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3 Roosevelt Drive

Seymour, Connecticut 06483

ACTIVE$585,000

Reduced from $674,900

Beds
2
Baths
1 | 1
SqFt
1,431
Acres
0.19
Year Built
1900
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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WaterfrontDock / Mooring2-Car Garage1 FireplacePrice Reduced

About This Home

Experience waterfront living at its finest in this exceptional DIRECT WATERFRONT home on the beautiful Housatonic River. Offering a rare combination of a private sandy beach, two floating docks with room for up to four boats, and breathtaking water views, this property is perfect for boating, kayaking, fishing, or simply relaxing by the river. The outdoor space is designed for entertaining with expansive Trex decking, floating walkways, a hot tub overlooking the water, gazebo, raised garden beds, and a beautifully landscaped yard. An oversized detached garage, additional one-car garage, lean-to, and pull-through driveway provide exceptional storage and parking for vehicles, boats, and recreational equipment. Inside, the bright and inviting 2-bedroom, 1.5-bath home features an open-concept layout filled with natural light, recessed lighting, tinted windows, and custom blinds. The kitchen flows seamlessly into the living area, creating an ideal space for everyday living and entertaining. Recent updates include a metal roof, siding and mini-split heating and cooling systems (2017), and a Blaze King wood stove (2023). The finished lower level offers additional living space with a propane stove, electric heat, and plenty of storage. Whether you're looking for a year-round residence or a weekend retreat, this one-of-a-kind waterfront property offers the perfect blend of comfort, recreation, and unforgettable riverfront views.

Key Facts

City/Town
Seymour
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1900
Days on Market
79 days
Beds
2
Baths
1 full · 1 half
Living Area
1,431 sq ft
Lot Size
0.19 acres
Garage / Parking
2 garage
Property Taxes
$6,652 / Annually

Market Snapshot

The Seymour Market

Single Family · trailing 12 months

Median Days on Market

24

19 active listings

Median $ / Sq Ft

$231

19 active listings

Sale-to-List Ratio

100.2%

128 sales

How this home compares

List Price

$585,000

vs $499,000 median

17.2% above median

Price / Sq Ft

$409

vs $231 median

77.1% above median

Days on Market

79 days

vs 24 days median

55 days longer than median

Based on 19 active and 128 closed sales (trailing 12 mo) of single family in Seymour. Source: SmartMLS · As of July 28, 2026.

Location

3 Roosevelt Drive, Seymour, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,732

per month

  • Principal & Interest$2,983
  • Property Taxes$554
  • Insurance$195
  • HOA$0

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

Location

City/Town
Seymour
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Colonial
Year Built
1900
New Construction
No/Resale
Living Area
1,431 sq ft

Schools

Elementary
Per Board of Ed
High
Seymour

Interior

Heating
BaseboardHeat PumpWood/Coal Stove
Heat Fuel
ElectricWood
Cooling
Ceiling FansSplit System
Fireplaces
1
Laundry
Main Level
Appliances
Gas RangeMicrowaveRefrigeratorWasherDryer
Basement
PartialStoragePartially Finished
Interior Features
Open Floor PlanSecurity System

Exterior & Lot

Lot Size
0.19 acres
Zoning
RC-3
Garage / Parking
2 garage spacesDetached Garage
Waterfront
Direct waterfront
Waterfront Details
RiverBeachWalk to WaterDock or MooringViewAccess
Water Source
Public Water Connected
Sewer
Septic
Construction
Vinyl Siding
Roof
Metal
Foundation
Concrete
Exterior Features
BalconyBreezewayShedGazeboDeckHot Tub
Lot Description
Level LotWater View

Listing & Financials

Property Taxes
$6,652 / Annually
Days on Market
79
MLS #
24173848
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Emily Fitzgerald

(203) 802-8401

William Raveis Real Estate

(203) 264-8180

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:15 AM UTC.