33 Sentry Hill Road
Roxbury, Connecticut 06783
Reduced from $1,649,000
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,716
- Acres
- 3.01
- Year Built
- 2002
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2002
- Days on Market
- 119 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 2,716 sq ft
- Lot Size
- 3.01 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $9,277 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
30
8 under contract
Median List Price
$1.30M
30 active listings
Median Closed Price
$1.40M
29 sales
Median Days on Market
88
30 active listings
Median $ / Sq Ft
$506
30 active listings
Sale-to-List Ratio
96.1%
29 sales
How this home compares
List Price
$1.55M
vs $1.30M median
19.4% above median
Price / Sq Ft
$570
vs $506 median
12.6% above median
Days on Market
119 days
vs 88 days median
31 days longer than median
Based on 30 active and 29 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 28, 2026.
Location
33 Sentry Hill Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$7,898
- Property Taxes$773
- Insurance$516
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Roxbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2002
- New Construction
- No/Resale
- Living Area
- 2,716 sq ft
Schools
- Elementary
- Booth Free
- High
- Shepaug
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Upper Level
- Appliances
- Gas CooktopWall OvenMicrowaveRefrigeratorFreezerIcemakerDishwasherWasherDryerWine Chiller
- Basement
- FullHeatedPartially FinishedFull With Walk-Out
- Interior Features
- Central Vacuum
- Additional Rooms
- FoyerMud Room
Exterior & Lot
- Lot Size
- 3.01 acres
- Zoning
- C
- Garage / Parking
- 2 garage spacesBarnDetached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- ClapboardWood
- Roof
- Wood ShingleGable
- Foundation
- Concrete
- Lot Description
- Open Lot
Listing & Financials
- Property Taxes
- $9,277 / Annually
- Days on Market
- 119
- MLS #
- 24163570
- MLS Status
- Active
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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 8:02 AM UTC.