42 Sentry Hill Rd, Roxbury, CT 06783
OFF MARKET

42 Sentry Hill Rd
Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 4,673 sqft (on 3.54 acres)

$1,463,500

Trulia Estimate
as of Jun 9, 2026
Est. Refi. Payment $9,569/mo*
Refinance Your Home

$1,463,500

Trulia Estimate
as of Jun 9, 2026
Est. Refi. Payment $9,569/mo*
Refinance Your Home
3 Beds
3.5 Baths
4,673 sqft
(on 3.54 acres)

Local Information

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

Description

Relax with pure privacy in this classic turnkey farmhouse, beautifully sited on 3.5 acres in the heart of bucolic Roxbury, Ct. Soaked in natural light, the warm and refined 3-bed/3.1-bath main residence is tastefully appointed throughout with timber flooring, crown moldings, and roomy interiors that include a formal living room, formal dining room, and a main floor family room ... each with its own fireplace, oversized windows, French doors to spacious bluestone entertaining patio, and sunny views. The bright country kitchen boasts an eating island with prep sink, marble countertops, Christopher Peacock cabinetry, Viking stove, warmer, double dishwasher, and pantry area with wet bar. Three generous sized bedrooms are all en suite and include a main floor guest suite with dual vanities and glass shower, and a peaceful second level master suite with wood burning fireplace and 5-piece bathroom with dual marble vanities, glass shower, large jetted tub overlooking the garden, and a generous walk-in closet.Make the most of Roxbury summers in your beautiful heated Gunite pool--the focal point of the 3.5-acre lot with professionally landscaped grounds, perennial gardens and room for outdoor activities of your choice. This special home has been meticulously cared for and generously loved. See to believe! Other highlights include laundry room and office with potential for use as 4th bedroom, 3-car detached garage, 1,100 sqft basement, and an abundance of storage options.Total serenity in the heart of Roxbury CT. Near town, tennis courts, golf and organic farm stands--and only 90 minutes from NYC. This is a property for the person who is ready to move in today.
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
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 42 Sentry Hill Rd

Interior Features

Interior Details
BasementNumber of Rooms: 4Types of Rooms: Laundry Room
Heating & Cooling
Heating: Forced Air, OtherAir ConditioningCooling System: OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherGardenPatio
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached

Property Information

Year Built
Year Built: 1957Year Updated: 2013
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 2

Lot Information

Lot Area: 3.54 acres

Price History for 42 Sentry Hill Rd

DatePriceEventSource
06/06/2019$680,000Sold
Smart MLS #170104579
04/15/2019$799,000PendingAgent Provided
04/15/2019$799,000Listed For SaleAgent Provided
01/23/2019$799,000ListingRemovedAgent Provided
09/07/2018$799,000PriceChange
Agent Provided
07/11/2018$899,000PriceChange
Agent Provided
03/14/2018$925,000Listed For SaleAgent Provided
05/06/2015$1,025,000ListingRemovedAgent Provided
03/17/2015$1,025,000Listed For SaleAgent Provided
12/17/2014$1,025,000ListingRemovedAgent Provided
06/26/2014$1,025,000PriceChange
Agent Provided
07/16/2013$1,075,000PriceChange
Agent Provided
04/06/2013$1,150,000Listed For SaleAgent Provided
12/12/2012$1,150,000ListingRemovedAgent Provided
10/21/2012$1,150,000PriceChange
Agent Provided
04/07/2011$1,250,000Listed For SaleAgent Provided
12/16/2010$1,250,000ListingRemovedAgent Provided
05/15/2010$1,250,000PriceChange
Agent Provided
10/16/2009$1,200,000PriceChange
Agent Provided
08/02/2009$1,250,000PriceChange
Agent Provided
05/31/2009$1,350,000Listed For SaleAgent Provided
09/28/2007$1,200,000Sold
N/A
02/04/2003$440,000Sold
N/A

Market trends in Roxbury

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
23
2MoM
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Property Tax and Assessment

Year2025
Tax$9,257
Assessment$712,110
Home facts updated by county records

Comparable Sales for 42 Sentry Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Spargo Road, Roxbury, CT
0.53
Single-Family Home
$1,050,000
10/15/25
3
2.5
1,571
235 North Street, Roxbury, CT
0.70
Single-Family Home
$1,325,000
06/18/25
4
3.5
3,379
16 Sentry Hill Road, Roxbury, CT
0.23
Single-Family Home
$2,700,000
12/16/25
5
5.5
5,455
88 Hemlock Road, Roxbury, CT
0.95
Single-Family Home
$1,400,000
08/22/25
2
2.5
3,389
27 Wakelee Road, Roxbury, CT
0.86
Single-Family Home
$1,837,500
09/16/25
4
2.5
2,640
11 Hodge Road, Roxbury, CT
1.23
Single-Family Home
$912,500
11/19/25
4
3
2,982
51 Battle Swamp Rd, Roxbury, CT
0.85
Single-Family Home
$2,900,000
08/13/25
4
9
4,805
71 Beardsley Road, New Milford, CT
1.20
Single-Family Home
$650,000
01/22/26
4
2.5
2,514
118 Chalybes Road West, Roxbury, CT
1.29
Single-Family Home
$754,500
02/11/26
6
5
4,260
23 Sun Pond Lane, New Milford, CT
1.46
Single-Family Home
$760,000
05/15/26
4
2.5
3,082

Nearby homes

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Assigned Schools

These are the assigned schools for 42 Sentry Hill 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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42 Sentry Hill Rd, Roxbury, CT 06783 is a 3 bedroom, 4 bathroom, 4,673 sqft single-family home built in 1957. This property is not currently available for sale. 42 Sentry Hill Rd was last sold on Jun 6, 2019 for $680,000. The current Trulia Estimate for 42 Sentry Hill Rd is $1,463,500.