99 Hickok Road
New Canaan, Connecticut 06840
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 5,902
- Acres
- 2.31
- Year Built
- 1955
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
34
51 under contract
Median List Price
$3.02M
34 active listings
Median Closed Price
$2.74M
212 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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.
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.