18 Middlesex Ave
Chester, CT 06412
Chester Center
5 Beds
3 Baths
2,202 sqft (on 1.01 acres)
5 Beds
3 Baths
2,202 sqft
(on 1.01 acres)
Local Information
- Map ViewExplore the area around 18 Middlesex Ave.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1941
Lot Size
1.01 acres
Living Area
2,202 sqft
Price/Sqft
$289
Parking
Garage
Description
This single-family home is located at 18 Middlesex Ave, Chester, CT. 18 Middlesex Ave is in the Chester Center neighborhood in Chester, CT and in ZIP code 06412. This property has 5 bedrooms, 3 bathrooms and approximately 2,202 sqft of floor space. This property has a lot size of 1.01 acres and was built in 1941.
18 Middlesex Ave, Chester, CT 06412 is a 5 bedroom, 3 bathroom, 2,202 sqft single-family home in Chester Center, built in 1941. It last sold for $91,000 on Mar 31, 1998. It is currently off market. The Trulia Estimate is $637,200, with a rent estimate of $3,653/month.
Home Details for 18 Middlesex Ave
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Interior Details BasementNumber of Rooms: 11 |
Heating & Cooling Heating: Other, OilHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Fireplace & Spa Fireplace |
Security Security System |
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Exterior Home Features Roof: SlateDeckExterior: Wood |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1941Year Updated: 1994 |
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod |
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Units in Building: 1 |
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Lot Area: 1.01 acres |
Price History for 18 Middlesex Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 03/31/1998 | $91,000 | Sold | N/A |
Market trends in Chester
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
8
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $8,155 |
| Assessment | $301,140 |
Home facts updated by county records
Comparable Sales for 18 Middlesex Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.35 | Single-Family Home | $755,000 | 11/19/25 | 3 | 2.5 | 1,896 | |
0.43 | Single-Family Home | $549,000 | 03/24/26 | 3 | 2.5 | 2,202 | |
0.41 | Single-Family Home | $750,000 | 02/20/26 | 3 | 2.5 | 2,888 | |
0.28 | Single-Family Home | $446,000 | 10/23/25 | 3 | 3 | 1,876 | |
0.55 | Single-Family Home | $810,000 | 11/14/25 | 3 | 3.5 | 2,322 | |
0.36 | Single-Family Home | $975,000 | 11/17/25 | 4 | 2.5 | 3,149 | |
0.35 | Single-Family Home | $610,000 | 08/01/25 | 3 | 1.5 | 1,570 | |
0.81 | Single-Family Home | $495,000 | 03/03/26 | 3 | 2.5 | 2,018 | |
0.72 | Single-Family Home | $860,000 | 09/17/25 | 3 | 2.5 | 2,344 | |
0.21 | Single-Family Home | $366,000 | 12/29/25 | 2 | 1.5 | 1,081 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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OFF MARKETWilliam Pitt Sotheby's Int'l
OFF MARKETDB Associates of CT, LLC
Assigned Schools
These are the assigned schools for 18 Middlesex Ave.
- John Winthrop Middle School
- 7-8
- Public
- 197 Students
4/10GreatSchools RatingParent Rating AverageI think bullying was the worst problem that happened during my time at JWMS. The adult authorities at the school had a difficult time understanding situations and that often made it worse. I'm also not stating that it was just the kids at the school who would bully but it was also teachers. I remember my 8th grade science teacher would verbally bully girls and pick on them, and it was always girls he was picking on. I was one of them. It didn't help that I had a counselor who couldn't care less if one of there students just jumped off a bridge. They could care less of there students well being, and the same goes with the principles. I honestly would recommend going to a different school, I mean unless you want your child to become depressed.Other Review8y ago - Valley Regional High School
- 9-12
- Public
- 429 Students
7/10GreatSchools RatingParent Rating AverageI enjoyed going to Valley. It is different as a parent I see things differently. However compared to other schools I would say Valley is above the rest.Parent Review7y ago - Chester Elementary School
- PK-6
- Public
- 198 Students
7/10GreatSchools RatingParent Rating AverageCES has a lot of potential with the proper leadership, which it lacks.Other Review6y ago 
Check out schools near 18 Middlesex Ave.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
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Off Market Homes Near 18 Middlesex Ave
SOLDJUL 17, 2026Berkshire Hathaway NE Prop.
SOLDJUL 13, 2026William Pitt Sotheby's Int'l
SOLDJUL 13, 2026William Raveis Real Estate
SOLDJUL 10, 2026Premier Re Group LLC
SOLDJUL 10, 2026William Raveis Real Estate- See more homes for sale inChester
