5-Bedroom Homes for Sale in Greenfield Hill

Welcome to one of Greenfield Hill's most distinguished residences-an extraordinary 9,700+ sq. ft. Colonial estate nestled on 2 pristine acres in one of Fairfield's most prestigious enclaves. This 5-6 bedroom architectural masterpiece combines timeless elegance with modern luxury, offering an unparalleled lifestyle just moments from town. From first look, the home's unrivaled curb appeal

Michael Debiase Keller Williams Realty

Lions Gate: No need to move to the south of France as this extraordinary residence is right here in coveted Fairfield. Enter through grand gates into a world of privacy where character, convenience, security & serenity magically meet. Magazine-worthy grounds are the soul of the estate-lush, expansive, & exquisitely curated. With a shimmering pool, spectacular California Redwood Pool House with

Julie Vanderblue Higgins Group Real Estate

Located in the heart of Greenfield Hill at the top of Bronson Road, this iconic Connecticut estate sits on 2+ beautifully landscaped acres with distant water views of Long Island Sound. Across from a majestically developed family and horse-farm compound and outside the historic district, this home blends old-world charm with modern comforts. Originally built in 1844 and significantly expanded and

Tara Hawley Coldwell Banker Realty

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

Anissa Paolillo Redfin Corporation

Luxury Living on the Fairfield/Westport Border Set in the heart of Greenfield Hill, this exceptional 6-bedroom, 8-bath estate offers a rare combination of privacy, elegance, and resort-style amenities-just minutes from the Post Road and 50 miles from NYC. Thoughtfully positioned on the Fairfield/Westport line, the residence features expansive, sun-filled interiors ideal for everyday living and

Andrew Whiteley Brown Harris Stevens

Set on 2.98 private acres at the end of a cul-de-sac in coveted Greenfield Hill, this elegant 4627+ SF Colonial offers the perfect blend of luxury, space, and functionality. From the grand 2-story foyer to the exquisite crown moldings, every detail exudes timeless sophistication. Designed for entertaining, the home features a gracious flow with expansive living and gathering spaces, a gourmet

Elizabeth Tritschler William Raveis Real Estate

Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A

Andrew Whiteley Brown Harris Stevens

Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury

Akenmisire Musa The Agency

A gracious front porch welcomes you to this sophisticated colonial where comfort and luxury abound. The entry hall with striking floor to ceiling picture frame molding, setting the tone for the refined details found throughout the home. The family room greets you with many carefully curated features including book shelves framing the entry, coffered ceiling, gas fireplace flanked by built in

Paulette Cuozzo William Raveis Real Estate

Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the

Leslie Razook William Pitt Sotheby's Int'l

Perfectly sited on a quiet cul-de-sac in the Greenfield Hill neighborhood, this exquisite farmhouse-style home offers over 5,000 sq ft of elegant living space on a spectacular, level property. The classic character and contemporary elegance defines this home offering 5 bedrooms, 5 baths, custom millwork, refined designer details and exceptional outdoor living. Step into a gracious foyer flanked

Jennifer Lockwood Coldwell Banker Realty

Welcome to Summer Tree Gardens, an extraordinary stately home nestled on over 2 acres of meticulously maintained grounds in the prestigious Greenfield Hill neighborhood of Fairfield, CT. This expansive 7,269 sq. ft. home boasts 5 en-suite bedrooms, 8.5 baths, and an array of luxurious features that blend timeless elegance with modern updates. The home was built by builder Christer Krook. Step

Ken Osborn Higgins Group Bedford Square

Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Go into the elegant formal living and dining rooms, both warmed by inviting FPs, setting the stage for memorable moments. The custom gourmet kitchen, designed for living, opens

Linna Yuen Coldwell Banker Realty

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