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5-Bedroom Homes for Sale in Greenfield Hill

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  • /40

    $3,750,000

    • 6 Beds
    • 7.5 Baths
    • 14,110 Sq Ft

    21 Queens Grant Dr, Fairfield, CT 06824

    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

    21 Queens Grant Dr, Fairfield, CT 06824
  • /40

    $3,300,000 Open Sat 1PM - 4PM

    • 5 Beds
    • 8 Baths
    • 6,414 Sq Ft

    750 Burr St, Fairfield, CT 06824

    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

    750 Burr St, Fairfield, CT 06824
  • /40

    $3,749,000

    • 5 Beds
    • 4.5 Baths
    • 6,661 Sq Ft

    2683 Bronson Rd, Fairfield, CT 06824

    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

    2683 Bronson Rd, Fairfield, CT 06824
  • /40

    $4,900,000

    • 6 Beds
    • 12 Baths
    • 13,979 Sq Ft

    2959 Congress St, Fairfield, CT 06824

    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

    2959 Congress St, Fairfield, CT 06824
  • /40

    $1,950,000 Open Sun 1PM - 4PM

    • 5 Beds
    • 7 Baths
    • 6,127 Sq Ft

    124 Princess Pine Ln, Fairfield, CT 06824

    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

    124 Princess Pine Ln, Fairfield, CT 06824
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    $2,650,000

    • 5 Beds
    • 4.5 Baths
    • 3,703 Sq Ft

    2821 Congress St, Fairfield, CT 06824

    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

    2821 Congress St, Fairfield, CT 06824
  • /39

    $1,800,000

    • 5 Beds
    • 6 Baths
    • 5,136 Sq Ft

    101 Brambley Hedge Cir, Fairfield, CT 06824

    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

    101 Brambley Hedge Cir, Fairfield, CT 06824
  • /40

    $1,900,000

    • 6 Beds
    • 3.5 Baths
    • 4,318 Sq Ft

    312 Towne House Rd, Fairfield, CT 06824

    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

    312 Towne House Rd, Fairfield, CT 06824
  • /40

    $15,000,000

    • 7 Beds
    • 10 Baths
    • 9,129 Sq Ft

    4800 Congress St, Fairfield, CT 06824

    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

    4800 Congress St, Fairfield, CT 06824
  • /39

    $2,099,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 5 Baths
    • 6,596 Sq Ft

    92 Hornbeam Rd, Fairfield, CT 06824

    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

    92 Hornbeam Rd, Fairfield, CT 06824
  • /40

    $2,799,000

    • 5 Beds
    • 6.5 Baths
    • 7,269 Sq Ft

    342 Midlock Rd, Fairfield, CT 06824

    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

    342 Midlock Rd, Fairfield, CT 06824
  • /33

    $2,595,000

    • 7 Beds
    • 6 Baths
    • 7,843 Sq Ft

    125 Brett Ln, Fairfield, CT 06824

    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

    125 Brett Ln, Fairfield, CT 06824
  • /18

    $9,995,000 New Construction

    • 7 Beds
    • 10 Baths
    • 10,800 Sq Ft

    688 Hulls Farm Rd, Southport, CT 06890

    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

    688 Hulls Farm Rd, Southport, CT 06890

Home Trends in Greenfield Hill, CT

Housing Trends

Median Sale Price
$365,000
Median Single Family Sale Price
$348,000
Median Townhouse Sale Price
$390,000
Median 2 Bedroom Sale Price
$384,997
Median 1 Bedroom Sale Price
$242,000
Average Price Per Sq Ft
$229
Number of Homes for Sale
14
Last 12 months Home Sales
95
Months of Supply
1.80
Median List Price
$368,499
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-21%
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