249 Chestnut Hill Road
Wilton, Connecticut 06897
- Beds
- 5
- Baths
- 5 | 2
- SqFt
- 8,685
- Acres
- 1.00
- Year Built
- 2008
- Neighborhood
- South Wilton
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
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...
Key Facts
- City/Town
- Wilton
- Neighborhood
- South Wilton
- Property / Style
- Single Family · Colonial
- Year Built
- 2008
- Days on Market
- 61 days
- Beds
- 5
- Baths
- 5 full · 2 half
- Living Area
- 8,685 sq ft
- Lot Size
- 1.00 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $30,752 / Annually
Market Snapshot
The Wilton Market
Single Family · trailing 12 months
Active Listings
34
24 under contract
Median List Price
$1.52M
34 active listings
Median Closed Price
$1.39M
205 sales
Median Days on Market
38
34 active listings
Median $ / Sq Ft
$423
34 active listings
Sale-to-List Ratio
105.5%
205 sales
How this home compares
List Price
$2.40M
vs $1.52M median
57.3% above median
Price / Sq Ft
$276
vs $423 median
34.8% below median
Days on Market
61 days
vs 38 days median
23 days longer than median
Based on 34 active and 205 closed sales (trailing 12 mo) of single family in Wilton. Source: SmartMLS · As of November 14, 2026.
Location
249 Chestnut Hill Road, Wilton, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 12, 2026per month
- Principal & Interest$12,889
- Property Taxes$2,563
- Insurance$798
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Wilton
- Neighborhood
- South Wilton
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2008
- New Construction
- No/Resale
- Living Area
- 8,685 sq ft
- Below Grade
- 2,305 sq ft
Schools
- Elementary
- Miller-Driscoll
- High
- Wilton
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Upper Level
- Appliances
- Cook TopWall OvenRefrigeratorDishwasherWasherDryer
- Basement
- Full
- Additional Rooms
- FoyerGymLaundry RoomMud RoomSitting RoomWorkshop
Exterior & Lot
- Lot Size
- 1.00 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Shake
- Color
- grey
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- French DoorsPatio
- Lot Description
- Fence - StoneLevel Lot
Listing & Financials
- Property Taxes
- $30,752 / Annually
- Days on Market
- 61
- MLS #
- 24206451
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Carla Kupiec
William Raveis Real Estate
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/14/2026. This information 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 11/14/2026 at 4:55 AM UTC.