5 Bear Burrow Rd, Roxbury, CT 06783
OFF MARKET

5 Bear Burrow Rd
Roxbury, CT 06783

  • 4 Beds
  • 4 Baths
  • 5,144 sqft (on 8 acres)

$3,845,900

Trulia Estimate
as of May 29, 2026
Est. Refi. Payment $24,965/mo*
Refinance Your Home

$3,845,900

Trulia Estimate
as of May 29, 2026
Est. Refi. Payment $24,965/mo*
Refinance Your Home
4 Beds
4 Baths
5,144 sqft
(on 8 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Tucked away in the pastoral and scenic town of Roxbury in the heart of Litchfield County sits this 5,144 sq. foot newly renovated and magnificent country house. The light and bright kitchen features stone countertops, subway tile walls, stainless appliances, and breakfast room. There is access from the kitchen to the patio which overlooks the panoramic views. The living room complete with fireplace and soaring ceilings is inviting and comfortable, also on the main level is the foyer, formal dining room, study, laundry room and half bath. The dreamy master bedroom is comprised of a luxury bathroom and step down sitting room with two walk-in closets, and yes there is a fireplace in the master too. There are three other bedrooms and two full baths and a children's playroom.The lower level has a full screening room. The property is a dream come true with infinity edge swimming pool, sauna, bluestone patios, boxwood gardens, stone walls and a stocked pond. Just bring your country best. Can be rented for '20-'21 academic year for $175,000 and Summer 2021 for $150,000.
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
Porch, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 5 Bear Burrow Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Laundry Room
Heating & Cooling
Heating: Electric, OilAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: BrickPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1989Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Rental Terms, Policies & Fees

Furnished

Lot Information

Lot Area: 8.00 acres

Additional Information

On Site Laundry Available

Building

Fitness & Sports
Tennis Court

Price History for 5 Bear Burrow Rd

DatePriceEventSource
08/15/2016$2,950,000Sold
N/A
08/12/2014$1,325,000Sold
Smart MLS #98538402
01/19/1999$94,500Sold
N/A
05/17/1994$468,375Sold
Smart MLS #95053669
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Property Tax and Assessment

Year2025
Tax$24,399
Assessment$1,876,840
Home facts updated by county records

Comparable Sales for 5 Bear Burrow Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
143 Tophet Road, Roxbury, CT
0.71
Single-Family Home
$1,925,000
02/17/26
4
5.5
5,848
277 Painter Hill Road, Roxbury, CT
0.63
Single-Family Home
$2,547,500
01/30/26
3
2.5
2,559
253 Tophet Road, Roxbury, CT
0.65
Single-Family Home
$1,500,000
11/18/25
4
3.5
2,437
187 Painter Hill Rd, Roxbury, CT
0.87
Single-Family Home
$1,133,000
08/21/25
4
3.5
3,155
247 Painter Hill Rd, Roxbury, CT
0.77
Single-Family Home
$1,375,000
03/27/26
4
4
2,396
158 Painter Hill Road, Roxbury, CT
0.73
Single-Family Home
$1,195,000
11/07/25
3
2.5
2,793
76 Cross Brook Rd, Roxbury, CT
0.47
Single-Family Home
$850,000
03/11/26
3
2
1,371
39 Painter Hill Road, Woodbury, CT
1.43
Single-Family Home
$1,400,000
07/17/25
4
3
2,418
32 Grassy Hill Road, Roxbury, CT
1.96
Single-Family Home
$1,966,500
12/22/25
4
4
4,728
364 Hoop Pole Hill Road, Woodbury, CT
1.47
Single-Family Home
$975,000
10/01/25
5
3
3,450

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Bear Burrow Rd.
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.
    "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
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Homes for sale near 5 Bear Burrow Rd

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5 Bear Burrow Rd, Roxbury, CT 06783 is a 4 bedroom, 4 bathroom, 5,144 sqft single-family home built in 1989. This property is not currently available for sale. 5 Bear Burrow Rd was last sold on Aug 15, 2016 for $2,950,000. The current Trulia Estimate for 5 Bear Burrow Rd is $3,845,900.