286 Middlesex Tpke
Chester, CT 06412
3 Beds
3.5 Baths
2,800 sqft (on 2.04 acres)
3 Beds
3.5 Baths
2,800 sqft
(on 2.04 acres)
Local Information
- Map ViewExplore the area around 286 Middlesex Tpke.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Charming restored c1790 gambrel with 1982 additions, 3/4 bedrooms,wide board floors,290' direct waterfront,deepwater dock,pool, fabulous!
286 Middlesex Tpke, Chester, CT 06412 is a 3 bedroom, 4 bathroom, 2,800 sqft single-family home built in 1790. It last sold for $1,150,000 on Jul 11, 2002 (10% below the $1,280,000 asking price). It is currently off market. The Trulia Estimate is $1,178,600, with a rent estimate of $4,212/month.
Home Highlights
Parking
Garage
Outdoor
Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 286 Middlesex Tpke
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Interior Details Basement: Full,UnfinishedNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Other |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2800 Square Feet |
Appliances & Utilities Utilities: Cable AvailableAppliances: Dishwasher, Dryer, Microwave, Oven/Range, Refrigerator, Washer, Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 4Has a Fireplace |
View Has a ViewView: Water |
Security Security: Security System |
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Exterior Home Features Patio / Porch: DeckFencing: PartialExterior: GardenGardenHas a Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Detached,Driveway |
Pool Pool: In GroundPool |
Frontage WaterfrontWaterfront: Waterfront, Access, Dock or Mooring, River FrontOn Waterfront |
Water & Sewer Sewer: Septic Tank |
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Year Built Year Built: 1790 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Clapboard |
Property Information Parcel Number: 999999999 |
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Price List Price: $1,280,000 |
Status Change & Dates Off Market Date: Sat Jun 01 2002Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: Chester |
School Information Elementary School: ChesterHigh School: Haddamki |
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Building Area Building Area: 2800 Square Feet |
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Lot Area: 2.04 Acres |
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BasementMls Number: M9066802Attic: Access Via HatchWater ViewWater View: Water |
Last check for updates: about 12 hours ago
Listed by Jennifer Caulfield, (860) 388-7710
Coldwell Banker Realty, (860) 767-2636
Bought with: Sandy Busby, Compass Connecticut, LLC, (203) 245-1593
Source: Smart MLS, MLS#M9066802
Price History for 286 Middlesex Tpke
| Date | Price | Event | Source |
|---|---|---|---|
| 07/11/2002 | $1,150,000 | Sold | Smart MLS #M9066802 |
Market trends in Chester
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
8
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Comparable Sales for 286 Middlesex Tpke
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.39 | Single-Family Home | $410,000 | 09/26/25 | 4 | 3 | 3,343 | |
0.84 | Single-Family Home | $695,000 | 05/15/26 | 4 | 2.5 | 2,029 | |
1.30 | Single-Family Home | $1,275,000 | 12/12/25 | 3 | 3 | 2,664 | |
1.57 | Single-Family Home | $635,000 | 04/30/26 | 3 | 3 | 2,752 | |
1.30 | Single-Family Home | $501,900 | 11/14/25 | 3 | 1.5 | 1,344 | |
1.00 | Single-Family Home | $470,000 | 06/12/26 | 3 | 1.5 | 1,092 | |
1.12 | Single-Family Home | $400,000 | 10/15/25 | 2 | 2 | 2,209 | |
1.28 | Single-Family Home | $469,900 | 12/18/25 | 4 | 2 | 1,516 |
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Assigned Schools
These are the assigned schools for 286 Middlesex Tpke.
- 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 286 Middlesex Tpke.
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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