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

155 E Flag Swamp Rd
Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 4,342 sqft (on 5.18 acres)

$963,600

Trulia Estimate
as of Jun 11, 2026
Est. Refi. Payment $6,326/mo*
Refinance Your Home

$963,600

Trulia Estimate
as of Jun 11, 2026
Est. Refi. Payment $6,326/mo*
Refinance Your Home
4 Beds
2.5 Baths
4,342 sqft
(on 5.18 acres)

Local Information

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

Description

Our beautiful Litchfield County home sits on 5.18 acres in a private setting bordering state conversation property. This spacious Colonial offers three levels of living and views of mother nature from every window. Our lower level offers a two car garage, spacious mud room, office/gym room and storage area with mechanicals. The Main level of living is stunning with an open staircase and foyer, maple flooring, family room with french doors leading to deck, propane fireplace,beams, crown molding, eat in kitchen with double ovens, five burner stove, granite island, stainless steel, french doors leading to a stone patio, formal dining room, laundry room and half bath. Upper level is complete with plenty of hallway closets, master suite and three other bedrooms, full bath and views of mother nature. The home also features central air, central vac, security system, driveway warning alarm, full house generator with a separate 500 propane tank. Nestled in the country with a 10 minute drive to I- 84 and low low taxes. Masks must be worn and COVID forms signed for viewing.
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, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 155 E Flag Swamp Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Other, Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Stone, WoodPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2005Year Updated: 2013
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 5.18 acres

Price History for 155 E Flag Swamp Rd

DatePriceEventSource
01/07/2021$649,000Sold
N/A
11/15/2020$649,000PendingAgent Provided
11/12/2020$649,000Listed For SaleAgent Provided
11/11/2019$559,000ListingRemovedAgent Provided
07/26/2019$559,000PriceChange
Agent Provided
04/10/2019$579,000PriceChange
Agent Provided
02/26/2019$589,000Listed For SaleAgent Provided
07/10/2015$538,000Sold
Smart MLS #99104430
06/15/2015$549,000PendingAgent Provided
05/13/2015$549,000Listed For SaleAgent Provided
12/30/2013$599,900ListingRemovedAgent Provided
06/19/2013$3,000Listed For RentAgent Provided
06/14/2013$599,900PriceChange
Agent Provided
05/17/2013$649,000PriceChange
Agent Provided
03/25/2013$679,000Listed For SaleAgent Provided
04/25/2012$599,000ListingRemovedAgent Provided
03/02/2012$599,000PriceChange
Agent Provided
07/31/2011$649,000Listed For SaleAgent Provided
06/08/2011$899,000ListingRemovedAgent Provided
05/07/2011$899,000PriceChange
Agent Provided
02/14/2011$695,000PriceChange
Agent Provided
02/12/2011$899,000PriceChange
Agent Provided
02/07/2011$695,000PriceChange
Agent Provided
02/01/2011$899,000PriceChange
Agent Provided
01/30/2011$695,000Listed For SaleAgent Provided
04/28/2006$725,000Sold
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$6,300
Assessment$484,610
Home facts updated by county records

Homeowner tools

Estimated monthly rent$7,826/mo
List your home for rent

Comparable Sales for 155 E Flag Swamp Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
88 Mallory Road, Roxbury, CT
0.50
Single-Family Home
$917,500
08/21/25
4
2.5
3,004
55 Mallory Road, Roxbury, CT
0.87
Single-Family Home
$615,000
03/17/26
4
3
2,682
22 Highmeadow Lane, Roxbury, CT
0.80
Single-Family Home
$1,378,000
07/08/25
4
4
3,481
500 High Ridge Road, Southbury, CT
1.00
Single-Family Home
$640,000
09/26/25
4
2.5
2,626
53 Transylvania Road, Roxbury, CT
1.16
Single-Family Home
$1,200,000
10/17/25
3
2.5
3,920
67 Transylvania Road, Roxbury, CT
1.22
Single-Family Home
$895,000
01/23/26
4
3
3,624
78 Garnet Road, Roxbury, CT
0.89
Single-Family Home
$1,650,000
10/23/25
3
3.5
3,302
184 Brown Brook Rd, Southbury, CT
1.31
Single-Family Home
$575,000
06/23/25
3
3
2,114
18 Mallory Road, Roxbury, CT
1.15
Single-Family Home
$2,575,000
08/29/25
3
3.5
3,384
39 Hickory Ln, Roxbury, CT
1.37
Single-Family Home
$1,500,000
03/03/26
4
4
3,691

Nearby homes

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Assigned Schools

These are the assigned schools for 155 E Flag Swamp 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
    Flag

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Apartments for Rent

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Homes for sale near 155 E Flag Swamp Rd

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Off Market Homes Near 155 E Flag Swamp Rd

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155 E Flag Swamp Rd, Roxbury, CT 06783 is a 4 bedroom, 3 bathroom, 4,342 sqft single-family home built in 2005. This property is not currently available for sale. 155 E Flag Swamp Rd was last sold on Jan 7, 2021 for $649,000. The current Trulia Estimate for 155 E Flag Swamp Rd is $963,600.