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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

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

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

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

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

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

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

55 Morehouse Dr, Fairfield
$1,499,900
24216564 MLS
A unique opportunity awaits in one of Fairfield's most desirable areas, conveniently located near the beautiful Lake Mohegan. This offering includes three adjacent building lots totaling 1.99 acres, presenting an exceptional opportunity for builders, developers, investors, or buyers looking to secure land in a sought-after location. 85 and 105 Morehouse will also convey at closing. Preliminary design plans are available, offering a valuable head start for those looking to explore the property's potential. With preliminary work already completed, buyers may have minimal additional due diligence to perform; however, all plans, approvals, permits, zoning requirements, and development possibilities must be independently verified by the buyer.The property is being sold AS IS, with buyers responsible for completing all due diligence in advance of submitting an offer. Access to the existing home is permitted by appointment. Please do not walk the lots without a scheduled appointment. Opportunities to acquire three contiguous lots in this desirable Fairfield location are rare. Bring your vision and explore the possibilities!

55 Morehouse Dr, Fairfield

173 Puritan Rd, Fairfield
$1,499,000
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

121 Old Post Rd, Fairfield
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 24215183 MLS
Classic charm meets modern living in this beautifully renovated home, completely transformed down to the studs in 2018. Thoughtfully designed with an open, flexible floor plan, stylish finishes, and custom details throughout, this home offers the perfect blend of character and functionality. An inviting foyer welcomes you into the spacious main level, featuring a living room with a gas fireplace and wood shiplap detailing that flows seamlessly into the dining area and stunning kitchen. Highlights include quartz countertops, a breakfast bar, center island with storage, stainless steel KitchenAid appliances, and a custom built-in dining nook. A versatile office/playroom and powder room complete the first floor. Upstairs, you'll find three bedrooms, including a beautiful primary suite with two walk-in closets and a luxurious bathroom featuring an oversized shower. The finished third floor offers flexible space for a fourth bedroom, bonus room, or home office. The lower level provides dedicated laundry and gym areas. Outside, enjoy a private backyard retreat with a paver patio, whole-yard irrigation, and plenty of space for entertaining and relaxation. A wonderful combination of timeless appeal, thoughtful updates, and effortless everyday living!

121 Old Post Rd, 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

250 Szost Dr, Fairfield
$1,489,999
5 Beds ⋅ 5 Baths ⋅ 24205742 MLS
FALL in love with this new home sitting proudly on a beautiful tree-lined circular street in the exceptional Fairfield University area. A covered Front porch greets you, with a sleek metal roof providing not only curb appeal but durability. Plenty of room to sit, sip, and enjoy the neighborhood. Upon entering this 5 Bedroom home, you instantly are comforted by the neutral tones and natural light that spills in. The comfortable living room flows seamlessly into the kitchen, natural hardwood flooring throughout and a gas fireplace offers a cozy spot on a chilly evening At the heart is the custom Kitchen designed for serious cooking and effortless entertaining. The kitchen features Thermador appliances an oversized island topped with gleaming white quartz and a walk in pantry. The adjoining dining area includes a dry bar and beverage cooler with sliders that lead to expansive deck overlooking the fenced in private yard. An optional first floor bedroom and full bath are located off the dining area, a laundry room competes this main level. Upstairs the primary suite is a true retreat with spa inspired bath, soaking tub and generous walk in closet. Two more spacious bedrooms with full bath complete this level. The third floor Bonus room is yours to design..Rec room, music, office? A Full bathroom and Fifth bedroom live on this 3rd level. Just in case you need more space, the entire lower level is finished with half a bath. Efficient mechanicals provide for lower cost utility costs

250 Szost Dr, Fairfield

50 Judges Hollow Rd, Fairfield
$1,475,000
4 Beds ⋅ 3 Baths ⋅ 24215458 MLS
Nestled among 3.56 acres of beautiful woodlands, this classic four-bedroom Dutch Colonial offers an inviting blend of timeless character and comfortable living. Enjoy tranquility with easy access to all that Fairfield has to offer. There are hardwood floors throughout, a welcoming foyer, a large living room with fireplace, and sliding doors that lead to an amazing screened porch surrounded by nature, making it the perfect spot for your morning coffee. An updated kitchen and spacious dining room with doors leading to a private patio are perfect for entertaining. Completing the main level are an office and half-bath. Upstairs you will find four bedrooms, two bathrooms, and a large bonus room. The lower level has a recreation room and plenty of storage. Be sure not to miss the two-story barn on the property. It's perfect for the animal enthusiast or as extra space for creative projects and hobbies. It even has a second story that can be transformed into a home office-or just a cool place to hang out! This home is a must see; a real stunner.

50 Judges Hollow Rd, 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

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

285 Primrose Ln, Fairfield
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 24217107 MLS
Welcome to 285 Primrose Ln, a stunning 2024 total renovation where modern luxury is paired with an incredible location near the sandy beach and splash pad of Lake Mohegan. From the moment you step inside, the new wide-plank white oak floors with a chic Bona Nordic finish set a tone of effortless, timeless style. The heart of the home is the sun-drenched, eat-in kitchen that flows naturally into the main living area, making it a breeze to move from morning coffee to evening relaxation. For those larger gatherings, the great room impresses with soaring vaulted ceilings and new remote-controlled blinds, while the formal living and dining rooms provide elegant spaces for hosting. Every detail has been thoughtfully updated, including custom trim throughout and a primary suite featuring a spa-like bath with a large walk-in shower and double vanity. The hallway bath is equally inviting, equipped with an extra-deep soaking tub. Practicality meets versatility on the lower level, which offers a spacious mudroom off the garage and a finished flex space-perfect for a home office, gym, or creative studio. Outside, the brand-new Trex deck, fresh driveway and thoughtful garden plantings add to the home's curb appeal and ease of living. Located just moments from the scenic Cascades hiking trails and a quick drive to local shopping and dining, this home offers the perfect balance of recreation and convenience.

285 Primrose Ln, Fairfield

43-45 Helen St, Fairfield
$1,299,000
7 Beds ⋅ 3 Baths ⋅ 24217125 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.

43-45 Helen St, Fairfield

160 Brookview Ave, Fairfield
$1,199,000
4 Beds ⋅ 3 Baths ⋅ 24210478 MLS
Perched at the top of the hill on a quiet dead-end cul-de-sac, this meticulously updated 1920s Colonial offers the charm and character that simply cannot be replicated today. A gracious foyer with custom moldings and professional lighting showcases the stunning staircase. To the left, the formal dining room; to the right, a living room with fireplace that opens to an additional family room. Off the dining room is a thoughtful mudroom addition features a brick floor, custom built-ins, designer lighting. A classic butler's pantry leads to the kitchen, complete with a food pantry, half bath, and a collectible antique stove that is a true showpiece. Upstairs, the primary bedroom and two additional bedrooms are all generously sized with high ceilings and abundant natural light, served by a full bath and a custom walk-in closet. There is also the option to create direct access to the bath from the bedroom. The fully finished third floor offers remarkable versatility, with a bedroom, an updated full bath with stall shower, and a spacious playroom or hangout area, easily converted into a private primary suite. The lower level includes a finished room ideal for a home office. Outside, enjoy a slate patio, fenced backyard, and garage. Throughout, you will find gorgeous decor, custom designer lighting, endless custom millwork, and designer hardware. A spectacular home that will not last. A must see!

160 Brookview Ave, Fairfield

28 Country Road Unit 28, Fairfield
$1,199,000
4 Beds ⋅ 4 Baths ⋅ 24153694 MLS
A lifestyle you can truly enjoy at an unbeatable price for new construction in Fairfield's university area. Perfect blend of luxury, select finishes and custom cabinetry create a warm and inviting home. White oak flooring grounds you while natural light spills in through large windows. The kitchen blends seamlessly with the open floor plan, the large island is the main focal point which provides plenty of seating with glamorous waterfall-style quartz countertops. You can customize your dining nook or keep the dining area centered. Cozy up on a chilly night and relax by the fireplace. A modern half bath and mudroom area complete the main level. The primary suite is located on the 2nd floor and features a sophisticated luxurious shower, large soaking tub and wood-fluted double vanity. Walk in closet with custom features. The 2nd and 3rd bedrooms are in tandem with a full bathroom, private bath/shower and elegant double vanity. 3rd floor features private quarters with yet another full bath. Currently set up as an office, this space is versatile. A closet and storage room finish this level. Bonus finished space in Lower level THERE ARE NO HOA FEES HERE! Mere stone's throw from Holland Hill School. 5 miles of sandy shores. 1 mile to Fairfield University. Effortless access to community and culture in vibrant downtown Fairfield. Dining and shopping all within close proximity. Easy commute to NYC. Quality craftsmanship and low maintenance. Private fenced yard. City sewer & water.

28 Country Road Unit 28, Fairfield

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