233 Southbury Road
Roxbury, Connecticut 06783
- Beds
- 5
- Baths
- 6
- SqFt
- 5,447
- Acres
- 10.05
- Year Built
- 1988
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
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
$1.79M
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.