171 Proprietors Crossing
New Canaan, Connecticut 06840
Reduced from $2,795,000
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 5,532
- Acres
- 4.41
- Year Built
- 1981
- 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
Updated to perfection, this classic 5-bedroom Connecticut Colonial offers over 5,500 square feet of curated living space, harmoniously positioned on a private, sought-after cul-de-sac within an enclave of 4+ acre estates. The residence unfolds with a sun-drenched brand new chef's kitchen featuring custom cabinetry, premium quartz countertops, and high-end appliances, all flowing through floor-to-ceiling glass sliders to an expansive deck and a grand family room anchored by a stately fireplace. A sophisticated main level offers a formal dining room, elegant living room, and a bespoke private office with picturesque views of the park-like grounds. Upstairs, the primary suite serves as a sanctuary with a dedicated sitting room and new spa-inspired bath, while a separate private-entry in-law suite provides a secluded fifth bedroom and sitting area for ultimate versatility. The newly finished 1,700-square-foot walk-out lower level elevates entertaining with a massive media/playroom, an additional family room, and potential for a custom wine cellar-all just minutes from the vibrant New Canaan town center, top-tier schools, and the Metro-North train.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1981
- Days on Market
- 80 days
- Beds
- 5
- Baths
- 3 full · 1 half
- Living Area
- 5,532 sq ft
- Lot Size
- 4.41 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $17,381 / Annually
Market Snapshot
The New Canaan Market
Single Family · trailing 12 months
Active Listings
34
51 under contract
Median List Price
$3.02M
34 active listings
Median Closed Price
$2.74M
212 sales
Median Days on Market
41
34 active listings
Median $ / Sq Ft
$658
34 active listings
Sale-to-List Ratio
100.6%
212 sales
How this home compares
List Price
$2.50M
vs $3.02M median
17.5% below median
Price / Sq Ft
$451
vs $658 median
31.5% below median
Days on Market
80 days
vs 41 days median
39 days longer than median
Based on 34 active and 212 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of July 27, 2026.
Location
171 Proprietors Crossing, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$12,721
- Property Taxes$1,448
- Insurance$832
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Canaan
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1981
- New Construction
- No/Resale
- Living Area
- 5,532 sq ft
- Below Grade
- 1,700 sq ft
Schools
- Elementary
- West
- High
- New Canaan
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- Main floor off kitchen
- Appliances
- Electric RangeOven/RangeWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullFully FinishedGarage AccessWalk-outLiveable Space
- In-Law Apartment
- PossibleSecond Floor
- Interior Features
- Auto Garage Door OpenerCentral Vacuum
- Additional Rooms
- FoyerSitting Room
Exterior & Lot
- Lot Size
- 4.41 acres
- Zoning
- 4AC
- Garage / Parking
- 2 garage spacesUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersLightingFrench DoorsPatio
- Lot Description
- On Cul-De-Sac
Listing & Financials
- Property Taxes
- $17,381 / Annually
- Days on Market
- 80
- MLS #
- 24169441
- MLS Status
- Active
Similar Properties
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Co-Listed By
Kendall Sneddon
William Pitt Sotheby's Int'l
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. 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 7/27/2026 at 10:05 PM UTC.