46 Grassy Hill Road
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,480
- Acres
- 3.50
- Year Built
- 1984
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Beautifully updated and impeccably maintained, this custom Colonial offers timeless New England charm in a private setting with gorgeous views of a picturesque waterfall and babbling brook. Set on beautifully landscaped grounds with an additional lot included, the home features wide-board hardwood floors, crown molding, custom built-ins, plantation shutters, French doors, and three fireplaces. The eat-in kitchen offers granite countertops, premium appliances, and opens to warm, inviting living spaces including formal living and dining rooms, a family room with fireplace, private den/office, and screened porch. The spacious primary suite includes a fireplace, walk-in closet, and ensuite bath, with three additional bedrooms and updated bathrooms. The finished walk-out lower level provides flexible space for a recreation room, gym, media room, or guests. Outdoor living is exceptional with a wraparound porch, Trex deck, extensive stone patios, mature landscaping, scenic trails, and the soothing sights and sounds of the cascading waterfall. A rare offering combining privacy, elegance, upgrades, and natural beauty just minutes from town.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1984
- Days on Market
- 25 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,480 sq ft
- Lot Size
- 3.50 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $11,769 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
26
26 under contract
Median List Price
$834,450
26 active listings
Median Closed Price
$587,500
88 sales
Median Days on Market
45
26 active listings
Median $ / Sq Ft
$302
26 active listings
Sale-to-List Ratio
99.0%
88 sales
How this home compares
List Price
$1.50M
vs $834,450 median
79.8% above median
Price / Sq Ft
$431
vs $302 median
42.7% above median
Days on Market
25 days
vs 45 days median
20 days fresher than median
Based on 26 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 28, 2026.
Location
46 Grassy Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$7,648
- Property Taxes$981
- Insurance$500
- 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
- Year Built
- 1984
- New Construction
- No/Resale
- Living Area
- 3,480 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 3
- Appliances
- Gas RangeMicrowaveSubzeroDishwasherWasherDryer
- Basement
- FullPartially FinishedWalk-out
Exterior & Lot
- Lot Size
- 3.50 acres
- Zoning
- OS80
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Walk to WaterView
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Asphalt ShingleMetal
- Foundation
- Concrete
- Exterior Features
- SidewalkTerracePorchGuttersStone WallPatio
- Lot Description
- Some WetlandsTreedLevel LotSloping LotWater ViewOpen Lot
Listing & Financials
- Property Taxes
- $11,769 / Annually
- Days on Market
- 25
- MLS #
- 24188752
- 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 7/28/2026. 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 7/28/2026 at 6:55 AM UTC.