16 Jonathan Drive, Roxbury, CT 06783
Property image
Property image
FOR SALE
OPEN SAT, 11-1PM
2.29 ACRES

$998,000

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

16 Jonathan Drive, Roxbury, CT 06783

Est. Mortgage $6,910/mo*
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Home Highlights

Single-Family Home
Built in 2003
2.29 acre lot
$492/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 16 Jonathan Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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. Conveniently located near Southbury, Bridgewater, Washington, and Woodbury, Roxbury is a small, close-knit community of approximately 2,260 residents where privacy, natural beauty, and a strong sense of place define the lifestyle. Part of Regional School District 12, Roxbury is home to the highly regarded Booth Free School and offers access to Shepaug Valley School, including the Shepaug Agriscience STEM Academy, providing distinctive educational opportunities from middle school through high school. Roxbury captures the timeless elegance of New England country living, where rolling hills, stone walls, historic architecture, open fields, and wooded landscapes create a setting of exceptional natural beauty. Peaceful and private yet conveniently connected, the town offers an easy balance of rural tranquility and accessibility, with Brewster and Southeast Metro-North stations approximately 30 minutes away for convenient rail access to New York City. Outdoor recreation, hiking, parks, dining, boutique shopping, and cultural destinations are all close at hand. From quiet mornings surrounded by nature to afternoons exploring nearby trails and charming villages, Roxbury offers an understated, sophisticated lifestyle-one that feels wonderfully removed from the pace of the city while remaining approximately 90 minutes from New York City.
Last check for updates: about 5 hours ago
Listing courtesy of Ginny Gordon-O'Neill, (774) 222-5590
William Raveis Real Estate, (774) 222-5590
Source: Smart MLS, MLS#24204225
Also Listed on Smart MLS.

Open House

Saturday, September 19
11:00 AM to 1:00 PM

Home Details for 16 Jonathan Drive

Interior Features

Interior Details
Basement: Full,Interior Entry,ConcreteNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, 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: Gas Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,PropaneHas CoolingAir Conditioning: Ceiling Fan(s),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: 7

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: $998,000Price Per Sqft: $492
Status Change & Dates
Possession Timing: Imediate

Active Status

MLS Status: Active

Location

Direction & Address
City: Roxbury
School Information
Elementary School: Booth FreeJr High / Middle School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Listing Agent
Listing ID: 24204225

Building

Building Area
Building Area: 2028 Square Feet

HOA

No HOA

Lot Information

Lot Area: 2.29 Acres

Miscellaneous

BasementMls Number: 24204225Attic: Storage, Pull Down StairsAttribution Contact: (774) 222-5590Above Grade Unfinished Area: 2028

Around this home

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.
    "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.
    "Peaceful and surrounded by nature. The perfect escape from the city or a great place to live full time."
    0
    Flag
  • Katherine
    "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

Market trends in Roxbury

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
33
1MoM

Home Value

Trulia Estimate
$975K
Since last month
Increased$69K (+7.6%)
Since last year
Increased$234K (+31.5%)
Since last sale
Increased$900K (+1,200.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +88% in the last 10 years
MonthEstimated value
2026
September 2026$975K
August 2026$906K
July 2026$914K
June 2026$918K
May 2026$918K
April 2026$914K
March 2026$962K
February 2026$1.02M
January 2026$729K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
137 Davenport Road, Roxbury, CT
0.10
Single-Family Home
$455,000
08/18/26
3
2
1,614
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
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
249 Woodbury Road, Washington, CT
1.44
Single-Family Home
$529,000
01/09/26
2
2
1,268

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
137 Davenport Road, Roxbury, CT 06783
0.10
$455,000
3
2
1,614
Recently Sold
108 Davenport Road, Roxbury, CT 06783
0.31
$1,951,600
4
5.5
5,100
Off Market
76 Davenport Road, Roxbury, CT 06783
0.39
$1,330,400
2
3
2,445
Off Market
35 Painter Ridge Road, Roxbury, CT 06783
0.38
$1,664,400
2
3
2,799
Off Market
2 Pickett Road, Roxbury, CT 06783
0.40
$1,799,000
5
4.5
3,326
For Sale
00 Pickett Road, Roxbury, CT 06783
0.41
-
-
-
-
Off Market
195 Painter Hill Road, Roxbury, CT 06783
0.57
$933,600
2
2.5
2,322
Off Market
62 Davenport Road, Roxbury, CT 06783
0.62
$5,663,400
4
5
6,228
Off Market
201 Painter Hill Road, Roxbury, CT 06783
0.64
$909,800
3
2
1,720
Off Market
220 Painter Hill Road, Roxbury, CT 06783
0.67
$2,750,000
4
4.5
4,570
For Sale
Painter Hill Road, Roxbury, CT 06783
0.66
-
-
-
-
Off Market

Price and Tax history

DateEventPrice
Sep 9, 2026
Source: Smart MLS #24204225
Listed For Sale
$998,000
Jul 14, 2026
Source: Smart MLS #24153218
ListingRemoved
$950,000
Apr 19, 2026
Source: Smart MLS #24153218
PriceChange
$950,000
Price increased by 13%
Apr 16, 2026
Source: Smart MLS #24153218
PriceChange
$840,000
Price decreased by 16%
Mar 8, 2026
Source: Smart MLS #24153218
PriceChange
$995,000
Price decreased by 5%

LGBTQ Local Legal Protections

Ginny Gordon-O'Neill, William Raveis Real Estate, (774) 222-5590
Agent Phone: (774) 222-5590
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.

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Frequently asked questions about 16 Jonathan Drive

  • What is the estimated monthly payment for 16 Jonathan Drive?
    Based on a $998,000 list price with 20% down at today's rates, the estimated monthly payment for 16 Jonathan Drive in Roxbury, CT is approximately $7,031 (about $5,476 principal & interest, $1,480 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What are the closest schools to 16 Jonathan Drive?
    The closest schools to 16 Jonathan Drive in Roxbury, CT are Booth Free School (Elementary), Shepaug Valley School (Middle/High, rated 8/10).
  • What is 16 Jonathan Drive estimated to be worth?
    Trulia's estimated value for 16 Jonathan Drive in Roxbury, CT is $975,400.
  • Does 16 Jonathan Drive have air conditioning?
    Yes, 16 Jonathan Drive in Roxbury, CT has air conditioning.
  • Does 16 Jonathan Drive have laundry facilities?
    Yes, 16 Jonathan Drive in Roxbury, CT has in-unit laundry.
  • How big is the lot at 16 Jonathan Drive?
    The lot at 16 Jonathan Drive in Roxbury, CT is about 2.3 acres.
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 Sep 9, 2026. The MLS # for this home is MLS# 24204225.