Fairfield, CT Homes for Sale with Acreage

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

John Foran Compass Connecticut, LLC

This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century

Leslie Razook William Pitt Sotheby's Int'l

775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully

Suzy Ryan William Raveis Real Estate

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

Cindy Raney Coldwell Banker Realty

Nestled on two private acres and bordered by more than 1,700 acres of protected nature preserve, this newly constructed estate in Weston delivers an uncommon blend of privacy and craftsmanship. Five generously proportioned bedrooms, each with its own en suite bath, offer refined comfort for family and guests alike, while a three car garage with soaring ceiling height stands ready for a car lift,

Alex De Camargo eXp Realty

This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With

Lisa Hartmann William Pitt Sotheby's Int'l

As you enter 80 Governors Lane down a private driveway, discover an 8.5-acre estate blending timeless elegance with serene privacy. This circa 1933 farmhouse, designed by architect Jack Franzen and beautifully restored, features wide plank black walnut floors, exposed beams, and a bread oven fireplace. Six spacious bedrooms include a luxurious Primary Suite with vaulted ceilings, carved mantle

Lis Reed Coldwell Banker Realty

MOVE IN READY. Nestled on a rare one-acre lot, this stunning home offers 4,180 sq ft of above-grade living space. Situated in the highly desirable University area of Fairfield, it features 5 beds/5.5 baths. The heart of the home is a culinary masterpiece with GE Monogram appliances, shaker style cabinets, premium quartz countertops and a large kitchen island. The kitchen opens to a sunlit

Jeff Poarch Poarch Realty

Welcome to 3080 Sturges - Fully Renovated Home set on 2.44 private acres in Fairfield's Greenfield Hill enclave on the Westport border. Offering a Westport mailing address together with Fairfield's acclaimed schools and amenities, this 7,317-square-foot modern residence blends architectural scale with contemporary comfort and luxury. A dramatic two-story foyer introduces interiors defined by

Ryan Sullivan Berkshire Hathaway NE Prop.

Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

Andrew Whiteley Brown Harris Stevens

Secluded Southport mini-estate built with character and attention to detail. Rarely do you find a home that needs nothing. Well loved and enhanced by the current owners including an upper level addition and expanded and renovated kitchen - the home and property have been improved and updated throughout their stewardship. Set on a gentle knoll at the end of a gated drive, enjoy sprawling lawns,

Patricia Prenderville Higgins Group Real Estate

Rich in character and designed for today's lifestyle, this distinctive Fairfield home is privately set on two picturesque acres, framed by classic New England stone walls, white fencing, mature trees, open lawns, a quintessential red barn, and a detached two-car garage. The setting offers exceptional privacy while beautifully balancing Fairfield's country landscape with the convenience of its

LJ Wilks William Pitt Sotheby's Int'l

Privately sited in the heart of Greenfield Hill, this updated home blends European-inspired architecture with the modern comforts today's luxury buyers value most. Rich in character, it offers soaring ceilings with exposed wood beams and skylights, wide-plank hardwood floors, custom built-ins, antique mantels, and repurposed antique doors throughout. The dramatic family room flows to a private

Andrew Whiteley Brown Harris Stevens

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

Julie Walsh Coldwell Banker Realty

Pristine Cape on a beautiful Stratfield street featuring a first-floor Primary Bedroom Suite, gleaming hardwood floors, and thoughtful touches throughout, blending charm, space and modern updates. The inviting Foyer opens to a stunning Dining Room with custom built-ins and an oversized Living Room overlooking the private park-like backyard. A spacious Family Room with built-ins and a fireplace

Mary Kate Klemish-Boehm Brown Harris Stevens

The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of

Leslie Razook William Pitt Sotheby's Int'l

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

Wendy Ryan Brown Harris Stevens

GREENFIELD HILL COLONIAL - Set in a beautiful Greenfield Hill location, this classic Colonial offers an exceptional blend of privacy, space, and convenience. Nestled on a picturesque 2.09-acre property framed by mature trees, stone walls and sweeping lawns, this 2,588-square-foot home features four bedrooms, two-and-one-half baths, and a very well designed floor plan. A welcoming foyer opens to a

Victoria Fingelly Higgins Group Real Estate

A rare Greenfield Hill find, 1074 Sturges Highway pairs the presence of a classic Colonial with a sleek, thoroughly modern point of view. Thoughtfully reimagined, the home retains its original craftsmanship while introducing clean-lined updates and a minimalist sensibility that feels chic, current and effortless. Inside, the balance between old and new is masterfully struck. Original millwork and

Amy Desel Compass Connecticut, LLC

*OFFERS DUE 5PM 9/21* Welcome to this quintessential New England colonial, lovingly cherished by the same owner for over 4 decades. On 2 flat, picturesque acres, this timeless home offers serene, private living while remaining centrally located. A sweeping circular driveway creates a warm arrival, while the sprawling, level backyard provides an ideal setting for outdoor entertaining, with room

Lindsey Rosen William Pitt Sotheby's Int'l

Come see this well-maintained 4-bedroom, 2.5-bath ranch set on over 2 acres in Fairfield's Greenfield Hill neighborhood. The spacious corner lot offers a private fenced-in yard along with a meticulously maintained barn. Inside, the home features central air, natural gas heat, a new deck, and multiple fireplaces. The finished lower level adds plenty of additional living space with a second

Louis Gannon William Raveis Real Estate

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

Robert Marchesi Compass Connecticut, LLC

Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury

Jaclyn Picarillo Higgins Group Bedford Square

Just a few blocks from the Greenfield Hill Green, an extraordinary opportunity awaits: a beloved estate, held by the same owners for more than 20 years, now reimagined for its next chapter. Taken virtually to the studs and thoughtfully rebuilt, much of the transformative work has already been done - creating the rare opportunity to step in at an exciting moment and complete a nearly

Daniel McCamblau Brown Harris Stevens

Nestled at the end of a cul-de-sac in the beautiful Greenfield Hill neighborhood, this fully updated and 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

Danielle Baleeiro Realty ONE Group Connect

2177 Cross Hwy welcomes you home. This extensively renovated iconic contemporary awaits your personal touches. The blending of dramatic architecture with everyday comfort, offering nearly 4,000 sq ft of functional living space designed for gathering, relaxing and entertaining. Soaring 22' ceilings, oversized windows and park-like views fill the main living area with light, while a striking

JaKeith Action Jackson ASJ Realty Partners

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

Kate Cacciatore William Raveis Real Estate

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

Gabrielle DiBianco Higgins Group Bedford Square

Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views from your bedroom? The sounds of a waterfall next door lulling you to sleep? Having sunnies tickle your toes in the summertime? Maybe a bit of fly fishing for trout? Or perhaps some paddleboarding? Yes, of course, there's a 20x40

Maryann Levanti Higgins Group Bedford Square