557 Upper Grassy Hill Road
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,784
- Acres
- 2.73
- Year Built
- 1999
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to Upper Grassy Hill Living!
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Contemporary
- Year Built
- 1999
- Days on Market
- 119 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,784 sq ft
- Lot Size
- 2.73 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $13,082 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
24
27 under contract
Median List Price
$857,000
24 active listings
Median Closed Price
$582,500
88 sales
Median Days on Market
53
24 active listings
Median $ / Sq Ft
$296
24 active listings
Sale-to-List Ratio
99.0%
88 sales
How this home compares
List Price
$895,000
vs $857,000 median
In line with median
Price / Sq Ft
$237
vs $296 median
19.9% below median
Days on Market
119 days
vs 53 days median
66 days longer than median
Based on 24 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 29, 2026.
Location
557 Upper Grassy Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,563
- Property Taxes$1,090
- Insurance$298
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Contemporary
- Year Built
- 1999
- New Construction
- No/Resale
- Living Area
- 3,784 sq ft
- Below Grade
- 993 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Nonnewaug
Interior
- Heating
- Hot Air
- Heat Fuel
- OilPropane
- Cooling
- Central AirZoned
- Fireplaces
- 2
- Laundry
- Upper Level
- Laundry Location
- bedroom level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWine Chiller
- Basement
- FullHeatedFully FinishedCooledWalk-outLiveable SpaceFull With Walk-Out
- In-Law Apartment
- PossibleSeparate Entry
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - Pre-wiredOpen Floor PlanSecurity System
- Additional Rooms
- Bonus RoomFoyer
Exterior & Lot
- Lot Size
- 2.73 acres
- Zoning
- OS80
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- Safety FenceIn Ground Pool
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersFrench DoorsUnderground SprinklerPatio
- Lot Description
- Borders Open SpaceDryLevel LotSloping LotProfessionally LandscapedOpen Lot
Listing & Financials
- Property Taxes
- $13,082 / Annually
- Days on Market
- 119
- MLS #
- 24158380
- MLS Status
- Under Contract
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 7/29/2026. 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 7/29/2026 at 10:10 AM UTC.