268 South Street
Roxbury, Connecticut 06783
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 6,190
- Acres
- 41.00
- Year Built
- 1850
- Neighborhood
- Roxbury Falls
- 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
Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- Roxbury Falls
- Property / Style
- Single Family · Colonial
- Year Built
- 1850
- Days on Market
- 26 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 6,190 sq ft
- Lot Size
- 41.00 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $19,015 / 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
87
30 active listings
Median $ / Sq Ft
$506
30 active listings
Sale-to-List Ratio
96.1%
29 sales
How this home compares
List Price
$3.60M
vs $1.30M median
2.8× the median
Price / Sq Ft
$582
vs $506 median
15.0% above median
Days on Market
26 days
vs 87 days median
61 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 27, 2026.
Location
268 South Street, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$18,355
- Property Taxes$1,585
- Insurance$1,200
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Roxbury
- Neighborhood
- Roxbury Falls
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1850
- New Construction
- No/Resale
- Living Area
- 6,190 sq ft
Schools
- Elementary
- Booth Free
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 4
- Laundry
- Main LevelUpper Level
- Laundry Location
- 2 Laundry Rooms-Main Floor and 2nd Floor
- Appliances
- Gas CooktopGas RangeOven/RangeCounter GrillRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullUnfinished
- In-Law Apartment
- No
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 41.00 acres
- Zoning
- C
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- Pond
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteIn Ground Pool
- Construction
- Clapboard
- Color
- white
- Roof
- Wood ShingleGable
- Foundation
- BlockStone
- Lot Description
- Fence - WoodFence - PartialSecludedLightly WoodedRollingWater ViewOpen Lot
Listing & Financials
- Property Taxes
- $19,015 / Annually
- Days on Market
- 26
- MLS #
- 24183686
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. 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 7/27/2026 at 6:10 PM UTC.