96 Middlesex Avenue
Chester, CT 06412
Chester Center
4 Beds
3.5 Baths
3,153 sqft (on 6.26 acres)
4 Beds
3.5 Baths
3,153 sqft
(on 6.26 acres)
Local Information
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Description
Steeped in history, awash in modern amenities and conveniences, this 4 bed (2 en suite), 3 1/2 bath converted barn sits on over six acres just a spit from the Connecticut River and the quintessential town of Chester. The current homeowner's goal was to gently nudge the 1830s cider mill into this century with thought, care, and charm salvaging and repurposing as many original features as feasible. The transformation included removal of randomly erected partition walls throughout, and reworking the floor plan. Original wall planks were unearthed, hand sawn chestnut flooring was restored, and extra planks were used to create mantles for the 2 fireplaces. The live-edge sheathing in the ceiling was preserved giving the space simultaneously a sense of grandiosity and warmth. The resulting home is an inviting and comfortable retreat for a few or a fabulous entertaining space for many. From the oversized deck complete with outdoor kitchen, look out over the vast field and watch the wildlife including foxes, deer, bobcats, coyotes, American Kestrels, goldfinch and eastern bluebirds, possums, raccoons and more. A few apple trees remain, the fields slope and undulate untouched by time. Enjoy a cup of coffee or a glass of wine in the gazebo or al fresco next to 'frog pond' or as you meander along the path around the pasture. The fully updated estate with new HVAC, roof, solar, kitchen, bathrooms, outdoor shower, electrical, plumbing and septic system is ready for your vision; do you desire a pool, family compound, gentleman's farm, tennis court, animal sanctuary....? Your dreams are calling and this property can make them a reality. Land is sub-dividable, preliminary plans available.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from January 31, 2025
Home Highlights
Parking
2 Car Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 96 Middlesex Avenue
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Interior Details Basement: Full,Partially FinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Sun Room |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 3153 Square Feet |
Appliances & Utilities Appliances: Gas Cooktop, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Electric,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 2Has a Fireplace |
Windows, Doors, Floors & Walls Door: French Doors |
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Exterior Home Features Roof: AsphaltPatio / Porch: Porch, Wrap Around, Deck, PatioOther Structures: GazeboExterior: GardenFoundation: StoneGardenNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Off Street,Driveway,Private |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Farm & Range Horse Amenities: PaddocksAllowed to Raise Horses |
Finished Area Finished Area (above surface): 3153 Square Feet |
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Year Built Year Built: 1830 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Antique,Barn |
Building Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 941342 |
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Price List Price: $1,375,000 |
Status Change & Dates Off Market Date: Mon Jan 20 2025Possession Timing: Negotiable |
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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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Building Area Building Area: 3153 Square Feet |
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Community Features: Basketball Court, Lake, Library, Medical Facilities, Park, Playground, Public Rec Facilities |
Other Playground |
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No HOA |
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Lot Area: 6.26 Acres |
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BasementMls Number: 24038493Attic: NoneAbove Grade Unfinished Area: 3153 |
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Basketball CourtLakeLibraryMedical FacilitiesParkPlaygroundPublic Rec Facilities |
Last check for updates: about 18 hours ago
Listed by Susan A. Malan, (617) 645-4392
William Pitt Sotheby's Int'l, (860) 767-7488
Bought with: Matt DeLucia, (860) 966-1617, William Pitt Sotheby's Int'l, (860) 777-1800
Source: Smart MLS, MLS#24038493
Price History for 96 Middlesex Avenue
| Date | Price | Event | Source |
|---|---|---|---|
| 01/31/2025 | $1,300,000 | Sold | Smart MLS #24038493 |
| 01/24/2025 | $1,375,000 | Pending | Smart MLS #24038493 |
| 12/11/2024 | $1,375,000 | PriceChange | Smart MLS #24038493 |
| 08/14/2024 | $1,395,000 | Listed For Sale | Smart MLS #24038493 |
| 04/12/2022 | $460,000 | Sold | Smart MLS #170342243 |
| 01/08/2021 | $498,000 | Contingent | Smart MLS #170342243 |
| 11/09/2020 | $498,000 | Pending | Agent Provided |
| 12/23/2019 | $498,000 | Listed For Sale | Agent Provided |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $10,953 |
| Assessment | $404,460 |
Home facts updated by county records
Comparable Sales for 96 Middlesex Avenue
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.17 | Single-Family Home | $975,000 | 11/17/25 | 4 | 2.5 | 3,149 | |
0.57 | Single-Family Home | $1,000,050 | 06/25/25 | 4 | 3 | 3,054 | |
0.78 | Single-Family Home | $952,397 | 07/10/25 | 3 | 3 | 3,788 | |
0.94 | Single-Family Home | $1,275,000 | 12/12/25 | 3 | 3 | 2,664 | |
0.44 | Single-Family Home | $635,000 | 04/30/26 | 3 | 3 | 2,752 | |
0.52 | Single-Family Home | $750,000 | 02/20/26 | 3 | 2.5 | 2,888 | |
0.67 | Single-Family Home | $1,135,000 | 06/30/25 | 4 | 4.5 | 3,351 | |
0.55 | Single-Family Home | $810,000 | 11/14/25 | 3 | 3.5 | 2,322 | |
0.28 | Single-Family Home | $530,000 | 02/26/26 | 3 | 2.5 | 1,664 |
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Assigned Schools
These are the assigned schools for 96 Middlesex Avenue.
- John Winthrop Middle School
- 7-8
- Public
- 238 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
- 489 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
- 222 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 96 Middlesex Avenue.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
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Off Market Homes Near 96 Middlesex Avenue
- SOLDMAY 22, 2026Coldwell Banker Realty
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SOLDMAY 14, 2026William Pitt Sotheby's Int'l- SOLDAPR 30, 2026Century 21 AllPoints Realty
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Homes for rent near 96 Middlesex Avenue
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96 Middlesex Avenue, Chester, CT 06412 is a 4 bedroom, 4 bathroom, 3,153 sqft single-family home built in 1830. 96 Middlesex Avenue is located in Chester Center, Chester. This property is not currently available for sale. 96 Middlesex Avenue was last sold on Jan 31, 2025 for $1,300,000 (5% lower than the asking price of $1,375,000). The current Trulia Estimate for 96 Middlesex Avenue is $1,387,800.