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$3,395,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 5,307 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago
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The best of Rowayton comes together at 60 Crooked Trail-timeless architecture, resort-style outdoor amenities, exceptional living spaces offering the ideal coastal lifestyle. Privately set on over an acre at the end of one of Rowayton's most coveted cul-de-sacs, this beautifully updated five-bedroom home offers soaring cathedral ceilings, exposed wood beams, abundant natural light, rich millwork, and a dramatic floor-to-ceiling stone fireplace. The chef's kitchen, complete with premium appliances and custom cabinetry, is designed for both everyday living and effortless entertaining. French doors open to a wraparound covered porch and spectacular outdoor living spaces featuring a sparkling gunite pool, renovated pool house, outdoor kitchen, fireplace, bocce court, outdoor shower, expansive stone terraces, and beautifully landscaped level lawns-creating a private backyard retreat that lives like a luxury resort.The first-floor primary suite is a peaceful sanctuary with cathedral ceilings, a stone fireplace, two custom walk-in closets, a dressing area, and a spa-inspired bath. Three additional bedrooms, a flexible first-floor office or guest suite, and a finished lower level with a recreation room, gym, full bath, mudroom, and abundant storage provide exceptional comfort and versatility.

Full Property Details for 60 Crooked Trail Rd

General

  • Price: $3,395,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24186673
  • Updated: 6/26/2026
  • Added to Site: 5 day(s) ago

Interior

  • Number of Rooms: 12
  • Rooms/Areas: Bonus Room, Exercise Room, Mud Room
  • Interior Features: Audio System, Auto Garage Door Opener, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Cooktop, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Cathedral Ceiling, Beams, Bedroom Suite, Fireplace, Fr, 17 x 21, Main
  • Bedroom 1: Bedroom - Book Shelves, Built-Ins, Hardwood Floor, 10 x 10, Main
  • Bedroom 2: Bedroom - Jack & Jill Bath, Hardwood Floor, 12 x 11, Upper
  • Bedroom 3: Bedroom - Jack & Jill Bath, Hardwood Floor, 12 x 13, Upper
  • Bedroom 4: Bedroom - Balcony/Deck, Full Bath, Hardwood Floor, 13 x 13, Upper

Other Rooms

  • Family Room: Family Room - Cathedral Ceiling, Beams, Fireplace, French Doors, Hardwood Floor, 21 x 23, Main
  • Kitchen: Kitchen - Built-Ins, Granite Counters, Island, Hardwood Floor, 13 x 18, Main
  • Dining Room: Dining Room - Vaulted Ceiling, Balcony/Deck, Beams, French Doors, Hardwood Floor, 14 x 26, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Built-Ins, Hardwood Floor, 15 x 22, Lower
  • Rec Room: Built-Ins, Hardwood Floor, 15 x 22, Lower
  • Laundry: Upper Level
  • Other Room 1: Other, 13 x 15, Lower

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Pool House, In Ground Pool

Exterior

  • Exterior Features: Terrace, Wrap Around Deck, Cabana, French Doors, Patio, Grill, Deck, Garden Area, Underground Sprinkler

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Rowayton
  • Driving Directions: Witch to Ledge to Crooked Trail or Highland to Crooked Trail

School Information

  • Elementary School: Rowayton
  • Intermediate School: Roton
  • High School: Brien McMahon

Community

  • Community Name: Rowayton

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: 65 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod, Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Shingle, Wood
  • Basement Desc.: Full, Storage, Fully Finished, Garage Access, Interior Access
  • Roof: Asphalt Shingle, Gable
  • Square Feet: 5,307
  • Above Ground: 3,807 Sq. Ft.
  • Below Ground: 1,500 Sq. Ft.
  • Year Built: 1950

Lot Features

  • Lot Size (Acres): 1.21
  • Zoning: A1
  • Lot Description: Fence - Wood, Fence - Partial, Fence - Stone, Treed, Borders Open Space, Professionally Landscaped

Water Features

  • Water Front Desc.: Beach Rights

Financial Considerations

  • Assessment Amount: $1,545,530
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: see inclusions and exclusions
  • Property ID: 256520

Listed by William Raveis Real Estate, The Gatt Team at William Raveis Real Estate, Missy Dye

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Listing agent

— 60 Crooked Trail Rd —

  • Missy Dye

    William Raveis Real Estate

Agent Contact: (646) 528-6005 Office Contact: (203) 854-5116

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 60 Crooked Trail Rd

School District:Norwalk School District
NameGradesDistance
Rowayton School
1 Roton Avenue, Norwalk, CT 06853
K-50.7 mi
Roton Middle School
201 Highland Avenue, Norwalk, CT 06853
6-80.2 mi
Brien Mcmahon High School
300 Highland Avenue, Norwalk, CT 06854
9-120.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 60 Crooked Trail Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/24/2026
Listed
$3,395,000
22.12%
MLS
9/16/2024
Sold
$2,780,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 60 Crooked Trail Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$34,608
2%
$1,545,530
—
2023
$34,074
10%
$1,545,530
20%
2023
$30,928
4%
$1,292,690
—
2022
$29,648
—
$1,292,690
—
2021
$29,648
3%
$1,292,690
—
2020
$28,765
4%
$1,292,690
—
2019
$27,657
24%
$1,292,690
40%
2018
$22,270
4%
$920,460
—
2017
$21,458
2%
$920,460
—
2016
$21,115
1%
$920,460
—
2015
$20,968
4%
$917,620
3%
2014
$20,069
3%
$894,940
-7%
2011
$19,407
—
$962,780
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by William Raveis Real Estate, The Gatt Team at William Raveis Real Estate, Missy Dye

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60 Crooked Trail Road, Norwalk, CT 06853 (MLS# 24186673) is a Single Family property with 5 bedrooms and 5 full bathrooms. 60 Crooked Trail Road is currently listed for $3,395,000 and was received on June 24, 2026. Want to learn more about 60 Crooked Trail Road? Do you have questions about finding other Single Family real estate for sale in Rowayton? You can browse all Rowayton real estate or contact a Coldwell Banker agent to request more information.

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