16 Jonathan Drive, Roxbury, CT 06783 - Photo 1

Save This Listing

Close

1/40

View All Photos

$998,000 Just Listed

For Sale
Active
Single Family
3 Beds
2 Full Baths
1 Partial Bath
2,028 Sq. Ft.
2 Car Garage
Updated 12 hours ago

Next open house:

Saturday 9/12 1:00 PM - 3:00 PM

Get directions

Join us at 16 Jonathan Drive on:

Open House: 1:00 PM - 3:00 PM
Sunday 9/13 1:00 PM - 3:00 PM
16 Jonathan Drive,Roxbury, CT 06783
16 Jonathan DriveRoxburyCT06783

See This Home

Save This Listing

Close

1/40

Property Description

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 is on a beautiful lot, at an approx. 1000 ft elevation, has mature landscaped grounds, 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 well-regarded schools. It is also known for its natural beauty, historic character, and strong sense of community.

Full Property Details

Full Property Details for 16 Jonathan Dr

General

Price: $998,000
Taxes: (July 2025-June 2026)
Status: Active
Type: Single Family
Source: SMARTMLS
MLS ID: 24204225
Updated: 9/11/2026
Added to Site: 2 day(s) ago

Interior

Number of Rooms: 7
Interior Features: Auto Garage Door Opener, Cable - Available
Fireplace: Yes
Number of Fireplaces: 2
Appliances: Gas Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 2
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 3
Primary Bedroom: Primary Bedroom - Bedroom Suite, Ceiling Fan, Wall/Wall Carpet, Upper
Bedroom 1: Bedroom - Wall/Wall Carpet, Upper
Bedroom 2: Bedroom - Wall/Wall Carpet, Upper

Other Rooms

Living Room: Living Room - Bay/Bow Window, Hardwood Floor, Main
Dining Room: Dining Room - French Doors, Patio/Terrace, Hardwood Floor, Main
Laundry: Main Level

Exterior

Exterior Features: Shed, Garden Area, French Doors, Patio
Color: Yellow

Parking

Garage: Yes
Attached garage: Yes
Garage Spaces: 2
Parking: Attached Garage

Location

County: Litchfield
Driving Directions: Use GPS

School Information

Elementary School: Booth Free
Intermediate School: Per Board of Ed
High School: Per Board of Ed

Heating & Cooling

Cooling Type: Ceiling Fans, Central Air
Heating Type: Hot Air, Propane
Heating Fuel: Propane
Water Heater: Propane, Domestic

Utilities

Sewer: Septic
Water: Private Well

Structural Information

Architectural Style: Colonial
Construction Status: No/Resale
Exterior Const.: Clapboard
Basement Desc.: Full, Interior Access, Concrete Floor, Full With Hatchway
Roof: Asphalt Shingle
Attic: Yes
Square Feet: 2,028
Above Ground: 2,028 Sq. Ft.
Year Built: 2003

Lot Features

Lot Size (Acres): 2.29
Zoning: C
Lot Description: Secluded, Interior Lot, Lightly Wooded, Dry, On Cul-De-Sac

Financial Considerations

Assessment Amount: $414,890
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 867178

Listed by William Raveis Real Estate, The Cornerstone Team at William Raveis Real Estate, Ginny Gordon-O’Neill

Quickly Find Out More

* Indicates a required field

Comment *

Full Name *

Email Address *

Mobile Phone Number *

See this property in person

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 16 Jonathan Dr —

Ginny Gordon-O’Neill

William Raveis Real Estate

Agent Contact: (774) 222-5590 Office Contact: (203) 794-9494

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender

NMLS#: 1598647

Get Pre-Approved

Schools

Schools serving 16 Jonathan Dr

School District:Regional School District 12

Name	Grades	Distance
Booth Free School 14 South Street, Roxbury, CT 06783	K-5	2.8 mi
Shepaug Valley School 159 South Street, Washington, CT 06793	6-12	0.5 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 16 Jonathan Dr Get Price Alerts and Save Property

Date

Details

Price

Change

Source

9/09/2026

Listed

$998,000

1230.67%

MLS

4/16/2002

Sold

$75,000

—

Public Record

Get Price Alerts and Save Property

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History

Tax History for 16 Jonathan Dr

Year

Property Taxes

Change

Tax Assessment

Change

2025

$5,394

3%

$414,890

—

2023

$5,228

3%

$414,890

24%

2022

$5,086

—

$333,480

—

2021

$5,086

-3%

$333,480

—

2020

$5,269

—

$333,480

—

2019

$5,286

—

$333,480

—

2018

$5,286

4%

$333,480

-7%

2017

$5,082

4%

$357,880

—

2016

$4,903

—

$357,880

—

2015

$4,890

2%

$356,930

—

2014

$4,783

1%

$356,930

—

2012

$4,747

—

$356,930

—

View All

Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost

Estimate the Cost for 16 Jonathan Dr

4 Sunrise Ln, Bridgewater, CT 06752 - Photo 1

Just Listed

$2,395,000

4 Sunrise Ln Bridgewater, CT 06752

Single Family
Active
Updated 1 day ago

4
Beds
6
Total Baths
5,927
Sq. Ft.

Listed by Berkshire Hathaway NE Prop.

90 Sage Rd, Woodbury, CT 06798 - Photo 1

Just Listed

$1,200,000

90 Sage Rd Woodbury, CT 06798

Single Family
Active
Updated 3 days ago

4
Beds
5
Total Baths
3,968
Sq. Ft.

Listed by Klemm Real Estate Inc

229 Bacon Pond Rd, Woodbury, CT 06798 - Photo 1

Just Listed

$209,900

229 Bacon Pond Rd #313 Woodbury, CT 06798

Condo
Active
Updated 1 day ago

2
Beds
1
Total Bath
913
Sq. Ft.

Listed by Drakeley Real Estate, Inc.

123 Old Litchfield Rd, Washington, CT 06794 - Photo 1

Just Listed

$865,000

Open House

123 Old Litchfield Rd Washington, CT 06794

Single Family
Active
Updated 3 days ago

3
Beds
2
Total Baths
2,221
Sq. Ft.

Listed by W. Raveis Lifestyles Realty

18 Hinckley Rd, Washington, CT 06777 - Photo 1

Price Reduced

-$9,900 (-2.02%)

$480,000

18 Hinckley Rd Washington, CT 06777

Single Family
Active
Updated 7 hours ago

3
Beds
2
Total Baths
1,800
Sq. Ft.

Listed by Joseph Chemero (860) 354-4111

Price Reduced

-$10,000 (-4.76%)

$199,900

229 Bacon Pond Rd #312 Woodbury, CT 06798

Condo
Active
Updated 1 day ago

2
Beds
1
Total Bath
913
Sq. Ft.

Listed by Joseph Rohinsky (203) 254-7100

13 Hill View Ln, Woodbury, CT 06798 - Photo 1

13 Hill View Ln Woodbury, CT 06798

Single Family
Active
Updated 2 days ago

2
Beds
3
Total Baths
2,773
Sq. Ft.

Listed by Drakeley Real Estate, Inc.

241 Hoop Pole Hill Rd, Woodbury, CT 06798 - Photo 1

Price Reduced

-$24,000 (-5.47%)

$415,000

241 Hoop Pole Hill Rd Woodbury, CT 06798

Single Family
Active
Updated 3 days ago

3
Beds
3
Total Baths
2,032
Sq. Ft.

Listed by Drakeley Real Estate, Inc.

102 Wykeham Rd, Washington, CT 06793 - Photo 1

Sold

$1,105,000

102 Wykeham Rd Washington, CT 06793

Single Family
Closed

3
Beds
3
Total Baths
2,113
Sq. Ft.

Listed by William Pitt Sotheby's Int'l
Sold by Klemm Real Estate Inc

32 Wykeham Rd, Washington, CT 06793 - Photo 1

Sold

$960,000

32 Wykeham Rd Washington, CT 06793

Single Family
Closed

3
Beds
3
Total Baths
2,046
Sq. Ft.

Listed by Klemm Real Estate Inc
Sold by W. Raveis Lifestyles Realty

45 Chalybes Rd, Roxbury, CT 06783 - Photo 1

Sold

$850,000

45 Chalybes Rd Roxbury, CT 06783

Single Family
Closed

3
Beds
4
Total Baths
2,725
Sq. Ft.

Listed by William Pitt Sotheby's Int'l
Sold by W. Raveis Lifestyles Realty

34 Bacon Rd, Roxbury, CT 06783 - Photo 1

Sold

$959,000

34 Bacon Rd Roxbury, CT 06783

Single Family
Closed

4
Beds
4
Total Baths
3,686
Sq. Ft.

Listed by William Raveis Real Estate
Sold by William Pitt Sotheby's Int'l

16 Jonathan Drive, Roxbury, CT 06783 (MLS# 24204225) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 16 Jonathan Drive is currently listed for $998,000 and was received on September 09, 2026. Want to learn more about 16 Jonathan Drive? Do you have questions about finding other Single Family real estate for sale in Roxbury? You can browse all Roxbury real estate or contact a Coldwell Banker agent to request more information.

16 Jonathan Dr Roxbury, CT 06783

Full Property Details for 16 Jonathan Dr

General

Interior

Rooms

Bathrooms

Bedrooms

Other Rooms

Exterior

Parking

Location

School Information

Heating & Cooling

Utilities

Structural Information

Lot Features

Financial Considerations

Disclosures and Reports

Quickly Find Out More

Quickly Find Out More

Listing agent

Get Pre-Approved Today

Be ready to buy your new home!

Be ready to buy your new home!

Schools serving 16 Jonathan Dr

Price & Sales History for 16 Jonathan Dr Get Price Alerts and Save Property

Tax History for 16 Jonathan Dr

Estimate the Cost for 16 Jonathan Dr

Be ready to buy your new home!

Similar Properties near 16 Jonathan Dr

23 Painter Hill Rd Roxbury, CT 06783

18 Tunnel Rd Roxbury, CT 06783

122 River Rd Washington, CT 06794

180 Weathervane Dr New Milford, CT 06776

Just Listed near 16 Jonathan Dr

4 Sunrise Ln Bridgewater, CT 06752

90 Sage Rd Woodbury, CT 06798

229 Bacon Pond Rd #313 Woodbury, CT 06798

123 Old Litchfield Rd Washington, CT 06794

Price Reduced near 16 Jonathan Dr

18 Hinckley Rd Washington, CT 06777

229 Bacon Pond Rd #312 Woodbury, CT 06798

13 Hill View Ln Woodbury, CT 06798

241 Hoop Pole Hill Rd Woodbury, CT 06798

Recent Sales near 16 Jonathan Dr

102 Wykeham Rd Washington, CT 06793

32 Wykeham Rd Washington, CT 06793

45 Chalybes Rd Roxbury, CT 06783

34 Bacon Rd Roxbury, CT 06783