523 Brookside Road, New Canaan, Connecticut 06840

About this home

Nestled at the end of a long private drive south of the Merritt Parkway, this classic Colonial offers timeless character, generous living space, and a highly convenient location. Beautifully expanded and thoughtfully updated years ago, the home showcases exceptional craftsmanship, enduring quality, and solid construction described as having "great bones." The main level is rich with architectural detail - an elegant front-to-back Living Room with fireplace and exquisite custom built-in cabinetry and the Dining Room with beautiful built-in details. At the heart of the home is an expansive Kitchen featuring high-end appliances, custom built-ins, and a second fireplace in the casual dining area-an inviting space for morning coffee, relaxed meals, or entertaining. The adjacent light-filled Family Room offers beautiful views of the changing seasons and provides a comfortable extension of the main living areas. The house includes four spacious bedrooms and 2.5 baths, while a private suite above the garage adds a fifth bedroom with full bath, offering flexibility for guests, a private office or additional living space. Finished recreational space on the lower level provides room to work, play, exercise and the generous terrace creates an inviting setting for outdoor dining and entertaining. With its distinctive architecture, thoughtful layout, and quality details, the home offers an exceptional foundation for personalization, including some cosmetic updating to the exterior.

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

Schools

Taxes

Interior

Building & Exterior

Lot & Land

Energy

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 $2,100,000, ranging $1,800,000 to $2,725,000.

Within a 15-minute walk, sold in the last year
• 463 White Oak Shade Road4 bd · 3 ba · 3,224 sq ft · 0.1 mi away
  $2,300,100$713/sq ft2026-09-01
• 788 South Avenue3 bd · 3 ba · 3,143 sq ft · 0.4 mi away
  $1,800,000$572/sq ft2026-05-21
• 34 Horton Lane4 bd · 4 ba · 3,512 sq ft · 0.4 mi away
  $2,725,000$775/sq ft2026-07-13
• 213 Marvin Ridge Road4 bd · 4 ba · 3,846 sq ft · 0.7 mi away
  $2,100,000$546/sq ft2025-11-14
• 44 Putnam Road5 bd · 4 ba · 3,724 sq ft · 0.7 mi away
  $1,817,000$487/sq ft2025-12-16

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.

More homes in New Canaan

Closest in price to this one.

• 20 Gray Squirrel Drive4 bed · 3 bath · 3,530 sq ft$1,995,000
• Gravel Island Road4 bed · 3 bath · 4,183 sq ft$1,999,000
• 327 Jelliff Mill Road5 bed · 5 bath · 3,383 sq ft$2,000,000
• 12 Norholt Drive4 bed · 3 bath · 2,802 sq ft$2,250,000
• 761 New Norwalk Road5 bed · 4 bath · 2,904 sq ft$1,699,000
• 178 Pocconock Trail5 bed · 4 bath · 4,543 sq ft$2,295,000

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