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34 Bayberry Road

New Canaan, Connecticut 06840

ACTIVE$4,295,000
Beds
5
Baths
5 | 1
SqFt
7,222
Acres
2.00
Year Built
1955
Matt Caiola

Matt Caiola

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Pool3-Car Garage4 Fireplaces

About This Home

This elegant New Canaan home is distinguished by its timeless Federal-inspired architecture and gracious symmetry. The five bedroom five and a half bath residence was thoughtfully redesigned and expanded in 2007 to the highest standard. Set on two beautifully landscaped and very private acres in one of New Canaan's most coveted cul-de-sac settings, this light-filled residence offers over 7,200 square feet of refined living space that effortlessly balances elegance with warmth. The home features a generous first-floor primary suite with luxurious marble bath and walk-in closets, an inviting library with fireplace, and private office also with fireplace. A spectacular kitchen with upscale appliances and marble countertops opens to a family room which flows seamlessly for both intimate living and entertaining on a grand scale. A rear staircase opens to a spacious second floor recreation room, three oversized bedroom suites, and a cozy sitting area. Outside, a heated pool, flagstone terraces, sweeping lawns, and mature gardens create a private outdoor sanctuary worthy of the home itself. Perfectly positioned just moments from the beloved Irwin Park, commuter train, charming New Canaan village, the GreenLink Nature Trail, and highly acclaimed New Canaan public schools and library. This is a rare opportunity to own a truly special property where classic New England beauty, exceptional craftsmanship, and unparalleled location converge.

Key Facts

City/Town
New Canaan
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1955
Days on Market
42 days
Beds
5
Baths
5 full · 1 half
Living Area
7,222 sq ft
Lot Size
2.00 acres
Garage / Parking
3 garage
Property Taxes
$39,740 / 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

$4.29M

vs $3.02M median

42.0% above median

Price / Sq Ft

$595

vs $658 median

9.6% below median

Days on Market

42 days

vs 41 days median

In line with 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

34 Bayberry Road, New Canaan, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$26,643

per month

  • Principal & Interest$21,899
  • Property Taxes$3,312
  • Insurance$1,432
  • 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
7,222 sq ft

Schools

Elementary
West
High
New Canaan

Interior

Heating
Hot AirZoned
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
4
Laundry
Upper Level
Laundry Location
Separate laundry room on second floor
Appliances
Gas CooktopConvection OvenMicrowaveRange HoodSubzeroDishwasherWasherDryerWine Chiller
Basement
Crawl SpacePartialUnfinishedStorageHatchway AccessInterior AccessConcrete Floor
Interior Features
Audio SystemAuto Garage Door OpenerCable - AvailableSecurity System
Additional Rooms
FoyerLaundry RoomMud RoomSitting Room

Exterior & Lot

Lot Size
2.00 acres
Zoning
2
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
No
Pool
HeatedIn Ground Pool
Construction
ClapboardWood
Color
white
Roof
Asphalt Shingle
Foundation
Block
Exterior Features
GrillTerraceGarden AreaLighting
Lot Description
Level LotOn Cul-De-SacProfessionally LandscapedOpen Lot

Listing & Financials

Property Taxes
$39,740 / Annually
Days on Market
42
MLS #
24183490
MLS Status
Active

Similar Properties

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

Listed By

Marsha Charles

(203) 904-4663

Coldwell Banker Realty

(203) 966-3737

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 12:25 PM UTC.