3-5 Pearl Street
Seymour, Connecticut 06483
- Beds
- 6
- Baths
- 3 | 1
- SqFt
- 3,237
- Acres
- 0.29
- Year Built
- 1795
- Property Type
- 2 Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Invest in a piece of Seymour's history! 3-5 Pearl Street is an iconic two-family home seated just outside of downtown Seymour. Originally built in 1795 (per tax records), but she's a lady who certainly doesn't show her age. The picture-perfect curb appeal has made this home a landmark of the area, perched on the corner of Pearl and South Main. Two pristine ~1570 sq. ft. units sit side by side, making it a fantastic option for owner occupancy while offsetting your mortgage with rental income. 3 Pearl features a living room, large dining room, expansive kitchen, 3 bedrooms, a flex room, and two full bathrooms with a large, level side yard area. 5 Pearl features a mirrored layout, also with 3 bedrooms, but subbing in 1.5 bathrooms. Both units include walk-up attic space and basement access for lots of storage room. A detached 2-car garage provides additional income opportunity or room for hobbyists. Walking distance to the new Big Dipper Ice Cream and minutes from Rt. 8, the Seymour train station, Zoi's Pizza, and Bank Street's shops & services.
Key Facts
- City/Town
- Seymour
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units are Side-by-Side
- Year Built
- 1795
- Days on Market
- 72 days
- Beds
- 6
- Baths
- 3 full · 1 half
- Living Area
- 3,237 sq ft
- Lot Size
- 0.29 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $5,542 / Annually
Market Snapshot
The Seymour Market
Multi-Family · trailing 12 months
Active Listings
1
1 under contract
Median List Price
$530,000
1 active listing
Median Closed Price
$440,000
17 sales
Median Days on Market
0
1 active listing
Median $ / Sq Ft
$294
1 active listing
Sale-to-List Ratio
100.6%
17 sales
How this home compares
List Price
$540,000
vs $530,000 median
In line with median
Price / Sq Ft
$167
vs $294 median
43.2% below median
Days on Market
--
vs 0 days median
Limited comparable data
Based on 1 active and 17 closed sales (trailing 12 mo) of multi-family in Seymour. Source: SmartMLS · As of August 15, 2026.
Location
3-5 Pearl Street, Seymour, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$2,779
- Property Taxes$462
- Insurance$180
- 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
- Multi-Family
- Subtype
- Duplex
- Style
- Units are Side-by-Side
- Year Built
- 1795
- New Construction
- No/Resale
- Living Area
- 3,237 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- BaseboardHot Air
- Heat Fuel
- Oil
- Cooling
- None
- Laundry
- Washer/Dryer All Units
- Laundry Location
- main level bathroomsboth units
- Basement
- FullInterior AccessConcrete Floor
Exterior & Lot
- Lot Size
- 0.29 acres
- Zoning
- R-18
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Shingle
- Color
- Blue
- Roof
- Asphalt Shingle
- Foundation
- BrickStone
- Exterior Features
- Porch
- Lot Description
- Corner Lot
Listing & Financials
- Property Taxes
- $5,542 / Annually
- Days on Market
- 72
- MLS #
- 24181034
- MLS Status
- Under Contract - Continue to Show
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/15/2026. 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 8/15/2026 at 5:35 AM UTC.