Does Roxbury, CT show holiday spirit?

As of early 2026, 100% of users say there's holiday spirit

Is a car needed in Roxbury, CT?

As of early 2026, 100% of users say car is needed

Is Roxbury, CT quiet?

As of early 2026, 100% of users say it's quiet

Are yards well-kept in Roxbury, CT?

As of early 2026, 80% of users say yards are well-kept

Is Roxbury, CT dog-friendly?

As of early 2026, 80% of users say it's dog friendly

Is parking easy in Roxbury, CT?

As of early 2026, 80% of users say parking is easy

Is there wildlife in Roxbury, CT?

As of early 2026, 67% of users say there's wildlife

Would people walk alone at night in Roxbury, CT?

As of early 2026, 50% of users say people would walk alone at night

Do residents of Roxbury, CT plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Are neighbors friendly in Roxbury, CT?

As of early 2026, 29% of users say neighbors are friendly

Is Roxbury, CT walkable to grocery stores?

As of early 2026, 25% of users say it's walkable to grocery stores

FOR SALE

2.29 ACRES

16 Jonathan Drive
Roxbury, CT 06783

3 Beds
2.5 Baths
2,028 sqft (on 2.29 acres)

$950,000

$840,000

Est. Mortgage $6,288/mo*

Get Pre-Qualified

$950,000

$840,000

Est. Mortgage $6,288/mo*

Get Pre-Qualified

3 Beds

2.5 Baths

2,028 sqft

(on 2.29 acres)

Local Information

Map ViewExplore the area around 16 Jonathan Drive.
Schools1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This is a wonderful well cared for country home in the beautiful small town of Roxbury. Situated on this dead end road you are minutes to local amenities. Take advantage of nearby hiking trails, parks and open space with Southbury, Bridgewater, Washington and Woodbury town centers just a short drive away. Only 90 minutes from NYC. The first floor has two fireplaces and is open and spacious with French doors from two locations out onto private patios. There are three bedrooms on the second floor with lots of light and charm. Owned by the same owners since construction you can see the care. The first floor has beautiful hardwood floors, a well thought out country kitchen with double ovens plus gorgeous counters and cabinets. with a nearby den and a large living room-dining room with fireplace. Come and enjoy the view of the spacious hills beyond. Schools are part of Region 12 which includes Washington. The owner is a wonderful gardener and her grounds are so enjoyable!

Home Highlights

Parking

2 Car Garage

Outdoor

Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$468

Listed

155 days ago

Home Details for 16 Jonathan Drive

Interior Features
Interior Details Basement: FullNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 2028 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Oven/Range, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls Door: French Doors

Exterior Features
Exterior Home Features Roof: AsphaltPatio / Porch: PatioOther Structures: Shed(s)Exterior: GardenFoundation: Concrete PerimeterGardenNo Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Garage Door Opener
Frontage Not on Waterfront
Water & Sewer Sewer: Septic Tank
Finished Area Finished Area (above surface): 2028 Square Feet

Days on Market
Days on Market: 155

Property Information
Year Built Year Built: 2003
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information Parcel Number: 867178

Price & Status
Price List Price: $950,000Price Per Sqft: $468
Status Change & Dates Possession Timing: Negio

Active Status
MLS Status: Active

Location
Direction & Address City: Roxbury
School Information Elementary School: Per Board of EdHigh School: Per Board of Ed

Agent Information
Listing Agent Listing ID: 24153218

Building
Building Area Building Area: 2028 Square Feet

Community
Community Features: Lake, Library, Playground, Private School(s), Shopping/Mall
Other Playground

HOA
No HOA

Lot Information
Lot Area: 2.29 Acres

Miscellaneous
BasementMls Number: 24153218Attic: Access Via HatchAttribution Contact: (203) 449-3568Above Grade Unfinished Area: 2028

Additional Information
LakeLibraryPlaygroundPrivate School(s)Shopping/Mall

Last check for updates: about 3 hours ago

Listing courtesy of Joyce Drakeley, (203) 449-3568

Drakeley Real Estate, Inc., (203) 449-3568

Source: Smart MLS, MLS#24153218

Market trends in Roxbury

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Price History for 16 Jonathan Drive

Date	Price	Event	Source
04/19/2026	$950,000	PriceChange	Smart MLS #24153218
Price Change $110,000 (13%)
04/16/2026	$840,000	PriceChange	Smart MLS #24153218
Price Change $155,000 (-16%)
03/08/2026	$995,000	PriceChange	Smart MLS #24153218
Price Change $55,000 (-5%)
02/09/2026	$1,050,000	Listed For Sale	Smart MLS #24153218

04/16/2002	$75,000	Sold	N/A
Recording Date 04/16/2002 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$5,394
Assessment	$414,890

Home facts updated by county records

Comparable Sales for 16 Jonathan Drive

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
277 Painter Hill Road, Roxbury, CT	0.98	Single-Family Home	$2,547,500	01/30/26	3	2.5	2,559
158 Painter Hill Road, Roxbury, CT	1.04	Single-Family Home	$1,195,000	11/07/25	3	2.5	2,793
322 North Street, Roxbury, CT	1.02	Single-Family Home	$500,000	09/05/25	3	2	1,397
16 Orchard Lane, Washington, CT	1.29	Single-Family Home	$1,725,000	10/28/25	3	2	2,564
315 North Street, Roxbury, CT	1.12	Single-Family Home	$1,400,000	06/09/26	4	3	2,420

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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 16 Jonathan Drive.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Roxbury

At least 2 Trulia users voted on each feature.

100 % Say there's holiday spirit
100 % Say car is needed
100 % Say it's quiet
80 % Say yards are well-kept
80 % Say it's dog friendly
80 % Say parking is easy
67 % Say there's wildlife
50 % Say people would walk alone at night
50 % Say they plan to stay for at least 5 years
29 % Say neighbors are friendly
25 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Lisa r. h.
Resident
7y ago
"This is an incredibly supportive town, with many young families. Lots of townwide events to meet new people, and friendly neighbors. We moved in 9 years ago and love living here!"
2
Flag
Maria T.
12y ago
"Peaceful and surrounded by nature. The perfect escape from the city or a great place to live full time."
0
Flag
Katherine
15y ago
"This is one of the most gorgeous towns in Connecticut. Quintessential New England, with lots of privacy - yes there are celebs - but who cares! They are just people too. You get the best of everything - lovely town green, no traffic, a short drive to everything you need, acreage with your house and low taxes. People are friendly, helpful, nice to you and no smog!!!!!!!!! Yes, we love it here. "
0
Flag

LGBTQ Local Legal Protections

Joyce Drakeley, Drakeley Real Estate, Inc., (203) 449-3568

Agent Phone: (203) 449-3568

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

16 Jonathan Drive, Roxbury, CT 06783 is a 3 bedroom, 3 bathroom, 2,028 sqft single-family home built in 2003. This property is currently available for sale and was listed by Smart MLS on Feb 9, 2026. The MLS # for this home is MLS# 24153218.

16 Jonathan Drive Roxbury, CT 06783

$950,000

$950,000

Local Information

Description

Home Highlights

Home Details for 16 Jonathan Drive

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

Building

Community

HOA

Lot Information

Miscellaneous

Additional Information

Market trends in Roxbury

Price History for 16 Jonathan Drive

Similar Homes You May Like

New Listings near 16 Jonathan Drive

Property Tax and Assessment

Comparable Sales for 16 Jonathan Drive

Nearby homes

Additional Cost

Assigned Schools

What Locals Say about Roxbury

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

16 Jonathan Drive
Roxbury, CT 06783