28 Middlesex Ave
Chester, CT 06412
Chester Center
3 Beds
2.5 Baths
1,582 sqft (on 6.47 acres)
3 Beds
2.5 Baths
1,582 sqft
(on 6.47 acres)
Local Information
- Map ViewExplore the area around 28 Middlesex Ave.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1900
Lot Size
6.47 acres
Living Area
1,582 sqft
Price/Sqft
$286
About this House
Imagine living in a charming 1900's colonial on private 6.47 acres land near historic Chester village Center. Enjoy seasonal views of Connecticut River and Lyme Hilltops . Area of small art galleries, antique shops and tourist and nature lovers attractions. House has convenient first floor Masterbedroom and walk out basement with half bath. This could be the ideal and affordable homestead you have been dreaming of. do not miss it..
28 Middlesex Ave, Chester, CT 06412 is a 3 bedroom, 3 bathroom, 1,582 sqft single-family home in Chester Center, built in 1900. It last sold for $265,000 on Jan 11, 2021. It is currently off market. The Trulia Estimate is $453,000, with a rent estimate of $3,055/month.
Home Details for 28 Middlesex Ave
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Heating & Cooling Heating: OilHeating Fuel: Oil |
Appliances & Utilities DishwasherDryerRefrigeratorWasher |
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Exterior Home Features Roof: AsphaltExterior: Vinyl |
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Year Built Year Built: 1900 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Lot Area: 6.47 acres |
Price History for 28 Middlesex Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 01/11/2021 | $265,000 | Sold | Smart MLS #170333803 |
| 11/25/2020 | $265,000 | Pending | Agent Provided |
| 10/14/2020 | $265,000 | PriceChange | Agent Provided |
| 09/13/2020 | $269,900 | Pending | Agent Provided |
| 09/05/2020 | $269,900 | Listed For Sale | Agent Provided |
| 03/29/2007 | $286,000 | Sold | Smart MLS #M9102502 |
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 | $224 |
| Assessment | $8,260 |
Home facts updated by county records
Comparable Sales for 28 Middlesex Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.23 | Single-Family Home | $446,000 | 10/23/25 | 3 | 3 | 1,876 | |
0.30 | Single-Family Home | $975,000 | 11/17/25 | 4 | 2.5 | 3,149 | |
0.28 | Single-Family Home | $755,000 | 11/19/25 | 3 | 2.5 | 1,896 | |
0.36 | Single-Family Home | $549,000 | 03/24/26 | 3 | 2.5 | 2,202 | |
0.26 | Single-Family Home | $610,000 | 08/01/25 | 3 | 1.5 | 1,570 | |
0.30 | Single-Family Home | $366,000 | 12/29/25 | 2 | 1.5 | 1,081 | |
0.33 | Single-Family Home | $750,000 | 02/20/26 | 3 | 2.5 | 2,888 | |
0.56 | Single-Family Home | $325,000 | 11/26/25 | 3 | 2 | 1,260 | |
0.38 | Single-Family Home | $410,000 | 04/30/26 | 2 | 1 | 1,470 | |
0.46 | Single-Family Home | $780,000 | 01/15/26 | 3 | 2 | 1,772 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETRe/Max Valley Shore
OFF MARKETWilliam Raveis Real Estate
OFF MARKETColdwell Banker Realty
OFF MARKETBerkshire Hathaway NE Prop.
OFF MARKETWilliam Pitt Sotheby's Int'l
OFF MARKETBerkshire Hathaway NE Prop.
OFF MARKETSelect Realty Associates, LLC
OFF MARKETWilliam Pitt Sotheby's Int'l
SOLDNOV 19, 2025William Raveis Real Estate
OFF MARKETProperty Works New England
Assigned Schools
These are the assigned schools for 28 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 28 Middlesex Ave.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
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Homes for sale near 28 Middlesex Ave
NEWCOMING SOON 7/310.58 ACRESRe/Max Valley Shore
COMING SOON 7/252.71 ACRESWilliam Raveis/First Town RE
NEWOPEN SAT, 10-12PMCOMING SOON 7/252.39 ACRESWilliam Pitt Sotheby's Int'l
3.2 ACRESChiarito Real Estate LLC
See more homes for sale inChester
Off Market Homes Near 28 Middlesex Ave
SOLDJUL 24, 2026Compass Connecticut, LLC
SOLDJUL 17, 2026Berkshire Hathaway NE Prop.
SOLDJUL 10, 2026William Raveis Real Estate
SOLDJUL 9, 2026Coldwell Banker Realty
SOLDJUL 8, 2026William Pitt Sotheby's Int'l- See more homes for sale inChester
