58 Sheephill Road
Greenwich, Connecticut 06878
Reduced from $2,200,000
- Beds
- 4
- Baths
- 3 | 2
- SqFt
- 2,899
- Acres
- 0.24
- Year Built
- 1946
- Neighborhood
- Riverside
- 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
Welcome to 58 Sheephill Rd, a thoughtfully expanded and extensively updated home offering exceptional space and flexibility. The first floor features new flooring, updated kitchen cabinetry, backsplash, under-cabinet lighting, newer appliances, and a spacious in-law suite with a second kitchen, living area, bedroom, walk-in closet, and beautifully renovated full bath. The newly added second floor offers three bedrooms, wood flooring, a full hall bath, laundry room, generous storage, and a spacious primary suite with high ceilings, walk-in closet, and luxurious bath featuring double sinks and a large walk-in shower. The finished basement provides additional living space and a half bath. Outside, enjoy a new driveway and Belgium-block walkway, updated deck, fencing, siding, roof, and drainage system, plus beautifully landscaped front and rear gardens. Numerous mechanical and interior updates complete this impressive Riverside offering.
Key Facts
Market Snapshot
The Greenwich Market
Single Family · trailing 12 months
Active Listings
47
28 under contract
Median List Price
$3.60M
47 active listings
Median Closed Price
$2.64M
199 sales
Median Days on Market
51
47 active listings
Median $ / Sq Ft
$893
47 active listings
Sale-to-List Ratio
101.4%
199 sales
How this home compares
List Price
$1.75M
vs $3.60M median
51.4% below median
Price / Sq Ft
$604
vs $893 median
32.4% below median
Days on Market
52 days
vs 51 days median
In line with median
Based on 47 active and 199 closed sales (trailing 12 mo) of single family in Greenwich. Source: SmartMLS · As of November 7, 2026.
Location
58 Sheephill Road, Greenwich, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$9,484
- Property Taxes$943
- Insurance$583
- 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
- Colonial
- Year Built
- 1946
- New Construction
- No/Resale
- Living Area
- 2,899 sq ft
- Below Grade
- 422 sq ft
Schools
- Elementary
- Cos Cob
- High
- Greenwich
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Laundry
- Upper Level
- Appliances
- Gas CooktopOven/RangeMicrowaveRefrigeratorFreezerIcemakerDishwasherWasherDryer
- Basement
- FullHeatedStorageFully FinishedCooled
- In-Law Apartment
- YesFirst Floor
- Interior Features
- Cable - Pre-wired
Exterior & Lot
- Lot Size
- 0.24 acres
- Zoning
- R-12
- Garage / Parking
- 4 total parking spacesPavedDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedDeck
- Lot Description
- Fence - PartialTreedClearedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $11,319 / Annually
- Days on Market
- 52
- MLS #
- 24206943
- MLS Status
- Under Contract - Continue to Show
Similar Properties
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Co-Listed By
Anissa Paolillo
Redfin Corporation
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/7/2026. 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 11/7/2026 at 6:56 PM UTC.