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23 Jonathan Road

New Canaan, Connecticut 06840

COMING SOON - NEW$2,300,000
Beds
5
Baths
3 | 1
SqFt
3,274
Acres
2.04
Year Built
1962
Matt Caiola

Matt Caiola

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Pool2-Car Garage2 Fireplaces

About This Home

INTERIOR PHOTOS ON THURSDAY. Classic Connecticut! Welcome to this spacious 5 bedroom Connecticut home in New Canaan. Stunning pastoral and romantic scenery, stone walls, and stunning heritage trees throughout your private 2 acre property on Cul-de-sac Street. The beautiful and historic Selleck's Chapel is right around the corner. Enjoy your very own post-and-beam detached barn which offers a two-car garage additional flex space, and a loft inside. Inground pool with cabana and patio receive direct sunlight, allowing for fantastic entertaining flow. It's a 7 minute picturesque drive to town on Oenoke Ridge. Brought up to today's standards with new solar panels paid in full, EV charger and a house generator. Guests approach through a circular driveway, with an additional driveway leading to the gorgeous barn for everyday living and mudroom access. This center hall colonial features a gourmet kitchen adjacent to a family room with a fireplace, vaulted ceilings and natural light. Large dining room and living room with wood burning fireplace, lead into an office or bonus room featuring exquisite antique barn floors and vaulted ceilings. Lower level has private guest suite with full bath, large laundry room, and playroom or gym. Primary bedroom with ensuite bath on the second floor has balcony overlooking the property grounds perfect for sunsets or morning coffee. 3 additional bedrooms round out the second floor with a shared, renovated bath. Enjoy the town of New Canaan!

Key Facts

City/Town
New Canaan
Neighborhood
Oenoke Ridge
Property / Style
Single Family · Colonial
Year Built
1962
Days on Market
0 days
Beds
5
Baths
3 full · 1 half
Living Area
3,274 sq ft
Lot Size
2.04 acres
Garage / Parking
2 garage
Property Taxes
$16,503 / Annually

Market Snapshot

The New Canaan Market

Single Family · trailing 12 months

View area

Median Days on Market

53

39 active listings

Median $ / Sq Ft

$681

39 active listings

Sale-to-List Ratio

102.0%

220 sales

How this home compares

List Price

$2.30M

vs $3.00M median

23.3% below median

Price / Sq Ft

$703

vs $681 median

In line with median

Days on Market

0 days

vs 53 days median

53 days fresher than median

Based on 39 active and 220 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of September 14, 2026.

Location

23 Jonathan Road, New Canaan, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$14,088

per month

  • Principal & Interest$11,946
  • Property Taxes$1,375
  • Insurance$767
  • HOA$0

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

Location

City/Town
New Canaan
Neighborhood
Oenoke Ridge
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1962
New Construction
No/Resale
Living Area
3,274 sq ft
Below Grade
552 sq ft

Schools

Elementary
West
High
New Canaan

Interior

Heating
Heat PumpHot Air
Heat Fuel
Oil
Cooling
Central AirWindow Unit
Fireplaces
2
Laundry
Lower Level
Laundry Location
Lower Level separate Laundry room.
Appliances
Gas RangeWall OvenMicrowaveRefrigeratorFreezerDishwasherWasherDryer
Basement
FullHeatedStoragePartially FinishedLiveable SpaceFull With Walk-Out
In-Law Apartment
PossibleLower Level

Exterior & Lot

Lot Size
2.04 acres
Zoning
4AC
Garage / Parking
2 garage spacesBarnDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Pool
In Ground Pool
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Level LotProfessionally Landscaped

Listing & Financials

Property Taxes
$16,503 / Annually
Days on Market
0
MLS #
24204185
MLS Status
Coming Soon

Similar Properties

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

Listed By

Holly Giordano

(917) 450-0623

William Pitt Sotheby's Int'l

(203) 655-8234

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/14/2026. 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 9/14/2026 at 3:20 PM UTC.