90 Water Street
Chester, Connecticut 06412
Reduced from $269,900
- Beds
- 1
- Baths
- 1
- SqFt
- 1,034
- Acres
- 0.28
- Year Built
- 1950
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and comfortable primary bedroom round out the interior. Step outside to direct river frontage with sweeping water views and endless potential for outdoor living on the riverbank. All of this just a short stroll from downtown Chester's boutiques, galleries, and acclaimed restaurants. This property can also be purchased together with the adjacent 92 Water St for a larger waterfront compound (the two share an existing septic system). A fantastic value-add opportunity for an investor or a buyer with vision - bring your contractor and imagination! One of the parties to the LLC has an active real estate license.
Key Facts
- City/Town
- Chester
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1950
- Days on Market
- 57 days
- Beds
- 1
- Baths
- 1 full
- Living Area
- 1,034 sq ft
- Lot Size
- 0.28 acres
- Property Taxes
- $3,864 / Annually
Market Snapshot
The Chester Market
Single Family · trailing 12 months
Active Listings
11
5 under contract
Median List Price
$699,000
11 active listings
Median Closed Price
$564,500
38 sales
Median Days on Market
34
11 active listings
Median $ / Sq Ft
$271
11 active listings
Sale-to-List Ratio
100.0%
38 sales
How this home compares
List Price
$254,900
vs $699,000 median
63.5% below median
Price / Sq Ft
$247
vs $271 median
8.9% below median
Days on Market
57 days
vs 34 days median
23 days longer than median
Based on 11 active and 38 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of October 16, 2026.
Location
90 Water Street, Chester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$1,412
- Property Taxes$322
- Insurance$85
- 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
- Chester
- Middle
- 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
- $3,864 / Annually
- Days on Market
- 57
- MLS #
- 24198111
- MLS Status
- Active
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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 10/16/2026. 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 10/16/2026 at 7:10 PM UTC.