16 Raymond Street, New Canaan, Connecticut 06840

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.

Flood risk: check the FEMA flood map for this address.

Taxes

Interior

Building & Exterior

Lot & Land

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $1,500,000, ranging $1,110,000 to $1,550,000.

Within a 15-minute walk, sold in the last year
• 55 New Norwalk Road5 bd · 4 ba · 1,900 sq ft · 0.5 mi away
  $1,110,000$584/sq ft2026-08-31
Within about a mile and a half, sold in the last 2 years
• 40 East Maple Street3 bd · 3 ba · 2,084 sq ft · 0.1 mi away
  $1,530,000$734/sq ft2025-05-29
• 19 Richmond Hill Road2 bd · 2 ba · 1,531 sq ft · 0.4 mi away
  $1,550,000$1,012/sq ft2024-11-06
• 16 Old Stamford Road8 bd · 4 ba · 2,304 sq ft · 0.7 mi away
  $1,500,000$651/sq ft2025-04-22
• 22 Old Stamford Road4 bd · 4 ba · 2,352 sq ft · 0.8 mi away
  $1,500,000$637/sq ft2025-04-22

Public record

From the New Canaan assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

Recorded sales

Deed transfers on file with the New Canaan land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

• 2022-10-13$975,000Two Family

More homes in New Canaan

Closest in price to this one.

• 61 Smith Ridge Road4 bed · 4 bath · 1,379 sq ft$1,300,000
• 63 Oak Street5 bed · 4 bath · 2,352 sq ft$1,500,000
• 19 Urban Street5 bed · 3 bath · 2,534 sq ft$1,795,000

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