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1131 Sasco Hill Rd, Fairfield
$25,000,000
6 Beds ⋅ 11 Baths ⋅ 24084663 MLS
Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding drive, revealing a breathtaking landscape of curated gardens, rolling lawns, and panoramic water views. Designed for both grand entertaining and intimate gatherings, the estate features a newly built multi-car garage with a second-floor art studio and play space, a new pool, birch garden, and an expansive patio, all seamlessly integrated with the natural beauty of the surroundings. A private dock with stairs to the secluded beach provides direct waterfront access, while a newly added wine cellar and lower-level suite with a full bathroom enhance the home's luxurious amenities. Recent upgrades, including advanced irrigation, outdoor lighting, new A/V system, ensure modern convenience without compromising the estate's historic charm.Featured in Architectural Digest as "a new house with an old soul," the interiors are a masterclass in refined elegance. Every space is thoughtfully curated with serene color palettes, exquisite craftsmanship, and breathtaking water views from nearly every room. Sasco Point is truly one of America's most distinguished waterfront estates. Luxury Perfected!

1131 Sasco Hill Rd, Fairfield

4800 Congress St, Fairfield
$9,975,000
7 Beds ⋅ 10 Baths ⋅ 24161896 MLS
The former home of Richard Rodgers, composer of The Sound of Music, this 10.92 acre estate with a stunning modern residence was recently fully renovated and expanded, and offers curated one floor living. Generous main rooms are enhanced by lofty ceilings, skylights and walls of glass. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. Separate residential wings include 7 bedrooms and 7 full baths, each with a unique design. All property systems have been upgraded and integrated to work seamlessly .The barn pool house includes a full eat-in kitchen and lounge, bath ,and full gym steps from the pool. An office pavilion is set privately in a quiet garden area. The park like property is surrounded by high stone walls, a nature preserve, open land, a heated paddle tennis court, and an orchard. Live in ultimate style and easy elegance just a quick commute to NYC and airports. This private haven surrounded by a 155 acre nature preserve is minutes to Fairfield, Westport and Greenwich dining and shopping.

4800 Congress St, Fairfield

640 Hulls Farm Rd, Fairfield
$8,696,000
7 Beds ⋅ 8 Baths ⋅ 24160984 MLS
Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 640 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury Homes, Fairfield County's premiere creator of bespoke residential properties, this 8,560SF masterpiece will embody uncompromising craftsmanship, globally sourced materials, and state-of-the-art systems & technology. Expansive floor-to-ceiling glass invites natural light to cascade throughout the meticulously designed interiors, framing serene views of the manicured grounds and resort-style pool w/spa. The open floor plan is ideal for elegant entertaining and effortless daily living. A chef's kitchen of unrivaled distinction is complemented by a fully appointed scullery, seamlessly supporting both private gatherings and large-scale entertaining. The great room exudes warmth and architectural presence, while the handsome parlor/office opens to an oversized covered porch. The primary suite is a sanctuary unto itself, featuring a fireplace, private terrace, and spa-inspired bath designed for true indulgence. 6 addit'l bedrooms provide luxurious accommodations for family & guests alike. LL is exceptional w/media room, golf simulator, gym, etc. 4 car garage, elevator shaft & much more.

640 Hulls Farm Rd, Fairfield

541 Sasco Hill Rd, Fairfield
$6,500,000
5 Beds ⋅ 9 Baths ⋅ 24213955 MLS
Prestigious location. Stately presence. Exceptional living. Introducing a premier 1.25-acre Sasco Hill estate offering extraordinary luxury across 4 levels. This magnificent residence features 5 bedrooms, 9 baths & an uncompromising attention to detail. Outdoors, a private resort awaits with a heated pool & spa, fully equipped outdoor kitchen & expansive terrace overlooking exquisite gardens. An accessory apartment above the garage offers future potential, with plumbing & electrical rough-ins in place. Iron gates flanked by stone lions welcome you to a grand 2-story foyer. The main level showcases exceptional craftsmanship, from the stately living room & Gatsby-inspired formal dining room with garden views to the impressive chef's eat-in kitchen, spacious billiards room, inviting family room & private 1st-floor office. Elegant millwork enhances every room. The 2nd level features 4 luxurious en-suite bedrooms, including 2 primary suites with impressive walk-in closets & dressing rooms. The 3rd level offers flexible living space, including a home gym, bonus room with cedar closet & 5th en-suite bedroom. The finished lower level is an entertainer's dream, complete with an 8-seat home theater, recreation room & storage. Notable upgrades include a new wood roof, Belgian stone & oil-chip driveway, front gates, fencing, updated central air, whole-house generator & finished lower level. Discover extraordinary estate living in Fairfield's prestigious Sasco Hill neighborhood.

541 Sasco Hill Rd, Fairfield

1859 Fairfield Beach Rd, Fairfield
$6,499,000
4 Beds ⋅ 5 Baths ⋅ 24207566 MLS
A rare and extraordinary Long Island Sound waterfront estate, offering over half an acre and nearly 100 feet of direct beach frontage across two parcels (1845 & 1859 Ffld Bch Rd). Set along one of Fairfield's most coveted stretches of shoreline, this exceptional property presents a unique opportunity to create a private coastal compound with an abundance of space, water access, and privacy. The expansive 0.55-acre property features a gracious main residence with an airy second floor offering three bedrooms and a bonus room, along with an additional 748 sq ft on the third floor, creating the potential for sweeping Long Island Sound views. The main residence is complemented by a private in-ground pool and a separate two-car garage. Across the property, a creekside boathouse offers an extraordinary additional dimension, featuring a finished studio apartment, a second two-car garage, and a private dock with creek access. A beautifully manicured, fenced-in grassy lot provides an exceptional sense of privacy and offers generous space for outdoor entertaining, recreation, or exploring future possibilities. With its combination of expansive grounds, direct beach frontage, private dock, pool, two separate two-car garages, and versatile additional living space, this is an exceptionally rare waterfront offering. Buyer to perform their own due diligence with the Town of Fairfield regarding all building, renovation, zoning, and waterfront development possibilities.

1859 Fairfield Beach Rd, Fairfield

98 Banks Pl, Fairfield
$5,995,000
4 Beds ⋅ 6 Baths ⋅ 24216271 MLS
Timeless luxury meets exceptional craftsmanship at 98 Banks Place, where a meticulous restoration & rebuild, completed in 2017, transformed an 1830 Greek Revival into a home offering the comfort of new construction while preserving the soul, warmth, & character only a home of this era can provide. Original floors, brick, timbers, custom windows, reclaimed hardware, & period details blend seamlessly with custom millwork, barrel ceilings, Belgian stone flooring, designer finishes, radiant-heated floors, & all-new systems. A chef's kitchen w/ concealed scullery anchors gracious living spaces, while an inviting family room & serene primary suite balance gathering & retreat. Set on nearly 5.5 private acres, the property is designed for indoor-outdoor living w/ a resort-style pool, year-round spa, expansive bluestone patio, outdoor kitchen, double-sided fireplace, & new pool house offering flexible space for guests, entertaining, an in-law suite, or future living accommodations. Sweeping lawns, formal gardens, an apple orchard, enclosed vegetable garden, & mature green screening create a private retreat unlike any other. Moments from Southport Village, Southport Harbor, Pequot Library, Southport Beach, dining, & the train, this is a rare opportunity to enjoy estate-like living in one of Fairfield County's most sought-after coastal communities, where old-world charm, modern ease, & a walkable coastal lifestyle come together in a truly one-of-a-kind offering.

98 Banks Pl, Fairfield

775 Sasco Hill Rd, Fairfield
$5,995,000
5 Beds ⋅ 7 Baths ⋅ 24175742 MLS
775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully designed floor plan balances grand entertaining with everyday comfort. Formal living and dining rooms, a private library, and a stunning open-concept kitchen seamlessly connect to the expansive family room with vaulted ceilings. Luxurious accommodations include a private guest suite, an elegant primary retreat with dual walk-in closets and a spa-inspired bath, plus additional ensuite bedrooms and a versatile third-floor bonus level ideal for recreation, guests, or a home office. Outdoors, a large stone patio overlooks meticulously landscaped grounds and a spectacular gunite pool, creating a true private oasis. Extensive upgrades throughout the home and property elevate both style and functionality, offering an exceptional lifestyle in one of Fairfield's most coveted locations. Furnishings available for purchase ~ Negotiable.

775 Sasco Hill Rd, Fairfield

590 Sturges Hwy, Fairfield
$5,975,000
6 Beds ⋅ 8 Baths ⋅ 24209002 MLS
For those who believe luxury should never feel predictable. This remarkable Southport estate is a masterful reinvention of new construction...where timeless architecture meets modern artistry, extraordinary craftsmanship, and effortless living. Every element feels intentional, from dramatic windows and beautifully scaled rooms to custom millwork, sophisticated lighting, advanced technology, and finishes chosen for beauty rather than trend. Walls of glass dissolve the boundary between indoors and out, revealing a private, beautifully landscaped setting with a breathtaking pool and cabana...a sanctuary that feels worlds away, yet is moments from everything. 8800 Sqft of unsurpassed quality offering an exceptional floor plan that must be experienced to be appreciated. Chef's will appreciate the exceptional Kitchen, the primary suite is an indulgent retreat, while exceptional entertaining spaces make the home equally suited to intimate evenings and unforgettable gatherings. A completely separate, perfectly renovated guest house with its own address, utilities & garage offers a rare luxury in itself...privacy & possibilities for guests, extended family, office, caretaker or rental income. And the location may be the ultimate luxury: the beauty and charm of Southport, award-winning Fairfield schools, beaches and amenities, and coveted Westport resident privileges including Compo Beach and Longshore. One extraordinary property. Two exceptional lifestyles. In a word...Perfection.

590 Sturges Hwy, Fairfield

69 Birch Rd, Fairfield
$5,750,000
4 Beds ⋅ 5 Baths ⋅ 24177449 MLS
Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with specific intention and the highest level of craftsmanship. Completed in 2025 with gunite pool, hot tub, full outdoor kitchen, new patio & shower with changing stall - no expense was spared. Inspired by the world's finest hotels & surpassing that quality on 3 floors of living space: sophisticated & timeless rooms designed for quiet family time or large scale entertaining, peaceful reading nooks, 4 ensuite Bedrooms which includes the luxurious Primary w/balcony, fireplace, walk-in closets, and spa-caliber bathroom with soaking tub & steam shower; media/playroom with vaulted ceilings and full bath with sauna. Timeless paneling, rich ceiling details, organic textures & fabrics, and harmonious natural stone accents create an atmosphere of understated refinement and enduring beauty. Engineered with advanced smart home technology, commercial grade WiFi, & soundproof insulation ensures a seamless at-home experience. Set within the multi-million-dollar enclave of Fairfield Beach and just a stone's throw to the expansive LIS shoreline, this irresistible residence embodies the art of living beautiful

69 Birch Rd, Fairfield

2268 Fairfield Beach Rd, Fairfield
$5,499,000
5 Beds ⋅ 6 Baths ⋅ 24194198 MLS
Experience the pinnacle of coastal luxury at this extraordinary waterfront builder's own residence on prestigious Fairfield Beach Road. Designed with uncompromising craftsmanship and impeccable attention to detail, this one-of-a-kind modern masterpiece offers the ultimate waterfront lifestyle with a private sandy beach and your own private dock. Showcasing over-the-top custom finishes throughout, featuring soaring ceilings, walls of glass that frame breathtaking water views, and an open, light-filled floor plan designed for both grand entertaining and everyday living. Offering five spacious bedrooms and five beautifully appointed bathrooms. At the heart of the home, the designer kitchen seamlessly flows into expansive living and dining areas, all oriented to capture the stunning waterfront setting. Outdoor living is equally spectacular. A 1,500-square-foot rooftop deck provides an unparalleled entertaining space with panoramic water views, while the resort-style outdoor amenities include a built-in outdoor kitchen, pizza oven, cooling station, and an outdoor shower-perfect after a day on your private beach or out on the water from your dock. This is a rare opportunity to own a truly exceptional waterfront residence where cutting-edge architecture, unrivaled craftsmanship, and an unmatched Fairfield Beach l

2268 Fairfield Beach Rd, Fairfield

195 Old South Rd, Fairfield
$4,950,000
4 Beds ⋅ 5 Baths ⋅ 24206984 MLS
Set on 1.25 acres in the heart of historic Southport Village, 195 Old South Road offers something increasingly rare: the character and presence of an 1829 Federal/Greek Revival residence with an unusually expansive yard. Private and surrounded by mature plantings, the 4,254-square-foot home offers four bedrooms, three full and two half baths across three floors. A gracious Front Hall, anchored by a sweeping curved staircase, opens easily to the home's principal rooms. The sun-filled, 30-foot Living Room features 9-foot ceilings and connects to the Dining Room through a passage framed by arched openings and a built-in wet bar. An expansive Family Room/Sunroom is accessible from the Living Room, Dining Room and Kitchen, creating an easy flow for everyday living and entertaining. Three wood-burning fireplaces add warmth and character. The generous Primary Suite features a gas fireplace, dressing room and private bath. A separate Guest Suite, two additional bedrooms and unfinished upper-level space offer flexibility. A substantial historic barn/garage accommodates two cars, with potential for three, and offers a full second floor. A large, level lawn provides remarkable privacy in close proximity to Southport Harbor, Southport Beach and Metro-North. A rare combination of acreage, architectural character and Village location. 195 Old South Road can be enjoyed immediately while offering its next owners the freedom to make the home distinctly their own over time.

195 Old South Rd, Fairfield

394 Penfield Rd, Fairfield
$4,700,000
6 Beds ⋅ 6 Baths ⋅ 24176873 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

394 Penfield Rd, Fairfield

1149 Fairfield Beach Rd, Fairfield
$4,500,000
5 Beds ⋅ 4 Baths ⋅ 24200980 MLS
TOES IN THE SAND & SUMMER EVERY DAY. There are waterfront homes-& then there are homes where the water becomes part of everyday life. Welcome to 1149 Fairfield Beach Road, a truly special direct beachfront home appprox 60+/- min from NYC. Thoughtfully designed by a builder for his own family, with an emphasis on capturing the extraordinary waterfront setting. Walls of windows fill the open living spaces w natural light and capture spectacular water views. Directly outside main-level family room w/no steps to the patio, is your own beach. Three of 4 waterfront bedrooms open to a wraparound deck, giving each its own connection to the water while creating private spaces. Wake to sun-filled rooms & end the day to the sound of waves. An impressive Great Room @ the mezzanine level is an inspiring addn'l gathering space that features 12' ceilings w skylights. Kitchen, bathrooms & laundry room updated in 2025. Rare garaged & off street parking for 10 Cars! An unfinished 3rd floor w private balcony offers potential for future 1,000+/- additional SF. Also Includes: Private STUDIO APARTMENT updated(2022) & awesome! Perfect for guests/extended family/home office or summer overflow just steps over @1148. Mins. to Schools, TOWN & TRAIN! ENJOY DIRECT BEACHFRONT living while being minutes from Downtown Fairfield, popular farmers market, outdoor & indoor concerts, restaurants w/ great outdoor seating, shoppes, movies, town events & the best of what Fairfield has to offer

1149 Fairfield Beach Rd, Fairfield

415 Old Post Rd, Fairfield
$3,975,000
5 Beds ⋅ 5 Baths ⋅ 24206348 MLS
Over an acre to yourself. The best of Fairfield within reach. In the heart of downtown Fairfield and the beach area, 415 Old Post Road offers something almost impossible to find: land and privacy to create a generational estate, with the life of a coastal town just beyond your gate. Only a handful of properties in the Sherman School district offer this. Fewer still could tell this story. The family who built this Italianate Victorian stayed for more than a century. Stand beneath its soaring ceilings, admire the craftsmanship, then step onto the screened-in porch. You begin to understand. Trees surround you. Church bells carry through the air. It feels like your own park. Yet the beach, schools, restaurants, shops and train are all within walking distance. For the current owners, that has meant children walking home from school with friends. Thanksgiving dinners for twenty. Additional bedroom options for overnight guests. Winter evenings around the parlor fire. A front porch filled with friends as the Memorial Day parade passes by. There is room here for the life you have imagined. Explore the possibilities for a pool, tennis court and gardens. Create a place where everyone gathers now-and where the next generation will want to return. Historic architecture. Meticulously maintained, thoughtfully updated and in pristine condition. A once-in-a-lifetime opportunity. Come discover what makes this place so hard to leave-and imagine what the next 50 years could look like.

415 Old Post Rd, Fairfield

406 Harbor Rd, Fairfield
$3,850,000
5 Beds ⋅ 5 Baths ⋅ 24181784 MLS
This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the Village. Hidden from the road, it offers a sense of seclusion that is increasingly difficult to find. Rich with period details and timeless architectural character, the 5 bedroom, 4 full and 1 half bath home sits at one of the highest points on Harbor Road, where cooling summer breezes are a welcome feature. The property also includes a classic antique barn, pool, pool house, attached one-car garage, and detached two-car garage, creating a setting ideal for both everyday living and entertaining. While the home presents an exceptional opportunity for renovation and enhancement, its greatest assets cannot be replicated: its setting, scale, history, and location. For the next steward, it offers the chance to reimagine a treasured Southport property while preserving its authenticity and charm. Enjoy a quintessential Southport lifestyle with easy access to the Village, train station, Pequot Yacht Club, and the soon-to-open Southport General Store and Rose Hill Kitchen. Last offered for sale in 1989, opportunities like this rarely come to market. A true Southport gem ready for its next chapter

406 Harbor Rd, Fairfield

624 Penfield Rd, Fairfield
$3,800,000
5 Beds ⋅ 6 Baths ⋅ 24217477 MLS
PRIME Beach Area Colonial, just 6 years young! Welcome to 624 Penfield Road, a home that brings people together; gorgeous water views, a private deck for watching 4th of July fireworks, steps to miles of sandy beaches & a new in-ground pool & spa await. Spend summer afternoons poolside, entertain family & friends beneath the covered loggia or unwind in the spa as the winter snow falls. This home is designed to create lasting memories. Offering 11 spacious rooms spanning 4 levels designed for comfort & flexibility. 9 ft ceilings, white oak hardwood floors, custom built-ins & detailed millwork create an atmosphere where every room is streaming w/ natural light even on the cloudiest of days. The well-designed eat-in kitchen features an oversized island, butler's pantry w/ wine fridge & cooling drawers & high-end appliances. The inviting family room offers a gas fireplace & opens to the deck, while a beautifully appointed office w/ custom built-ins provides access to the front deck. The formal dining room w/ custom millwork, also opens to the front deck, extending entertaining outdoors. Elevator provides access to all 3 levels. The upper levels feature 5 spacious en-suite bedrooms, a bonus room complete w/ a wet bar & 2 decks w/ water views. The new in-ground pool & hot tub w/ built-in grill area & loggia are surrounded by gorgeous coastal plantings. A generator, irrigations system, multiple decks, 3 car garage + great storage. The best of everything all in one in the beach area!

624 Penfield Rd, Fairfield

110 Judson Rd, Fairfield
$3,695,000
4 Beds ⋅ 5 Baths ⋅ 24193922 MLS
Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a higher elevation, the home enjoys FEMA compliance with fewer stairs to the main living level than many neighboring properties. Sunlight pours through oversized windows, illuminating beautifully proportioned living spaces designed for both everyday comfort and effortless entertaining. The stunning chef's kitchen opens seamlessly to inviting gathering spaces and out to a private backyard featuring a spacious patio, outdoor fireplace, mature landscaping, and room for a pool. The flexible floor plan lives as four bedrooms, with a private third-floor suite and adjacent full bath offering an ideal extra bedroom, guest retreat, office or bonus space. Thoughtful features, including a full-house generator, provide an added layer of comfort and confidence, allowing the home to perform as beautifully as it lives. Adjacent to the coveted Sunnieholme neighborhood, this is a rare opportunity to own a beautifully crafted home in one of Fairfield's most desirable beachside locations, where coastal living, convenience, and enduring quality come together.

110 Judson Rd, Fairfield

344 Fence Row Dr, Fairfield
$3,399,900
5 Beds ⋅ 8 Baths ⋅ 24194239 MLS
Old-world craftsmanship meets modern indulgence. Set on a peaceful, tree-lined street,this home offers total privacy and timeless curb appeal. Soaring ceilings, hand-finished millwork, and custom detail are evident throughout. This grand 5BR/6.5BA light filled residence pairs classic entertaining spaces - formal LR, formal DR, & a wood-paneled library w/wet bar & full BA-with modern amenities such as a two-story FR w/ stone FP, a stunning windowed sunroom overlooking the beautiful grounds,& an impressive chef's kitchen boasting custom appliances, double sub zero, island, & dual butler's pantries.Thoughtful proportions create a seamless flow, a home as comfortable day-to-day as it is for grand-scale entertaining.The opulent primary suite is a spa retreat onto itself, w/ dual baths, dual walk-in closets,& a private sauna.The second floor offers 3 add'l en-suite BRs w/ built-ins and large closets. The third floor offers a great room w/ custom built-ins, plus an additional BR and full BA . The lower level feat a recently upgraded state-of-the-art movie theater, gym, game room, & workshop for a serious hobbyist. The expansive, landscaped grounds offer true serenity, w/ English gardens framing a resort-caliber pool and spa in a backyard built for entertaining. Timeless elegance, tucked within The Ridge - a gated enclave w/ a staffed gatehouse, clubhouse, pool & tennis courts just minutes to Fairfield and Westport amenities. Truly a special offering w/ultimate privacy& convenience.

344 Fence Row Dr, Fairfield

1760 Hillside Rd, Fairfield
$3,150,000
5 Beds ⋅ 6 Baths ⋅ 24189678 MLS
Privately sited in the heart of Greenfield Hill, this updated home blends European-inspired architecture with the modern comforts today's luxury buyers value most. Rich in character, it offers soaring ceilings with exposed wood beams and skylights, wide-plank hardwood floors, custom built-ins, antique mantels, and repurposed antique doors throughout. The dramatic family room flows to a private office, wet bar, and chef's kitchen beneath an expansive skylight. The desirable first-floor primary suite has been transformed with a new spa bath, new gas fireplace, and atrium with a private entrance. Upstairs, a second primary suite features an en-suite bath, dressing room, fireplace, and private balcony. A renovated one-bedroom guest residence with new flooring, updated kitchen and bath, washer/dryer, and private entrance is ideal for extended family, guests, an au pair, or home office. Extensive improvements include a generator, water purification system, drainage system, irrigation, security system with cameras, restored and re-stained roof, renovated mudroom/laundry room, gardens with bluestone walkways and raised beds, and new front fencing. Expansive terraces overlook beautifully landscaped grounds with mature specimen trees and perennial gardens. Just minutes from town, beaches, train, restaurants, and Fairfield Country Day School, this exceptional Greenfield Hill property offers timeless character, privacy, and extensive improvements. Ready to enjoy from the day you arrive!

1760 Hillside Rd, Fairfield

145 Eastlawn St, Fairfield
$2,899,000
4 Beds ⋅ 5 Baths ⋅ 24217141 MLS
An exceptional NEW CONSTRUCTION home with ELEVATOR in Fairfield's coveted BEACH AREA! Built by a local premier builder, 145 Eastlawn Street spans 3,400 square feet across four beautifully designed levels, with room for a pool! This stunning 4-bedroom, 4.5-bath home offers ensuite baths in every bedroom a rarity sparing no expense, showcases exceptional craftsmanship, premium finishes, and thoughtful attention to every detail. The gourmet eat-in kitchen features custom cabinetry, a large center island, Quartz countertops, Thermador appliances and walk-in pantry. The kitchen is open to a spacious family room with fireplace and sliders leading to the backyard. A formal dining room, butler's pantry with wine fridge, powder room, along with a private study complete the main level. The upper levels offer four bedrooms and four baths, walk-in closets, laundry room, a bonus room and storage. Additional highlights include an elevator servicing three levels, a metal roof, 9-foot ceilings, white oak hardwood floors, private stone patio, lower-level loggia with mudroom, additional living space, storage and a 2-car garage. Enjoy the best of coastal living with Fairfield's vibrant downtown, beautiful beaches, top-rated schools, and everyday conveniences all just moments away!

145 Eastlawn St, Fairfield

372 Rowland Rd, Fairfield
$2,770,000
24175450 MLS
A Rare Opportunity in Fairfield's Most Coveted Neighborhood. As rare as a Ferrari Pininfarina Sergio or a Patek Philippe Sky Moon Tourbillon-each valued around $3 million- 372 Rowland Rd is a once-in-lifetime offering in Fairfield's Beach Area, combining unmatched location, size and potential. This exceptional 1.2-acre parcel, which has had only 1 owner, is ideally situated between vibrant Fairfield Town Center and the quiet exclusivity of Rowland Rd's private beach-w/ Penfield Beach just steps away. A pleasurable walk connects you to the train station, town hall, library, marina, shopping, fabulous restaurants, several beaches and Roger Sherman School. Enjoy the simple pleasure of walking to school. Boasting a prime southwestern exposure, this is the largest, fully developable parcel south of the Old Post Rd. This is a setting that could support an extraordinary 7,000+sq. ft. custom home with a separate 4-car garage, pool, pool house, tennis/pickleball court or party barn/studio. A private gated entrance would crown this future estate . For comparison, homes in the Beach Area-one of Fairfield's most desirable neighborhoods have sold in the millions of dollars, typically on 1/4-acre lot with limited flexibility. This property's scale and freedom are virtually unparalleled, an ideal setting for an architectural significant family compound. This is a blank canvas for a world class lifestyle - where design, leisure and privacy converge (continued).

372 Rowland Rd, Fairfield

1235-1236 Fairfield Beach Rd, Fairfield
$2,699,000
5 Beds ⋅ 4 Baths ⋅ 24141176 MLS
TWO incredible waterside opportunities await! That's right, not one, but TWO fantastic beach area homes are offered! With their direct waterfront locations (1235 - beachfront/LI Sound; 1236 - canal side), both homes have amazing water views, beach access and a convenient, fantastic location all in one! Both homes also offer excellent investment/rental opportunities. #1235 is rented for the '26-'27 college academic calendar year (Sept-May). 1236 is presently rented month-to-month. The home can be your beachside escape for the summer months - or rent it out monthly for additional income! When it's time for you to reside in the homes, create your own compound with a bright and airy house on each side of the water! 1235 has newer bathrooms, kitchen and tankless water heater. All newer windows on the beach-facing side of the home. Newer roof & skylights (2021). Recently painted exterior. Enjoy the incredible views of the Sound from the primary bedroom balcony! Take a dip in the sound and then come back from the beach & rinse off in the outdoor shower! 1236 has newer kitchen windows, re-sanded floors (2023) and has been repainted inside (2023). Hardwood floors throughout both homes (except for kitchen at 1236 (tile)).

1235-1236 Fairfield Beach Rd, Fairfield

204 Old Post Rd Unit 1, Fairfield
$2,695,000
3 Beds ⋅ 4 Baths ⋅ 24186935 MLS ⋅ The Enclave BLDG.
Introducing The Enclave, an exclusive new collection of eight luxury townhomes ideally situated along Old Post Road in the heart of Southport Village. Set within four intimate manor-style buildings, each housing just two residences, these four-level homes combine timeless coastal architecture with sophisticated modern living. Thoughtfully designed for both everyday living and entertaining, each residence features expansive open-concept living spaces, a private elevator servicing all four levels, chef-inspired kitchen, gas fireplace, two-car attached garage and exceptional private outdoor spaces, including a covered porch, rear deck and private fourth-floor roof terrace. A gated entrance provides an added sense of privacy and exclusivity. The Enclave offers a rare combination of privacy and village convenience, adjacent to Southport Park and just moments from Southport Village, Metro-North, the harbor, shops and dining. Currently under construction, with pre-construction opportunities now available.

204 Old Post Rd Unit 1, Fairfield

443 Brambley Hedge Cir, Fairfield
$2,695,000
4 Beds ⋅ 7 Baths ⋅ 24211002 MLS
Approached by a winding drive at the end of a quiet cul-de-sac in Fairfield County's premier gated community, The Ridge, this distinguished Colonial Revival residence is privately sited atop a gentle knoll on two beautifully landscaped acres. Expansive lawns, mature plantings, and private terraces create a tranquil setting with exceptional privacy. Spanning Four levels and approximately 7,300 square feet the home is designed for both comfortable everyday living and grand scale entertaining. A spectacular Great Room with fireplace flows into the light filled Kitchen and dramatic 2 story Breakfast Room, with both spaces opening to the terrace for effortless indoor-outdoor living and al fresco dining. A 2-story Foyer, formal Dining Room, Mudroom and home Office complete the main level. Accessed by front and back stairs the second level offers a luxurious Primary Bedroom featuring a fireplace, spa-like Bath and walk in closet, 3 additional en-suite Bedrooms and a large Bonus/Play Room. A sizeable third floor Craft/Office/Multipurpose Room provides exceptional flexibility including possible 5th Br. The home's striking appeal continues in the finished walk out lower level with mirror walled Gym and impressive Party/Game Room with fpl and fully equipped wet bar with wine cooler, ice maker and double drawer under counter refrigerators. Ideally located along the Fairfield/Westport line, The Ridge offers a true Country Club lifestyle with Clubhouse, Pool, Tennis Courts and Playground.

443 Brambley Hedge Cir, Fairfield

1074 Sturges Hwy, Fairfield
$2,690,000
5 Beds ⋅ 5 Baths ⋅ 24205145 MLS
A rare Greenfield Hill find, 1074 Sturges Highway pairs the presence of a classic Colonial with a sleek, thoroughly modern point of view. Thoughtfully reimagined, the home retains its original craftsmanship while introducing clean-lined updates and a minimalist sensibility that feels chic, current and effortless. Inside, the balance between old and new is masterfully struck. Original millwork and architectural details are paired with elegantly edited finishes, creating spaces that feel sophisticated without ever tipping into formal. The layout flows naturally for everyday living, with room to gather, entertain and simply enjoy the house. Set on over 2 acres of impeccably manicured and extremely private grounds, the property offers a rare sense of seclusion. A gorgeous patio with fireplace extends the living space outdoors, setting the scene for summer dinners, cocktails and fireside evenings. A newly constructed garage with loft above adds flexibility for a home office, studio, gym or creative retreat. Where classic architecture meets a fully modern point of view, 1074 Sturges Highway is a masterclass in understated sophistication. FAIRFIELD SCHOOLS: Schools: DWIGHT, LUDLOW, LUDLOW.

1074 Sturges Hwy, Fairfield

3007 Redding Rd, Fairfield
$2,549,000
4 Beds ⋅ 4 Baths ⋅ 24205159 MLS
Gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport center. Timeless natural beauty, distinctive architecture, exquisite craftsmanship & sophisticated updates combine to create a home that truly stands apart. Featuring 12 rooms flooded w/ brilliant light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife & stunning seasonal changes from vibrant autumn colors to peaceful snow-covered landscapes. The living room fireplace provides a cozy focal point w/ oversize French doors that open to the patio creating an ideal setting for outdoor dining & hosting. The eat-in kitchen offers the dining area, island, pantry & state of the art appliances & guides you to the dining room, office, living room & study. Upstairs the beauty continues w/ 4 large bedrooms including the primary. The lower level expands the living space w/ a new mudroom, rec room, gym & half bath. Updates include a new lower level, flagstone patio, custom pantry w/ wine storage, upgraded laundry room w/ new washer, new window in en-suite & new Rubbermaid track system. Step outside to your patio featuring a built-in Weber BBQ & XL Big Green Egg, perfect for cooking enthusiasts. Exterior has been meticulously maintained w/ repainting, stone-accented walls, Belgium block-lined driveways & ongoing landscaping. A NE bridge adds character. The Patterson Club is a bike ride away. 3007 Redding Road is filled w/ light, space & lasting memories.

3007 Redding Rd, Fairfield

98 Sasco Hill Ter, Fairfield
$2,479,000
5 Beds ⋅ 6 Baths ⋅ 24213890 MLS
Your Dream Home Awaits in Sasco Hill! New construction is about to begin! Now is the perfect time to get in early and customize this exceptional home to your own specifications. Beautifully designed 4-5 bedroom custom Colonial set on a quiet, tree-lined cul-de-sac in the highly desirable Sasco Hill location of Fairfield. Offering four levels of living space, exquisite custom millwork, and thoughtfully curated architectural details, this home is designed to blend timeless elegance with modern luxury. Enjoy the best of both worlds-a peaceful, country-like setting just moments from everything Fairfield/Southport has to offer. Walk to Southport Harbor or downtown Fairfield and enjoy the charm, shops, restaurants, and coastal lifestyle that makes this location so special. Don't miss this rare opportunity to create your dream home in one of Fairfield's most sought-after locations. Call today to arrange a meeting with the builders and make your vision a reality! Spring occupancy. Rendering is similar to home being built.

98 Sasco Hill Ter, Fairfield

72 Old Barn Rd, Fairfield
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 24212223 MLS
Winton Park is the type of address that people in Fairfield already know by name. Incorporated by special act in 1937, it is a private association spanning an est. 70 acres on just a few tree-lined streets w/stone pillars at the entrances, one-acre zoning, mature plantings, & the quiet authority of an established, walkable neighborhood. People call it "downtown's Greenfield Hill" for a reason. You get the soft structure & privacy of the Hill, & you are still inside the life of town. Introducing 72 Old Barn Road. This classic colonial has front & back staircases, a covered front entry, wood-burning fireplace, a screened porch & a private backyard w patio & built-in firepit. Hardwood floors run through the house, with charming design details & generous closets throughout.The large front-to-back chef's kitchen has top-of-the-line appliances and a large center island that seats six. Upstairs are 4/5 bedrooms & 3 full baths, including an oversized primary suite w/ a vaulted ceiling & large, walk-in closet. Beside it, a private second-floor office w/custom built-ins overlooks the backyard. A finished lower level offers room for a playroom & gym, den or game room. Winton Park is a neighborhood that cannot be replicated. Downtown Fairfield, shops, restaurants, theaters & Main Library, & Fairfield University are all right there. Ludlowe Middle School, Fairfield Ludlowe High School & the Metro North Station are a short walk or an easy bike ride away, along quiet side roads.

72 Old Barn Rd, Fairfield

24 Warde Ter, Fairfield
$2,349,000
5 Beds ⋅ 4 Baths ⋅ 24204921 MLS
Another Fabulous New Construction by Joseph J. Lagana Builders Inc. This Luxurious Colonial with masonary details is situated on a level .51 acre includes 5 Bedrooms & 4 full baths. 1st Floor: Living Room & Dining Room accented with feature walls of shaker paneling, Gourmet Kitchen includes Thermidor appliances & a spacious Center Island with seating for 4 & opens to a Family Room accented with a Wet Bar, Stone Fireplace & Paddle Fan. Private Office / 5th Bedroom with access to a full bath. Mud Room leads to 2 car garage. 2nd floor consists of 4 Bedrooms: Primary Bedroom Suite has a walk-In-Closet with built ins, En Suite Bath with Shower Stall & seperate Soaking Tub. Painted His/Hers Vanities, tile floor & sliding barn door. There is another En Suite Bedroom for Guests, Family or Nanny features Walk-In-Closet with Built Ins & Full Bath. 3rd & 4th Bedrooms share a Jack & Jill Full Bath. Laundry Room with Laundry Hook Ups, shelving, countertop & wash tub sink. Finished Basement with 800 sq ft. Expansive rear patio with paver stone includes a Firepit. Stone covered front porch & steps with detailed paver stone walkway. Professionally landscaped with lush green sod applied to front & rear yard, accented with plantings & Irrigation System. Also room for a Pool! Conveniently located near shopping, library, restaurants, gym, Lake Mohegan & access to 5 Town Beaches. Quick drive to Fairfield Metro Train Station, Merritt Pkway & I 95

24 Warde Ter, Fairfield

245 Cedar Rd, Fairfield
$2,349,000
4 Beds ⋅ 4 Baths ⋅ 24205683 MLS
Secluded Southport mini-estate built with character and attention to detail. Rarely do you find a home that needs nothing. Well loved and enhanced by the current owners including an upper level addition and expanded and renovated kitchen - the home and property have been improved and updated throughout their stewardship. Set on a gentle knoll at the end of a gated drive, enjoy sprawling lawns, professional landscaping and lighting, an inviting heated Gunite pool and enviable privacy. The exterior is further enhanced with a detached barn/garage, a treehouse featured in magazines and a sport court. Fall in love and watch the seasons change on your wraparound front porch. The recently renovated kitchen will delight every home chef. The kitchen and dining is open to a very spacious family room with fireplace, making entertaining a pleasure. Upstairs the romantic and secluded primary suite includes a full bath, plus a separate sitting room/study that is well suited for use as a home office, nursery or dressing room. There are now 3 additional family bedrooms plus two additional full baths. The finished lower level provides great play space and additional living area to enjoy. Gracious, tasteful finishes throughout with meticulous attention to maintenance and quality materials. This is an opportunity to truly have it all.

245 Cedar Rd, Fairfield

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