50 Southbury Road
Roxbury, Connecticut 06783
- Beds
- 5
- Baths
- 3
- SqFt
- 1,959
- Acres
- 8.71
- Year Built
- 1817
- 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
* A beautiful 3-bedroom historic farmhouse * A separate 2-bedroom guest house * A pristine 6.71-acre building lot Move in and enjoy lush, pastoral Roxbury right away in the charming and immaculate 3-bedroom, c. 1817 main house, and host family and guests in the separate 2-bedroom guest house. The adjacent 6.71-acre parcel at the rear lets you protect your views and privacy forever. You can also build the 4-bedroom estate of your dreams on this approved building lot, with its own driveway and road access. Or use the mostly flat lot as an orchard or garden, or hold the separate parcel as an investment to sell in the future. The lot abuts preserved land. Located in southern Roxbury, just 90 minutes from New York City, the main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. A brand-new standing-seam metal roof carries a lifetime guarantee. At the heart of the house is a spacious eat-in kitchen. On one side are a formal dining room and a library, and on the other is a sunlit double living room wrapped in windows. The 658-square-foot guest house overlooks a spring-fed pond and Little Jacks Brook. It has a generous living room, two bedrooms, and a full bath, and it runs on its own well and septic system. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and a gently rolling lawn.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1817
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 1,959 sq ft
- Lot Size
- 8.71 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $4,879 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
25
5 under contract
Median List Price
$1.29M
25 active listings
Median Closed Price
$1.12M
28 sales
Median Days on Market
92
25 active listings
Median $ / Sq Ft
$485
25 active listings
Sale-to-List Ratio
95.9%
28 sales
How this home compares
List Price
$950,000
vs $1.29M median
26.6% below median
Price / Sq Ft
$485
vs $485 median
In line with median
Days on Market
0 days
vs 92 days median
92 days fresher than median
Based on 25 active and 28 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of September 26, 2026.
Location
50 Southbury Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$5,072
- Property Taxes$407
- Insurance$317
- 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
- Cape Cod
- Year Built
- 1817
- New Construction
- No/Resale
- Living Area
- 1,959 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Electric
- Cooling
- None
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- laundry in guest house
- Appliances
- Gas RangeRefrigeratorDishwasherWasherDryer
- Basement
- Partial
- In-Law Apartment
- PossibleDetached
Exterior & Lot
- Lot Size
- 8.71 acres
- Zoning
- A
- Garage / Parking
- 1 garage spaceDetached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- PondWalk to Water
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Wood
- Roof
- Wood Shingle
- Foundation
- BlockStone
- Exterior Features
- DeckGarden AreaGuest HouseStone WallPatio
- Lot Description
- Lightly WoodedSloping Lot
Listing & Financials
- Property Taxes
- $4,879 / Annually
- Days on Market
- 0
- MLS #
- 24209875
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/26/2026. 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 9/26/2026 at 11:15 PM UTC.