33 Sentry Hill Road - Roxbury, CT

$1,595,000

Beds

4.00

Baths

2,716

SqFt

3.01

Acres

Pricing Insight: Originally listed for $1,649,000, the price was last adjusted to $1,595,000 on June 2, 2026, a –$54,000 (3.3%) change, approximately 0 days ago. This property has been on the market for approximately 63 days.

33 Sentry Hill Road, Roxbury, CT is a 4-bed, 4-bath, 2,716 square foot home built in 2002 , featuring colonial architecture.

This home is within the Roxbury school district. Local, with nearby schools including Booth Free.

MLS #: 24163570

Offered Price: $1,595,000

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 2,716 Sq. Ft.

Lot Size: 3.01 Acres

Neighborhood: N/A

County: Litchfield

Year Built: 2002

Design & Construction: Frame

Heating: Hot Air

Cooling: Central Air

Garage Spaces: 2

Price per Sq Ft as listed: $587

Estimated Tax: $9,277

Days on Market: 61

$30,900

6 Beds · 4 Baths · 2,716 Sq Ft

33 Sentry Hill Road, Roxbury

$885,000

2 Beds · 2 Baths · 1,543 Sq Ft

94 Judds Bridge Road, Roxbury

$2,200

1 Beds · 1 Baths · 900 Sq Ft

10 (LOWER) Sentry Hill Road, Roxbury

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Air

Fuel Tank Location: Above Ground

Cooling System: Central Air

Hot Water System: Domestic

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $587 / Sq. Ft.

Tax assessed value: $713,650

Estimated Tax: $9,277

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 2002

Living Area: 2,716 Sq. Ft.

Lot Size: 3.01 Acres

Fuel: Oil

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Roxbury
Statistical modeling algorithms

Local Market Context

Active Listings: 54

Average Price: $1,075,302

Average DOM: 61 days

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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!

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Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 3.0 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

54

Homes For Sale

$1,075,302

Average List Price

Mechanicals & Utilities: Hot Air • Oil • Central Air • Private Well water • 3 fireplaces

Exterior Features

Exterior Construction: Clapboard,Wood

Roof Type: Wood Shingle,Gable

Foundation: Concrete

Garage: Barn,Detached Garage (2 car)

Pool: Gunite,Heated,In Ground Pool

Utilities: Water: Private Well

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Real Estate Advisor

Roxbury • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

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(800) 555-0003

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Good morning Steve, I'm interested in
33 Sentry Hill Road, Roxbury, Connecticut

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