1,011

Tokeneke, CT Homes

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  • 15 Wildcat Rd, Darien, CT 06820
    15 Wildcat Rd, Darien, CT 06820
    15 Wildcat Rd, Darien, CT 06820
    /39

    $3,850,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 6,021 Sq Ft

    15 Wildcat Rd, Darien, CT 06820

    Originally the sole residence on Wildcat Road, this distinguished 1925 stone manor blends timeless architectural elegance with a commanding setting. Located within Darien's coveted Delafield Island private association, the property is approached by a sweeping circular drive and surrounded by mature landscaping offering a rare sense of privacy, grandeur, and permanence, just minutes from downtown

    Janine Tienken Houlihan Lawrence

    15 Wildcat Rd, Darien, CT 06820
  • 48 Goodwives River Rd, Darien, CT 06820
    48 Goodwives River Rd, Darien, CT 06820
    48 Goodwives River Rd, Darien, CT 06820
    /19

    $18,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,508 Sq Ft
    • House for Rent

    48 Goodwives River Rd, Darien, CT 06820

    Step into a storybook for the summer. This picture-postcard Connecticut Colonial perfectly captures the timeless elegance of classic architecture while effortlessly delivering the modern conveniences your busy lifestyle demands. It's more than a house; it's a warm, cozy, and comfortable family home where memories are waiting to be made. Inside, you'll find a beautiful blend of original character

    Shelly Tretter Lynch Compass Connecticut, LLC

    48 Goodwives River Rd, Darien, CT 06820
  • 2 Settlers Trail Unit 3, Darien, CT 06820

    $3,175,000

    Sold Jul 31, 2026

    2 Settlers Trail Unit 3, Darien, CT 06820

    • 3 Beds
    • 2.5 Baths
    • 2,069 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Above List Price
    • $1,535/SF
    • 10 Days On Market

    Current Estimated Value $2,442,331

    Last Listing Agent Kristin Nemec William Pitt Sotheby's Int'l

    2 Settlers Trail Unit 3, Darien, CT 06820
    • 86 Delafield Island Rd, Darien, CT 06820
      86 Delafield Island Rd, Darien, CT 06820
      /2

      Est $6,030,577

      Not Listed For Sale

      86 Delafield Island Rd, Darien, CT 06820

      • 4 Beds
      • 5 Baths
      • 4,562 Sq Ft
      • Built 1930
      86 Delafield Island Rd, Darien, CT 06820

  • 6 Searles Rd, Darien, CT 06820
    6 Searles Rd, Darien, CT 06820
    6 Searles Rd, Darien, CT 06820
    /40

    $4,450,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,740 Sq Ft

    6 Searles Rd, Darien, CT 06820

    Welcome to this classic Coastal Connecticut colonial, ideally situated in the coveted Tokeneke Association - offering space, comfort, and versatility for every member of the family. With 5 bedrooms - including a convenient first-floor guest suite and four bedrooms on the second level - this home is designed for gracious everyday living. The main floor features a formal living room, elegant dining

    Susan Massey Brown Harris Stevens

    6 Searles Rd, Darien, CT 06820
  • 9 Tory Hole Rd, Darien, CT 06820
    9 Tory Hole Rd, Darien, CT 06820
    9 Tory Hole Rd, Darien, CT 06820
    /34

    $20,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,553 Sq Ft
    • House for Rent

    9 Tory Hole Rd, Darien, CT 06820

    With a total renovation completed in 2024, this pristine, airy gem offers both privacy and convenience. Beautiful, professionally-landscaped grounds, including a waterfall. Two wall-mounted TVs included. The 30X13 deck with a sylvan vista features an electric retractable awning and built-in propane grill. Large carpeted walk-up attic off the front hall. Dining area chandelier negotiable. Backup

    John Tibbets CT Waterfront Properties

    9 Tory Hole Rd, Darien, CT 06820
  • 61 Raymond St, Darien, CT 06820

    $1,850,000

    Sold Aug 24, 2026

    61 Raymond St, Darien, CT 06820

    • 4 Beds
    • 3 Baths
    • 2,094 Sq Ft
    • Built 1886

    Last Sold Summary

    • 12% Above List Price
    • $883/SF
    • 40 Days On Market

    Current Estimated Value $1,698,800

    Last Listing Agent Marina Meyers BHHS Darien/New Canaan

    61 Raymond St, Darien, CT 06820
    • 14 Tory Hole Rd, Darien, CT 06820

      Est $2,367,196

      Not Listed For Sale

      14 Tory Hole Rd, Darien, CT 06820

      • 4 Beds
      • 3.5 Baths
      • 3,133 Sq Ft
      • Built 1962
      14 Tory Hole Rd, Darien, CT 06820

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Holly Hurd Houlihan Lawrence

  • 209 Long Neck Point Rd, Darien, CT 06820
    209 Long Neck Point Rd, Darien, CT 06820
    209 Long Neck Point Rd, Darien, CT 06820
    /18

    $12,995,000

    • 5 Beds
    • 7.5 Baths
    • 7,610 Sq Ft

    209 Long Neck Point Rd, Darien, CT 06820

    This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering one acre of east facing views that can be enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored

    Shelly Tretter Lynch Compass Connecticut, LLC

    209 Long Neck Point Rd, Darien, CT 06820
  • 12 Runkenhage Rd, Darien, CT 06820
    12 Runkenhage Rd, Darien, CT 06820
    12 Runkenhage Rd, Darien, CT 06820
    /37

    $25,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,414 Sq Ft
    • House for Rent

    12 Runkenhage Rd, Darien, CT 06820

    Nestled within the prestigious Tokeneke Association, this exceptional Mediterranean-inspired waterfront residence offers sweeping southern views toward Contentment Island and an unparalleled coastal lifestyle. Complete with a seasonal dock, the property is ideal for boating, paddle boarding, kayaking, and waterfront entertaining. An oversized covered breezeway welcomes you into a private rear

    Kristina Stewart William Pitt Sotheby's Int'l

    12 Runkenhage Rd, Darien, CT 06820
  • 17 Brushy Hill Rd, Darien, CT 06820

    $3,370,000

    Sold Jan 07, 2026

    17 Brushy Hill Rd, Darien, CT 06820

    • 4 Beds
    • 4.5 Baths
    • 5,051 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Above List Price
    • $667/SF
    • 51 Days On Market

    Current Estimated Value $3,600,702

    Last Listing Agent Carolyn Brook William Pitt Sotheby's Int'l

    17 Brushy Hill Rd, Darien, CT 06820
    • 21 Tokeneke Trail, Darien, CT 06820

      Est $6,903,368

      Not Listed For Sale

      21 Tokeneke Trail, Darien, CT 06820

      • 4 Beds
      • 3 Baths
      • 1,529 Sq Ft
      • Built 1963
      21 Tokeneke Trail, Darien, CT 06820

      Last Sold Summary

      • 609 Days On Market

      Last Listing Agent Douglas Milne Houlihan Lawrence

  • 16 East Trail, Darien, CT 06820
    16 East Trail, Darien, CT 06820
    16 East Trail, Darien, CT 06820
    /39

    $7,950,000

    $1M PRICE DROP
    • 9 Beds
    • 10 Baths
    • 8,188 Sq Ft

    16 East Trail, Darien, CT 06820

    Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the

    Ashley Dineen Compass Connecticut, LLC

    16 East Trail, Darien, CT 06820
  • 7 Whaling Rd, Darien, CT 06820
    7 Whaling Rd, Darien, CT 06820
    7 Whaling Rd, Darien, CT 06820
    /34

    $28,000 Per Month

    • 5 Beds
    • 6 Baths
    • 6,748 Sq Ft
    • House for Rent

    7 Whaling Rd, Darien, CT 06820

    Like a new home! This property is FULLY furnished and located in private Salem Straits Beach Association. Rebuilt by Fox Hill builders with impressive gourmet kitchen, heated pool and every imaginable amenity. Built-in Espresso maker? Yes! Move right in with gorgeous furniture throughout. Convenient flow of spaces and great views from living areas - especially main level with a walk-out to pool &

    Pam Roberts William Pitt Sotheby's Int'l

    7 Whaling Rd, Darien, CT 06820
  • 7 Raymond Heights, Darien, CT 06820

    $1,400,000

    Sold Aug 12, 2026

    7 Raymond Heights, Darien, CT 06820

    • 3 Beds
    • 2.5 Baths
    • 1,349 Sq Ft
    • Built 1936

    Last Sold Summary

    • 5% Below List Price
    • $1,038/SF
    • 47 Days On Market

    Current Estimated Value $1,457,869

    Last Listing Agent Robin Halsey Compass Connecticut, LLC

    7 Raymond Heights, Darien, CT 06820
    • 8 Runkenhage Rd, Darien, CT 06820

      Est $2,619,445

      Not Listed For Sale

      8 Runkenhage Rd, Darien, CT 06820

      • 3 Beds
      • 2 Baths
      • 2,358 Sq Ft
      • Built 1908
      8 Runkenhage Rd, Darien, CT 06820

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Robyn Kammerer CT Waterfront Properties

  • 61 Five Mile River Rd, Darien, CT 06820
    61 Five Mile River Rd, Darien, CT 06820
    61 Five Mile River Rd, Darien, CT 06820
    /38

    $4,750,000

    • 4 Beds
    • 3 Baths
    • 3,207 Sq Ft

    61 Five Mile River Rd, Darien, CT 06820

    Rare opportunity to experience waterfront living at its finest. Perfectly positioned on the picturesque Five Mile River with 240 feet of direct water frontage, this exceptional shingle-style residence offers panoramic water views, an all-tide dock, & direct access to Long Island Sound for boating, paddleboarding, kayaking, fishing, and waterfront entertaining. Designed to embrace its setting, the

    Mitch Ross William Raveis Real Estate

    61 Five Mile River Rd, Darien, CT 06820
  • 25 Tokeneke Trail, Darien, CT 06820

    $8,695,000

    Sold Nov 21, 2025

    25 Tokeneke Trail, Darien, CT 06820

    • 5 Beds
    • 8 Baths
    • 6,108 Sq Ft
    • Built 1910

    Last Sold Summary

    • $1,424/SF
    • 29 Days On Market

    Current Estimated Value $8,735,761

    Last Listing Agent Nellie Snell William Raveis Real Estate

    25 Tokeneke Trail, Darien, CT 06820
    • 1 Runkenhage Rd, Darien, CT 06820

      Not Listed For Sale

      1 Runkenhage Rd, Darien, CT 06820

      • 6 Beds
      • 8 Baths
      • 11,192 Sq Ft
      • Built 1967
      1 Runkenhage Rd, Darien, CT 06820

      Last Sold Summary

      • 135 Days On Market

      Last Listing Agent Karen Bonner Houlihan Lawrence

  • 207 Long Neck Point Rd, Darien, CT 06820
    207 Long Neck Point Rd, Darien, CT 06820
    207 Long Neck Point Rd, Darien, CT 06820
    /21

    $16,995,000

    $2M PRICE DROP
    • 5 Beds
    • 8.5 Baths
    • 8,248 Sq Ft

    207 Long Neck Point Rd, Darien, CT 06820

    This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned

    Shelly Tretter Lynch Compass Connecticut, LLC

    207 Long Neck Point Rd, Darien, CT 06820
  • 101 Long Neck Point Rd, Darien, CT 06820

    $8,775,000

    Sold Nov 12, 2025

    101 Long Neck Point Rd, Darien, CT 06820

    • 5 Beds
    • 6.5 Baths
    • 6,689 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Below List Price
    • $1,312/SF
    • 20 Days On Market

    Current Estimated Value $8,585,907

    Last Listing Agent Becky Munro Brown Harris Stevens

    101 Long Neck Point Rd, Darien, CT 06820
    • 1 Coves End Rd, Darien, CT 06820

      Est $5,728,284

      Not Listed For Sale

      1 Coves End Rd, Darien, CT 06820

      • 6 Beds
      • 6 Baths
      • 4,807 Sq Ft
      • Built 1905
      1 Coves End Rd, Darien, CT 06820

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Elizabeth Beinfield Compass Connecticut, LLC

  • 20 Locust Hill Rd, Darien, CT 06820
    20 Locust Hill Rd, Darien, CT 06820
    20 Locust Hill Rd, Darien, CT 06820
    /39

    $3,449,000

    New Construction $200K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 6,406 Sq Ft

    20 Locust Hill Rd, Darien, CT 06820

    Welcome to 20 Locust Hill Road, a stunning in-town, new construction opportunity in Darien, CT. This now completed 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,

    Robert Marchesi Compass Connecticut, LLC

    20 Locust Hill Rd, Darien, CT 06820
  • 18 Winding Ln, Darien, CT 06820

    $3,205,000

    Sold Mar 27, 2026

    18 Winding Ln, Darien, CT 06820

    • 4 Beds
    • 3.5 Baths
    • 3,972 Sq Ft
    • Built 1963

    Last Sold Summary

    • 10% Above List Price
    • $807/SF
    • 9 Days On Market

    Current Estimated Value $3,328,041

    Last Listing Agent Tami Hanford Hughes Houlihan Lawrence

    18 Winding Ln, Darien, CT 06820
    • 8 Butlers Island Rd, Darien, CT 06820
      8 Butlers Island Rd, Darien, CT 06820
      /2

      Est $7,147,287

      Not Listed For Sale

      8 Butlers Island Rd, Darien, CT 06820

      • 5 Beds
      • 6 Baths
      • 7,515 Sq Ft
      • Built 1902
      8 Butlers Island Rd, Darien, CT 06820

  • 115 Tokeneke Rd, Darien, CT 06820
    115 Tokeneke Rd, Darien, CT 06820
    115 Tokeneke Rd, Darien, CT 06820
    /28

    $1,695,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,408 Sq Ft

    115 Tokeneke Rd, Darien, CT 06820

    Tucked away at the end of a quiet cul-de-sac known as Tokeneke Ridge, this impeccably maintained 4-bedroom, 2.5-bath home offers privacy, space, and easy everyday living. The inviting floor plan features formal living and dining rooms, an eat-in kitchen, and a flexible bonus space just off the kitchen - ideal as a playroom, home office, media room, or teen hangout. The family room opens to a deck

    Genevieve Schettino Compass Connecticut, LLC

    115 Tokeneke Rd, Darien, CT 06820
  • 0 Hay Island Unit 24078034, Darien, CT 06820

    $26,500,000

    Sold Nov 14, 2025

    0 Hay Island Unit 24078034, Darien, CT 06820

    • 6 Beds
    • 7.5 Baths
    • 8,684 Sq Ft
    • Built 2010

    Last Sold Summary

    • 24% Below List Price
    • $3,052/SF
    • 244 Days On Market

    Last Listing Agent Leslie McElwreath Sotheby's International Realty

    0 Hay Island Unit 24078034, Darien, CT 06820
    • 12 Butlers Island Rd, Darien, CT 06820
      12 Butlers Island Rd, Darien, CT 06820
      12 Butlers Island Rd, Darien, CT 06820
      /39

      Est $7,756,442

      Not Listed For Sale

      12 Butlers Island Rd, Darien, CT 06820

      • 7 Beds
      • 8.5 Baths
      • 8,491 Sq Ft
      • Built 1957
      12 Butlers Island Rd, Darien, CT 06820

      Last Sold Summary

      • 142 Days On Market

      Last Listing Agent Nancy R Dauk Brown Harris Stevens LLC

  • 155 Long Neck Point Rd, Darien, CT 06820
    155 Long Neck Point Rd, Darien, CT 06820
    155 Long Neck Point Rd, Darien, CT 06820
    /40

    $16,495,000

    • 10 Beds
    • 12 Baths
    • 11,944 Sq Ft

    155 Long Neck Point Rd, Darien, CT 06820

    Set on 2.93 private acres along coveted Long Neck Point, this extraordinary waterfront Colonial offers a rare combination of sweeping water views, privacy, and direct access to the water. Spanning more than 10,000 square feet, the residence is designed to embrace its spectacular setting, with expansive living spaces and breathtaking vistas from nearly every room. The eight-bedroom main residence

    Janine Tienken Houlihan Lawrence

    155 Long Neck Point Rd, Darien, CT 06820
  • 64 5 Mile River Rd, Darien, CT 06820

    $3,560,250

    Sold Jul 01, 2026

    64 5 Mile River Rd, Darien, CT 06820

    • 4 Beds
    • 3 Baths
    • 2,502 Sq Ft
    • Built 1810

    Last Sold Summary

    • 1% Below List Price
    • $1,423/SF
    • 26 Days On Market

    Current Estimated Value $3,514,682

    Last Listing Agent Ingrid Hess Compass Connecticut, LLC

    64 5 Mile River Rd, Darien, CT 06820
    • 3 Edgehill Dr, Darien, CT 06820

      Est $4,808,539

      Not Listed For Sale

      3 Edgehill Dr, Darien, CT 06820

      • 5 Beds
      • 4.5 Baths
      • 3,919 Sq Ft
      • Built 1921
      3 Edgehill Dr, Darien, CT 06820

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Ashley Dineen Compass Connecticut, LLC

  • 17 Contentment Island Rd, Darien, CT 06820

    $9,420,000

    Sold Mar 30, 2026

    17 Contentment Island Rd, Darien, CT 06820

    • 6 Beds
    • 4.5 Baths
    • 7,174 Sq Ft
    • Built 1909

    Last Sold Summary

    • 14% Below List Price
    • $1,313/SF
    • 149 Days On Market

    Current Estimated Value $8,363,445

    Last Listing Agent Douglas Milne Houlihan Lawrence

    17 Contentment Island Rd, Darien, CT 06820
    • 40 Old Farm Rd, Darien, CT 06820

      Est $7,072,326

      Not Listed For Sale

      40 Old Farm Rd, Darien, CT 06820

      • 5 Beds
      • 8 Baths
      • 6,474 Sq Ft
      • Built 2007
      40 Old Farm Rd, Darien, CT 06820

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Pam Pokorny Compass Connecticut, LLC

  • 15 Queens Ln, Darien, CT 06820

    $3,450,000

    Sold Jul 15, 2026

    15 Queens Ln, Darien, CT 06820

    • 5 Beds
    • 4.5 Baths
    • 3,512 Sq Ft
    • Built 1966

    Last Sold Summary

    • 21% Above List Price
    • $982/SF
    • 8 Days On Market

    Current Estimated Value $3,174,532

    Last Listing Agent Carolyn Brook William Pitt Sotheby's Int'l

    15 Queens Ln, Darien, CT 06820
    • 13 Searles Rd, Darien, CT 06820
      13 Searles Rd, Darien, CT 06820
      /2

      Est $4,963,979

      Not Listed For Sale

      13 Searles Rd, Darien, CT 06820

      • 5 Beds
      • 6 Baths
      • 4,890 Sq Ft
      • Built 1935
      13 Searles Rd, Darien, CT 06820

  • 13 Edgehill Dr, Darien, CT 06820

    $5,500,000

    Sold Aug 27, 2026

    13 Edgehill Dr, Darien, CT 06820

    • 5 Beds
    • 5 Baths
    • 3,240 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $1,698/SF
    • 106 Days On Market

    Current Estimated Value $5,667,239

    Last Listing Agent Stacy Book William Raveis Real Estate

    13 Edgehill Dr, Darien, CT 06820
    • 25 5 Mile River Rd, Darien, CT 06820

      Est $3,839,493

      Not Listed For Sale

      25 5 Mile River Rd, Darien, CT 06820

      • 4 Beds
      • 3.5 Baths
      • 3,674 Sq Ft
      • Built 1973
      25 5 Mile River Rd, Darien, CT 06820

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Cristina Veeder Compass Connecticut, LLC

  • 44 Andrews Dr, Darien, CT 06820

    $4,350,000

    Sold May 04, 2026

    44 Andrews Dr, Darien, CT 06820

    • 5 Beds
    • 6 Baths
    • 6,517 Sq Ft
    • Built 2005

    Last Sold Summary

    • 4% Above List Price
    • $667/SF
    • 10 Days On Market

    Current Estimated Value $4,346,382

    Last Listing Agent Serena Richards Brown Harris Stevens

    44 Andrews Dr, Darien, CT 06820
    • 14 Driftway Ln, Darien, CT 06820

      Est $3,276,346

      Not Listed For Sale

      14 Driftway Ln, Darien, CT 06820

      • 4 Beds
      • 3 Baths
      • 2,860 Sq Ft
      • Built 1953
      14 Driftway Ln, Darien, CT 06820

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Deirdre McGovern Compass Connecticut, LLC

  • 46 Sunswyck Rd, Darien, CT 06820

    $2,875,000

    Sold Oct 07, 2025

    46 Sunswyck Rd, Darien, CT 06820

    • 5 Beds
    • 4.5 Baths
    • 3,400 Sq Ft
    • Built 1936

    Last Sold Summary

    • 7% Above List Price
    • $846/SF
    • 11 Days On Market

    Current Estimated Value $2,981,446

    Last Listing Agent Nellie Snell William Raveis Real Estate

    46 Sunswyck Rd, Darien, CT 06820

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