28 Gregory Road
Greenwich, Connecticut 06807
Reduced from $2,150,000
- Beds
- 4
- Baths
- 3
- SqFt
- 3,597
- Acres
- 0.25
- Year Built
- 1959
- Neighborhood
- Cos Cob
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Opportunity awaits in one of Greenwich's most desirable communities. Located on a quiet residential street in Cos Cob, this spacious home offers 3,597 square feet of living space across two levels, featuring 4 bedrooms and 3 full bathrooms. A new roof and recently painted interior provide added value, while the generous floor plan offers exceptional flexibility for today's lifestyle. The generous footprint provides exceptional flexibility for modern living, entertaining, or future customization. Enjoy the benefits of Greenwich ownership, including access to top-rated schools, parks, beaches, and convenient proximity to Cos Cob village, Riverside, Old Greenwich, Metro-North, and major commuting routes. A rare chance to secure a substantial home in a sought-after Greenwich location.
Key Facts
Market Snapshot
The Greenwich Market
Single Family · trailing 12 months
Active Listings
45
16 under contract
Median List Price
$3.30M
45 active listings
Median Closed Price
$2.50M
216 sales
Median Days on Market
43
45 active listings
Median $ / Sq Ft
$869
45 active listings
Sale-to-List Ratio
100.7%
216 sales
How this home compares
List Price
$1.85M
vs $3.30M median
43.9% below median
Price / Sq Ft
$514
vs $869 median
40.9% below median
Days on Market
57 days
vs 43 days median
14 days longer than median
Based on 45 active and 216 closed sales (trailing 12 mo) of single family in Greenwich. Source: SmartMLS · As of September 11, 2026.
Location
28 Gregory Road, Greenwich, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$9,609
- Property Taxes$911
- Insurance$617
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1959
- New Construction
- No/Resale
- Living Area
- 3,597 sq ft
Schools
- Elementary
- North Mianus
- Middle
- Per Board of Ed
- High
- Greenwich
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- None
Exterior & Lot
- Lot Size
- 0.25 acres
- Zoning
- R-12
- Garage / Parking
- 1 garage space4 total parking spacesAttached GaragePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $10,929 / Annually
- Days on Market
- 57
- MLS #
- 24191798
- MLS Status
- Active
Similar Properties
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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 9/11/2026. 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 9/11/2026 at 8:50 PM UTC.