249 Chestnut Hill Road Wilton, CT $ 2,395,000
249 Chestnut Hill Road
$ 2,395,000
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249 Chestnut Hill Road

Wilton, CT, 06897
$ 2,395,000
Bedrooms5 Baths5.2 Sq 8,685

Monthly Estimate*

$ 15,122

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Single Family Home for sale in Wilton, CT

for $2,395,000 with 5 bedrooms and 5 full baths, 2 half baths. This 8,685 square foot home was built in 2008 on a lot size of 1.

Sophisticated South Wilton Colonial: This Nantucket shingle-style residence blends timeless architectural elegance with seamless modern luxury, ideally positioned for effortless commuting to town, the train, and the Merritt Parkway. Thoughtfully designed for both grand entertaining and everyday comfort, the home features gorgeous custom details, extensive high-end upgrades, and an integrated three-zone surround sound system. The chef's kitchen is outfitted with premium appliances including a Viking six-burner gas cooktop, double ovens with a warming drawer, a built-in refrigerator, and a Miele dishwasher, opening directly into an inviting family room with custom built-ins and fireplace. On the main level, a sophisticated room provides versatile living space, seamlessly accommodating a formal dining room or private work space. Upstairs, the master bedroom serves as a luxurious private sanctuary with a cozy fireplace, a dedicated sitting area, expansive walk-in closets, and a spa-inspired primary bath. There are four additional bedrooms on this floor, two with ensuite bathrooms and two with a connected full-bath. The upper third level boasts a sixth bedroom suite and a large multi-generational living space with extensive built-ins, including cozy window-seating. The finished lower level provides an ideal versatile space featuring a spacious dedicated play/ game room, home gym, and a comfortable TV-watching area designed to grow right along with your kids... French doors off the kitchen and living room open seamlessly to an expansive bluestone patio with a large built-in Lynx grill with slate countertops and overlooking a flat, manicured lawn with exceptional privacy and space for a pool. This home is perfectly oriented on a ridge to capture both golden and pink sunrises and sunsets. Across the street is a favorite town-farm. The home has a high end reverse-osmosis water system and Generac 20-watt generator. Experience the perfect balance of refined craftsmanship and prime convenience in this exceptional South Wilton home.

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Single Family Contingent

Price

$ 2,395,000

Bedrooms

5

Full Bath

5

Half Bath

2

Property Type

Single Family

Taxes

$ 30,752

Style

Lot Size

1

Year Built

2008

Town/City

Wilton

MLS | Web ID

24206451

Features
General
Zoning R-2
Neighborhood South Wilton
County Fairfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Under Contract
Acres 1
Directions Wilton Road to Chestnut Hill Across from Offinger's Farm
High School Wilton
City Wilton
Elementary School Miller-Driscoll
Sq Ft Total 8685
DOM 17
Year Built 2008
Style Colonial
Year Built Source Public Records
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Interior
Cooling System Central Air
Total Rooms 11
Basement Description Full
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Exterior
Water Source Private Well
Lot Description Fence - Stone Level Lot
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* Excluded Features
List By
Meghan Gatt

Listing Agent

William Raveis Real Estate

Broker

meghan.gatt@raveis.com

Email

Affordability Calculator

$17,685
Per Month
86%
14%
0%
Monthly Principal & Interest
$15,122
Monthly Property Taxes
$2,563
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
1232684 Elementary School
4772591 Middle School
Wilton High School High School
Pricing History
DatePricePrice ChangeDescription
9/14/2026$2,395,000 Listed Price

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249 Chestnut Hill Road, Wilton, CT, 06897 is a Single Family Home for sale at $2,395,000 with 8,685 sqft and a lot size of 1. 249 Chestnut Hill Road has 5 bedrooms, 5.2 baths, and was built in 2008. The property's zip code is 06897 which is in Wilton, CT