188 E Flag Swamp Rd, Roxbury, CT 06783
OFF MARKET

$1,005,500

Trulia Estimate
  • 3 Beds
  • 4 Baths
  • 2,684 sqft (on 13.85 acres)

188 E Flag Swamp Rd, Roxbury, CT 06783

Est. Refi. Payment $6,746/mo*
Refinance Your Home
Currently Off Market - Sold Oct 4, 1996 for $295,000

Home Value

Trulia Estimate
$1.01M
Since last month
Increased$12K (+1.2%)
Since last year
Increased$44K (+4.5%)
Since last sale
Increased$713K (+241.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +62% in the last 10 years
MonthEstimated value
2026
August 2026$1.01M
July 2026$996K
June 2026$992K
May 2026$1M
April 2026$972K
March 2026$970K
February 2026$950K
January 2026$939K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
78 Garnet Road, Roxbury, CT
1.14
Single-Family Home
$1,650,000
10/23/25
3
3.5
3,302
500 High Ridge Road, Southbury, CT
0.83
Single-Family Home
$640,000
09/26/25
4
2.5
2,626
53 Transylvania Road, Roxbury, CT
0.91
Single-Family Home
$1,200,000
10/17/25
3
2.5
3,920
67 Transylvania Road, Roxbury, CT
0.97
Single-Family Home
$895,000
01/23/26
4
3
3,624
55 Mallory Road, Roxbury, CT
1.13
Single-Family Home
$615,000
03/17/26
4
3
2,682
39 Hickory Ln, Roxbury, CT
1.20
Single-Family Home
$1,500,000
03/03/26
4
4
3,691
31 Hickory Lane, Roxbury, CT
1.23
Single-Family Home
$1,600,000
07/20/26
4
4
6,169
18 South Street, Woodbury, CT
1.53
Single-Family Home
$629,000
08/21/26
4
2.5
2,880
22 East Woods Road, Roxbury, CT
1.75
Single-Family Home
$610,000
04/17/26
4
2.5
3,476
557 Upper Grassy Hill Road, Woodbury, CT
1.55
Single-Family Home
$885,000
07/30/26
4
3.5
3,784

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
E.flag Swamp Road, Roxbury, CT 06783
0.09
-
-
-
-
Off Market
East Flag Swamp Road, Roxbury, CT 06783
0.09
-
-
-
-
Off Market
208 East Flag Swamp Road, Roxbury, CT 06783
0.27
$915,500
4
3.5
3,974
Off Market
150 East Flag Swamp Road, Roxbury, CT 06783
0.30
$724,500
2
2
1,248
Off Market
130 Flag Swamp Road, Roxbury, CT 06783
0.49
$1,725,300
2
2.5
3,123
Off Market
130 Flag Swamp Road, Roxbury, CT 06783
0.49
$1,747,100
2
2.5
3,123
Off Market
22 Highmeadow Lane, Roxbury, CT 06783
0.55
$1,468,700
4
4
3,481
Off Market
16 High Meadow Lane, Roxbury, CT 06783
0.64
$1,082,600
4
2.5
2,750
Off Market
25 High Meadow Lane, Roxbury, CT 06783
0.65
$1,492,200
4
3
4,310
Off Market
88 Mallory Road, Roxbury, CT 06783
0.72
$972,200
4
2.5
3,004
Off Market
500 High Ridge Road, Southbury, CT 06488
0.83
$665,600
4
2.5
2,626
Off Market
277-279 Southbury Road, Roxbury, CT 06783
0.89
$1,251,300
3
3
3,091
Off Market

Local Information

  • Map ViewExplore the area around 188 E Flag Swamp Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
13.85 acres
Living Area
2,684 sqft
Price/Sqft
$375

About this House

This single-family home is located at 188 E Flag Swamp Rd, Roxbury, CT. 188 E Flag Swamp Rd is in Roxbury, CT and in ZIP code 06783. This property has 3 bedrooms, 4 bathrooms and approximately 2,684 sqft of floor space. This property has a lot size of 13.85 acres and was built in 1994.
188 E Flag Swamp Rd, Roxbury, CT 06783 is a 3 bedroom, 4 bathroom, 2,684 sqft single-family home built in 1994. It last sold for $295,000 on Oct 4, 1996. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,005,500, with a rent estimate of $5,463/month.

Home Details for 188 E Flag Swamp Rd

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1994Year Updated: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 2

Lot Information

Lot Area: 13.85 acres

Price and Tax history

DateEventPrice
Oct 4, 1996
Source: N/A
Sold
$295,000

Market trends in Roxbury

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32

Around this home

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 188 E Flag Swamp Rd

  • What is 188 E Flag Swamp Rd estimated to be worth?
    Trulia's estimated value for 188 E Flag Swamp Rd in Roxbury, CT is $1,005,500.
  • What is the price history for 188 E Flag Swamp Rd?
    188 E Flag Swamp Rd in Roxbury, CT last sold for $295,000 in October 1996.
  • Is Roxbury a buyer's or seller's market?
    Roxbury is currently a balanced market, based on recent for-sale activity.
  • What are the closest schools to 188 E Flag Swamp Rd?
    The closest schools to 188 E Flag Swamp Rd in Roxbury, CT are Booth Free School (Elementary), Shepaug Valley School (Middle/High, rated 8/10).
  • How big is the lot at 188 E Flag Swamp Rd?
    The lot at 188 E Flag Swamp Rd in Roxbury, CT is about 13.9 acres.

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Off Market Homes Near 188 E Flag Swamp Rd

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