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74 Glenville Road

Greenwich, Connecticut 06831

ACTIVE$4,390,000

Reduced from $4,500,000

Beds
5
Baths
5 | 1
SqFt
4,937
Acres
1.92
Year Built
1921
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage3 FireplacesPrice Reduced

About This Home

A Greenwich classic, this distinguished five-bedroom residence combines timeless architecture, exceptional craftsmanship, and grand-scale rooms designed for both entertaining and everyday living. Perched high above sweeping, beautifully landscaped grounds, the home enjoys a commanding setting with privacy, mature plantings, and expansive westerly views across the property. A slate roof, custom millwork, multiple fireplaces, and graciously proportioned interiors further reflect the home's enduring character. Elegant formal living and dining rooms are complemented by a Christopher Peacock kitchen with adjoining breakfast room, a comfortable family room, and a library or private office. Upstairs, the spacious primary suite is joined by three additional bedrooms, two of which are en suite. A fifth bedroom and flexible living space on the lower level provide additional accommodations. Expansive terraces extend the living spaces outdoors, overlooking the sweeping grounds and putting green, while a circular drive creates an impressive approach. A rare combination of scale, privacy, and setting, just minutes from central Greenwich.

Key Facts

City/Town
Greenwich
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1921
Days on Market
45 days
Beds
5
Baths
5 full · 1 half
Living Area
4,937 sq ft
Lot Size
1.92 acres
Garage / Parking
2 garage
Property Taxes
$18,955 / Annually

Market Snapshot

The Greenwich Market

Single Family · trailing 12 months

Median Days on Market

34

53 active listings

Median $ / Sq Ft

$859

53 active listings

Sale-to-List Ratio

101.3%

205 sales

How this home compares

List Price

$4.39M

vs $3.25M median

35.1% above median

Price / Sq Ft

$889

vs $859 median

In line with median

Days on Market

45 days

vs 34 days median

11 days longer than median

Based on 53 active and 205 closed sales (trailing 12 mo) of single family in Greenwich. Source: SmartMLS · As of October 12, 2026.

Location

74 Glenville Road, Greenwich, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$27,359

per month

  • Principal & Interest$24,316
  • Property Taxes$1,580
  • Insurance$1,463
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Greenwich
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1921
New Construction
No/Resale
Living Area
4,937 sq ft

Schools

Elementary
Glenville
High
Greenwich

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
3
Laundry
Lower Level
Appliances
Gas RangeWall OvenMicrowaveSubzeroWasherDryer
Basement
FullFull With Walk-Out
Interior Features
Auto Garage Door Opener

Exterior & Lot

Lot Size
1.92 acres
Zoning
RA-1
Garage / Parking
2 garage spacesUnder House Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Shingle
Roof
Slate
Foundation
Masonry
Lot Description
Lightly WoodedTreedProfessionally LandscapedRolling

Listing & Financials

Property Taxes
$18,955 / Annually
Days on Market
45
MLS #
24202628
MLS Status
Active

Similar Properties

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Listed By

Chelsea Hammerschmidt

(203) 832-8706

William Pitt Sotheby's Int'l

(203) 655-8234

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/12/2026. 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 10/12/2026 at 11:30 PM UTC.