Skip to main content

90 Water Street

Chester, Connecticut 06412

ACTIVE$274,900

Reduced from $299,900

Beds
1
Baths
1
SqFt
1,034
Acres
0.28
Year Built
1950
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
WaterfrontVirtual TourPrice Reduced

About This Home

Rare waterfront opportunity! Nestled directly on the water, 90 Water St is a 1-bathroom Ranch currently configured as a 1-bedroom, but offering a spacious layout that easily converts to a 2-bedroom home. Built in 1950, the property provides a fantastic foundational footprint. It features a large 13'6" x 20'10" living room and a versatile 10'3" x 20'10" family room-the ideal space to partition into a second bedroom or home office. A combined 10'5" x 16'2" kitchen/dining area and a comfortable 12'5" x 10'3" primary bedroom complete the interior. Location is everything, and this property delivers. Situated right on the water, it offers tranquil views and the canvas for an incredible outdoor living space on the riverbank. Beyond the backyard, you are just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining. Looking to expand your portfolio or create a larger waterfront compound? This presents a unique dual-purchase opportunity: 90 Water St can be sold as a package with the neighboring property at 92 Water St (note: the two properties conveniently share an existing septic system). Whether you are an investor looking for a value-add rehab project or a buyer seeking a waterfront getaway with a vision to maximize this footprint, the possibilities are endless. Bring your contractor and imagination-schedule a showing today!

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1950
Days on Market
33 days
Beds
1
Baths
1 full
Living Area
1,034 sq ft
Lot Size
0.28 acres
Property Taxes
$3,767 / 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

$274,900

vs $499,000 median

44.9% below median

Price / Sq Ft

$266

vs $269 median

In line with 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

90 Water Street, Chester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,808

per month

  • Principal & Interest$1,402
  • Property Taxes$314
  • Insurance$92
  • 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
Ranch
Year Built
1950
New Construction
No/Resale
Living Area
1,034 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
0.28 acres
Zoning
R-1
Waterfront
Direct waterfront
Waterfront Details
RiverWalk to WaterViewAccess
Water Source
Public Water In StreetPrivate Well
Sewer
Shared Septic
Flood Zone
Yes
Construction
Aluminum
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Level LotWater View

Listing & Financials

Property Taxes
$3,767 / Annually
Days on Market
33
MLS #
24186861
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 5:20 AM UTC.