99 Hickok Road is a beautifully updated and meticulously maintained Dutch Colonial set on stunning landscaped property with exceptional privacy and outdoor living. Thoughtfully improved over the years, the home blends timeless elegance with modern comfort and functionality. Designed for both everyday living and entertaining, the home features gracious formal and informal spaces, a paneled first-floor office, updated kitchen with premium appliances, first-floor ensuite bedroom, new HVAC, whole-house generator, and smart-home/Sonos integration. The flexible second floor includes a spacious primary suite with sitting area and walk-in closet, two bedrooms with Jack-and-Jill bath, a large bonus/media room, and an additional flexible room ideal as a second office or potential fifth bedroom. A newly added full bath and second-floor laundry enhance convenience and versatility. Outdoor spaces feature bluestone patios and walkways, Belgian block detailing, mature landscaping, irrigation, lighting, and a newly paved driveway-creating a private, resort-like setting perfect for both relaxation and entertaining. Exceptionally cared for and turnkey, this pristine home is set on one of New Canaan's picturesque tree-lined streets.
Single-familyProperty Type
1955Year Built
2.31 acresLot Size
$589Price/Sq.Ft.
2 car garageParking
Listed by Genevieve Schettino• Compass Connecticut, LLC
Listed by Amanda Davenport• Compass Connecticut, LLC
Est. $4,671 per month, based on comparable rentals
Sale and tax history for 99 Hickok Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24174429
Aug 13, 2026
Sold
$3,475,000
$589/sq ft
Jun 5, 2026
Pending
—
May 27, 2026
Listed
$2,999,999
$508/sq ft
Smart MLS #170464316
May 31, 2022
Sold
$2,645,000
$448/sq ft
Feb 10, 2022
Listed
$2,595,000
$440/sq ft
Feb 7, 2022
Coming Soon
$2,595,000
$440/sq ft
Beautifully renovated & expanded in 2005, this sun-filled 5,700+ sq/ft custom-designed home is set on 2+ acres with easy access to New Canaan's renowned town center, schools, transportation and amenities. As you approach the home, the 240 foot New England fieldstone wall takes you back to a simpler time. The stunning interior boasts exceptional bespoke craftsmanship, premium finishes and chic style throughout. There are 2 offices; a rich mahogany one on the main level and a second off the Master Suite. The sun-drenched Family Room and Living Room with fireplace share pocket doors for privacy. Perfect for entertaining family and friends is the light-filled formal Dining Room with coffered ceiling. The Chef's Kitchen is updated and spacious and includes a center island and breakfast area. Also on the main level is a Bedroom with full Bath, perfect for guests or in-laws. Upstairs the Master Suite features a sitting area, dressing room, Bath and custom balcony. There are 2 additional well-proportioned Bedrooms with hardwood floors and Jack & Jill Bath. In addition, the rear staircase leads to a spacious bonus room ideal for relaxing and unwinding and has its own separate Bath. The Lower Level features a large playroom with wall-to-wall carpeting; a separate exercise area; laundry room and plenty of storage. There is a fenced-in yard & even a custom built shed with house grade cedar siding. Incredibly well maintained, this is the New Canaan home you have been waiting for.
Smart MLS #99153556
Jan 6, 2017
Sold
$1,550,000
$263/sq ft
Dec 9, 2016
Listing Removed
—
Jul 15, 2016
Listed
$1,699,999
$288/sq ft
Decked by curb appeal and a sophisticated setting, this home was custom designed with sun filled rooms and a spacious floor plan. Many high end finishes including rich moldings, pocket doors, and hardware. There is a mahogany paneled media room and guest suite on the first floor. Second floor has three bedrooms including grand master suite, study, and oversized bonus room. Mature landscaping, a private yard with oversized terrace and patio. Sunny playroom and plenty of storage in the LL. The renovation was done by Marc Sterling and includes a generator, 440 amps, all new baths, kitchen, utilities, windows, etc... True quality and and an exceptional value!
Renovations and addition in 2005.
Smart MLS #99094392
Jun 28, 2016
Listing Removed
—
Mar 3, 2015
Listed
$1,895,000
$321/sq ft
Smart MLS #98124032
Mar 6, 2002
Listed
$839,000
$142/sq ft
Public Records
Feb 9, 1968
Sold
$46,000
$8/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$23,109 (+3.1%)
$531,230 + $688,870
$1,220,100
2022
$22,413 (+1.2%)
$531,230 + $688,870
$1,220,100
2021
$22,157
$531,230 + $688,870
$1,220,100
2020
$22,157 (−0.4%)
$531,230 + $688,870
$1,220,100
2019
$22,255 (−2.4%)
$531,230 + $688,870
$1,220,100
2018
$22,793 (+1.7%)
$562,240 + $781,690
$1,343,930
2017
$22,403 (+2.2%)
$562,240 + $781,690
$1,343,930
2016
$21,919 (+17.7%)
$562,240 + $781,690
$1,343,930
2014
$18,620
$562,240 + $635,950
$1,198,190
Public record
Beds
4
Baths
4
Stories
2
Lot width
—
Lot depth
—
Lot size
2.31 Acres
Year renovated
—
Sq. Ft.
5,252
Year built
1955
Style
Single Family Residential
County
Fairfield County
APN
2405629
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: 9
Laundry Room Info: Lower Level, Upper Level
Interior Features: Audio System, Security System
Fireplaces Total: 1
Cooling System: Central Air
Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller