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50 Southbury Road

Roxbury, Connecticut 06783

ACTIVE - NEW$950,000
Beds
5
Baths
3
SqFt
1,959
Acres
8.71
Year Built
1817
Matt Caiola

Matt Caiola

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WaterfrontGuest House1-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,796

per 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

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Listed By

Jeffrey Phillips

(917) 284-8276

William Pitt Sotheby's Int'l

(860) 868-6600

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.