103 Middlesex Ave
Chester, CT 06412
Chester Center
2 Beds
2 Baths
1,350 sqft (on 0.74 acres)
2 Beds
2 Baths
1,350 sqft
(on 0.74 acres)
Local Information
- Map ViewExplore the area around 103 Middlesex Ave.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1958
Lot Size
0.74 acres
Living Area
1,350 sqft
Price/Sqft
$350
Parking
Garage
About this House
Chester Creek water views. Century 21 Heritage Realty 860-526-1200 Visit: [Century 21 Heritage;^http://www.c21heritage.com]
103 Middlesex Ave, Chester, CT 06412 is a 2 bedroom, 2 bathroom, 1,350 sqft single-family home in Chester Center, built in 1958. It last sold for $280,000 on Nov 12, 2009. It is currently off market. The Trulia Estimate is $472,300, with a rent estimate of $2,610/month.
Home Details for 103 Middlesex Ave
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Heating & Cooling Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 1 |
Interior Details Number of Rooms: 6 |
Fireplace & Spa Fireplace |
Security Security System |
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Exterior Home Features Roof: Shake ShingleDeckExterior: OtherPatio |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1958Year Updated: 2002 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
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Lot Area: 0.74 acres |
Price History for 103 Middlesex Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 11/12/2009 | $280,000 | Sold | Smart MLS #M9117897 |
| 10/14/2009 | $289,900 | PriceChange | Agent Provided |
| 08/07/2009 | $299,900 | PriceChange | Agent Provided |
| 05/14/2009 | $319,900 | Listed For Sale | Agent Provided |
| 11/19/1999 | $146,000 | Sold | Smart MLS #E103077 |
Market trends in Chester
Last updated June 2026
Avg. sale price
—
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 | $6,225 |
| Assessment | $229,880 |
Home facts updated by county records
Comparable Sales for 103 Middlesex Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.16 | Single-Family Home | $410,000 | 04/30/26 | 2 | 1 | 1,470 | |
0.36 | Single-Family Home | $252,500 | 11/17/25 | 2 | 1 | 1,012 | |
0.25 | Single-Family Home | $530,000 | 02/26/26 | 3 | 2.5 | 1,664 | |
0.40 | Single-Family Home | $187,000 | 09/04/25 | 3 | 1.5 | 1,170 | |
0.40 | Single-Family Home | $330,000 | 07/28/25 | 2 | 1 | 1,043 | |
0.34 | Single-Family Home | $610,000 | 08/01/25 | 3 | 1.5 | 1,570 | |
0.55 | Single-Family Home | $420,000 | 09/24/25 | 4 | 1.5 | 2,025 | |
0.73 | Single-Family Home | $550,000 | 10/15/25 | 2 | 1.5 | 1,104 | |
0.32 | Single-Family Home | $177,500 | 06/03/26 | 3 | 1 | 1,217 | |
0.70 | Single-Family Home | $345,000 | 08/20/25 | 3 | 2 | 1,472 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETChiarito Real Estate LLC
OFF MARKETWilliam Pitt Sotheby's Int'l
SOLDAPR 30, 2026Compass Connecticut, LLC
OFF MARKETColdwell Banker Realty
SOLDFEB 26, 2026William Raveis Real Estate
OFF MARKETColdwell Banker Realty
SOLDNOV 17, 2025William Pitt Sotheby's Int'l
FOR SALE0.68 ACRESRe/Max Valley Shore
OFF MARKETWilliam Pitt Sotheby's Int'l
Assigned Schools
These are the assigned schools for 103 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 103 Middlesex Ave.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
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Homes for sale near 103 Middlesex Ave
2.39 ACRESWilliam Pitt Sotheby's Int'l
COMING SOON 7/310.58 ACRESRe/Max Valley Shore
NEWOPEN SAT, 3-5PMCOMING SOON 8/10.61 ACRESColdwell Banker Realty
3.2 ACRESChiarito Real Estate LLC
2.71 ACRESWilliam Raveis/First Town RE
See more homes for sale inChester
Off Market Homes Near 103 Middlesex Ave
SOLDJUL 24, 2026Berkshire Hathaway NE Prop.
SOLDJUL 24, 2026William Pitt Sotheby's Int'l- SOLDJUL 24, 2026Compass Connecticut, LLC
SOLDJUL 17, 2026Berkshire Hathaway NE Prop.
SOLDJUL 10, 2026William Raveis Real Estate- See more homes for sale inChester
