323 Upper Grassy Hill Road
Woodbury, Connecticut 06798
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,066
- Acres
- 0.93
- Year Built
- 1986
- Neighborhood
- Grassy Hill
- 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 home! The details of this home are what make it unique. From the gigantic hydrangeas to the appetizing peach and pear trees, this home will continue to exceed expectations. Inside is remodeled and immaculate with the great elasticity that so many lack. The finely scaled rooms are so versatile, the home really allows you to figure out what works for you. For instance, the dining room, could be an office, the great room a dining room, you choose. Upstairs the bedrooms are a wonderful scale and ready for you to bring your toothbrush. Downstairs, this is where it really gets interesting! Downstairs is a clean and unfinished basement AND a huge room under the addition (which could be made into an in-law with separate entrance), with a deck outside. So much potential OR just enjoy as is! This home is truly a turn-key pleasure. Must see!
Key Facts
- City/Town
- Woodbury
- Neighborhood
- Grassy Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 1986
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,066 sq ft
- Lot Size
- 0.93 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $7,414 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
22
21 under contract
Median List Price
$885,000
22 active listings
Median Closed Price
$582,500
94 sales
Median Days on Market
62
22 active listings
Median $ / Sq Ft
$307
22 active listings
Sale-to-List Ratio
99.0%
94 sales
How this home compares
List Price
$589,000
vs $885,000 median
33.4% below median
Price / Sq Ft
$285
vs $307 median
7.2% below median
Days on Market
0 days
vs 62 days median
62 days fresher than median
Based on 22 active and 94 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of August 24, 2026.
Location
323 Upper Grassy Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per month
- Principal & Interest$3,025
- Property Taxes$618
- Insurance$196
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- Grassy Hill
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1986
- New Construction
- No/Resale
- Living Area
- 2,066 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Ceiling FansWall Unit
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Main floor
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasher
- Basement
- PartialPartial With Walk-Out
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Cable - AvailableOpen Floor Plan
- Additional Rooms
- Bonus RoomBreezewayExercise Room
Exterior & Lot
- Lot Size
- 0.93 acres
- Zoning
- OS80
- Garage / Parking
- 2 garage spaces4 total parking spacesAttached GarageOff Street ParkingDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- Gray
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $7,414 / Annually
- Days on Market
- 0
- MLS #
- 24200605
- MLS Status
- Coming Soon
- Financing
- FHA,CHFA
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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 8/24/2026. 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 8/24/2026 at 9:45 PM UTC.