16 Raymond Street
New Canaan, Connecticut 06840
- Beds
- 4
- Baths
- 2
- SqFt
- 2,894
- Acres
- 0.20
- Year Built
- 1877
- Property Type
- 2 Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Enjoy the ease of in-town living at its finest. Ideally located just moments from restaurants, shops, library, farmer's market, movie theater, the Metro-North train and local churches. This home offers exceptional convenience with no car required. Set on a quiet cul-de-sac, the property combines peaceful surroundings with close proximity to all the amenities of town. A rare opportunity, this legal two-family residence offers outstanding flexibility, live in one unit while generating rental income from the other, or rent both units. Perfect for commuters or those seeking a weekend retreat, the home also features a sunny backyard, ideal for gardening, relaxing, or entertaining. Thoughtfully updated, the main house includes a new washer and dryer (2026), new dishwasher and hood (2025), a perimeter fence (2023), a mini-split heating and cooling system (2023), a roof installed in 2021, and a whole house water filtration system in place. The apartment has also been well maintained with a new stove (2026), new dishwasher (2025), and washer and dryer (2023). The property is serviced by public sewer and town water. Properties with this combination of location, versatility, and charm rarely come to market. Come experience all the possibilities this exceptional home has to offer.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1877
- Days on Market
- 69 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 2,894 sq ft
- Lot Size
- 0.20 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $10,838 / Annually
Market Snapshot
The New Canaan Market
Multi-Family · trailing 12 months
Active Listings
3
1 under contract
Median List Price
$1.50M
3 active listings
Median Closed Price
$1.26M
4 sales
Median Days on Market
57
3 active listings
Median $ / Sq Ft
$708
3 active listings
Sale-to-List Ratio
95.7%
4 sales
How this home compares
List Price
$1.27M
vs $1.50M median
15.0% below median
Price / Sq Ft
$441
vs $708 median
37.7% below median
Days on Market
69 days
vs 57 days median
12 days longer than median
Based on 3 active and 4 closed sales (trailing 12 mo) of multi-family in New Canaan. Source: SmartMLS · As of July 28, 2026.
Location
16 Raymond Street, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$6,501
- Property Taxes$903
- Insurance$425
- 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
- 2,894 sq ft
- Below Grade
- 958 sq ft
Schools
- Elementary
- East
- High
- New Canaan
Interior
- Heating
- Other
- Cooling
- Split System
- Laundry
- Washer/Dryer All Units
- Laundry Location
- 2nd floor and Basement
- Basement
- FullUnfinishedStorageConcrete FloorFull With Walk-Out
Exterior & Lot
- Lot Size
- 0.20 acres
- Zoning
- BRES
- Garage / Parking
- 2 garage spaces4 total parking spacesDetached GaragePavedDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Aluminum
- Color
- Beige
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Porch-EnclosedShedPorchGuttersGarden AreaPatio
- Lot Description
- On Cul-De-Sac
Listing & Financials
- Property Taxes
- $10,838 / Annually
- Days on Market
- 69
- MLS #
- 24165564
- 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 7/28/2026. 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 7/28/2026 at 6:55 AM UTC.