21 Middlesex Ave
Chester, CT 06412
Chester Center
3 Beds
4 Baths
1,464 sqft (on 1.25 acres)
3 Beds
4 Baths
1,464 sqft
(on 1.25 acres)
Local Information
- Map ViewExplore the area around 21 Middlesex Ave.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
This single-family home is located at 21 Middlesex Ave, Chester, CT. 21 Middlesex Ave is in the Chester Center neighborhood in Chester, CT and in ZIP code 06412. This property has 3 bedrooms, 4 bathrooms and approximately 1,464 sqft of floor space. This property has a lot size of 1.25 acres and was built in 1968.
21 Middlesex Ave, Chester, CT 06412 is a 3 bedroom, 4 bathroom, 1,464 sqft single-family home in Chester Center, built in 1968. It last sold for $250,000 on Jun 27, 2005. It is currently off market. The Trulia Estimate is $513,000, with a rent estimate of $2,991/month.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 21 Middlesex Ave
|
|---|
Heating & Cooling Heating: Forced Air, ElectricHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 1 |
Interior Details Number of Rooms: 8 |
Fireplace & Spa Fireplace |
|
|---|
Exterior Home Features Roof: Shake ShingleExterior: Wood |
Parking & Garage GarageParking: Garage Attached |
|
|---|
Year Built Year Built: 1968Year Updated: 1994 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
|
|---|
Lot Area: 1.25 acres |
Price History for 21 Middlesex Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 06/27/2005 | $250,000 | Sold | Smart MLS #M9085994 |
Market trends in Chester
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
8
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $6,216 |
| Assessment | $229,530 |
Home facts updated by county records
Comparable Sales for 21 Middlesex Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.26 | Single-Family Home | $755,000 | 11/19/25 | 3 | 2.5 | 1,896 | |
0.19 | Single-Family Home | $446,000 | 10/23/25 | 3 | 3 | 1,876 | |
0.36 | Single-Family Home | $549,000 | 03/24/26 | 3 | 2.5 | 2,202 | |
0.33 | Single-Family Home | $750,000 | 02/20/26 | 3 | 2.5 | 2,888 | |
0.48 | Single-Family Home | $810,000 | 11/14/25 | 3 | 3.5 | 2,322 | |
0.66 | Single-Family Home | $540,000 | 06/22/26 | 3 | 1.5 | 1,392 | |
0.33 | Single-Family Home | $610,000 | 08/01/25 | 3 | 1.5 | 1,570 | |
0.46 | Single-Family Home | $410,000 | 04/30/26 | 2 | 1 | 1,470 | |
0.27 | Single-Family Home | $366,000 | 12/29/25 | 2 | 1.5 | 1,081 | |
0.52 | Single-Family Home | $325,000 | 11/26/25 | 3 | 2 | 1,260 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETRe/Max Valley Shore
OFF MARKETBerkshire Hathaway NE Prop.
OFF MARKETWilliam Raveis Real Estate
OFF MARKETColdwell Banker Realty
OFF MARKETWilliam Pitt Sotheby's Int'l
OFF MARKETWilliam Raveis Real Estate
OFF MARKETProperty Works New England
OFF MARKETSelect Realty Associates, LLC
SOLDDEC 29, 2025William Raveis Real Estate
OFF MARKETCalcagni Real Estate
Assigned Schools
These are the assigned schools for 21 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 21 Middlesex Ave.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
APPLY INSTANTLY
APPLY INSTANTLY
See more homes for rent inChester
Homes for sale near 21 Middlesex Ave
COMING SOON 7/60.52 ACRESCompass Connecticut, LLC
3.2 ACRESChiarito Real Estate LLC
4.4 ACRESWilliam Raveis Real Estate
OPEN SAT, 12-3PMCOMING SOON 7/91.8 ACRESWilliam Raveis Real Estate
0.45 ACRESWilliam Pitt Sotheby's Int'l
See more homes for sale inChester
Off Market Homes Near 21 Middlesex Ave
SOLDJUL 2, 2026William Pitt Sotheby's Int'l
SOLDJUN 29, 2026William Raveis Real Estate
SOLDJUN 25, 2026William Raveis Real Estate
SOLDJUN 25, 2026Compass Connecticut, LLC
SOLDJUN 22, 2026William Pitt Sotheby's Int'l
SOLDJUN 15, 2026Coldwell Banker Realty
SOLDJUN 12, 2026Great Estates, CT- See more homes for sale inChester
