21 Hickory Drive
New Canaan, Connecticut 06840
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 3,112
- Acres
- 1.60
- Year Built
- 1959
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
PLEASE PRESENT HIGHEST & BEST OFFERS BY 4:00PM MONDAY JUNE 8TH. Nestled on 1.67 beautiful park-like acres in a charming neighborhood just minutes from town, this classic 5-bedroom, 3.5-bath Colonial offers timeless appeal, comfortable living spaces, and a lovely natural setting. Thoughtfully maintained throughout, the home features generously sized rooms, a gracious living room with fireplace, family room with custom built-ins, formal dining room, and inviting spaces designed for both everyday living and entertaining. The sun-filled walkout lower level provides wonderful additional living space, featuring a large recreation room/playroom with a wall of glass sliders opening directly to the patio and expansive backyard. Overlooking sweeping lawns and mature landscaping, the property provides a beautiful backdrop for outdoor enjoyment. A spacious deck and patio offer ideal settings for relaxing, dining al fresco, or gathering with family and friends, while the level yard provides endless possibilities for recreation and play. Conveniently located close to town, schools, and parks, this special property offers the perfect blend of classic charm, comfortable living, and a picturesque setting.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1959
- Days on Market
- 55 days
- Beds
- 5
- Baths
- 3 full · 1 half
- Living Area
- 3,112 sq ft
- Lot Size
- 1.60 acres
- Garage / Parking
- 2 garage · 2 total
- Property Taxes
- $14,282 / 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
$2.75M
211 sales
Median Days on Market
42
34 active listings
Median $ / Sq Ft
$636
34 active listings
Sale-to-List Ratio
100.5%
211 sales
How this home compares
List Price
$1.70M
vs $3.02M median
44.0% below median
Price / Sq Ft
$545
vs $636 median
14.3% below median
Days on Market
55 days
vs 42 days median
13 days longer than median
Based on 34 active and 211 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of July 28, 2026.
Location
21 Hickory Drive, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$8,642
- Property Taxes$1,190
- Insurance$565
- 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
- 1959
- New Construction
- No/Resale
- Living Area
- 3,112 sq ft
- Below Grade
- 600 sq ft
Schools
- Elementary
- East
- High
- New Canaan
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Gas RangeRange HoodSubzeroDishwasherWasherDryer
- Basement
- FullHeatedStorageFully FinishedWalk-out
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 1.60 acres
- Zoning
- 2AC
- Garage / Parking
- 2 garage spaces2 total parking spacesAttached GaragePavedDrivewayPrivatePavedAsphalt
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Shingle
- Roof
- Asphalt Shingle
- Foundation
- Block
- Exterior Features
- GazeboDeckGuttersStone WallPatio
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $14,282 / Annually
- Days on Market
- 55
- MLS #
- 24168485
- MLS Status
- Under Contract
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:15 AM UTC.