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99 Hickok Road

New Canaan, Connecticut 06840

PENDING$2,999,999
Beds
4
Baths
4 | 1
SqFt
5,902
Acres
2.31
Year Built
1955
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

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.

Key Facts

City/Town
New Canaan
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1955
Days on Market
59 days
Beds
4
Baths
4 full · 1 half
Living Area
5,902 sq ft
Lot Size
2.31 acres
Garage / Parking
2 garage
Property Taxes
$28,489 / Annually

Market Snapshot

The New Canaan Market

Single Family · trailing 12 months

Median Days on Market

41

34 active listings

Median $ / Sq Ft

$658

34 active listings

Sale-to-List Ratio

100.6%

212 sales

How this home compares

List Price

$3.00M

vs $3.02M median

In line with median

Price / Sq Ft

$508

vs $658 median

22.8% below median

Days on Market

59 days

vs 41 days median

18 days longer than median

Based on 34 active and 212 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of July 27, 2026.

Location

99 Hickok Road, New Canaan, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$18,670

per month

  • Principal & Interest$15,296
  • Property Taxes$2,374
  • Insurance$1,000
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
New Canaan
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1955
New Construction
No/Resale
Living Area
5,902 sq ft
Below Grade
650 sq ft

Schools

Elementary
East
High
New Canaan

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Lower LevelUpper Level
Appliances
Gas CooktopWall OvenMicrowaveRange HoodSubzeroDishwasherWasherDryerWine Chiller
Basement
FullPartially Finished
Interior Features
Audio SystemSecurity System
Additional Rooms
Laundry RoomMud RoomSitting Room

Exterior & Lot

Lot Size
2.31 acres
Zoning
2AC
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Shingle
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedPorchStone WallFrench DoorsPatio
Lot Description
Lightly WoodedLevel LotSloping LotProfessionally Landscaped

Listing & Financials

Property Taxes
$28,489 / Annually
Days on Market
59
MLS #
24174429
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Genevieve Schettino

(203) 604-5270

Compass Connecticut, LLC

(203) 423-3100

Co-Listed By

Amanda Davenport

Compass Connecticut, LLC

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/27/2026 at 8:40 PM UTC.