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5 Roosevelt Drive

Seymour, Connecticut 06483

ACTIVE - NEW$579,000
Beds
2
Baths
2
SqFt
2,108
Acres
0.13
Year Built
1948
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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WaterfrontDock / Mooring

About This Home

Direct Housatonic River waterfront living! This beautifully updated home is officially recorded as a 2-bedroom, 2-full-bath residence offering 2,104 total sq. ft. of heated living space, including 1,530 sq. ft. above grade plus 574 heated sq. ft. in the partially finished walk-out lower level. Hardwood floors, a renovated kitchen and bright living spaces welcome you inside. Downstairs, one finished room is currently utilized as additional sleeping space, conveniently located beside a full bath and walk-out, while an adjoining room serves as a podcast/media studio. Officially listed as a 2-bedroom, the flexible lower level offers endless possibilities for guests, office, gym, studio or playroom. Outside, over $100,000 in recent deck, patio and river-facing improvements have transformed the waterfront into an incredible extension of the home. Entertain overlooking the river, enjoy quiet mornings by the water or head down to two private docks for direct Housatonic access. A detached 1-car garage, central air, tankless propane hot water and fully owned, paid-off solar panels with no lease or loan to assume add even more value. Extensively improved inside and out, with two private docks and an impressive 120' of direct Housatonic River frontage, this property makes the most of its exceptional waterfront setting.

Key Facts

City/Town
Seymour
Neighborhood
Squantuck
Property / Style
Single Family · Colonial
Year Built
1948
Days on Market
0 days
Beds
2
Baths
2 full
Living Area
2,108 sq ft
Lot Size
0.13 acres
Property Taxes
$8,727 / Annually

Market Snapshot

The Seymour Market

Single Family · trailing 12 months

Median Days on Market

28

16 active listings

Median $ / Sq Ft

$258

16 active listings

Sale-to-List Ratio

100.0%

138 sales

How this home compares

List Price

$579,000

vs $494,900 median

17.0% above median

Price / Sq Ft

$275

vs $258 median

6.6% above median

Days on Market

0 days

vs 28 days median

28 days fresher than median

Based on 16 active and 138 closed sales (trailing 12 mo) of single family in Seymour. Source: SmartMLS · As of September 3, 2026.

Location

5 Roosevelt Drive, Seymour, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,897

per month

  • Principal & Interest$2,977
  • Property Taxes$727
  • Insurance$193
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Seymour
Neighborhood
Squantuck
County
New Haven

Residence

Property Type
Single Family
Style
Colonial
Year Built
1948
New Construction
No/Resale
Living Area
2,108 sq ft
Below Grade
578 sq ft

Schools

Elementary
Bungay
High
Seymour

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Laundry
Main Level
Appliances
Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
Basement
PartialStorageInterior AccessPartially FinishedWalk-outPartial With Walk-Out

Exterior & Lot

Lot Size
0.13 acres
Zoning
RC-3
Waterfront
Direct waterfront
Waterfront Details
RiverDock or MooringView
Water Source
Public Water Connected
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
BlockConcrete
Exterior Features
PorchDeckGuttersGarden AreaLightingStone WallPatio
Lot Description
Fence - FullWater View

Listing & Financials

Property Taxes
$8,727 / Annually
Days on Market
0
MLS #
24203247
MLS Status
Active

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Listed By

Nick Wilson

(203) 214-4582

Coldwell Banker Realty

(203) 888-1845

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/3/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/3/2026 at 7:10 PM UTC.