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$3,800,000
5 Beds ⋅ 8 Baths ⋅ 24115614 MLS
Southport Custom Shingle-Style Colonial Designed by renowned architect Jack Franzen, this exquisite six-bedroom, Energy Star-rated home offers timeless design and exceptional efficiency, including geothermal heating and cooling. Privately sited on 2.48 acres of beautifully manicured, level property in a coveted Southport neighborhood, the residence blends classic architecture with modern luxury. Inside, finely crafted details abound-hardwood floors, imported marbles, and custom cabinetry set the tone. Elegant living and entertaining spaces include a formal living room with fireplace, a cozy den/office with fireplace, and a generous family room with yet another fireplace. Numerous French doors open to a sweeping covered porch, inviting effortless indoor-outdoor living. Step outside to enjoy resort-style amenities: a saltwater pool, fire pit, professional-grade, lit tennis court, and expansive patios perfect for gathering and relaxing. This exceptional property offers both convenience and privacy-a rare and refined retreat in the heart of Southport.

1241 Hulls Hwy, Fairfield
$3,800,000
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
$3,755,000
4 Beds ⋅ 6 Baths ⋅ 24030156 MLS
A rare opportunity to experience luxurious living in one of Connecticut's most coveted neighborhoods: Southport Harbor. This extraordinary, custom, 5 bed, 5.5 bath Nantucket shingle & stone home features exceptional living spaces & timeless sophistication throughout. The elegant decor melds impeccable craftsmanship, modern design & high-quality construction features. Every detail has been meticulously planned & curated, from the newer white oak flooring, to the exquisite designer lighting that adds elegance & ambiance to each room, to the marble and tile selections, to the custom built-ins and millwork, to the hi-tech features. From the moment you step inside, you are captivated by the home's beauty. The gourmet kitchen features custom cabinetry, high-end appliances, an oversized Calcutta marble island, vaulted and paneled ceiling, and a breakfast area. The kitchen opens to the family room with another stunning vaulted ceiling, fireplace with marble surround and French doors to the back patio. The dining room boasts a sultry wet bar, and French doors to the courtyard & impressive backyard oasis.The outdoor entertaining spaces feature a saltwater gunite pool with waterfall, auto safety cover, year-round spa, large stone fireplace, several patios, pizza oven, built-in BBQ, pergola, life-sized chess/checkers, raised gardens & separate grass play areas. The home is geothermal & solar powered, for substantial utility cost savings. Walk to Southport Beach, Harbor, Equinox and Train

184 S Gate Ln, Fairfield
$3,750,000
6 Beds ⋅ 6 Baths ⋅ 170617302 MLS
SOUTHPORT CHIC - This home is rented until June 2025. Just steps to the beach, Harbor and quaint Southport Village, this French inspired beauty will make you feel like you've been whisked away to the European countryside although you're just 50 minutes from Manhattan. In the neighborhood of multi-million dollar seaside estates, restored antique homes, and newer builds with that Je ne sais quoi quintessential New England charm, this French Provincial prize is perfectly private, buffered from the road on a picturesque 2.79 acres with magnificent heated pool. Timeless and sophisticated, boasting 5200sf, the large and inviting public rooms with French doors unite the indoors with outside patios and entertaining spaces. You'll adore the high ceilings, elegance, and easy lifestyle in the comfortable sun-drenched spaces: living room with fireplace; oversized dining room; kitchen with large island and breakfast area opening to the family room with fireplace; library with fireplace and bar; office; laundry, and mudroom. There is a luxurious guest suite on the main floor along with a smaller bedroom with full bath. Come upstairs to the gracious primary suite with fireplace, balcony overlooking the pool, walk-in closet and marble bath. Three additional bedrooms and two full baths complete the 2nd and 3rd floor. C'est Magnifique!

987 Pequot Ave, Fairfield
$3,750,000
5 Beds ⋅ 24071961 MLS
Fantastic waterfront home with separate guest house located on the coveted FAIRFIELD BEACH (near Penfield Beach) - with 5500 SF of living space, 6 car garage and 70 feet of beach frontage with panoramic views of Long Island Sound & Penfield Lighthouse. Main house boasts tons of windows & sliding french doors that provide sunlight & ocean breezes. The main level has an open floor plan w/wrap around covered porch (and just a few steps to oversized patio), living room w/gas fireplace, dining area, breakfast area, eat in kitchen, walk in pantry, powder room, mudroom, laundry room & two car garage. The rear staircase brings you to the 500SF family room w/soaring ceiling. The primary suite has luxurious spa-like bathroom, spacious walk in closet, office/sitting room & sliders to covered porch. This level also includes an ensuite bedroom w/sliders to covered porch, two additional bedrooms & hall bath. The finished walk up 3rd floor is unheated and serves as an incredible playroom with tons of storage and a peacefully located inset balcony overlooking the beach & water. The second building on property has an additional four car garage with a nearly 1000SF, 4 room, 2 bedroom, 1 bath apartment perfect for AuPair, In-Law or rental income potential. Add'l characteristics include exterior access only bathroom with shower for beach guests, solar panels, two level 2 EV chargers, whole house gas generator, security system, vinyl shingle siding & trim. Best deal in the Fairfield Beach area.

531 Fairfield Beach Rd, Fairfield
$3,750,000
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
$3,749,000
5 Beds ⋅ 4 Baths ⋅ 24054301 MLS
Experience luxury living on Connecticut's Gold Coast with this pristine, custom home with a gunite pool and spa on a prime cul-de-sac in Southport Harbor - located a few homes from Southport Beach and a short stroll to the Harbor, Village & Equinox. Completely rebuilt in 2017, 97 Southgate Lane is sited on a level and dry, almost full acre parcel, and is NOT located in a flood zone. This 5-bedroom, 3.5 bath home blends charm and modernity with extensive moldings, hardwood floors, high ceilings, gorgeous baths, luxury lighting, and an abundance of natural light throughout. Highlights include a first-floor guest suite, study with built-ins, charming front & back covered porches, a spectacular primary suite, 3 wood burning fireplaces and an open floor plan. The front to back gourmet kitchen with vaulted ceiling boasts custom cabinetry, high-end appliances, two large honed marble islands, heated floors, beautiful lighting, a walk-in pantry, and a built-in dining area. The primary suite is a sumptuous retreat with a coffered ceiling, expansive walk-in custom closet, spa bathroom and large balcony. The manicured, professionally landscaped, property, with irrigation, provides year-round beauty. Additional features include an oversized, attached 2 car garage, low/no maintenance Hardie Board siding and Azek trim, a mudroom with custom built-ins and separate entrance, and a second floor laundry room. Natural gas and city water. This is Southport living at its finest!

97 S Gate Ln, Fairfield
$3,700,000
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
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
$3,700,000
5 Beds ⋅ 5 Baths ⋅ 24071014 MLS
Experience unparalleled luxury in this exquisite coastal residence, just moments from the expansive sands of Penfield Beach and the tranquil waters of Long Island Sound. This architectural masterpiece comprises 3 floors of meticulously designed living space, ensuring a lifestyle of sophistication and comfort. Enjoy year round invigorating sea breezes from any one of the 5 decks. Stunning kitchen, with custom cabinetry, premium Wolf/Sub Zero appliances and massive center island, flows seamlessly into the family room for informal gatherings. Entertain in style with the gracious formal living room and dining room, anchored by a fabulous see-through fireplace. The primary bedroom suite is an opulent sanctuary, boasting a custom walk in closet and a spa-like bathroom with free-standing tub and steam shower. 4 additional bedrooms, including a private guest wing with full bath, provide ample space for friends and family. Versatile third floor has rec/playroom, gym space, bedroom/bathroom and 2 covered decks. The professionally landscaped yard is a private oasis with mature hydrangeas, shrubs, and apple bearing espalier trees. Indulge in endless summer fun in the newer heated POOL! Ample under house storage for kayaks and paddleboards. Walk to train and all the vibrant downtown boutiques and restaurants. This high tech, energy efficient home combines serene design with modern amenities so you can fully embrace the coastal lifestyle and live life like you're on vacation every day!

612 Penfield Rd, Fairfield
$3,700,000
4 Beds ⋅ 3 Baths ⋅ 24059174 MLS
207 Main Street exemplifies the quintessential Southport village home. This 1804 historic home has been renovated and redesigned by the owner, who owns McGrath II, a Manhattan based decorating firm. Exuding Charm while keeping with its architectural integrity this home is Village living at its best. Here is an opportunity to live in a water community enjoying all it offers just steps away from Southport Harbor, Pequot Yacht Club and Perry Green.

207 Main St, Fairfield
$3,600,000
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
$3,569,500
4 Beds ⋅ 6 Baths ⋅ 24010642 MLS
Superior in architecture and design, "Meadow View" in sought after Southport is a masterpiece of unrivaled quality that flows effortlessly from the 4 floors of contemporary and sophisticated interior space to the extraordinary oasis that awaits outside with exquisite acreage, pool, elevated 8-person spa, entertaining patios, picturesque stonewalls & split rail fencing, and recreation area. Proudly built to exceed expectation, this 8,902sf rare beauty with home theater, safe room, and commercial grade gym, overlooks neighboring meadow property offering utter peace & serenity while just minutes to darling boutiques, gourmet shops, and top restaurants in Southport, Greenfield Hill, & Fairfield. Beaches, train, and nationally acclaimed schools are all here too. Down a meandering driveway, lighted stone pillars and expensive bluestone covered front porch welcome you to experience life how it should be. Get ready for a jaw dropping "HELLO" moment when you enter into the gracious front-to-back entryway with a wall of French doors, dramatic staircase, and soaring ceiling. Throughout this home, the generously proportioned rooms with high ceilings are naturally filled with sunlight and offer splendid views at every turn. Additional highlights include: large Guest Suite/2nd Primary bedroom; fabulous finished 3rd floor with full bath & window seats; luxury fixtures, appliances, control 4 system; 3 car garage; generator; many recent upgrades & improvements.

471 Hulls Farm Rd, Fairfield
$3,525,000
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
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
$3,500,000
5 Beds ⋅ 6 Baths ⋅ 170623012 MLS
INTRODUCING A TRULY REMARKABLE PROPERTY - the fabulous in-town landmark, circa 1850 Samuel A. Nichols House. This magnificent residence spans 4,936 square feet & offers a luxurious & private living experience. With 5 bedrooms & 5 1/2 baths, this home provides ample space for a growing family and entertaining lifestyle. The home has been meticulously maintained and was revamped in 2019-2022 with updated mechanicals, new roof (main house and garage) as well as the exterior painted, new shutters, generator, new patio & drainage, & much more. From the moment you enter, you will be captivated by the exquisite symmetry & spectacular design of this historic home. The property features 10' ceilings, deep crown mouldings, double front doors with beveled glass & an elegant main staircase. Formerly the home of celebrated artist Robert Vickery, this property holds a special place in Fairfield's history. The main floor consists of a Living Room, Dining Room, Family Room - each adorned with a fireplace, adding warmth and charm to the living spaces; a cherry-paneled Library provides a serene and sophisticated retreat for working or a quiet place to read. The stunning Kitchen is a true masterpiece, complete with porcelain countertops, center island, hardwood floors, double wall ovens, radiant floor heat, double dishwashers, extra fridge drawers, Viking 6 burner stove, butler's pantry & a walk-in pantry. The Breakfast Nook offers a delightful space to start your day, bathed in natural light.

931 Old Post Rd, Fairfield
$3,500,000
4 Beds ⋅ 5 Baths ⋅ 24106604 MLS
Tucked behind a long private drive in the heart of Southport Village, "The Cottage" is a rare and enchanting coastal retreat that captures the serenity of another time. Built c1919 by architect William S. Sloan as his personal home-Sloan was a decorated WWI veteran and grandson of DL&W Railroad president and Citibank founder Sam Sloan-this timeless haven blends heritage with ease. Set on 2.35 park-like acres just steps from the beach, it offers a quiet elegance with a wraparound screened porch made for morning coffee and evening conversations. Inside, sunlit rooms, a first-floor primary suite, and original architectural details echo the home's soulful past, while updated interiors provide comfort for modern living. A place to gather, breathe, and reconnect-with nature, loved ones, and life's simpler rhythms. Outside, enjoy a tranquil pool, tennis court, enclosed vegetable garden, and even a peach tree. A charming guest cottage invites extended stays or private escapes. Walk to Southport Beach, the train, and the village. This is coastal living with history, heart, and soul.

1226 Pequot Ave, Fairfield
$3,495,000
5 Beds ⋅ 8 Baths ⋅ 24070965 MLS
Welcome home to a breathtaking estate where timeless elegance meets modern luxury. Set on over 3 acres of park-like grounds in coveted lower Greenfield Hill, this extraordinary Colonial is a masterpiece of design offering an open-concept layout, soaring 10 ft ceilings & oversized 6 ft windows throughout; flooding the home w/natural light & capturing spectacular southwesterly views. The chef's kitchen is an entertainers dream w/custom cabinetry, 11 ft island, butlers pantry, walk-in pantry & breakfast room w/ French Doors to deck. Grand family room w/wood burning fireplace & coffered ceiling. Formal dining room stuns w/8 ft. glass doors for wine storage. Gorgeous home office w/custom built-ins & gas fireplace. Upstairs, a sublime master suite w/lit tray ceiling, gas fireplace, extraordinary custom outfitted his & hers walk-in closets, luxurious marble bathroom & breakfast bar w/refrigerator & sink. Add'l 4 large bedrooms all w/walk in closets. Au pair/in law suite w/separate back staircase entrance. Exquisite 2 story mudroom w/custom built-ins & add'l 1st fl powder room. 2000 sq ft. finished walk-out lower level w/gym, 2 add'l bathrooms, kitchen, wood burning fireplace, storage & safe room. Add'l features include: irrigation, new stone wall, fence & automatic front gate, 5'' white oak floors throughout, designer light fixtures, 3-car heated/AC garage w/14' ceilings, CAT 6 wired throughout, gas heat, solar panels, deer fenced. Approx. $500k in improvements by current owner.

735 Redding Rd, Fairfield
$3,337,500
5 Beds ⋅ 5 Baths ⋅ 24082317 MLS
This sophisticated and modern beach home offers breathtaking water views and luxurious amenities just steps from the shore. Designed for ultimate comfort and style, this approximately 4,500 sq. ft. residence features an open floor plan, five spacious bedrooms, four and a half baths, and four fireplaces. An elevator provides seamless access to all four levels, while multiple balconies, a newly screened-in covered porch, and expansive rooftop decks create the perfect setting for indoor-outdoor living. The first floor includes a private office and two additional bonus rooms, ideal for work or leisure. Crafted with the finest materials and exceptional attention to detail, no expense has been spared. The beautifully landscaped property boasts an irrigation system, a patio with an outdoor fireplace, and space for a pool. This home is built for efficiency and convenience, featuring underground utilities, AZEK trim, full-house spray foam insulation, a four-zone high-efficiency HVAC system, audio system, and an automatic-start whole-house Generac gas generator. Additional enhancements include Air Bear filters, a whole-house recirculating system, and two humidifiers on the furnaces. This is coastal luxury at its finest.

411 Birch Rd, Fairfield
$3,300,000
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
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
$3,290,000
4 Beds ⋅ 4 Baths ⋅ 24065195 MLS
Charming English Cottage located on desirable Pequot Avenue steps from Southport Beach. Private courtyard is the centerpiece of the home with patio and flower beds throughout. First floor primary complete with walk-in closet and updated bath. 3 additional bedrooms, all ensuite. Private property set back from the road with gated pool and waterfall.

1128 Pequot Ave, Fairfield
$3,250,000
4 Beds ⋅ 4 Baths ⋅ 24021785 MLS
PREMIER LOWER GREENFIELD HILL LOCATION PLUS PREMIER NEW CUSTOM BUILT HOME, Welcome to 100 Mine Hill Road. Sited on 2 park-like acres w/ gorgeous plantings & stone masonry. Once inside you will immediately be impressed as no expense was spared w/ over the top high end finishes in all 13 rooms. Presenting an open floor plan w/ soaring ceilings & 3 levels of meticulously crafted living space designed for ultimate comfort & style. 1st & 2nd-floor primary suite ensures flexibility for modern living. Designed for maximum energy efficiency & comfort featuring European triple-pane tilt-turn windows & doors by KLAR Studio in Westport. 2 ERV fresh air exchange systems ensure continuous circulation of filtered & tempered fresh air. Every detail has been carefully considered, from the custom cabinetry by JEM Woodworking in Greenwich, to the solid brass hardware handmade in England by Armac Martin. Prime grade European white oak floors & high-efficiency LED lighting grace each room, creating an ambiance of sophistication & warmth. Experience unparalleled control w/ a Lutron Radio RA 3 lighting & shading automation system, complemented by the Josh home voice control automation system. Your security & peace of mind are assured w/ Lorex 4K night vision security cameras & a Generac whole home generator. Ethernet wiring, high-end appliances, spray foam insulation & 1 &1/8" subfloors. Ideally located close to town, train, parks, dining & shopping. This luxurious estate is truly a standout!

100 Mine Hill Rd, Fairfield
$3,250,000
3 Beds ⋅ 4 Baths ⋅ 170620925 MLS
Located on historic Harbor Road, this sleek and elegant home offers the best of both Manhattan and Southport Village lifestyles. Completed in 2000, it provides three floors of living space with an elevator, a rare find in Southport. The property also features a coveted two-car attached garage. The current owners have meticulously upgraded the home with fresh interior paint, new wallpaper, refinished hardwood floors, an improved elevator system, updated lighting, a new wet bar, a luxurious primary bathroom with radiant floor heating, a new kitchen banquette, a Ring alarm system, extensive landscaping with an irrigation system, and Wi-Fi enabled thermostats accessible via your phone. Enjoy captivating water views of Southport Harbor and the Long Island Sound from numerous rooms in this exceptional property. The expansive bluestone terrace, accessible from the kitchen or sunroom, offers delightful outdoor entertainment spaces that evolve with the seasons due to carefully orchestrated landscaping. This property provides the feeling of living in upscale urban areas like Georgetown or the Upper East Side while offering the tranquility of suburban waterfront living. 240 Harbor Road perfectly blends suburban serenity with easy access to the town, train, and restaurants. It's just an hour away from NYC but feels like a world apart in beautiful Coastal Connecticut.

240 Harbor Rd, Fairfield
$3,225,000
5 Beds ⋅ 5 Baths ⋅ 170567598 MLS
Upon its completion in the Summer of 1869, 658 Pequot Avenue was described in the Southport Chronicle as “an ornament to the street”. Patterned in the Second Empire style, this stately Victorian welcomes visitors with a raised front porch that runs the full width of the home. Arched, oversized double doors open to a soaring center hall with 12-foot ceilings and a grand, quarter-turn staircase. 12-foot ceilings continue through the Living Room, Dining Room, En-Suite Guest Bedroom and relocated Eat-In Kitchen. Every level of the home’s interior was completely reimagined & renovated in 2022, blending its rich history with today’s design aesthetic & a modern family’s needs. The Second floor presents a Primary Bedroom Suite with Full Bath and a substantial Dressing Room, all facing South with the breathtaking view of the Trinity Church steeple. Three large guest bedrooms are spread nicely throughout the rest of the Second Floor offer wonderful natural light & privacy. The Third Floor takes full advantage of the home’s significant proportions creating a 1,500+ square feet room with vaulted ceilings that rivals any modern barn. All of this sits on a level, professionally landscaped half acre with in-ground pool in the heart of historic Southport Village.

658 Pequot Ave, Fairfield
$3,210,000
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
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
$3,150,000
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
$3,125,000
5 Beds ⋅ 5 Baths ⋅ 24117597 MLS
Renovated 5 bedroom, 4.5 bath beach home with large loggia, gunite pool and large rooftop deck off the primary located one block from the beach on prime Lalley Boulevard.

365 Lalley Blvd, Fairfield
$3,100,000
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

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