• 4 days on site
  • 15 views

One of the most coveted enclaves in Fairfield County, WINDOVER, is a HOBI award-winning 8-home, 12-acre, private community just over the Wilton/Westport line. Highly sophisticated, designer-curated & professionally landscaped, this home is sited on one of the most private lots overlooking meadows, pond & near Cranbury park. A one-of-a-kind, primary or second residence AND HOA managed for a maintenance-free, Main-level living lifestyle. The stunning kitchen/great room area is swathed in natural light from the wall of sliders opening to the elevated bluestone patio w/ custom rail system. NEW private fenced courtyard off DR and rear fenced yard with owner-curated gardens. Every room is adorned w/ luxe, branded fixtures, appliances, & designer finishes. Subzero fridge + drawers, Wolf stovetop/oven & quartz-topped island overlooking the FR fireplace, wide-plank oak 7 floors, & sleek lines of custom trim work. The expansive butler's pantry incl: barn-style doors, custom cabinetry, wetbar, 2nd dishwasher, wine fridge & quartz tops. The primary suite is sumptuous w/ its vaulted ceilings, steam shower, radiant heated floor, soaking tub & WIC. Fully equipped laundry, mudroom & WIC complete the 1st floor. Upstairs, discover 2 well-proportioned BR suites w/ en-suite baths, plus light-filled office. 2 car garage w/ epoxy flooring & garage system from Garage Living. Just completed finished lower level w/ gym, office cedar closet & workshop. 3 Min to Westport shopping, train, dining.

Source: Smart MLS, MLS#: 24186977

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  • Property Type
    Residential
  • Lot
    0.31 acres

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Craig Milton

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Owning this Home

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

Life at 329 Chestnut Hill Road #5


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
6/25/2026Source: Smart MLS Added to Database
June 25, 2026
6/20/2022Source: Smart MLS Added to Database
September 13, 2021
Listing provided courtesy of William Raveis Real Estate- MLS# 24186977MLS ProviderContact Information: (203) 650-1583