6
Chester, CT Homes for Sale
-
-
$985,000
- 2 Beds
- 2.5 Baths
- 2,240 Sq Ft
88 Winthrop Rd, Chester, CT 06412
88 Winthrop Rd, Chester, CT 06412 -
$1,150,000
- 4 Beds
- 2.5 Baths
- 3,149 Sq Ft
7 Old Depot Rd, Chester, CT 06412
7 Old Depot Rd, Chester, CT 06412 -
$232,500
- Land
- 1.50 Acres
- $155,000 per Acre
11 Kings Hwy, Chester, CT 06412
11 Kings Hwy, Chester, CT 06412 -
$985,000
- Land
- 34 Acres
- $28,996 per Acre
88 Winthrop Rd, Chester, CT 06412
88 Winthrop Rd, Chester, CT 06412 -
$825,000 Open Sat 11AM - 1PM
- 4 Beds
- 3 Baths
- 3,864 Sq Ft
8 Route 148, Killingworth, CT 06419
8 Route 148, Killingworth, CT 06419
Why Live in Chester



Chester, nestled along the Connecticut River, provides a serene country lifestyle with scenic water views. The Chester-Hadlyme Ferry, one of the few operational ferries on the river, adds to the town's historical charm, particularly in its pedestrian-friendly downtown area, which features buildings listed on the National Register of Historic Places. Chester's downtown is known for its well-preserved historic ambiance and local attractions, including the popular River Tavern, Fresh Salt, and Whistle Stop. The neighborhood experiences distinct seasonal weather, enhancing its picturesque setting. Homes in Chester range from older Victorian, Cape Cod, and colonial styles, with properties spanning from three-bedroom houses on nearly 2,000 square feet of land to larger estates on over 1.5 acres. The area is part of the tri-town region, including Essex and Deep River, known for its expansive lot sizes and proximity to the Connecticut River. Chester's crime rate is lower than the national average, contributing to its appeal. Students attend highly rated schools in Regional School District 4, including Chester Elementary School and Valley Regional High School, both recognized for their strong academic programs. Outdoor enthusiasts can visit the Pattaconk Recreation Area, which offers woodland trails and access to the Pattaconk Reservoir. Unique transportation options include the Chester-Hadlyme Ferry and a local airport, with Route 9 serving as the main thoroughfare. Chester's combination of historical charm, natural beauty, and practical amenities makes it a distinctive neighborhood within the tri-town area.
What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $684,783.
How many homes have sold over the last 12 months in Chester, CT?
40 homes have sold in Chester, CT over the last 12 months.
What are the most popular zip codes in Chester, CT?
How much do you need to make to afford a house in Chester?
The median home price in Chester is $522,000. If you put a 20% down payment of $104,400 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $2,710 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $116K a year to afford the median home price in Chester.
How are the schools in Chester, CT?
Chester, CT has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Lyme-Old Lyme High School, Haddam-Killingworth High School and Lyme-Old Lyme Middle School. Browse all the schools in Chester, CT to learn more.
Home Trends in Chester, CT
On average, homes in Chester, CT sell after 49 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, CT over the last 12 months is $518,500, up 21% from the median home sale price over the previous 12 months.
Housing Trends
Median Sale Price
$518,500
Median Single Family Sale Price
$518,500
Average Price Per Sq Ft
$299
Number of Homes for Sale
2
Last 12 months Home Sales
40
Months of Supply
0.60
Median List Price
$522,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
21%
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