Connecticut
New Canaan
469 Brookside Road

$3,800,000

469 Brookside Road, New Canaan, CT 06840

6 beds |
5 baths |
5,275 sqft

Single-Family Home
Built in 1820
3.43acre lot
2 car garage
$720/sqft
Listed 5 hours ago

Property Description

Dating back to the 1820's, "Shadowlyn" epitomizes the classic country compound combining beautiful vintage details with stylish, modern amenities. The bright and sunny main residence features six bedrooms, four full baths, four fireplaces and loads of comfortable living space accommodating a relaxing and easy lifestyle on over three acres with pool, charming pool house, garage/barn with apartment above and tennis court. The expansive kitchen has been thoughtfully reimagined and features a large island, extensive storage, vintage wet bar, expansive breakfast area adjacent to a cozy family room and oversized mudroom. The formal living and dining spaces boast high ceilings, tons of windows and intimate conversation alcoves, perfect for entertaining. The step down library is stunning and dramatic; wrapped in color, featuring French doors out to the terrace and private spa. The primary bedroom suite is well appointed with a walk in closet and a large, updated bath. All of these lovely spaces have direct access to sweeping vistas of this bucolic estate featuring a beautifully illuminated landscape in the evenings. Convenient to downtown New Canaan, Darien and Norwalk, Shadowlyn is accessible and exceptional. Schedule your private tour today.

Listing Status:: Active
Date Added:: October 6, 2025 at 04:37PM
Listing Office:: Compass Connecticut, LLC : (203) 442-6626
Listing Agent:: Christine Saxe : (203) 273-1548
MLS ID:: 24131109

General: Auto Garage Door OpenerCable - AvailableSaunaSecurity System
Rooms: FoyerLaundry RoomMud RoomSteam/Sauna
Appliances: Gas CooktopWall OvenRefrigeratorDishwasherWasherDryer
Laundry: Upper Level
Basement: Partial
A/C: Central Air
Heating: BaseboardHot WaterZonedOil
Fireplace: Fireplaces: 4

General: TerraceBarnLightingGuest HouseHot TubShedTennis CourtFruit TreesUnderground Sprinkler
Style: Antique
Pool: GunitePool HouseIn Ground Pool

Roofing: Asphalt Shingle

County: Fairfield

Zoning: 1AC185775

Water: Private Well
Sewer: Septic

Exclusions: Flat screen TV's

This listing courtesy of Christine Saxe, Compass Connecticut, LLC

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

Ready to Start a VA Loan?

Get Started

NMLS #1907 ^†

Get Prequalified »

Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location

Schools Nearby

South School

8 Farm Rd, New Canaan, CT, 06840

Grades KG-4

1.38 miles away

Saxe Middle School

468 South Ave, New Canaan, CT, 06840

Grades 5-8

1.19 miles away

New Canaan High School

11 Farm Rd, New Canaan, CT, 06840

Grades 9-12

1.18 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.