Prevu by reAlpha
BuySellBlogBrowse Listings

249 Chestnut Hill RoadWilton, CT 06897

For Sale

$2,395,000

Smart Buyer Rebate $23,950

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...

Listed by Meghan Gatt

·

William Raveis Real Estate

·

(203) 904-8064

Listed by Carla Kupiec

·

William Raveis Real Estate

Last updated September 14, 2026

·

Source: SmartMLS #24206451

Listing Facts

  • TypeSingle-family
  • NeighborhoodWilton
  • Bedrooms5
  • Bathrooms7
  • Days on Prevu1
  • Taxes$30,752/year
  • Size8,685 sqft
  • Price per sqft$276

Location

Mortgage Calculator

Listing History

09/14/2026
Listed by William Raveis Real Estate
$2,395,000
  1. 09/14/2026$2,395,000
    Listed by William Raveis Real Estate

Property Details for 249 Chestnut Hill Road

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2008
  • Year Built Details: Public Records
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: French Doors, Patio

Features

  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Fence - Stone, Level Lot
  • Lot Size Acres: 1.00

Financial

Taxes

  • Parcel Number: 1923626
  • Tax Annual Amount: $30,752.00
  • Tax Year: 26

Interior

Features

  • Appliances: Cook Top, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
  • Fireplaces Total: 3

Measurements

  • Living Area: 6,380

Rooms

  • Basement: Full
  • Bathrooms Full: 5
  • Bathrooms Half: 2
  • Bathrooms Total Integer: 7
  • Bedrooms Total: 5
  • Rooms Total: 11

Parking

Parking

  • Attached Garage: Attached Garage
  • Garage Spaces: 3

Schools

Elementary School

  • Elementary School: Miller-Driscoll

High School

  • High School: Wilton

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Hot Air
  • Laundry Features: Upper Level
  • Sewer: Septic
  • Water Source: Private Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 7 bathrooms in this single-family home at 249 Chestnut Hill Road.

What schools are nearby to 249 Chestnut Hill Road?

Nearby schools include the Miller-Driscoll Elementary School and Wilton High School.

Does this single-family home have parking?

Yes, there are 3 parking spaces available for 249 Chestnut Hill Road.

What are the annual taxes for 249 Chestnut Hill Road?

Annual taxes for this single-family home are estimated at $30,752.

How does 249 Chestnut Hill Road compare to other single-family homes in Wilton?

This single-family home is listed 34% above the average price for single-family homes in Wilton and has been on the market for 70 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 8,685 sqft.

249 Chestnut Hill Road is a 5-bedroom, 7-bath single-family home for sale in Wilton CT 06897. Available on Prevu for 1 days at $2,395,000. This home features 8,685 square feet of living space, located in Wilton. The median listing price for single-family homes in this area is $1,299,500. Nearby schools include Miller-Driscoll Elementary School and Wilton High School. Explore more single-family home listings in Fairfield County.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.