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$2,395,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 2 Partial Baths
  • 8,685 Sq. Ft.
  • 3 Car Garage
  • Updated 13 hours ago
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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...

Full Property Details for 249 Chestnut Hill Rd

General

  • Price: $2,395,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24206451
  • Updated: 9/14/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 11
  • Rooms/Areas: Foyer, Gym, Laundry Room, Mud Room, Sitting Room, Workshop
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Cook Top, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 5
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Vaulted Ceiling, Built-Ins, Dressing Room, Fireplace, , Upper
  • Bedroom 1: Bedroom - 9 ft+ Ceilings, Built-Ins, Jack & Jill Bath, Walk-In Closet, Hardwood Floor, Upper
  • Bedroom 2: Bedroom - 9 ft+ Ceilings, Built-Ins, Full Bath, Walk-In Closet, Hardwood Floor, Upper
  • Bedroom 3: Bedroom - 9 ft+ Ceilings, Full Bath, Walk-In Closet, Hardwood Floor, Upper
  • Bedroom 4: Bedroom - 9 ft+ Ceilings, Built-Ins, Jack & Jill Bath, Walk-In Closet, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Fireplace, Hardwood Floor, Main
  • Great Room: Great Room - Book Shelves, Built-Ins, Wall/Wall Carpet, Hardwood Floor, On 3rd Floor, Upper
  • Family Room: Family Room - 9 ft+ Ceilings, Book Shelves, Built-Ins, Fireplace, Hardwood Floor, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, Built-Ins, Granite Counters, Dining Area, Island, Hardwood Floor, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Hardwood Floor, Main
  • Library: Library - 9 ft+ Ceilings, Built-Ins, Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Built-Ins, Lower
  • Rec Room: Built-Ins, Lower
  • Laundry: Upper Level
  • Other Room 1: Other - Full Bath, Upper

Exterior

  • Exterior Features: French Doors, Patio
  • Color: grey

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: South Wilton
  • Driving Directions: Wilton Road to Chestnut Hill Across from Offinger's Farm

School Information

  • Elementary School: Miller-Driscoll
  • High School: Wilton

Community

  • Community Name: South Wilton

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Shake
  • Basement Desc.: Full
  • Roof: Asphalt Shingle
  • Square Feet: 8,685
  • Above Ground: 6,380 Sq. Ft.
  • Below Ground: 2,305 Sq. Ft.
  • Year Built: 2008

Lot Features

  • Lot Size (Acres): 1
  • Zoning: R-2
  • Lot Description: Fence - Stone, Level Lot

Financial Considerations

  • Assessment Amount: $1,227,030
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 1923626

Listed by William Raveis Real Estate, The Gatt Team at William Raveis Real Estate, Meghan Gatt and William Raveis Real Estate, Carla Kupiec

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Listing agents

— 249 Chestnut Hill Rd —

  • Meghan Gatt

    William Raveis Real Estate

  • Carla Kupiec

    William Raveis Real Estate

Agent Contact: (203) 904-8064 Office Contact: (203) 854-5116

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 249 Chestnut Hill Rd

School District:Wilton School District
NameGradesDistance
Miller-Driscoll School
217 Wolfpit Road, Wilton, CT 06897
PK-22.1 mi
Cider Mill School
240 School Road, Wilton, CT 06897
3-52.2 mi
Middlebrook School, Wilton, CT
131 School Road, Wilton, CT 06897
6-82.3 mi
Wilton High School
395 Danbury Road, Wilton, CT 06897
9-122.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 249 Chestnut Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/14/2026
Listed
$2,395,000
49.69%
MLS
6/19/2013
Sold
$1,600,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 249 Chestnut Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$29,952
2%
$1,227,030
—
2023
$29,375
3%
$1,227,030
26%
2023
$28,474
4%
$973,140
—
2022
$27,472
1%
$973,140
—
2021
$27,121
1%
$973,140
—
2020
$26,722
-4%
$973,140
—
2019
$27,773
-13%
$973,140
-14%
2018
$32,035
2%
$1,136,380
—
2017
$31,557
2%
$1,136,380
—
2016
$31,069
3%
$1,136,380
1%
2015
$30,183
4%
$1,124,970
2%
2014
$29,142
2%
$1,099,280
—
2011
$28,570
—
$1,099,280
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by William Raveis Real Estate, The Gatt Team at William Raveis Real Estate, Meghan Gatt and William Raveis Real Estate, Carla Kupiec

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249 Chestnut Hill Road, Wilton, CT 06897 (MLS# 24206451) is a Single Family property with 5 bedrooms, 5 full bathrooms and 2 partial bathrooms. 249 Chestnut Hill Road is currently listed for $2,395,000 and was received on September 14, 2026. Want to learn more about 249 Chestnut Hill Road? Do you have questions about finding other Single Family real estate for sale in Wilton? You can browse all Wilton real estate or contact a Coldwell Banker agent to request more information.

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