285 South Main Street
Seymour, Connecticut 06483
- Beds
- 5
- Baths
- 2
- SqFt
- 2,310
- Acres
- 0.36
- Year Built
- 1914
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Picture Sunday mornings in the family room, holiday dinners in a separate dining room, and a formal living room set aside for quiet moments or entertaining guests. This 2,310-square-foot Colonial in Seymour offers five bedrooms, with tax records reflecting four legal bedrooms, and two full bathrooms - one on each level - giving every part of the day its own space. Step outside to a large, level yard with room for gardening, play space, or simply open air to enjoy, and a detached garage with a separate work area ready for weekend projects or extra storage. The paid-off solar panels are a quiet, lasting benefit for whoever calls this home next. With space to grow into and make your own, 285 S Main Street is ready for its next chapter. FHA and conventional financing options may open the door for a range of qualified buyers. Come walk through and see how it feels. Please note: The kitchen and bathrooms are outdated, offering the next owner an opportunity to update these spaces over time and make them their own.
Key Facts
- City/Town
- Seymour
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1914
- Days on Market
- 93 days
- Beds
- 5
- Baths
- 2 full
- Living Area
- 2,310 sq ft
- Lot Size
- 0.36 acres
- Garage / Parking
- 1 garage · 8 total
- Property Taxes
- $6,046 / Annually
Market Snapshot
The Seymour Market
Single Family · trailing 12 months
Active Listings
24
18 under contract
Median List Price
$472,500
24 active listings
Median Closed Price
$427,000
141 sales
Median Days on Market
38
24 active listings
Median $ / Sq Ft
$242
24 active listings
Sale-to-List Ratio
100.9%
141 sales
How this home compares
List Price
$374,988
vs $472,500 median
20.6% below median
Price / Sq Ft
$162
vs $242 median
33.1% below median
Days on Market
93 days
vs 38 days median
55 days longer than median
Based on 24 active and 141 closed sales (trailing 12 mo) of single family in Seymour. Source: SmartMLS · As of October 2, 2026.
Location
285 South Main Street, Seymour, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per month
- Principal & Interest$2,053
- Property Taxes$504
- Insurance$125
- 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
- 1914
- New Construction
- No/Resale
- Living Area
- 2,310 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Seymour
Interior
- Heating
- Hot Water
- Heat Fuel
- OilSolarOther
- Cooling
- None
- Fireplaces
- 1
- Laundry Location
- Basement
- Appliances
- Electric RangeRange HoodRefrigerator
- Basement
- FullUnfinished
- In-Law Apartment
- PossibleSeparate Entry
Exterior & Lot
- Lot Size
- 0.36 acres
- Zoning
- R-18
- Garage / Parking
- 1 garage space8 total parking spacesDetached GarageDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Lightly Wooded
Listing & Financials
- Property Taxes
- $6,046 / Annually
- Days on Market
- 93
- MLS #
- 24188227
- MLS Status
- Active
Similar Properties
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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 10/2/2026. 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 10/2/2026 at 7:51 PM UTC.