Off market dec 2025 for $2.7M

$3,084,677

Est. refi paymentEst. refi $9,428/mo

•

5,455

sq ft

16 Sentry Hill Rd, Roxbury, CT 06783

About this home

Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious media room. The main floor primary suite includes a fireplace, office space, and large walk in closet. There is an addl guest room on the main level, perfect for nursery or in-laws.3 bedrooms/2 baths on the second level. Lower level game room has full bath and can be used as a 6th bedroom. Gunite heated pool with stone terraces incorporates room for relaxing and dining pool side. 3 car garage has unfinished space above which could be finished to an apartment or studio. Multi zone stereo system. Just 5 minutes to Washington with chic shops, farmer's market and

Single-familyProperty Type

1989Year Built

16.71 acresLot Size

$565Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Stacey Matthews • W. Raveis Lifestyles Realty

Contact: Agent Attribution Contact: (203) 671-9067 | Office Attribution Contact: (860) 868-0511

Bought with Stacey Matthews • W. Raveis Lifestyles Realty

Source:Smart MLS #24093019

Redfin Estimate

$3,084,677

$385K since sold in December 2025$37K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 101% higher than the average sale price ($1.53M) of 6 comparable homes.

SOLD AUG 19, 2026
$3,340,000
A
5 beds5 baths5,940 sq ft
8 Bayberry Hl, Roxbury, CT 06783
SOLD SEP 24, 2026
$2,058,000
B
4 beds3 baths5,296 sq ft
8 Sunrise Ln, Bridgewater, CT 06752
SOLD OCT 16, 2026
$580,000
C
4 beds2.5 baths2,990 sq ft
8 Pebble Ln, New Milford, CT 06776
SOLD OCT 8, 2026
$1,795,000
D
4 beds3.5 baths3,198 sq ft
18 Ranney Hill Rd, Roxbury, CT 06783
SOLD OCT 22, 2026
$695,000
E
4 beds3.5 baths2,347 sq ft
20 Timber Ln, New Milford, CT 06776
SOLD JUL 29, 2026
$740,200
F
4 beds3 baths4,065 sq ft
45 Beardsley Rd, New Milford, CT 06776

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Earn from this home

Sell

$777,532

Est. take-home

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Refinance

Est. cash available

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Rent

$4,454/mo

Redfin rental estimate

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Market trends in 06783, CT

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

96.0%

+2.8% MoM

Median sale price

$960K

$440K MoM

Avg. days on market

126d

0 days MoM

Recently sold homes

6 MoM

New listings for sale

$1,075,000
4 beds2.5 baths4,265 sq ft
5 North St, Roxbury, CT 06783
$2,450,000
4 beds2.5 baths3,000 sq ft
179 South St, Roxbury, CT 06783
See all

Provided by Redfin

Sale history for 16 Sentry Hill Rd

Date

Event

Price

Smart MLS #24093019

Dec 16, 2025

Sold

$2,700,000

$495/sq ft

Sep 19, 2025

Pending

—

Sep 10, 2025

Contingent

—

Aug 15, 2025

Price Changed

$2,995,000

$549/sq ft

May 8, 2025

Price Changed

$3,250,000

$596/sq ft

May 8, 2025

Listed

$2,600,000

$477/sq ft

Public Records

Feb 20, 2001

Sold

$1,437,500

$264/sq ft

Smart MLS #98073542

May 26, 2000

Listed

$1,650,000

$302/sq ft

Smart MLS #96001606

Jan 26, 1996

Listing Removed

—

Jan 10, 1996

Listed

$714,500

$131/sq ft

Smart MLS #95031311

Jan 9, 1996

Listing Removed

—

Oct 21, 1995

Listed

$724,500

$133/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$26,835 (−2.8%)

$305,060 + $1,824,690

$2,129,750

2022

$27,598 (−1.0%)

$313,880 + $1,495,820

$1,809,700

2021

$27,869 (−2.5%)

$313,880 + $1,495,810

$1,809,690

2020

$28,593 (−0.3%)

$313,880 + $1,495,810

$1,809,690

2019

$28,684

$313,880 + $1,495,810

$1,809,690

2018

$28,684 (+11.0%)

$313,880 + $1,495,810

$1,809,690

2017

$25,849 (+3.6%)

$382,060 + $1,438,270

$1,820,330

2016

$24,939 (+2.2%)

$382,060 + $1,438,270

$1,820,330

2014

$24,392

$382,060 + $1,438,270

$1,820,330

Tax history for 16 Sentry Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$26,835 (−2.8%)

$305,060 + $1,824,690

$2,129,750

2022

$27,598 (−1.0%)

$313,880 + $1,495,820

$1,809,700

2021

$27,869 (−2.5%)

$313,880 + $1,495,810

$1,809,690

2020

$28,593 (−0.3%)

$313,880 + $1,495,810

$1,809,690

2019

$28,684

$313,880 + $1,495,810

$1,809,690

2018

$28,684 (+11.0%)

$313,880 + $1,495,810

$1,809,690

2017

$25,849 (+3.6%)

$382,060 + $1,438,270

$1,820,330

2016

$24,939 (+2.2%)

$382,060 + $1,438,270

$1,820,330

2014

$24,392

$382,060 + $1,438,270

$1,820,330

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

16.71 Acres

Year renovated

2016

Sq. Ft.

5,455

Year built

1989

Style

Single Family Residential

County

Litchfield County

APN

866377

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Driveway
Garages Number: 3

Parking Information
Parking Total Spaces: 10

Interior

Interior Information
Total Rooms: 10
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Security System
In-Law Apartment: Possible
In-Law Access: Lower Level, Over Garage
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Gas Cooktop, Wall Oven, Range Hood, Subzero, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Basement Description: Partial, Partially Finished
Has Attic
Attic Description: Storage Space

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Stone, Stucco
Exterior Features: Breezeway, Awnings, Fruit Trees, Stone Wall, French Doors, Underground Sprinkler

Lot Information
Lot Description: Secluded, Lightly Wooded, Rocky, Level Lot, Professionally Landscaped

Pool Information
Swimming Pool
Pool Description: Gunite, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: stucco and stone

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 5455
Driveway Type: Circular, Paved, Crushed Stone

Financial

Assessments Information
Assessed Value: $2,129,750

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Other
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: Above Ground
Energy Features: Generator

Location

School Information
Middle Jr High School: Shepaug
High School: Shepaug
Elementary School: Booth Free

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Health Club, Library, Park, Playground/Tot Lot, Private School(s), Stables/Riding, Tennis Courts
Directions: Rt 199 to Sentry Hill Rd. # 16 on right.
County: Litchfield

Public facts

Beds: 4
Baths: 4.5
Sq. Ft.: 5,455
Stories: 2.0
Lot Size: 16.71 acres
Style: Single Family Residential
Year Built: 1989
Year Renovated: 2016
County: Litchfield County
APN: 866377

Home facts updated by county records on Jun 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 4

Around this home

Schools

K - 12
Preschool & daycare

Booth Free School

Public K-5 • Assigned • 2.0mi

Shepaug Valley School

Public 6-12 • Assigned • 1.8mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

4/10 Wind Factor

19% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Roxbury, CT • 06783

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 4.2 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.93M – $3.55M

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Home values near 16 Sentry Hill Rd

Data from public records.

Address	Redfin Estimate
52 Sentry Hill Rd, Roxbury, CT 4 Beds \| 5.5 Baths \| 4720 Sq. Ft.	$1,864,535
42 Sentry Hill Rd, Roxbury, CT 3 Beds \| 3.5 Baths \| 4673 Sq. Ft.	$1,373,382
24 Sentry Hill Rd, Roxbury, CT 3 Beds \| 2.5 Baths \| 1955 Sq. Ft.	$832,362
155 North St, Roxbury, CT 3 Beds \| 2.5 Baths \| 3036 Sq. Ft.	$1,276,046
92 Judds Bridge Rd, Roxbury, CT 4 Beds \| 5 Baths \| 3900 Sq. Ft.	$2,082,995
48 Judds Bridge Rd, Roxbury, CT 3 Beds \| 2 Baths \| 1816 Sq. Ft.	$889,055
157 North St, Roxbury, CT 3 Beds \| 3.5 Baths \| 3114 Sq. Ft.	$1,489,511

Address	Redfin Estimate
62 Sentry Hill Rd, Roxbury, CT 4 Beds \| 2.5 Baths \| 3500 Sq. Ft.	$2,584,338
30 Sentry Hill Rd, Roxbury, CT 3 Beds \| 3 Baths \| 2404 Sq. Ft.	$750,944
33 Sentry Hill Rd, Roxbury, CT 4 Beds \| 3.5 Baths \| 3676 Sq. Ft.	$1,271,349
99 Judds Bridge Rd, Roxbury, CT 3 Beds \| 5 Baths \| 4223 Sq. Ft.	$2,587,075
51 Judds Bridge Rd, Roxbury, CT 4 Beds \| 3 Baths \| 3708 Sq. Ft.	$889,649
63 Judds Bridge Rd, Roxbury, CT 4 Beds \| 2.5 Baths \| 4831 Sq. Ft.	$1,716,552
198 North St, Roxbury, CT 1 Beds \| 1 Baths \| 1320 Sq. Ft.	$337,862

Address	Redfin Estimate
10 Sentry Hill Rd, Roxbury, CT 4 Beds \| 3 Baths \| 2520 Sq. Ft.	$673,542
29 Sentry Hill Rd, Roxbury, CT 3 Beds \| 2.5 Baths \| 2966 Sq. Ft.	$1,176,503
197 North St, Roxbury, CT 5 Beds \| 2.5 Baths \| 2377 Sq. Ft.	$613,319
58 Judds Bridge Rd, Roxbury, CT 4 Beds \| 3.5 Baths \| 3108 Sq. Ft.	$1,171,141
94 Judds Bridge Rd, Roxbury, CT 2 Beds \| 1.5 Baths \| 1990 Sq. Ft.	$720,215
77 Judds Bridge Rd, Roxbury, CT 4 Beds \| 2.5 Baths \| 2901 Sq. Ft.	$1,229,009
222 North St, Roxbury, CT 2 Beds \| 1 Baths \| 900 Sq. Ft.	$512,788

Property information provided by Smart MLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06783, CT

Sale history for 16 Sentry Hill Rd

Tax history for 16 Sentry Hill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06783

Home values near 16 Sentry Hill Rd

More real estate resources