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

OFF MARKET

32 Jonathan Dr
Roxbury, CT 06783

3 Beds
2 Baths
2,504 sqft (on 3.09 acres)

$832,200

Trulia Estimate

as of May 25, 2026

Est. Refi. Payment $5,508/mo*

Refinance Your Home

$832,200

Trulia Estimate

as of May 25, 2026

Est. Refi. Payment $5,508/mo*

Refinance Your Home

3 Beds

2 Baths

2,504 sqft

(on 3.09 acres)

Local Information

-- mins to

Commute Destination

Description

AVAILABLE ANNUALLY APRIL 1, 2022 @ $6,500 PER MONTH. Charming and stylish 3 bedroom ranch at the end of a quiet road with lots of privacy. Lovely gardens and lots of light. Separate media room Jonathan drive is great for riding bikes with kids and is near to many land trust trails. 10 minutes to Washington (shops, farmers market) and Woodbury (organic market, restaurants).
1.5 hours to NYC.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 32 Jonathan Dr

Interior Features
Interior Details BasementNumber of Rooms: 7
Heating & Cooling Heating: Heat Pump, OilAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1
Appliances & Utilities DishwasherDryerRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Wood
Parking & Garage GarageParking Space: 1Parking: Garage Attached

Property Information
Year Built Year Built: 1977Year Updated: 2009
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information
Lot Area: 3.09 acres

Price History for 32 Jonathan Dr

Date	Price	Event	Source
03/08/2022		ListingRemoved	William Raveis Real Estate, Mortgage & Insurance

01/29/2022	$6,500	PriceChange	William Raveis Real Estate, Mortgage & Insurance #170463890
Price Change $4,500 (-41%)
01/21/2022	$11,000	Listed For Rent	William Raveis Real Estate, Mortgage & Insurance #170462657

09/16/2021		ListingRemoved	William Raveis Real Estate, Mortgage & Insurance

09/15/2021	$7,000	PriceChange	William Raveis Real Estate, Mortgage & Insurance #170433504
Price Change $1,500 (27%)
08/17/2021	$5,500	PriceChange	William Raveis Real Estate, Mortgage & Insurance #170408624
Price Change $400 (-7%)
07/16/2021	$5,900	PriceChange	William Raveis Real Estate, Mortgage & Insurance #170408624
Price Change $1,100 (-16%)
06/09/2021	$7,000	Listed For Rent	William Raveis Real Estate, Mortgage & Insurance #170408624

03/13/2021		ListingRemoved	William Raveis Real Estate, Mortgage & Insurance

11/04/2020	$10,000	PriceChange	Agent Provided
Price Change $19,000 (-66%)
10/06/2020	$29,000	Listed For Rent	Agent Provided

08/20/2020	$6,200	ListingRemoved	Agent Provided

08/14/2020	$6,200	Listed For Rent	Agent Provided

06/02/2016	$495,000	Sold	N/A
Recording Date 06/02/2016 County Transfer Tax N/A Total Transfer Tax $45
02/28/2008	$450,000	Sold	Smart MLS #G460766
Recording Date 02/28/2008 County Transfer Tax N/A Total Transfer Tax N/A
10/09/1990	$190,000	Sold	N/A
Recording Date 10/09/1990 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$5,088
Assessment	$391,370

Home facts updated by county records

Comparable Sales for 32 Jonathan Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
7 Jonathan Dr, Roxbury, CT	0.24	Single-Family Home	$1,050,000	12/09/25	3	3	1,976
247 Painter Hill Rd, Roxbury, CT	0.56	Single-Family Home	$1,375,000	03/27/26	4	4	2,396
277 Painter Hill Road, Roxbury, CT	0.84	Single-Family Home	$2,547,500	01/30/26	3	2.5	2,559
187 Painter Hill Rd, Roxbury, CT	0.70	Single-Family Home	$1,133,000	08/21/25	4	3.5	3,155
158 Painter Hill Road, Roxbury, CT	1.00	Single-Family Home	$1,195,000	11/07/25	3	2.5	2,793
322 North Street, Roxbury, CT	1.17	Single-Family Home	$500,000	09/05/25	3	2	1,397
16 Orchard Lane, Washington, CT	1.24	Single-Family Home	$1,725,000	10/28/25	3	2	2,564
76 Cross Brook Rd, Roxbury, CT	1.32	Single-Family Home	$850,000	03/11/26	3	2	1,371
249 Woodbury Road, Washington, CT	1.44	Single-Family Home	$529,000	01/09/26	2	2	1,268
235 North Street, Roxbury, CT	1.41	Single-Family Home	$1,325,000	06/18/25	4	3.5	3,379

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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FOR SALE
NEW - 2 DAYS AGO
NEW CONSTRUCTION
8.35 ACRES
$1,799,000
5 bd
4.5 ba
3,326 sqft
2 Pickett Road,
Roxbury, CT 06783
William Pitt Sotheby's Int'l
FOR SALE
2.27 ACRES
$475,000
3 bd
2 ba
1,614 sqft
137 Davenport Road,
Roxbury, CT 06783
The Provino Group LLC
FOR SALE
3.21 ACRES
$1,195,000
3 bd
2 ba
2,031 sqft
246 North Street,
Roxbury, CT 06783
William Pitt Sotheby's Int'l
FOR SALE
3 ACRES
$250,000
307 North Street,
Roxbury, CT 06783
Klemm Real Estate Inc
FOR SALE
4.68 ACRES
$2,895,000
4 bd
4.5 ba
4,570 sqft
220 Painter Hill Road,
Roxbury, CT 06783
W. Raveis Lifestyles Realty
SOLD
MAY 1, 2026
$2,195,000
4 bd
4.5 ba
3,699 sqft
63 West Mountain Road,
Washington, CT 06793
W. Raveis Lifestyles Realty
FOR SALE
2.29 ACRES
$950,000
3 bd
2.5 ba
2,028 sqft
16 Jonathan Drive,
Roxbury, CT 06783
Drakeley Real Estate, Inc.
FOR SALE
26.68 ACRES
$775,000
204 North Street Lot 3,
Roxbury, CT 06783
Brown Harris Stevens
FOR SALE
18.62 ACRES
$1,995,000
4 bd
4.5 ba
4,874 sqft
1030 Washington Woodbury Road,
Roxbury, CT 06783
Klemm Real Estate Inc
SOLD
JAN 30, 2026
$2,547,500
3 bd
2.5 ba
2,559 sqft
277 Painter Hill Road,
Roxbury, CT 06783
W. Raveis Lifestyles Realty
SOLD
JAN 9, 2026
$529,000
2 bd
2 ba
1,268 sqft
249 Woodbury Road,
Washington, CT 06793
Klemm Real Estate Inc
FOR SALE
24.84 ACRES
$490,000
69 Moosehorn Road,
Roxbury, CT 06783
W. Raveis Lifestyles Realty

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Additional Cost

Assigned Schools

These are the assigned schools for 32 Jonathan Dr.

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.
11y 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

Apartments for Rent

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Explore by feature

FURNISHED
$16,500/mo
Fees may apply
4 bd
2.5 ba
3,089 sqft
5 North St,
Roxbury, CT 06783
3.02 ACRES
$15,000/mo
Fees may apply
3 bd
3.5 ba
2,862 sqft
24 Old Roxbury Rd,
Roxbury, CT 06783
14.09 ACRES
$15,000/mo
Fees may apply
4 bd
5 ba
3,996 sqft
34 Old Roxbury Rd,
Roxbury, CT 06783
6.17 ACRES
$2,500/mo
Fees may apply
1 bd
1 ba
875 sqft
160A North St,
Roxbury, CT 06783
FURNISHED
$30,900/mo
Fees may apply
3 bd
3.5 ba
4,251 sqft
45 Moosehorn Rd,
Roxbury, CT 06783

Homes for sale near 32 Jonathan Dr

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2.27 ACRES
$475,000
3 bd
2 ba
1,614 sqft
137 Davenport Road,
Roxbury, CT 06783
The Provino Group LLC
2.29 ACRES
$950,000
3 bd
2.5 ba
2,028 sqft
16 Jonathan Drive,
Roxbury, CT 06783
Drakeley Real Estate, Inc.
4.68 ACRES
$2,895,000
4 bd
4.5 ba
4,570 sqft
220 Painter Hill Road,
Roxbury, CT 06783
W. Raveis Lifestyles Realty
4.96 ACRES
$795,000
3 bd
2.5 ba
2,336 sqft
38 West Mountain Lane,
Roxbury, CT 06783
Klemm Real Estate Inc
NEW - 2 DAYS AGO
NEW CONSTRUCTION
8.35 ACRES
$1,799,000
5 bd
4.5 ba
3,326 sqft
2 Pickett Road,
Roxbury, CT 06783
William Pitt Sotheby's Int'l
3.21 ACRES
$1,195,000
3 bd
2 ba
2,031 sqft
246 North Street,
Roxbury, CT 06783
William Pitt Sotheby's Int'l
3.01 ACRES
$1,649,000
4 bd
3.5 ba
2,716 sqft
33 Sentry Hill Road,
Roxbury, CT 06783
Klemm Real Estate Inc
4.59 ACRES
$995,000
2 bd
3.5 ba
3,285 sqft
49 South Street,
Washington, CT 06793
William Pitt Sotheby's Int'l
18.62 ACRES
$1,995,000
4 bd
4.5 ba
4,874 sqft
1030 Washington Woodbury Road,
Roxbury, CT 06783
Klemm Real Estate Inc
3 ACRES
$1,095,000
4 bd
2.5 ba
1,782 sqft
23 Painter Hill Road,
Roxbury, CT 06783
Klemm Real Estate Inc
See more homes for sale in
Roxbury
Take a look

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Off Market Homes Near 32 Jonathan Dr

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SOLD
MAY 20, 2026
$825,000
4 bd
2.5 ba
3,043 sqft
120 Old Hayrake Lane,
New Milford, CT 06776
William Raveis Real Estate
SOLD
MAY 15, 2026
$760,000
4 bd
2.5 ba
3,082 sqft
23 Sun Pond Lane,
New Milford, CT 06776
Coldwell Banker Realty
SOLD
MAY 8, 2026
$475,000
4 bd
2 ba
1,914 sqft
112 Weekeepeemee Road,
Bethlehem, CT 06751
Berkshire Hathaway NE Prop.
SOLD
MAY 1, 2026
$825,000
3 bd
2.5 ba
3,074 sqft
189 Crane Hollow Road,
Bethlehem, CT 06751
Coldwell Banker Realty
SOLD
APR 30, 2026
$425,000
4 bd
3.5 ba
2,842 sqft
63 Old Ridge Road,
New Milford, CT 06776
Coldwell Banker Realty
SOLD
APR 29, 2026
$594,000
3 bd
2.5 ba
2,754 sqft
15 Mulberry Lane,
New Milford, CT 06776
Pro Property Management, LLC
SOLD
APR 17, 2026
$610,000
4 bd
2.5 ba
3,476 sqft
22 East Woods Road,
Roxbury, CT 06783
Coldwell Banker Realty
SOLD
APR 10, 2026
$480,000
3 bd
2 ba
1,088 sqft
13 South Street,
Washington, CT 06793
RE/MAX RISE
SOLD
APR 7, 2026
$922,000
3 bd
3.5 ba
2,279 sqft
109 Church Hill Road,
Washington Depot, CT 06794
Klemm Real Estate Inc
SOLD
MAR 30, 2026
$959,000
4 bd
4 ba
3,686 sqft
34 Bacon Road,
Roxbury, CT 06783
William Raveis Real Estate
See more homes for sale in
Roxbury
Take a look

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Homes for rent near 32 Jonathan Dr

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3.71 ACRES
$6,000/mo
Fees may apply
3 bd
3 ba
2,312 sqft
95 Shinar Mountain Rd,
Washington Depot, CT 06794
FURNISHED
$8,500/mo
Fees may apply
4 bd
3.5 ba
2,538 sqft
115 River Rd,
Washington Depot, CT 06794
2.23 ACRES
$29,500/mo
Fees may apply
4 bd
2.5 ba
2,360 sqft
126 River Rd,
Washington Depot, CT 06794
FURNISHED
$10,000/mo
Fees may apply
4 bd
2.5 ba
3,296 sqft
108 East St,
Washington, CT 06793
FURNISHED
$6,000/mo
Fees may apply
4 bd
3 ba
1,260 sqft
10 Sentry Hill Rd,
Roxbury, CT 06783
FURNISHED
$16,500/mo
Fees may apply
4 bd
2.5 ba
3,089 sqft
5 North St,
Roxbury, CT 06783
14.09 ACRES
$15,000/mo
Fees may apply
4 bd
5 ba
3,996 sqft
34 Old Roxbury Rd,
Roxbury, CT 06783
6.17 ACRES
$2,500/mo
Fees may apply
1 bd
1 ba
875 sqft
160A North St,
Roxbury, CT 06783
FURNISHED
$15,900/mo
Fees may apply
2 bd
2 ba
2,153 sqft
17 Kirby Rd,
Washington, CT 06793
FURNISHED
$30,900/mo
Fees may apply
3 bd
3.5 ba
4,251 sqft
45 Moosehorn Rd,
Roxbury, CT 06783
See more homes for rent in
Roxbury
Take a look

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32 Jonathan Dr, Roxbury, CT 06783 is a 3 bedroom, 2 bathroom, 2,504 sqft single-family home built in 1977. This property is not currently available for sale. 32 Jonathan Dr was last sold on Jun 2, 2016 for $495,000. The current Trulia Estimate for 32 Jonathan Dr is $832,200.

32 Jonathan Dr
Roxbury, CT 06783

$832,200

$832,200

Local Information