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.
A private, stunning retreat in the heart of Rowayton featuring gracious living spaces, spectacular outdoor amenities, and an effortless walk-to-town coastal lifestyle offered in this unique exceptional property!
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Market trends in 06853, CT
Last updated September 2026
Buyer's Market
Seller's Market
Seller's market
Sale-to-List Price
104.2%
4.1% MoM
Median sale price
$2.5M
$26K MoM
Avg. days on market
26d
11 days MoM
Recently sold homes
14
3 MoM
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Rental estimate
Est. $4,439 per month, based on comparable rentals
Sale and tax history for 60 Crooked Trail Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24186673
Oct 1, 2026
Sold
$3,460,000
$652/sq ft
Jul 17, 2026
Pending
—
Jun 24, 2026
Listed
$3,395,000
$640/sq ft
Smart MLS #24026554
Sep 16, 2024
Sold
$2,780,000
$524/sq ft
Jul 31, 2024
Pending
—
Jul 25, 2024
Contingent
—
Jul 6, 2024
Price Changed
$2,895,000
$546/sq ft
Jun 20, 2024
Listed
$2,995,000
$564/sq ft
Jun 19, 2024
Coming Soon
$2,995,000
$564/sq ft
Sitting atop 1.2 private acres just minutes from downtown Rowayton, and Rowayton station, 60 Crooked Trail is one-of-a-kind in every way. The house is discretely tucked away on a flat, high and dry lot surrounded by thoughtful landscape design which includes a gunite pool, blue stone patio, built in grilling bar, bocci court and separate pool house. Spend crisp falls days snuggled up in front of the impressive stone outdoor fireplace and make use of indoor and outdoor living in nearly every season. Inside, you'll find impressive vaulted ceilings in throughout much of the main floor, including custom-designed two story windows that highlight the impressive property. The updated kitchen boasts two dishwashers, a gas range and stunning Vermont quartzite countertops. The impressive architectural design continues into the main floor master suite with vaulted ceilings, incredible views of the back patio and pool, two walk in closets and a lovely master bathroom. There are two bedrooms on the main floor, three on the second floor (including one with an en suite bathroom, and two others with a jack and Jill bath), and a fully finished walk out lower level, with a bonus room, full bath, mudroom and large gym.
Smart MLS #170412917
Oct 7, 2021
Sold
$2,350,000
$443/sq ft
Sep 1, 2021
Listing Removed
—
Jul 13, 2021
Contingent
—
Jul 6, 2021
Listed
$2,350,000
$443/sq ft
Jul 4, 2021
Coming Soon
$2,350,000
$443/sq ft
Sitting atop 1.2 private acres just minutes from downtown Rowayton, and Rowayton station, 60 Crooked Trail is one-of-a-kind in every way. The house is discretely tucked away on a flat, high and dry lot surrounded by thoughtful landscape design which includes a gunite pool, blue stone patio, built in grilling bar, bocci court and separate pool house. Spend crisp falls days snuggled up in front of the impressive stone outdoor fireplace and make use of indoor and outdoor living in nearly every season. Inside, you’ll find impressive vaulted ceilings in throughout much of the main floor, including custom-designed two story windows that highlight the impressive property. The updated kitchen boasts two dishwashers, a gas range and stunning Vermont quartzite countertops. The impressive architectural design continues into the main floor master suite with vaulted ceilings, incredible views of the back patio and pool, two walk in closets and a lovely master bathroom. There are two bedrooms on the main floor, three on the second floor (including one with an en suite bathroom, and two others with a jack and Jill bath), and a fully finished walk out lower level, with a bonus room, full bath, mudroom and large gym.
Smart MLS #99185928
Oct 13, 2017
Sold
$1,850,000
$349/sq ft
Sep 22, 2017
Listing Removed
—
May 15, 2017
Listed
$1,950,000
$367/sq ft
Smart MLS #99175061
May 15, 2017
Listing Removed
—
Mar 3, 2017
Listed
$1,950,000
$367/sq ft
Smart MLS #99134317
Jun 24, 2016
Listing Removed
—
Feb 29, 2016
Listed
$2,095,000
$395/sq ft
Smart MLS #99010258
Jul 16, 2013
Listing Removed
—
Nov 19, 2012
Listed
$1,650,000
$311/sq ft
Smart MLS #98475107
Feb 28, 2011
Listing Removed
—
Aug 30, 2010
Listed
$1,875,000
$353/sq ft
Smart MLS #98376625
Aug 2, 2008
Listing Removed
—
Apr 30, 2008
Listed
$2,295,000
$432/sq ft
Public Records
Mar 8, 2004
Sold
$641,500
$121/sq ft
Smart MLS #98179222
Oct 22, 2003
Listed
$659,000
$124/sq ft
Public Records
Sep 2, 1998
Sold
$340,000
$64/sq ft
Smart MLS #98015339
Jun 1, 1998
Listed
$349,000
$66/sq ft
Public Records
Mar 3, 1997
Sold
$300,000
$57/sq ft
Smart MLS #96018242
May 31, 1996
Listed
$334,000
$63/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$30,928 (+4.3%)
$427,180 + $865,510
$1,292,690
2022
$29,648 (+3.5%)
$427,180 + $865,510
$1,292,690
2021
$28,651 (−0.4%)
$427,180 + $865,510
$1,292,690
2020
$28,765 (+4.0%)
$427,180 + $865,510
$1,292,690
2019
$27,657 (+24.2%)
$427,180 + $865,510
$1,292,690
2018
$22,270 (+3.8%)
$357,270 + $563,190
$920,460
2017
$21,458 (+1.6%)
$357,270 + $563,190
$920,460
2016
$21,115 (+5.2%)
$357,270 + $563,190
$920,460
2014
$20,069
$357,270 + $537,670
$894,940
Public record
Beds
5
Baths
5
Stories
2
Lot width
—
Lot depth
—
Lot size
1.21 Acres
Year renovated
—
Sq. Ft.
3,807
Year built
1950
Style
Single Family Residential
County
Fairfield County
APN
256520
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 2
Interior
Interior Information
Total Rooms: 12
Laundry Room Location: 2nd Floor
Laundry Room Info: Upper Level
Interior Features: Audio System, Auto Garage Door Opener, Security System
In-Law Apartment: No
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Gas Cooktop, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer