34 Bayberry Road
New Canaan, Connecticut 06840
- Beds
- 5
- Baths
- 5 | 1
- SqFt
- 7,222
- Acres
- 2.00
- Year Built
- 1955
- Property Type
- Single Family

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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
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
$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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 7/27/2026. 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.