288 Middlesex Ave
Chester, CT 06412
5 Beds
6 Baths
6,000 sqft (on 3 acres)
5 Beds
6 Baths
6,000 sqft
(on 3 acres)
Local Information
- Map ViewExplore the area around 288 Middlesex Ave.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1800
Lot Size
3 acres
Living Area
6,000 sqft
Price/Sqft
$288
Parking
Garage
About this House
This single-family home is located at 288 Middlesex Ave, Chester, CT. 288 Middlesex Ave is in Chester, CT and in ZIP code 06412. This property has 5 bedrooms, 6 bathrooms and approximately 6,000 sqft of floor space. This property has a lot size of 3.00 acres and was built in 1800.
288 Middlesex Ave, Chester, CT 06412 is a 5 bedroom, 6 bathroom, 6,000 sqft single-family home built in 1800. It last sold for $925,000 on Jun 18, 2009. It is currently off market. The Trulia Estimate is $1,729,700, with a rent estimate of $6,310/month.
Home Details for 288 Middlesex Ave
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Interior Details BasementAtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, Workshop, Sun RoomWet BarCeiling Fan |
Heating & Cooling Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Hardwood |
Appliances & Utilities Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa FireplaceHot Tub or SpaJetted Bath Tub |
Windows, Doors, Floors & Walls Double Paned Windows |
Security Security System |
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Exterior Home Features Roof: AsphaltDeckExterior: Shingle, Stone, Wood, CompositionGardenLawnPatioSprinkler System |
Parking & Garage GarageParking Spaces: 5Parking: Garage Attached, Garage Detached |
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Year Built Year Built: 1800Year Updated: 2009 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Lot Area: 3.00 acres |
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Intercom |
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Pool Sauna |
Price History for 288 Middlesex Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 12/27/2025 | $3,375,000 | ListingRemoved | Smart MLS #24124960 |
| 09/11/2025 | $3,375,000 | Listed For Sale | Smart MLS #24124960 |
| 06/18/2009 | $925,000 | Sold | Smart MLS #M9114783 |
Market trends in Chester
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
8
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $24,724 |
| Assessment | $913,010 |
Home facts updated by county records
Comparable Sales for 288 Middlesex Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.42 | Single-Family Home | $410,000 | 09/26/25 | 4 | 3 | 3,343 | |
0.69 | Single-Family Home | $515,000 | 07/27/26 | 3 | 3 | 2,971 | |
0.79 | Single-Family Home | $540,000 | 06/25/26 | 4 | 3 | 3,906 | |
0.87 | Single-Family Home | $695,000 | 05/15/26 | 4 | 2.5 | 2,029 | |
0.51 | Single-Family Home | $229,000 | 11/25/25 | 2 | 1.5 | 1,617 | |
0.65 | Single-Family Home | $310,000 | 02/12/26 | 3 | 3 | 1,241 | |
1.34 | Single-Family Home | $1,275,000 | 12/12/25 | 3 | 3 | 2,664 | |
1.06 | Single-Family Home | $900,000 | 07/10/26 | 2 | 1 | 2,736 | |
1.32 | Single-Family Home | $469,900 | 12/18/25 | 4 | 2 | 1,516 | |
1.32 | Single-Family Home | $501,900 | 11/14/25 | 3 | 1.5 | 1,344 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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Assigned Schools
These are the assigned schools for 288 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 288 Middlesex Ave.
What Locals Say about Chester
At least 14 Trulia users voted on each feature.
95 % Say car is needed
94 % Say it's dog friendly
93 % Say there's holiday spirit
93 % Say yards are well-kept
84 % Say people would walk alone at night
79 % Say parking is easy
78 % Say they plan to stay for at least 5 years
74 % Say it's walkable to restaurants
74 % Say there's wildlife
69 % Say it's quiet
63 % Say neighbors are friendly
59 % Say there are sidewalks
52 % Say kids play outside
44 % Say streets are well-lit
37 % Say there are community events
18 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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