifestyle rarely found in this historic, near-town neighborhood.

4 Beds ⋅ 5 Baths ⋅ 24185246 MLS

Steeped in history yet thoughtfully reimagined for modern living, this expanded and recently updated antique home offers the rare combination of timeless character, exceptional functionality, and a coveted location just an easy stroll to downtown Westport. Designed for both everyday living and easy entertaining, the home features warm gathering spaces and private retreats. A chef's kitchen with Thermador range and walk-in pantry opens to the home's inviting living and dining areas. Over $600K of recent updates including the stunning, newly-redesigned primary suite - a true sanctuary, with a new focal wall with custom cabinetry and gas fireplace, a well-equipped bath with dual sinks, tub and shower, plus a distinctive turreted sitting room, an idyllic space to relax. Multiple home office options. A new outbuilding elevates the property to an entirely new level. Designed as a private wellness retreat, this extraordinary Onsen-inspired space features hot and cold plunge pools, a sauna, shower, gas fireplace, and loft, creating a resort-quality experience. Outside, the sunny, level property features a new, walled-garden, crushed-stone patio and a 2nd patio, allowing for entertaining, gardening, and enjoying the peaceful surroundings. Room for pool! Town water/gas/sewer. Rich in character, beautifully updated, and uniquely equipped for modern wellness and work-from-home living, this exceptional residence offers a lifestyle rarely found in this historic, near-town neighborhood.

34 Woodside Ave, Westport

$2,600,108

Tucked away at the end of a private lane, this Nantucket-style Colonial sits on 1.21 level acres with city water, offering privacy, flexibility, and space rarely found in Westport. Rebuilt in 2006 on an existing foundation, the property combines classic shingle-style architecture with thoughtful modern living. The main residence features 5 bedrooms, 4.5 baths, and a dedicated home office. The chef's kitchen with professional appliances opens to a spacious deck overlooking the expansive backyard-ideal for entertaining or everyday living. Multiple gathering spaces include a dramatic skylit den/playroom with vaulted ceilings, perfect for a gym, media room, playroom, or recreation space. A standout feature is the full accessory apartment with 2 bedrooms, kitchenette, full bath, and its own garage, offering excellent flexibility for extended family, guests, au pair, or potential rental income. Set on flat, usable land at the end of a quiet private lane, the property provides a peaceful setting while remaining convenient to Westport amenities, schools, and commuting routes. A rare opportunity to own a spacious and versatile home in a desirable private setting. No wetlands or floozone. Agents see attachments

7 Beds ⋅ 6 Baths ⋅ 24158759 MLS

Tucked away at the end of a private lane, this Nantucket-style Colonial sits on 1.21 level acres with city water, offering privacy, flexibility, and space rarely found in Westport. Rebuilt in 2006 on an existing foundation, the property combines classic shingle-style architecture with thoughtful modern living. The main residence features 5 bedrooms, 4.5 baths, and a dedicated home office. The chef's kitchen with professional appliances opens to a spacious deck overlooking the expansive backyard-ideal for entertaining or everyday living. Multiple gathering spaces include a dramatic skylit den/playroom with vaulted ceilings, perfect for a gym, media room, playroom, or recreation space. A standout feature is the full accessory apartment with 2 bedrooms, kitchenette, full bath, and its own garage, offering excellent flexibility for extended family, guests, au pair, or potential rental income. Set on flat, usable land at the end of a quiet private lane, the property provides a peaceful setting while remaining convenient to Westport amenities, schools, and commuting routes. A rare opportunity to own a spacious and versatile home in a desirable private setting. No wetlands or floozone. Agents see attachments

7 Fermily Ln, Westport

$2,600,000

Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of Westport's most desirable neighborhoods, this beautifully updated Center Hall Colonial offers the perfect blend of timeless charm and modern luxury. Ideally located just minutes from Sherwood Island State Park-with its miles of golden sand beaches, scenic picnic areas, and sweeping views-this home provides easy access to I-95, the Merritt Parkway, and downtown Westport. Set on a picturesque property with a gentle brook at the far end of the level backyard, the home invites peaceful outdoor living with a charming front porch & back porch, expansive deck, and stone patio-ideal for al fresco dining and entertaining. Inside, a gracious two-story foyer with a curved staircase opens to a formal living room with fireplace and a formal dining room complete with butler's pantry and walk-in pantry. The gourmet kitchen features top-of-the-line new Thermador appliances, stone countertops, and a spacious dining area with access to the deck. A family room w/fireplace with Fr doors to an enclosed porch, a pvt office, and a well-designed mudroom with easy access to the two-car garage complete the main level. Upstairs, the primary suite is a true retreat, offering a fireplace, balcony with beautiful property views, walk-in closet, and luxurious bath. Three additional bedrooms share access to full baths, complemented by a large recreation/media room, half bath and convenient second-floor laundry.

4 Beds ⋅ 5 Baths ⋅ 24137404 MLS

Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of Westport's most desirable neighborhoods, this beautifully updated Center Hall Colonial offers the perfect blend of timeless charm and modern luxury. Ideally located just minutes from Sherwood Island State Park-with its miles of golden sand beaches, scenic picnic areas, and sweeping views-this home provides easy access to I-95, the Merritt Parkway, and downtown Westport. Set on a picturesque property with a gentle brook at the far end of the level backyard, the home invites peaceful outdoor living with a charming front porch & back porch, expansive deck, and stone patio-ideal for al fresco dining and entertaining. Inside, a gracious two-story foyer with a curved staircase opens to a formal living room with fireplace and a formal dining room complete with butler's pantry and walk-in pantry. The gourmet kitchen features top-of-the-line new Thermador appliances, stone countertops, and a spacious dining area with access to the deck. A family room w/fireplace with Fr doors to an enclosed porch, a pvt office, and a well-designed mudroom with easy access to the two-car garage complete the main level. Upstairs, the primary suite is a true retreat, offering a fireplace, balcony with beautiful property views, walk-in closet, and luxurious bath. Three additional bedrooms share access to full baths, complemented by a large recreation/media room, half bath and convenient second-floor laundry.

123 Greens Farms Rd, Westport

$2,590,000

*Highest and Best Offers by 5p Sunday April 26* Centrally located on a cul de sac street walking distance to shops and restaurants; minutes to beaches, train and schools. This 4 bedroom Colonial faces east/west for natural light throughout the day with a spacious floor plan and chefs kitchen opening to the family room with fireplace and sliders to the deck and professionally landscaped private backyard-perfect for entertaining. The upper floor features a gracious primary suite with 2 generous walk in closets and a renovated bath. 3 spacious bedrooms and laundry complete the upper floor. See features sheet for all updates and improvements. Welcome to 3 Valley Field Rd!

4 Beds ⋅ 3 Baths ⋅ 24167718 MLS

*Highest and Best Offers by 5p Sunday April 26* Centrally located on a cul de sac street walking distance to shops and restaurants; minutes to beaches, train and schools. This 4 bedroom Colonial faces east/west for natural light throughout the day with a spacious floor plan and chefs kitchen opening to the family room with fireplace and sliders to the deck and professionally landscaped private backyard-perfect for entertaining. The upper floor features a gracious primary suite with 2 generous walk in closets and a renovated bath. 3 spacious bedrooms and laundry complete the upper floor. See features sheet for all updates and improvements. Welcome to 3 Valley Field Rd!

3 Valley Field Rd, Westport

$2,581,433

Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled breakfast nook which allows for basking in nature's splendor while savoring a meal. Fresh interior updates incl. a newly painted family room, updated lighting w/two new chandeliers, a modern backdrop for comfortable everyday living. This precious home has been refreshed throughout to highlight its impressive scale, open flow, & architectural character. The sun drenched primary ste is a true retreat w/a fireplace, spa like bath & generous walk in closet. A flexible floor plan offers multiple living areas & a potential in law suite-ideal for multi generational living, guests, or work from home needs. Four wood burning fireplaces add to the home's timeless appeal. Outdoors, enjoy a thoughtfully landscaped property, the pool & spa, set amidst such soothing natural surroundings. Additional highlights: city water & sewer, a whole house generator, & the exceptional privacy just moments from town. Old Hill is one of Westport's most coveted neighborhoods, known for its quiet, tree lined streets & unbeatable proximity to town, schools, & commuting. A rare opportunity to own a special home.

6 Beds ⋅ 5 Baths ⋅ 24154925 MLS

Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled breakfast nook which allows for basking in nature's splendor while savoring a meal. Fresh interior updates incl. a newly painted family room, updated lighting w/two new chandeliers, a modern backdrop for comfortable everyday living. This precious home has been refreshed throughout to highlight its impressive scale, open flow, & architectural character. The sun drenched primary ste is a true retreat w/a fireplace, spa like bath & generous walk in closet. A flexible floor plan offers multiple living areas & a potential in law suite-ideal for multi generational living, guests, or work from home needs. Four wood burning fireplaces add to the home's timeless appeal. Outdoors, enjoy a thoughtfully landscaped property, the pool & spa, set amidst such soothing natural surroundings. Additional highlights: city water & sewer, a whole house generator, & the exceptional privacy just moments from town. Old Hill is one of Westport's most coveted neighborhoods, known for its quiet, tree lined streets & unbeatable proximity to town, schools, & commuting. A rare opportunity to own a special home.

4 The Fenway, Westport

$2,555,000

A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail, creating a home that feels both enduring and deeply inviting. More recent expansion and remodeling have sensitively enhanced the home. Sunfilled rooms with vaulted ceilings and handhewn finishes offer a balance of scale, with multiple living spaces that transition seamlessly to the outdoors. The grounds unfold in a series of thoughtfully designed moments including lush perennial gardens, winding paths, quiet terraces, and vibrant seasonal color. At the center is a sparkling, oversized pool with a waterfall spa and a fully outfitted stone pool house, which is an ideal retreat for summer living. A heated 4car stone garage with a finished upper level provides flexible space for a studio, office, or possible guest space. Every corner of the property reveals another place to gather, from sunny patios to shaded areas beneath large awnings, all wrapped in exceptional privacy yet minutes to the energy and amenities of downtown Westport. A home where history, beauty, and modern comfort come together with uncommon harmony.

5 Beds ⋅ 3 Baths ⋅ 24161256 MLS

A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail, creating a home that feels both enduring and deeply inviting. More recent expansion and remodeling have sensitively enhanced the home. Sunfilled rooms with vaulted ceilings and handhewn finishes offer a balance of scale, with multiple living spaces that transition seamlessly to the outdoors. The grounds unfold in a series of thoughtfully designed moments including lush perennial gardens, winding paths, quiet terraces, and vibrant seasonal color. At the center is a sparkling, oversized pool with a waterfall spa and a fully outfitted stone pool house, which is an ideal retreat for summer living. A heated 4car stone garage with a finished upper level provides flexible space for a studio, office, or possible guest space. Every corner of the property reveals another place to gather, from sunny patios to shaded areas beneath large awnings, all wrapped in exceptional privacy yet minutes to the energy and amenities of downtown Westport. A home where history, beauty, and modern comfort come together with uncommon harmony.

56 Charcoal Hill Rd, Westport

$2,550,000

Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for everyday living or entertaining. The formal DR offers its own fireplace, blending classic character with warmth and style. The chef's kitchen features two iconic AGA stoves, a walk-in pantry, skylights and a large center island. A charming covered porch offers peaceful morning coffee or evening outdoor dining. Upstairs, the primary suite, is a private sanctuary with vaulted ceilings, sunny sitting room, HW floors, walk-in closet, and spa-like bath incl cast iron soaking tub, oversized shower and elegant finishes. Add'l bedrooms 1 en suite the other w hall bath on the 2nd floor and 2 more Bedrooms on the 3rd floor w Hall Bath are bright and spacious, each w/ HW floors and serene views of the pool and gardens. The LL offers gym area, work space, storage and access to 2 car garage. The fully fenced backyard is a private paradise. Stone walls, mature English gardens and spectacular In-ground pool with auto cover add to the magic of this private oasis. Whole House Generator. Minutes to schools, shopping and town offering the rare combination of luxury, charm, privacy and convenience.

5 Beds ⋅ 5 Baths ⋅ 24165047 MLS

Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for everyday living or entertaining. The formal DR offers its own fireplace, blending classic character with warmth and style. The chef's kitchen features two iconic AGA stoves, a walk-in pantry, skylights and a large center island. A charming covered porch offers peaceful morning coffee or evening outdoor dining. Upstairs, the primary suite, is a private sanctuary with vaulted ceilings, sunny sitting room, HW floors, walk-in closet, and spa-like bath incl cast iron soaking tub, oversized shower and elegant finishes. Add'l bedrooms 1 en suite the other w hall bath on the 2nd floor and 2 more Bedrooms on the 3rd floor w Hall Bath are bright and spacious, each w/ HW floors and serene views of the pool and gardens. The LL offers gym area, work space, storage and access to 2 car garage. The fully fenced backyard is a private paradise. Stone walls, mature English gardens and spectacular In-ground pool with auto cover add to the magic of this private oasis. Whole House Generator. Minutes to schools, shopping and town offering the rare combination of luxury, charm, privacy and convenience.

114 Cross Hwy, Westport

$2,535,000

A rare offering, this remarkable Frazier Peters stone home is a masterful blend of historic character and timeless elegance, set impressively at the top of Charcoal Hill on 2.3 breathtaking acres of fully-gated privacy. Obsessively maintained and reimagined by the current owners, the home was designed with Peters' signature use of native stone, rich wood, and artisan detail, making the residence feel both enduring and warmly livable. Inside, soaring vaulted ceilings, hand-hewn finishes, and sunlit rooms create spaces that invite both grand entertaining and intimate moments. Multiple living areas flow effortlessly to the outdoors, where endless gardens unfold into meandering pathways, quiet terraces, and vibrant seasonal color. At the heart of the grounds is a sparkling pool and fully-outfitted stone pool house, a perfect retreat for summer days. A 4-car heated stone garage off the elegant belgian block driveway also offers a finished upper level, allowing flexibility for a future studio, office, or guest space. Every corner of the property reveals another place to gather, from sunny stone patios to Japanese gardens under shady awnings, all surrounded by lush plantings, offering a sense of escape yet is so close to all that the vibrant town of Westport has to offer. This home is more than a residence-it is a sanctuary of history, beauty, and possibility, where the craftsmanship of a bygone era meets the comforts of today.

5 Beds ⋅ 3 Baths ⋅ 24124875 MLS

A rare offering, this remarkable Frazier Peters stone home is a masterful blend of historic character and timeless elegance, set impressively at the top of Charcoal Hill on 2.3 breathtaking acres of fully-gated privacy. Obsessively maintained and reimagined by the current owners, the home was designed with Peters' signature use of native stone, rich wood, and artisan detail, making the residence feel both enduring and warmly livable. Inside, soaring vaulted ceilings, hand-hewn finishes, and sunlit rooms create spaces that invite both grand entertaining and intimate moments. Multiple living areas flow effortlessly to the outdoors, where endless gardens unfold into meandering pathways, quiet terraces, and vibrant seasonal color. At the heart of the grounds is a sparkling pool and fully-outfitted stone pool house, a perfect retreat for summer days. A 4-car heated stone garage off the elegant belgian block driveway also offers a finished upper level, allowing flexibility for a future studio, office, or guest space. Every corner of the property reveals another place to gather, from sunny stone patios to Japanese gardens under shady awnings, all surrounded by lush plantings, offering a sense of escape yet is so close to all that the vibrant town of Westport has to offer. This home is more than a residence-it is a sanctuary of history, beauty, and possibility, where the craftsmanship of a bygone era meets the comforts of today.

56 Charcoal Hill Rd, Westport

$2,520,000

Perfectly sited on 1.59 acres, this 4-bedroom, 3-bath antique home invites a lifestyle defined by warmth, ease, and understated elegance. Original wideboard floors, an impressive hearth fireplace, and beautifully preserved details create a sense of history, while the open, light-filled layout supports a modern way of living-whether hosting gatherings or enjoying quiet moments at home. The main level is designed for flexibility and comfort, with a first-floor bedroom or office that easily adapts to guests or work-from-home needs. Upstairs, the primary suite offers a calming retreat with a walk-in closet and full bath. Two additional bedrooms, a hall bath and small study provide space for family, creativity or focus. Thoughtful updates, including newer mechanicals and roof ensure a turnkey experience without compromising the home's character. Outdoors, life naturally extends into a private, resort-like setting. A gunite pool and spa invites long summer afternoons, while the expansive, sun-filled lawn sets the stage for entertaining, play or simply unwinding. The detached 2-car garage with heated loft offers a versatile escape-ideal for home gym, studio or relaxed gathering. Moments from town, dining, and all transportation, this is a delightful retreat where every day living feels both effortless and elevated.

4 Beds ⋅ 3 Baths ⋅ 24132813 MLS

Perfectly sited on 1.59 acres, this 4-bedroom, 3-bath antique home invites a lifestyle defined by warmth, ease, and understated elegance. Original wideboard floors, an impressive hearth fireplace, and beautifully preserved details create a sense of history, while the open, light-filled layout supports a modern way of living-whether hosting gatherings or enjoying quiet moments at home. The main level is designed for flexibility and comfort, with a first-floor bedroom or office that easily adapts to guests or work-from-home needs. Upstairs, the primary suite offers a calming retreat with a walk-in closet and full bath. Two additional bedrooms, a hall bath and small study provide space for family, creativity or focus. Thoughtful updates, including newer mechanicals and roof ensure a turnkey experience without compromising the home's character. Outdoors, life naturally extends into a private, resort-like setting. A gunite pool and spa invites long summer afternoons, while the expansive, sun-filled lawn sets the stage for entertaining, play or simply unwinding. The detached 2-car garage with heated loft offers a versatile escape-ideal for home gym, studio or relaxed gathering. Moments from town, dining, and all transportation, this is a delightful retreat where every day living feels both effortless and elevated.

140 Roseville Rd, Westport

$2,492,500

This modern farmhouse was praised for its remodel, receiving the HOBI Award for Outstanding Spec Home in 2017. Set on a secluded + conveniently located Old Hill cul-de-sac, the home has tremendous curb appeal w/an expansive front porch overlooking the wide front lawn. The interior finishes are remarkable, reclaimed + repurposed, the energy-efficient home uses materials such as antique woods, metal, glass + marble to create unique + inviting spaces. Traditional in a sense, w/living + dining rooms flanking the entry, this home is anything but ordinary. The living room can also be a cozy den, as it is now, or function as a 1st floor bedroom with adjacent bathroom. On the opposite side, a barn-style door leads to the dining room, whose focal point is a stunning, custom made chandelier. Flowing easily onto the front porch or into the kitchen, dining guests won't linger at the table too long. Drawn to the center island w/an extended dining table, you will discover the eat-in kitchen is for gathering. Appointed with top-of-the-line appliances + plentiful storage options, the kitchen will delight every home chef. Step into the family room or onto the expansive bluestone patio to further experience this home's welcoming vibe. Upstairs, havens await. From the serene primary bedroom to a second ensuite + two bedrooms w/bath, each person has their retreat. The 3rd floor, lower level + mudroom provide options to meet your needs. Located minutes from all Westport amenities + attractions.

5 Beds ⋅ 5 Baths ⋅ 24116204 MLS

This modern farmhouse was praised for its remodel, receiving the HOBI Award for Outstanding Spec Home in 2017. Set on a secluded + conveniently located Old Hill cul-de-sac, the home has tremendous curb appeal w/an expansive front porch overlooking the wide front lawn. The interior finishes are remarkable, reclaimed + repurposed, the energy-efficient home uses materials such as antique woods, metal, glass + marble to create unique + inviting spaces. Traditional in a sense, w/living + dining rooms flanking the entry, this home is anything but ordinary. The living room can also be a cozy den, as it is now, or function as a 1st floor bedroom with adjacent bathroom. On the opposite side, a barn-style door leads to the dining room, whose focal point is a stunning, custom made chandelier. Flowing easily onto the front porch or into the kitchen, dining guests won't linger at the table too long. Drawn to the center island w/an extended dining table, you will discover the eat-in kitchen is for gathering. Appointed with top-of-the-line appliances + plentiful storage options, the kitchen will delight every home chef. Step into the family room or onto the expansive bluestone patio to further experience this home's welcoming vibe. Upstairs, havens await. From the serene primary bedroom to a second ensuite + two bedrooms w/bath, each person has their retreat. The 3rd floor, lower level + mudroom provide options to meet your needs. Located minutes from all Westport amenities + attractions.

5 Ridgewood Ln, Westport

$2,450,000

OFFERS DUE AT NOON ON MONDAY APRIL 13TH! In the heart of Westport, where charm meets modern living, the expanded cape at 32 Berndale Drive delivers the perfect blend of space, style, and location. Nestled on a quiet, sought-after street just moments from Bedford Middle School and Staples High School, this 5-bedroom, 4-bath residence offers exceptional versatility for today's lifestyle. A welcoming foyer leads into inviting living spaces-including a sun-filled living room with a fireplace, a spacious dining room perfect for gatherings, and a cozy den anchored by a second fireplace. The updated kitchen impresses with top-of-the-line stainless steel appliances, granite countertops, plus ample workspace and storage. Upstairs, the primary suite is a serene retreat featuring a spa-inspired bath with radiant heated floors and a luxurious steam shower. Additional bedrooms, including three on the main floor, provide plenty of room for family, guests, or dedicated office space. The lower level expands your options with a recreation area, workout room, bedroom, laundry, and a full bath-ideal for guests or extended family. Additional highlights include a 2-car attached garage, whole-house generator, and mudroom entry with thoughtful built-in cabinets for easy daily living. An adjacent sunroom makes a perfect home office or studio, overlooking the private backyard. This exceptional home combines comfort, style, and one of the best locations in town.

5 Beds ⋅ 4 Baths ⋅ 24157886 MLS

OFFERS DUE AT NOON ON MONDAY APRIL 13TH! In the heart of Westport, where charm meets modern living, the expanded cape at 32 Berndale Drive delivers the perfect blend of space, style, and location. Nestled on a quiet, sought-after street just moments from Bedford Middle School and Staples High School, this 5-bedroom, 4-bath residence offers exceptional versatility for today's lifestyle. A welcoming foyer leads into inviting living spaces-including a sun-filled living room with a fireplace, a spacious dining room perfect for gatherings, and a cozy den anchored by a second fireplace. The updated kitchen impresses with top-of-the-line stainless steel appliances, granite countertops, plus ample workspace and storage. Upstairs, the primary suite is a serene retreat featuring a spa-inspired bath with radiant heated floors and a luxurious steam shower. Additional bedrooms, including three on the main floor, provide plenty of room for family, guests, or dedicated office space. The lower level expands your options with a recreation area, workout room, bedroom, laundry, and a full bath-ideal for guests or extended family. Additional highlights include a 2-car attached garage, whole-house generator, and mudroom entry with thoughtful built-in cabinets for easy daily living. An adjacent sunroom makes a perfect home office or studio, overlooking the private backyard. This exceptional home combines comfort, style, and one of the best locations in town.

32 Berndale Dr, Westport

$2,425,000

Beautifully set on a side street rise, this stately center hall Colonial has a traditional 4 bedroom, 3.5 bathroom floor plan, plus a bonus wing to suit your flexible space ideas! The main floor includes a front to back stretching living room with the sweetest screened porch, a dining room, an eat-in kitchen with dining area and breakfast bar, and a spacious family room. Upstairs, the primary bedroom has a full bath, three closets and beautiful views of the private property and pool! There are three additional bedrooms, one with an adorable play nook, and a hall bath. The "wing" connects to the main floor and is made up of a living room, office, 2 bedrooms, a full bath and there is a rec room, half baths, storage and a separate entrance on the lower level. A great space for guests, flexible use, and zoned as a legal two family. The 1.35 acre property is bright and blooming already, and the pool is ready for summer fun! Located so close to schools, town and transit, 52 Meadow View Road is ready to be enjoyed!

5 Beds ⋅ 6 Baths ⋅ 24175276 MLS

Beautifully set on a side street rise, this stately center hall Colonial has a traditional 4 bedroom, 3.5 bathroom floor plan, plus a bonus wing to suit your flexible space ideas! The main floor includes a front to back stretching living room with the sweetest screened porch, a dining room, an eat-in kitchen with dining area and breakfast bar, and a spacious family room. Upstairs, the primary bedroom has a full bath, three closets and beautiful views of the private property and pool! There are three additional bedrooms, one with an adorable play nook, and a hall bath. The "wing" connects to the main floor and is made up of a living room, office, 2 bedrooms, a full bath and there is a rec room, half baths, storage and a separate entrance on the lower level. A great space for guests, flexible use, and zoned as a legal two family. The 1.35 acre property is bright and blooming already, and the pool is ready for summer fun! Located so close to schools, town and transit, 52 Meadow View Road is ready to be enjoyed!

52 Meadow View Dr, Westport

$2,425,000

Tucked away in a peaceful, private setting, Hidden Ledge offers the best of Westport living in an ideal Saugatuck/Compo location. This stunning brand-new 4-5 bedroom home combines thoughtful design, quality craftmanship, and effortless access to the area's most loved destinations. Walk along sidewalks or bike the designated bike routes to Compo Beach, Longshore, Saugatuck, downtown shops, acclaimed restaurants, the train, library and Westport's coveted Levitt pavilion. Designed and built by local HOME Design Build, this 3800 SF residence features a clean, timeless aesthetic with an abundance of light thanks to its southern and western exposures. Every detail has been carefully curated, from vertical channel accents, Visual Comfort Lighting and Thermador appliances to the wide-plank white oak floors, custom closets and over-sized Marvin windows. A must-see home in the heart of one of Westport's most desirable locations. #171 Compo Rd. S is one of two NEW Constructions currently being built on a private rear parcel set back from Compo Rd. S. offering city water, sewer and buried power lines. ** The driveway will be maintained jointly by both 171 & 169 Compo Rd. S. As permitted, the property has been organized as a land condominium to allow for the 2 New Constructions to be sold separately.

4 Beds ⋅ 5 Baths ⋅ 24168078 MLS

Tucked away in a peaceful, private setting, Hidden Ledge offers the best of Westport living in an ideal Saugatuck/Compo location. This stunning brand-new 4-5 bedroom home combines thoughtful design, quality craftmanship, and effortless access to the area's most loved destinations. Walk along sidewalks or bike the designated bike routes to Compo Beach, Longshore, Saugatuck, downtown shops, acclaimed restaurants, the train, library and Westport's coveted Levitt pavilion. Designed and built by local HOME Design Build, this 3800 SF residence features a clean, timeless aesthetic with an abundance of light thanks to its southern and western exposures. Every detail has been carefully curated, from vertical channel accents, Visual Comfort Lighting and Thermador appliances to the wide-plank white oak floors, custom closets and over-sized Marvin windows. A must-see home in the heart of one of Westport's most desirable locations. #171 Compo Rd. S is one of two NEW Constructions currently being built on a private rear parcel set back from Compo Rd. S. offering city water, sewer and buried power lines. ** The driveway will be maintained jointly by both 171 & 169 Compo Rd. S. As permitted, the property has been organized as a land condominium to allow for the 2 New Constructions to be sold separately.

171 Compo Rd S, Westport

$2,425,000

This Nantucket-style turnkey retreat has been reimagined and extensively renovated to create the perfect escape by the sea - a captivating and magical experience inside and out. Just a 4-minute walk from picturesque Old Mill Beach and around the corner from Westport's famed Compo Beach, this home blends a seaside-Scandinavian aesthetic with pickled white oak floors, glossy white walls, and sunlit, open spaces. Affectionately nicknamed The Punchbowl for the way it naturally draws friends together, it's long been a place for easy gatherings. Every detail reflects a thoughtful connection to the area - from its lush native gardens to the charming horseshoe crab door knocker that greets you at the front. Inside and out, it's a coastal home designed for living well by the water all year round. With 3 finished floors, 4 bedrooms, 2 updated full baths there's ample space to enjoy. The inviting kitchen features Subzero and Bosch and opens to living room with fireplace and pretty sunroom. The private property is embraced by mature arborvitae and hornbeams, offering a rare sense of privacy and calm just steps from the shoreline in a prime location. Just a bike ride away, enjoy golf, tennis, swimming and boating at Longshore Beach Club Park or a 5- minute drive to the train and restaurants. So close to the shore yet no flood zone and no flood insurance needed. New natural gas mechanicals in 2017. 18 Sherwood Drive isn't just the perfect beach retreat - it's a lifestyle.

4 Beds ⋅ 2 Baths ⋅ 24121533 MLS

This Nantucket-style turnkey retreat has been reimagined and extensively renovated to create the perfect escape by the sea - a captivating and magical experience inside and out. Just a 4-minute walk from picturesque Old Mill Beach and around the corner from Westport's famed Compo Beach, this home blends a seaside-Scandinavian aesthetic with pickled white oak floors, glossy white walls, and sunlit, open spaces. Affectionately nicknamed The Punchbowl for the way it naturally draws friends together, it's long been a place for easy gatherings. Every detail reflects a thoughtful connection to the area - from its lush native gardens to the charming horseshoe crab door knocker that greets you at the front. Inside and out, it's a coastal home designed for living well by the water all year round. With 3 finished floors, 4 bedrooms, 2 updated full baths there's ample space to enjoy. The inviting kitchen features Subzero and Bosch and opens to living room with fireplace and pretty sunroom. The private property is embraced by mature arborvitae and hornbeams, offering a rare sense of privacy and calm just steps from the shoreline in a prime location. Just a bike ride away, enjoy golf, tennis, swimming and boating at Longshore Beach Club Park or a 5- minute drive to the train and restaurants. So close to the shore yet no flood zone and no flood insurance needed. New natural gas mechanicals in 2017. 18 Sherwood Drive isn't just the perfect beach retreat - it's a lifestyle.

18 Sherwood Dr, Westport

$2,418,000

Nestled in a country setting with 2.04 acres of flat, private, beautiful property on one of Westport's most idyllic and picturesque walking streets is a warm and light filled Colonial, in a serene and wooded neighborhood setting. Inside and out, this home has been beautifully updated and maintained. The interior has all the right rooms in all the right places. Rooms are spacious. Main Level: Foyer, Formal Liv/Din Rms, Family Rm w/vaulted ceiling, Kitchen, Breakfast Room, Office and access to Screened-in Porch and large, outdoor Deck. The Lower Level has another Family Rm, Office/Storage Rm, Full Bath, Sauna, Mudroom and tons of storage. Outdoors, you will find a beautifully set tennis/pickleball court with basketball hoop. The peacefulness of this property makes the perfect setting for parties and everyday enjoyment. All of this only 1.3 miles to Coleytown Elem/Middle Schools, less than 3 miles to downtown, and less than 5 miles to the Westport Train station!

4 Beds ⋅ 4 Baths ⋅ 24159296 MLS

Nestled in a country setting with 2.04 acres of flat, private, beautiful property on one of Westport's most idyllic and picturesque walking streets is a warm and light filled Colonial, in a serene and wooded neighborhood setting. Inside and out, this home has been beautifully updated and maintained. The interior has all the right rooms in all the right places. Rooms are spacious. Main Level: Foyer, Formal Liv/Din Rms, Family Rm w/vaulted ceiling, Kitchen, Breakfast Room, Office and access to Screened-in Porch and large, outdoor Deck. The Lower Level has another Family Rm, Office/Storage Rm, Full Bath, Sauna, Mudroom and tons of storage. Outdoors, you will find a beautifully set tennis/pickleball court with basketball hoop. The peacefulness of this property makes the perfect setting for parties and everyday enjoyment. All of this only 1.3 miles to Coleytown Elem/Middle Schools, less than 3 miles to downtown, and less than 5 miles to the Westport Train station!

13 Riverfield Dr, Westport

$2,400,000

Welcome to 18 Silver Brook Road, a beautifully updated and meticulously maintained home set on a level, private acre in one of Westport's most beloved neighborhoods. Located in the sought-after Silver Brook/Bonnie Brook community, this move-in ready residence offers the perfect blend of timeless charm, generous living spaces, and exceptional indoor-outdoor living. The spacious eat-in kitchen flows seamlessly into the vaulted family room, creating a natural gathering place for everyday living. Formal living and dining rooms, a sun-filled office, and a spectacular great room with exposed beams, a fireplace, and French doors opening to the terrace provide exceptional spaces for entertaining and relaxing alike. Upstairs, the serene primary suite features vaulted ceilings, dual walk-in closets, and a spa-inspired bath. Three additional bedrooms, well-appointed baths, and a dedicated laundry room complete the second level. Lovingly cared for and thoughtfully enhanced, the home has seen extensive recent improvements, including pool equipment and liner replacement, smart home upgrades, energy-efficiency enhancements, chimney reconstruction, basement waterproofing, and significant landscaping improvements. Every detail has been attended to, allowing the next owner to move in and immediately enjoy everything this exceptional home has to offer.

4 Beds ⋅ 5 Baths ⋅ 24191350 MLS

Welcome to 18 Silver Brook Road, a beautifully updated and meticulously maintained home set on a level, private acre in one of Westport's most beloved neighborhoods. Located in the sought-after Silver Brook/Bonnie Brook community, this move-in ready residence offers the perfect blend of timeless charm, generous living spaces, and exceptional indoor-outdoor living. The spacious eat-in kitchen flows seamlessly into the vaulted family room, creating a natural gathering place for everyday living. Formal living and dining rooms, a sun-filled office, and a spectacular great room with exposed beams, a fireplace, and French doors opening to the terrace provide exceptional spaces for entertaining and relaxing alike. Upstairs, the serene primary suite features vaulted ceilings, dual walk-in closets, and a spa-inspired bath. Three additional bedrooms, well-appointed baths, and a dedicated laundry room complete the second level. Lovingly cared for and thoughtfully enhanced, the home has seen extensive recent improvements, including pool equipment and liner replacement, smart home upgrades, energy-efficiency enhancements, chimney reconstruction, basement waterproofing, and significant landscaping improvements. Every detail has been attended to, allowing the next owner to move in and immediately enjoy everything this exceptional home has to offer.

18 Silver Brook Rd, Westport

$2,400,000

Tucked at the end of a quiet cul-de-sac in one of Westport's most convenient locations, 6 Imperial Landing offers the perfect blend of privacy, light-filled living, and effortless luxury. Thoughtfully designed and finished across three levels, this 4-bedroom, 3 full and 1 half bath home features well-proportioned rooms, an open layout, and an abundance of natural light throughout. Expansive windows bring the outdoors in, creating a bright and welcoming atmosphere in every space. The heart of the home is a chef's kitchen that flows seamlessly into the main living areas - ideal for both everyday living and entertaining. The primary suite is a true retreat, complete with dream walk-in closets and a newly renovated, spa-like bath designed for comfort and relaxation. The finished lower level adds exceptional versatility, offering a playroom, gym, kitchenette, and an additional bedroom or private office - perfect for today's flexible lifestyle. Set on beautifully landscaped grounds, the property features a waterfall, multiple patios, and a fully fenced backyard, creating a private oasis for relaxing and entertaining. A 3-car garage adds both convenience and functionality. With many recent upgrades throughout, this home is truly move-in ready - simply unpack and enjoy. A rare and special opportunity to experience the full Westport lifestyle, just minutes from the train, restaurants, Longshore, Compo Beach, Saugatuck Center, and downtown.

4 Beds ⋅ 4 Baths ⋅ 24156649 MLS

Tucked at the end of a quiet cul-de-sac in one of Westport's most convenient locations, 6 Imperial Landing offers the perfect blend of privacy, light-filled living, and effortless luxury. Thoughtfully designed and finished across three levels, this 4-bedroom, 3 full and 1 half bath home features well-proportioned rooms, an open layout, and an abundance of natural light throughout. Expansive windows bring the outdoors in, creating a bright and welcoming atmosphere in every space. The heart of the home is a chef's kitchen that flows seamlessly into the main living areas - ideal for both everyday living and entertaining. The primary suite is a true retreat, complete with dream walk-in closets and a newly renovated, spa-like bath designed for comfort and relaxation. The finished lower level adds exceptional versatility, offering a playroom, gym, kitchenette, and an additional bedroom or private office - perfect for today's flexible lifestyle. Set on beautifully landscaped grounds, the property features a waterfall, multiple patios, and a fully fenced backyard, creating a private oasis for relaxing and entertaining. A 3-car garage adds both convenience and functionality. With many recent upgrades throughout, this home is truly move-in ready - simply unpack and enjoy. A rare and special opportunity to experience the full Westport lifestyle, just minutes from the train, restaurants, Longshore, Compo Beach, Saugatuck Center, and downtown.

6 Imperial Lndg, Westport

$2,400,000

**PLEASE SUBMIT ALL OFFERS BY TUESDAY MAY 5TH AT NOON** Classic charm meets modern comfort in this beautifully updated 4-bedroom, 3 full and 1 half bath home, set in one of Westport's most loved walking neighborhoods-just minutes to top schools, vibrant downtown, and an easy hour to NYC. A bright, spacious eat-in kitchen is the heart of the home, opening to a back deck for effortless indoor-outdoor living and flowing into a sun-filled family room with vaulted ceilings and custom built-ins-perfect for gathering or unwinding. Upstairs, the primary suite is a true retreat, featuring a luxe bath with soaking tub, heated floors, heated towel bars, and generous walk-in closets. All baths are beautifully updated, and the home offers incredible flexibility with a first-floor office, elegant living room, and a bonus sunroom ideal as a playroom, lounge, or creative space. Step outside and you'll find your own private resort-a gorgeous heated pool with a chic cabana, made for summer entertaining, long weekends, and effortless staycations. A finished lower level adds even more space to spread out, making this home as functional as it is inviting.

4 Beds ⋅ 4 Baths ⋅ 24168290 MLS

**PLEASE SUBMIT ALL OFFERS BY TUESDAY MAY 5TH AT NOON** Classic charm meets modern comfort in this beautifully updated 4-bedroom, 3 full and 1 half bath home, set in one of Westport's most loved walking neighborhoods-just minutes to top schools, vibrant downtown, and an easy hour to NYC. A bright, spacious eat-in kitchen is the heart of the home, opening to a back deck for effortless indoor-outdoor living and flowing into a sun-filled family room with vaulted ceilings and custom built-ins-perfect for gathering or unwinding. Upstairs, the primary suite is a true retreat, featuring a luxe bath with soaking tub, heated floors, heated towel bars, and generous walk-in closets. All baths are beautifully updated, and the home offers incredible flexibility with a first-floor office, elegant living room, and a bonus sunroom ideal as a playroom, lounge, or creative space. Step outside and you'll find your own private resort-a gorgeous heated pool with a chic cabana, made for summer entertaining, long weekends, and effortless staycations. A finished lower level adds even more space to spread out, making this home as functional as it is inviting.

24 Blue Ribbon Dr, Westport

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