Greenfield Hill Homes for Sale

Eight minutes from downtown Westport, escape to 11 Judges Hollow-a 1930's rustic hunting cabin on 1.6 private wooded acres at the end of a long secluded driveway. A one of a kind private in holding completely surrounded by the 180 acre Brett Woods Conservation Area, this rare property offers ultimate privacy with protected open space as your permanent neighbor. Judges Hollow is nestled within

Lisa Hartmann William Pitt Sotheby's Int'l

Prepare to be wowed by this extraordinary estate featuring six bedrooms and ten-and-a-half bathrooms, spanning four meticulously designed floors. Enter through a breathtaking two-story grand foyer, leading into beautifully appointed formal and informal rooms perfect for entertaining and a gourmet kitchen that any discerning chef would envy. The luxurious primary suite serves as a private retreat,

Anissa Paolillo Redfin Corporation

Modern elegance meets estate living at 88 Merry Meet Circle, set on 3+ manicured acres in Fairfield's premier gated community, The Ridge. Perfectly positioned where Fairfield meets Westport, this gracious colonial manor offers 5+ bedrooms, 6 full and 2 half baths, and 4 beautifully finished levels-just minutes from vibrant downtowns, beaches, dining, and trains. A grand two-story foyer with a

Erin Bremen melson The Agency

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

Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's

Cindy Raney Coldwell Banker Realty

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate offers a rare opportunity in one of Fairfield's most coveted locations. Set on more than two acres of beautifully landscaped grounds with distant views of Long Island Sound, the property reflects timeless elegance and a sense of place that is hard to replicate today. Across from a distinguished

Tara Hawley Coldwell Banker Realty

Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a

Adele Higgins Higgins Group Real Estate

This is the iconic property everyone is talking about! Introducing an extraordinary new custom residence set in the beloved estate area of Upper Southport near private equestrian facilities and public trails, beaches, restaurants, train, and shopping. Masterfully designed and customized to YOUR every whim with exquisite main house, separate party barn and/or guest house, pool with spa, tennis

Jaclyn Picarillo Higgins Group Bedford Square

New Construction of a farm house style colonial in the prestigious Greenfield Hill section of Fairfield. Approvals in place for this home on a designated scenic road. 193 feet of frontage plus city water available in the street. This is an excellent opportunity to customize your dream home on a beautiful, cleared and leveled Greenfield Hill lot surrounded by nature, charming New England stone

Mona Cascella William Raveis Real Estate

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 icons 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 Music,

Leslie Razook William Pitt Sotheby's Int'l