77 Old Boston Road
Wilton, Connecticut 06897
Reduced from $2,499,000
- Beds
- 5
- Baths
- 5 | 2
- SqFt
- 7,993
- Acres
- 2.20
- Year Built
- 2000
- Neighborhood
- South Wilton
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Exceptional, elegant blend of timeless architecture, refined interiors, and extraordinary outdoor living built by Tomas Brothers. Professionally designed, fully irrigated gardens create a private, resort-like setting surrounding the home, with mature plantings and thoughtfully curated spaces that are as beautiful as they are inviting. Inside, gracious proportions and sophisticated details define the home, with five bedrooms, three ensuite baths, and a Jack-and-Jill bath providing exceptional comfort and flexibility. Five fireplaces create warmth and character throughout, including the luxurious primary suite, family room, private office, living room, and finished lower level. The heart of the home is for grand entertaining and comfortable everyday living, with beautifully appointed gathering spaces that flow effortlessly from one room to the next. The upper level has a media room, and a sitting room attached to the primary bedroom to serve as a nursery or studio. The finished lower level extends the living space, features its own fireplace and full bath, and is a potential in-law suite. A truly distinctive wine cellar, adorned with a hand-painted evocative mural inspired by Tuscany, provides an elegant setting for wine enthusiasts. Only 4 miles to the New Canaan train station for a fast commute to NYC. Close to major highways, shopping & restaurants.
Key Facts
- City/Town
- Wilton
- Neighborhood
- South Wilton
- Property / Style
- Single Family · Colonial
- Year Built
- 2000
- Days on Market
- 81 days
- Beds
- 5
- Baths
- 5 full · 2 half
- Living Area
- 7,993 sq ft
- Lot Size
- 2.20 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $36,459 / 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
$2.30M
vs $1.52M median
51.0% above median
Price / Sq Ft
$288
vs $423 median
31.9% below median
Days on Market
81 days
vs 38 days median
43 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
77 Old Boston Road, Wilton, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 12, 2026per month
- Principal & Interest$12,372
- Property Taxes$3,038
- Insurance$766
- 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
- 2000
- New Construction
- No/Resale
- Living Area
- 7,993 sq ft
- Below Grade
- 2,522 sq ft
Schools
- Elementary
- Miller-Driscoll
- Middle
- Cider Mill
- High
- Wilton
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 5
- Laundry
- Upper Level
- Appliances
- Electric CooktopConvection RangeWall OvenRefrigeratorSubzeroDishwasherWasherDryerWine Chiller
- Basement
- FullStorageCooledInterior AccessPartially FinishedWalk-outFull With Walk-Out
- In-Law Apartment
- PossibleLower LevelSeparate Entry
- Additional Rooms
- Bonus RoomSitting RoomWine Cellar
Exterior & Lot
- Lot Size
- 2.20 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Wood
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Garden AreaFrench DoorsUnderground SprinklerPatio
- Lot Description
- Lightly WoodedTreedSloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $36,459 / Annually
- Days on Market
- 81
- MLS #
- 24199612
- MLS Status
- Active
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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 5:05 AM UTC.