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2 Chieftans Road

Greenwich, Connecticut 06831

PENDING$3,850,000
Beds
4
Baths
7 | 1
SqFt
7,705
Acres
1.39
Year Built
1997
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

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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

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

Property + 5 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$25,345

per 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.