Off market jul 2020 for $288K

$643,320

Est. refi paymentEst. refi $2,325/mo

•

2,016

sq ft

158 E Flag Swamp Rd, Roxbury, CT 06783

About this home

Terrific value!!Privately situated hilltop home with 4.75 woodland acres. Located on a quiet country road on the Roxbury/Southbury line. Take a tour of this 4BR home 2.5 BTH colonial built in 2000. Offering an eat in kitchen with ss appliances, tile flooring and stone/tile back splash. Spacious dining and living rooms (LR has a pellet stove). The family room is just off the kitchen with sliders out to deck and rear patio. The MBR (with full bath and walk-in closet), three guest rooms and hall bath complete the upper level. The partially finished LL features a large bonus/recreation room, and storage/mechanical room. A functional floor plan with plenty of space seen in this tri-level home. Entertain on the rear patio, deck or side yard (great for cook-outs and family/friend gatherings). Additional features include hardwood flooring (main and upper levels), mini-split duct less AC (main level), ceiling fans (all BRs), vinyl siding, shed and new roof. A peaceful getaway! Only 10 minutes to exit 14, I-84, shopping, movie theater, restaurants, Audubon Center, Shepaug River, state parks/preserves and much more. Bring your imagination and don't miss out!

Single-familyProperty Type

2000Year Built

4.75 acresLot Size

$319Est. Price/Sq.Ft.

Listed by Liz Newnham • William Pitt Sotheby's Int'l

Bought with Brandy Granata • Coldwell Banker Realty

Source:Smart MLS #170292861

Redfin Estimate

$643,320

$355K since sold in July 2020$5,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.4% higher than the average sale price ($641K) of 6 comparable homes.

SOLD SEP 28, 2026
$606,000
A
3 beds2.5 baths2,282 sq ft
90 Mallory Rd, Roxbury, CT 06783
SOLD AUG 21, 2026
$629,000
B
4 beds2.5 baths2,880 sq ft
18 South St, Woodbury, CT 06798
SOLD JUN 26, 2026
$770,000
C
4 beds2.5 baths1,990 sq ft
78 Old Poverty Rd, Southbury, CT 06488
SOLD SEP 11, 2026
$500,000
D
3 beds2.5 baths2,232 sq ft
155 Deer Hill Rd, Southbury, CT 06488
SOLD SEP 29, 2026
$705,000
E
4 beds2.5 baths2,367 sq ft
121 Carriage Dr, Southbury, CT 06488
BOUGHT WITH REDFIN SEP 11, 2026
$635,000
F
4 beds2.5 baths2,878 sq ft
297 N Poverty Rd, Southbury, CT 06488

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Earn from this home

Sell

$402,309

Est. take-home

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Refinance

Est. cash available

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Rent

$3,058/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 158 E Flag Swamp Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,227 (+11.7%)

$119,700 + $215,740

$335,440

2022

$3,784 (−1.0%)

$123,200 + $124,920

$248,120

2021

$3,821 (−2.5%)

$123,200 + $124,920

$248,120

2020

$3,920 (−0.3%)

$123,200 + $124,920

$248,120

2019

$3,933

$123,200 + $124,920

$248,120

2018

$3,933 (−3.1%)

$123,200 + $124,920

$248,120

2017

$4,059 (+3.6%)

$144,370 + $141,510

$285,880

2016

$3,917 (+2.2%)

$144,370 + $141,510

$285,880

2014

$3,831

$144,370 + $141,510

$285,880

Tax history for 158 E Flag Swamp Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,227 (+11.7%)

$119,700 + $215,740

$335,440

2022

$3,784 (−1.0%)

$123,200 + $124,920

$248,120

2021

$3,821 (−2.5%)

$123,200 + $124,920

$248,120

2020

$3,920 (−0.3%)

$123,200 + $124,920

$248,120

2019

$3,933

$123,200 + $124,920

$248,120

2018

$3,933 (−3.1%)

$123,200 + $124,920

$248,120

2017

$4,059 (+3.6%)

$144,370 + $141,510

$285,880

2016

$3,917 (+2.2%)

$144,370 + $141,510

$285,880

2014

$3,831

$144,370 + $141,510

$285,880

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

4.75 Acres

Year renovated

2011

Sq. Ft.

2,016

Year built

2000

Style

Single Family Residential

County

Litchfield County

APN

866426

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Off Street Parking

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 8
Laundry Room Info: Main Level
Cooling System: Ceiling Fans, Ductless
Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Room Count: 9
Basement Description: Full, Partially Finished
Has Attic
Attic Description: Access Via Hatch

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Patio

Lot Information
Lot Description: Sloping Lot

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: Tan

Property Information
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2016
Driveway Type: Paved, Gravel

Financial

Assessments Information
Assessed Value: $248,120

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil
Heat Type: Baseboard
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

Location

School Information
High School: Regional District 12
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Health Club, Lake, Medical Facilities, Park, Playground/Tot Lot, Private School(s)
Directions: Route 172 to Flag Swamp Rd..turns into E. Flag Swamp Rd. OR South St Or Mallory to Flag Swamp Rd.
County: Litchfield

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,016
Stories: 2.0
Lot Size: 4.75 acres
Style: Single Family Residential
Year Built: 2000
Year Renovated: 2011
County: Litchfield County
APN: 866426

Home facts updated by county records on Jun 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 3

Around this home

Schools

K - 12
Preschool & daycare

Booth Free School

Public K-5 • Assigned • 3.0mi

Shepaug Valley School

Public 6-12 • Assigned • 6.0mi

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

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

5/10 Wind Factor

23% 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

$612,000 – $740,000

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Home values near 158 E Flag Swamp Rd

Data from public records.

Address	Redfin Estimate
135 Flag Swamp Road, Roxbury, CT 3 Beds \| 2 Baths \| 1888 Sq. Ft.	$783,791
137 Flag Swamp Road, Roxbury, CT 4 Beds \| 3.5 Baths \| 3207 Sq. Ft.	$1,266,586
192 E Flag Swamp Road, Roxbury, CT 4 Beds \| 3.5 Baths \| 3744 Sq. Ft.	$1,422,297
199 E Flag Swamp Road, Roxbury, CT 3 Beds \| 2 Baths \| 2984 Sq. Ft.	$952,505
130 Flag Swamp Road, Roxbury, CT 2 Beds \| 2.5 Baths \| 3123 Sq. Ft.	$1,533,610
103 Mallory Road, Roxbury, CT 3 Beds \| 3.5 Baths \| 2328 Sq. Ft.	$858,287

Address	Redfin Estimate
11 W Flag Swamp Road, Roxbury, CT 3 Beds \| 1.5 Baths \| 1850 Sq. Ft.	$611,507
155 E Flag Swamp Road, Roxbury, CT 4 Beds \| 2.5 Baths \| 2890 Sq. Ft.	$1,023,920
181 E Flag Swamp Road, Roxbury, CT 3 Beds \| 2.5 Baths \| 3600 Sq. Ft.	$1,105,468
130 E Flag Swamp Road, Roxbury, CT 2 Beds \| 2.5 Baths \| 3123 Sq. Ft.	$1,626,835
115 Mallory Road, Roxbury, CT 3 Beds \| 2 Baths \| 2883 Sq. Ft.	$592,886
111 Mallory Road, Roxbury, CT 3 Beds \| 2.5 Baths \| 2367 Sq. Ft.	$741,133

Address	Redfin Estimate
188 E Flag Swamp Road, Roxbury, CT 3 Beds \| 3.5 Baths \| 2684 Sq. Ft.	$874,962
201 E Flag Swamp Road, Roxbury, CT 3 Beds \| 2 Baths \| 1362 Sq. Ft.	$562,871
150 E Flag Swamp Road, Roxbury, CT 2 Beds \| 2 Baths \| 1248 Sq. Ft.	$686,286
142 E Flag Swamp Road, Roxbury, CT 4 Beds \| 3.5 Baths \| 4544 Sq. Ft.	$3,444,365
108 Mallory Road, Roxbury, CT 4 Beds \| 2.5 Baths \| 2349 Sq. Ft.	$768,207
121 Mallory Road, Roxbury, CT 4 Beds \| 2.5 Baths \| 2885 Sq. Ft.	$909,881

Property information provided by Smart MLS when last listed in 2020. 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 158 E Flag Swamp Rd

Tax history for 158 E Flag Swamp 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 158 E Flag Swamp Rd

More real estate resources