181 Middlesex Avenue
Chester, CT 06412
3 Beds
1 Bath
1,232 sqft (on 0.83 acres)
3 Beds
1 Bath
1,232 sqft
(on 0.83 acres)
Local Information
- Map ViewExplore the area around 181 Middlesex Avenue.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Enjoy Chester close to shopping, restaurants, Parks. Centrally located between Boston, and NYC> Home is in need of some updating, and is being sold as is. Ready to conform to your taste, pick out the rooms colors, and make this your new dream home in Chester.
181 Middlesex Avenue, Chester, CT 06412 is a 3 bedroom, 1 bathroom, 1,232 sqft single-family home built in 1956. It last sold for $225,000 on Oct 31, 2023 (13% below the $259,000 asking price). It is currently off market. The Trulia Estimate is $347,300, with a rent estimate of $2,501/month.
Home Highlights
Parking
Open Parking
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 181 Middlesex Avenue
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Interior Details Basement: Full,Unfinished,Interior EntryNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Sun Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1 |
Dimensions and Layout Living Area: 1232 Square Feet |
Appliances & Utilities Appliances: Gas Range, Oven/Range, Refrigerator, Dishwasher, Dryer, Water Heater, Electric Water HeaterDishwasherDryerLaundry: Lower LevelRefrigerator |
Heating & Cooling Heating: Forced Air,OilHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Forced Air |
Fireplace & Spa No Fireplace |
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Exterior Home Features Roof: Asphalt ShinglePatio / Porch: DeckExterior: Fruit Trees, Garden, Rain GuttersFoundation: Block, Concrete PerimeterGardenNo Private Pool |
Parking & Garage No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway,Unpaved,Off Street |
Frontage Waterfront: BrookNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 1232 Square Feet |
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Year Built Year Built: 1956 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch |
Building Construction Materials: Aluminum Siding, Block, ConcreteNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 941438 |
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Price List Price: $259,000 |
Status Change & Dates Off Market Date: Fri Sep 22 2023Possession Timing: Immediately After Closing |
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MLS Status: Closed |
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Direction & Address City: Chester |
School Information Elementary School: ChesterHigh School: Valley |
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Buyer Agent Buyer Company Name: Linda's Team at William Raveis Real Estate |
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Building Area Building Area: 1232 Square Feet |
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Community Features: Near Public Transport, Park, Pool |
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No HOA |
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Lot Area: 0.83 acres |
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BasementMls Number: 170594684Attic: Pull Down StairsAbove Grade Unfinished Area: 1232 |
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Near Public TransportParkPool |
Last check for updates: about 13 hours ago
Listed by Sam Robinson, (860) 388-3936
William Raveis Real Estate, (860) 388-3936
Bought with: Benjamin T. Zupan, (860) 324-7142, William Raveis Real Estate, (860) 388-3936
Source: Smart MLS, MLS#170594684
Price History for 181 Middlesex Avenue
| Date | Price | Event | Source |
|---|---|---|---|
| 10/31/2023 | $225,000 | Sold | Smart MLS #170594684 |
| 09/23/2023 | $259,000 | Pending | Smart MLS #170594684 |
| 09/02/2023 | $259,000 | Listed For Sale | Smart MLS #170594684 |
| 05/22/1995 | $122,000 | Sold | N/A |
| 08/26/1993 | $95,000 | Sold | N/A |
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 | $4,584 |
| Assessment | $169,260 |
Home facts updated by county records
Comparable Sales for 181 Middlesex Avenue
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.45 | Single-Family Home | $177,500 | 06/03/26 | 3 | 1 | 1,217 | |
0.35 | Single-Family Home | $187,000 | 09/04/25 | 3 | 1.5 | 1,170 | |
0.27 | Single-Family Home | $470,000 | 06/12/26 | 3 | 1.5 | 1,092 | |
0.40 | Single-Family Home | $420,000 | 09/24/25 | 4 | 1.5 | 2,025 | |
0.80 | Single-Family Home | $252,500 | 11/17/25 | 2 | 1 | 1,012 | |
0.15 | Single-Family Home | $469,900 | 12/18/25 | 4 | 2 | 1,516 | |
0.46 | Single-Family Home | $177,500 | 06/03/26 | 1 | 1 | 1,034 | |
0.56 | Single-Family Home | $530,000 | 02/26/26 | 3 | 2.5 | 1,664 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETGenovali Realty, Inc.
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FOR SALENEW - 2 DAYS AGO0.43 ACRESRe/Max Valley Shore- OFF MARKETBerkshire Hathaway NE Prop.
SOLDJUN 12, 2026Great Estates, CT
OFF MARKETWilliam Pitt Sotheby's Int'l
Assigned Schools
These are the assigned schools for 181 Middlesex Avenue.
- 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 181 Middlesex Avenue.
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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Off Market Homes Near 181 Middlesex Avenue
SOLDJUL 6, 2026Berkshire Hathaway NE Prop.
SOLDJUN 30, 2026Berkshire Hathaway NE Prop.
SOLDJUN 29, 2026William Raveis Real Estate- SOLDJUN 12, 2026Great Estates, CT
SOLDJUN 9, 2026Berkshire Hathaway NE Prop.- SOLDJUN 8, 2026
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