15

5-Bedroom Homes for Sale in Darien, CT

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  • /40

    $1,750,000 Open Sun 1PM - 3PM

    • 6 Beds
    • 5 Baths
    • 3,461 Sq Ft

    47 Hollow Tree Ridge Rd, Darien, CT 06820

    PRICE ADJUSTMENT. A Rare Darien Gem and opportunity to own this historic Federal Colonial 2-family home, one of Darien's few multi-family properties. Spanning over 3,460 SF on .47 acres, this turn-key furnished residence blends timeless elegance with modern versatility, ideal for investors, families, multi-generational households, or those seeking rental income. Historic Charm, Modern Comfort: *

    Agent Photo

    Karen Finn

    Gatehouse Realty Inc

    (475) 325-5924

    47 Hollow Tree Ridge Rd, Darien, CT 06820
  • /12

    $3,499,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 6,444 Sq Ft

    20 Locust Hill Rd, Darien, CT 06820

    Welcome to 20 Locust Hill Road, a stunning new construction opportunity in the heart of Darien, CT. This modern colonial/farmhouse-style home, constructed by an experienced builder renowned for high-end residential properties throughout Fairfield County, offers 5 bedrooms, 4.5 bathrooms, and an expansive 4,897 square feet of living space. Situated on a generous .50 acre in-town lot, this home

    Agent Photo

    Robert Marchesi

    Compass Connecticut, LLC

    (475) 253-5609

    20 Locust Hill Rd, Darien, CT 06820
  • /34

    $3,450,000

    • 5 Beds
    • 4.5 Baths
    • 3,581 Sq Ft

    98 Rowayton Ave, Norwalk, CT 06853

    Welcome to 98 Rowayton Ave, in the heart of Rowayton where you can walk to it all! This historic home has been thoughtfully renovated, combining luxury with advanced technology for modern living. The first floor boasts new hardwood floors, a first floor en suite bedroom with radiant heat marble bathroom floors. The gourmet kitchen features Wolf and Sub Zero appliances, heated quartzite

    Elizabeth Beinfield Compass Connecticut, LLC

    98 Rowayton Ave, Norwalk, CT 06853
  • /40

    $6,795,000

    • 5 Beds
    • 8 Baths
    • 6,959 Sq Ft

    10 Cross Rd, Darien, CT 06820

    If prime location and exceptional craftsmanship are what you've been looking for, look no further than 10 Cross Road. Designed and built in 2006 by Louise Brooks & Artisan Builders, this exquisite custom built home is situated on an artistically landscaped knoll in the private Tokeneke Association. Extensive woodwork & moldings, 10 foot & cathedral ceilings, and recent exterior improvements,

    Kathryn DeSalvo Compass Connecticut, LLC

    10 Cross Rd, Darien, CT 06820
  • /39

    $10,895,000

    • 6 Beds
    • 4.5 Baths
    • 7,174 Sq Ft

    17 Contentment Island Rd, Darien, CT 06820

    Introducing one of Tokeneke's most iconic waterfront estates-available for the first time in 50 years. This rare and storied compound is set on 2.4 acres of exquisitely landscaped grounds with 180 feet of private shoreline along Long Island Sound. It offers an unrivaled blend of historic charm, timeless elegance, and breathtaking coastal beauty. A sweeping two-story paneled foyer leads to a

    Douglas Milne Houlihan Lawrence

    17 Contentment Island Rd, Darien, CT 06820
  • /21

    $6,600,077

    • 6 Beds
    • 7.5 Baths
    • 7,580 Sq Ft

    14 5 Mile River Rd, Darien, CT 06820

    World class one of a kind newly constructed modern masterpiece designed by award winning architect Vita Design with stunning unobstructed water views from every room in the house. This custom coastal build sets luxury to the highest level. The home features tall ceilings with an abundance of open space filled with natural light coming in through the floor to ceiling oversized European style

    Jennifer DaSilva Mixer William Raveis Real Estate

    14 5 Mile River Rd, Darien, CT 06820
  • /37

    $8,795,000

    • 5 Beds
    • 7 Baths
    • 6,108 Sq Ft

    25 Tokeneke Trail, Darien, CT 06820

    Welcome to 25 Tokeneke Trail, an exceptional waterfront residence in the private Tokeneke Association. Perfectly positioned to capture panoramic water views from nearly every room and not in a flood zone, this home blends coastal charm with the finest in modern living. The property offers direct water access via a dock. Mooring available with approved Town application, and permitting for a deeper

    Breda Casey Brown Harris Stevens

    25 Tokeneke Trail, Darien, CT 06820
  • /38

    $17,000,000

    • 6 Beds
    • 9 Baths
    • 10,197 Sq Ft

    865 Hollow Tree Ridge Rd, Darien, CT 06820

    Blending refined elegance with complete privacy, this 9.5-acre estate is a true sanctuary for those seeking a sophisticated lifestyle. At the end of a Bradford Pear-lined gravel drive, the compound features a 10,000 sq. ft. main house, pool and pool house, two-bedroom guest cottage, and a breathtaking field house by architect Louise Brooks. The main home marries historic charm with sleek, modern

    Ashley Dineen Compass Connecticut, LLC

    865 Hollow Tree Ridge Rd, Darien, CT 06820
  • /37

    $2,695,000

    • 5 Beds
    • 4.5 Baths
    • 3,400 Sq Ft

    46 Sunswyck Rd, Darien, CT 06820

    Nestled within the highly sought-after Delafield Island Association, 46 Sunswyck Road is a distinguished brick estate set on 1.3 acres of impeccably landscaped grounds. Manicured lawns, a variety of plants, and mature trees create a serene, park-like setting that enhances the home's timeless architecture. This stately 5-bedroom residence blends classic elegance with modern upgrades. Inside, a

    Nellie Snell William Raveis Real Estate

    46 Sunswyck Rd, Darien, CT 06820
  • /29

    $2,350,000

    • 5 Beds
    • 4 Baths
    • 3,897 Sq Ft

    76 Deepwood Rd, Darien, CT 06820

    Set on a full acre in one of Darien's most sought-after neighborhoods, this property presents a rare and versatile opportunity for visionary buyers. Whether you choose to undertake a renovation-reviving the charm of mid-century modern design-or build a custom new construction estate from the ground up, the potential here is extraordinary. Surrounded by multi-million dollar homes, this centrally

    Carolyn Brook William Pitt Sotheby's Int'l

    76 Deepwood Rd, Darien, CT 06820
  • /38

    $29,500,000

    • 6 Beds
    • 7.5 Baths
    • 8,684 Sq Ft

    0 Hay Island Unit 24078034, Darien, CT 06820

    HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom,

    Leslie McElwreath Sotheby's International Realty

    0 Hay Island Unit 24078034, Darien, CT 06820
  • /41

    $29,500,000

    • 6 Beds
    • 7.5 Baths
    • 8,684 Sq Ft

    157 Long Neck Point Rd, Darien, CT 06820

    HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom,

    Leslie McElwreath Sotheby's International Realty

    157 Long Neck Point Rd, Darien, CT 06820
  • /2

    $4,900,000 New Construction

    • 5 Beds
    • 8 Baths
    • 6,535 Sq Ft

    20 Marianne Rd, Darien, CT 06820

    Dreaming of customizing your new home? Nestled on a private and flat 1.2 acres on a desirable Darien cul-du-sac, this modern-colonial stunner will feature a custom kitchen with breakfast room that opens to a sizable deck overlooking the private yard and flows into a huge great room with gas fireplace. An oversized living room is perfect for entertaining, while the first floor bedroom/office

    Serena Richards Brown Harris Stevens

    20 Marianne Rd, Darien, CT 06820
  • /40

    $3,275,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 4,274 Sq Ft

    259 Rowayton Ave, Norwalk, CT 06853

    Discover the allure of 259 Rowayton Avenue-a quintessential Victorian masterpiece that could soon be yours. This enchanting 5-bedroom, 3.5-bathroom home seamlessly marries the elegance of classic architecture with modern sophistication, offering 4,274 square feet of beautifully updated living space. The home's multiple living areas gracefully span three floors, providing abundant space for

    Elizabeth Beinfield Compass Connecticut, LLC

    259 Rowayton Ave, Norwalk, CT 06853
  • /24

    $1,275,000

    • 7 Beds
    • 3 Baths
    • 3,167 Sq Ft

    16 Columbus Place, Stamford, CT 06907

    Exceptional Multi-Family with Approved Plans for Additional Single-Family Home in Springdale. Unique opportunity to own an income-producing two-family property in the heart of Springdale with approved plans and permits in place to build a 2,500 sq.ft. detached single-family home. The existing structure includes two spacious units plus a detached garage: Unit 1: 3 bedrooms, 1,575 sq. ft. of

    Dominic Altamura Dominic A. Altamura

    16 Columbus Place, Stamford, CT 06907

Home Trends in Darien, CT

Housing Trends

Median Sale Price
$2,385,000
Median Single Family Sale Price
$2,440,000
Median Townhouse Sale Price
$1,975,000
Median 1 Bedroom Sale Price
$755,000
Average Price Per Sq Ft
$795
Number of Homes for Sale
27
Last 12 months Home Sales
299
Months of Supply
1.10
Median List Price
$2,200,000
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
24%
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