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Tucked away on a picturesque property with a peaceful pond and complete privacy, this custom-built home is truly exceptional. From the moment you step onto the welcoming front porch, you'll feel the warmth and quality throughout. The sunlit kitchen is beautifully appointed with top-of-the-line appliances and a built-in banquette by the cozy fireplace, opening seamlessly to the inviting family room with a stunning fireplace & French doors to the patio. Entertain effortlessly in the elegant dining room w/ butler's pantry & spacious living room. A first-floor office w/ pocket doors offers a quiet retreat for work or study. Upstairs, the primary suite is a sanctuary w/ vaulted ceilings, a private sitting room, balcony overlooking the pond, and a luxurious spa-like bath. Three additional bedrooms, two full baths, & a bright laundry room complete the second floor. A private three-room suite off a separate entrance - including a family area, bedroom, full bath, and loft - provides perfect flexibility for guests, in-laws, or family members. The lower level offers a gym, full bath & sauna for healthy living. Outside, enjoy a resort-like lifestyle with a stunning 50-foot pool w/auto cover, mature landscaping, and breathtaking gardens. Set on 2.69 beautifully landscaped acres in a premier multi-million-dollar neighborhood convenient to everything beautiful Westport offers. This special home presents the perfect blend of elegance, comfort, quality & natural beauty - a true masterpiece.

5 Beds ⋅ 7 Baths ⋅ 24138367 MLS

Tucked away on a picturesque property with a peaceful pond and complete privacy, this custom-built home is truly exceptional. From the moment you step onto the welcoming front porch, you'll feel the warmth and quality throughout. The sunlit kitchen is beautifully appointed with top-of-the-line appliances and a built-in banquette by the cozy fireplace, opening seamlessly to the inviting family room with a stunning fireplace & French doors to the patio. Entertain effortlessly in the elegant dining room w/ butler's pantry & spacious living room. A first-floor office w/ pocket doors offers a quiet retreat for work or study. Upstairs, the primary suite is a sanctuary w/ vaulted ceilings, a private sitting room, balcony overlooking the pond, and a luxurious spa-like bath. Three additional bedrooms, two full baths, & a bright laundry room complete the second floor. A private three-room suite off a separate entrance - including a family area, bedroom, full bath, and loft - provides perfect flexibility for guests, in-laws, or family members. The lower level offers a gym, full bath & sauna for healthy living. Outside, enjoy a resort-like lifestyle with a stunning 50-foot pool w/auto cover, mature landscaping, and breathtaking gardens. Set on 2.69 beautifully landscaped acres in a premier multi-million-dollar neighborhood convenient to everything beautiful Westport offers. This special home presents the perfect blend of elegance, comfort, quality & natural beauty - a true masterpiece.

116 Roseville Rd, Westport

$3,250,000

This beautifully renovated Ward French custom home offers elegant formal spaces, a chef's kitchen, flexible guest and office accommodations, a luxury primary suite, fitness studio and sitting room with balcony. The home's 2,442 square foot lower level offers tremendous untapped potential, providing an opportunity to create customized luxury amenities such as a home theater, golf simulator, wine cellar, wellness spa, or guest retreat. Outdoors a spectacular 20' x 40' pool and spa, multiple entertaining patios, and lush private landscaping create a true retreat. Moments from schools and town amenities, this exceptional Westport residence perfectly balances luxury and everyday living.

5 Beds ⋅ 5 Baths ⋅ 24204780 MLS

This beautifully renovated Ward French custom home offers elegant formal spaces, a chef's kitchen, flexible guest and office accommodations, a luxury primary suite, fitness studio and sitting room with balcony. The home's 2,442 square foot lower level offers tremendous untapped potential, providing an opportunity to create customized luxury amenities such as a home theater, golf simulator, wine cellar, wellness spa, or guest retreat. Outdoors a spectacular 20' x 40' pool and spa, multiple entertaining patios, and lush private landscaping create a true retreat. Moments from schools and town amenities, this exceptional Westport residence perfectly balances luxury and everyday living.

27 Woody Ln, 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

$2,121,000

SELLER IS REQUESTING HIGHEST AND BEST OFFERS BE SUBMITTED BY SUNDAY, NOVEMBER 23RD AT 8PM. Nestled on a quiet, picturesque cul-de-sac, this beautifully maintained home enjoys a prime Westport location-just steps from Staples High School and Bedford Middle School, with direct gated access for ultimate convenience. A short drive brings you to all the amenities Westport has to offer, from shopping and dining to beaches and vibrant town life. Set on a private, level acre, the outdoor spaces are truly exceptional. An expansive deck, dedicated fire-pit area, and fully fenced backyard create the perfect setting for entertaining, play, and year-round enjoyment. Inside, the classic and highly desirable layout features a welcoming two-story foyer, a dramatic great room with exposed beams, vaulted ceilings, and a wood-burning fireplace, an eat-in kitchen with a cozy sitting area, and an oversized dining room ideal for gatherings. The second floor includes all four bedrooms, highlighted by a spacious primary suite with vaulted ceilings, a walk-in closet, and a serene spa bath. The finished lower level offers flexible space for a playroom, gym, office, or all of the above-plus abundant storage. A rare combination of location, layout, and lifestyle-this one won't last.

4 Beds ⋅ 3 Baths ⋅ 24140916 MLS

SELLER IS REQUESTING HIGHEST AND BEST OFFERS BE SUBMITTED BY SUNDAY, NOVEMBER 23RD AT 8PM. Nestled on a quiet, picturesque cul-de-sac, this beautifully maintained home enjoys a prime Westport location-just steps from Staples High School and Bedford Middle School, with direct gated access for ultimate convenience. A short drive brings you to all the amenities Westport has to offer, from shopping and dining to beaches and vibrant town life. Set on a private, level acre, the outdoor spaces are truly exceptional. An expansive deck, dedicated fire-pit area, and fully fenced backyard create the perfect setting for entertaining, play, and year-round enjoyment. Inside, the classic and highly desirable layout features a welcoming two-story foyer, a dramatic great room with exposed beams, vaulted ceilings, and a wood-burning fireplace, an eat-in kitchen with a cozy sitting area, and an oversized dining room ideal for gatherings. The second floor includes all four bedrooms, highlighted by a spacious primary suite with vaulted ceilings, a walk-in closet, and a serene spa bath. The finished lower level offers flexible space for a playroom, gym, office, or all of the above-plus abundant storage. A rare combination of location, layout, and lifestyle-this one won't last.

5 Willow Walk, Westport

$2,050,000

HIGHEST AND BEST DEADLINE: SUNDAY, 6/7 BY 5PM -- Beautifully renovated and perfectly positioned in one of Westport's most coveted and centrally located neighborhoods, this 4-bedroom home offers the turnkey lifestyle today's buyers are seeking, with modern updates, flexible living spaces, and easy access to everything that makes Westport so special. Just minutes from top-ranked schools, downtown shopping and dining, Compo Beach, and transportation -- the location is simply exceptional. The sun-filled main level features a welcoming living room with vaulted ceiling, fireplace, and seamless flow into the dining room. The renovated kitchen showcases crisp white cabinetry, quartz countertops, marble backsplash, chic lighting, and sweeping views of the private backyard. The primary suite has been thoughtfully transformed with a tray ceiling, large walk-in closet, and luxurious marble bath with double vanity, soaking tub, and shower. Two additional bedrooms and a renovated full bath complete the upper level. The lower level offers outstanding flexibility with a fourth bedroom, renovated full bath, convenient home office, and spacious family room featuring custom built-ins, a wood-burning fireplace, and sliders to the patio and backyard. An additional lower level provides a large recreation room, dedicated laundry room, cedar closet, and abundant storage. Move right in and enjoy a turnkey lifestyle in one of Westport's most desirable neighborhoods.

4 Beds ⋅ 3 Baths ⋅ 24179836 MLS

HIGHEST AND BEST DEADLINE: SUNDAY, 6/7 BY 5PM -- Beautifully renovated and perfectly positioned in one of Westport's most coveted and centrally located neighborhoods, this 4-bedroom home offers the turnkey lifestyle today's buyers are seeking, with modern updates, flexible living spaces, and easy access to everything that makes Westport so special. Just minutes from top-ranked schools, downtown shopping and dining, Compo Beach, and transportation -- the location is simply exceptional. The sun-filled main level features a welcoming living room with vaulted ceiling, fireplace, and seamless flow into the dining room. The renovated kitchen showcases crisp white cabinetry, quartz countertops, marble backsplash, chic lighting, and sweeping views of the private backyard. The primary suite has been thoughtfully transformed with a tray ceiling, large walk-in closet, and luxurious marble bath with double vanity, soaking tub, and shower. Two additional bedrooms and a renovated full bath complete the upper level. The lower level offers outstanding flexibility with a fourth bedroom, renovated full bath, convenient home office, and spacious family room featuring custom built-ins, a wood-burning fireplace, and sliders to the patio and backyard. An additional lower level provides a large recreation room, dedicated laundry room, cedar closet, and abundant storage. Move right in and enjoy a turnkey lifestyle in one of Westport's most desirable neighborhoods.

4 Joann Cir, Westport

$1,325,000

Sweet Cottage with In-Ground Pool on a lovely 1-acre property in Westport. Fabulous location, close to everything! This peaceful 3 Bedroom, 2 1/2 Bath home feels worlds away from the hustle and bustle, while being just minutes to Downtown Westport, Compo Beach, Longshore, and major commuter routes. Enjoy a dip in the pool, then relax on the expansive backyard deck and listen to the birds. You'll love the indoor-outdoor lifestyle and entertain with ease, with access to the deck from every room on the main level. A charming arched entrance leads to a gracious Living Room with cozy wood stove, vaulted ceiling and hardwood floors. The Dining Room connects the two sides of the house, with a wall of windows and French doors leading to the deck. The Kitchen allows room for a kitchen table for casual meals, and leads directly to the spacious, light-filled Family Room with vaulted ceilings, skylights and windows on three sides. There's a Half Bath and Laundry on the main level. Upstairs, the Primary Bedroom Suite is a restful retreat with Full Bath with tub and shower, a fireplace, and tree-house views to the backyard. Two additional Bedrooms and a Full Bath complete the second floor. Fantastic opportunity to enjoy the home as an end-user or build your dream house! Please do not enter property without an appointment.

3 Beds ⋅ 3 Baths ⋅ 24190631 MLS

Sweet Cottage with In-Ground Pool on a lovely 1-acre property in Westport. Fabulous location, close to everything! This peaceful 3 Bedroom, 2 1/2 Bath home feels worlds away from the hustle and bustle, while being just minutes to Downtown Westport, Compo Beach, Longshore, and major commuter routes. Enjoy a dip in the pool, then relax on the expansive backyard deck and listen to the birds. You'll love the indoor-outdoor lifestyle and entertain with ease, with access to the deck from every room on the main level. A charming arched entrance leads to a gracious Living Room with cozy wood stove, vaulted ceiling and hardwood floors. The Dining Room connects the two sides of the house, with a wall of windows and French doors leading to the deck. The Kitchen allows room for a kitchen table for casual meals, and leads directly to the spacious, light-filled Family Room with vaulted ceilings, skylights and windows on three sides. There's a Half Bath and Laundry on the main level. Upstairs, the Primary Bedroom Suite is a restful retreat with Full Bath with tub and shower, a fireplace, and tree-house views to the backyard. Two additional Bedrooms and a Full Bath complete the second floor. Fantastic opportunity to enjoy the home as an end-user or build your dream house! Please do not enter property without an appointment.

107 Roseville Rd, Westport

$1,305,000

In the owners' words... We moved to this home looking for an escape from city life and a place to grow our family. It has offered us all of that and more. Every inch of the home serves a purpose, creating a space that feels intentional and complete. The thoughtful size and open layout means we are never far from one another. We can prepare meals in the kitchen while watching our little ones play in the family room. It truly brings a family together. With an abundance of windows, the living area draws the outdoors in and floods our home with natural light. We love enjoying a cup of coffee in the breakfast nook while looking out at the yard and appreciating the beauty of each season. Outside, we all spend countless hours exploring the spacious yard - racing around the house, crossing the bridges, searching for frogs in the brook. This is a home that lets us embrace nature. As much as this home feels like a private retreat, we love the convenience of its central location and being able to get anywhere within Westport, from town to beaches to schools, in a few minutes. Over our years here, this house became a home, a truly special place to grow our family.

3 Beds ⋅ 2 Baths ⋅ 24189044 MLS

In the owners' words... We moved to this home looking for an escape from city life and a place to grow our family. It has offered us all of that and more. Every inch of the home serves a purpose, creating a space that feels intentional and complete. The thoughtful size and open layout means we are never far from one another. We can prepare meals in the kitchen while watching our little ones play in the family room. It truly brings a family together. With an abundance of windows, the living area draws the outdoors in and floods our home with natural light. We love enjoying a cup of coffee in the breakfast nook while looking out at the yard and appreciating the beauty of each season. Outside, we all spend countless hours exploring the spacious yard - racing around the house, crossing the bridges, searching for frogs in the brook. This is a home that lets us embrace nature. As much as this home feels like a private retreat, we love the convenience of its central location and being able to get anywhere within Westport, from town to beaches to schools, in a few minutes. Over our years here, this house became a home, a truly special place to grow our family.

5 Lehn Farm Rd, Westport

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