Greenfield Hill Homes for Sale

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

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

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

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

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

New Construction of a shingle 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 walls

Mona Cascella William Raveis Real Estate

Welcome to Blue Bell Lane! This gracious 4-bedroom Colonial, nestled in a picturesque neighborhood offers a perfect blend of classic architecture and resort-style amenities. The outdoor paradise includes a gorgeous heated gunite pool with spa and waterfall feature surrounded by a spacious patio for relaxing, dining, and entertaining. The full-size Har Tru tennis court is every tennis lovers

Gezime Ajro Higgins Group Real Estate

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

Greenfield Hill Colonial Home on 2-Acre Lot - Great Potential This sweet colonial home has wonderful curb appeal. Situated on a spacious 2-acre lot and just waiting for the perfect buyer to polish this pearl. With a classic floor plan and options for expansion. The first floor includes a living room, dining room, den/office, and a kitchen, along with a full bath. Upstairs, there are four bedrooms

Karen Waldvogel William Raveis Real Estate

Sprawling ten room ranch style residence offering three acres on a prime estate street in Greenfield Hill. This stately home is discreetly positioned behind a brick wall and approached by a sweeping circular drive creating a grand sense of arrival. Inside this impressive home discover a striking Indoor Pool housed in its own sun lit pavilion. This dramatic recreation space adjoins the Kitchen and

Paul Triantafel William Pitt Sotheby's Int'l

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

Nestled in the heart of Greenfield Hill, this beautifully updated residence offers the perfect balance of classic New England charm and modern luxury. Set on two private, professionally landscaped acres with great curb appeal, the 4-bedroom, 4.5 bathroom home boasts spacious interiors, high-end finishes and an effortless indoor-outdoor lifestyle all with one-level living. The gracious living room

Kathy FitzSimons William Pitt Sotheby's Int'l

Welcome to your prestigious estate in Fairfield's coveted Greenfield Hill. Set back from the road, with fresh paint and new roof, this meticulously maintained elegant residence merges timeless design with modern luxury across 4,606SF of refined living space on a sprawling 2.1AC. Professional gardens and lawns provide privacy. Enjoy music from the sound system as you find hardwood floors sweeping

James Barone Compass Connecticut, LLC

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

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

This charming property located on a cul de sac in desired Greenfield Hills offers a fantastic opportunity for its new owner to personalize and enhance. This property boasts 4 bedrooms, 2 and a half baths with abundant natural light filling the home. The backyard is manageable, quiet, and private. Enjoy observing various birds and wildlife while having coffee or refreshments at your leisure.

Herman Huang Keller Williams Prestige Prop.