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16 Raymond Street

New Canaan, Connecticut 06840

ACTIVE - NEW$1,250,000
Beds
5
Baths
2
SqFt
1,936
Acres
0.20
Year Built
1877
Matt Caiola

Matt Caiola

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2-Car Garage

About This Home

An incredible opportunity to own a beautifully updated two-family home in the heart of New Canaan-perfect for those looking to enjoy the New Canaan lifestyle while benefiting from valuable rental income. The spacious first-floor residence offers three bedrooms and has been thoughtfully updated for modern living, highlighted by a stunning, high-end renovated kitchen designed to be as beautiful as it is functional. Fresh, sophisticated finishes create a move-in-ready home with the space and comfort today's buyers are looking for. Upstairs, the second-floor apartment has been completely renovated from top to bottom, offering a fresh, modern living environment with all-new windows, new appliances, a beautifully renovated bathroom, and its own separate washer and dryer. Stylish finishes and thoughtful updates make this an exceptionally appealing rental. Whether you choose to live in one residence and offset your monthly expenses with income from the other, accommodate extended family, or add a desirable New Canaan property to your investment portfolio, 16 Raymond Street offers flexibility, income potential, and long-term value in one of Fairfield County's most sought-after communities. A rare opportunity to combine the benefits of homeownership, rental income, and the New Canaan lifestyle-all under one roof.

Key Facts

City/Town
New Canaan
Neighborhood
N/A
Property / Style
Multi-Family · Units on different Floors
Year Built
1877
Days on Market
0 days
Beds
5
Baths
2 full
Living Area
1,936 sq ft
Lot Size
0.20 acres
Garage / Parking
2 garage
Property Taxes
$11,018 / Annually

Market Snapshot

The New Canaan Market

Multi-Family · trailing 12 months

Median Days on Market

90

3 active listings

Median $ / Sq Ft

$708

3 active listings

Sale-to-List Ratio

92.5%

5 sales

How this home compares

List Price

$1.25M

vs $1.30M median

In line with median

Price / Sq Ft

$646

vs $708 median

8.8% below median

Days on Market

0 days

vs 90 days median

90 days fresher than median

Based on 3 active and 5 closed sales (trailing 12 mo) of multi-family in New Canaan. Source: SmartMLS · As of September 6, 2026.

Location

16 Raymond Street, New Canaan, Connecticut

Property + 3 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$7,794

per month

  • Principal & Interest$6,459
  • Property Taxes$918
  • Insurance$417
  • 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
Multi-Family
Subtype
Duplex
Style
Units on different Floors
Year Built
1877
New Construction
No/Resale
Living Area
1,936 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Other
Cooling
Central Air
Laundry
Washer/Dryer All Units
Basement
FullUnfinished

Exterior & Lot

Lot Size
0.20 acres
Zoning
BRES
Garage / Parking
2 garage spacesDetached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Aluminum
Roof
Asphalt Shingle
Foundation
Stone
Lot Description
Level LotOn Cul-De-Sac

Listing & Financials

Property Taxes
$11,018 / Annually
Days on Market
0
MLS #
24204972
MLS Status
Active

Similar Properties

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

Listed By

Wende Foreman

(203) 981-4550

William Pitt Sotheby's Int'l

(203) 968-1500

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/6/2026. 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 9/6/2026 at 8:40 PM UTC.