38 Middlesex Ave, Chester, CT 06412
Property image
Property image
OFF MARKET

$434,600

Trulia Estimate
  • 2 Beds
  • 1.5 Baths
  • 1,140 sqft (on 1.32 acres)

38 Middlesex Ave, Chester, CT 06412

Chester Center
Est. Refi. Payment $3,062/mo*
Refinance Your Home
Currently Off Market - Sold Dec 3, 2019 for $285,000

Home Value

Trulia Estimate
$435K
Since last month
Decreased$5K (-1.1%)
Since last year
Increased$23K (+5.5%)
Since last sale
Increased$149K (+52.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +135% in the last 10 years
MonthEstimated value
2026
September 2026$434K
August 2026$435K
July 2026$439K
June 2026$451K
May 2026$446K
April 2026$432K
March 2026$426K
February 2026$405K
January 2026$406K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
79 Middlesex Avenue, Chester, CT
0.31
Single-Family Home
$410,000
04/30/26
2
1
1,470
23 Spring Street, Chester, CT
0.59
Single-Family Home
$550,000
10/15/25
2
1.5
1,104
5 Mitchell Lane, Deep River, CT
0.35
Single-Family Home
$366,000
12/29/25
2
1.5
1,081
61 Maple St, Chester, CT
0.46
Single-Family Home
$140,000
07/13/26
2
1
672
21 East Liberty Street, Chester, CT
0.60
Single-Family Home
$252,500
11/17/25
2
1
1,012
23 Hickory Hill Dr, Chester, CT
0.25
Single-Family Home
$446,000
10/23/25
3
3
1,876
16 Hickory Hill Drive, Chester, CT
0.27
Single-Family Home
$755,000
11/19/25
3
2.5
1,896
72 Winter Avenue, Deep River, CT
0.32
Single-Family Home
$320,000
08/26/26
3
3
1,836
7 Hickory Hill Drive, Chester, CT
0.33
Single-Family Home
$549,000
03/24/26
3
2.5
2,202
54 Maple St, Chester, CT
0.57
Single-Family Home
$325,000
11/26/25
3
2
1,260

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
30 Middlesex Avenue, Chester, CT 06412
0.05
$420,900
2
1.5
1,362
Off Market
26 Middlesex Avenue, Chester, CT 06412
0.09
$481,400
4
1.5
1,496
Off Market
9 Gilbert Hill Road, Chester, CT 06412
0.15
$465,100
2
1.5
2,008
Off Market
142 Main Street, Chester, CT 06412
0.16
$729,000
3
2
2,188
Off Market
16 Middlesex Avenue, Chester, CT 06412
0.17
$561,600
3
2
1,963
Off Market
15 Gilbert Hill Road, Chester, CT 06412
0.17
$1,083,500
4
3
3,054
Off Market
137 Main Street, Chester, CT 06412
0.20
$656,200
3
1.5
1,570
Off Market
19 Hickory Hill Drive, Chester, CT 06412
0.23
$838,300
3
3
2,646
Off Market
7 Old Depot Road, Chester, CT 06412
0.24
$975,000
4
2.5
3,149
Recently Sold
25 Gilbert Hill Road, Chester, CT 06412
0.27
$1,229,100
4
4.5
3,351
Off Market
16 Hickory Hill Drive, Chester, CT 06412
0.27
$755,000
3
2.5
1,896
Recently Sold
18 Hickory Hill Drive, Chester, CT 06412
0.28
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Off Market

Local Information

  • Map ViewExplore the area around 38 Middlesex Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1890
1.32 acre lot
1,140 sqft
$381/sqft

About this House

Loaded with charm and character this "move in ready" farmhouse has everything you have been looking for in the perfect home. While honoring the homes historic style (c.1890) the recent renovations allow for modern conveniences....designed for the way we live today. The new, well appointed kitchen with custom cabinets, stainless appliances and granite counters opens to a welcoming porch overlooking park-like grounds. A cozy dining area and the light filled living room with new built-ins is great space for casual everyday living. At the top of the stairs you'll find an ideal spot for a small in-home office, the master bedroom and a guest room...both with expanded closet space. A beautifully designed bath features a tiled walk-in-shower and a Jacuzzi tub. The private stone terrace with a lovely perennial garden is the perfect place for outdoor entertaining and the new Kloter Farms shed is ideal for all of your gardening needs. You will have peace of mind with the updated mechanical's including a new hot water heater, oil tank, new wiring and 200 amp electrical service. Other recent improvements include a new roof, sheetrock, insulation, all new windows and moldings. There are gleaming hardwood floors throughout. Located just a short walk to the Village the house is prominently set on 1.32 acres and is bordered by stone walls, mature plantings and a new privacy fence. Whether you are looking for a full time or residence or a weekend retreat this property is the perfect place to call home.
38 Middlesex Ave, Chester, CT 06412 is a 2 bedroom, 2 bathroom, 1,140 sqft single-family home in Chester Center, built in 1890. It last sold for $285,000 on Dec 3, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $434,600, with a rent estimate of $2,641/month.

Home Details for 38 Middlesex Ave

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherRefrigerator
Security
Security System

Exterior Features

Exterior Home Features
Roof: OtherExterior: Stone, VinylGardenPatioPorch
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1890Year Updated: 1991
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.32 acres

Price and Tax history

DateEventPrice
Dec 3, 2019
Source: Smart MLS #170240285
Sold
$285,000
Oct 11, 2019
Source: Agent Provided
Pending
$285,000
Oct 2, 2019
Source: Agent Provided
Listed For Sale
$285,000
Jun 21, 2017
Source: Agent Provided
ListingRemoved
$274,900
Mar 16, 2017
Source: Agent Provided
Listed For Sale
$274,900

Market trends in Chester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
3MoM

Around this home

Neighborhood Overview

Chester Center
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Frequently asked questions about 38 Middlesex Ave

  • What is 38 Middlesex Ave estimated to be worth?
    Trulia's estimated value for 38 Middlesex Ave in Chester, CT is $434,600.
  • What is the price history for 38 Middlesex Ave?
    38 Middlesex Ave in Chester, CT last sold for $285,000 in December 2019.
  • Is Chester a buyer's or seller's market?
    Chester is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 38 Middlesex Ave?
    The closest schools to 38 Middlesex Ave in Chester, CT are Chester Elementary School (Pre-K, rated 7/10), John Winthrop Middle School (rated 4/10), Valley Regional High School (rated 7/10).
  • How big is the lot at 38 Middlesex Ave?
    The lot at 38 Middlesex Ave in Chester, CT is about 1.3 acres.
  • Does 38 Middlesex Ave have parking?
    Yes, 38 Middlesex Ave in Chester, CT has on-site parking.

Apartments for Rent

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Off Market Homes Near 38 Middlesex Ave

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