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233 Southbury Road

Roxbury, Connecticut 06783

ACTIVE$1,795,000
Beds
5
Baths
6
SqFt
5,447
Acres
10.05
Year Built
1988
Matt Caiola

Matt Caiola

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Waterfront3-Car Garage4 Fireplaces

About This Home

Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

Key Facts

City/Town
Roxbury
Neighborhood
N/A
Property / Style
Single Family · Modern,Tudor
Year Built
1988
Days on Market
22 days
Beds
5
Baths
6 full
Living Area
5,447 sq ft
Lot Size
10.05 acres
Garage / Parking
3 garage · 8 total
Property Taxes
$18,701 / Annually

Market Snapshot

The Roxbury Market

Single Family · trailing 12 months

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

$1.79M

vs $1.30M median

38.3% above median

Price / Sq Ft

$330

vs $506 median

34.8% below median

Days on Market

22 days

vs 88 days median

66 days fresher 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

233 Southbury Road, Roxbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,308

per month

  • Principal & Interest$9,152
  • Property Taxes$1,558
  • Insurance$598
  • 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
Modern,Tudor
Year Built
1988
New Construction
No/Resale
Living Area
5,447 sq ft

Schools

Elementary
Booth Free
Middle
Regional District 12
High
Regional District 12

Interior

Heating
Hot Water
Heat Fuel
OilPropane
Cooling
Central Air
Fireplaces
4
Laundry
Main Level
Laundry Location
Main
Appliances
Oven/RangeRange HoodRefrigerator
Basement
FullApartmentPartially FinishedWalk-outLiveable SpaceConcrete FloorFull With Walk-Out
In-Law Apartment
YesLower Level
Interior Features
Auto Garage Door OpenerOpen Floor Plan
Additional Rooms
FoyerSitting RoomStaff Quarters

Exterior & Lot

Lot Size
10.05 acres
Zoning
C
Garage / Parking
3 garage spaces8 total parking spacesAttached GaragePavedDrivewayPrivateCircularPaved
Waterfront
Direct waterfront
Waterfront Details
BrookAccess
Water Source
Private Well
Sewer
Septic
Construction
WoodStucco
Color
Cream
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
BalconyDeckStone WallFrench Doors
Lot Description
SecludedSome WetlandsLevel LotRollingOpen Lot

Listing & Financials

Property Taxes
$18,701 / Annually
Days on Market
22
MLS #
24189301
MLS Status
Active

Similar Properties

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

Listed By

Kathryn Clair

(203) 948-5255

William Pitt Sotheby's Int'l

(860) 868-6600

Co-Listed By

Kathryn Bassett

William Pitt Sotheby's Int'l

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 7:50 AM UTC.