Fairfield, CT Homes for Sale with Acreage

Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

Andrew Whiteley Brown Harris Stevens

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

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.

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

108 Old Farm Road is a stunning new construction currently underway in one of Weston's most desirable settings. This five-bedroom, 5.5-bath home offers 4,568 square feet above grade plus a 1,400 square foot finished heated lower level with home theater, totaling nearly 6,000 square feet of exceptional living space. The main level features soaring two-story ceilings, a formal dining room, home

Alex De Camargo eXp Realty

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

Set on one of Fairfield's most coveted streets, this is the kind of home families spend years hoping will become available. Set on 3.35 acres on prestigious Verna Hill Road, adjacent to Fairfield Country Day School, this is the kind of property that becomes the backdrop for decades of memories. Summer afternoons by the pool and spa. Holiday dinners that bring everyone together. At the center of

Wendy Ryan Brown Harris Stevens

Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 8,000 sq ft, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces, and expansive windows that frame tranquil pond views. A

Erin Melson The Agency

CHESTNUT GROVE - Wonderful opportunity to enhance an extraordinary, sweeping 2.39 acre parcel in a beautiful and bucolic Greenfield Hill location. This expansive property nestled within a Chestnut Grove, features a stately Barn providing Garage storage suitable for farming equipment and motor vehicles, and a recently constructed second story Studio Apartment enjoying a haven of privacy and

Victoria Fingelly Higgins Group Real Estate

111 Golden Pond Lane is the rare luxury home that feels as welcoming as it is impressive. Tucked at the end of a quiet, tree-lined cul-de-sac, the home opens with an undeniable scale - soaring 19-foot ceilings, a dramatic two-story entry, sweeping staircases, and natural light that moves effortlessly throughout the day. Yet what makes the home memorable is not its grandeur alone, but the warmth

Cindy Raney Coldwell Banker Realty

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

Compelling Value in Greenfield Hill! Nestled amid mature trees and natural surroundings, this 5-bedroom, 4-bath home offers an exceptional combination of space, privacy, and functionality. The open living room and family room provide flexible living spaces with seamless access to the covered porch and expansive deck overlooking the peaceful setting and side yard. The spacious eat-in kitchen

Lori Auerbach Coldwell Banker Realty

Rare 2.25-acre riverfront opportunity on the Fairfield/Westport line. This exceptional 538-foot deep lot offers 158 feet of frontage along the Aspetuck River, creating a private, scenic setting with significant upside. A unique feature is the ability to site a new home further back from Westport Turnpike, maximizing privacy and long-term value. The existing 3-bedroom, 2-bath ranch offers

Chip Parrish Keller Williams Realty

A Connecticut Classic - this center hall Colonial is located on the most charming stretch in Greenfield Hill. Beautifully set on 2 acres, this 4 bedroom Jack Franzen designed home lives large in all aspects. Guests are welcomed into the double height foyer flanked by formal living and dining rooms. The great room spans the back of the house combining a gorgeous light, bright & well appointed

Jeannette Floto Compass Connecticut, LLC

3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original

Cindy Raney Coldwell Banker Realty

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

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

Nestled on a sprawling one-acre lot, this stunning new home offers 4180 sq ft of above-grade living space. Situated in the highly desirable University area of Fairfield, it features 5 bedrooms/5.5 bathrooms. The heart of the home is a culinary masterpiece with GE Monogram appliances, classic shaker-style cabinetry, quartz countertops and a large kitchen island. The kitchen flows into a sunlit

Jeff Poarch Poarch Realty

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

A rare WATERFRONT offering in one of Westport's most coveted enclaves. This beautifully composed estate is gracefully sited on more than two private, tree-lined acres, encompassing sweeping views of Sasco Creek, Southport Beach, and Long Island Sound while preserving an exceptional sense of seclusion. Designed to maximize its remarkable setting, the home captures water views from nearly every

Christine McKinney William Raveis Real Estate

14 Saw Mill Road offers the convenience of suburban metropolitan New York living while maintaining a quaint, calm retreat by design. You are greeted by a historic draw bridge within the private drive that leads to the professionally landscaped and beautifully cared for lot. This home sits on about 2 acres, with privacy and room to live inside and out all year round. This oversized ranch offers a

Kelsey Emmons Coldwell Banker Realty

Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is this new construction home built by CCO Habitats. Three levels of finished living space with ten foot ceilings on the first floor give an amazing sense of openness, as well as better functionality than four level homes. Think about it. Who really wants to walk up to the third floor every day? That's

Maryann Levanti Higgins Group Bedford Square