New Canaan, CT / 9 DAYS ON MARKET

523 Brookside RoadNew Canaan, CT 06840

Asking price$1,995,000Active

Our Take

523 Brookside Road is a 1959 Colonial on 2.59 acres, set at the end of a long private drive south of the Merritt Parkway. The five-bedroom, three-full-bath, one-half-bath home includes four bedrooms in the main house and a private suite above the garage. Interior features include a front-to-back living room with fireplace, detailed built-ins, a kitchen with a second fireplace, and a family room with seasonal views. Finished lower-level recreation space and a terrace provide additional areas for activities and outdoor dining.

Estimated buyer rebate

Buy with Cress and Save $19,950 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 40% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24201426
Bedrooms
5
BathroomsBaths
3 full / 1 half
Square feet
3,286
Year built
1959
Acres
2.59
Property taxes
$21,324

July 2026-June 2027

What stands out

  • Private drive south of the Merritt Parkway
  • Living and dining rooms with custom built-ins
  • Kitchen with a second fireplace
  • Family room with seasonal views
  • Private fifth-bedroom suite above the garage
  • Finished lower-level recreation space
  • Terrace for outdoor dining and entertaining
Read the full listing description

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.

Schools

Elementary
South
Middle
Saxe Middle
High
New Canaan

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

Open Google Maps ↗

523 Brookside Road, New Canaan, CT 06840

Price history

DateEventPrice
Originally listed$1,995,000

Intermediate price changes and previous listings may not be included.

Could this be your next home?

Let’s talk about the property—and what working with Cress could save you.

Inquire about this property →

*Estimate: $1,995,000 asking price × assumed 2.5% buyer-agent commission × 40% rebate = $19,950. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by William Pitt Sotheby's Int'l · (203) 966-2633

Lisa O'rourke

SmartMLS · Listing #24201426 · Active

Listing data checked: Sep 17, 2026, 7:06 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

For personal, noncommercial use to identify properties you may be interested in purchasing.