Skip to main content

50 Southbury Road

Roxbury, Connecticut 06783

ACTIVE$725,000
Beds
5
Baths
3
SqFt
1,365
Acres
2.00
Year Built
1817
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
WaterfrontGuest House1-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,346

per 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

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

Listed By

Jeffrey Phillips

(917) 284-8276

William Pitt Sotheby's Int'l

(860) 868-6600

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.