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

158 E Flag Swamp Rd
Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 2,016 sqft (on 4.75 acres)

$621,300

Trulia Estimate
as of Mar 21, 2026
Est. Refi. Payment $4,139/mo*
Refinance Your Home

$621,300

Trulia Estimate
as of Mar 21, 2026
Est. Refi. Payment $4,139/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,016 sqft
(on 4.75 acres)

Homes for sale near 158 E Flag Swamp Rd

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Apartments for Rent

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Local Information

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

Description

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!
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
No Info
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 158 E Flag Swamp Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Baseboard, OtherAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherPatio
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 2000Year Updated: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 4.75 acres

Price History for 158 E Flag Swamp Rd

DatePriceEventSource
07/22/2020$288,000Sold
Smart MLS #170292861
06/06/2020$289,900PendingAgent Provided
05/29/2020$289,900PriceChange
Agent Provided
05/06/2020$295,000Listed For SaleAgent Provided
04/01/2020$294,900ListingRemovedAgent Provided
11/09/2019$294,900PriceChange
Agent Provided
05/30/2019$299,900PriceChange
Agent Provided
08/11/2018$309,000Listed For SaleAgent Provided
07/13/1999$55,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$4,361
Assessment$335,440
Home facts updated by county records

Comparable Sales for 158 E Flag Swamp Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
88 Mallory Road, Roxbury, CT
0.48
Single-Family Home
$917,500
08/21/25
4
2.5
3,004
55 Mallory Road, Roxbury, CT
0.90
Single-Family Home
$615,000
03/17/26
4
3
2,682
22 Highmeadow Lane, Roxbury, CT
0.75
Single-Family Home
$1,378,000
07/08/25
4
4
3,481
130 Flag Swamp Road, Roxbury, CT
0.31
Single-Family Home
$1,600,000
04/11/25
2
2.5
3,123
500 High Ridge Road, Southbury, CT
1.05
Single-Family Home
$640,000
09/26/25
4
2.5
2,626
396 Southbury Road, Roxbury, CT
1.21
Single-Family Home
$645,000
04/25/25
3
2
2,382
130 Flag Swamp Rd, Roxbury, CT
0.34
Single-Family Home
$1,600,000
04/11/25
2
2.5
3,123
80 Transylvania Road, Roxbury, CT
1.22
Single-Family Home
$940,000
05/07/25
4
2.5
3,088
402 High Ridge Rd, Southbury, CT
1.18
Single-Family Home
$656,000
05/16/25
4
2.5
3,008
184 Brown Brook Rd, Southbury, CT
1.41
Single-Family Home
$575,000
06/23/25
3
3
2,114

Assigned Schools

These are the assigned schools for 158 E Flag Swamp Rd.
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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 it's quiet

  • 100 % Say car is needed

  • 80 % Say yards are well-kept

  • 80 % Say it's dog friendly

  • 75 % Say parking is easy

  • 67 % Say there's wildlife

  • 50 % Say people would walk alone at night

  • 33 % Say they plan to stay for at least 5 years

  • 29 % Say neighbors are friendly

  • 25 % Say it's walkable to grocery stores

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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Homes for rent near 158 E Flag Swamp Rd

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Off Market Homes Near 158 E Flag Swamp Rd

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Explore by feature

158 E Flag Swamp Rd, Roxbury, CT 06783 is a 4 bedroom, 3 bathroom, 2,016 sqft single-family home built in 2000. This property is not currently available for sale. 158 E Flag Swamp Rd was last sold on Jul 22, 2020 for $288,000. The current Trulia Estimate for 158 E Flag Swamp Rd is $621,300.