37 Middlesex Ave
Chester, CT 06412
Chester Center
5 Beds
4 Baths
3,523 sqft (on 0.75 acres)
5 Beds
4 Baths
3,523 sqft
(on 0.75 acres)
Local Information
- Map ViewExplore the area around 37 Middlesex Ave.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1910
Lot Size
0.75 acres
Living Area
3,523 sqft
Price/Sqft
$227
Parking
Garage
About this House
This single-family home is located at 37 Middlesex Ave, Chester, CT. 37 Middlesex Ave is in the Chester Center neighborhood in Chester, CT and in ZIP code 06412. This property has 5 bedrooms, 4 bathrooms and approximately 3,523 sqft of floor space. This property has a lot size of 0.75 acres and was built in 1910.
37 Middlesex Ave, Chester, CT 06412 is a 5 bedroom, 4 bathroom, 3,523 sqft single-family home in Chester Center, built in 1910. It last sold for $262,500 on Oct 18, 1993. It is currently off market. The Trulia Estimate is $801,400, with a rent estimate of $4,565/month.
Home Details for 37 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: Shake ShingleExterior: WoodPatio |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1910Year Updated: 1991 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
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Units in Building: 1 |
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Lot Area: 0.75 acres |
Price History for 37 Middlesex Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 10/18/1993 | $262,500 | 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 | $10,323 |
| Assessment | $381,220 |
Home facts updated by county records
Comparable Sales for 37 Middlesex Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.25 | Single-Family Home | $750,000 | 02/20/26 | 3 | 2.5 | 2,888 | |
0.39 | Single-Family Home | $810,000 | 11/14/25 | 3 | 3.5 | 2,322 | |
0.28 | Single-Family Home | $549,000 | 03/24/26 | 3 | 2.5 | 2,202 | |
0.22 | Single-Family Home | $755,000 | 11/19/25 | 3 | 2.5 | 1,896 | |
0.20 | Single-Family Home | $446,000 | 10/23/25 | 3 | 3 | 1,876 | |
0.18 | Single-Family Home | $610,000 | 08/01/25 | 3 | 1.5 | 1,570 | |
0.26 | Single-Family Home | $975,000 | 11/17/25 | 4 | 2.5 | 3,149 | |
0.57 | Single-Family Home | $860,000 | 09/17/25 | 3 | 2.5 | 2,344 | |
0.32 | Single-Family Home | $410,000 | 04/30/26 | 2 | 1 | 1,470 | |
0.71 | Single-Family Home | $530,000 | 02/26/26 | 3 | 2.5 | 1,664 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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SOLDNOV 19, 2025William Raveis Real Estate
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Assigned Schools
These are the assigned schools for 37 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 37 Middlesex Ave.
Neighborhood Overview
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Homes for sale near 37 Middlesex Ave
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2.71 ACRESWilliam Raveis/First Town RE
3.2 ACRESChiarito Real Estate LLC
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Off Market Homes Near 37 Middlesex Ave
SOLDJUL 24, 2026William Raveis Real Estate
SOLDJUL 24, 2026William Pitt Sotheby's Int'l- SOLDJUL 24, 2026Compass Connecticut, LLC
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SOLDJUL 13, 2026William Pitt Sotheby's Int'l
SOLDJUL 13, 2026William Raveis Real Estate- See more homes for sale inChester
