50 Southbury Road
Roxbury, Connecticut 06783
- Beds
- 5
- Baths
- 3
- SqFt
- 1,365
- Acres
- 2.00
- 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
Move in and immediately enjoy lush pastoral Roxbury in the charming and immaculate 3 bedroom c.1817 main house, while entertaining guests and family in the separate 2 bedroom guest house. Located in pastoral 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. It has a brand new metal standing seam roof with a lifetime guarantee. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a double sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks a spring-fed pond and Little Jacks Brook, and includes a generous living room, two bedrooms, and a full bath-serviced by its own well, septic & garage. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and gently rolling lawn.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1817
- Days on Market
- 123 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 1,365 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $4,879 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
24
5 under contract
Median List Price
$1.38M
24 active listings
Median Closed Price
$1.12M
28 sales
Median Days on Market
97
24 active listings
Median $ / Sq Ft
$480
24 active listings
Sale-to-List Ratio
95.9%
28 sales
How this home compares
List Price
$725,000
vs $1.38M median
47.5% below median
Price / Sq Ft
$531
vs $480 median
10.6% above median
Days on Market
123 days
vs 97 days median
26 days longer than median
Based on 24 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$3,870
- Property Taxes$407
- Insurance$242
- 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
- 1,365 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
- 2.00 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
- 123
- MLS #
- 24178189
- MLS Status
- Active
Similar Properties
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Co-Listed By
Mark Madonna
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 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 12:35 AM UTC.