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469 Brookside RoadNew Canaan, CT 06840

For Sale

$3,800,000

Smart Buyer Rebate $38,000

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.

Listed by Christine Saxe

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Compass Connecticut, LLC

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(203) 273-1548

Listed by Amanda Bryan

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Compass Connecticut, LLC

Last updated October 15, 2025

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Source: SmartMLS #24131109

Listing Facts

  • TypeSingle-family
  • NeighborhoodNew Canaan
  • Bedrooms6
  • Bathrooms5
  • Days on Prevu16
  • Taxes$32,766/year
  • Size5,275 sqft
  • Price per sqft$720

Location

Mortgage Calculator

Listing History

10/06/2025
Listed by Compass Connecticut, LLC
$3,800,000

Property Details for 469 Brookside Road

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1820
  • Year Built Details: Approximate
  • Architectural Style: Antique
  • Construction Materials: Frame
  • Exterior Features: Terrace, Barn, Lighting, Guest House, Hot Tub, Shed, Tennis Court, Fruit Trees, Underground Sprinkler

Features

  • Pool Features: Gunite, Pool House, In Ground Pool
  • Pool Private: Yes
  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Level Lot, Professionally Landscaped, Rolling, Open Lot
  • Lot Size Acres: 3.43

Financial

Taxes

  • Parcel Number: 185775
  • Tax Annual Amount: $32,766.00
  • Tax Year: 25

Interior

Features

  • Appliances: Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
  • Fireplaces Total: 4
  • Interior Features: DROPEN, CABLE, SAUNA, SECURESY

Rooms

  • Basement: Partial
  • Bathrooms Full: 5
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 6
  • Rooms Total: 13

Other

General

  • Exclusions: Flat screen TV's

Parking

Parking

  • Attached Garage: Barn, Detached Garage
  • Garage Spaces: 2

Schools

Elementary School

  • Elementary School: South

High School

  • High School: New Canaan

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Baseboard, Hot Water, Zoned
  • Laundry Features: Upper Level
  • Sewer: Septic
  • Water Source: Private Well

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.