92 Water Street
Chester, Connecticut 06412
Reduced from $324,900
- Beds
- 3
- Baths
- 1
- SqFt
- 1,217
- Acres
- 0.27
- Year Built
- 1927
- 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
Welcome to 92 Water St, a charming 1927 two-story Colonial offering a rare opportunity to own waterfront property in picturesque Chester, CT! This 3-bedroom, 1-bathroom home is perfectly situated right on the water, offering tranquil riverfront views and an unbeatable location just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining. Sitting on an 11,761 sq. ft. (0.27-acre) lot bounded directly by the water, this home features classic vinyl siding, a paved driveway, and a comfortable layout, making it a fantastic canvas for your dream riverfront retreat. Whether you are an investor seeking a value-add property or a homeowner looking for direct water access, the potential here is outstanding. Looking to expand your portfolio or create a larger waterfront compound? This property presents a unique dual-purchase opportunity: 92 Water St can be sold as a package with the neighboring property at 90 Water St. Buyers should note that the two properties conveniently share an existing septic system. This rare Chester waterfront offering is packed with potential and won't last long. Bring your vision and schedule your showing today!
Key Facts
- City/Town
- Chester
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1927
- Days on Market
- 33 days
- Beds
- 3
- Baths
- 1 full
- Living Area
- 1,217 sq ft
- Lot Size
- 0.27 acres
- Property Taxes
- $4,104 / Annually
Market Snapshot
The Chester Market
Single Family · trailing 12 months
Active Listings
9
4 under contract
Median List Price
$499,000
9 active listings
Median Closed Price
$610,000
36 sales
Median Days on Market
33
9 active listings
Median $ / Sq Ft
$269
9 active listings
Sale-to-List Ratio
100.0%
36 sales
How this home compares
List Price
$299,900
vs $499,000 median
39.9% below median
Price / Sq Ft
$246
vs $269 median
8.6% below median
Days on Market
33 days
vs 33 days median
In line with median
Based on 9 active and 36 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of July 28, 2026.
Location
92 Water Street, Chester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,529
- Property Taxes$342
- Insurance$100
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chester
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1927
- New Construction
- No/Resale
- Living Area
- 1,217 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- None
- Appliances
- Oven/RangeRefrigerator
- Basement
- Crawl Space
Exterior & Lot
- Lot Size
- 0.27 acres
- Zoning
- R-1
- Waterfront
- Direct waterfront
- Waterfront Details
- RiverWalk to WaterView
- Water Source
- Public Water In StreetPrivate Well
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Water View
Listing & Financials
- Property Taxes
- $4,104 / Annually
- Days on Market
- 33
- MLS #
- 24186867
- 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 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 6:10 AM UTC.