Skip to main content

16 Jonathan Drive

Roxbury, Connecticut 06783

ACTIVE - NEW$998,000
Beds
3
Baths
2 | 1
SqFt
2,028
Acres
2.29
Year Built
2003
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
2-Car Garage2 Fireplaces

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

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

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,940

per 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.

Listed By

Ginny Gordon-O’Neill

(774) 222-5590

William Raveis Real Estate

(203) 794-9494

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.