208 East Flag Swamp Road, Roxbury, CT 06783
OFF MARKET

208 East Flag Swamp Road
Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,974 sqft (on 10 acres)

$894,200

Trulia Estimate
as of Jun 8, 2026
Est. Refi. Payment $5,876/mo*
Refinance Your Home

$894,200

Trulia Estimate
as of Jun 8, 2026
Est. Refi. Payment $5,876/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,974 sqft
(on 10 acres)

Local Information

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

Description

Seclusion in Rural Roxbury. Tucked back on dirt road, 10 acres surrounded by nature, trees, birds, and wildlife..... Custom home has a mix of palladium windows, skylights, vaulted ceilings, interior balconies, three fireplaces, eclectic chandeliers and open spaces all add a Contemporary Flair to this colonial home. Primary suite with sitting area and fireplace. First floor ensuite bedroom, French doors exit to back decking - au pair? live in help? multigenerational living? CHECK, CHECK AND CHECK! Be sure to look at the attached floor plan to see the extra study, second floor reading space and very flexible floor plan. Have fun updating it and making it your own peaceful respite. Subject to lot line revision - in the process, application submitted. Taxes will be adjusted accordingly upon approval. Fresh paint in and out, new oil tank, all hardwood just refinished on both floors. Roof replaced 2011 /12 per executor
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. This description is from February 21, 2025

Home Highlights

Parking
2 Car Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 208 East Flag Swamp Road

Interior Features

Interior Details
Basement: FullNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Study, Sun Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3974 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Paved,Driveway,Garage Door Opener,Private
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3974 Square Feet

Property Information

Year Built
Year Built: 1986
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Contemporary
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 866282

Price & Status

Price
List Price: $850,000
Status Change & Dates
Off Market Date: Mon Feb 03 2025Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: RoxburyCommunity: Flag Swamp
School Information
Elementary School: Booth FreeHigh School: Shepaug

Building

Building Area
Building Area: 3974 Square Feet

Community

Community Features: Golf, Health Club, Lake, Library, Medical Facilities, Park, Private School(s), Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 10 Acres

Miscellaneous

BasementMls Number: 24032283Attic: Pull Down StairsAbove Grade Unfinished Area: 3974

Additional Information

GolfHealth ClubLakeLibraryMedical FacilitiesParkPrivate School(s)Tennis Court(s)
Last check for updates: about 9 hours ago
Listed by Mary Ann Bennett, (203) 206-7048
Drakeley Real Estate, Inc., (203) 263-4336
Bought with: Svetlana Mastrogiannis, (203) 482-4284, William Raveis Real Estate, (203) 794-9494
Source: Smart MLS, MLS#24032283

Price History for 208 East Flag Swamp Road

DatePriceEventSource
02/19/2025$840,000Sold
Smart MLS #24032283
09/30/2024$850,000PriceChange
Smart MLS #24032283
08/23/2024$870,000PriceChange
Smart MLS #24032283
07/13/2024$895,000Listed For SaleSmart MLS #24032283

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$7,703
Assessment$592,550
Home facts updated by county records

Comparable Sales for 208 East Flag Swamp Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22 Highmeadow Lane, Roxbury, CT
0.49
Single-Family Home
$1,378,000
07/08/25
4
4
3,481
88 Mallory Road, Roxbury, CT
0.98
Single-Family Home
$917,500
08/21/25
4
2.5
3,004
500 High Ridge Road, Southbury, CT
0.56
Single-Family Home
$640,000
09/26/25
4
2.5
2,626
67 Transylvania Road, Roxbury, CT
0.88
Single-Family Home
$895,000
01/23/26
4
3
3,624
53 Transylvania Road, Roxbury, CT
0.79
Single-Family Home
$1,200,000
10/17/25
3
2.5
3,920
1823 South Britain Road, Southbury, CT
1.30
Single-Family Home
$799,000
10/17/25
4
3.5
3,892
78 Garnet Road, Roxbury, CT
1.30
Single-Family Home
$1,650,000
10/23/25
3
3.5
3,302
55 Mallory Road, Roxbury, CT
1.35
Single-Family Home
$615,000
03/17/26
4
3
2,682
35 Bronson Mountain Road, Roxbury, CT
0.88
Single-Family Home
$2,501,000
11/21/25
5
5
8,091

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Assigned Schools

These are the assigned schools for 208 East Flag Swamp Road.
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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Homes for sale near 208 East Flag Swamp Road

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Off Market Homes Near 208 East Flag Swamp Road

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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208 East Flag Swamp Road, Roxbury, CT 06783 is a 4 bedroom, 4 bathroom, 3,974 sqft single-family home built in 1986. This property is not currently available for sale. 208 East Flag Swamp Road was last sold on Feb 19, 2025 for $840,000 (1% lower than the asking price of $850,000). The current Trulia Estimate for 208 East Flag Swamp Road is $894,200.