Richard Thomas

249 Chestnut Hill Road

Wilton, CT
$ 2,395,000 Beds 5 Baths 6 Sq 8,685
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 2,395,000
  • City
  • Wilton
  • Bedrooms
  • 5
  • Full Bathrooms
  • 5
  • County
  • Fairfield
  • Half Bathrooms
  • 2
  • Area
  • Lot Size
  • 1 Acres
  • Zip
  • 06897
  • Sqr Footage
  • 8,685
  • Year Built
  • 2008
  • Taxes
  • $ 30752
  • Style
  • MLS#
  • 24206451
Listed By: Meghan Gatt 203-904-8064 with William Raveis Real Estate. - (203) 854-5116
Data Source: Smart MLS

Features

General

Zoning R-2
Neighborhood South Wilton
County Fairfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
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 1
Year Built 2008
Style Colonial
Year Built Source Public Records

Interior Features

Cooling System Central Air
Total Rooms 11
Basement Description Full

Exterior Features

Water Source Private Well
Lot Description Fence - Stone,Level Lot
Color grey

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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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.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Miller-Driscoll Elementary School
Middle School Unknown Middle School
High School Wilton High School

Price History

9/14/2026 Listed $2,395,000

Property vs Zip Code Average in 06897

Price
AVG $1.79M
$2.4M
Taxes
AVG $21,533
$30,752
Year Built
AVG 1941
2008

In The Neighborhood

Areas That We Cover

249 Chestnut Hill Road Wilton, CT is a Single Family Home for sale at $2395000 with 8685 sqft and a lot size of 1 Acres Acre(s). 249 Chestnut Hill Road Wilton has 5 bedrooms, 5 baths and was built in 2008. The property's zip code is 06897 which is in Wilton, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: 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.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Richard Thomas

Richard Thomas

929-930-7343

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