George Cress of Real Broker Email: george@cress.co (dot co) Call/Text: 212-203-5251
New Canaan, CT / SOLD
469 Brookside RoadNew Canaan, CT 06840
The buyer could have saved $48,125 in 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 50% rebate. Actual savings depend on final purchase price and commission received. Based on the recorded closed price; this is a hypothetical estimate, not a statement of actual commission or rebate paid.
Sale Price$3,850,000ClosedDecember 15, 2025
Open house
Our Take
469 Brookside Road, known as “Shadowlyn,” dates to the 1820s and combines vintage details with modern amenities. The six-bedroom main residence includes four fireplaces, an expansive kitchen with a family room and oversized mudroom, formal living and dining spaces, a library, and a primary suite with an updated bath. Set on 3.43 acres, the property includes a pool, pool house, tennis court, and garage/barn with an apartment above. It is convenient to downtown New Canaan, Darien, and Norwalk.
At a glance
Closed · MLS #24131109- Bedrooms
- 6
- BathroomsBaths
- 5 full / 0 half
- Square feet
- 5,275
- Year built
- 1820
- Acres
- 3.43
- Property taxes
- $32,766
July 2025-June 2026
What stands out
- Six-bedroom main residence with four fireplaces
- Kitchen with large island and vintage wet bar
- Formal rooms with high ceilings and conversation alcoves
- Library with French doors to the terrace
- Primary suite with walk-in closet and updated bath
- Pool, pool house, and tennis court
- Garage/barn with apartment above
- Illuminated landscaping across the estate
Read the full listing 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.
Schools
- Elementary
- South
- Middle
- Not provided
- High
- New Canaan
Schools as reported by SmartMLS. Confirm attendance assignments with the district.
Price history
| Date | Event | Price |
|---|---|---|
| Closed price | $3,850,000 | |
| Original list price | $3,800,000 |
Intermediate price changes and previous listings may not be included.
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Nearby sold homes
View sold homes in New Canaan →
Sold 11/05/23
$2,125,0004 beds · 4 ba · 3,423 sqft · Sold446 Brookside Road, New Canaan, CT 06840William Raveis Real Estate
Sold 10/18/23
$3,550,0005 beds · 6 ba · 6,390 sqft · Sold185 Charter Oak Drive, New Canaan, CT 06840Houlihan Lawrence
Sold 02/22/23
$2,329,0005 beds · 5 ba · 5,046 sqft · Sold587 Brookside Road, New Canaan, CT 06840William Pitt Sotheby's Int'l
Sold 01/10/24
$1,662,5006 beds · 5 ba · 5,248 sqft · Sold142 White Birch Road, New Canaan, CT 06840Outlook Realty
Sold 08/20/23
$4,150,0006 beds · 8.5 ba · 9,914 sqft · Sold35 Charter Oak Lane, New Canaan, CT 06840William Raveis Real Estate
*Estimate: $3,850,000 closed price × assumed 2.5% buyer-agent commission × 50% rebate = $48,125. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered or actual compensation. This is a hypothetical estimate, not a rebate paid on this sale.
Listed by Compass Connecticut, LLC · (203) 442-6626
Christine Saxe · (203) 273-1548
SmartMLS · Listing #24131109 · Closed
Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.
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