# 135 Middlesex Avenue, Chester, CT 06412

> **TL;DR:** 3bd/2ba single family, $475,000 ($400/sqft), built 1920, 1,188 sqft.
> Waterfront, A/C. Est. $2,541/mo. Listed 79 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $475,000 |
| Price/sqft | $400 |
| Bedrooms | 3 |
| Bathrooms | 2 full |
| Square Feet | 1,188 |
| Year Built | 1920 |
| Lot Size | 29,621 sqft (0.68 acres) |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 79 |

## Why This Home Stands Out

- **Waterfront** - Waterfront location listed

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $2,402 |
| Estimated Insurance | $139 |
| **Total** | **$2,541** |

## Nearby Schools

- **Elementary:** Per Board of Ed
- **High:** Per Board of Ed

## Key Amenities

- Waterfront
- A/C

## Property Highlights

- Built in 1920
- 0.68 acre lot
- Waterfront

## Description

### Agent Description
NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new electrical; the updates continued along with a new roof in 2017, and just recently new carpeting on second floor, new stove and microwave plus a new dryer. Bring your creativity to finish the lower walk-out level with its charming brick architecture along with newer radiant-heated, poured concrete floors and french doors -- this could be an amazing walkout steps to the water! This house would be a perfect vacation rental.... Rent a few weeks/Stay a few weeks!

## Location

- **Address:** 135 Middlesex Avenue, Chester, CT 06412
- **County:** Middlesex
- **Coordinates:** 41.410244, -72.440202
- **Google Maps:** https://www.google.com/maps?q=41.410244,-72.440202

## Listing Agent

- **Name:** Lisa Genovali
- **Brokerage:** RE/MAX VALLEY SHORE
- **Phone:** 8605103293
- **Broker Phone:** (860) 388-1228
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/135-Middlesex-Ave_Chester_CT_06412_M49755-86691?f=listhub&s=CTMLS&m=24189125&c=propsimple)

## Photos

![135 Middlesex Avenue - Photo 1](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3848459130r.jpg)

![135 Middlesex Avenue - Photo 2](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f4191294923r.jpg)

![135 Middlesex Avenue - Photo 3](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2281160196r.jpg)

![135 Middlesex Avenue - Photo 4](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f690634774r.jpg)

![135 Middlesex Avenue - Photo 5](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3145428331r.jpg)

![135 Middlesex Avenue - Photo 6](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2309555219r.jpg)

![135 Middlesex Avenue - Photo 7](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3347005504r.jpg)

![135 Middlesex Avenue - Photo 8](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3498008108r.jpg)

![135 Middlesex Avenue - Photo 9](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3758865845r.jpg)

![135 Middlesex Avenue - Photo 10](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3222304853r.jpg)

![135 Middlesex Avenue - Photo 11](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3758865845r.jpg)

![135 Middlesex Avenue - Photo 12](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2533361295r.jpg)

![135 Middlesex Avenue - Photo 13](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2735337570r.jpg)

![135 Middlesex Avenue - Photo 14](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1731788368r.jpg)

![135 Middlesex Avenue - Photo 15](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f8289993r.jpg)

![135 Middlesex Avenue - Photo 16](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2500123578r.jpg)

![135 Middlesex Avenue - Photo 17](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f4012941725r.jpg)

![135 Middlesex Avenue - Photo 18](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2216089692r.jpg)

![135 Middlesex Avenue - Photo 19](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3891731170r.jpg)

![135 Middlesex Avenue - Photo 20](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3399110579r.jpg)

![135 Middlesex Avenue - Photo 21](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2816279961r.jpg)

![135 Middlesex Avenue - Photo 22](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1453618326r.jpg)

![135 Middlesex Avenue - Photo 23](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1418701726r.jpg)

![135 Middlesex Avenue - Photo 24](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3411626329r.jpg)

![135 Middlesex Avenue - Photo 25](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3121692351r.jpg)

![135 Middlesex Avenue - Photo 26](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2043338478r.jpg)

![135 Middlesex Avenue - Photo 27](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1024663817r.jpg)

![135 Middlesex Avenue - Photo 28](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3428501141r.jpg)

![135 Middlesex Avenue - Photo 29](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1689773985r.jpg)

![135 Middlesex Avenue - Photo 30](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1099692815r.jpg)

![135 Middlesex Avenue - Photo 31](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1261687191r.jpg)

![135 Middlesex Avenue - Photo 32](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f2398656237r.jpg)

![135 Middlesex Avenue - Photo 33](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f384257394r.jpg)

![135 Middlesex Avenue - Photo 34](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f3543895040r.jpg)

![135 Middlesex Avenue - Photo 35](http://lh.rdcpix.com/c28ba5911060e9fa9d01bef8b92ffde5l-f1254898180r.jpg)

---

**MLS#:** 24189125 | **Updated:** 2026-09-22
**Source:** listhub

*Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/135-middlesex-avenue-chester-ct-06412-24189125)

---

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