Greenfield Hill Homes for Sale

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

Exceptional scale and timeless elegance define this impressive 5-bedroom, 6-bath residence offering over 8,200 square feet of refined living space in one of Fairfield's most desirable locations. Thoughtfully designed for both grand entertaining and comfortable everyday living, the home features expansive sun-filled rooms, high ceilings, and a seamless flow throughout the main living areas. A

Susan Gardella William Pitt Sotheby's Int'l

Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence originally designed by renowned architect Bill Blanski has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 7,500 square feet, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces,

Erin Melson The Agency

3808 Redding Road is the kind of property that feels discovered rather than found. A place where time has softened the edges, and the landscape tells its own story. Dating to 1769 and set on nearly eighteen acres of open fields and mature trees, this is one of Fairfield's earliest homes, thoughtfully rebuilt in 2008 to preserve its character with modern ease. Inside, the home unfolds with warmth

Cindy Raney Coldwell Banker Realty

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family

Tara Hawley Coldwell Banker Realty

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 engineered for the world's most discerning icons who demand seclusion with proximity to NYC. This 38.91-acre compound ,is the mid century former home of Richard Rodgers, composer of The Sound of Music. Restored and expanded to incorporate 7 bedrooms and 7

Leslie Razook William Pitt Sotheby's Int'l

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

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

A special property with pool & tennis court, on the Westport border, minutes to shops, restaurants and train. Experience refined luxury in this picturesque setting, situated back from the road down a long, lighted driveway, winding past a serene pond. Nearly 4000 sq ft with 4 bedrooms & 4.5 baths, this open floor plan home features city water, sewer, natural gas, oil heat and central A/C for

Mary Ellen Gallagher 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

This is not just a house-it's a home with soul. Lovingly cared for and impeccably maintained by the same family for nearly 30 years, this 4-bedroom, 3.5-bath Colonial unfolds in ways you don't expect, each space more surprising than the last. The kitchen is extraordinary-a centerpiece that captivates and performs. Anchored by a single-slab Carrera marble island and a premium Thermador suite, it

Colleen Gennari William Raveis Real Estate