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2142-2144 Fairfield Beach Rd, Fairfield
$2,225,000
6 Beds ⋅ 2 Baths ⋅ 24131381 MLS
OPPORTUNITY KNOCKS TWICE - A unique investment awaits with the only two-family home on the Fairfield Beach Road Peninsula featuring private beach access. This fully furnished property offers excellent rental income during the academic season and serves as a relaxing summer retreat for owners-or an additional rental opportunity. Unit 2142 is a spacious four-bedroom residence, each room furnished with a full-size bed; Unit 2144 is a charming two-bedroom creekside unit, each room with twin beds, and private gated access to the beach just across the road. Additional highlights include fresh paint inside and out, a wrap-around deck on the creek side with boat access to Long Island Sound, a convenient laundry room, and an oversized two-car garage with extra storage. Enjoy the best of both worlds-generous year-round rental income and beachside living. Truly, opportunity knocks twice. Owner/Broker

2142-2144 Fairfield Beach Rd, Fairfield

280 Tuckahoe Ln, Fairfield
$2,199,999
6 Beds ⋅ 7 Baths ⋅ 24211148 MLS
Exceptional new construction in the desirable University area, scheduled for completion in Fall 2026. Built by an experienced local builder known for quality craftsmanship and thoughtful design, this impressive home offers 4,709 square feet across four levels, including a walk-out lower level. Designed for modern living, the home features 6 bedrooms, 5 full and 2 half baths. This offers flexibility for guests, home offices, or multi-generational living. The open and functional layout includes a beautifully designed kitchen with a generous walk-in pantry conveniently located between the kitchen and dining room, perfect for entertaining and everyday living. Enjoy seamless indoor-outdoor living with a deck off the kitchen and a patio from the walk-out lower level, offering multiple spaces to relax or entertain. The primary suite is a true retreat, featuring two walk-in closets and a spa-like bath. Additional highlights include a two-car attached garage, impeccable design throughout, and high-end finishes that reflect the builder's commitment to quality. Ideally situated on a quiet street with easy access to downtown, beaches, schools, and shopping, this home offers the perfect combination of luxury, space, and convenience.

280 Tuckahoe Ln, Fairfield

2493 Redding Rd, Fairfield
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 24208162 MLS
Transport yourself back in time in this classic Greenfield Hill colonial! This renovated 1817 stunner offers over 5,000 square feet of living space - complete with private accessory apartment, a light & welcoming sunroom, bucolic barn and amazing gunite pool with waterfall! Mature plantings and trees abound on this spacious, rolling property. A dramatic, two-story front entry with sweeping staircase welcomes you home. Hardwood floors and high ceilings give even more character and elegance to the home. A more contemporary, open floor plan runs throughout the first floor - highlighted by a chef's kitchen, family room and formal dining room (both with fireplaces), living room, den with fireplace, office and more! The primary bedroom suite with elegant bath and walk-in closet punctuates the fantastic second floor, with three additional bedrooms. The home is perfect for hosting parties and overnight guests. An apartment (w/separate entrance) over the garage, an attached three-car garage and charming front porch are further features of this pastoral, private & relaxing home and property. Enjoy everyday or on the weekends! The two-story barn with three stalls and large pasture adds even more to your experience! It has three large stalls - perfect for trail rides - a stone's throw away at The Fairfield Bridle Trails and Brett Woods! Additional riding opportunities at the nearby Fairfield County Hunt Club. Close to Fairfield & Westport shopping, restaurants, entertainment & commuting

2493 Redding Rd, Fairfield

285 Old Dam Rd, Fairfield
$2,100,000
4 Beds ⋅ 3 Baths ⋅ 24212040 MLS
**HIGHEST AND BEST REQUESTED BY MONDAY 10/12 AT 3:00PM.**A Rare Waterfront Retreat. Set along Fairfield's coveted Pine Creek, this 4-bedroom, 2.5-bath home offers a private dock with easy access to Long Island Sound and a relaxed coastal lifestyle. Spend your days boating, kayaking or paddleboarding right from your backyard, then unwind on the expansive deck overlooking the water. Inside, a light-filled, open layout makes the most of the setting, with walls of windows capturing water views throughout the main living spaces. The chef's kitchen features a large center island and opens naturally to the living and dining areas, creating an easy flow for everyday life and entertaining. A spacious bonus/game room with a vaulted ceiling and fireplace is an inviting spot for movie nights, game days or gathering with friends and family. The primary suite enjoys peaceful water views, while three additional generously sized bedrooms offer plenty of space for family, guests or a home office. Outside, the deck with awning extends the living space and provides a natural place for summer dinners and evenings by the water. An additional parcel across the street offers extra parking, recreation space and access to scenic marsh trails. With a private dock, easy Long Island Sound access and a setting designed to be enjoyed inside and out, this is Pine Creek living at its best.

285 Old Dam Rd, Fairfield

79 Fairfield Pl, Fairfield
$2,050,000
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

999 Bronson Rd, Fairfield
$1,949,000
4 Beds ⋅ 3 Baths ⋅ 24209671 MLS
Enchanting Victorian Farmhouse ideally set on 1.25 picturesque acres w/ in-ground heated Pool. Welcome to 999 Bronson Road, where antique living has been remodeled & redesigned eloquently to create a chic modern farmhouse lifestyle. This remarkable historic farmhouse has been lovingly updated while preserving its character & integrity. The inviting wraparound front porch & oversized door greet & welcome you in. Once inside, you will be impressed w/ soaring ceilings, dramatic floor-to-ceiling windows, an abundance of natural sunlight, wide-plank hardwood floors, exquisite millwork, custom built-ins & 3 wood burning fireplaces. Exceptional architectural details include oversized pocket doors, 2 beautifully designed staircases & a wonderful flow from room to room. The thoughtfully designed floor plan offers 9 spacious rooms including 4 bedrooms conveniently located on 1 level, providing both comfort & functionality. Outside, the expansive grounds offer a private & peaceful setting, complete w/ a built-in pool, multiple tiered patios, blooming annuals & a park-like sprawling lawn - ideal for relaxing, entertaining & enjoying the beauty of the property throughout the seasons. Recent home improvements include new fence, new whole house generator, interior & exterior freshly painted, new walk way, newer roof & converted from oil to gas making this home maintenance free. Close to Fairfield & Southport town center, train, school, parks & beaches. This home feels like a warm embrace.

999 Bronson Rd, 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

73 Old Dam Rd, Fairfield
$1,875,000
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

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

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

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

173 Puritan Rd, Fairfield
$1,575,000
3 Beds ⋅ 1 Baths ⋅ 24174169 MLS
Located in the highly desirable beach area of Fairfield, this charming and beautifully maintained 3-bedroom Cape, situated on a corner lot, offers the perfect blend of classic character and modern convenience. The newly remodeled eat-in kitchen features granite countertops and stylish finishes throughout. Enjoy entertaining in the formal dining room with beautiful built-in hutches or relax in the inviting formal living room with a cozy wood-burning fireplace. Hardwood floors run throughout the home, adding warmth and timeless appeal. A cozy family room with sliders opens to the private yard, perfect for indoor-outdoor living and entertaining. Just a short walk to beautiful Jennings Beach, shopping, restaurants, train, and more, this home offers the ideal coastal lifestyle in an unbeatable location.

173 Puritan 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

250 Szost Dr, Fairfield
$1,549,999
5 Beds ⋅ 5 Baths ⋅ 24205742 MLS
A charming covered front porch, with a striking metal roof welcomes you home and offers the perfect spot to relax and enjoy the neighborhood. Upon entering the open floor plan you are instantly attracted to the custom kitchen designed for entertaining and cooking with the center of attention the massive island with quartz countertop. Calming neutral tones soothe the soul. High end Thermador appliances add to the cooking coinsures dream. A walk in pantry to organize all your items and gadgets. The dining area features a stylish dry bar and beverage cooler. Beautiful oak flooring & a gas fireplace compliments the sitting area. Main level also offers a versatile bedroom and beautifully appointed full bath, ideal for guests, a home office, or a possible in-law suite. Upstairs, the spacious primary suite is a true retreat with a spa-inspired bath, soaking tub, and generous walk-in closet. With 5 bedrooms plus a 3rd floor bonus there is flexibility HUGE TV REC SPACE office space, Guest rm. The finished lower level expands the living space with a convenient half bath and room for a recreation area, home gym, media room, or whatever suits your lifestyle. Expansive sliders open to a massive deck overlooking the private backyard-perfect for outdoor dining, entertaining, or simply enjoying the setting. A white privacy fence sounds the property and creates a wonderful sense of seclusion. Your dog will love it ! Included a garden shed and garage with plenty of driveway parkin

250 Szost Dr, 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

265 Autumn Ridge Rd, Fairfield
$1,495,000
5 Beds ⋅ 3 Baths ⋅ 24210815 MLS
Welcome to 265 Autumn Ridge Road-a beautifully updated Fairfield home where stylish interiors, exceptional flexibility and an impressive outdoor setting come together with ease. At the heart of the home is the fully renovated kitchen, completed in 2022 with an eye for both beauty and function. Thoughtful details, quality finishes and a polished design make it a natural gathering place, whether you're preparing a quiet dinner or entertaining a crowd. The outdoor spaces are equally impressive. A recently completed deck expansion opens to a new patio and overlooks a beautifully leveled yard enhanced by a retaining wall and new sprinkler system. The seller plans to paint the deck within the next few weeks, offering the buyer an opportunity-depending on timing-to select a color that complements their personal taste. A brand-new fence, completed in 2026, surrounds the property, creating a private and inviting setting for outdoor dining, entertaining, play and relaxation. Inside, the primary bathroom was updated and the hardwood floors were refinished in 2022, adding warmth and a fresh, polished feel throughout the home. A new picture window, installed in the living room in 2024, fills the space with natural light and frames a lovely view of the property.

265 Autumn Ridge Rd, Fairfield

624 Center St, Fairfield
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 24205674 MLS
SOUTHPORT CHARM, WALK TO EVERYTHING.... Ideally situated in the coveted town of Southport, this custom designer residence offers an exceptional opportunity to enjoy the very best that Southport has to offer. Thoughtfully designed for today's lifestyle to maximize both space, functionality and style, the home features an open-concept main level with seamless living offering gas fireplace, in-ceiling speakers, foyer w/glass staircase, Marvin floor to ceiling windows and KLAR steel doors. The bespoke kitchen features Aurea Stone island & floating display shelf, stainless Bosch appliances, induction range & wine cooler. The second floor is anchored by a fabulous primary suite featuring a custom walk-in closet and a beautifully appointed spa-worthy bathroom with soaking tub. An additional guest bedroom with ensuite bath and a light filled office complete the 2nd level. The 3rd floor loft space offers library/study space with custom built-in bookcases and bedroom with built-in bed. A fabulous light filled home with 6" white oak character hardwood flooring throughout. Work from home or work out at home with the temperature controlled detached office, gym or studio. Plentiful storage and large cedar closet in the finished lower level. Lovely outdoor entertaining space with evergreen privacy hedges, bluestone patio and outdoor speakers and wifi. An enviable location, timeless appeal, and the ease of having everything within reach make this a truly special offering. Agent Owned.

624 Center St, Fairfield

43 Helen St, Fairfield
$1,489,000
7 Beds ⋅ 3 Baths ⋅ 24214094 MLS
An exceptionally rare opportunity in the heart of Fairfield! Completely rebuilt from the ground up, this stunning new two-family home offers the perfect combination of coastal sophistication, modern efficiency, and exceptional investment potential. Tucked into one of Fairfield's few "hidden gem" neighborhoods, the location is everything: steps from Post Road's shopping, dining, and entertainment, with the train station, Fairfield University, and beautiful beaches all within easy reach. Whether you're an owner-occupant seeking supporting rental income, a savvy university investor, or looking to build long-term wealth in one of Fairfield County's most desirable communities, this turnkey property checks every box. Meticulously crafted with low-maintenance shingle-style siding, composite decking, natural white oak hardwood floors, modern shaker cabinetry, quartz countertops, coastal-inspired bathrooms, and recessed lighting throughout. High-efficiency systems include natural gas heat, central air, on-demand hot water, and separate in-unit laundry. Beautiful new landscaping, classic white picket fencing, abundant off-street parking, and sun-filled interiors complete the picture. The first unit features 3 bedrooms, 1 full bath, an eat-in kitchen, living room, and private rear deck. The spacious upper residence spans the second and third floors, with 4 bedrooms, 2 full baths, an eat-in kitchen, living room, and versatile flex space. THE WORK IS DONE! All that's left is opportunity.

43 Helen St, Fairfield

91 Lockwood Rd, Fairfield
$1,448,000
6 Beds ⋅ 4 Baths ⋅ 24199718 MLS
Welcome to 91 Lockwood Road, where modern farmhouse charm meets timeless comfort in one of Stratfield's most sought-after neighborhoods. Beautifully renovated, this exceptional home offers the perfect blend of style, functionality, and everyday living. Designed for today's lifestyle, the home features 5-6 bedrooms, 3 full baths, and 1 half bath, with bright, versatile living spaces that offer both comfort and versatility. Gleaming hardwood floors flow throughout, creating warmth and continuity. The kitchen features white oak cabinetry, a spacious peninsula island with quartz counters, and an adjoining dining area with direct access to the pool-creating an ideal layout for everyday living and entertaining. The second floor is anchored by a spacious primary suite, along with three additional bedrooms. On the main level, one to two additional bedrooms provide exceptional flexibility for guests, a home office, playroom, or den. Step outside to your private, fully fenced backyard retreat featuring a heated saltwater gunite pool and spa. Recently refreshed with new plaster and tile, the pool and spa are enhanced by new equipment and a Wi-Fi automation system. Additional highlights include an oversized one-car garage with exceptional storage.

91 Lockwood Rd, Fairfield

41 Reynolds Dr, Fairfield
$1,399,000
4 Beds ⋅ 3 Baths ⋅ 24212212 MLS
Nestled on a quiet cul-de-sac in Fairfield's sought-after University neighborhood, this timeless Colonial combines the feel of new construction with exceptional character & craftsmanship. Completed in late 2022, this nearly 3,400 SF, 4-bed, 2.5-bath home is filled with natural light & elevated by custom millwork, shiplap, steel railings & thoughtful architectural details. The open first floor features 9' ceilings and a gourmet kitchen w/ custom cabinetry, quartz countertops and high-end appliances, flowing seamlessly to the family room anchored by a gas fireplace. Sliding French doors open to an AZEK deck and manicured, level lawn, creating an ideal setting for indoor/outdoor entertaining & everyday living. A generous dining room, w/ custom built accent wall, is perfect for holidays or casual gatherings, while the spacious, thoughtfully designed mudroom connects directly to the attached 2-car garage. Upstairs, the impressive Primary Suite features 2 walk-in closets, including a custom dressing closet, and spa-like bath w/ soaking tub & glass shower. 3 add'l bedrooms, all w/ walk-in closets, plus a 4-piece hall bath & dedicated laundry complete the 2nd floor. The beautifully finished lower level offers a private home office and flexible recreation/bonus room. An incredibly convenient location ideal for commuters. Walkable to Fairfield Metro, Whole Foods, Jennings Beach, shops and restaurants. Incredible storage, functionality, efficiency and design detail sets this home apart.

41 Reynolds Dr, Fairfield

891 Oldfield Rd, Fairfield
$1,395,000
3 Beds ⋅ 4 Baths ⋅ 24209087 MLS
NEW PRICE. An exceptional opportunity to own this impeccably maintained, beautifully designed home just moments from town and the beach. Better than new. Built in 2018 and enhanced with over $175K in recent custom upgrades, this 3-4 bedroom sophisticated three-story residence offers a level of finish, customization and outdoor living rarely found in new construction. Designer interiors feature elevated materials throughout, including a beautifully appointed chef's kitchen and thoughtful custom details. The third-floor flex space offers exceptional versatility for a home office, gym plus guest space or fourth bedroom, with a full bath and additional storage. Outside, lush professionally designed gardens create a private setting with a generous entertaining patio and custom built gas firepit, all backing to beautiful open marshland and nearby walking trails. Ideally located walk/bike to beach and vibrant town center, this impeccable move right-in home combines the look and quality of new construction with the individuality of a custom-built residence. Part of an intimate two-unit condominium on .25 acres lot. The homes share no walls and are connected only by their garages, giving this residence the privacy and feel of a single-family home. No HOA fees. Owners of the two units only share the cost of master insurance policies and certain maintenance expenses.

891 Oldfield Rd, Fairfield

891 Oldfield Rd, Fairfield
$1,395,000
3 Beds ⋅ 4 Baths ⋅ 24207361 MLS ⋅ Oldfield Commons BLDG.
NEW PRICE. An exceptional opportunity to own this beautifully designed, impeccably maintained home just moments from the beach and town. Better than new. Built in 2018 and enhanced with over $175K in recent custom upgrades, this 3-4 bedroom sophisticated three-story residence offers a level of finish, customization and outdoor living rarely found in new construction. Designer interiors feature elevated materials throughout, including a beautifully appointed chef's kitchen and thoughtful custom details. The third-floor flex space offers exceptional versatility for a home office, gym plus guest space or fourth bedroom, with a full bath and additional storage. Outside, lush professionally designed gardens create a private setting with a generous entertaining patio and custom built gas firepit, all backing to beautiful open marshland and nearby walking trails. Ideally located walk/bike to beach and vibrant town center, this impeccable move right-in home combines the look and quality of new construction with the individuality of a custom-built residence. Part of an intimate two-unit condominium, the homes share no living-space walls and are connected only by their garages, giving this residence the privacy and feel of a single-family home. No HOA fees. Owners of the two units only share the cost of master insurance policies and certain maintenance expenses.

891 Oldfield Rd, Fairfield

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