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46 Grassy Hill Road

Woodbury, Connecticut 06798

PENDING$1,500,000
Beds
4
Baths
3 | 1
SqFt
3,480
Acres
3.50
Year Built
1984
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage3 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,129

per 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

Homes with a close match in area, property type, and price.

Listed By

Timothy Drakeley

(203) 510-9184

Drakeley Real Estate, Inc.

(203) 263-4336

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.