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207 Grassy Hill Road

Woodbury, Connecticut 06798

PENDING$599,000
Beds
3
Baths
2
SqFt
1,844
Acres
2.08
Year Built
1993
Matt Caiola

Matt Caiola

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2-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,884

per 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

Similar Properties

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Listed By

Laura Brodie

(203) 733-0679

Coldwell Banker Realty

(203) 438-9000

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.