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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