Fairfield Real Estate

Welcome to Fairfield, Connecticut – a charming coastal town that perfectly blends suburban tranquility with vibrant community life. Nestled in Fairfield County, this picturesque town boasts a rich history, beautiful landscapes, and an array of amenities that make it an ideal place to call home.

Fairfield is renowned for its stunning beaches, with over three miles of coastline along the Long Island Sound. Residents and visitors alike enjoy the sandy shores of Jennings Beach and Penfield Beach, perfect for sunbathing, picnicking, and water sports. The scenic waterfront also provides a backdrop for various community events and festivals throughout the year, fostering a strong sense of community among locals.

The town is also home to a diverse selection of parks and recreational facilities, including the expansive Lake Mohegan Park, where families can hike, fish, and enjoy nature. With a strong emphasis on outdoor activities, Fairfield encourages an active lifestyle, making it easy to stay fit and connected with nature.

Fairfield’s thriving downtown area is a hub of activity, featuring a delightful mix of boutique shops, restaurants, and cafes. Whether you’re in the mood for a casual dining experience or a night out at a trendy eatery, there’s something to satisfy every palate. Additionally, the town’s strong educational system, with highly-rated public and private schools, ensures that families have access to quality education.

With its charming neighborhoods, rich cultural scene, and convenient access to major cities like New York and New Haven, Fairfield offers the perfect blend of small-town charm and urban convenience. Come discover why so many are proud to call this vibrant community home!

Newest Listings in Fairfield

$1,161,500

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24206575 MLS

Totally refreshed with many new improvements including a stunning kitchen island, this mid-century modern classic home is tucked away at the end of a wide, welcoming cul-de-sac in the heart of Greenfield Hill. Spanning 5,000 sq ft with 4/5 bedrooms and 4 updated full baths, this beauty is set on 2 sprawling, private acres. A prime feature is the breathtaking great room w/soaring 12ft+ ceilings and a dramatic wall of glass. The formal dining room has 9ft ceilings and a bank of floor-to-ceiling windows. The island kitchen with large walk-in pantry has been expanded and is outfitted with newer 2024 top-tier appliances. The adjacent sun room is perfect as a casual eating area and is drenched with sunlight through the two walls of windows. Another main floor feature is a flex room, boasting its own full bath and walk-in closet, ideally suited as either an in-law suite or family room. Retreat to the main floor primary bedroom suite with an updated full bath & an oversized walk-in closet. 3 additional good sized secondary bedrooms round out this spacious and well designed home. Outside, the expansive deck allows you to take in the lush, private grounds. Car enthusiasts will appreciate the two double-bay attached garages, all accessed via a graceful circular driveway. This tranquil location provides easy access to local boutique shopping, vibrant dining scenes, coastal beaches, and convenient transportation links. Opportunity awaits at 480 Riders Lane!

480 Riders Ln, Fairfield

$3,975,000

5 Beds ⋅ 5 Baths ⋅ COMING SOON Status ⋅ 24206348 MLS

Over an acre to yourself. The best of Fairfield within reach. In the heart of downtown Fairfield and the beach area, 415 Old Post Road offers something almost impossible to find: land and privacy to create a generational estate, with the life of a coastal town just beyond your gate. Only a handful of properties in the Sherman School district offer this. Fewer still could tell this story. The family who built this Italianate Victorian stayed for more than a century. Stand beneath its soaring ceilings, admire the craftsmanship, then step onto the screened-in porch. You begin to understand. Trees surround you. Church bells carry through the air. It feels like your own park. Yet the beach, schools, restaurants, shops and train are all within walking distance. For the current owners, that has meant children walking home from school with friends. Thanksgiving dinners for twenty. Additional bedroom options for overnight guests. Winter evenings around the parlor fire. A front porch filled with friends as the Memorial Day parade passes by. There is room here for the life you have imagined. Explore the possibilities for a pool, tennis court and gardens. Create a place where everyone gathers now-and where the next generation will want to return. Historic architecture. Meticulously maintained, thoughtfully updated and in pristine condition. A once-in-a-lifetime opportunity. Come discover what makes this place so hard to leave-and imagine what the next 50 years could look like.

415 Old Post Rd, Fairfield

$1,049,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24206592 MLS

There's something timeless about coming home to a classic Colonial on a quiet street, especially w/ nearly half an acre of level, fenced-in yard waiting out back. Set on one of Stratfield's most desirable streets, this home offers space to gather, room to grow & a setting that feels tucked away yet close to everything. Wrapped in cedar shake shingles, the home welcomes you w/ a newer roof, energy-efficient windows, bluestone steps & a two-bay garage. Inside, natural light pours across red oak floors. The living room centers around a wood-burning fireplace & flows into a window-lined sunroom/office w/ a vaulted ceiling, backyard views & patio access. The eat-in kitchen features granite counters, stainless appliances & ample cabinetry, while the formal dining room & centrally positioned family room with built-in shelving create an easy flow for everyday living & entertaining. A laundry/mudroom & powder room complete the main level. Upstairs are 3 sizeable bedrooms w/ hardwood floors & outfitted California walk-in closets, including a primary suite w/ a private bath, plus a second full bath for the other bedrooms. The walk-up attic offers exciting potential for additional bedrooms, a guest suite, home gym or media room, while the unfinished basement provides even more possibilities. Outside, the level .45-acre fenced yard, mature landscaping & generous patio create a private retreat w/ plenty of room to play, entertain, dine outside or explore a future pool.

136 Chatham Rd, Fairfield

$2,299,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24206534 MLS

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

446 Wormwood Rd, Fairfield

$999,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24206480 MLS

The home you have been waiting for! Offered at $999,900, this beautifully updated 4-bedroom, 3-bath split-level offers more than 2,600 square feet of finished living space on a spacious 0.62-acre lot with a 1-car attached garage ideally situated on a quiet cul-de-sac. Extensively renovated, the home features hardwood flooring, a remodeled kitchen with granite countertops high-end appliances, beautifully updated bathrooms, newer upper-level windows, heating and central air conditioning, updated lighting and driveway. The finished lower level includes a family room and office, along with additional flexible living space ideal for whatever best suits your lifestyle. Permitted improvements include kitchen and bath renovations, HVAC, plumbing, electrical work and replacement windows, offering buyers added confidence in the quality of the upgrades. The outdoor space is equally impressive. Enjoy a large private yard with an above pool, expansive deck and plenty of room for entertaining, relaxing and enjoying indoor-outdoor living. A storage shed provides additional space for pool equipment, landscaping tools and seasonal items. Located in desirable Fairfield, residents enjoy a vibrant coastal community with beaches, restaurants, shopping, recreation and convenient access to train and major commuting routes. With extensive renovations, a private pool, generous lot and desirable cul-de-sac setting, this property offers the space and Fairfield lifestyle buyers are looking for.

73 Weeping Willow Ln, Fairfield

$1,925,000

4 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 24206227 MLS

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

550 Wellington Dr, Fairfield

$1,450,000

4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24205655 MLS

Set on 2.46 picturesque acres in coveted Greenfield Hill, this modernized farmhouse Colonial combines classic character, thoughtful updates and an exceptional piece of property. Beautiful stone walls frame expansive open lawns, while a newer front porch with copper roofing adds to the home's timeless farmhouse appeal. Just under 3,000 SF of above-grade living space features hardwood floors, detailed millwork, multiple fireplaces and a wonderfully flexible floor plan. The remodeled kitchen is the heart of the home w/ quartz counters, large center island, custom cabinetry and a high-end appliance package including Sub-Zero & Wolf. An adjacent wet bar with wine refrigeration is ideal for entertaining. The kitchen opens to a spacious living area anchored by a dramatic fieldstone fireplace. A formal dining room w/ fireplace and separate family room with vaulted ceiling and exposed beams. A standout feature is the main-level in-law potential: private entrance, bedroom, bonus room / access to a full bath-ideal for guests or an au pair. Upstairs are the spacious primary bedroom, 2 additional bedrooms and full bath. Outside, a stone patio & covered porch overlook the home's incredible grounds. Broad, field-like lawns, mature trees and extensive stonework create a true estate setting-a remarkable property to enjoy for decades to come. New roof / gutters in '26. A special Greenfield Hill home combining modern updates, versatile living space and a property that is truly unforgettable!

1835 Cross Hwy, Fairfield

$599,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205792 MLS ⋅ Sunshine BLDG.

Very clean and move-in ready! 70 Sunrise offers turnkey townhouse living easily accessible to all of Fairfield and beyond This beautifully maintained 4-bedroom, 2.5-bath home stands apart with thoughtful renovations, substantial upgrades, and an exceptionally private location. Hardwood flooring runs throughout the home. At the center of the home is an upgraded kitchen that provides abundant storage and functionality. Renovated cabinetry, deep beautiful countertops, and newer stainless steel appliances create a polished and practical space ideal for everyday living and entertaining. Off to the right of the kitchen is a spacious first floor bedroom with full bath ensuite perfect for guests!The spacious living room features a cozy fireplace and opens directly to a private deck that has been updated with trexx flooring. The deck is a wrap-around style that is an inviting extension of the living space for relaxing or entertaining outdoors. A large divider to the left maintains privacy and the view opens to a large side yard that is absolutely stunning at view. Upstairs hosts 3 generously sized bedrooms with a conveniently centered bathroom that has been newly renovated and meticulously designed! The fully finished lower level with half bath and walk-out offers incredible flexibility-ideal as a sleek home office, cozy media room, or ultimate hangout space. With smart design and stylish touches throughout, this home is easy to live in and a commuter's delight! With many of the

70 Sunrise Ave Unit 70, Fairfield

$629,000

4 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24196770 MLS

Traditional on the outside and surprisingly spacious on the inside, this University cape is freshly updated and is ready for its next owners. A sun-filled living room welcomes guests a it features a bay window and gleaming hardwood floors which extend throughout bedrooms on the main and upper levels. A total of four bedrooms ( two on the main level and two upper) feature potential dining and home office use. Refreshed kitchen with stainless steel appliances, subway backsplash, two full bathrooms are in move-in ready condition. A breezeway, mud room links the attached garage for all weather coverage. A full walk-out basement leads to a private patio and peaceful back yard. The generous sized lower level also includes a washer/dryer, extra refrigerator, workshop and space for a possible home gym and additional storage. Ideally located minutes from town, medical facilities, two train stations, schools, shopping, Merritt and I-95.

438 High St, Fairfield

$899,900

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205504 MLS

Welcome to this beautifully cared-for, move-in ready 5-bedroom, 2.5-bathroom home nestled within Fairfield's distinctive Dover Park neighborhood. The main level offers a comfortable and inviting layout with a spacious living room, dining room, kitchen, and welcoming family room. The family room features a beautiful brick wall and wood-burning fireplace, creating a warm setting for relaxing, entertaining, and spending time with family and friends. Two additional bedrooms are conveniently located on the main level near a full bathroom. Upstairs you will find three spacious bedrooms, including a generously sized primary bedroom with a walk-in closet, plus two additional bedrooms.Storage will never be an issue, thanks to a pull-down attic and a full, unfinished basement. These spaces provide ample room for storage, hobbies, a workshop, or future possibilities.Outside, the property truly shines.The spacious, flat backyard is surrounded by mature trees and beautifully established landscaping, creating a private and tranquil outdoor retreat.A distinctive natural rock outcropping adds character and a unique sense of place, while the generous deck provides an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings.Recent improvements add to the home's appeal and peace of mind: a new roof (2026), new driveway (2025), and radon remediation (2025). Solar panels on the rear of the home provide excellent energy efficiency. Make your appointment today!

37 Stevenson Rd, Fairfield

$869,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205513 MLS

One of the best side street locations in Fairfield's University neighborhood! This updated single family home is so close to all town amenities: the train, center of town, highways and Black Rock Turnpike! Beyond location, this home has newly refinished hardwood flooring and fresh paint throughout offering bright living spaces, lots of storage and a gorgeous fully-fenced in backyard! Just off Mill Plain Rd, this home is on a dead-end side street with open space across the street, a perfect combo offering privacy within a neighborhood setting! Featuring 3 bedrooms, 1.5 bathrooms and many newer features for high efficiency living like new central air in 2025, updated furnace, 200 amp electric, windows, and an updated kitchen with pantry! The main floor has an open floor plan with a large living room, dining room, kitchen and family room. All 3 bedrooms are upstairs along with a full bathroom and large linen closet. The spacious bonus room is a walk-out featuring a half bathroom with laundry and full-size windows for lots of light. Other features include an attached 1 car garage and large deck and pea-stone patio overlooking the flat yard. This home is stunning with a great property, close to everything. What a charming place to call home!

65 Cynthia Dr, Fairfield

$1,495,000

5 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 24205061 MLS

Quintessential New England architecture, extraordinary grounds & an interior that continually surprises define this distinctive Greenfield Hill property. Privately set behind a stone wall on 2 exquisitely landscaped acres, this stately clapboard Colonial is beautifully sited w/cedar roof, cupola, rows of boxwood, bluestone walk & gracious front porch. Inside beautifully appointed rooms unfold w/remarkable versatility, warmth & exceptional flow for entertaining. Gracious living room w/gas fireplace leads to inviting dining room while the sun-filled kitchen overlooks the spectacular landscape & opens through French doors for seamless indoor/outdoor living. Family room w/custom built-ins, window seat & 2nd gas fireplace. Large laundry room & attached 2-car garage complete main level. Upstairs, 5 BR & 3 full BA include a gorgeous en-suite primary. Finished lower level is truly unforgettable: custom Irish Pub inspired by owners' travels to Ireland w/full bar, kegerator, handcrafted details & cozy wood-burning fireplace, creating a one-of-a-kind space for gathering. Outside dine beneath the cedar pergola draped in climbing hydrangea, wander through the English gardens, tend the enclosed vegetable garden, relax in the hot tub, enjoy morning coffee on the garden swing or simply watch nature unfold. Expansive bluestone patios, specimen plantings, mature trees & lush lawns create a setting that feels worlds away. A rare property where beauty, personality & inspired living converge.

3901 Redding Rd, Fairfield

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