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$15,000,000
6 Beds ⋅ 8 Baths ⋅ 24032329 MLS
For 170 years, "Rose Hill" has graced the crest of Harbor Road, offering breathtaking views considered among the best on the East Coast. This magnificent Italianate landmark boasts 265 feet of direct waterfront access, complete with a private dock. Situated on nearly 2 acres, it stands as one of the largest and most commanding properties in Southport Village, offering unparalleled vistas of the Harbor, the Country Club of Fairfield golf course, and Long Island Sound. The meticulously restored Main House exudes charm and sophistication, featuring large public rooms with high ceilings that provide elegant spaces for entertaining. The spacious bedrooms and bathrooms offer stunning views, ensuring comfort and luxury. Additionally, a delightful guest apartment and wine cellar are located above the detached garage. Experience the epitome of refined living by dining al fresco, lounging by the pool, playing a game of bocce, tending to the garden, or relaxing on one of the many inviting porches. At "Rose Hill," every moment feels like a step back in time to an era when life was lived to its fullest.

385 Harbor Rd, Fairfield
$12,000,000
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
$10,650,000
5 Beds ⋅ 8 Baths ⋅ 24016258 MLS
EXCEPTIONAL MILLION DOLLAR PRICE ADJUSTMENT! This home is the most spectacular custom built waterfront estate on the Eastern shoreline coupled with the best value for direct waterfront homes! Private and gated entry welcome you to this coastal home that was selected amongst all mansions nationally & highlighted on an episode of Fox Business Mansion Global for its brilliance & beauty. Set on a direct waterfront 1 acre level lot with views of Southport Harbor & Long Island Sound. Spend your days watching the boating regattas from the Harbor, wake up to amazing sunrises, sip coffee from your balcony & enjoy all that this resort-like lifestyle offers. Abundant natural sunlight throughout the first-floor w/ a wall of glass doors that span the width of home that provide a landscape of breath taking and brilliant water views. This modern-day floor plan spared no expense w/custom high-end finishes, lighting, window treatments, mill work, & impressive details. Three levels of living, 9000+ SF, 17 spacious Rooms, 6 full & 2 half Baths, 5 en-suite Bedrooms including the Primary w/ a Sitting Room, his/her walk-in closets, & private Deck overlooking the water, 2 car Garage w/ 2 car lifts that services a total of 4 cars, 2000+SF unfinished lower level (not often found in waterfront homes) & whole house generator. The back yard features multiple Patios/Terraces & seating areas that surround your salt water Gunite pool w/ water views. 1 hour to NY City & minutes to harbor, train & village.

1093 Pequot Ave, Fairfield
$10,400,000
8 Beds ⋅ 16 Baths ⋅ 24026350 MLS
Imagine waking every morning to some of the most breathtaking water views on the East Coast. "The Sanctuary on Sasco Hill" is one of Fairfield County's most coveted properties. With the Manhattan skyline on the horizon, this gated, ultra-private estate features 6 levels of sun-drenched living and a charming 2-bedroom, 2-bath guest house. Blending intimate spaces with grandeur, the lifestyle allows for family comfort and the luxury of lavish entertainment. Floor-to-ceiling windows, French doors, and wood-burning fireplaces create a warm and inviting atmosphere. Granite patios with limestone railings, strategically placed on every level offer spectacular spaces for outdoor gatherings and moments of unparalleled sunrises and sunsets. The primary suite graces the entirety of the top floor, providing panoramic views from its expansive terrace. Six additional en-suite bedrooms with custom finishes and a large media/playroom occupy the 2nd floor. Enjoy summer afternoons by the inviting oval pool with a large shallow end and a full 9-foot deep end. Stay active on the squash court or swim laps in the indoor pool. The playground and enchanting gardens provide endless outdoor enjoyment. "The Sanctuary on Sasco Hill" is a turn-key property, available fully furnished and ready for immediate occupancy. Here, the seamless blending of indoor and outdoor spaces creates an unparalleled lifestyle of elegance and tranquility. Welcome to the epitome of luxury living only 50 mi from NYC.

640 Sasco Hill Rd, Fairfield
$9,750,000
5 Beds ⋅ 6 Baths ⋅ 24049021 MLS
Spectacular Pequot Avenue property that never made it to the market. Built in 1999, this Connecticut coastal home was recently transformed and appeared in several design magazines. Wonderful views over Southport Beach, the Sea Lodge and Long Island Sound. The property features a guest house, pool and pool house. Southport living at its very best. Comparable Sale Only: List Agent - Andrew Whiteley, Team AFA at William Raveis Real Estate, Sale Agent Kim Harizman, Compass.

1316 Pequot Ave, Fairfield
$9,050,000
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
$7,200,000
4 Beds ⋅ 7 Baths ⋅ 24114530 MLS
Introducing a breathtaking & architecturally striking waterfront estate on the Gold Coast - a treasure combining elevated design, top tier craftsmanship & smart luxury. Set on a rare .53 acre beachfront lot w/ 80+ ft of direct shoreline, this exceptional home offers 5,400sf of elegant living across 3 levels + a 560sf studio w/ a half bath - ideal for a guest suite or creative retreat. Wrapped in Alaskan yellow cedar siding, topped w/ a sleek standing seam metal roof & a wrap around porch the exterior exudes timeless sophistication & durability. Wide-plank hardwood flooring, exposed reclaimed natural beams & soaring ceilings truly set this home apart. State-of-art Crestron home automation, an elevator that services all levels, a whole-home generator, premium Lepage windows & Trustile 2" doors deliver peace of mind. Every inch of these stunning 12 rooms, both inside and out, presents something special whether it is a glorious water view, arched ceiling, custom mill work, built-ins, heated decks, heated driveway & front entry, radiant flooring on first level & full baths or natural stone paths - you will appreciate it all! Imagine your morning w/ beautiful sunrises, sipping coffee from one of several waterfront decks overlooking your colorful wild roses - the perfect backdrop. Spend your days enjoying swimming, kayaking or paddle - then relax in your hot tub after a beach stroll. Enjoy town July 4th fireworks from your own private beach...This is a slice of coastal paradise.

195 Fairfield Beach Rd, Fairfield
$7,000,000
4 Beds ⋅ 5 Baths ⋅ 170541837 MLS
SOUTHPORT WATERFRONT - SPECTACULAR ROCK POINT ON LONG ISLAND SOUND - With a sensational Long Island Sound location, at the mouth of idyllic Southport Harbor, this spectacular 1.8 acre property features 430 feet of waterfrontage with a Beach and panoramic, sweeping views of the Southport, Fairfield and Westport coastlines and Long Island Sound. A thorough renovation by renowned architect and New York Modernist, Charles Gwathmey, beautifully enhanced over 4000 square feet of living space, creating stunning interiors and expansive decking. Superb architectural detailing and elements are evidenced throughout. The main level offers Living Room, Dining Room, and the luxurious Primary Suite all opening onto the expansive Deck, a very well-appointed Kitchen, Powder Room and Butler’s Pantry/Laundry Room. The Terrace Level with Family Room and three well-proportioned Bedrooms, enjoys access to a covered Terrace, the inviting Pool, Beach, and Long Island Sound beyond. Within walking distance of Southport Village and Metro North Train Service to New York City, this is truly an extraordinary residence with an exceptional property and splendid waterfront location. Gated entries at street and property. Main Level: Entrance Hall with hardwood flooring and Guest Closet. Living Room with hardwood flooring, architectural cabinetry, open wood-burning Fireplace with slate surround, vaulted ceiling with Fan, and sliding doors to Deck. PLEASE OPEN ADDENDUM FOR FURTHER DESCRIPTION.

1095 Pequot Ave, Fairfield
$7,000,000
7 Beds ⋅ 10 Baths ⋅ 24097391 MLS
Welcome to 290 Sasco Hill Road-an extraordinary opportunity to own one of the most prestigious addresses in Fairfield County. Set on 1.75 beautifully landscaped acres atop iconic Sasco Hill, this 8,083 square foot estate offers sweeping views of Southport Harbor and the rolling greens of the Country Club of Fairfield's renowned golf course. A rare combination of water views and shared-private dock access make this home a standout in one of the most coveted enclaves on the Connecticut coast. Imagine waking up to boats gliding through the harbor and ending the day with sunsets over the Sound all from the privacy of your own backyard. The home blends timeless architecture with generous proportions, ideal for both everyday living and large-scale entertaining. Inside, elegant formal spaces flow effortlessly into sunlit casual rooms, all oriented to capture breathtaking views. A gracious primary suite with a private terrace offers a front-row seat to nature's show, while multiple guest bedrooms provide comfort and privacy for family and friends. Sasco Hill is known for its grand estates, commanding water views, and close proximity to Southport Village, beaches, and commuter train service to NYC. 290 Sasco Hill Road is an exceptional offering in a location where few homes change hands and even fewer offer such an unparalleled vantage point. Enjoy the best of waterfront living, New England charm, and timeless luxury-right here on Sasco Hill.

290 Sasco Hill Rd, Fairfield
$6,800,000
5 Beds ⋅ 9 Baths ⋅ 24033417 MLS
Coveted Southport waterfront. Builder's own 11,000+ sq. foot custom home on private Rock Point Road off Pequot Avenue and walking distance to Southport Beach and Village. Magnificent 1.9-acre lot with 200 feet directly on Long Island Sound with views towards Westport's Gold Coast of Beachside Avenue and the Manhattan skyline in the distance. A beautiful pool and pool house pull you outside to enjoy every changing tide and sky. Outstanding value when compared to neighboring sales and tremendous potential upside awaits the prudent purchaser. A similar sized lot on the street recently sold for $7m and the house directly next door sold in 2020 for $16.5m. Come and see for yourself. Don't miss out as all of our best local waterfront properties are being snatched up. Close to the town centers of Westport, Southport and Fairfield and just 50 miles to NYC.

1099 Pequot Ave, Fairfield
$5,551,060
4 Beds ⋅ 4 Baths ⋅ 24074057 MLS
ELEGANCE ON SOUTHPORT HARBOR - With an idyllic Village location, this elegant 3753 square foot, architect designed residence enjoys expansive water views over Southport Harbor and Long Island Sound. Exquisite rock gardens enhance the gently, sweeping .51 acre property extending to the Harbor's edge; a perfect launch for kayaking. The wonderful floor plan offers a stunning Living Room with Fireplace and banquet-size Dining Area, and a most luxurious Primary Bedroom Suite all opening onto a breathtakingly beautiful Deck Terrace presenting a Pergola, and a Dipping Pool with Spa, as well as an extraordinary designer Country Kitchen offering exceptional functionality, spacious Seating/Dining Area and superb finishes. The very spacious second floor features a sensational Great Room with vaulted ceiling, Office area, and spectacular water views, a Gym (or 5th Bedroom), and three additional generous Bedrooms. This unparalleled and peaceful haven of serenity and tranquility is only minutes to every convenience, beaches, exceptional dining, great shopping and cultural venues and Train Service to and from New York City. Historic District.

1060 Harbor Rd, Fairfield
$4,995,000
5 Beds ⋅ 5 Baths ⋅ 24005573 MLS
******The deadline for buyers to respond to the highest and best Wednesday 07/31/2024 at 11:59 PM***** Beautiful Sasco Hill estate includes four buildings on a beautifully landscaped 4.42 acre private lot. The main house, a farmhouse colonial is 6934 SF with 5 bedrooms and 4.5 bathrooms. The guest house has a full apartment on the 1st floor with a 2nd level private office. There is a fully finished lower level gym with a full bath, steam shower and large work out area. Each level has a separate entrance. In addition, there is a 863 SF heated and air conditioned pool house with full kitchen, full bathroom, family room with fireplace, laundry room and changing area. The fourth building is a 1800 sf 6 car garage with a heated and air conditioned commercial chef kitchen. There is a walk up 2nd level above the garage for additional storage. On the opposite side of the arched breezeway, is a large climate controlled white oak wine room with 10' ceilings which is attached to a wine tasting area and sunroom. In addition to the four buildings on the property, there is tennis court and a large covered patio with a stone fireplace and outdoor kitchen located in the pool area. Please see photos and be sure to watch the virtual tour for more details on this one of a kind, beautiful Southport 4.42 acre estate.

421 Sasco Hill Rd, Fairfield
$4,850,000
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
$4,750,000
5 Beds ⋅ 8 Baths ⋅ 24011858 MLS
Experience the epitome of luxury living in this enchanting Chateau-style residence nestled amidst verdant landscapes. With a picturesque facade reminiscent of a French countryside estate, this home exudes architectural magnificence and serene tranquility. Step inside through a Mahogany and glass pivot door to discover a grand staircase, vaulted ceilings, and professionally designed decor. A more suitable name for this kitchen might be the 'entertainment center', as it serves as the heart of the house, boasting the finest appliances and custom-built cabinetry of the highest quality, with French doors leading to a bluestone terrace. Enjoy captivating views of the landscape from every room in this recently completed multimillion-dollar renovation. The dining room features a glass-enclosed wine closet and dry bar made of Macassar Ebony, while the striking office offers magnificent built-ins. The primary suite impresses with French doors to a deck overlooking the pool, accompanied by a sitting room with a vertical fireplace. The primary closet/dressing room features lighted shelving and a stone-top center island dresser, while the spa-like bathroom offers a huge double shower, two brilliant white vanities, and a sparkling white oval soaking tub. Outside, discover the Carriage House with a large studio and 10 garage spaces, all situated on 6.47 acres of meticulously landscaped grounds. Indulge in luxury and elevate everyday living in this French chateau-a true masterpiece.

680 Old Academy Rd, Fairfield
$4,700,000
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
$4,500,000
5 Beds ⋅ 6 Baths ⋅ 170620815 MLS
Set down a private drive, at the end of one of Fairfield's most coveted & private waterfront cul de sacs, stands 420 Pine Creek Ave. Rare to the beach area, this nearly 5000sqft architecturally distinct home is substantial, timeless & undeniably exceptional. Boasting 5 bedrooms & 3.5 finished levels of living, the smart & luxurious design impresses at every turn. Enter the 3-story sunlit foyer through arched casement doorways to direct panoramic water views via windows & French doors. The main level features a bedroom w/ full bath, an open concept living/dining area w/ walls of glass overlooking the sea & outdoor living, both effortlessly flowing to an enviable kitchen. Fitted w/ the highest end appliances, fixtures & lighting, the Mahagony hues blend seamlessly w/ Calacatta Gold marble & white cabinetry. This level features 2 partial baths, an open-air office/study, mudroom & access to the great room. With vaulted-ceilings, this flex space is centered by a floating gas fireplace w/ leathered antique granite surround. The 2nd level primary suite spans the entire rear of the home w/ private balcony off bed & luxe bath...water vistas from every angle & an add'l 3 beds (one en suite) w/ built-ins & closet systems. The 3rd floor, w/ balcony, is an office & bonus/playroom. Once outside, enjoy a bluestone patio w/ built-in grill & covered Mahagony deck. Complete w/ floating dock for low-maintenance boating & walk to Pine Creek Beach. Waterfront lifestyle - redefined.

420 Pine Creek Ave, Fairfield
$4,500,000
4 Beds ⋅ 8 Baths ⋅ 170546989 MLS
Poised on over fourteen majestic acres in the heart of Greenfield Hill, this spectacular family compound enjoys unmatched privacy, minutes from shopping and dining. The estate consists of a main house, fieldhouse, and custom arboretum. Being sold AS IS and already gutted/prepped for future renovation, the main house with an English conservatory offers the opportunity to restore this breathtaking home or build your dream. Resort amenities include a swimming pool surrounded by a brick terrace, pool cabana, lighted tennis court, and three-stall tennis barn. The award-winning fieldhouse consists of a main level sitting area, a replica of the Mohawk Mountain swing, a regulation racquetball court, gymnasium, changing rooms with two showers and a shared half bath, and a loft perfect for game nights. An arbor and beautiful lit fountain offer an enchanting place to relax in the shade and enjoy the serene landscape. The custom arboretum offers 1,515 square feet of heated, mixed-use space, with geothermal, solar power and a back-up propane tank. The arboretum is also home to an office, half bath and two-car garage. Lastly, a serene and sun-filled 3.13 acre interior lot surrounded by mature trees could be developed or left as open space, with the option for a private entrance off of Old Academy Road, to complete your country estate.

1211 Old Academy Rd, Fairfield
$4,300,000
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
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
$4,300,000
4 Beds ⋅ 6 Baths ⋅ 24002786 MLS
Welcome home to your very own waterfront & creek side paradise at 2115/2116 Fairfield Beach Road. Nestled on the LI Sound shore, where you can walk on the sandy beach for miles, you will find this architectural masterpiece sparing no expense. All walls are encased in steel, triple pane windows, foam insulation throughout entire home, Boral siding & metal roof are a testament to this superior construction & ensure durability & peace of mind. Once inside you will find a wealth of high-end amenities designed for comfort & convenience. Easy access elevator services from the ground level to 1st & 2nd level & a solar panel system owned by seller with a HERS rating of 11 that powers home sustainability. Amazing features that make this home a standout include 3 levels of spacious living, 4 Bedrooms on same level, 5.5 Baths all w/ heated flooring, open floor plan, concrete heated flooring on main level, wide plank hardwood flooring on upper levels, laundry on both main & upper level, air filtration system to experience unparalleled air quality, 3 gas fireplaces, $80,000+ in high-end appliances, multiple decks & a stunning water view from every room. Enjoy the peaceful coastal lifestyle this gorgeous home offers PLUS Creekside water views, additional 2 car garage, & a permit secured for future dock. Cherish your unobstructed water views, sunrises, sunsets, beach activity & enjoy a vacation lifestyle all year.Minutes to town, train, dining, parks & 49 miles to NYC.

2115 Fairfield Beach Rd, Fairfield
$4,250,000
5 Beds ⋅ 6 Baths ⋅ 24093441 MLS
Nestled in the heart of historic Greenfield Hill, just steps from the iconic town green, this timeless 1840 Colonial has been meticulously restored and thoughtfully expanded to meet the needs of today's discerning buyer. With a provenance that includes architectural contributions by Cameron Clark (1930s) and Jim Thompson (2004), this home is a blend of historic integrity and modern elegance. Set on 3 acres abutting Fairfield Country Day School's playing fields, the home offers over 7,100 square feet of finished living space including a newly constructed primary suite. It features two oversized walk-in closets, a spa-like bath with soaking tub and glass shower, a gym, sitting area with built-ins and TV, and a dedicated office-all above a newly added two-car attached garage. The main level balances charm and flow with original moldings, wide plank floors, and sunlit living spaces. Two rooms were blended to create an expansive Great Room, perfectly positioned off the kitchen and opening through French doors to a flagstone terrace. Additional highlights include a newly added family room, a detached one-bedroom guest house with kitchen, full bath, and sleeping loft (currently an art gallery), and mature landscaping that ensures privacy all year.With architectural distinction, lifestyle flexibility, and an unbeatable location in one Fairfield's most sought-after neighborhood, 3113 Bronson Road is a rare opportunity to own a piece of New England history-reimagined for modern living.

3113 Bronson Rd, Fairfield
$4,200,000
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
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
$4,200,000
5 Beds ⋅ 6 Baths ⋅ 170593025 MLS
Introducing a Masterpiece of Modern Living: Your Dream Home with Breathtaking Views. Discover the epitome of luxury living in this state-of-the-art 4-5 bedroom, 5.5 bathroom masterpiece, spanning an impressive 5500 square feet. Nestled in a prime location, this architectural marvel offers unobstructed panoramic views of the serene Penfield Beach, ensuring you'll wake up to mesmerizing sunrises and wind down with awe-inspiring sunsets. Step onto your private balconies on every level, where you can savor the tranquil coastal breeze and take in the ever-changing hues of the ocean. Picture yourself indulging in indoor/outdoor living like never before, seamlessly blending the beauty of nature with the elegance of modern design. Unleash your inner chef in the outdoor kitchen, complete with a pizza oven, promising delectable creations as you dine al fresco. Every detail has been meticulously curated to offer the very best, ensuring top-of-the-line appliances and finishes throughout. Entertainment knows no bounds with an oversized gunite pool and spa, inviting you to create lasting memories with family and friends. The logia, an embodiment of sophistication, provides a shaded sanctuary for relaxation and outdoor gatherings. Ascend to the rooftop patio for a truly enchanting experience, as you entertain under the open sky or simply bask in the breathtaking vistas.

494 Lalley Blvd, Fairfield
$4,160,000
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
$4,150,000
5 Beds ⋅ 6 Baths ⋅ 24047166 MLS
Introducing an extraordinary modern transitional beach home, where luxury meets the laid-back charm of Fairfield Beach living. This newly constructed FEMA-compliant residence by Falzone Development renowned for his exceptional quality is a sanctuary of elegance and comfort. Inviting open layout and abundant windows create an airy ambiance. Chefs kitchen w/ Wolf, Sub-Zero & custom cabinetry. 5 well-appointed en-suite bedrooms. Incredible Primary suite, where you can wake up to the breathtaking waterviews of the sunrise. Step outside to the rooftop deck, an idyllic setting for relaxation or entertaining offering unobstructed views of LI sound, St. Marys & Penfield lighthouse. This home is not just a residence; it's a lifestyle. With the beach just steps away, you can indulge in the simple pleasure of a daily walk on the sand or embrace the vibrant beach community. The property also features a two-car garage with EV charger, an elevator for easy access to all levels and a home generator for peace of mind! Custom mill-work with high end finishes throughout! Maintenance free exterior with Hardie Board siding and Azek trim. Energy Efficient Heat/Cool, foam insulation for low monthly expenses along with many smart home features. Professionally landscaped property with multi-zoned irrigation and plenty of room for a POOL. Whether you're watching the sunrise from multiple decks or lighting a fire to enjoy the panoramic views of the Long Island Sound, this home is truly a rare find!

786 Beach Rd, Fairfield
$3,900,000
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
$3,900,000
4 Beds ⋅ 5 Baths ⋅ 170514432 MLS
Modern luxury new construction in prime Fairfield beach neighborhood...spectacular unobstructed views of LI Sound, St.Marys and Penfield Lighthouse and steps to your beach access. Our newest and most cutting edge design is showcased in this beachside new construction with sleek oversized windows, glass railings, custom crisp millwork, ELEVATOR, roof top party deck, multi-functional loggia (gym alternative), custom designer kitchen and baths, 1st and 2nd floor offices, wet bars, white oat 4-inch flooring and whole house auto gas generator & much more. With almost 4,000 sq.ft this home offers 4 bedrooms, 4.5 baths, 9 ft ceilings and an amazing flexible floor plan. Private landscaped property with bluestone patio and room for a pool! Get in on the ground floor and work with our designer to make this dream home yours. Be in for your 4th of July fireworks display in your front yard!!! You will love all Fairfield has to offer…beaches, bustling downtown, train, restaurants, boutiques, market, Sportsplex, parks and much more!

216 Fairfield Beach Rd, Fairfield
$3,875,000
5 Beds ⋅ 5 Baths ⋅ 170583172 MLS
A circular Motor Court with Cobblestones salvaged from the original Wall St in NYC introduces this 5 bedroom Brick Manor. Reflective of the French Countryside, this stunning residence has been reimagined to meet the requirements of today's most discriminating buyer. Majestically sited on over 2 acres of professionally landscaped grounds, including level lawns highlighted by towering Holly Trees, established location for a tennis court, Pool with Spa and Pool House, a formal Sculpted Garden, showcasing a century old Japanese Feather Maple tree, a gift from the Emperor of Japan. A stunning covered bluestone Terrace with FPL, patios for dining and relaxation and a graveled Fire Pit combine to make the most of this sublime property. The interior continues to impress with elegant formal rooms, including a dramatic step down Living Room with FPL and French Doors to Terrace, a Formal Dining Room with oversized windows and an Upper Level "Grand Salon" with barreled ceiling and FPL, a Wine Tasting Room with "Wine Cellar", a spectacular Sunroom with 3 exposures and an adjoining Study/Office with built ins. The Custom Kitchen with plentiful cabinetry and marble countertops opens to the Family Room with FPL and fully equipped wet bar, Pantry, Mudroom and Powder Room. Completing the second level, a Primary Bedroom with Luxury Bath and 4 additional bedrooms. A detached 3 car garage with attached office/guest cottage completes this estate. Just minutes to town, train and beaches.

415 Mine Hill Rd, Fairfield
$3,875,000
6 Beds ⋅ 8 Baths ⋅ 24096268 MLS
Tucked behind gates on two lush, private acres in Southport, this exceptional residence-featured in Fairfield Magazine-offers the ultimate blend of luxury, comfort, and convenience. Built by renowned Tallman Segerson builders, the transitional Georgian colonial was thoughtfully designed to evoke the feeling of a weekend retreat every day. Once a serene apple orchard, the property has been transformed into a beautifully landscaped haven, centered around a sun-drenched pool, a granite patio, and a charming pool house complete with a kitchen and bathroom. Whether you're basking in the sun, enjoying a sunset from the covered veranda, or curled up with a book on a rainy afternoon, every detail of this home invites relaxation. Inside, quarter-sawn oak floors lead you through an open, light-filled layout featuring an expansive kitchen and dining area perfect for entertaining. The grand primary suite offers ultimate privacy with dual bathrooms and walk-in closets, a sunlit office, and a private balcony. With four additional bedrooms upstairs, and a versatile third floor with space for a gym, playroom, or guest suite, this home adapts effortlessly to every lifestyle need. Ideally located just minutes from Southport Village, downtown Fairfield and Westport, two train stations, and New York City, this is not just a home-it's a sanctuary.

971 Hulls Farm Rd, Fairfield

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