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90 Water Street

Chester, Connecticut 06412

ACTIVE - NEW$269,900
Beds
1
Baths
1
SqFt
1,034
Acres
0.28
Year Built
1950
Matt Caiola

Matt Caiola

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Waterfront

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!

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1950
Days on Market
0 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

61

7 active listings

Median $ / Sq Ft

$290

7 active listings

Sale-to-List Ratio

100.0%

34 sales

How this home compares

List Price

$269,900

vs $650,000 median

58.5% below median

Price / Sq Ft

$261

vs $290 median

10.0% below median

Days on Market

0 days

vs 61 days median

61 days fresher than median

Based on 7 active and 34 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of August 20, 2026.

Location

90 Water Street, Chester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,793

per month

  • Principal & Interest$1,389
  • Property Taxes$314
  • Insurance$90
  • 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
$3,767 / Annually
Days on Market
0
MLS #
24198111
MLS Status
Active

Similar Properties

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Listed By

Ryan O'Keeffe

(203) 297-0849

Salzillo Realty Company

(860) 637-1379

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/20/2026. 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 8/20/2026 at 6:20 AM UTC.