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79 Fairfield Pl, Fairfield
$1,950,000
5 Beds ⋅ 4 Baths ⋅ 24174341 MLS
Set on a level and flat .24-acre lot in the highly sought-after Sasco Hill area of Fairfield, this charming home offers endless opportunities to customize and create your dream living space. Boasting 2,500 square feet of versatile living area, 5 bedrooms- 2 Primary (one w/ full bath, both upstairs), bedroom on main floor, plus 3 full unfinished basements (could easily be finished), a deck, and an outdoor shed. This property perfectly balances comfort and potential. Enjoy unique dual-street frontage, enhancing privacy and offering multiple access possibilities. The fabulous location is walkable from Southport Harbor, Southport Center & train, 10-15 minute walk to Fairfield downtown & train, 5 beaches plus South Benson marina, golf & award winning schools! Equipped with town water, town sewer, and oil heat, this home provides the perfect foundation for your next chapter in one of Fairfield's most desirable neighborhoods. Don't miss the chance to make this wonderful property your own, combining convenience, space, and endless potential in the heart of Sasco Hill.

79 Fairfield Pl, Fairfield

60 Bridle Trl, Fairfield
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 24202150 MLS
Classic Greenfield Hill Colonial located in desirable Galloping Hill neighborhood. Wonderful turn-key home has been gently lived in and boasts Formal Living Room with wood burning Fireplace & Formal Dining Room with coffered ceiling and Butler's Pantry. Light-filled Kitchen with new backsplash & Quartzite counter tops offers good space for cooking & entertaining. Laundry Room and Powder Room are located off Kitchen. Family Room with its wood burning Fieldstone Fireplace features roomy space and opens nicely out to refreshing blue slated Patio. Home Office is located on Main Level. Beautiful mill work greets you as you ascend the staircase to the Upper Level. Spacious Primary en-suite Bedroom, en-suite 2nd Bedroom, plus 2 additional well-proportioned Bedrooms and Hallway Bath complete the 2nd Level. Walk-up Attic provides excellent storage. Partially finished walk-out Basement (784 sq ft) offers work out space & space for children to play. Basement with add'l 1,134 unfinished square footage provides opportunity & abundant storage space. Insulated 600 sq ft space located above 3 car Garage could make ideal Bonus Room. Plenty of shopping & dining on either Black Rock Tpk or Downtown Fairfield. The wonderful coastal community of Fairfield boasts 5 scenic beaches. 60 Bridle Trail is an excellent & welcoming family home just minutes to the Merritt Pwy, 10 minutes to I-95, train and downtown.

60 Bridle Trl, Fairfield

125 Coleman Rd, Fairfield
$1,894,500
4 Beds ⋅ 4 Baths ⋅ 24205547 MLS
Sophistication meets the warmth and ease of Fairfield living in this exceptional new-construction residence. Offering approximately 4,500 square feet of beautifully finished living space, this custom 4-bedroom, 3.5-bath home pairs clean architectural lines and warm natural materials with a layout designed for both everyday comfort and effortless entertaining. At the heart of the home, the designer kitchen features custom cabinetry, a premium Thermador appliance package, an oversized island, a dedicated bar area, and a fully equipped walk-in pantry with a prep sink. Select-grade white oak flooring and ceilings of nine feet or higher create a bright, airy flow throughout the home. The spacious living room is anchored by a gas fireplace, while a dramatic 10-foot bifold door creates a seamless connection to the covered porch and private, fully fenced, level backyard-with room for a pool. Upstairs, vaulted ceilings bring striking architectural character to the expansive primary suite and Jack-and-Jill bedrooms. Each bedroom offers direct access to a full bath and its own custom walk-in closet. The finished lower level adds exceptional flexibility for recreation, fitness, a home office, or guest accommodations. Set on a quiet neighborhood street just moments from Lake Mohegan, neighborhood parks, shopping, and the Merritt Parkway, this thoughtfully designed home delivers elevated style, exceptional craftsmanship, and the very best of modern living.

125 Coleman Rd, Fairfield

2177 Cross Hwy, Fairfield
$1,875,000
4 Beds ⋅ 5 Baths ⋅ 24211474 MLS
This light-filled contemporary work of art is a unique find in an unmatched setting, pairing privacy and peacefulness with modern functionality and a convenient location. Set back 500 feet from Cross Highway, where Fairfield meets Westport, the long lighted driveway takes you past a serene pond, filled with turtle and frequented by egrets, a nature preserve to enjoy from the elevated deck while drinking morning coffee or watching the sunset. The 4,000 sq ft living space, set on 2.75 acres, offers a much larger canvas given over to 22 ft ceilings and large windows that bring the outside in. Extensively renovated over the past 2 years, the home is ready for your personal touches, with a long list of new bathrooms, new roof, a re-imagined front entrance with custom metal roof and stately steps to a bluestone platform and sitting walls of granite. The first floor primary suite boasts a large WIC with large spa bathroom, with sliders that open to a new bluestone patio, free form pool and tennis court. The round room is a private family room, with custom barn door, off the large open-plan living room. A beautiful spiral staircase takes you to the large round bedroom, ensuite, and over to the twin bedrooms and jack and jill bathroom. All new baths. New large tiger wood deck 10x22' leads from the twin rooms directly to the pool. A Chef's kitchen awaits up a few steps to the dining area and a deck off the kitchen with new trek flooring, turning the kitchen into an entertainment hub.

2177 Cross Hwy, Fairfield

448 Pequot Ave, Fairfield
$1,799,000
2 Beds ⋅ 3 Baths ⋅ 24213940 MLS
Historic 1834 farmhouse located in the heart of Southport Village. From the moment you walk through the door you will feel like you are home. Thoughtful renovation of its iconic Pequot Avenue location in 2016 earned the Southport Conservancy Recognition for Restoration. The foundation was completely rebuilt and the home was elevated to FEMA height regulations. All new plumbing and electrical systems were installed. The original wide plank floors, brick and beams were restored to create an inviting open concept. Professionally designed gardens provide beauty and privacy in the outdoor spaces. A rare opportunity to be just steps away from charming Village shops, Southport Harbor and Metro North. This home offers everything from beauty, convenience and warmth. Welcome Home. Listing agent is related to seller.

448 Pequot Ave, Fairfield

615 S Pine Creek Rd, Fairfield
$1,799,000
4 Beds ⋅ 4 Baths ⋅ 24192571 MLS ⋅ South Pine Creek Duplex BLDG.
Customize your own beautifully crafted new construction in Fairfield's highly desirable Sasco Hill/South Pine Creek neighborhood, perfectly positioned between town and the beach. Enjoy an exceptional lifestyle just minutes from Pine Creek and Sasco Beaches, Southport Harbor, golf, tennis, the train, and Fairfield's vibrant town center-all within approximately one mile or less. Thoughtfully designed and built by respected local builder Associated Development, this home blends timeless architecture with quality craftsmanship and sophisticated finishes throughout. The flexible floor plan is designed for easy licing. The ground level features a garage, spacious mudroom, and a covered loggia that creates the perfect setting for outdoor entertaining. The sun-filled main level offers 9-foot ceilings, a beautifully appointed custom kitchen that opens seamlessly to the living and dining spaces, a welcoming family room with a fireplace and custom built-ins, and a private study ideal for working from home. Upstairs, the serene primary bedroom features a luxurious bath and generous walk-in closet, accompanied by two additional bedrooms. The third floor expands the home's versatility with a fourth bedroom, full bath, and bonus room-perfect for guests, a playroom, fitness space, or media room. Offering the rare opportunity to enjoy brand-new construction in one of Fairfield's most sought-after coastal neighborhoods, this duplex. Act now, still time to customize finishes!

615 S Pine Creek Rd, Fairfield

83 Morehouse Hwy, Fairfield
$1,799,000
5 Beds ⋅ 5 Baths ⋅ 24167698 MLS
Brand-NEW construction Home underway in Fairfield's highly sought-after Lake Mohegan neighborhood, crafted by local builders known for exceptional quality and design. There is still time for buyers to personalize select finishes and create the home of their dreams! Offering over 4,000 square feet of thoughtfully designed living space, this stunning residence is situated on a rare, level .89-acre lot with ample room for a future pool and outdoor oasis. Enjoy an unbeatable location just minutes from Lake Mohegan's beach, walking trails, and recreational amenities, while remaining close to Fairfield's beautiful beaches, Metro-North train service to NYC, award-winning schools, shopping, golf courses, and dining. Designed for today's lifestyle, the open-concept floor plan features 5 spacious bedrooms and 4.5 bathrooms including a fabulous Primary suite and spa like bath, and laundry area; providing exceptional flexibility for modern living. The main level includes a spectacular chef's kitchen, spacious family room with gas fireplace, elegant dining room, and comfortable living areas ideal for both everyday living and entertaining. A finished third-floor bonus space with a full bathroom serves as an ideal fifth bedroom, guest suite, private home office, playroom, or extended family retreat. The lower level offers the option for additional space for a possible: recreation room, gym, media room, or storage. A truly rare combination of: luxury, lifestyle, quality, value, and location!

83 Morehouse Hwy, Fairfield

73 Old Dam Rd, Fairfield
$1,795,000
4 Beds ⋅ 3 Baths ⋅ 24210949 MLS
Vacation living, every day of the year. This move-in ready 4-bedroom home sits on a quiet street in Fairfield's coveted beach area, right on a tidal creek with its own private dock. 73 Old Dam offers the best of both worlds: the magic of waterside living, with Fairfield Beach standing as a natural barrier against the open Sound. Water views throughout, and the upper-level primary suite faces the creek and opens onto a private deck. Sun-filled rooms flow easily for entertaining, and a detached garage adds storage and flexibility. The perfect setting to entertain guests and family inside and out with elevated decks, a larger than expected yard, and a waterside deck to enjoy the sunset. 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.

73 Old Dam Rd, Fairfield

309 Hunyadi Ave, Fairfield
$1,790,000
5 Beds ⋅ 6 Baths ⋅ 24146666 MLS
Set on a cul-de-sac in Fairfield's sought-after University area, this custom-built 5-bedroom, 6-bath residence was originally designed as the developer's own home, with a focus on natural light, architectural detail, and elevated everyday living. The primary suite features soaring 18-foot cathedral ceilings, a custom white oak ceiling treatment, an 11-foot picture window, and a spa-inspired bath. A 300-square-foot covered balcony with 18-foot ceilings extends the living experience outdoors and serves as one of the home's defining spaces. Designed for both entertaining and everyday living, the home includes a gourmet kitchen with Sub-Zero refrigeration, quartzite countertops, custom cabinetry, an oversized island, and a fully outfitted butler's pantry with additional refrigeration, wine storage, a dishwasher, and prep space. Three additional bedrooms offer en-suite baths, while the finished third level provides flexible space for a home office, recreation room, guest suite, or studio. The walk-out lower level offers versatility, with a full bath and ample space for a home gym, recreation room, extended living arrangement, or potential in-law suite. Outside, a flat backyard, mature maple tree, and fire pit create a welcoming setting for entertaining. Combining custom craftsmanship, thoughtful design, and refined finishes throughout, 309 Hunyadi Avenue presents a rare opportunity to own a newly constructed residence in one of Connecticut's most desirable towns.

309 Hunyadi Ave, Fairfield

203 Wildflower Ln, Fairfield
$1,785,000
5 Beds ⋅ 6 Baths ⋅ 24214910 MLS
Nestled at the end of a cul-de-sac in the beautiful Greenfield Hill neighborhood, this newly renovated home sits on a private 2.4-acre lot and offers Fairfield living at its finest. This 5-bedroom home, with four full and two half bathrooms, boasts spacious interiors, an open floor plan, all-new finishes, and a brand-new primary bedroom suite addition above a three-car garage. The exterior is just as stunning as the interior, featuring custom stonework and a fully updated gunite inground pool, ready to be enjoyed this summer. The home offers an effortless indoor-outdoor lifestyle, perfect for relaxing at home or entertaining guests. Move-in ready, 203 Wildflower Lane is the perfect blend of quality, privacy, and location. Brand new property drainage system installed in October 2026.

203 Wildflower Ln, Fairfield

54 Timothy St, Fairfield
$1,749,000
4 Beds ⋅ 4 Baths ⋅ 24213998 MLS
Experience refined luxury in this custom new construction offering 3,264 sqft. of thoughtfully designed living space, situated on a cul-de-sac just moments from downtown Fairfield, premier dining, boutique shopping & beautiful beaches. Step inside to discover exceptional millwork & upscale finishes. The main level features a spacious dining room complemented by a wet bar, perfect for entertaining. The heart of the home is the spectacular eat-in chef's kitchen boasting Thermador appliances, quartz countertops, white custom cabinetry, a white oak center island & an area for a charming breakfast nook. The kitchen flows seamlessly into the family room highlighted by a gas fireplace & sliders leading to a bluestone patio overlooking the private backyard & potential pool site. A mudroom and powder room complete the 1sr floor. The 2nd level offers four generously sized bedrooms, including a luxurious primary suite featuring a spa-like bathroom with a soaking tub, double-sink vanity & a glass enclosed shower. A secondary bedroom enjoys the convenience of a private en-suite bath, while the 3rd & 4th bedrooms share a Jack-and-Jill bathroom with a double vanity and tub/shower combination. A 2nd floor laundry room adds everyday convenience. Additional highlights include a walk-up third level offering the opportunity to create 850 additional sqft. of future finished living space, a lower level with 9 ft. ceilings providing storage or future finishing potential, and a two-car garage.

54 Timothy St, Fairfield

220 Stonewall Ln, Fairfield
$1,700,000
5 Beds ⋅ 4 Baths ⋅ 24184245 MLS
Nestled at the end of a peaceful cul-de-sac, in the highly sought-after Greenfield Hill neighborhood, 220 Stonewall Lane offers a rare opportunity to own a beautifully situated home on 2.07 acres. The expansive outdoor setting provides an inviting space perfect for entertaining or relaxing while enjoying the tranquil surroundings. When entering the thoughtfully planned main level, you are drawn to the large open space with a renovated modern eat-in kitchen, a sitting area with a wood-burning pizza oven, a Great Room with cathedral ceilings, a wood-burning fireplace, and an additional family room with views of the in-ground pool and lush landscaped grounds. Natural light flows throughout. Additional highlights include hardwood floors throughout, large decorative tiles, a formal living room with fireplace, a dining room, walk-up bonus room, laundry and access to the two-car garage. Upstairs, five well-appointed bedrooms include a private primary suite, creating a comfortable and functional area. The unfinished basement offers ample space for utilities, storage and possible recreational activities. Ideally located near Fairfield's beaches, Metro-North, recognized restaurants, and the Fairfield Theatre Company, this private property blends lifestyle, location, and appeal in one of Fairfield's most desirable areas.

220 Stonewall Ln, Fairfield

160 Cedar Rd, Fairfield
$1,699,000
2 Beds ⋅ 2 Baths ⋅ 24205064 MLS
Welcome to 160 Cedar Road, a truly special farmhouse in Southport that has been thoughtfully renovated and reimagined. Filled with warmth, character, and modern updates, this unique property beautifully blends timeless charm with contemporary comfort. Privately set and abutting Aspetuck Land Trust property, the 2-bedroom, possible 3-bedroom, 1.5-bath home enjoys a beautiful natural setting on 4.45 acres while being conveniently close to all that Southport and Fairfield have to offer, including beaches, shopping, restaurants, I95 and the train. The property features a saltwater inground pool, pool cabana, tanning deck, and outdoor shower-creating an exceptional setting for relaxing and entertaining. Three barns, a fenced paddock, and riding ring, along with additional outbuildings and a partially fenced yard, offer tremendous versatility. Rarely does a property combine this much character, thoughtful renovation, privacy, and natural beauty with such a convenient location. 160 Cedar Road is a truly unique property offering a lifestyle unlike any other. Please no driving down driveway without a confirmed appointment- trespassers will be fed to the pigs!

160 Cedar Rd, Fairfield

738 Rowland Rd, Fairfield
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 24200231 MLS
Barely a block from Fairfield Beach this stylish beach house offers bright, designer-chic living with year-round marsh views. The open main level features hardwood floors, a light-filled living area, and a Nantucket-style kitchen with a quartz island and stainless steel appliances. The adjacent dining room leads through French doors to an expanded Trex deck overlooking the marsh. Upstairs, the primary suite boasts a walk-in closet, serene views, and a renovated ensuite bath, alongside two additional bedrooms, a updated full bath, and dedicated laundry. A lower-level mudroom connects to the attached two-car garage and a carved out office space. Highlights include a firepit, outdoor shower, and key upgrades like a new roof, windows, and deck-all just minutes from downtown Fairfield's dining, shops, and train. Gated Beach access awaits you just steps from the house.

738 Rowland Rd, Fairfield

845 Kings Hwy W, Fairfield
$1,645,000
3 Beds ⋅ 3 Baths ⋅ 24207194 MLS
Welcome to 'The Shire', where everyday life feels like a page from a classic New England novel. This enchanting home captures the timeless spirit of Southport, offering a lifestyle defined by character and the best of the gold coast. From the moment you arrive, the lush, mature grounds set a scene of total serenity, on a property anchored by history, all in an unparalleled location. While the aesthetic is pure vintage charm, the dwelling is equipped for modern peace of mind, including a chefs kitchen, updated bathrooms, and a generator to ensure comfort under any circumstance. Original posts and beams, oversized stone fireplaces, wide plank hardwood floors, and designer lighting all complement the warmth and wonder this antique saltbox exudes. The glass-walled greenhouse is a true sanctuary. Whether you're planting or enjoying your morning coffee, it's a space that brings nature near all year long. The grounds include a barn, offering more than just storage. Inside, you'll find two garage bays as well as a dedicated upstairs studio space, perfect for a secluded office, workshop, gym- the options are endless. Every corner of this estate tells a story, from the sun-dappled nooks to the expansive yard that feels worlds away from the hustle and bustle. This isn't just a house; it's a retreat, waiting for its next chapter to begin. If this one of a kind home feels familiar, it's probably because you've been dreaming about the opportunity to live here... and call The Shire yours.

845 Kings Hwy W, Fairfield

88 Springer Rd, Fairfield
$1,599,000
4 Beds ⋅ 3 Baths ⋅ 24214100 MLS
Welcome to this gracious, 4-bedroom center hall Colonial, ideally situated on .61 acres in Fairfield's sought-after lower Greenfield Hill area. Offering 3,421 square feet of living space, plus an additional 600 finished square feet in the lower level, this sun-filled home combines classic details with a comfortable, open floor plan. 9-foot ceilings, 2 fireplaces, hardwood floors and custom millwork add character throughout. The spacious family room features a dramatic floor-to-ceiling stone fireplace and opens to the eat-in kitchen, complete with stainless steel appliances, double ovens and abundant cabinetry. An elegant dining room, living room with fireplace, powder room, and laundry room complete the main level. Upstairs, four generously sized bedrooms include a primary suite with a walk-in closet and an expansive full bath featuring a double vanity, Jacuzzi tub, and separate shower. Three additional bedrooms offer ample closet space and share a full bath with a tub/shower combination. The lower level features a 36 X 15 finished space perfect for a recreation room, playroom, office, media room or a combination of these! A large unfinished area offers abundant storage space. Outside, the fully fenced backyard with bluestone patio offers a private and peaceful setting bordering wooded, town-owned land. Complete with mudroom, attached 2-car garage, full house generator and security system, this move-in-ready home is centrally located to enjoy ALL that Fairfield has to offer!

88 Springer Rd, Fairfield

110 Woodrow Ave, Fairfield
$1,550,000
24187939 MLS
Exceptional development opportunity in Fairfield! Offering approved plans for a new 20-unit multifamily residential community in a highly convenient location. The proposed four-story building features 20 apartments comprised of 12 one-bedroom and 8 two-bedroom units, including 6 designated affordable housing units. Plans include elevator access, covered parking, resident lounge, fitness center, tenant storage, and professionally designed site improvements. A rare opportunity for builders and developers to acquire a shovel-ready project with thoughtfully designed floor plans and modern amenities. Conveniently located near shopping, restaurants, public transportation, I-95, and Fairfield's vibrant town center. Approved plans and supporting documentation available upon request.

110 Woodrow Ave, Fairfield

280 Brookbend Rd, Fairfield
$1,549,000
4 Beds ⋅ 3 Baths ⋅ 24212214 MLS
AN EXTRAORDINARY HOME. AN EXCEPTIONAL LIVING EXPERIENCE IN WINTON PARK. Welcome to one of the most exciting homes to hit the market! Rarely does a home offer such an experience at every turn. From the moment you enter, you are greeted by soaring ceilings, dramatic architectural details, and incredible expanses of glass letting the outside in. This is a home where nature becomes part of your everyday living. Beautifully maintained and thoughtfully updated, this remarkable residence has a fabulously designed kitchen - one you'd love spending time in. An inviting dining room highlighted by a stunning exposed brick accent wall, sets the stage for memorable gatherings and a dining experience that is anything but ordinary. And everyone loves a sunroom! Two separate living spaces each with a stunning architecturally designed fireplace, four generously sized bedrooms including a beautiful en suite primary retreat. And then there is the yard - truly magical! Set on nearly an acre of lush, rolling and level grounds, with a collection of charming outdoor vignettes creates distinct spaces for entertaining, relaxing and gathering with friends. The custom-enclosed garden with water source is a gardeners dream. Every turn there is something to discover, something to appreciate. This is not simply a home to see, it is a home to experience and an experience you won't soon forget.

280 Brookbend Rd, Fairfield

1321 Brookside Dr, Fairfield
$1,500,000
2 Beds ⋅ 2 Baths ⋅ 24210726 MLS
Welcome to The Enchantment, a magical 2.90-acre oasis in the heart of lower Greenfield Hill. Built in 1894, this charming antique farmhouse has been meticulously renovated and expanded to 2,064 square feet, blending historic character with modern comforts. Originally configured with four bedrooms, the home has been reimagined with an open, inviting floor plan and the flexibility to reintroduce a first-floor bedroom with en-suite bath. Gorgeous wood floors, exposed beams and natural wood trim lend warmth and rustic elegance throughout, while the beautifully renovated kitchen serves as the heart of the home. No detail was overlooked, with a new roof, Marvin windows, boiler, electrical, plumbing, kitchen and baths. Outside, meandering pathways weave through enchanting gardens designed by renowned botanist and floral designer Peter Stephens. Discover bubbling fountains, hidden garden vignettes and unexpected places to gather and retreat. An exceptional collection of outbuildings includes the original barn with vaulted ceilings and loft; an adjoining heated gathering studio with wood floors and new skylights; a picturesque three-stall barn with loft, cupola and attached poultry shed; a dedicated workshop barn; and a large storage shed. Each building has been thoughtfully improved, with new roofs throughout and additional updates as needed. The Enchantment is truly a world of its own-a rare combination of historic charm, modern comfort, extraordinary gardens and versatile spa

1321 Brookside Dr, Fairfield

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