Last Sold Price
4 beds3,974 sqft$211/sqft
208 E Flag Swamp Rd, Roxbury, CT 06783

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!...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
LISTING CLOSED: 02/19/2025 12:00 AM

  1. Listed by Mary Ann Bennett • Drakeley Real Estate, Inc.
    P: (203) 206-7048 C: (203) 206-7048 maryann@drakeley.com

Property Details for 208 East Flag Swamp Road

Status
MLS #
24032283
Days on Market
196
Taxes
$7,010 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
MLS Type
Residential
Year Built
1986
Lot Size
10.00 AC / 435,600 SF
Basement Description
Full
Direct Waterfront
No
Garages Number
2
Neighborhood
Flag Swamp
Style
Colonial, Contemporary
Garage Parking Info
Attached Garage, Paved, Driveway
Swimming Pool
No

Recent comparable sales

Median sold price

$959,000

Avg days on market

77

Sale-to-list ratio

94.5%

[Roxbury, CT]

9 comparable properties found

$895,000 | 67 Transylvania Road, Roxbury, CT 06783
1

$895,000

Sold 01/23/26

4
Bedrooms
3,624
Square Feet
3.13
Acres
$959,000 | 34 Bacon Road, Roxbury, CT 06783
2

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Sold 03/30/26

4
Bedrooms
3,686
Square Feet
3.77
Acres
$1,378,000 | 22 Highmeadow Lane, Roxbury, CT 06783
3

$1,378,000

Sold 07/08/25

4
Bedrooms
3,481
Square Feet
5.98
Acres
$940,000 | 80 Transylvania Road, Roxbury, CT 06783
4

$940,000

Sold 05/07/25

4
Bedrooms
3,088
Square Feet
4
Acres
$917,500 | 88 Mallory Road, Roxbury, CT 06783
5

$917,500

Sold 08/21/25

4
Bedrooms
3,004
Square Feet
13.49
Acres
$615,000 | 55 Mallory Road, Roxbury, CT 06783
6

$615,000

Sold 03/17/26

4
Bedrooms
2,682
Square Feet
3.23
Acres
$1,764,000 | 176 Apple Lane, Roxbury, CT 06783
7

$1,764,000

Sold 07/20/26

4
Bedrooms
3,566
Square Feet
4.24
Acres
$2,575,000 | 18 Mallory Road, Roxbury, CT 06783
8

$2,575,000

Sold 08/29/25

3
Bedrooms
3,384
Square Feet
4
Acres
$1,650,000 | 78 Garnet Road, Roxbury, CT 06783
9

$1,650,000

Sold 10/23/25

3
Bedrooms
3,302
Square Feet
15.29
Acres

Location

Listing Courtesy of Drakeley Real Estate, Inc., Mary Ann Bennett

Sold By William Raveis Real Estate, Svetlana Mastrogiannis

Add your commute

Building Information for 208 East Flag Swamp Road

Stories-Year Built1986Building Size-Lot Size10.00 AC / 435,600 SF

Payment Calculator

$4,854 per month

30 year fixed, 6.55% Interest

Principal and Interest

$4,270

Property Taxes

$584

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 208 East Flag Swamp Road

Summary
Property and Location
  • Acres Source: Owner
  • Directions: East Flagg Swamp Road
  • Elementary School: Booth Free
  • High School: Shepaug
  • Latitude: 41.51415
  • Longitude: -73.273674
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Park, Private School(s), Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 6
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $7,010
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Intercom, Open Floor Plan
  • Laundry Room Info: Main Level
  • Laundry Room Location: kit pantry, sink, cabinets, iron board
  • Rooms Additional: Foyer, Solarium
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 2
  • Room Features: Built-In Hutch,Interior Balcony,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 4
  • Room Entry Order: 3
  • Room Features: Breakfast Nook,Country,Wet Bar,Island,Pantry,Tile Floor
  • Room Level: Main
  • Room Type: Kitchen
Room 5
  • Listing Key: 1D1292F6EFD65B03E063D501100A3214
  • Room Entry Order: 4
  • Room Features: Ceiling Fan,French Doors,Patio/Terrace,Tile Floor
  • Room Level: Main
  • Room Type: Sun Room
Room 6
  • Room Entry Order: 5
  • Room Features: Balcony/Deck,Built-Ins,French Doors,Hardwood Floor
  • Room Level: Main
  • Room Type: Study
Room 7
  • Room Entry Order: 6
  • Room Features: Vaulted Ceiling,Ceiling Fan,Wet Bar,Fireplace,Hardwood Floor
  • Room Level: Upper
  • Room Type: Family Room
Room 8
  • Room Entry Order: 7
  • Room Features: Bedroom Suite,Fireplace,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 9
  • Listing Key: 1D1292F6EFD65B03E063D501100A3214
  • Room Entry Order: 8
  • Room Features: Bedroom Suite,French Doors,Full Bath,Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 10
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: beige
  • Construction Description: Frame
  • Driveway Type: Private, Paved
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1986
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 3974
Lot Information
  • Lot Description: Secluded, Lightly Wooded, Cleared
  • Parcel Number: 866282
  • Sq Ft Est Heated Above Grade: 3974.0
  • Sq Ft Total: 3974.0
  • Zoning: C
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 208 East Flag Swamp Road

DateEvent & SourcePriceAppreciation
Feb 18, 2025

Closed (Public Record)

Public Record #1551762957

$404,272
Feb 12, 2025

Closed (Public Record)

Public Record #1551762956

$435,728
DateEvent & SourcePrice
02/18/2025

Closed (Public Record)

Public Record #1551762957

$404,272
02/12/2025

Closed (Public Record)

Public Record #1551762956

$435,728

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 208 East Flag Swamp Road

Taxable ValueLand$162,540Additions$430,010Total$592,550
Tax Record2025$7,703 ($642 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt3,974 SqFtAbove Grade Finished SqFt3,974 SqFtUnfinished Basement SqFt2,215 SqFtStories2Lot Size438,214 SqFtStyleSingle Family ResidenceYear Built1986Year Renovated2006ZoningCCountyNORTHWEST HILLSAPNRXBY M:32 L:1

Schools near 208 East Flag Swamp Road

This home is within Regional School District 12.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 12
Public - K to 5
Public - PK to 5
Rating
School
Distance
Booth Free School
PublicK to 5

Shepaug Valley School
Public6 to 12

The Burnham School
PublicK to 5

Washington Primary School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 208 East Flag Swamp Road, Roxbury, CT 06783
$840,000
4
3,974
435,600
3
2
2,099
133,294
4
3
2,300
87,120
3
2
1,362
304,920
$485,000
4
2,168
175,982
$1
2
1
574
118,047

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Drakeley Real Estate, Inc., Mary Ann Bennett

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.