90 Water Street
Chester, Connecticut 06412
Reduced from $299,900
- Beds
- 1
- Baths
- 1
- SqFt
- 1,034
- Acres
- 0.28
- Year Built
- 1950
- 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
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
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
$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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 5:20 AM UTC.