Welcome to 108 Middlesex Ave. A multi family Colonial income producing property in the heart of Chester! The home was built in 2002, and in 2006 an attached accessory dwelling unit / inlaw apartment was added and is now occupied at $2,000 a month. The main house features a bright and inviting layout with hardwood floors, a cozy fireplace in the living room and sliders from the dining room out to the deck. A well-appointed kitchen has a pantry, granite countertops, stainless steel appliances, a custom wine rack and tile floor. There is also a nice half bath on this main level. Upstairs, the primary suite boasts a walk-in closet and a full bath, accompanied by two additional bedrooms and a full bathroom in the hallway. There is also a walk up storage attic and finished area. The lower level is mint and fully finished and walks out to the two car garage. The private rentable ADU has one bedroom, a full bathroom, living room dining combo, full kitchen, full laundry, nice walk up additional space and separate electric meter. Outside, enjoy the expansive backyard with a deck, an above-ground (heated??) pool, a shed with power for extra storage, and underground sprinklers. Additional highlights include EV charger, Generac generator (leased), and solar panels (owned). Located just minutes from Chester's vibrant town center, shopping, and dining, this home offers the perfect blend of comfort and convenience. Don't miss this incredible opportunity. Also listed under mls#24082679
Sold for $675,000 on 05/01/25
$675,000
108 Middlesex Avenue, Chester, CT 06412
4beds
4,056sqft
Single Family Residence
Built in 2002
0.74 Acres Lot
$688,600 Zestimate®
$166/sqft
$1,765 Estimated rent
Home value
$688,600
$627,000 - $757,000
$1,765/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: May 01, 2025 at 12:47pm
Listed by:
Trever R. Smith 860-876-7144,
Chiarito Real Estate LLC 860-227-2074,
Al Chiarito 860-227-2074,
Chiarito Real Estate LLC
Bought with:
Cortney Emshwiller-Swokla, RES.0773425
Coldwell Banker Realty
Source: Smart MLS,MLS#: 24076425
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 208 Square Feet
- Dimensions: 13 x 16
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 160 Square Feet
- Dimensions: 10 x 16
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 132 Square Feet
- Dimensions: 11 x 12
Bedroom
- Level: Main
- Area: 156 Square Feet
- Dimensions: 12 x 13
Dining room
- Features: Hardwood Floor
- Level: Main
- Area: 120 Square Feet
- Dimensions: 10 x 12
Family room
- Features: Laminate Floor
- Level: Lower
- Area: 276 Square Feet
- Dimensions: 12 x 23
Great room
- Features: Hardwood Floor
- Level: Upper
- Area: 384 Square Feet
- Dimensions: 16 x 24
Great room
- Features: Wall/Wall Carpet
- Level: Third,Upper
- Area: 272 Square Feet
- Dimensions: 16 x 17
Kitchen
- Features: Granite Counters, Eating Space, Pantry, Tile Floor
- Level: Main
- Area: 168 Square Feet
- Dimensions: 12 x 14
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 325 Square Feet
- Dimensions: 13 x 25
Heating
- Baseboard, Hot Water, Oil
Cooling
- Ductless
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Lower Level, Main Level
Features
- Wired for Data, In-Law Floorplan
- Windows: Thermopane Windows
- Basement: Full,Heated,Finished,Garage Access,Cooled,Liveable Space
- Attic: Storage,Finished,Walk-up
- Number of fireplaces: 1
Interior area
- Total structure area: 4,056
- Total interior livable area: 4,056 sqft
- Finished area above ground: 3,120
- Finished area below ground: 936
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Patio & porch: Deck
- Exterior features: Sidewalk, Rain Gutters, Lighting, Underground Sprinkler
- Has private pool: Yes
- Pool features: Above Ground
Lot
- Size: 0.74 Acres
- Features: Sloped
Details
- Additional structures: Shed(s)
- Parcel number: 2313457
- Zoning: R-5
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2002
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Underground Utilities
Green energy
- Energy efficient items: Windows
- Energy generation: Solar
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Library, Park, Playground, Shopping/Mall
Location
- Region: Chester
Price history
| Date | Event | Price |
|---|---|---|
| 5/1/2025 | Sold | $675,000-3.4%$166/sqft |
Source:  Smart MLS #24076425 | ||
| 4/29/2025 | Pending sale | $699,000$172/sqft |
Source: Smart MLS #24082679 | ||
| 2/25/2025 | Listed for sale | $699,000$172/sqft |
Source: Smart MLS #24076425 | ||
| 12/19/2024 | Listing removed | $3,900$1/sqft |
Source: Smart MLS #24055216 | ||
| 12/11/2024 | Listing removed | $699,000$172/sqft |
Source: Smart MLS #24040512 | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $11,880 +10.8% | $438,690 |
| 2024 | $10,726 +17.8% | $438,690 +43% |
| 2023 | $9,109 -0.1% | $306,710 -0.8% |
Find assessor info on the county website
Neighborhood: Chester Center
Nearby schools
GreatSchools rating
- 6/10Chester Elementary SchoolGrades: K-6Distance: 0.9 mi
- 3/10John Winthrop Middle SchoolGrades: 6-8Distance: 3 mi
- 7/10Valley Regional High SchoolGrades: 9-12Distance: 2.7 mi
Schools provided by the listing agent
- Elementary: Chester
- Middle: Region 4
- High: Valley
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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$688,600
2% more+ $13,772
With Zillow Showcase(estimated)
$702,372