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

$915,500

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

208 East Flag Swamp Road, Roxbury, CT 06783

Est. Refi. Payment $6,149/mo*
Refinance Your Home
Currently Off Market - Sold Feb 19, 2025 for $840,000

Home Value

Trulia Estimate
$916K
Since last month
Increased$4K (+0.5%)
Since last year
Increased$56K (+6.5%)
Since last sale
Increased$76K (+9%)
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 +28% in the last 10 years
MonthEstimated value
2026
August 2026$916K
August 2026$915K
July 2026$911K
June 2026$895K
May 2026$890K
April 2026$887K
March 2026$897K
February 2026$889K
January 2026$878K
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
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
31 Hickory Lane, Roxbury, CT
1.32
Single-Family Home
$1,600,000
07/20/26
4
4
6,169
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
557 Upper Grassy Hill Road, Woodbury, CT
1.40
Single-Family Home
$885,000
07/30/26
4
3.5
3,784
55 Mallory Road, Roxbury, CT
1.35
Single-Family Home
$615,000
03/17/26
4
3
2,682
18 South Street, Woodbury, CT
1.36
Single-Family Home
$629,000
08/21/26
4
2.5
2,880

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
0.27
-
-
-
-
Off Market
East Flag Swamp Road, Roxbury, CT 06783
0.27
-
-
-
-
Off Market
22 Highmeadow Lane, Roxbury, CT 06783
0.49
$1,468,700
4
4
3,481
Off Market
150 East Flag Swamp Road, Roxbury, CT 06783
0.56
$724,500
2
2
1,248
Off Market
500 High Ridge Road, Southbury, CT 06488
0.56
$665,600
4
2.5
2,626
Off Market
25 High Meadow Lane, Roxbury, CT 06783
0.55
$1,492,200
4
3
4,310
Off Market
16 High Meadow Lane, Roxbury, CT 06783
0.60
$1,082,600
4
2.5
2,750
Off Market
130 Flag Swamp Road, Roxbury, CT 06783
0.75
$1,725,300
2
2.5
3,123
Off Market
130 Flag Swamp Road, Roxbury, CT 06783
0.75
$1,747,100
2
2.5
3,123
Off Market
53 Transylvania Road, Roxbury, CT 06783
0.79
$1,261,600
3
2.5
3,920
Off Market
380 Southbury Road, Roxbury, CT 06783
0.79
$1,495,000
4
4.5
4,452
For Sale

Local Information

  • Map ViewExplore the area around 208 East Flag Swamp Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
10 acre lot
3,974 sqft
$230/sqft
2 Car Garage

About this House

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
208 East Flag Swamp Road, Roxbury, CT 06783 is a 4 bedroom, 4 bathroom, 3,974 sqft single-family home built in 1986. It last sold for $840,000 on Feb 19, 2025 (1% below the $850,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $915,500, with a rent estimate of $6,741/month.
Last check for updates: about 2 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

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)

Price and Tax history

DateEventPrice
Feb 19, 2025
Source: Smart MLS #24032283
Sold
$840,000
Sep 30, 2024
Source: Smart MLS #24032283
PriceChange
$850,000
Price decreased by 2%
Aug 23, 2024
Source: Smart MLS #24032283
PriceChange
$870,000
Price decreased by 3%
Jul 13, 2024
Source: Smart MLS #24032283
Listed For Sale
$895,000

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

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.

Frequently asked questions about 208 East Flag Swamp Road

  • What is 208 East Flag Swamp Road estimated to be worth?
    Trulia's estimated value for 208 East Flag Swamp Road in Roxbury, CT is $915,500.
  • What is the price history for 208 East Flag Swamp Road?
    208 East Flag Swamp Road in Roxbury, CT last sold for $840,000 in February 2025.
  • 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 208 East Flag Swamp Road?
    The closest schools to 208 East Flag Swamp Road in Roxbury, CT are Booth Free School (Elementary), Shepaug Valley School (Middle/High, rated 8/10).
  • Does 208 East Flag Swamp Road have air conditioning?
    Yes, 208 East Flag Swamp Road in Roxbury, CT has air conditioning.
  • Does 208 East Flag Swamp Road have laundry facilities?
    Yes, 208 East Flag Swamp Road in Roxbury, CT has in-unit laundry.

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