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298 Harbor Rd, Fairfield
$5,995,000
5 Beds ⋅ 7 Baths ⋅ 24200591 MLS
What began as the restoration of sea captain Ward Bulkley 1834 home became something far more extraordinary. The years-long transformation of 298 Harbor Road, recently featured in Architectural Digest, brought together architect JP Franzen and Moore House Design to carefully preserve and reimagine nearly two centuries of history. No detail was too small and no opportunity to honor the original home overlooked. The result preserves the character and craftsmanship of another era while creating a home that, for all its beauty and pedigree, is remarkably comfortable, inviting and meant to be lived in. Generations of additions were reconsidered and unified; original pine floors preserved; millwork expanded; and Venetian plaster, reclaimed stone and artisan finishes introduced with extraordinary attention to craft. A spectacular vaulted kitchen centered around an 11-foot island exemplifies how seamlessly historic architecture and modern living were brought together. Behind the wood-paneled staircase, a hidden speakeasy offers an unexpected nod to another era-one of the many details that makes this home so intriguing. The home offers 5 bedrooms, 5 full and 2 half baths, with the rare flexibility of a first- or second-floor primary suite. Set on .8 acres with seasonal water views, a pool and spa, and outdoor sauna, 298 Harbor Road achieves something exceedingly rare: a remarkable convergence of history, exceptional design and modern luxury in the heart of Southport Village.

298 Harbor Rd, Fairfield
42 Puritan Rd, Fairfield
$4,100,000
5 Beds ⋅ 5 Baths ⋅ 24206950 MLS
Welcome to this next-level Fairfield Beach residence where bespoke luxury meets a fun coastal lifestyle. Just 2 blocks from the sand, this sun-drenched 5 bedroom, 4.5 bath beach haven is masterfully designed space. Every room tells a story through oversized windows, gorgeous textiles, designer wall coverings and unique lighting. The main living spaces are open, airy and filled with coastal light, featuring multiple entertaining areas for unforgettable gatherings and relaxation. From the culinary lover's dream Kitchen with Wolf, Bosch, SubZero appliances and walk-in pantry, to the Living Room anchored by a magnificent fireplace to a one-of-a-kind Bar with brass and smoked mirror accents, to the refined Study with incredible space and cabinetry. The Upper Two Levels delight with all 5 bedrooms being generously-sized and en-suite, offering ultimate privacy and luxury. The Primary Suite is so inviting with a private deck, luxurious bath with steam shower, radiant heat flooring and 2 walk-in closets. The Third Floor is a special and versatile private retreat featuring the 5th Bedroom, a lounge/exercise area, deck and dedicated workspace with built-in desks and wet bar. The interior flows effortlessly to a private resort-style backyard with mature evergreens and walls of hydrangea, Pool, Spa and Shower. Dedicated elevator space on 4 floors, EV charger, Sonos, Generator all ensure easy living AND Sherman Elementary, Beach, Restaurants are a leisurely walk or bike ride away.

42 Puritan Rd, Fairfield
80 Governors Ln, Fairfield
$3,999,000
6 Beds ⋅ 8 Baths ⋅ 24184556 MLS
As you enter 80 Governors Lane down a private driveway, discover an 8.5-acre estate blending timeless elegance with serene privacy. This circa 1933 farmhouse, designed by architect Jack Franzen and beautifully restored, features wide plank black walnut floors, exposed beams, and a bread oven fireplace. Six spacious bedrooms include a luxurious Primary Suite with vaulted ceilings, carved mantle fireplace, dual walk-in closets, and a private balcony. Five full and two half baths feature tumbled marble flooring and marble vanities for spa-like comfort. Warm living spaces with fireplaces and tall windows create perfect gathering spots, including a Formal Dining Room, a Den with wet bar, and a cozy Family Room. The chef's kitchen boasts custom cabinetry, Jerusalem stone countertops, a copper sink island, banquette dining, and terraces for al fresco meals. A heated breezeway links to a restored Goodspeed Farm barn, plus a one-bedroom apartment and a three-car garage for multi-generational living. The Pool House offers cathedral ceilings, a granite bar, and doors to stone terraces overlooking a heated Gunite pool, spa, and pond. Enjoy privacy with convenient access to top schools, fine dining, cultural venues, beaches, and NYC trains-an extraordinary sanctuary harmonizing nature and refined living.

80 Governors Ln, Fairfield
24 Tide Mill Ter, Fairfield
$3,500,000
5 Beds ⋅ 5 Baths ⋅ 24194823 MLS
Stunning new construction. Extraordinary design, finishes and craftsmanship with meticulous attention to detail.

24 Tide Mill Ter, Fairfield
297 Lalley Blvd, Fairfield
$2,950,000
4 Beds ⋅ 5 Baths ⋅ 24208527 MLS
There are few places in Fairfield where life feels this easy. At 297 Lalley, the beach, train, town, schools, restaurants, and farmers market are all within easy reach, yet home feels remarkably private, spacious, and peaceful. Custom built with exceptional attention to how people actually live, the home is open, bright, and filled with natural light. At its center is a dramatic kitchen anchored by a single slab of Danby marble, creating an island that naturally becomes the gathering place. Thoughtful details are everywhere, from two dishwashers and generous storage to carefully planned circulation that makes entertaining effortless. The connection to the outdoors is equally compelling. The kitchen and family room open toward an indoor/outdoor fireplace, creating an inviting setting from spring through fall, with the pool and patio just beyond. Beneath the home is a tremendous amount of additional storage, with the flexibility to create a future garage if desired. Upstairs, the third-floor "crow's nest" rises above the neighboring homes, offering a fifth-bedroom option with a full bath. It's a quiet retreat with views toward Long Island Sound. Morning brings sunrise over the water; evening brings sunset from the front porch. Walk to the beach, bike to the farmers market, head into town for dinner, or catch the train to New York without adding another commute to your day. Spacious, comfortable, and beautifully designed, this home captures the best of Fairfield Beach living.

297 Lalley Blvd, Fairfield
420 Morehouse Ln, Fairfield
$2,950,000
6 Beds ⋅ 7 Baths ⋅ 24188287 MLS
Nestled on a private lane, this Southport luxury estate offers a pin-drop quiet setting just minutes from Southport Village, Southport Harbor, the Southport train station, I-95, and the Merritt Parkway. Set on over two level acres, it blends tranquility and convenience. The home features six bedrooms, including a gracious first-floor primary suite with a fireplace, dual spa-like bathrooms, separate dressing areas, and French doors opening to landscaped gardens. A wood-paneled library with a wet bar and a guest suite with a private staircase and full bath add character and flexibility. The country kitchen features wide-plank pine floors, tiled countertops, and Traulsen and Wolf appliances. Outside, an expansive pool, stone terrace, outdoor fireplace, private lighted hardtop sport court, and nine-stall barn showcasing original architectural details complete the setting. Formerly owned by Hall of Fame quarterback Joe Namath.

420 Morehouse Ln, Fairfield
108 Colonial Dr, Fairfield
$2,795,000
5 Beds ⋅ 4 Baths ⋅ 24211346 MLS
Set in the coveted beach area of Fairfield, this gracious five - bedroom Center Hall colonial combines classic architecture character with exceptional privacy and beautifully appointed living spaces. Approached by stone walls and professionally landscaped grounds, the property offers a serene and inviting setting just moments from the beach. Inside, a welcoming center hall leads to generously proportioned rooms, while the cook's kitchen is designed for entertaining. The ceilings on the 1st floor are 9 foot with formal and informal living and dining areas. A large mudroom and half bath are located near the entrance to the garage. All five bedrooms are located on the 2nd floor. The primary bedroom has a full bath with soaking tub, shower and sauna. There are numerous closets and a sitting nook. There are 3 full baths on the 2nd floor with a laundry room. Throughout the home there are time-less details, built-ins, wainscoting and seating areas. This is a special Fairfield home that captures the best of relaxed coastal living. This home is minutes to the beach, Universities, town, train and 95.

108 Colonial Dr, Fairfield
42 Anvil Rd, Fairfield
$2,699,000
4 Beds ⋅ 4 Baths ⋅ 24191278 MLS
Welcome to Southport! 42 Anvil Rd is a truly custom home, distinctly different in quality and design from the neighboring Toll Brothers builds. Situated on a quiet cul-de-sac with only six homes and backing up to conservation-protected land, it offers exceptional privacy and a serene setting. Step out back to the elevated Brazilian Ipe deck which provides the perfect space for relaxing mornings and sunset dinners. Savor the quiet! Thoughtful details fill every room, from the handsome custom walnut Kitchen island to the stunning Family Room with soaring cathedral ceilings, plentiful windows and French Doors and unique custom finishes throughout. Work from home in the private Office on the main level with a view of your back yard. On the second level, the spacious Primary Suite features spa-inspired luxury with custom wood accents, while three additional Bedrooms accommodate your family and guests beautifully. Do not miss the extraordinary additional living spaces in the Walkout Lower Level including the 5th Bedroom with ensuite Full Bath, a Recreation Room, heated/cooled Full size Gym with 9+ foot ceilings and a heated/cooled two car Garage. 42 Anvil provides versatile living options with the ultimate thoughtful detail. This home is more than just a house, it is a peaceful sanctuary crafted for those who appreciate bespoke design and quality. Come see for yourself how 42 Anvil Rd redefines living in coveted Southport.

42 Anvil Rd, Fairfield
476 Mill Hill Ter, Fairfield
$2,675,000
5 Beds ⋅ 6 Baths ⋅ 24197346 MLS
Beautifully crafted new construction in coveted Southport by a three-time HOBI Award-winning builder, with anticipated completion in Spring 2027. Set on a serene .43-acre property, this thoughtfully designed home will offer over 5,200 square feet of finished living space across four levels, including third-floor bonus space and a walk-out lower level. Featuring 5 bedrooms and 5.5 baths, the home will offer timeless design, refined craftsmanship, and modern comfort. The sun-filled main level provides an open-concept layout with 4-inch white oak hardwood floors, a chef's kitchen with Thermador appliances, custom cabinetry, quartz countertops, and a walk-in pantry, plus a spacious family room with a gas fireplace and access to a paver patio for easy indoor-outdoor entertaining. Upstairs, the primary suite includes a spa-like bath with heated floors, alongside 3 additional bedrooms and a laundry room. The third floor adds a home office, bonus space, and full bath, while the walk-out lower level includes a gym, media lounge, and private guest suite. Additional features include spray-foam insulation, 5-zone HVAC, EV charger, and 2-car garage. Ideally positioned near Fairfield's beaches, vibrant downtown, highly regarded schools, and Metro-North, the home offers an effortless commute paired with coastal charm and a welcoming sense of community. Early buyers may have the opportunity to customize select finishes and make this extraordinary Southport residence their own!

476 Mill Hill Ter, Fairfield
3080 Sturges Hwy, Fairfield
$2,499,000
5 Beds ⋅ 7 Baths ⋅ 24190034 MLS
Welcome to 3080 Sturges - Fully Renovated Home set on 2.44 private acres in Fairfield's Greenfield Hill enclave on the Westport border. Offering a Westport mailing address together with Fairfield's acclaimed schools and amenities, this 7,317-square-foot modern residence blends architectural scale with contemporary comfort and luxury. A dramatic two-story foyer introduces interiors defined by soaring ceilings, skylights, and oak hardwood floors throughout the home. Just off the foyer, a screened porch offers a peaceful setting for indoor-outdoor living and entertaining. Designed for both everyday living and entertaining, the main living spaces center around a gourmet eat-in kitchen appointed with Sub-Zero refrigeration, a Wolf range, Wolf double ovens, Wolf built-in microwave, Miele dishwasher, Marvel undercounter ice machine, quartz countertops, and a gas fireplace. Complementing the kitchen is a walk-in pantry featuring a second full refrigerator, wine refrigerator, and custom cabinetry for exceptional storage and organization. Adjacent to the kitchen, the formal dining room features custom built-in cabinetry and ample space for entertaining. Additional highlights include a grand living room with dramatic cathedral ceilings, expansive skylights, and exceptional scale, flowing into an adjacent music room with a custom tray ceiling. The home also features a private office with fireplace, billiards lounge, fitness studio, and a second laundry room.

3080 Sturges Hwy, Fairfield
446 Wormwood Rd, Fairfield
$2,299,000
4 Beds ⋅ 4 Baths ⋅ 24206534 MLS
Exceptional New Construction in the University Area. Nestled on a quiet, low-traffic street in the heart of the desirable university neighborhood, this stunning new construction home perfectly blends luxury craftsmanship, modern functionality, and unmatched convenience. Currently under construction with a planned completion for May, this property offers a rare window of opportunity for buyers to step in, select custom finishes, and truly tailor the design to fit their personal vision. Built by one of the region's most well-known and respected local builders-celebrated for high-quality architectural detail and a proven portfolio of exceptional homes- this residence is thoughtfully designed inside and out. Spacious living: designed with an open, modern flow featuring 4 generous bedrooms and 3.5 baths, ideal for both everyday living and formal entertaining. Customization Potential: Early buyers can consult directly with the builder to select key interior options, fixtures, and personalized details before construction wraps. Refined Craftsmanship: Expect premium trim work, high-end surfaces, and beautiful architectural touches throughout the entire footprint. Unbeatable Location and Accessibility. Tranquil Setting: Enjoy the peace of a secluded, quiet neighborhood within a vibrant university setting. Commuters Dream: Central access puts you minutes away from local trains, downtown shopping and dining, and major highway corridors for easy travel. Opportunity awaits!

446 Wormwood Rd, Fairfield
90 Fern St, Fairfield
$2,299,000
4 Beds ⋅ 3 Baths ⋅ 24188568 MLS
The summer beach listing buyers have been waiting for is Coming Soon to the market! Ideally located in a prime beach setting, FEMA compliant and picture-perfect, this inviting coastal home is set on a gorgeous, level .28-acre lot with stunning native plantings and colorful landscaping with plenty of room for a pool. The current homeowners have thoughtfully enhanced the property, including a freshly painted interior and professionally designed landscaping, making this move in ready. A spectacular rooftop elevates the experience, offering magical sunset views and unobstructed July 4th fireworks. Inside, 12 spacious rooms spanning four levels provide great space for everyday living with a room for everyone as well as great entertaining. The eat-in kitchen features high end Wolf and Sub-Zero appliances, while custom built-ins, French doors, abundant natural light and thoughtful details throughout this home add character and warmth. 90 Fern Street presents an amazing opportunity to enjoy both the beach lifestyle and be able to walk to town, school, park, train, shopping and dining.

90 Fern St, Fairfield
201 Whites Hill Ln, Fairfield
$2,095,000
6 Beds ⋅ 9 Baths ⋅ 24202996 MLS
Just a few blocks from the Greenfield Hill Green, an extraordinary opportunity awaits: a beloved estate, held by the same owners for more than 20 years, now reimagined for its next chapter. Taken virtually to the studs and thoughtfully rebuilt, much of the transformative work has already been done - creating the rare opportunity to step in at an exciting moment and complete a nearly 9,000-square-foot home entirely to your own vision. A new roof, siding, insulation, Marvin windows and doors, subflooring, extensive plumbing rough-ins and systems are among the significant improvements already in place, along with an exceptional newly built four-car garage. What remains is the rewarding part: the finishes, details and personal choices that will make it yours. Set on one of Greenfield Hill's picturesque properties, the home's generous, light-filled floor plan was designed for both everyday living and effortless entertaining. The main level flows between expansive living and family rooms, an eat-in kitchen, office, mudroom and potential first-floor en-suite bedroom. Upstairs, beautifully proportioned en-suite bedrooms offer privacy and flexibility, while the space above the four-car garage presents the potential for a private two-bedroom, two-bath guest or in-law suite with its own entrance.

201 Whites Hill Ln, Fairfield
50 Brookbend Rd, Fairfield
$2,050,000
5 Beds ⋅ 5 Baths ⋅ 24193848 MLS
An extraordinarily rare opportunity in Fairfield's coveted Winton Park Association. Offered for the first time in over 4 decades, this timeless 5-bedroom, 4.5-bath Colonial is set on nearly 2 breathtaking, park-like acres, offering estate-like privacy w/an unparalleled walk-to-town lifestyle. A gracious foyer welcomes you inside, where a magnificent staircase, wide-plank hardwood floors & exquisite millwork define the home's enduring character. Oversized windows & beautifully scaled rooms reflect craftsmanship rarely found today. The step-down living room showcases elegant paneling, custom built-ins & a wood-burning fireplace, while the formal dining room opens through French doors to a private patio for effortless indoor/outdoor entertaining. The spacious eat-in kitchen overlooks spectacular grounds & opens to a sun-filled family room w/custom built-ins, 2nd fireplace & French doors to an enchanting brick patio w/tranquil waterfall. Upstairs offers 4 spacious bedrooms & 3 full baths including a gracious primary suite w/abundant closet space & ensuite bath. Private guest suite w/separate entrance, vaulted ceilings, fireplace, 5th bedroom & full bath. Expansive, level grounds offer endless possibilities for a pool, pool house, ADU or future expansion in a setting rarely found just moments from downtown, Metro-North, award-winning schools & beaches. Complete w/natural gas, public sewer, irrigation & attached 3-car garage. A legacy property ready for its next chapter.

50 Brookbend Rd, Fairfield
550 Wellington Dr, Fairfield
$1,925,000
4 Beds ⋅ 4 Baths ⋅ 24206227 MLS
Tucked at the end of a quiet Greenfield Hill cul-de-sac, 550 Wellington Drive feels like a true retreat-private, peaceful and designed for the way you actually want to live. Set on 2.47 secluded acres, this 4-bed, 4,776sqft home offers an exceptional amount of space to gather, entertain and spread out, with a floor plan that gives everyone a place of their own. The 1st floor is especially expansive, with a gracious living room, dramatic vaulted family room, oversized playroom, sunroom and sophisticated wood-paneled office-spaces that easily adapt for entertaining, working from home, play or simply finding a quiet corner to unwind. The kitchen sits at the heart of the home, creating an easy connection between everyday living and the many gathering spaces. Upstairs, four bedrooms provide a comfortable separation from the main living areas, complemented by recently updated bathrooms. Outside is where 550 Wellington truly becomes an escape. Surrounded by mature landscaping and complete privacy, the backyard resembles a private resort with pool, expansive deck, screened-in porch and abundant space for outdoor dining, entertaining and long summer days at home. A three-car garage completes the offering. Spacious yet inviting, private yet close to everything Greenfield Hill has to offer, 550 Wellington Drive is a homemade for gathering, entertaining and getting away-without ever having to leave home.

550 Wellington Dr, Fairfield
50 University Dr, Fairfield
$1,499,000
4 Beds ⋅ 3 Baths ⋅ 24204891 MLS
Welcome to 50 University Dr, where character, craftsmanship, and comfort come together effortlessly. Tucked into one of the most coveted enclaves near Fairfield University, this colonial-style home was custom built from the foundation up in 2021 with refined finishes and carefully selected upgrades. Outside: cedar shake siding, Azek pergola and trim, Trex decking, oversized Nicolock patio, horseshoe driveway, Marvin windows and doors, and a full-house generator. The landscaped grounds include a "dog proof" fully fenced backyard. Inside, 8" white oak floors run throughout, with high ceilings, modern trim, neutral paint, and brass and aged brass hardware. The kitchen connects to the garage and sits between the family and dining rooms for effortless entertaining. A walk-in pantry doubles as "kitchen overflow" to hide clutter. It's finished with custom cabinetry, Bosch SS appliances, quartz counters, and a large island with hidden storage and seating for 3. The 1st floor also offers a formal living room with custom marble-surround gas fireplace, a full bath, and a bedroom that works as an office or guest room. Upstairs, the primary suite features a tray ceiling, large walk-in closet, and spa-like bath with heated tile floor, double vanity, and glass-door tiled shower with heated seat. 2 more bdrms have vaulted ceilings, ceiling fans, and closet systems, served by a 3rd full bath. Timeless character and lasting quality, ready from day one.

50 University Dr, Fairfield
85 Osborne Pl, Fairfield
$1,495,000
5 Beds ⋅ 3 Baths ⋅ 24186094 MLS
Welcome to 85 Osborne Place - this beautifully updated 5-bedroom, 2.5-bath Colonial tucked away on a peaceful street, yet just a stroll from the train, shops, and dining is what makes Southport living so desirable. Step inside this turn-key gem to find a bright, flowing floor plan anchored by an updated kitchen that opens seamlessly into a spacious great room - perfect for everyday living and effortless entertaining. A formal dining room and separate living room with fireplace offer classic charm and flexibility, while a dedicated office makes working from home a breeze. The first-floor primary suite gives main-floor living its name with a layout for everyday ease that's hard to find. Upstairs you will find 4 additional bedrooms and an updated hall bath that provide room for everyone. Head down to the finished lower level, where a large rec/playroom awaits - easily reimagined as a home gym, media room, or man/she cave to suit your lifestyle. Outside, your own private retreat: a lovely, fenced yard offers space to play and garden, while the patio with option for shade by a charming awning - is made for morning coffee or evening unwinding. With its unbeatable location, versatile living spaces, and move-in-ready updates, this Southport Colonial checks every box. Don't miss your chance to make it home.

85 Osborne Pl, Fairfield
694 Jennings Rd, Fairfield
$1,399,000
4 Beds ⋅ 4 Baths ⋅ 24209649 MLS
Exceptional opportunity to own what is essentially a brand-new home in Fairfield University area. Expanded with a full second-story addition and reconstructed from the original foundation up, this remarkable residence offers 3,290 square feet of beautifully finished living space with virtually every major component newly built. Designed for today's lifestyle, the open-concept floor plan features 4 bedrooms, 4 full baths, and flexible living space across three levels. The heart of the home is a stunning chef's kitchen with Thermador appliances, quartz countertops, abundant cabinetry, and a large island, opening to a dining room with coffered ceilings, and seamless flow into the living room, creating an ideal setting for both everyday living and entertaining. A first-floor bedroom and full bath provide flexibility for guests, a home office, or multigenerational living. The second floor features a spacious primary suite with a walk-in closet and beautifully appointed primary bath, along with two additional bedrooms, another full bath, and a conveniently located laundry room. The finished third floor offers a spacious office with glass French doors, valuable bonus space perfect for a playroom, media room, or guest retreat, along with a full bath. Beyond the attractive finishes, conveniently located near Fairfield's beaches, train stations, shopping, dining, parks, and top-rated schools, 694 Jennings Road offers a rare combination of modern design, turnkey living.

694 Jennings Rd, Fairfield
394 Wakeman Rd, Fairfield
$1,399,000
4 Beds ⋅ 4 Baths ⋅ 24205035 MLS
Step into a storybook setting of Fairfield's "CT Cotswolds." This 1931 custom-built Cape Colonial is a masterclass in timeless elegance, where old-world character seamlessly blends w/high-end modern comforts. From the moment you cross the flagstone-covered front porch & enter the foyer, the home's heritage shines through the graceful curved staircase & rich wide-board flooring. The main level is designed for both sophisticated entertaining & quiet relaxation. The impressive LR anchors the home w/its wood-burning FP & beamed ceilings, while the formal DR delights w/artisan details like classic corner cabinetry. For those seeking a quiet retreat, the sun-drenched den serves as the perfect library or bright home office. At the heart of the home, the gourmet chef's kitchen is a showstopper. Vaulted, beamed ceiling & expansive windows frame views of the lush grounds, while Viking appliances, granite countertops, & clever storage solutions cater to the most ambitious culinary pursuits. The 1st flr Primary suite is a sprawling sanctuary featuring b/i closets, bath w/dbl shower, & private sitting room for peaceful mornings. Upstairs, 3 add'l bright BRs & FBA. The fin LL is the ultimate destination for game days, complete w/wet bar, b/ins, 1/2 bath, office space. Outside, the property transforms into a private oasis. Exquisite perennial gardens wrap the home in color, providing a stunning backdrop for alfresco dining. It's more than just a house; it's a retreat that feels like HOME.

394 Wakeman Rd, Fairfield
148 Szost Dr, Fairfield
$1,399,000
5 Beds ⋅ 7 Baths ⋅ 24191205 MLS
Completely reimagined from top to bottom, 148 Szost Drive offers the rare opportunity to own a move-in ready home on one of Fairfield's most sought-after neighborhoods. Thoughtfully renovated with today's lifestyle in mind, this 5-bedroom, 5.5-bath residence spans over 3,800 square feet on nearly a quarter-acre, blending timeless design with exceptional functionality. Designed for the way people live today, the home features an effortless flow between multiple living spaces and a beautifully renovated open kitchen that naturally becomes the heart of the home. Upstairs, spacious bedrooms include multiple en-suite baths, while the finished third floor offers exceptional flexibility with a bonus room, home office option, full bath, and comfortable space for guests. The extensive renovation extends well beyond the cosmetic updates, with significant investments including a new HVAC system, new radiant heat throughout the first floor, thoughtfully designed custom storage, and a beautifully reimagined second-floor laundry room. Every improvement was made with comfort, efficiency, and everyday living in mind, creating a home that feels as functional as it is beautiful. Outside, the private backyard offers plenty of room to relax, entertain, and play, while the attached garage includes an EV charger for added convenience. Ideally located just moments from Fairfield's beaches, downtown, train station, parks, & everything that makes the University neighborhood so desirable.

148 Szost Dr, Fairfield
1495 Westport Tpke, Fairfield
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 24047873 MLS
Rich in character and designed for today's lifestyle, this distinctive Fairfield home is privately set on two picturesque acres, framed by classic New England stone walls, white fencing, mature trees, open lawns, a quintessential red barn, and a detached two-car garage. The setting offers exceptional privacy while beautifully balancing Fairfield's country landscape with the convenience of its location. Thoughtfully renovated and expanded in 2012, the home offers an elevated, modern living experience while preserving the architectural details that make the property unique. The beautifully appointed chef's kitchen, with top-of-the-line appliances, opens seamlessly to a great room with soaring vaulted ceilings, a handsome fireplace, walls of windows overlooking the property, and sliders to the private deck. Designed for both entertaining and everyday living, the open layout creates a natural gathering place and an effortless connection to the outdoors. Adding to the home's timeless character are its circa-1749 origins, beautifully preserved through select period details, including the King's Board flooring-an architectural feature traditionally found in some of New England's earliest homes. An adjoining room offers exceptional flexibility as a library, study, or intimate sitting room.

1495 Westport Tpke, Fairfield
58 Meadow Ct, Fairfield
$1,295,000
3 Beds ⋅ 3 Baths ⋅ 24204742 MLS ⋅ Meadow Court Condominium BLDG.
A lifestyle you can truly enjoy - the perfect blend of luxury, privacy, convenience and low-maintenance living. Set on a quiet 10-home cul-de-sac near Fairfield's town and beach areas, this renovated home is filled with natural light and offers an ideal open floor plan, 9' ceilings, two office spaces and a private, fenced rear yard with patio. From the moment you enter, the thoughtful design is apparent. French doors open to a private office off the front entry, while the home unfolds into an expansive open living space where the living room, dining room and kitchen flow seamlessly together. The living room features a gas fireplace flanked by windows and sliders to the backyard, while a wall of windows along the rear of the home fills the space with natural light and creates an easy connection to the outdoors. The kitchen features a natural wood island, Quartz countertops, Viking Professional stainless-steel appliance suite, Bosch dishwasher and adjoining bistro area. A 2-car garage provides direct access to a sizable pantry, mudroom and powder room. Upstairs, a primary suite features vaulted ceilings, nearly floor-to-ceiling windows, a WIC and an expansive full bath with a wall of White Dove cabinetry, Jacuzzi and tiled shower. Two additional BRs, a laundry room, full bath and open-air office complete this level. A walk-up attic offers storage and potential living space. Turn-key, light filled and ideally located close to train to NYC, beaches, parks, dining, shopping!

58 Meadow Ct, Fairfield
130 Elm St, Fairfield
$1,225,000
3 Beds ⋅ 3 Baths ⋅ 24203250 MLS
Walk to Town, Train, Fairfield U, University Area Location. 2/3 acre. Ample Living Space. Character. A stand out in its price range w/ NEW ROOF! Rarely does one find a quintessential center hall colonial w/ abundant architectural details, charm, condition & updates, all in the heart of Fairfield! Travel down the long private drive to the secluded garden & up the charming porch. Inside, the Formal Dining Room & Living Room each flow effortlessly to the Great Room & Kitchen. The LR impresses with original wide plank flooring, space, fireplace and french doors to the Great Room. There, walls of windows overlook a sunny & delightful view of the expansive rear property. Wainscot accents, sliders, dining area and red brick floor beneath it all complete the space. Columns lead to an open kitchen where the home's vintage flair truly comes to life. Solid wood cabinetry, copper sink, even a rotary dial wall phone! Beyond, the hall leads to a tasteful powder room w/ pocket door, laundry, pantry, and steps down to a traditional family room w/vaulted ceiling & beams. Here, cozy up to a second fireplace. More sliders lead to the rear brick patio, while additional entries allow access to the front garden and garage. Upstairs features a primary suite w/ modern bath, vaulted ceilings & beams, two guest bedrooms, one w/door to 2nd fl. deck, modern hall bath, and hardwood throughout. Roof '26, Washer/Dryer '26, Front Door '25, Deck '23, Furnace '21, Siding '17, MBTH '15, Addition '04.

130 Elm St, Fairfield
1951 Burr St, Fairfield
$1,175,000
4 Beds ⋅ 3 Baths ⋅ 24206877 MLS
*OFFERS DUE 5PM 9/21* Welcome to this quintessential New England colonial, lovingly cherished by the same owner for over 4 decades. On 2 flat, picturesque acres, this timeless home offers serene, private living while remaining centrally located. A sweeping circular driveway creates a warm arrival, while the sprawling, level backyard provides an ideal setting for outdoor entertaining, with room for a pool and pool house.Inside, traditional character shines with hardwood floors throughout. The main level is designed for both casual daily life and formal hosting. The heart of the home features an expansive eat-in kitchen anchored by a center island, ideal for morning coffee or casual gatherings. A formal living room centers around a fireplace, with classic French doors opening into the dining room. The main level also offers exceptional layout flexibility, including a light-filled office with French doors to a private flagstone patio, a cozy den, a family room with a second fireplace, and a practical mudroom with garage access to keep everyday life organized. Upstairs, 4 generous bedrooms include a primary with an oversized bathroom, the rare convenience of a true 2nd-floor laundry room, and a 2nd full bathroom with double sinks. For extra storage, a full walk-up attic provides additional space. Offering rare privacy, incredible space, and enduring quality in a prime location, this exceptional property presents a wonderful opportunity for its next owners to make it their

1951 Burr St, Fairfield
119 Old Dam Rd, Fairfield
$1,175,000
2 Beds ⋅ 2 Baths ⋅ 24163818 MLS
Delightful waterfront oasis offering direct access to Long Island Sound and includes deeded Fairfield beach access. This jewel box home has a bright, open floor plan, fully renovated with a coastal style. The kitchen flows seamlessly to the dining area and living room. Glass doors bring the outside in an lead to a spacious deck and property that culminates at the waterfront and dock. The primary bedroom boasts vaulted ceilings a balcony overlooking the water, providing stunning views of Pine Creek & LI Sound. The property promises breathtaking vistas of coastal sunrises and tranquil sunset views over the salt marsh. Enjoy boating, kayaking, and paddleboarding from your private dock on Pine Creek with access to Long Island Sound. Dont miss the outdoor shower! Directly across the creek is a private association dock at 1702 Fairfield Beach Rd and gated path to access with beach access at 1701 Fairfield Beach Rd. Explore the neighborhood's open space and walking trails, including paths leading to Pine Creek beach. Walk to amenities including beaches, par-3 golf course, and tennis facilities, providing a perfect blend of outdoor recreation and relaxation in a beautiful coastal setting. Minutes to vibrant Fairfield town center as well as scenic Southport village & harbor. Waterfront community 50 miles from NYC offering coastal charm, historic preservation, wonderful dining, shopping & arts.

119 Old Dam Rd, Fairfield
136 Chatham Rd, Fairfield
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 24206592 MLS
There's something timeless about coming home to a classic Colonial on a quiet street, especially w/ nearly half an acre of level, fenced-in yard waiting out back. Set on one of Stratfield's most desirable streets, this home offers space to gather, room to grow & a setting tucked away yet close to everything Fairfield has to offer. Wrapped in cedar shake shingles, the home welcomes you w/ a new roof, energy-efficient windows, bluestone steps & two-bay garage. Inside, abundant natural light pours across red oak floors. The living room centers around a wood-burning fireplace & opens through French doors to a window-lined sunroom/office w/ a vaulted ceiling, backyard views & patio access. The eat-in kitchen offers granite counters, stainless appliances & ample cabinetry, flowing naturally into the formal dining room. The family room w/ built-in shelving creates an inviting space for everyday living & entertaining, w/ a slider directly to the patio & yard. A mudroom & powder room complete the main level. Upstairs are 3 sizeable bedrooms w/ hardwood floors & California walk-in closets, including a primary suite w/ private bath, plus a second full hallway bath. The walk-up attic offers potential for additional bedrooms, guest suite, gym or media room, while the unfinished basement adds more possibilities. Outside, the level .45-acre fenced yard, mature landscaping & generous patio create a private retreat w/ plenty of space to play, dine outside, entertain or explore a future pool.

136 Chatham Rd, Fairfield
150 Sherman Ct Unit 150, Fairfield
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 24197435 MLS ⋅ Sherman Court BLDG.
First time on the market in over 25 years! This exceptional Victorian-style townhouse is tucked away on a quiet cul-de-sac in the heart of Downtown Fairfield, offering timeless character, thoughtful updates, and an unbeatable location. A dramatic two-story foyer with a skylight welcomes you into the spacious living and dining rooms featuring wide-plank wood floors, deep crown moldings, and a marble gas fireplace. The recently updated kitchen offers quartz countertops, glass tile backsplash, and stainless steel appliances, French door slider leads to a private deck overlooking beautifully landscaped patio with a fountain. The expansive primary suite features a vaulted ceiling, marble fireplace, three large closets, and a beautifully renovated ensuite bath with quartz countertops, Kohler fixtures, Waterworks sinks, a walk-in shower, and skylight. The turret guest bedroom also enjoys a vaulted ceiling and private ensuite bath. A flexible bedroom, currently used as a den, a partially finished lower level ideal for a home office or media room add to the home's versatility. Additional features include 26 windows with wood plantation shutters, custom cabinetry, a one-car garage, assigned parking, and beautifully landscaped grounds in an intimate six-unit community. Enjoy the convenience of being moments from Fairfield's restaurants, shopping, Metro-North train station, beaches, parks, and more. A truly special home offering character, quality, and an unmatched downtown lifestyle.

150 Sherman Ct Unit 150, Fairfield
266 Alden St, Fairfield
$995,000
2 Beds ⋅ 1 Baths ⋅ 24207052 MLS
BEST AND FINAL OFFERS BY MONDAY 9/28 AT 5PM. Opportunity awaits in Fairfield's desirable beach area! This Cape Cod sits on one of the neighborhood's larger properties-an impressive .29-acre deep lot in a B Zone-offering exciting possibilities to renovate, expand, or create your dream home. Tucked away on a quiet side street, the location is hard to beat. Enjoy the convenience of walking to the train, Fairfield's vibrant downtown with its restaurants, shops and music venues, as well as a nearby public park, playground and ball field. And, of course, you're just minutes from the beach and all that this sought-after coastal community has to offer. With its generous lot size, desirable zoning and exceptional location, this property presents a rare opportunity to create something special while enjoying the best of the Fairfield beach-area lifestyle.

266 Alden St, Fairfield
97 Wampus Way, Fairfield
$900,000
3 Beds ⋅ 3 Baths ⋅ 24207555 MLS
MULTIPLE OFFERS RECEIVED. OFFER DEADLINE MONDAY, 10/5/26 at 6 PM. Live where the lake is part of everyday life. This Lake Hills home sits just a short walk from private beach access, with canoeing, paddle boarding, and kayaking right at your fingertips. This 3-bedroom, 3-full-bath home offers 3,181 square feet of finished living space across two levels, with a layout designed for both everyday comfort and entertaining. The expansive kitchen is a chef's dream, featuring Sub-Zero, Bosch, and Dacor appliances and custom cabinetry, with easy flow to both the outdoor deck and a generously sized family room. The family room brings in wonderful natural light and offers loads of built-in storage (complete with a ladder for those top shelves), plus a double-sided fireplace connecting to the dining room. Rounding out the main floor is a large bedroom, full bath, and office space, giving you flexible rooms ready to fit your needs. Upstairs, the primary bedroom offers two walk-in closets, a private balcony, and a large en-suite bath. There is also a second bedroom with full bath. Downstairs, the basement includes a workshop and abundant storage which is great for projects or extra space to make your own. Outside, you'll find a large deck and almost half an acre offering plenty of room to garden, play, and enjoy the outdoors. Located less than 5 minutes from the shops and restaurants of Black Rock Turnpike, this is a wonderful opportunity in a sought-after neighborhood.

97 Wampus Way, Fairfield
111 Casmir Dr, Fairfield
$765,000
3 Beds ⋅ 2 Baths ⋅ 24205398 MLS
The neighborhood you've been waiting for and an opportunity that is increasingly hard to find in Fairfield. Set on an oversized lot backing to Fairchild Wheeler Golf Course, this mid-century ranch offers a remarkable blend of location, privacy, character, and possibility. Mature trees and plantings surround the property, creating a park-like setting that feels unexpectedly secluded while still being close to Fairfield beaches, live music, dining and shopping. Inside, more than 1,700 square feet of inviting living space is waiting to welcome you. Beautiful hardwood floors extend through most of the home and built-ins in the living room add to its charm. The kitchen offers ample space to dine while enjoying peaceful backyard views. Just off the foyer and kitchen is the family room which may become your favorite place in the house. A wood-burning fireplace with stone surround anchors the space, while more oversized windows frame the beautiful backyard. The home offers three bedrooms and two full baths. The primary br includes its own newly refreshed bath. The second full bath is a wonderful nod to the home's original character, with beautifully preserved pink tile paired with updated wallpaper and lighting for a look that feels playful and completely at home here. The unfinished basement offers untapped potential to those who may want more space. For buyers who have been waiting for the right combination of location, land, livability and value 111 Casmir is a must see.

111 Casmir Dr, Fairfield

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