2 Chieftans Road
Greenwich, Connecticut 06831
- Beds
- 4
- Baths
- 7 | 1
- SqFt
- 7,705
- Acres
- 1.39
- Year Built
- 1997
- 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
Exquisitely designed stone manor fronted by formal courtyard embraces 1.4 acres bordering conservation allowing for incredible privacy and expansive open views. Just beyond the private gates of the Chieftans enclave with 24-hr. security, on a peaceful tree-lined lane, the home's stunning open floor plan is the perfect combination of modern and traditional. High ceilings, intricate architectural detail and custom appointments. Indoor/outdoor entertaining flow with French doors in most main floor rooms to fabulous stone terrace spans the rear. Grand formal rooms, 3 fireplaces, library with wet bar, Christopher Peacock kitchen, 3-exposure family room, large rec room and multiple remote learning and office spaces. 4+ ensuite bedrooms. Main floor guest suite. Luxury primary wing features balcony with gorgeous vistas; two separate marble baths and walk-in custom closets. 3,000+ SF lower level ready for customization with exterior access. Perfect for those seeking a turnkey lifestyle and easy access to Greenwich and Westchester towns, golf, airport and private/public schools.
Key Facts
- City/Town
- Greenwich
- Property / Style
- Single Family · Colonial
- Year Built
- 1997
- Days on Market
- 1260 days
- Beds
- 4
- Baths
- 7 full · 1 half
- Living Area
- 7,705 sq ft
- Lot Size
- 1.39 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $25,587 / Annually
- HOA Fee
- $2,300 / Monthly
Market Snapshot
The Greenwich Market
Single Family · trailing 12 months
Active Listings
42
24 under contract
Median List Price
$3.54M
42 active listings
Median Closed Price
$2.40M
176 sales
Median Days on Market
43
42 active listings
Median $ / Sq Ft
$858
42 active listings
Sale-to-List Ratio
100.4%
176 sales
How this home compares
List Price
$3.85M
vs $3.54M median
8.9% above median
Price / Sq Ft
$500
vs $858 median
41.7% below median
Days on Market
1260 days
vs 43 days median
1217 days longer than median
Based on 42 active and 176 closed sales (trailing 12 mo) of single family in Greenwich. Source: SmartMLS · As of July 27, 2026.
Location
2 Chieftans Road, Greenwich, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$19,630
- Property Taxes$2,132
- Insurance$1,283
- HOA$2,300
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Greenwich
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1997
- Living Area
- 7,705 sq ft
Schools
- Elementary
- Parkway
- High
- Greenwich
Interior
- Heating
- Other
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Upper Level
- Basement
- Unfinished
- Interior Features
- Auto Garage Door OpenerCentral VacuumOpen Floor PlanSecurity System
- Additional Rooms
- Bonus RoomLaundry RoomMud Room
Exterior & Lot
- Lot Size
- 1.39 acres
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Construction
- Wood
- Roof
- Slate
- Foundation
- Concrete
- Lot Description
- Level Lot
HOA / Association
- Fee
- $2,300 / Monthly
Listing & Financials
- Property Taxes
- $25,587 / Annually
- Days on Market
- 1260
- MLS #
- 170549828
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
Listed By
Ellen Mosher
Houlihan Lawrence
Co-Listed By
Leslie Carlotti
Houlihan Lawrence
Buyer's Agent
Suzanne Katz
Sotheby's International Realty
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 2:20 PM UTC.