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

6 Beds ⋅ 7 Baths ⋅ 24064356 MLS

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

3 Tanglewood Ln, Westport

$4,206,625

A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and well-proportioned spaces create an environment that feels both elevated and effortlessly comfortable. At the center of the home, a beautifully designed kitchen opens to expansive living and dining areas, creating a seamless flow for both everyday living and entertaining. The layout flows easily with ample room for work-from-home, multi-generational living, and evolving lifestyle needs. A main-level suite with a full bath provides privacy and versatility-ideal for guests, a dedicated office, or an extended family. Every detail accentuates comfort, function, and understated luxury. A back yard patio with pool abutting a nature preserve offers privacy with open space and the ease of in-town living. Positioned near Nash Pond and close to local nature trails and amenities, the home also offers exceptional convenience-walkable to the Post Road and just minutes to downtown Westport, shopping, dining, and Metro-North train service to New York City. Luxury new construction in Old Hill, Westport, CT-where location, design, and lifestyle align in one of the town's most desirable settings.

6 Beds ⋅ 6 Baths ⋅ 24164137 MLS

A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and well-proportioned spaces create an environment that feels both elevated and effortlessly comfortable. At the center of the home, a beautifully designed kitchen opens to expansive living and dining areas, creating a seamless flow for both everyday living and entertaining. The layout flows easily with ample room for work-from-home, multi-generational living, and evolving lifestyle needs. A main-level suite with a full bath provides privacy and versatility-ideal for guests, a dedicated office, or an extended family. Every detail accentuates comfort, function, and understated luxury. A back yard patio with pool abutting a nature preserve offers privacy with open space and the ease of in-town living. Positioned near Nash Pond and close to local nature trails and amenities, the home also offers exceptional convenience-walkable to the Post Road and just minutes to downtown Westport, shopping, dining, and Metro-North train service to New York City. Luxury new construction in Old Hill, Westport, CT-where location, design, and lifestyle align in one of the town's most desirable settings.

48 Woodside Ave, Westport

$3,600,000

Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an open-concept floor plan enhanced by timeless architectural details and modern upgrades. Sun-drenched living spaces on the main level include a gourmet kitchen, formal living room, dining area, family room, office, and a versatile pool cabana or fitness room-all seamlessly opening to an expansive patio for effortless indoor-outdoor living. Two first-floor ensuite bedrooms provide flexible accommodations. Upstairs, the luxurious primary offers a private retreat, complemented by a large playroom, laundry room, and two additional bedrooms with a shared bath-creating a versatile layout. The resort-style outdoor setting is equally impressive, featuring a gunite pool with spa, pergola, fire pit, outdoor grill area, vegetable garden, and a fully integrated lighting and sound system. Mature, century-old trees, curated specimen plantings, and extensive stonework create a private, park-like oasis. For the buyer seeking privacy while being near all the amenities that Westport has to offer, this extraordinary property combines classic elegance, modern amenities, and an unbeatable location.

5 Beds ⋅ 5 Baths ⋅ 24163168 MLS

Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an open-concept floor plan enhanced by timeless architectural details and modern upgrades. Sun-drenched living spaces on the main level include a gourmet kitchen, formal living room, dining area, family room, office, and a versatile pool cabana or fitness room-all seamlessly opening to an expansive patio for effortless indoor-outdoor living. Two first-floor ensuite bedrooms provide flexible accommodations. Upstairs, the luxurious primary offers a private retreat, complemented by a large playroom, laundry room, and two additional bedrooms with a shared bath-creating a versatile layout. The resort-style outdoor setting is equally impressive, featuring a gunite pool with spa, pergola, fire pit, outdoor grill area, vegetable garden, and a fully integrated lighting and sound system. Mature, century-old trees, curated specimen plantings, and extensive stonework create a private, park-like oasis. For the buyer seeking privacy while being near all the amenities that Westport has to offer, this extraordinary property combines classic elegance, modern amenities, and an unbeatable location.

10 Winding Ln, Westport

$3,175,000

Now more than ever, home is a haven - a place to live, work, relax, and entertain. Privately sited on 1 beautifully landscaped acre in highly sought-after Old Hill, this sophisticated 6,000+ SF home with a brand-new pool offers 6 bedrooms, exceptional living spaces, and breathtaking western sunsets overlooking Earthplace's 62-acre nature sanctuary. A rare blend of privacy, style, and convenience, all within walking distance to town. Designed for both elegant entertaining and comfortable everyday living, the main level features a stunning chef's kitchen with custom cabinetry, pantry, and sun-filled dining area flowing seamlessly into the spacious family room with fireplace - all overlooking the expansive lawns, sparkling pool, and serene natural setting. Formal living and dining rooms provide elegant gathering spaces, while a private office/playroom and guest bedroom with full bath complete the first floor. The luxurious primary serves as a private retreat with sitting area or office, walk-in closet, and spa-inspired bath. Four additional bedrooms, two full baths, and a conveniently located laundry room complete the second level. The top floor offers exceptional bonus space, including a vaulted-ceiling playroom, additional room, and half bath. The lower level provides versatile space featuring a gym, mudroom, and extensive storage. Chic yet welcoming interiors, contemporary amenities, and extraordinary natural surroundings combine to create the ultimate Westport retreat.

6 Beds ⋅ 6 Baths ⋅ 24178615 MLS

Now more than ever, home is a haven - a place to live, work, relax, and entertain. Privately sited on 1 beautifully landscaped acre in highly sought-after Old Hill, this sophisticated 6,000+ SF home with a brand-new pool offers 6 bedrooms, exceptional living spaces, and breathtaking western sunsets overlooking Earthplace's 62-acre nature sanctuary. A rare blend of privacy, style, and convenience, all within walking distance to town. Designed for both elegant entertaining and comfortable everyday living, the main level features a stunning chef's kitchen with custom cabinetry, pantry, and sun-filled dining area flowing seamlessly into the spacious family room with fireplace - all overlooking the expansive lawns, sparkling pool, and serene natural setting. Formal living and dining rooms provide elegant gathering spaces, while a private office/playroom and guest bedroom with full bath complete the first floor. The luxurious primary serves as a private retreat with sitting area or office, walk-in closet, and spa-inspired bath. Four additional bedrooms, two full baths, and a conveniently located laundry room complete the second level. The top floor offers exceptional bonus space, including a vaulted-ceiling playroom, additional room, and half bath. The lower level provides versatile space featuring a gym, mudroom, and extensive storage. Chic yet welcoming interiors, contemporary amenities, and extraordinary natural surroundings combine to create the ultimate Westport retreat.

10 Side Hill, 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

$2,581,433

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

$2,275,000

Update: Offers are due at 6pm on Monday June 15th. Set along one of Westport's most coveted stretches of the Saugatuck River, 18 River Lane is a timeless 1939 English Manor offering a rare blend of architectural character, waterfront serenity, and exceptional potential. Privately sited on 1.38 picturesque acres with sweeping river views and mature landscaping, this six-bedroom residence embodies the elegance and craftsmanship of a bygone era. Rich in period details, the home features graciously scaled rooms, distinctive architectural elements, and an inviting floor plan designed for both comfortable living and entertaining. The versatile layout includes a full walk-out lower-level apartment/studio, ideal for guests, extended family, a home office, creative workspace, or au pair accommodations. The spectacular riverfront setting provides a sense of tranquility and privacy while remaining just minutes from downtown Westport, the train, beaches, and top-rated schools. An extraordinary opportunity exists to further expand the estate, as the adjacent 1.13-acre building lot is also available for purchase, creating the potential for a remarkable compound or future development opportunity. A truly rare offering where historic charm, waterfront living, and limitless possibilities converge.

5 Beds ⋅ 6 Baths ⋅ 24120643 MLS

Update: Offers are due at 6pm on Monday June 15th. Set along one of Westport's most coveted stretches of the Saugatuck River, 18 River Lane is a timeless 1939 English Manor offering a rare blend of architectural character, waterfront serenity, and exceptional potential. Privately sited on 1.38 picturesque acres with sweeping river views and mature landscaping, this six-bedroom residence embodies the elegance and craftsmanship of a bygone era. Rich in period details, the home features graciously scaled rooms, distinctive architectural elements, and an inviting floor plan designed for both comfortable living and entertaining. The versatile layout includes a full walk-out lower-level apartment/studio, ideal for guests, extended family, a home office, creative workspace, or au pair accommodations. The spectacular riverfront setting provides a sense of tranquility and privacy while remaining just minutes from downtown Westport, the train, beaches, and top-rated schools. An extraordinary opportunity exists to further expand the estate, as the adjacent 1.13-acre building lot is also available for purchase, creating the potential for a remarkable compound or future development opportunity. A truly rare offering where historic charm, waterfront living, and limitless possibilities converge.

18 River Ln, Westport

$2,199,120

Wilton Road places you minutes from town and the shoreline. At 234, convenience and privacy coexist. A turn onto a side lane and a set-back approach behind mature trees create a setting that feels distinctly separate from the street. Originally built in 1884, the home has been fully renovated and thoughtfully expanded. A 2024 addition reshaped the main level, enlarging the kitchen and introducing a newly constructed family room anchoring the home. Tall ceilings, open sight lines, and abundant natural light create a sense of volume rarely found in homes of this era. It lives larger than its footprint. The kitchen centers around an oversized island, with a cozy banquette tucked into the corner. A beverage bar and architectural wine display are seamlessly integrated. The flow from kitchen to family room to dining is open and intuitive. Sliders extend to an expansive stone patio with a built-in grill station and fireplace, creating an easy transition between indoors and out. An expansive lawn invites play, set within the safety of the private backyard. Upstairs, the primary suite features a private sitting room, boutique-style dressing room, and a light-filled bath with a soaking tub and glass-enclosed shower. Additional bedrooms are carefully arranged, including a private suite, offering flexibility for guests. Historic at its core and thoughtfully expanded for today. Set where Westport unfolds at your doorstep, and designed with the scale to fully enjoy it.

4 Beds ⋅ 4 Baths ⋅ 24157114 MLS

Wilton Road places you minutes from town and the shoreline. At 234, convenience and privacy coexist. A turn onto a side lane and a set-back approach behind mature trees create a setting that feels distinctly separate from the street. Originally built in 1884, the home has been fully renovated and thoughtfully expanded. A 2024 addition reshaped the main level, enlarging the kitchen and introducing a newly constructed family room anchoring the home. Tall ceilings, open sight lines, and abundant natural light create a sense of volume rarely found in homes of this era. It lives larger than its footprint. The kitchen centers around an oversized island, with a cozy banquette tucked into the corner. A beverage bar and architectural wine display are seamlessly integrated. The flow from kitchen to family room to dining is open and intuitive. Sliders extend to an expansive stone patio with a built-in grill station and fireplace, creating an easy transition between indoors and out. An expansive lawn invites play, set within the safety of the private backyard. Upstairs, the primary suite features a private sitting room, boutique-style dressing room, and a light-filled bath with a soaking tub and glass-enclosed shower. Additional bedrooms are carefully arranged, including a private suite, offering flexibility for guests. Historic at its core and thoughtfully expanded for today. Set where Westport unfolds at your doorstep, and designed with the scale to fully enjoy it.

234 Wilton Rd, Westport

$2,050,000

Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases you best. The welcoming living room with its broad bay window and formal fireplace provides ample room for your guests and the Baby Grand piano! The custom country kitchen is both practical and beautiful with wide plank wood floors, cherry and glass cabinetry, granite counters and a walk-in pantry. The adjoining family room with it's cathedral ceiling is filled with natural light and includes a fireplace, wet bar and French doors that open to a wraparound deck. The most recent addition is an impressive library with long, tall windows set amid tailored built-ins. An additional exterior entry makes it ideal for home office use while the adjacent full bathroom and closet offers the possibility of a first floor bedroom suite. The informal rear foyer includes access to a laundry area, powder room and extra closets. Just beyond is a 2nd private office or den. Upstairs you'll discover the primary suite with full bathroom and walk-in closet, as well as 4 very spacious additional bedrooms. Unseen value found in the new roof, updated mechanicals and whole house generator!

5 Beds ⋅ 4 Baths ⋅ 24178738 MLS

Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases you best. The welcoming living room with its broad bay window and formal fireplace provides ample room for your guests and the Baby Grand piano! The custom country kitchen is both practical and beautiful with wide plank wood floors, cherry and glass cabinetry, granite counters and a walk-in pantry. The adjoining family room with it's cathedral ceiling is filled with natural light and includes a fireplace, wet bar and French doors that open to a wraparound deck. The most recent addition is an impressive library with long, tall windows set amid tailored built-ins. An additional exterior entry makes it ideal for home office use while the adjacent full bathroom and closet offers the possibility of a first floor bedroom suite. The informal rear foyer includes access to a laundry area, powder room and extra closets. Just beyond is a 2nd private office or den. Upstairs you'll discover the primary suite with full bathroom and walk-in closet, as well as 4 very spacious additional bedrooms. Unseen value found in the new roof, updated mechanicals and whole house generator!

34 Pequot Trl, Westport

$2,000,000

Set on a quiet, convenient street in Westport's coveted Old Hill, this charming home captures the essence of Fairfield County living. A picturesque acre with level lawns, a sparkling pool, and expansive patios creates an exceptional outdoor retreat ideal for relaxing or entertaining. A welcoming front porch leads into a thoughtfully renovated interior with beautifully proportioned spaces and distinctive architectural details. The dramatic living room features a soaring beamed cathedral ceiling, fireplace, and oversized windows, while a central butler's pantry connects seamlessly to the dining room with its own fireplace and adjacent wine area. The sunlit gourmet kitchen offers customized cabinetry, a professional gas range, and a banquette dining area. The comfortable family room has a third fireplace. The flexible 4-bedroom layout includes a serene primary suite with a luxurious bath, soaking tub, separate shower, and walk-in closet. Additional bedrooms are spacious, including one with a private sitting area. Outdoor living is enhanced by multiple patios, including a covered space perfect for dining beside the pool. Enjoy close proximity to Earthplace, town, schools, train, and shopping.

4 Beds ⋅ 3 Baths ⋅ 24120677 MLS

Set on a quiet, convenient street in Westport's coveted Old Hill, this charming home captures the essence of Fairfield County living. A picturesque acre with level lawns, a sparkling pool, and expansive patios creates an exceptional outdoor retreat ideal for relaxing or entertaining. A welcoming front porch leads into a thoughtfully renovated interior with beautifully proportioned spaces and distinctive architectural details. The dramatic living room features a soaring beamed cathedral ceiling, fireplace, and oversized windows, while a central butler's pantry connects seamlessly to the dining room with its own fireplace and adjacent wine area. The sunlit gourmet kitchen offers customized cabinetry, a professional gas range, and a banquette dining area. The comfortable family room has a third fireplace. The flexible 4-bedroom layout includes a serene primary suite with a luxurious bath, soaking tub, separate shower, and walk-in closet. Additional bedrooms are spacious, including one with a private sitting area. Outdoor living is enhanced by multiple patios, including a covered space perfect for dining beside the pool. Enjoy close proximity to Earthplace, town, schools, train, and shopping.

5 Tanglewood Ln, Westport

$1,925,000

*SELLERS ARE AKSING FOR HIGHEST AND BEST OFFERS BY 4PM MONDAY JUNE 1ST*Set on a beautifully landscaped, bucolic acre at the top of a quiet cul-de-sac in Westport's coveted Old Hill neighborhood, this charming cottage-style ranch home offers the perfect blend of modern convenience, and luxurious Westport lifestyle. Move-in ready and beautifully maintained it's thoughtful layout is ideal for both everyday living and gracious entertaining. Light pours in through picture windows, French doors, and skylights giving a bright airy feel throughout. At the heart of the home is a stunning chef's kitchen equipped with high-end stainless steel appliances. The open dining area is perfect for feasts with family. Sliders leading to multiple decks make indoor-outdoor living seamless. Relax in the inviting living room with a cozy fireplace, or entertain outdoors on the expansive deck overlooking lush lawns. Retreat to the primary suite that boasts a newly renovated spa-like bath. Two additional bedrooms & full bath complete this level. The lower level offers a family room, perfect for movie nights, as well as office built-ins to WFH. A playroom/rec space, plus a fourth bedroom and full bath, make an ideal setup for guests, in-laws, or au pair. Step outside to your resort-like oasis featuring a stunning, sun-drenched saltwater pool and cabana with bar & Sonos - summer entertaining perfection! Energy efficient with Tesla Solar Roof, newer mechanicals and a generator give peace of mind.

4 Beds ⋅ 4 Baths ⋅ 24176436 MLS

*SELLERS ARE AKSING FOR HIGHEST AND BEST OFFERS BY 4PM MONDAY JUNE 1ST*Set on a beautifully landscaped, bucolic acre at the top of a quiet cul-de-sac in Westport's coveted Old Hill neighborhood, this charming cottage-style ranch home offers the perfect blend of modern convenience, and luxurious Westport lifestyle. Move-in ready and beautifully maintained it's thoughtful layout is ideal for both everyday living and gracious entertaining. Light pours in through picture windows, French doors, and skylights giving a bright airy feel throughout. At the heart of the home is a stunning chef's kitchen equipped with high-end stainless steel appliances. The open dining area is perfect for feasts with family. Sliders leading to multiple decks make indoor-outdoor living seamless. Relax in the inviting living room with a cozy fireplace, or entertain outdoors on the expansive deck overlooking lush lawns. Retreat to the primary suite that boasts a newly renovated spa-like bath. Two additional bedrooms & full bath complete this level. The lower level offers a family room, perfect for movie nights, as well as office built-ins to WFH. A playroom/rec space, plus a fourth bedroom and full bath, make an ideal setup for guests, in-laws, or au pair. Step outside to your resort-like oasis featuring a stunning, sun-drenched saltwater pool and cabana with bar & Sonos - summer entertaining perfection! Energy efficient with Tesla Solar Roof, newer mechanicals and a generator give peace of mind.

2 Grassy Plains Rd, Westport

$1,780,000

Nestled in the coveted Old Hill section of Westport, this exceptional residence offers a rare blend of space, serenity, & timeless appeal. With over 3,200 square feet, the home unfolds beautifully-beginning with a gracious entry foyer, leading into the living room with hardwood floors and anchored by a classic fireplace. The large eat-in kitchen offers double ovens, an abundance of cabinets and marble countertops and opens to both the formal dining room and a more casual dining space with adjoining great room, all unified by gleaming wood floors and bathed in abundant natural light. Designed for both everyday ease and effortless entertaining, the main level also features a thoughtfully appointed mudroom with laundry, located just off the kitchen, offering generous storage for everyone's belongings. Every detail supports comfort and functionality without sacrificing style. Upstairs, four spacious bedrooms provide peaceful retreats. The primary suite is a true sanctuary, complete with a full bath, ample closet space, and a sun-filled porch that easily doubles as a home office, studio, or quiet escape. The finished lower level adds even more flexibility, featuring an office/guest room and a full bath-ideal for today's versatile living needs. Outdoors, the property truly shines. The fabulous backyard is a private oasis, highlighted by a gunite pool with spa and surrounded by lush landscaping-perfect for relaxation and summer gatherings.

4 Beds ⋅ 4 Baths ⋅ 24154644 MLS

Nestled in the coveted Old Hill section of Westport, this exceptional residence offers a rare blend of space, serenity, & timeless appeal. With over 3,200 square feet, the home unfolds beautifully-beginning with a gracious entry foyer, leading into the living room with hardwood floors and anchored by a classic fireplace. The large eat-in kitchen offers double ovens, an abundance of cabinets and marble countertops and opens to both the formal dining room and a more casual dining space with adjoining great room, all unified by gleaming wood floors and bathed in abundant natural light. Designed for both everyday ease and effortless entertaining, the main level also features a thoughtfully appointed mudroom with laundry, located just off the kitchen, offering generous storage for everyone's belongings. Every detail supports comfort and functionality without sacrificing style. Upstairs, four spacious bedrooms provide peaceful retreats. The primary suite is a true sanctuary, complete with a full bath, ample closet space, and a sun-filled porch that easily doubles as a home office, studio, or quiet escape. The finished lower level adds even more flexibility, featuring an office/guest room and a full bath-ideal for today's versatile living needs. Outdoors, the property truly shines. The fabulous backyard is a private oasis, highlighted by a gunite pool with spa and surrounded by lush landscaping-perfect for relaxation and summer gatherings.

39 Marion Rd, Westport

$1,625,000

Discover the perfect balance of comfort and convenience with this unique split-level residence that sits on 1.70 private acres, gracefully set back from the road to offer outstanding privacy and tranquility. Step inside to experience spacious, light-filled interiors with an open floor plan, expansive picture windows, and beautiful hardwood floors that seamlessly connect the living spaces-ideal for both everyday living and entertaining. The home boasts a brand new roof with a transferable warranty and a full house generator for uninterrupted peace of mind. Entertain effortlessly with spacious front and back decks, a built-in bar, and a unique theater room featuring stadium seating for unforgettable movie nights. The home includes an updated main floor powder room and a dedicated private home office with custom built-in cabinetry and shelving, making working from home a breeze. Enjoy the comfort of 5 bedrooms and 4 full & 2 half bathrooms, including three en suite bedrooms. One suite offers a private entrance, perfect for an au pair/multigenerational living. Upstairs, the expansive primary suite provides a serene retreat with a charming bay window and built-in bench. Additional living space offers versatility for a variety of lifestyle needs. Outdoor amenities are designed for family fun and relaxation, featuring a hot tub, zip line, trampoline, and two tree swings. The decks overlook the serene, private setting, providing the ideal backdrop for gatherings large and small

5 Beds ⋅ 6 Baths ⋅ 24168672 MLS

Discover the perfect balance of comfort and convenience with this unique split-level residence that sits on 1.70 private acres, gracefully set back from the road to offer outstanding privacy and tranquility. Step inside to experience spacious, light-filled interiors with an open floor plan, expansive picture windows, and beautiful hardwood floors that seamlessly connect the living spaces-ideal for both everyday living and entertaining. The home boasts a brand new roof with a transferable warranty and a full house generator for uninterrupted peace of mind. Entertain effortlessly with spacious front and back decks, a built-in bar, and a unique theater room featuring stadium seating for unforgettable movie nights. The home includes an updated main floor powder room and a dedicated private home office with custom built-in cabinetry and shelving, making working from home a breeze. Enjoy the comfort of 5 bedrooms and 4 full & 2 half bathrooms, including three en suite bedrooms. One suite offers a private entrance, perfect for an au pair/multigenerational living. Upstairs, the expansive primary suite provides a serene retreat with a charming bay window and built-in bench. Additional living space offers versatility for a variety of lifestyle needs. Outdoor amenities are designed for family fun and relaxation, featuring a hot tub, zip line, trampoline, and two tree swings. The decks overlook the serene, private setting, providing the ideal backdrop for gatherings large and small

52 Partrick Rd, Westport

$1,599,876

Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The front to back living room with marble fireplace offers peaceful views through expansive windows. The formal dining room with picture window is adjacent to a generous country kitchen featuring a bay window, granite countertops, a gas cooktop and double ovens. The oversized family room boasts a vaulted ceiling and access to main level laundry area. The rear of the house features a 58 ft long deck overlooking private acreage. The home contains 5 bedrooms and 4 full bathrooms. The primary suite includes a full bathroom, dressing area, linen closet and a walk in closet with built-in armoire. This home has fabulous closet space with each bedroom offering a minimum of 2 closets. The walk out lower level hosts a private den / office with wet bar and sliders to a stone patio. There is an additional laundry area and storage space that leads to an oversized 2 bay garage. Central air conditioning will keep you comfortable during summer months while five zone heating, Thermopane windows and extra insulation keep this home energy efficient all year long. Westport's luxury shops, fine restaurants, relaxing beaches and award winning school system combine to make this an irresistible value!

5 Beds ⋅ 4 Baths ⋅ 24170706 MLS

Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The front to back living room with marble fireplace offers peaceful views through expansive windows. The formal dining room with picture window is adjacent to a generous country kitchen featuring a bay window, granite countertops, a gas cooktop and double ovens. The oversized family room boasts a vaulted ceiling and access to main level laundry area. The rear of the house features a 58 ft long deck overlooking private acreage. The home contains 5 bedrooms and 4 full bathrooms. The primary suite includes a full bathroom, dressing area, linen closet and a walk in closet with built-in armoire. This home has fabulous closet space with each bedroom offering a minimum of 2 closets. The walk out lower level hosts a private den / office with wet bar and sliders to a stone patio. There is an additional laundry area and storage space that leads to an oversized 2 bay garage. Central air conditioning will keep you comfortable during summer months while five zone heating, Thermopane windows and extra insulation keep this home energy efficient all year long. Westport's luxury shops, fine restaurants, relaxing beaches and award winning school system combine to make this an irresistible value!

30 Pequot Trl, Westport

$1,310,000

Classic Old Hill Charm Where Character Meets Convenience Incredible location in the heart of Old Hill, with the ability to walk to downtown Westport shopping & dining, Kings Highway Elementary School, & Earthplace. This warm & inviting 3 BD, 2 BTH historic home is filled with classic details & thoughtful updates throughout. The expansive living room features a beautiful fieldstone fireplace and a cozy bay-window reading nook, while the spacious dining room sits adjacent to a bright kitchen with updated appliances, including a Viking range. A flexible first-floor bedroom, perfect as a guest room, office, or den, along with a renovated full bath, completes the main level. Upstairs, the large primary bedroom offers wonderful natural light, an updated hall bath, and generous closet space (with potential for a laundry area). Two additional bedrooms provide versatility for guests, family, or workspace needs. The dry, level lot includes a deck off the kitchen & a rear patio, ideal for outdoor dining &relaxation. With potential to add a garage or expand the living space, this home combines timeless charm, opportunity, & one of Westport's most desirable locations. The property boasts the convenience of gas, city water, & sewer. Situated in a fantastic location, it's just a few minutes from the train station, making commuting a breeze. Exciting plans for remodeling, crafted by a local architect known for their work on historical homes, are included to inspire your vision.

3 Beds ⋅ 2 Baths ⋅ 24169070 MLS

Classic Old Hill Charm Where Character Meets Convenience Incredible location in the heart of Old Hill, with the ability to walk to downtown Westport shopping & dining, Kings Highway Elementary School, & Earthplace. This warm & inviting 3 BD, 2 BTH historic home is filled with classic details & thoughtful updates throughout. The expansive living room features a beautiful fieldstone fireplace and a cozy bay-window reading nook, while the spacious dining room sits adjacent to a bright kitchen with updated appliances, including a Viking range. A flexible first-floor bedroom, perfect as a guest room, office, or den, along with a renovated full bath, completes the main level. Upstairs, the large primary bedroom offers wonderful natural light, an updated hall bath, and generous closet space (with potential for a laundry area). Two additional bedrooms provide versatility for guests, family, or workspace needs. The dry, level lot includes a deck off the kitchen & a rear patio, ideal for outdoor dining &relaxation. With potential to add a garage or expand the living space, this home combines timeless charm, opportunity, & one of Westport's most desirable locations. The property boasts the convenience of gas, city water, & sewer. Situated in a fantastic location, it's just a few minutes from the train station, making commuting a breeze. Exciting plans for remodeling, crafted by a local architect known for their work on historical homes, are included to inspire your vision.

39 Kings Hwy N, Westport

$1,050,000

BRAND NEW ROOF. BRAND NEW BOILER. Even though the house is not new, it sure will seem like it is! But that isn't the best part about this house...this lovely home is in a catbird seat location! Walking distance to the best Westport has to offer...Main Street shops & restaurants, the library, the Levitt Pavilion, the farmers' market or the Playhouse. A quick bike ride to Longshore Park or Compo beach, this home sits in the heart of Westport. Newly painted and refreshed, this home is so easy to enjoy. A lovely, sunlit living room with a wood-burning fireplace is wonderful for entertaining. A roomy, eat-in kitchen is adjacent to the dining room with sliding doors that leads out to a deck. Having dinner on the deck is like dining among the treetops! Two ample-sized bedrooms and a hall bath, along with the Primary bedroom with ensuite bath, complete the upper floor of this home. The downstairs has a possible 4th bedroom/office/workout space (you decide how to use it!) and a large family room with a fireplace and sliders that lead out to the newly landscaped backyard. To complete the package, this house has a very convenient attached two-car garage. The only thing better than the location, is the wonderful home itself!

3 Beds ⋅ 3 Baths ⋅ 24174435 MLS

BRAND NEW ROOF. BRAND NEW BOILER. Even though the house is not new, it sure will seem like it is! But that isn't the best part about this house...this lovely home is in a catbird seat location! Walking distance to the best Westport has to offer...Main Street shops & restaurants, the library, the Levitt Pavilion, the farmers' market or the Playhouse. A quick bike ride to Longshore Park or Compo beach, this home sits in the heart of Westport. Newly painted and refreshed, this home is so easy to enjoy. A lovely, sunlit living room with a wood-burning fireplace is wonderful for entertaining. A roomy, eat-in kitchen is adjacent to the dining room with sliding doors that leads out to a deck. Having dinner on the deck is like dining among the treetops! Two ample-sized bedrooms and a hall bath, along with the Primary bedroom with ensuite bath, complete the upper floor of this home. The downstairs has a possible 4th bedroom/office/workout space (you decide how to use it!) and a large family room with a fireplace and sliders that lead out to the newly landscaped backyard. To complete the package, this house has a very convenient attached two-car garage. The only thing better than the location, is the wonderful home itself!

5 Edge Hill Trl, Westport

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