Wealthwiserealty.com Search Results

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every space has been curated with an uncompromising attention to detail-from custom millwork to premium finishes-creating an environment that is as functional as it is beautiful. Set on one of the most coveted streets in Southport, this property offers the perfect balance of privacy and proximity. Just a short stroll to the harbor and Long Island Sound, the setting recalls the charm of Nantucket or the Hamptons while retaining the unmistakable character of Southport. The transformation of the entire estate-including the main house, guest house, pool, and pool house-is nothing short of remarkable. The extensive list of upgrades and enhancements is too comprehensive to list here; this is a home that must be seen to be fully appreciated. Experience 260 Willow Street-a residence that invites you to live beautifully, entertain effortlessly, and enjoy the best of coastal village life.

7 Beds ⋅ 7 Baths ⋅ 24109531 MLS

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every space has been curated with an uncompromising attention to detail-from custom millwork to premium finishes-creating an environment that is as functional as it is beautiful. Set on one of the most coveted streets in Southport, this property offers the perfect balance of privacy and proximity. Just a short stroll to the harbor and Long Island Sound, the setting recalls the charm of Nantucket or the Hamptons while retaining the unmistakable character of Southport. The transformation of the entire estate-including the main house, guest house, pool, and pool house-is nothing short of remarkable. The extensive list of upgrades and enhancements is too comprehensive to list here; this is a home that must be seen to be fully appreciated. Experience 260 Willow Street-a residence that invites you to live beautifully, entertain effortlessly, and enjoy the best of coastal village life.

260 Willow St, Fairfield

$9,050,000

"Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of privacy, presence, and provenance. Designed in 1927 by renowned architect Francis Hamilton, the home was later owned by Broadway producer John C. Wilson and his partner, the celebrated English playwright Noel Coward. Over the years, "Pebbles" became a summer retreat for a remarkable circle of artists and tastemakers, including Vivien Leigh, Laurence Olivier, Diana Vreeland, Jean Schlumberger, and Richard Rodgers. Lovingly maintained and thoughtfully updated by each subsequent owner, the estate retains its grand-scale interiors, period details, and refined elegance. Expansive formal rooms, high ceilings, and sunlit living spaces open to terraces that overlook the water and the meticulously landscaped grounds, anchored by a striking pool featured in the 1968 film *The Swimmer* starring Burt Lancaster. This is more than a home-it's a rare opportunity to own a landmark property with architectural pedigree, cinematic history, and enduring coastal beauty-all within minutes of Southport Village, beaches, and NYC-bound trains.

6 Beds ⋅ 9 Baths ⋅ 24090854 MLS

"Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of privacy, presence, and provenance. Designed in 1927 by renowned architect Francis Hamilton, the home was later owned by Broadway producer John C. Wilson and his partner, the celebrated English playwright Noel Coward. Over the years, "Pebbles" became a summer retreat for a remarkable circle of artists and tastemakers, including Vivien Leigh, Laurence Olivier, Diana Vreeland, Jean Schlumberger, and Richard Rodgers. Lovingly maintained and thoughtfully updated by each subsequent owner, the estate retains its grand-scale interiors, period details, and refined elegance. Expansive formal rooms, high ceilings, and sunlit living spaces open to terraces that overlook the water and the meticulously landscaped grounds, anchored by a striking pool featured in the 1968 film *The Swimmer* starring Burt Lancaster. This is more than a home-it's a rare opportunity to own a landmark property with architectural pedigree, cinematic history, and enduring coastal beauty-all within minutes of Southport Village, beaches, and NYC-bound trains.

828 Sasco Hill Rd, Fairfield

$4,850,000

Welcome to 222 Sunnie Holme Drive, a stunning residence nestled in the highly sought-after Fairfield community. Rebuilt with an eye to all original period details and nuances. This beautifully maintained home offers spacious and inviting living areas filled with natural light, perfect for both entertaining and comfortable everyday living. Enjoy modern amenities combined with classic charm, featuring an updated kitchen, elegant finishes, and generous bedrooms. Step outside to a private backyard oasis and custom pool ideal for relaxation and outdoor gatherings. This home provides the perfect blend of suburban tranquility and urban accessibility. Don't miss the opportunity to make this exceptional property your new home!

5 Beds ⋅ 6 Baths ⋅ 24143584 MLS

Welcome to 222 Sunnie Holme Drive, a stunning residence nestled in the highly sought-after Fairfield community. Rebuilt with an eye to all original period details and nuances. This beautifully maintained home offers spacious and inviting living areas filled with natural light, perfect for both entertaining and comfortable everyday living. Enjoy modern amenities combined with classic charm, featuring an updated kitchen, elegant finishes, and generous bedrooms. Step outside to a private backyard oasis and custom pool ideal for relaxation and outdoor gatherings. This home provides the perfect blend of suburban tranquility and urban accessibility. Don't miss the opportunity to make this exceptional property your new home!

Fairfield

$4,700,000

Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's kitchen opens to elegant dining and living areas, with French doors to a bluestone terrace designed for candlelit dinners under the stars. A first-floor guest suite with a full bath provides flexibility and privacy, while upstairs, four additional bedrooms-including a serene primary suite-offer refined comfort and room to breathe. Beyond the home, the grounds unfold like a private resort. A two-story pool house features a full kitchen, bath, and playful loft. A climate-controlled barn houses a Trackman 4 golf simulator, sauna, and space for training or unwinding. Outdoors, discover a saltwater pool and spa, sport court, vegetable gardens, wildflower meadow with carved walking trails, orchard of apple, cherry, and peach trees, and a cider press-all with a private path leading to the Patterson Club. Whether for weekends or a lifetime, this estate elevates every season and every gathering-minutes from town, yet a world apart.

5 Beds ⋅ 5 Baths ⋅ 24127092 MLS

Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's kitchen opens to elegant dining and living areas, with French doors to a bluestone terrace designed for candlelit dinners under the stars. A first-floor guest suite with a full bath provides flexibility and privacy, while upstairs, four additional bedrooms-including a serene primary suite-offer refined comfort and room to breathe. Beyond the home, the grounds unfold like a private resort. A two-story pool house features a full kitchen, bath, and playful loft. A climate-controlled barn houses a Trackman 4 golf simulator, sauna, and space for training or unwinding. Outdoors, discover a saltwater pool and spa, sport court, vegetable gardens, wildflower meadow with carved walking trails, orchard of apple, cherry, and peach trees, and a cider press-all with a private path leading to the Patterson Club. Whether for weekends or a lifetime, this estate elevates every season and every gathering-minutes from town, yet a world apart.

2281 Redding Rd, Fairfield

$4,300,000

IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with exceptional trim work and french doors leading to an outdoor covered porch and inviting blue stone patio. Expansive family room with welcoming fireplace and grand living room with a second fireplace for festive family celebrations. Chef's kitchen with custom cabinetry and top of the line appliances offers a separate eating area with bay windows. Bedrooms are generously sized with full marble baths and top quality vanities. Opulent master suite provides a perfect place to retreat. The finished third floor with additional living space will surely suits your family and Lifestyle. Two extra generously sized bedrooms, a full bath, room for a movie theater, a playroom or gym complete this unique oversized beach sanctuary. OPTIONS available: Sauna, Elevator, Wine parlor, Outdoor loggia and Pool. LAND OF 0.31 ACRE IS RARE and OVERSIZED. A TRUE GEM. Please note that is project is a proposed built and that the pictures depicted here are from local and renowned builder NewGenerationHealthyHomes. Inquire today to view or request builder's extensive portfolio and finishes

6 Beds ⋅ 6 Baths ⋅ 24155905 MLS

IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with exceptional trim work and french doors leading to an outdoor covered porch and inviting blue stone patio. Expansive family room with welcoming fireplace and grand living room with a second fireplace for festive family celebrations. Chef's kitchen with custom cabinetry and top of the line appliances offers a separate eating area with bay windows. Bedrooms are generously sized with full marble baths and top quality vanities. Opulent master suite provides a perfect place to retreat. The finished third floor with additional living space will surely suits your family and Lifestyle. Two extra generously sized bedrooms, a full bath, room for a movie theater, a playroom or gym complete this unique oversized beach sanctuary. OPTIONS available: Sauna, Elevator, Wine parlor, Outdoor loggia and Pool. LAND OF 0.31 ACRE IS RARE and OVERSIZED. A TRUE GEM. Please note that is project is a proposed built and that the pictures depicted here are from local and renowned builder NewGenerationHealthyHomes. Inquire today to view or request builder's extensive portfolio and finishes

378 Penfield Rd, Fairfield

$4,300,000

Nestled on one of Fairfield's most coveted streets where the beach, town, & coastal charm are just steps away- this extraordinary 1944 farmhouse is a rare offering that blends timeless New England character w/ every modern luxury. Once part of the Annie B. Jennings estate, this completely reimagined 4,038 sq. ft. residence sits on nearly 3/4 of an acre, an unheard-of expanse in the beach area. Behind its storybook facade lies an entertainer's paradise & a sanctuary for everyday living. Inside, you'll find 2 luxurious primary suites, a state-of-the-art chef's kitchen designed for culinary artistry, & a great room that seamlessly connects warmth, light, & space. The home also incl a private office, fitness studio, & home theatre-every detail curated for today's lifestyle. Step outside, & the magic continues. A courtyard dining area for 14 sets the stage for unforgettable gatherings. Heated saltwater pool, 8-person hot tub, & flagstone patio w/fpl invite relaxation under the stars. An impressive covered outdoor kitchen w/ seating for 6 makes al fresco living effortless & elegant. Completing this dream property is a 2-story barn feat addl garage & legal in-law aptmt-perfect for guests, extended family, or creative studio space. W/ 5 total fireplaces, & a 5 car garage, a workshop, & meticulous craftsmanship throughout, this home represents the pinnacle of Fairfield coastal living. Every inch tells a story. Every detail exudes grace. This is more than a home- it's a legacy property

4 Beds ⋅ 4 Baths ⋅ 24119620 MLS

Nestled on one of Fairfield's most coveted streets where the beach, town, & coastal charm are just steps away- this extraordinary 1944 farmhouse is a rare offering that blends timeless New England character w/ every modern luxury. Once part of the Annie B. Jennings estate, this completely reimagined 4,038 sq. ft. residence sits on nearly 3/4 of an acre, an unheard-of expanse in the beach area. Behind its storybook facade lies an entertainer's paradise & a sanctuary for everyday living. Inside, you'll find 2 luxurious primary suites, a state-of-the-art chef's kitchen designed for culinary artistry, & a great room that seamlessly connects warmth, light, & space. The home also incl a private office, fitness studio, & home theatre-every detail curated for today's lifestyle. Step outside, & the magic continues. A courtyard dining area for 14 sets the stage for unforgettable gatherings. Heated saltwater pool, 8-person hot tub, & flagstone patio w/fpl invite relaxation under the stars. An impressive covered outdoor kitchen w/ seating for 6 makes al fresco living effortless & elegant. Completing this dream property is a 2-story barn feat addl garage & legal in-law aptmt-perfect for guests, extended family, or creative studio space. W/ 5 total fireplaces, & a 5 car garage, a workshop, & meticulous craftsmanship throughout, this home represents the pinnacle of Fairfield coastal living. Every inch tells a story. Every detail exudes grace. This is more than a home- it's a legacy property

174 Sunnieholme Dr, Fairfield

$4,250,000

Set on one of Fairfield's most coveted streets, this is the kind of home families spend years hoping will become available. Set on 3.35 acres on prestigious Verna Hill Road, adjacent to Fairfield Country Day School, this is the kind of property that becomes the backdrop for decades of memories. Summer afternoons by the pool and spa. Holiday dinners that bring everyone together. At the center of it all is a home that balances grandeur with warmth. The gracious living and dining rooms, with their soaring ceilings, were made for entertaining, while the sunroom and family room naturally become gathering places, overlooking the pool, patio, and grounds. Tucked away, a richly paneled office with fireplace and French doors opening to a private garden provides a quiet retreat. The four bedrooms are all en-suite, with the primary offering his and her baths and dressing rooms, along with the convenience of an elevator. Connected by a breezeway, the detached three-car garage is topped by a 1,000 sqft studio apartment (5th bedroom) with a kitchen, full bath, and washer and dryer-ideal for au-pair, extended family or gym. Outside, resort-style amenities include a pool, spa, expansive terraces overlooking the flat manicured backyard. Properties like this are increasingly rare: timeless architecture, one of Fairfield's most coveted addresses, all just minutes from town, beaches, and country clubs.

4 Beds ⋅ 8 Baths ⋅ 24180502 MLS

Set on one of Fairfield's most coveted streets, this is the kind of home families spend years hoping will become available. Set on 3.35 acres on prestigious Verna Hill Road, adjacent to Fairfield Country Day School, this is the kind of property that becomes the backdrop for decades of memories. Summer afternoons by the pool and spa. Holiday dinners that bring everyone together. At the center of it all is a home that balances grandeur with warmth. The gracious living and dining rooms, with their soaring ceilings, were made for entertaining, while the sunroom and family room naturally become gathering places, overlooking the pool, patio, and grounds. Tucked away, a richly paneled office with fireplace and French doors opening to a private garden provides a quiet retreat. The four bedrooms are all en-suite, with the primary offering his and her baths and dressing rooms, along with the convenience of an elevator. Connected by a breezeway, the detached three-car garage is topped by a 1,000 sqft studio apartment (5th bedroom) with a kitchen, full bath, and washer and dryer-ideal for au-pair, extended family or gym. Outside, resort-style amenities include a pool, spa, expansive terraces overlooking the flat manicured backyard. Properties like this are increasingly rare: timeless architecture, one of Fairfield's most coveted addresses, all just minutes from town, beaches, and country clubs.

800 Verna Hill Rd, Fairfield

$4,200,000

Location, Location, Location plus an exceptional design all come together at 153 Birch Road. Ideally located in one of the most sought-after Beach neighborhoods, this FEMA compliant home sits on a rare level, stunning, .34-acre lot and offers over 4800 square feet of high end, solid construction and brilliant architecture. Features that make this home a true stand out include 11 spacious rooms including 5 bedrooms along with custom details and impressive recent upgrades throughout. Step outside to your own true hidden paradise complete with a Gunite pool, outdoor kitchen, shower, multiple patios and seating areas filled with vibrant, colorful plantings with professional landscaping. A third-floor walkup provides exciting expansion potential offering over 1000 square feet of unfinished space currently being used for storage. Seconds to the elementary school and an easy stroll to miles of sandy beaches, town, parks, beach clubs and so much more. This stunning home delivers the best of the best.

5 Beds ⋅ 4 Baths ⋅ 24170280 MLS

Location, Location, Location plus an exceptional design all come together at 153 Birch Road. Ideally located in one of the most sought-after Beach neighborhoods, this FEMA compliant home sits on a rare level, stunning, .34-acre lot and offers over 4800 square feet of high end, solid construction and brilliant architecture. Features that make this home a true stand out include 11 spacious rooms including 5 bedrooms along with custom details and impressive recent upgrades throughout. Step outside to your own true hidden paradise complete with a Gunite pool, outdoor kitchen, shower, multiple patios and seating areas filled with vibrant, colorful plantings with professional landscaping. A third-floor walkup provides exciting expansion potential offering over 1000 square feet of unfinished space currently being used for storage. Seconds to the elementary school and an easy stroll to miles of sandy beaches, town, parks, beach clubs and so much more. This stunning home delivers the best of the best.

153 Birch Rd, Fairfield

$4,200,000

*New Tax Assessment for 2026-2027 $1,949,290. In an idyllic Greenfield Hill location, this magnificently proportioned and beautifully constructed 6642 square foot Colonial enjoys a gorgeous, gated 2 Acre property, manicured and landscaped to perfection, with an expansive two-tiered Granite Terrace and stunning 20' by 40' gunite Pool overlooking sweeping lawns. Greatly contributing to the overall symmetry of this classic design, the luxurious floor plan includes five Bedrooms, six full baths, two powder rooms, (Living Room, Den, and Family Room each with Fireplace), formal Dining Room, Designer Kitchen, Summer Kitchen, stunning Primary Suite with 2 Full Baths, open Great Room on the 2nd floor, as well as versatile, finished space on the third floor. The spacious finished Lower Level (additional 1528 square feet) features a fabulous Gym with mirrored walls, Recreation area and Full Bath. Embracing a lifestyle of serenity & enjoyable entertainment, refined architectural elements and custom detailing throughout combine to further enhance this very stately and impeccable home. First Floor: 2-story Entrance Hall with herringbone wood flooring. Powder Room with tile flooring and pedestal sink. Living Room with hardwood flooring. Den beyond sharing double-sided gas Fireplace. Office with hardwood flooring, cherry cabinetry and built-ins, and ceiling fan. Summer Kitchen (with access to Pool Terrace) with porcelain tile flooring, PLEASE OPEN ADDENDUM FOR FURTHER DESCRIPTION

5 Beds ⋅ 8 Baths ⋅ 24149979 MLS

*New Tax Assessment for 2026-2027 $1,949,290. In an idyllic Greenfield Hill location, this magnificently proportioned and beautifully constructed 6642 square foot Colonial enjoys a gorgeous, gated 2 Acre property, manicured and landscaped to perfection, with an expansive two-tiered Granite Terrace and stunning 20' by 40' gunite Pool overlooking sweeping lawns. Greatly contributing to the overall symmetry of this classic design, the luxurious floor plan includes five Bedrooms, six full baths, two powder rooms, (Living Room, Den, and Family Room each with Fireplace), formal Dining Room, Designer Kitchen, Summer Kitchen, stunning Primary Suite with 2 Full Baths, open Great Room on the 2nd floor, as well as versatile, finished space on the third floor. The spacious finished Lower Level (additional 1528 square feet) features a fabulous Gym with mirrored walls, Recreation area and Full Bath. Embracing a lifestyle of serenity & enjoyable entertainment, refined architectural elements and custom detailing throughout combine to further enhance this very stately and impeccable home. First Floor: 2-story Entrance Hall with herringbone wood flooring. Powder Room with tile flooring and pedestal sink. Living Room with hardwood flooring. Den beyond sharing double-sided gas Fireplace. Office with hardwood flooring, cherry cabinetry and built-ins, and ceiling fan. Summer Kitchen (with access to Pool Terrace) with porcelain tile flooring, PLEASE OPEN ADDENDUM FOR FURTHER DESCRIPTION

110 Queens Grant Dr, Fairfield

$4,160,000

HIGHEST AND BEST OFFERS DUE TUESDAY 1/27/26 5PM. A Quiet Circle. A Life Well-Lived. Just twelve homes. One private green. And a sense of calm that's increasingly hard to find. Welcome to 324 Sunnieholme Drive - a custom Jack Franzen-designed residence nestled in one of Fairfield Beach's most coveted enclaves. Built in 2010 and inspired by timeless architecture, this home captures the romance of shingle style with the ease of modern coastal living. Inside, sunlight moves freely. The floor plan feels open yet personal, with spaces that flow and flex as life changes. A first-floor office with full bath becomes a guest suite when needed. A finished third floor offers privacy and comfort. The lower level invites play, fitness, or escape. Out back, a private patio offers the perfect place for morning coffee or evening wine - surrounded by garden greenery and the hush of a quiet lane. All just a walk away from the beach, train, and the town center. Meticulously kept and quietly refined, this is beachside living without pretense. Custom. Turnkey. Enduringly rare.

4 Beds ⋅ 5 Baths ⋅ 24148564 MLS

HIGHEST AND BEST OFFERS DUE TUESDAY 1/27/26 5PM. A Quiet Circle. A Life Well-Lived. Just twelve homes. One private green. And a sense of calm that's increasingly hard to find. Welcome to 324 Sunnieholme Drive - a custom Jack Franzen-designed residence nestled in one of Fairfield Beach's most coveted enclaves. Built in 2010 and inspired by timeless architecture, this home captures the romance of shingle style with the ease of modern coastal living. Inside, sunlight moves freely. The floor plan feels open yet personal, with spaces that flow and flex as life changes. A first-floor office with full bath becomes a guest suite when needed. A finished third floor offers privacy and comfort. The lower level invites play, fitness, or escape. Out back, a private patio offers the perfect place for morning coffee or evening wine - surrounded by garden greenery and the hush of a quiet lane. All just a walk away from the beach, train, and the town center. Meticulously kept and quietly refined, this is beachside living without pretense. Custom. Turnkey. Enduringly rare.

324 Sunnieholme Dr, Fairfield

$3,900,000

Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill,this exceptional 7,100-sqft estate is set on two meticulously landscaped acres,offering a rare blend of timeless elegance & modern luxury.A sweeping two-tiered bluestone terrace frames the stunning 20'x40' heated gunite pool,creating a private outdoor sanctuary designed for both relaxation & grand-scale entertaining.Completely reimagined by an award-winning local builder in 2015,every finish & detail has been thoughtfully curated with an uncompromising eye for quality,craftsmanship,& design.Spanning 4 finished levels,the home offers 5-6 bedrooms;luxurious primary suites on both the 1st & 2nd floors,ideal for multigenerational living or accommodating guests with ease.Refined architectural elements & bespoke millwork enhance the home's stately presence,while a seamless flow of formal & informal spaces elevates everyday living.Designed for effortless entertaining, the gracious formal living room & the elegant dining room both feature gas fireplaces.The classic butler's pantry is complemented by a stylish wet bar. The chef's kitchen is a showpiece,featuring a dramatic 10-ft island with 2" Calacutta marble,dual sinks,premium appliances & a coffered ceiling,all opening to a spectacular 2-story family room anchored by a floor-to-ceiling stone fireplace.

6 Beds ⋅ 7 Baths ⋅ 24165267 MLS

Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill,this exceptional 7,100-sqft estate is set on two meticulously landscaped acres,offering a rare blend of timeless elegance & modern luxury.A sweeping two-tiered bluestone terrace frames the stunning 20'x40' heated gunite pool,creating a private outdoor sanctuary designed for both relaxation & grand-scale entertaining.Completely reimagined by an award-winning local builder in 2015,every finish & detail has been thoughtfully curated with an uncompromising eye for quality,craftsmanship,& design.Spanning 4 finished levels,the home offers 5-6 bedrooms;luxurious primary suites on both the 1st & 2nd floors,ideal for multigenerational living or accommodating guests with ease.Refined architectural elements & bespoke millwork enhance the home's stately presence,while a seamless flow of formal & informal spaces elevates everyday living.Designed for effortless entertaining, the gracious formal living room & the elegant dining room both feature gas fireplaces.The classic butler's pantry is complemented by a stylish wet bar. The chef's kitchen is a showpiece,featuring a dramatic 10-ft island with 2" Calacutta marble,dual sinks,premium appliances & a coffered ceiling,all opening to a spectacular 2-story family room anchored by a floor-to-ceiling stone fireplace.

129 Quarter Horse Ln, Fairfield

$3,800,000

Luxury Living on the Fairfield/Westport Border. "Sturges Manor" is an exceptional 6-bedroom, 8-bath estate that offers a rare combination of privacy, elegance, and resort-style amenities - just minutes from the Post Road and 50 miles from NYC. Enjoy multiple town centers and restaurants. The house features expansive, sun-filled interiors ideal for everyday living and entertaining. Recently refreshed with new paint and carpeting, the home includes a formal living and dining room, a large eat-in kitchen, and generously sized family spaces throughout. The finished lower level is designed for wellness and fun, with a 6-person sauna, steam shower, and a spacious game/media room. A third-floor flex space offers the perfect spot for a yoga studio, home office, or quiet retreat. The outdoor experience is equally impressive: a heated saltwater pool and spa, tranquil ponds, a cascading waterfall, and lush manicured lawns set the tone for relaxed luxury. Entertain with ease using the fully equipped outdoor kitchen and fire pit, or shoot hoops on your basketball court. Additional highlights include a full gym, wine cellar, elevator servicing all levels, and two separate 3-car garages-ideal for collectors. A pre-paid landscaping contract through 2031 ensures the grounds remain pristine year-round. Close proximity to some the CT's best private and public schools. This is an extraordinary opportunity to enjoy the best of Fairfield County in a setting that feels like a private resort

6 Beds ⋅ 9 Baths ⋅ 24114747 MLS

Luxury Living on the Fairfield/Westport Border. "Sturges Manor" is an exceptional 6-bedroom, 8-bath estate that offers a rare combination of privacy, elegance, and resort-style amenities - just minutes from the Post Road and 50 miles from NYC. Enjoy multiple town centers and restaurants. The house features expansive, sun-filled interiors ideal for everyday living and entertaining. Recently refreshed with new paint and carpeting, the home includes a formal living and dining room, a large eat-in kitchen, and generously sized family spaces throughout. The finished lower level is designed for wellness and fun, with a 6-person sauna, steam shower, and a spacious game/media room. A third-floor flex space offers the perfect spot for a yoga studio, home office, or quiet retreat. The outdoor experience is equally impressive: a heated saltwater pool and spa, tranquil ponds, a cascading waterfall, and lush manicured lawns set the tone for relaxed luxury. Entertain with ease using the fully equipped outdoor kitchen and fire pit, or shoot hoops on your basketball court. Additional highlights include a full gym, wine cellar, elevator servicing all levels, and two separate 3-car garages-ideal for collectors. A pre-paid landscaping contract through 2031 ensures the grounds remain pristine year-round. Close proximity to some the CT's best private and public schools. This is an extraordinary opportunity to enjoy the best of Fairfield County in a setting that feels like a private resort

1084 Sturges Hwy, Fairfield

$3,750,000

Step into history in the heart of Southport Village, where this location doesn't get any better! On Pequot Ave, and just a short stroll to the beach, harbor, village shops, dining, library, and train to New York City, this beautifully restored 1853 Colonial was once home to Miss Augusta Smith's Seaside Seminary. The residence has been reimagined for today with warmth, elegance, and every modern comfort. Behind its gracious front porch and classic lines, over 4,300 sf unfold with light-filled rooms, hardwood floors, and three wood-burning fireplaces that invite gathering. The home offers six bedrooms, including two primary suites--one on the first floor and one upstairs--each a private retreat with spa-like baths. A country kitchen with its own fireplace, banquette dining, and French doors to the terrace becomes the heart of the home, perfect for everyday living and entertaining. Outdoors, stone walls and sweeping lawns frame a terrace where privacy abounds, and that looks over the guest cottage, playhouse, and charming red barn. The 1,100 sf cottage, complete with living room, kitchen, and bedroom suite, is ideal for visitors or extended stays. This one-of-a-kind gem of a property blends history, charm, and convenience... an opportunity to live in one of Connecticut's most cherished seaside villages!

6 Beds ⋅ 6 Baths ⋅ 24132810 MLS

Step into history in the heart of Southport Village, where this location doesn't get any better! On Pequot Ave, and just a short stroll to the beach, harbor, village shops, dining, library, and train to New York City, this beautifully restored 1853 Colonial was once home to Miss Augusta Smith's Seaside Seminary. The residence has been reimagined for today with warmth, elegance, and every modern comfort. Behind its gracious front porch and classic lines, over 4,300 sf unfold with light-filled rooms, hardwood floors, and three wood-burning fireplaces that invite gathering. The home offers six bedrooms, including two primary suites--one on the first floor and one upstairs--each a private retreat with spa-like baths. A country kitchen with its own fireplace, banquette dining, and French doors to the terrace becomes the heart of the home, perfect for everyday living and entertaining. Outdoors, stone walls and sweeping lawns frame a terrace where privacy abounds, and that looks over the guest cottage, playhouse, and charming red barn. The 1,100 sf cottage, complete with living room, kitchen, and bedroom suite, is ideal for visitors or extended stays. This one-of-a-kind gem of a property blends history, charm, and convenience... an opportunity to live in one of Connecticut's most cherished seaside villages!

944 Pequot Ave, Fairfield

$3,700,000

Gracious and storied, this 1859 antique residence is set in the heart of coveted Southport Village and offers timeless character paired with a rare, walk-to-harbor lifestyle. Cherished by the same family since 1974, the home enjoys some views of Southport Harbor and is just steps from the village center, shops, dining, train, and waterfront. The interior showcases classic period details, including multiple fireplaces, wide-plank floors, and thoughtfully integrated modern conveniences such as an elevator. The expansive living room features a fireplace and built-in bookshelves and French doors that open to a screened-in patio-an ideal setting for outdoor dining and entertaining. The home offers four bedrooms, three of which are en-suite, providing comfort and privacy for family and guests. Set on a level, usable yard, the property also includes a barn with renovation potential, offering exciting possibilities for studio, workshop, or additional living space (subject to approvals). A rare opportunity to own a distinguished Southport Village antique with harbor views, provenance, and exceptional potential. Not in Historic District.

4 Beds ⋅ 5 Baths ⋅ 24150693 MLS

Gracious and storied, this 1859 antique residence is set in the heart of coveted Southport Village and offers timeless character paired with a rare, walk-to-harbor lifestyle. Cherished by the same family since 1974, the home enjoys some views of Southport Harbor and is just steps from the village center, shops, dining, train, and waterfront. The interior showcases classic period details, including multiple fireplaces, wide-plank floors, and thoughtfully integrated modern conveniences such as an elevator. The expansive living room features a fireplace and built-in bookshelves and French doors that open to a screened-in patio-an ideal setting for outdoor dining and entertaining. The home offers four bedrooms, three of which are en-suite, providing comfort and privacy for family and guests. Set on a level, usable yard, the property also includes a barn with renovation potential, offering exciting possibilities for studio, workshop, or additional living space (subject to approvals). A rare opportunity to own a distinguished Southport Village antique with harbor views, provenance, and exceptional potential. Not in Historic District.

130 Willow St, Fairfield

$3,700,000

Rare beach area gem that checks ALL the boxes! With almost 5,000 square feet of living space on a rare and very private .43-acre lot, this highly custom home features a heated saltwater pool, spa/hot tub, 4-floor elevator, and so many high-end amenities. With an exceptionally wide footprint, this home offers 5-6 bedrooms, 4.5 bathrooms, 9-foot ceilings, front and back decks, a full-house generator, and an expansive garage with room for cars, bikes, and plenty of storage. The first floor boasts an open floor plan with stunning chef's kitchen, complete with an island, Sub-Zero refrigerator, and high-end appliances. A spacious family room with gas fireplace adjoins the living room and kitchen, while a butler's pantry connects to the dining room. The primary suite features a spa-like bath with radiant floor heating, an expansive walk-in closet, a gas fireplace, and a private balcony overlooking the yard and pool. 3 additional bedrooms with en-suite baths and a laundry room with sink complete this level. The third floor - also accessible by elevator - offers 2 more bedrooms and a fantastic recreation room with a serving bar, beverage center, an additional full bath, and generous storage. Custom paneling, built-ins, and window treatments throughout. Extensive, mature landscaping with irrigation in both front and back yards creates a lush outdoor setting, complete with a covered entertaining area on the lower level. Downtown, the train, and the beach are all just steps away!

5 Beds ⋅ 5 Baths ⋅ 24117845 MLS

Rare beach area gem that checks ALL the boxes! With almost 5,000 square feet of living space on a rare and very private .43-acre lot, this highly custom home features a heated saltwater pool, spa/hot tub, 4-floor elevator, and so many high-end amenities. With an exceptionally wide footprint, this home offers 5-6 bedrooms, 4.5 bathrooms, 9-foot ceilings, front and back decks, a full-house generator, and an expansive garage with room for cars, bikes, and plenty of storage. The first floor boasts an open floor plan with stunning chef's kitchen, complete with an island, Sub-Zero refrigerator, and high-end appliances. A spacious family room with gas fireplace adjoins the living room and kitchen, while a butler's pantry connects to the dining room. The primary suite features a spa-like bath with radiant floor heating, an expansive walk-in closet, a gas fireplace, and a private balcony overlooking the yard and pool. 3 additional bedrooms with en-suite baths and a laundry room with sink complete this level. The third floor - also accessible by elevator - offers 2 more bedrooms and a fantastic recreation room with a serving bar, beverage center, an additional full bath, and generous storage. Custom paneling, built-ins, and window treatments throughout. Extensive, mature landscaping with irrigation in both front and back yards creates a lush outdoor setting, complete with a covered entertaining area on the lower level. Downtown, the train, and the beach are all just steps away!

254 Penfield Rd, Fairfield

$3,600,000

OPEN HOUSE TODAY HAS BEEN CANCELED. 349 Beach Road is the kind of home that instantly slows the pace of life - where mornings begin with walks to the beach, afternoons are spent by the pool beneath coastal skies, and evenings gather naturally around the warmth of the fire. Just moments from Fairfield's shoreline, the home offers a lifestyle that feels both relaxed and effortlessly elevated. Thoughtfully reimagined over time, the residence blends timeless character with refined modern living. Extensive updates and renovations completed throughout the past five years have elevated nearly every corner of the home while preserving its historic soul. Sunlight pours through open gathering spaces designed for connection and entertaining, while exposed antique beams, heart pine floors, and multiple fireplaces create warmth and authenticity throughout. The expanded kitchen serves as the heart of the home - a place for lingering dinners, holiday traditions, and everyday moments that feel special. Outside, the grounds feel private and resort-inspired, framed by mature landscaping and lush laurel plantings, with seamless indoor-outdoor flow to the newly added pool, stone terraces, and beautifully designed outdoor spaces. Whether hosting summer gatherings after a day by the water or enjoying quiet evenings under the glow of landscape lighting, every space was designed for effortless living. 3

5 Beds ⋅ 5 Baths ⋅ 24175220 MLS

OPEN HOUSE TODAY HAS BEEN CANCELED. 349 Beach Road is the kind of home that instantly slows the pace of life - where mornings begin with walks to the beach, afternoons are spent by the pool beneath coastal skies, and evenings gather naturally around the warmth of the fire. Just moments from Fairfield's shoreline, the home offers a lifestyle that feels both relaxed and effortlessly elevated. Thoughtfully reimagined over time, the residence blends timeless character with refined modern living. Extensive updates and renovations completed throughout the past five years have elevated nearly every corner of the home while preserving its historic soul. Sunlight pours through open gathering spaces designed for connection and entertaining, while exposed antique beams, heart pine floors, and multiple fireplaces create warmth and authenticity throughout. The expanded kitchen serves as the heart of the home - a place for lingering dinners, holiday traditions, and everyday moments that feel special. Outside, the grounds feel private and resort-inspired, framed by mature landscaping and lush laurel plantings, with seamless indoor-outdoor flow to the newly added pool, stone terraces, and beautifully designed outdoor spaces. Whether hosting summer gatherings after a day by the water or enjoying quiet evenings under the glow of landscape lighting, every space was designed for effortless living. 3

349 Beach Rd, Fairfield

$3,525,000

Gorgeous waterfront retreat w/ breathtaking panoramic LI Sound views & miles of walkable sandy beach. This exceptional FEMA compliant coastal retreat includes a private boat dock w/ an additional two-car garage on the creek side, creating endless opportunities for waterfront enjoyment. Featuring 3 levels of spacious living, w/ 8 rooms & 4 full baths, thoughtfully designed for everyday living & entertaining. Enjoy stunning water views from every level w/ BOTH sunrises & colorful sunsets from multiple balconies that invite you to relax & take in the scenery. Highlights include a sun drenched open floor plan, high-end Wolf and Sub-Zero appliances, custom built-ins, a gas fireplace & white oak hardwood floors throughout. Additional private rooms offer flexibility for work, guests, or quiet retreat. A rare & highly desirable 1st floor bedroom w/ full bath is perfect for guests, in-laws or a home office. Outdoor living is just as impressive w/ an oversized patio ideal for entertaining, dining or simply watching sailboats glide by during regattas. Amazing features include roof top deck, 2 separate garages, driveway parking for up to 10 cars (a true rarity in the beach area), home generator, outdoor shower & a Tesla charging station. Ideally located close to town, train, parks, school & shopping. Beach walks, boating, peace & tranquility await in your very own premier luxury coastal home - Welcome home to 2101-2102 Fairfield Beach Road.

4 Beds ⋅ 4 Baths ⋅ 24142758 MLS

Gorgeous waterfront retreat w/ breathtaking panoramic LI Sound views & miles of walkable sandy beach. This exceptional FEMA compliant coastal retreat includes a private boat dock w/ an additional two-car garage on the creek side, creating endless opportunities for waterfront enjoyment. Featuring 3 levels of spacious living, w/ 8 rooms & 4 full baths, thoughtfully designed for everyday living & entertaining. Enjoy stunning water views from every level w/ BOTH sunrises & colorful sunsets from multiple balconies that invite you to relax & take in the scenery. Highlights include a sun drenched open floor plan, high-end Wolf and Sub-Zero appliances, custom built-ins, a gas fireplace & white oak hardwood floors throughout. Additional private rooms offer flexibility for work, guests, or quiet retreat. A rare & highly desirable 1st floor bedroom w/ full bath is perfect for guests, in-laws or a home office. Outdoor living is just as impressive w/ an oversized patio ideal for entertaining, dining or simply watching sailboats glide by during regattas. Amazing features include roof top deck, 2 separate garages, driveway parking for up to 10 cars (a true rarity in the beach area), home generator, outdoor shower & a Tesla charging station. Ideally located close to town, train, parks, school & shopping. Beach walks, boating, peace & tranquility await in your very own premier luxury coastal home - Welcome home to 2101-2102 Fairfield Beach Road.

2101 Fairfield Beach Rd, Fairfield

$3,500,000

A beautiful, new construction WATERFRONT home complete w/ BOAT DOCK, ROOFTOP & ELEVATOR awaits & will be ready for you to enjoy by June. Offering 3 levels of luxurious living - this gorgeous coastal home sets a new standard for smart design & top tier craftsmanship. Enjoy seamless access to every floor w/ a private elevator from the ground to the 3rd level PLUS a stairway to an additional rooftop deck where you can enjoy unobstructed panoramic water views & colorful sunsets. With 10 spacious rooms, this home combines comfort, elegance & functionality. The ground level loggia opens up to the water, while the private dock in front of your home offers in the moment convenience for boaters. Across the road, your own additional property provides great extra parking - a rare bonus in waterfront living. Every detail reflects luxury; white oak hardwood flooring, Pella Lifestyle series wood interior windows, custom interior doors, state of the art appliances including wine column & beverage chiller, custom cabinetry in kitchen & baths, Hardie Board exterior siding for lasting durability, decks on 2nd, 3rd & rooftop levels all w/ stunning views, radiant heated flooring in the ground-level entry & primary bath & spa-like bathrooms w/ premium finishes. This home is flooded w/ natural light throughout the day, enhancing your daily living. Living life with quality!

4 Beds ⋅ 4 Baths ⋅ 24150388 MLS

A beautiful, new construction WATERFRONT home complete w/ BOAT DOCK, ROOFTOP & ELEVATOR awaits & will be ready for you to enjoy by June. Offering 3 levels of luxurious living - this gorgeous coastal home sets a new standard for smart design & top tier craftsmanship. Enjoy seamless access to every floor w/ a private elevator from the ground to the 3rd level PLUS a stairway to an additional rooftop deck where you can enjoy unobstructed panoramic water views & colorful sunsets. With 10 spacious rooms, this home combines comfort, elegance & functionality. The ground level loggia opens up to the water, while the private dock in front of your home offers in the moment convenience for boaters. Across the road, your own additional property provides great extra parking - a rare bonus in waterfront living. Every detail reflects luxury; white oak hardwood flooring, Pella Lifestyle series wood interior windows, custom interior doors, state of the art appliances including wine column & beverage chiller, custom cabinetry in kitchen & baths, Hardie Board exterior siding for lasting durability, decks on 2nd, 3rd & rooftop levels all w/ stunning views, radiant heated flooring in the ground-level entry & primary bath & spa-like bathrooms w/ premium finishes. This home is flooded w/ natural light throughout the day, enhancing your daily living. Living life with quality!

345 Old Dam Rd, Fairfield

$3,425,000

Set well back from the road on two acres in Greenfield Hill, this remarkable residence is approached by a tree-lined drive of pavers, cobblestone and Belgian block. Completely rebuilt and reimagined with the quality and craftsmanship of new construction, nearly 8,000 square feet unfold across three levels with four bedrooms, six full and two half baths, wide-plank oak floors, expansive windows and tranquil pond views. A sun-filled atrium with soaring 20-foot ceilings introduces gracious living and entertaining spaces accented by multiple fireplaces. The tremendous chef's kitchen features quartzite surfaces, abundant cabinetry, a walk-in pantry and Sub-Zero, Wolf and Miele appliances, including dual refrigeration, ovens and dishwashers. The primary suite features a barrel-vaulted ceiling, fireplace and separate his-and-hers areas, each with a walk-in closet and private marble bath with heated floors. Two additional en suite bedrooms and laundry complete the upper level. The light-filled walkout lower level includes a fireplace, kitchenette, wine room, full bath, exercise room, second laundry and flexible recreation/media space. Terraces with a fire pit and built-in grill overlook the peaceful grounds. Smart-home technology, a generator, all-new systems and a standing-seam metal roof add turnkey ease. The Ridge offers a staffed gated entrance, private roads, mature trees, clubhouse, heated pool, tennis and pickleball.

4 Beds ⋅ 8 Baths ⋅ 24200803 MLS

Set well back from the road on two acres in Greenfield Hill, this remarkable residence is approached by a tree-lined drive of pavers, cobblestone and Belgian block. Completely rebuilt and reimagined with the quality and craftsmanship of new construction, nearly 8,000 square feet unfold across three levels with four bedrooms, six full and two half baths, wide-plank oak floors, expansive windows and tranquil pond views. A sun-filled atrium with soaring 20-foot ceilings introduces gracious living and entertaining spaces accented by multiple fireplaces. The tremendous chef's kitchen features quartzite surfaces, abundant cabinetry, a walk-in pantry and Sub-Zero, Wolf and Miele appliances, including dual refrigeration, ovens and dishwashers. The primary suite features a barrel-vaulted ceiling, fireplace and separate his-and-hers areas, each with a walk-in closet and private marble bath with heated floors. Two additional en suite bedrooms and laundry complete the upper level. The light-filled walkout lower level includes a fireplace, kitchenette, wine room, full bath, exercise room, second laundry and flexible recreation/media space. Terraces with a fire pit and built-in grill overlook the peaceful grounds. Smart-home technology, a generator, all-new systems and a standing-seam metal roof add turnkey ease. The Ridge offers a staffed gated entrance, private roads, mature trees, clubhouse, heated pool, tennis and pickleball.

475 Fence Row Dr, Fairfield

$3,300,000

Exceptional scale and timeless elegance define this impressive 5-bedroom, 6-bath residence offering over 8,200 square feet of refined living space in one of Fairfield's most desirable locations. Thoughtfully designed for both grand entertaining and comfortable everyday living, the home features expansive sun-filled rooms, high ceilings, and a seamless flow throughout the main living areas. A spacious chef's kitchen opens to inviting gathering spaces, while multiple formal and informal rooms provide flexibility for today's lifestyle. Generously sized bedrooms include a luxurious primary suite designed as a private retreat. The home's substantial footprint allows for ideal work-from-home options, recreation areas, and guest accommodations. Set on a beautifully landscaped property, the outdoor space offers privacy and room to enjoy the serene surroundings. Conveniently located near Fairfield's vibrant downtown, beaches, train access, dining, and top amenities, this property presents a rare opportunity to own a home of significant size and presence in a premier Fairfield setting.

5 Beds ⋅ 6 Baths ⋅ 24161914 MLS

Exceptional scale and timeless elegance define this impressive 5-bedroom, 6-bath residence offering over 8,200 square feet of refined living space in one of Fairfield's most desirable locations. Thoughtfully designed for both grand entertaining and comfortable everyday living, the home features expansive sun-filled rooms, high ceilings, and a seamless flow throughout the main living areas. A spacious chef's kitchen opens to inviting gathering spaces, while multiple formal and informal rooms provide flexibility for today's lifestyle. Generously sized bedrooms include a luxurious primary suite designed as a private retreat. The home's substantial footprint allows for ideal work-from-home options, recreation areas, and guest accommodations. Set on a beautifully landscaped property, the outdoor space offers privacy and room to enjoy the serene surroundings. Conveniently located near Fairfield's vibrant downtown, beaches, train access, dining, and top amenities, this property presents a rare opportunity to own a home of significant size and presence in a premier Fairfield setting.

145 Galloping Hill Rd, Fairfield

$3,292,000

Welcome to 99 Old Academy Road, a distinguished Cape originally reimagined by local architect Richard Swann and thoughtfully expanded in 2019 by Alex Esposito. Arched-top dormers elevate the architecture, blending tradition with luxury. This residence offers 6 bedrooms plus a private two-level guest suite, 7 full / 3 half baths, all set on 2+ acres in lower Greenfield Hill. At the heart of the home, the kitchen offers an open layout with a spacious dining area, custom cabinetry, a floor-to-ceiling glass wine display, and walk-in pantry. The kitchen flows seamlessly onto a bluestone patio with a double-sided fireplace, perfect for indoor-outdoor living. The kitchen leads to the lower level, featuring a stone bar in the game room, a 10-seat cinema, and ample storage. The family room, with its built-ins, poolside views, and gas fireplace, offers an inviting year-round retreat, the main level also includes a private office. Upstairs, every bedroom is paired with its own private bath, each with a unique design. The custom mahogany library serves as a passage to the East Wing, where the main level offers a gym, poolside lounge, & outdoor shower, while the upper-level features three additional en-suite bedrooms and a second laundry room. Outdoors, enjoy wrap-a-round mahogany decks, multiple bluestone patios, a heated pool, volleyball court, pergola gardens, and fruit trees. 99 Old Academy Road isn't just a home, it's a lifestyle of elegance, comfort, and unforgettable spaces.

6 Beds ⋅ 8 Baths ⋅ 24130154 MLS

Welcome to 99 Old Academy Road, a distinguished Cape originally reimagined by local architect Richard Swann and thoughtfully expanded in 2019 by Alex Esposito. Arched-top dormers elevate the architecture, blending tradition with luxury. This residence offers 6 bedrooms plus a private two-level guest suite, 7 full / 3 half baths, all set on 2+ acres in lower Greenfield Hill. At the heart of the home, the kitchen offers an open layout with a spacious dining area, custom cabinetry, a floor-to-ceiling glass wine display, and walk-in pantry. The kitchen flows seamlessly onto a bluestone patio with a double-sided fireplace, perfect for indoor-outdoor living. The kitchen leads to the lower level, featuring a stone bar in the game room, a 10-seat cinema, and ample storage. The family room, with its built-ins, poolside views, and gas fireplace, offers an inviting year-round retreat, the main level also includes a private office. Upstairs, every bedroom is paired with its own private bath, each with a unique design. The custom mahogany library serves as a passage to the East Wing, where the main level offers a gym, poolside lounge, & outdoor shower, while the upper-level features three additional en-suite bedrooms and a second laundry room. Outdoors, enjoy wrap-a-round mahogany decks, multiple bluestone patios, a heated pool, volleyball court, pergola gardens, and fruit trees. 99 Old Academy Road isn't just a home, it's a lifestyle of elegance, comfort, and unforgettable spaces.

99 Old Academy Rd, Fairfield

$3,210,000

Welcome to a truly exceptional opportunity-a direct waterfront compound offering expansive views of Long Island Sound, a dock, &endless showstopping sunsets. This remarkable property features 2 residences: a fully renovated, FEMA-compliant main house AND a charming, income-generating guest cottage.The Main Residence (320)is a modern coastal retreat offering 3,129 sq ft of sun-drenched living space, gourmet kitchen, 3/4 bedrooms &4 full baths. Renovated to perfection in 2018, this light-filled home is a celebration of indoor-outdoor living, w/expansive windows framing unobstructed water views &an open floor plan ideal for entertaining. The wraparound private deck offers front-row seating to endless sunsets &salty breezes, while the 3rd flr space-w/its own rooftop deck &hot tub hookup-provides a tucked-away haven for relaxation or play.The luxe primary suite is a sanctuary in itself, featuring a cozy gas fireplace, spa bath & floor-to-ceiling water views. A flexible 1st flr BR doubles as a home office, while the oversized 3+ car garage ensures ample storage for all your beach essentials.The Guest Cottage (318)adds over 832 sq ft of living space w/2 BRs & 1 full bath-perfect for guests, extended family/inlaws, or as a lucrative rental. Currently rented month-to-month, this charming cottage has a strong rental history &consistent demand. Set on .27 acres w/privacy, the property includes a maintained dock w/direct access toPine Creek & LI Sound. 3961 sqft is total for both 318&320

5 Beds ⋅ 5 Baths ⋅ 24111168 MLS

Welcome to a truly exceptional opportunity-a direct waterfront compound offering expansive views of Long Island Sound, a dock, &endless showstopping sunsets. This remarkable property features 2 residences: a fully renovated, FEMA-compliant main house AND a charming, income-generating guest cottage.The Main Residence (320)is a modern coastal retreat offering 3,129 sq ft of sun-drenched living space, gourmet kitchen, 3/4 bedrooms &4 full baths. Renovated to perfection in 2018, this light-filled home is a celebration of indoor-outdoor living, w/expansive windows framing unobstructed water views &an open floor plan ideal for entertaining. The wraparound private deck offers front-row seating to endless sunsets &salty breezes, while the 3rd flr space-w/its own rooftop deck &hot tub hookup-provides a tucked-away haven for relaxation or play.The luxe primary suite is a sanctuary in itself, featuring a cozy gas fireplace, spa bath & floor-to-ceiling water views. A flexible 1st flr BR doubles as a home office, while the oversized 3+ car garage ensures ample storage for all your beach essentials.The Guest Cottage (318)adds over 832 sq ft of living space w/2 BRs & 1 full bath-perfect for guests, extended family/inlaws, or as a lucrative rental. Currently rented month-to-month, this charming cottage has a strong rental history &consistent demand. Set on .27 acres w/privacy, the property includes a maintained dock w/direct access toPine Creek & LI Sound. 3961 sqft is total for both 318&320

318 320 Pine Creek Ave, Fairfield

$3,205,000

144 Westway Road is that once-in-a-lifetime opportunity to be a part of the desirable lifestyle that is found in Southport Village. Located on Westway Road, this home is surrounded by historic homes dating back to era of a bustling shipping harbor providing a classic New England setting. This home has been signficantly renovated over the years creating living spaces that are optimal for todays buyers; new open-concept kitchen/family room with top-of-the-line appliances, finishes, fireplace and extensive built-ins, new master bedroom addition complete with walk-in closet and spacious bath, and much more. ALL 5 bedrooms are en-suite with newly renovated bathrooms. Outdoor space creates a beautiful oasis with mature landscaping, privacy trees and an expansive tiered bluestone patio. This convenient location is steps to Southport Harbor, walk-to train, and local shops. Don't miss this opportunity to be a part of life in the "Village".

5 Beds ⋅ 6 Baths ⋅ 24149388 MLS

144 Westway Road is that once-in-a-lifetime opportunity to be a part of the desirable lifestyle that is found in Southport Village. Located on Westway Road, this home is surrounded by historic homes dating back to era of a bustling shipping harbor providing a classic New England setting. This home has been signficantly renovated over the years creating living spaces that are optimal for todays buyers; new open-concept kitchen/family room with top-of-the-line appliances, finishes, fireplace and extensive built-ins, new master bedroom addition complete with walk-in closet and spacious bath, and much more. ALL 5 bedrooms are en-suite with newly renovated bathrooms. Outdoor space creates a beautiful oasis with mature landscaping, privacy trees and an expansive tiered bluestone patio. This convenient location is steps to Southport Harbor, walk-to train, and local shops. Don't miss this opportunity to be a part of life in the "Village".

144 Westway Rd, Fairfield

$3,200,000

BUILDING OPPORTUNITY ATOP SASCO HILL - This stunning 2-acre parcel atop Sasco Hill, the pinnacle, presents a unique opportunity to build a sensational estate while enjoying captivating views of Southport Harbor and the Norwalk Islands. The exceptional Sasco Hill Road location provides not only privacy but also an extraordinary canvas for a luxurious custom residence, characterized by expansive lawns, and southern vistas of Long Island Sound; all within walking distance of Sasco Beach. Adding character and a touch of history to this remarkable site, the property features a historic stone foundation of an early Onion Barn. And, the surrounding amenities of charming Southport Village and vibrant Fairfield Center are just minutes away, ensuring convenience to Metro North Train Service, and access to great dining, shopping, and cultural experiences. Transform this idyllic setting into your personal sanctuary in one of Fairfield County's most beautiful locations. NEW TAX ASSESSMENT IS $2,123,730. ANY AND ALL STRUCTURES BEING SOLD IN "AS IS" CONDITION.

24169366 MLS

BUILDING OPPORTUNITY ATOP SASCO HILL - This stunning 2-acre parcel atop Sasco Hill, the pinnacle, presents a unique opportunity to build a sensational estate while enjoying captivating views of Southport Harbor and the Norwalk Islands. The exceptional Sasco Hill Road location provides not only privacy but also an extraordinary canvas for a luxurious custom residence, characterized by expansive lawns, and southern vistas of Long Island Sound; all within walking distance of Sasco Beach. Adding character and a touch of history to this remarkable site, the property features a historic stone foundation of an early Onion Barn. And, the surrounding amenities of charming Southport Village and vibrant Fairfield Center are just minutes away, ensuring convenience to Metro North Train Service, and access to great dining, shopping, and cultural experiences. Transform this idyllic setting into your personal sanctuary in one of Fairfield County's most beautiful locations. NEW TAX ASSESSMENT IS $2,123,730. ANY AND ALL STRUCTURES BEING SOLD IN "AS IS" CONDITION.

817 Sasco Hill Rd, Fairfield

$3,150,000

Ideally located in one of Fairfield's most desirable beach neighborhoods, this beautiful custom-built FEMA compliant home combines premium construction and efficiency with high-end finishes throughout. Unique features include 2x6 framing, steel beam support, energy efficient foam insulation, dual HVAC and tankless hot water systems, a gorgeous custom kitchen with Thermador appliances and honed granite countertops, an incredible home theater system, a 3-floor elevator, a spacious bonus room with views of Long Island Sound, an oversized garage with a gym or if you prefer, space for a 3rd car; and to top it all off, a saltwater swim spa overlooking a lush, professionally landscaped yard. Just steps to deeded beach access, and minutes to the playground, tennis and bocce courts, Fairfield's vibrant town center and Metro North train station. This stunning home isn't going to last - schedule your showing before it's gone.

4 Beds ⋅ 4 Baths ⋅ 24196292 MLS

Ideally located in one of Fairfield's most desirable beach neighborhoods, this beautiful custom-built FEMA compliant home combines premium construction and efficiency with high-end finishes throughout. Unique features include 2x6 framing, steel beam support, energy efficient foam insulation, dual HVAC and tankless hot water systems, a gorgeous custom kitchen with Thermador appliances and honed granite countertops, an incredible home theater system, a 3-floor elevator, a spacious bonus room with views of Long Island Sound, an oversized garage with a gym or if you prefer, space for a 3rd car; and to top it all off, a saltwater swim spa overlooking a lush, professionally landscaped yard. Just steps to deeded beach access, and minutes to the playground, tennis and bocce courts, Fairfield's vibrant town center and Metro North train station. This stunning home isn't going to last - schedule your showing before it's gone.

679 Rowland Rd, Fairfield

$3,100,000

Waterfront summer living! This slice of heaven features 2-3 bedrooms, 2.5 bathrooms, and a detached studio apartment with a full bath. This modern architectural masterpiece, designed by award winning architect, Roger Ferris, has breathtaking views and an abundance of natural light, courtesy of the expansive floor to ceiling windows in every room. The dreamy primary bedroom has panoramic water views with the Manhattan skyline in the distance. The second bedroom contains a loft which provides two separate, private sleeping nooks and a lounge area with two-story, floor to ceiling windows. The detached studio apartment makes an ideal option for guests or extra recreational space with a wet bar and loft. The spacious exterior offers ample yard and deck space directly on the water for abundant outdoor living opportunities. Walk to the sandy beach from your yard at low tide or stroll down your sleepy street to the beach access path. This unique home's private, tranquil, waterfront setting makes it hard to believe it is so close to town, Metro North, and 95 for easy commuting, shopping, and dining in beautiful Fairfield.

2 Beds ⋅ 3 Baths ⋅ 24147983 MLS

Waterfront summer living! This slice of heaven features 2-3 bedrooms, 2.5 bathrooms, and a detached studio apartment with a full bath. This modern architectural masterpiece, designed by award winning architect, Roger Ferris, has breathtaking views and an abundance of natural light, courtesy of the expansive floor to ceiling windows in every room. The dreamy primary bedroom has panoramic water views with the Manhattan skyline in the distance. The second bedroom contains a loft which provides two separate, private sleeping nooks and a lounge area with two-story, floor to ceiling windows. The detached studio apartment makes an ideal option for guests or extra recreational space with a wet bar and loft. The spacious exterior offers ample yard and deck space directly on the water for abundant outdoor living opportunities. Walk to the sandy beach from your yard at low tide or stroll down your sleepy street to the beach access path. This unique home's private, tranquil, waterfront setting makes it hard to believe it is so close to town, Metro North, and 95 for easy commuting, shopping, and dining in beautiful Fairfield.

274 Pine Creek Ave, Fairfield

$3,100,000

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family compound and abutting the Greenfield Hill Historic District, the setting offers both distinction and privacy. This historic home has been thoughtfully expanded, restored, and renovated over the years, blending irreplaceable old world craftsmanship with modern comfort. High ceilings, wide plank floors, intricate moldings, arched entries, and abundant natural light create a refined yet inviting atmosphere. Notable spaces include a cherry library, formal dining room, gracious family and living rooms anchored by two brick chimneys and five fireplaces, an expansive kitchen, and elegant entertaining areas throughout. Outdoors, enjoy a bluestone patio with pergola, ideal for al fresco dining and relaxed gatherings. Adding to the property's uniqueness is a recently rebuilt pool house featuring a kitchenette, family room, recreation room, art studio, home office, and 1.5 baths. The romantic keyhole shaped gunite pool is framed by stone walls and lush gardens, creating a private retreat.

5 Beds ⋅ 7 Baths ⋅ 24158967 MLS

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family compound and abutting the Greenfield Hill Historic District, the setting offers both distinction and privacy. This historic home has been thoughtfully expanded, restored, and renovated over the years, blending irreplaceable old world craftsmanship with modern comfort. High ceilings, wide plank floors, intricate moldings, arched entries, and abundant natural light create a refined yet inviting atmosphere. Notable spaces include a cherry library, formal dining room, gracious family and living rooms anchored by two brick chimneys and five fireplaces, an expansive kitchen, and elegant entertaining areas throughout. Outdoors, enjoy a bluestone patio with pergola, ideal for al fresco dining and relaxed gatherings. Adding to the property's uniqueness is a recently rebuilt pool house featuring a kitchenette, family room, recreation room, art studio, home office, and 1.5 baths. The romantic keyhole shaped gunite pool is framed by stone walls and lush gardens, creating a private retreat.

2683 Bronson Rd, Fairfield

$3,100,000

New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal charm with modern luxury, just a short walk to Penfield Beach, Fairfield Beach Club, vibrant downtown, train, & top rated schools. With 5 bedrooms, 4.5 baths, and 3 finished levels, this elevator ready home offers exceptional design, flow, and comfort. The open concept custom kitchen is both functional and beautiful with top of the line appliances, custom cabinetry, walk in pantry and Quartz countertops. The dining area has sliders to a spacious deck while the living room is the perfect space for entertaining or quiet night in. A butler's pantry with wet bar and second dishwasher leads to a sun filled flex room with fireplace, ideal for movie night or entertaining. Upstairs, the serene primary suite includes a spa-like bath with soaking tub, heated floors, two walk-in closets, and a Juliet balcony, perfect for taking in the breeze and the gentle sounds of nature. Two additional bedrooms enjoy private en-suite baths. The third floor offers 2 more bedrooms, a full bath, and a bonus space perfect for guests, an office, or a playroom. Enjoy quiet mornings on the covered third floor deck. Outside, enjoy a spacious yard with room for a pool or garden. The covered Le Nai is designed for year-round use-great for entertaining, lounging, or a home gym. A 2 car garage with tandem space offers ample parking. From beach walks to downtown dinners, this isn't just a home...it's a lifestyle!

5 Beds ⋅ 5 Baths ⋅ 24132638 MLS

New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal charm with modern luxury, just a short walk to Penfield Beach, Fairfield Beach Club, vibrant downtown, train, & top rated schools. With 5 bedrooms, 4.5 baths, and 3 finished levels, this elevator ready home offers exceptional design, flow, and comfort. The open concept custom kitchen is both functional and beautiful with top of the line appliances, custom cabinetry, walk in pantry and Quartz countertops. The dining area has sliders to a spacious deck while the living room is the perfect space for entertaining or quiet night in. A butler's pantry with wet bar and second dishwasher leads to a sun filled flex room with fireplace, ideal for movie night or entertaining. Upstairs, the serene primary suite includes a spa-like bath with soaking tub, heated floors, two walk-in closets, and a Juliet balcony, perfect for taking in the breeze and the gentle sounds of nature. Two additional bedrooms enjoy private en-suite baths. The third floor offers 2 more bedrooms, a full bath, and a bonus space perfect for guests, an office, or a playroom. Enjoy quiet mornings on the covered third floor deck. Outside, enjoy a spacious yard with room for a pool or garden. The covered Le Nai is designed for year-round use-great for entertaining, lounging, or a home gym. A 2 car garage with tandem space offers ample parking. From beach walks to downtown dinners, this isn't just a home...it's a lifestyle!

450 Penfield Rd, Fairfield

$3,050,000

Direct waterfront on premier Fairfield Beach with rare sandy frontage and sweeping, panoramic coastline views of the Long Island Sound. This sophisticated 3278sqft 4-bedroom residence offers an exceptional combination of elevation, privacy, and protection by two jetties. Extensively improved with over $400K in recent upgrades, the home is engineered for low-maintenance coastal luxury, featuring high-end Marvin coastal-grade windows and doors complemented by automated Alutech storm shutters [seamless protection at the touch of a button], while the property's low-maintenance composite decking and engineered protective berm ensure both superior flood resilience and effortless upkeep. Inside, the sun-filled open floor plan flows from a one-of-a-kind custom wood kitchen into dining and living areas, leading out to the expansive deck and a private path to the sand. Architectural highlights include 9ft+ ceilings, walls of glass, and a dramatic staircase. The primary wing is a private retreat with breathtaking water views, a personal balcony, and an updated bath. The floor plan includes a versatile upper-level suite that features wall-to-wall water views and a convenient half-bath-ideal for a guest wing, executive office, or fitness studio. A whole-house backup battery, smart home lighting, and a 1-car garage with parking for 8+ cars round out this rare offering. Enjoy the perfect blend of coastal technology and in-town convenience, just moments from the train and town center.

4 Beds ⋅ 4 Baths ⋅ 24151538 MLS

Direct waterfront on premier Fairfield Beach with rare sandy frontage and sweeping, panoramic coastline views of the Long Island Sound. This sophisticated 3278sqft 4-bedroom residence offers an exceptional combination of elevation, privacy, and protection by two jetties. Extensively improved with over $400K in recent upgrades, the home is engineered for low-maintenance coastal luxury, featuring high-end Marvin coastal-grade windows and doors complemented by automated Alutech storm shutters [seamless protection at the touch of a button], while the property's low-maintenance composite decking and engineered protective berm ensure both superior flood resilience and effortless upkeep. Inside, the sun-filled open floor plan flows from a one-of-a-kind custom wood kitchen into dining and living areas, leading out to the expansive deck and a private path to the sand. Architectural highlights include 9ft+ ceilings, walls of glass, and a dramatic staircase. The primary wing is a private retreat with breathtaking water views, a personal balcony, and an updated bath. The floor plan includes a versatile upper-level suite that features wall-to-wall water views and a convenient half-bath-ideal for a guest wing, executive office, or fitness studio. A whole-house backup battery, smart home lighting, and a 1-car garage with parking for 8+ cars round out this rare offering. Enjoy the perfect blend of coastal technology and in-town convenience, just moments from the train and town center.

1053 Fairfield Beach Rd, Fairfield

$3,015,000

Rare Beach Property~ Steps to Sandcastle Playground, Jennings Beach and South Benson Marina - this striking Colonial delivers a unique blend of luxurious beach living and exceptional build quality. Homes of this caliber seldom become available along the shoreline. ~ EXPANSIVE FIRST FLOOR ~ The house features a sprawling first floor Great Room and show stopping Chef's Kitchen which combine in a seamless open layout. The space is anchored by an oversized Carrara marble island, Thermador appliances and a built-in sound system. Light pours in through custom plantation shutters adding to the home's sophisticated and refined coastal aesthetic. ~ PRIVATE RETREATS ~ Upstairs, soaring ceilings and custom millwork adorn a sun-drenched Primary Suite featuring floor-to-ceiling windows and a spacious private balcony, offering a front row seat to epic sunrises and summer fireworks. Four additional bedrooms include two generous en-suites. The fully finished, expansive third level features three private nooks ideal for additional office space or cozy play areas. The third floor bedroom retreat is perfect for in-laws or an au pair and features its own panoramic balcony. ~ OUTDOOR OASIS ~ Lush plantings and mature greenery compliment an expansive bluestone patio and fully fenced yard to create a secluded backyard sanctuary. A UNIQUE OPPORTUNITY to own luxury, craftmanship and privacy at the beach.

6 Beds ⋅ 6 Baths ⋅ 24154688 MLS

Rare Beach Property~ Steps to Sandcastle Playground, Jennings Beach and South Benson Marina - this striking Colonial delivers a unique blend of luxurious beach living and exceptional build quality. Homes of this caliber seldom become available along the shoreline. ~ EXPANSIVE FIRST FLOOR ~ The house features a sprawling first floor Great Room and show stopping Chef's Kitchen which combine in a seamless open layout. The space is anchored by an oversized Carrara marble island, Thermador appliances and a built-in sound system. Light pours in through custom plantation shutters adding to the home's sophisticated and refined coastal aesthetic. ~ PRIVATE RETREATS ~ Upstairs, soaring ceilings and custom millwork adorn a sun-drenched Primary Suite featuring floor-to-ceiling windows and a spacious private balcony, offering a front row seat to epic sunrises and summer fireworks. Four additional bedrooms include two generous en-suites. The fully finished, expansive third level features three private nooks ideal for additional office space or cozy play areas. The third floor bedroom retreat is perfect for in-laws or an au pair and features its own panoramic balcony. ~ OUTDOOR OASIS ~ Lush plantings and mature greenery compliment an expansive bluestone patio and fully fenced yard to create a secluded backyard sanctuary. A UNIQUE OPPORTUNITY to own luxury, craftmanship and privacy at the beach.

598 S Benson Rd, Fairfield