5 Roosevelt Drive
Seymour, Connecticut 06483
- Beds
- 2
- Baths
- 2
- SqFt
- 2,108
- Acres
- 0.13
- Year Built
- 1948
- Neighborhood
- Squantuck
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
16
22 under contract
Median List Price
$494,900
16 active listings
Median Closed Price
$426,000
138 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per 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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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.