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92 Water Street

Chester, Connecticut 06412

ACTIVE$299,900

Reduced from $324,900

Beds
3
Baths
1
SqFt
1,217
Acres
0.27
Year Built
1927
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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WaterfrontVirtual TourPrice Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,971

per 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

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

Listed By

Luke Florian

(860) 877-5800

SSG Real Estate LLC

(860) 657-4754

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.