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103 Hollow Road

Watertown, Connecticut 06795

PENDING$375,000
Beds
3
Baths
2
SqFt
1,747
Acres
0.69
Year Built
1952
Matt Caiola

Matt Caiola

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4-Car Garage1 Fireplace

About This Home

Set in a desirable location, this Watertown home offers a flexible layout and a great opportunity to make it your own. The main level includes a comfortable living room with a pellet stove, an eat-in kitchen with generous cabinet space and backyard views, a family room, a main floor bedroom, and an updated full bath. Upstairs, there are two additional bedrooms, providing a practical separation of space. The finished lower level adds extra versatility with its own kitchen and full bath, suitable for extended family, guests, or other uses. Outside, the property features a level backyard and ample garage space, including a two-car attached garage and an additional two-car garage below. A newer well provides added peace of mind. Set on a quiet, private road, the location offers easy access to local amenities, including Watertown Golf Club, Hawk Ridge Winery, downtown Watertown, and nearby Litchfield. A solid option for buyers seeking space, functionality, and the chance to add personal touches over time. Property to be sold as-is.

Key Facts

City/Town
Watertown
Neighborhood
N/A
Property / Style
Single Family · Cape Cod
Year Built
1952
Days on Market
130 days
Beds
3
Baths
2 full
Living Area
1,747 sq ft
Lot Size
0.69 acres
Garage / Parking
4 garage
Property Taxes
$7,179 / Annually

Market Snapshot

The Watertown Market

Single Family · trailing 12 months

Median Days on Market

45

29 active listings

Median $ / Sq Ft

$257

29 active listings

Sale-to-List Ratio

100.0%

207 sales

How this home compares

List Price

$375,000

vs $429,999 median

12.8% below median

Price / Sq Ft

$215

vs $257 median

16.3% below median

Days on Market

130 days

vs 45 days median

85 days longer than median

Based on 29 active and 207 closed sales (trailing 12 mo) of single family in Watertown. Source: SmartMLS · As of July 28, 2026.

Location

103 Hollow Road, Watertown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,635

per month

  • Principal & Interest$1,912
  • Property Taxes$598
  • Insurance$125
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Watertown
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Single Family
Style
Cape Cod
Year Built
1952
New Construction
No/Resale
Living Area
1,747 sq ft

Schools

Elementary
John Trumbull
Middle
Judson
High
Watertown

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
None
Fireplaces
1
Laundry
Lower Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullStoragePartially FinishedWalk-outLiveable Space
In-Law Apartment
PossibleLower Level
Interior Features
Auto Garage Door OpenerCable - Pre-wired

Exterior & Lot

Lot Size
0.69 acres
Zoning
R70
Garage / Parking
4 garage spacesAttached GarageUnder House Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Color
White
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
GuttersGarden AreaLighting
Lot Description
Lightly WoodedCleared

Listing & Financials

Property Taxes
$7,179 / Annually
Days on Market
130
MLS #
24159949
MLS Status
Under Contract - Continue to Show

Similar Properties

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

Listed By

Taylor O'Keefe-Hamel

(203) 578-5388

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 6:15 AM UTC.