16 Jonathan Drive
Roxbury, Connecticut 06783
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,028
- Acres
- 2.29
- Year Built
- 2003
- 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
Tucked away on a highly sought-after country road, this charming Colonial has been lovingly maintained by its original owners and offers privacy, lovely grounds, and exceptionally low taxes. Distinctive character begins with its graceful rounded-front porch and continues throughout this exceptionally well-built home, where timeless craftsmanship meets enduring charm. A welcoming foyer features a distinctive staircase to the upper level and opens to the living and dining rooms on the left, while a cozy den flows into the bright eat-in kitchen on the right. The laundry and half bath are conveniently located just off the kitchen. Beautiful hardwood floors, two fireplaces, and French doors leading to private patios create inviting spaces for everyday living and entertaining. Upstairs, the spacious primary suite offers walk-in closets and a well-appointed bath with Jacuzzi and large separate shower. Two additional bedrooms feature generous closets, complemented by a large linen closet. This well loved home has beautifully landscaped grounds, mature plantings, private patios and a cute garden shed creating a peaceful country retreat. There is an approx 1,100 sq ft basement with tall ceilings offering a great expansion opportunity, or excellent for storage. Roxbury is a quintessential New England community with very low taxes and home to the well-regarded Booth Free School. It is also known for its natural beauty, historic character, and strong sense of community.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2003
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,028 sq ft
- Lot Size
- 2.29 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $5,394 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
25
7 under contract
Median List Price
$1.29M
25 active listings
Median Closed Price
$1.20M
27 sales
Median Days on Market
110
25 active listings
Median $ / Sq Ft
$492
25 active listings
Sale-to-List Ratio
95.0%
27 sales
How this home compares
List Price
$998,000
vs $1.29M median
22.9% below median
Price / Sq Ft
$492
vs $492 median
In line with median
Days on Market
0 days
vs 110 days median
110 days fresher than median
Based on 25 active and 27 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of September 10, 2026.
Location
16 Jonathan Drive, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 3, 2026per month
- Principal & Interest$5,157
- Property Taxes$450
- Insurance$333
- 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
- Colonial
- Year Built
- 2003
- New Construction
- No/Resale
- Living Area
- 2,028 sq ft
Schools
- Elementary
- Booth Free
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- laundry room off kitchen
- Appliances
- Gas CooktopWall OvenMicrowaveRefrigeratorDishwasherWasherElectric Dryer
- Basement
- FullInterior AccessConcrete FloorFull With Hatchway
- Interior Features
- Auto Garage Door OpenerCable - Available
Exterior & Lot
- Lot Size
- 2.29 acres
- Zoning
- C
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Clapboard
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedGarden AreaFrench DoorsPatio
- Lot Description
- SecludedInterior LotLightly WoodedDryOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $5,394 / Annually
- Days on Market
- 0
- MLS #
- 24204225
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/10/2026. 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 9/10/2026 at 5:05 AM UTC.