143 Chestnut Hill Road
Wilton, Connecticut 06897
- Beds
- 6
- Baths
- 6 | 1
- SqFt
- 5,455
- Acres
- 2.45
- Year Built
- 1900
- Neighborhood
- South Wilton
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
A beautifully preserved historic treasure, 143 Chestnut Hill blends more than a century of character with extraordinary craftsmanship and modern-day function. Built in 1900, with just three owners and lovingly curated by the current owners for over 40 years, the home has been thoughtfully expanded while honoring its original wide-board floors, stonework, doors, millwork and reclaimed antique beams. Throughout, extensive custom cabinetry was designed specifically for each room, with inset dressers, drawers, armoires and ingenious storage creating a true place for everything. At the heart of the home is a spectacular chef's kitchen with a 7ft island topped in reclaimed white oak, 48" Bertazzoni range, Danby marble, Sub-Zero refrigerator, and Rohl Shaw sinks. Gracious living spaces include an oversized dining room, sunroom with authentic stone wall and beams, family room with original stone fireplace and mudroom with travertine floors. A main-level en-suite bedroom and elevator provides exceptional flexibility for a first-floor bedroom suite. Upstairs, you will find a light-filled vaulted primary suite featuring extensive built-ins, walk-in closet and luxurious bath, plus five add'l bedrooms. The finished walk-out lower level adds versatility with a playroom, kitchenette, office/bedroom and full bath. Outdoors, enjoy a wraparound mahogany deck, bluestone patio, stone fire pit, plus an extraordinary approx. 2,500 SF heated/cooled barn w/ office, kitchenette, bedroom...and more!
Key Facts
- City/Town
- Wilton
- Neighborhood
- South Wilton
- Property / Style
- Single Family · Colonial
- Year Built
- 1900
- Days on Market
- 0 days
- Beds
- 6
- Baths
- 6 full · 1 half
- Living Area
- 5,455 sq ft
- Lot Size
- 2.45 acres
- Garage / Parking
- 2 garage · 10 total
- Property Taxes
- $18,764 / Annually
Market Snapshot
The Wilton Market
Single Family · trailing 12 months
Active Listings
36
19 under contract
Median List Price
$1.67M
36 active listings
Median Closed Price
$1.41M
214 sales
Median Days on Market
18
36 active listings
Median $ / Sq Ft
$427
36 active listings
Sale-to-List Ratio
105.5%
214 sales
How this home compares
List Price
$2.38M
vs $1.67M median
42.0% above median
Price / Sq Ft
$435
vs $427 median
In line with median
Days on Market
0 days
vs 18 days median
18 days fresher than median
Based on 36 active and 214 closed sales (trailing 12 mo) of single family in Wilton. Source: SmartMLS · As of September 23, 2026.
Location
143 Chestnut Hill Road, Wilton, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$12,577
- Property Taxes$1,564
- Insurance$792
- 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
- 1900
- New Construction
- No/Resale
- Living Area
- 5,455 sq ft
- Below Grade
- 1,207 sq ft
Schools
- Elementary
- Miller-Driscoll
- Middle
- Cider Mill
- High
- Wilton
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Lower LevelMain Level
- Laundry Location
- Mud Room and Second Set in Lower Level
- Appliances
- Gas RangeMicrowaveRefrigeratorSubzeroDishwasherWasherDryer
- Basement
- FullHeatedFully FinishedCooledFull With Walk-Out
- In-Law Apartment
- YesLower Level
- Interior Features
- ElevatorOpen Floor Plan
- Additional Rooms
- FoyerLaundry RoomMud RoomWorkshop
- Accessibility
- Accessible Bath,Roll-In Shower
Exterior & Lot
- Lot Size
- 2.45 acres
- Zoning
- R-2
- Garage / Parking
- 2 garage spaces10 total parking spacesDetached GaragePavedDrivewayPrivatePavedAsphaltGravel
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- ShingleClapboard
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- Wrap Around DeckBarnFrench DoorsPatioShedDeckGarden AreaStone WallUnderground Sprinkler
- Lot Description
- Corner LotLightly WoodedLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $18,764 / Annually
- Days on Market
- 0
- MLS #
- 24208606
- MLS Status
- Coming Soon
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Co-Listed By
Penny Schwartz
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 9/23/2026. 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 9/23/2026 at 11:05 PM UTC.