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1030 Washington Woodbury Road

Roxbury, Connecticut 06783

ACTIVE$1,949,000

Reduced from $2,475,000

Beds
4
Baths
4 | 1
SqFt
4,874
Acres
18.62
Year Built
1999
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Pool2-Car Garage4 FireplacesPrice Reduced

About This Home

NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong indoor-outdoor flow, the property offers immediate enjoyment and the flexibility to personalize over time. Now offered at a compelling new price, this is an exceptional opportunity to acquire a significant Roxbury estate with outstanding value in today's market.

Key Facts

City/Town
Roxbury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1999
Days on Market
205 days
Beds
4
Baths
4 full · 1 half
Living Area
4,874 sq ft
Lot Size
18.62 acres
Garage / Parking
2 garage
Property Taxes
$9,872 / Annually

Market Snapshot

The Roxbury Market

Single Family · trailing 12 months

Median Days on Market

89

31 active listings

Median $ / Sq Ft

$493

31 active listings

Sale-to-List Ratio

96.1%

28 sales

How this home compares

List Price

$1.95M

vs $1.29M median

50.5% above median

Price / Sq Ft

$400

vs $493 median

18.9% below median

Days on Market

205 days

vs 89 days median

116 days longer than median

Based on 31 active and 28 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 29, 2026.

Location

1030 Washington Woodbury Road, Roxbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,410

per month

  • Principal & Interest$9,937
  • Property Taxes$823
  • Insurance$650
  • 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
1999
New Construction
No/Resale
Living Area
4,874 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
4
Laundry Location
First Floor
Appliances
Gas RangeRefrigeratorDishwasherWasherDryer
Basement
PartialGarage Access
In-Law Apartment
No
Interior Features
Cable - Pre-wired

Exterior & Lot

Lot Size
18.62 acres
Zoning
C
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Pool
HeatedIn Ground Pool
Construction
Clapboard
Roof
Wood Shingle
Foundation
Concrete
Exterior Features
Porch-Wrap AroundBalconyTerraceHot TubStone Wall
Lot Description
Fence - PartialLightly WoodedSloping Lot

Listing & Financials

Property Taxes
$9,872 / Annually
Days on Market
205
MLS #
24146457
MLS Status
Active

Similar Properties

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

Listed By

Judith Auchincloss

(203) 770-3300

Klemm Real Estate Inc

(860) 868-7313

Co-Listed By

Jamie Marcoux

Klemm Real Estate Inc

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 10:10 AM UTC.