Chester is situated alongside the Connecticut River, offering a tranquil country lifestyle and picturesque water vistas. Additionally, the town boasts a distinctive feature known as the Chester-Hadlyme Ferry. It is one of the few remaining operational ferries on the Connecticut River and provides an enjoyable means of transportation to Hadlyme. It contributes to the pervasive feeling of historical significance that permeates Chester, particularly in the downtown area. “Chester is smaller than most towns, like nearby Mystic, but it has a secluded charm,” says Lewis Jump III of ReMax ONE. “It has a lot of older Victorian, Cape Cods and colonials.”
Chester
Located in Middlesex County
Lots of National Register of Historic Places structures
Do not overlook Chester's downtown area, which has charming and distinctive architecture. This pedestrian-friendly region boasts a few structures that are listed on the National Register of Historic Places, making it a charming destination for a leisurely afternoon. Craig Milton, a Broker with Re/Max Valley Shore, describes Chester's downtown as having a charming and well-preserved historic ambiance. One recommended eatery is River Tavern. It is a well-liked establishment that serves wine, beer and high-quality delicacies such as handmade tagliarini. Locals also enjoy the seafood fare at Fresh Salt and the peanut butter and jelly stuffed French toast at Whistle Stop. “One advantage of living in Chester is walking to the local shops and restaurants on Main Street,” adds Jump III.
The starting price for homes in Chester is approximately $227,000. These homes typically include three bedrooms, one bathroom, and a living space of 1,500 square feet. Additionally, they are situated on almost 2,000 square feet of land. The highest quality residences reach a maximum price of $2 million for a spacious home featuring five bedrooms, three bathrooms and more than 1.5 acres of land. “The pricing is just right,” says Jump III, “Some of the homes are as old as 60 to 70 years old.” Those who do not care for HOAs are in luck — there aren’t any in Chester. Chester’s rural region, part of the tri-town area encompassing Essex and neighboring Deep River, is characterized by its expansive lot sizes and proximity to the Connecticut River. The CAP Index crime score for the area is 2 out of 10, which is lower than the national average of 4.
Well-rated schools
According to Niche, students in Chester are enrolled in Regional School District 4, which is regarded as the fourth-best school district in Middlesex County. The district has received an A-minus grade and has excellent reviews for its academic programs, teaching staff, extracurricular organizations and activities, and college preparation. Students commence their educational voyage at Chester Elementary School, which holds the second position among primary schools in Middlesex County according to Niche rankings. The school possesses an A rating. John Winthrop Middle School has received a B rating from Niche. Valley Regional High School, graded a B-plus by Niche, is renowned for its exceptional professors, diverse range of clubs and activities, and rigorous academic programs. All schools within this district have been recognized among the top 10 educational institutions in Middlesex County by Niche. There are also seven local colleges and universities nearby, including Mitchell College.
Reservoir edge parks
Visit the Pattaconk Recreation area to experience a breath of fresh air. The area consists of a combination of woodland and open grassland. Visitors can explore the forested area and enjoy a leisurely walk amidst the trees or relax in a gently sloping grassy field leading to the Pattaconk Reservoir's edge. Many visitors recline on a floatation device, relax on the water, arrange a blanket and picnic with friends and family.
Lots of dining choices
Do not overlook Chester's downtown area, which has charming and distinctive architecture. This pedestrian-friendly region boasts a few structures that are listed on the National Register of Historic Places, making it a charming destination for a leisurely afternoon. Craig Milton, a Broker with Re/Max Valley Shore, describes Chester's downtown as having a charming and well-preserved historic ambiance. One recommended eatery is River Tavern. It is a well-liked establishment that serves wine, beer and high-quality delicacies such as handmade tagliarini. Locals also enjoy the seafood fare at Fresh Salt and the peanut butter and jelly stuffed French toast at Whistle Stop. “One advantage of living in Chester is walking to the local shops and restaurants on Main Street,” adds Jump III.
Catch the ferry
In addition to the ferry, Chester possesses another means of transportation that is not commonly found in rural New England towns – its own airport. For long-distance travelers, the Tweed/New Haven Airport is less than an hour from the area. In addition to the ferry and the airport, the most efficient mode of transportation is by automobile. Route 9 is the main thoroughfare in Chester. There are also two CTtransit bus stops in the neighborhood.
Low crime score
The CAP Index crime score for the area is 2 out of 10, which is lower than the national average of 4.
Photography Contributed By
Fabio Riso
Video By
Mark Tilley
Interested in learning more about homes in this area? Reach out to , an experienced agent in this area.
Agents Specializing in this Area
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Jennifer D'Amato
Jennifer D'Amato
Real Broker CT, LLC
(475) 224-4727
143 Total Sales
2 in Chester
$300K - $375K Price Range
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Kelly Puorro
Kelly Puorro
Puorro Realty Group
(959) 265-4615
93 Total Sales
9 in Chester
$150K - $900K Price Range
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Brandon Puorro
Brandon Puorro
Puorro Realty Group
(860) 661-0562
46 Total Sales
9 in Chester
$150K - $640K Price Range
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Dylan Walter
Dylan Walter
William Raveis Real Estate
(959) 265-0588
79 Total Sales
1 in Chester
$451,000 Price
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Amy Rio
Amy Rio
Executive Real Estate Inc.
(860) 321-8567
1,240 Total Sales
1 in Chester
$295,000 Price
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Kimberly McHugh
Kimberly McHugh
Puorro Realty Group
(857) 323-9161
6 Total Sales
2 in Chester
$368K - $405K Price Range
Schools
Source:
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
- K to 6th
- Public
- 6th to 8th
- Public
- 9th to 12th
- Public
Chester Housing Trends
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 $537,000, up 25% from the median home sale price over the previous 12 months.
Housing Trends
Median List Price
$605,900
Median Sale Price
$537,000
Median Single Family Sale Price
$562,000
Median Change From 1st List Price
0%
Last 12 months Home Sales
43
Median Home Sale Price YoY Change
25%
Average Price Per Sq Ft
$311
Neighborhood Facts
Number of Homes for Sale
6
Months of Supply
1.70
Open Houses
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Sunday, Jul 1311am - 2pm
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Sunday, Jul 131 - 3pm
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Saturday, Jul 121 - 3pm
Homes for Sale
Homes for Rent
Distribution of Home Values
Average Home Value
Property Mix - Square Feet
Weather
Annual Precipitation
51''
Average Winter Low Temperature
21°F
Average Summer High Temperature
84°F
Annual Snowfall
35''
Area Factors
Somewhat Bikeable
Bike Score®
13
/ 100
Car-Dependent
Walk Score®
0
/ 100
Source: Walk Score
Source: Walk Score
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
