16 Raymond Street
New Canaan, Connecticut 06840
- Beds
- 5
- Baths
- 2
- SqFt
- 1,936
- Acres
- 0.20
- Year Built
- 1877
- Property Type
- 2 Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
3
1 under contract
Median List Price
$1.30M
3 active listings
Median Closed Price
$1.25M
5 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 3, 2026per 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
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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 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.