Home / Recently Sold / New Canaan
Closed · For Sale
$3,850,000
Asked $3,800,000 · Sold 2025-12-16

469 Brookside Road, New Canaan, Connecticut 06840

6 beds 5 baths 5,275 sq ft Single Family For Sale Built 1820

About this home

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.

Status
Closed
Type
Single Family For Sale
Price
$3,850,000
Beds
6
Baths
5
Interior
5,275 sq ft
Lot
3.43 ac
Year Built
1820
MLS #
24131109
ZIP
06840
Days on Market
25
Heat
Oil · Baseboard, Hot Water, Zoned
Cooling
Central Air
Water
Private Well
Sewer
Septic
Parking
Barn, Detached Garage (2-car)
Laundry
Upper Level — Second Floor

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

Schools

Elementary
South
High School
New Canaan

Taxes

Property tax
$32,766 (July 2025-June 2026)
Assessed value
$1,963,220

Interior

Appliances
Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
Basement
Partial
Attic
Walk-up
Fireplaces
4
Total rooms
13

Building & Exterior

Style
Antique
Roof
Asphalt Shingle
Siding
Clapboard
Exterior features
Terrace, Barn, Lighting, Guest House, Hot Tub, Shed, Tennis Court, Fruit Trees, Underground Sprinkler
Foundation
Stone
Pool
Gunite, Pool House, In Ground Pool
New construction
No/Resale

Lot & Land

Zoning
1AC
Lot
Level Lot, Professionally Landscaped, Rolling, Open Lot

What's nearby

Grocery
ShopRite1.99 mi away
Also nearby
Wegmans2.07 mi away
Pharmacy
CVS Pharmacy2.25 mi away
Train
Talmadge Hill Station1.24 mi awayMetro-North Railroad
Elementary
South
High school
New Canaan
School zone
Check the district's school finder the MLS did not name one for this address
~1.7 miShopRite — 1.99 miWegmans — 2.07 miCVS Pharmacy — 2.25 miTalmadge Hill — 1.24 mi
This homeGroceryPharmacyTrain

Real streets from OpenStreetMap; distances are straight-line from the property, not driving routes.

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Listing & sale history

Every time this exact home has come to market in the MLS data this site tracks. Where a sale closed, the recorded sale price is shown; "asking" marks a price the home was listed at rather than what it sold for.

2025-12-16Sold — $3,850,000 asked $3,800,000 (this listing)MLS 24131109

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.

Year built1988
Living area460 sq ft
Lot size3.43 acres
Stories1
HeatTypical
ExteriorWood Shingles
Assessed value$1,963,220
Town appraisal$2,804,600
Last recorded sale2021 — $2,675,000

Recorded sales

Deed transfers on file with the New Canaan land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

Listing courtesy of Compass Connecticut, LLC — Christine Saxe · (203) 442-6626

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