About this home
Perched at the end of a peaceful South Wilton cul-de-sac, 43 Chessor Lane is a rare opportunity to own a custom-built masterpiece crafted by one of the area's most respected builders-for his own family. Designed with uncompromising quality and exceptional attention to detail, this home combines timeless elegance with cutting-edge technology for an elevated lifestyle. A new sweeping Belgian block-lined drive welcomes you to over 5,000 SF of refined living space, where thick crown moldings, coffered ceilings, and hand-finished millwork make a lasting impression. The sun-drenched chef's kitchen flows seamlessly into the family room, where a retractable projection screen and built-in surround sound create the ultimate home theater experience. A whole-house CAT 5 network, Control4 system, and six audio zones allow smart customization throughout. The primary suite features a spa-inspired bath, private sitting room, and balcony retreat. With five spacious bedrooms and 4.5 baths, every space is thoughtfully designed - with room for third floor expansion. A walk-out lower level with fireplace offers added living space and flexibility. Outside, professionally landscaped grounds offer room for pool, a bluestone patio, built-in fireplace, and intimate garden paths. Located within Wilton's award-winning school district and just minutes to shops, train, and town center-this home embodies both privacy and connection in one extraordinary setting.
Flood risk: check the FEMA flood map for this address.
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What's nearby
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.
| 2025-09-05 | Sold — $2,350,000 asked $2,250,000 (this listing) | MLS 24104186 |
Recorded sales
Deed transfers on file with the Wilton 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.
- 2006-05-08$2,075,000
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