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
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About This Home
Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks the spring-fed pond and includes a generous living room, two bedrooms, and a full bath-serviced by its own septic. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and gently rolling lawn. This charming home blends history, potential, and natural beauty in one of Litchfield County's most coveted locations., Additional acreage available- separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. Total square footage is combined main house and guest house.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1817
- Days on Market
- 63 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
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
$725,000
vs $1.30M median
44.1% below median
Price / Sq Ft
$531
vs $506 median
In line with median
Days on Market
63 days
vs 88 days median
25 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
50 Southbury Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,697
- 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
- 63
- 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 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 1:10 PM UTC.