207 Grassy Hill Road
Woodbury, Connecticut 06798
- Beds
- 3
- Baths
- 2
- SqFt
- 1,844
- Acres
- 2.08
- Year Built
- 1993
- Neighborhood
- Grassy Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Nestled on a picturesque 2+ acre park-like setting, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and natural beauty-with the ease of one-level living. Designed with both style and functionality in mind, the sun-filled open layout is enhanced by vaulted ceilings, skylights, and elegant bay windows, creating a bright and airy atmosphere throughout. The heart of the home features a chef's kitchen with a large island that flows seamlessly into the family room, with stone gas fireplace making it perfect for both everyday living and entertaining and adds warmth and character. A formal dining room and living room offer additional space for gatherings. The main level includes a spacious primary suite with a full bath, along with two additional bedrooms and a full hall bath. Enjoy peaceful mornings and relaxing evenings in the charming three-season room overlooking the private, scenic grounds, surrounded by nature and tranquility. The finished lower level provides exceptional additional living space, complete with a second stone fireplace-ideal for a recreation room, home office, or guest retreat. Plenty of storage in the walk-up attic with expansion possibilities. Set in a serene country setting yet just minutes from shopping, dining, and commuter routes, this home truly offers the best of both worlds.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- Grassy Hill
- Property / Style
- Single Family · Ranch
- Year Built
- 1993
- Days on Market
- 54 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,844 sq ft
- Lot Size
- 2.08 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,554 / 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
$599,000
vs $857,000 median
30.1% below median
Price / Sq Ft
$325
vs $296 median
9.8% above median
Days on Market
54 days
vs 53 days median
In line with 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
207 Grassy Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,054
- Property Taxes$630
- Insurance$200
- 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
- Ranch
- Year Built
- 1993
- New Construction
- No/Resale
- Living Area
- 1,844 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Electric CooktopOven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullStorageInterior AccessPartially FinishedLiveable Space
- Interior Features
- Open Floor Plan
- Additional Rooms
- Workshop
Exterior & Lot
- Lot Size
- 2.08 acres
- Zoning
- OS80
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-EnclosedShedPorchGarden AreaLightingStone WallPatio
- Lot Description
- TreedLevel Lot
Listing & Financials
- Property Taxes
- $7,554 / Annually
- Days on Market
- 54
- MLS #
- 24173939
- MLS Status
- Under Contract
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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 11:50 AM UTC.