Fairfield Connecticut homes for sale starting at Fifty Thousand Dollars

$1,299,000 - Fairfield, CT

868 South Pine Creek Road Fairfield, CT - Fully Renovated South Pine Creek Townhome - Walk to Beach & Town This exceptional 3BR, 2.5BA townhome has been completely transformed with over $300K in upgrades, offering a turnkey lifestyle just 0.5 miles from South Pine Creek Beach. Walk to town, train, restaurants, golf, and tennis. The main level shines with shiplap detailing, refinished hardwood floors, recessed lighting, and a gas fireplace with custom surround. The brand-new kitchen features a full Monogram appliance suite, quartz countertops, and custom cabinetry. All closets have been outfitted with automated lighting and smart cabinet systems for seamless organization. Upstairs, the reimagined primary suite offers a luxurious bath with walk-in shower and double vanity. The second level also includes two additional bedrooms and a beautifully updated full bath. The third-floor bonus space is perfect for a home office, playroom, or additional bedroom. Additional upgrades include a new roof, new window treatments (shutters and blinds), Lutron smart lighting throughout, Ring security system, and an automatic above-ground sprinkler setup. Newly fenced yard with fresh sod creates a private outdoor retreat. A full list of upgrades is available upon request. This move-in ready home combines beach area convenience with elevated modern style.

$1,299,000 - Fairfield, CT

$1,150,000 - Fairfield, CT

96 Cedar Woods Lane Fairfield, CT - "We will see creativity emerge triumphant in the battle of sameness." This historic quote from Victor Civkin the "pioneer of modernism in Connecticut" has never been more true than it is today. If your soul longs to preserve a piece of Mid-Century architectural history while flexing your designer magic this iconic MidMod is waiting. You have over 3,000 sq ft on almost half an acre to work with. Designed by Civkin in 1951 and located among other modernist treasures, 96 Cedar Woods is one of a few remaining homes in Fairfield County designed by the renowned modernist. With an emphasis on spaciousness the floor plan offers 4 distinct levels and a ton of flexibility. You can customize and adapt the spaces to fit your evolutionary needs. The town calls it a 4 bedroom home, however it lives like 5 or 6 bedrooms including one on the 1st floor. The primary living spaces on the main level include a front to back living room with grand windows, a formal dining room, a huge updated kitchen, and a study with a full bath adjoining. Upstairs includes the primary bedroom suite and 2 large bedrooms sharing a full bath. The 3rd floor is a private bedroom suite. The finished LL has a full bath and can be a home office or recreation space. The house sits high atop a hill at the end of the cul-de-sac and the back opens onto a deep, flat back yard with room for a pool. The stone patio, screen porch and oversize 2 car garage round out this distinctive split level design.

$1,099,000 - Fairfield, CT

4665 Black Rock Turnpike Fairfield, CT - Welcome to 4665 Black Rock Turnpike. A beautifully designed and well-maintained 4-bedroom, 3.5-bathroom Colonial home offering nearly 3,500 square feet of elegant living space in one of Fairfield's most convenient locations. Privately set back from the roadway, this home is surrounded by natural beauty, with a stream running through the property and beautifully landscaped grounds providing a serene and picturesque setting. Inside, you'll find a light-filled layout designed for modern living. Sun-drenched rooms, especially the expansive cathedral-ceiling family room with fireplace, are bathed in natural light throughout the day, creating a warm and inviting atmosphere. This stunning family room offers flexible living options and can easily serve as an in-law suite if desired. The kitchen features rich cherry cabinetry, granite countertops, and stainless-steel appliances, flowing seamlessly into both formal dining and living rooms-perfect for entertaining. All four bedrooms are located on the second floor, including a spacious primary suite w/cathedral ceiling, walk-in closet and en-suite bath. The additional bedrooms are generously sized with ample storage. A large unfinished lower level offers more potential, ideal for a home office, gym, playroom, or media center. Recent updates include a full interior repaint, beautifully refinished hardwood floors, and a newly paved driveway. Enjoy peaceful outdoor living with a rear deck that overlooks the tranquil landscape.

$999,000 - Fairfield, CT

1510 Congress Street Fairfield, CT - Nestled on two wooded acres in the coveted Greenfield Hill district, this extensively updated classic center hall colonial is the quintessential New England charmer. Thoughtfully equipped with premium touches, this four bedroom, 2.5 bath home boasts Bosch appliances, custom cabinetry, quartz countertops, hardwood floors throughout, exquisite light fixtures, and a seamless floorplan. All bedrooms are generously sized with spacious closets and the master bedroom features a walk-in closet. An unfinished lower level with 1,128 sq. feet offers expansion possibilities. There is plenty of space in the backyard to add a pool with a pool house. Convenient to Fairfield beaches, lakes, hiking, golf courses, shops, restaurants, and highways, this home provides privacy in an idyllic location. Light and bright throughout, whether it's cozy nights by the fireplace or entertaining family and friends, this is truly a special place to call home.

$999,000 - Fairfield, CT

407 Meadowbrook Road Fairfield, CT - Welcome to 407 Meadowbrook Road - a Charming 1920s Colonial with Modern Upgrades with 5 bedroom, 2.5-bath Colonial nestled in the heart of Fairfield's sought-after University neighborhood. This 2,440 sq. ft. home blends timeless 1920s charm with the comforts and conveniences of modern living. From the inviting front porch to the fenced-in backyard and patio, this home is perfect for both everyday living and entertaining. Inside, the sun-filled living room features built-in shelving and a cozy fireplace, flowing seamlessly into a formal dining room with a classic corner cabinet. The kitchen boasts stainless steel appliances, birch cabinetry, and a breakfast nook ideal for casual meals. Working from home? You'll appreciate the private main-floor office with built-ins and a skylight, creating a productive and peaceful workspace. A spacious family room offers views of the backyard and provides additional space for gathering or relaxing. Upstairs, you'll find five generous bedrooms across the second and third floors, along with two full bathrooms - perfect for families or hosting guests. Notable updates include new windows, garage doors, a high-efficiency gas furnace and water heater (2013), and central air conditioning for year-round comfort. Ideally located just minutes from Fairfield town center, train station, top-rated schools, and shopping, this home truly has it all -- Vintage character, thoughtful upgrades, and a prime location

$820,000 - Fairfield, CT

1090 Oldfield Road Fairfield, CT - Privately listed home - Contingent Welcome to this charming home located in Fairfield, CT. This residence offers a spacious and inviting layout, featuring multiple bedrooms and bathrooms for convenience, located in the heart of the sought-after beach area, walking distance to everything - town, beach, train, shopping, restaurants and parks kitchen is equipped with modern appliances and ample cabinetry, appropriate for culinary enthusiasts. The property includes a well-maintained yard, providing outdoor space for relaxation and recreation. NOTE: It has 1152 Sq ft of living area above ground and 540 Sq ft of finished lower level for Rec/Playroom, Gym. Hardwood floors throughout. Roof, Hot water tank, furnace and HVAC have been replaced, Home is NOT in flood zone, NO flood insurance required. Tesla Charger /Generator Hookup added. Furnished home - move-in ready.

$799,900 - Fairfield, CT

112 Sunset Avenue Fairfield, CT - Welcome to this expansive 6-bedroom, 3-full-bathroom split level home in the heart of Fairfield, Connecticut-one of Fairfield County's most desirable towns. This versatile residence features a dedicated in-law suite with a private bedroom, full bathroom, and potential for a kitchen conversion, ideal for extended family, guests, or a home office. The living room boasts a cozy fireplace, perfect for cooler seasons. Enjoy outdoor relaxation or entertainment on the deck overlooking a fenced-in yard. Recent updates include new carpets, freshly painted white walls, white cabinets, new stainless steel appliances, and stunning quartz countertops. A spacious basement offers additional space for storage or customization. A total of 2585 square feet of liveable space! Located in a community known for its charming New England character, excellent schools, and coastal lifestyle, you'll have access to numerous parks, playgrounds, and beautiful sandy beaches along the Long Island Sound. Experience the ultimate convenience of living within walking distance from the train station, Fairfield University, shopping, dining, parks and major highways, making commuting and everyday errands a breeze. Schedule your private tour today!

$779,999 - Fairfield, CT

74 Sterling Street Fairfield, CT - Experience refined living in this stunning 3-bedroom, 2.5-bath half duplex, thoughtfully designed with unparalleled craftsmanship and high-end finishes. This home boasts 9-foot ceilings, spacious living areas, and elegant touches throughout. With an open floor plan, the first floor features a beautiful kitchen complete with gleaming quartz countertops, a large center island, premium cabinetry, and top-tier appliances. The kitchen seamlessly flows into the dining room with sliders that lead to the outdoor patio and level backyard - perfect for gatherings and relaxation. The family room, complete with a cozy gas fireplace, creates a welcoming space. A half bath and a mudroom with custom built-ins add convenience and style to daily living. Upstairs, the primary suite offers a luxurious retreat with a giant walk-in closet and a spa-like bathroom featuring a double vanity, a beautifully tiled shower, and a relaxing soaking tub. Two additional generously sized bedrooms provide ample closet space and share a full hall bath. A second-floor laundry room adds practicality for everyday living. The home has foam insulation throughout to create a consistently comfortable environment while reducing energy consumption and costs and features a spacious basement with 8'5" ceilings offering endless possibilities for future expansion. With easy access to major commuter routes, beaches, and shopping, this home is a perfect blend of style, comfort, and convenience!

$779,999 - Fairfield, CT

Fairfield, Connecticut listings for sale

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