$579,202Average Value$345Average Price per Sq Ft6Homes For Sale
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.”
The Villager serves American cuisine in Chester.
Chester Public Library provides educational resources.
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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.
Colonial homes are a staple of Chester real estate.
Chester real estate includes Four Square style homes.
Chester has many buildings listed on the National Register of Historic Places.
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Highly 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 can 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 holds an A rating. John Winthrop Middle School has received a B rating and Valley Regional High School, graded a B-plus by Niche, is renowned for its exceptional teachers, 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.
Chester Elementary School holds an A rating from Niche.
John Winthrop Middle School holds a B rating from Niche.
Valley Regional High School serves the Chester community.
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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.
Outdoor enthusiasts utilize trails at Pattaconk Recreation Area.
North Quarter Park offers outdoor recreation in Chester.
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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.
Retail businesses line the streets of downtown Chester.
Downtown Chester serves as a community hub.
River Tavern offers a selection of dishes in Chester.
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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.
Chester features a landscape of streams and lakes.
Properties in Chester benefit from a riverfront location.
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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.
Residents dine outdoors at restaurants in Chester.
Chester is a residential community in the tri-state area.
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Photography Contributed By
Fabio Riso
Video By
Francisco de la Vera
Interested in learning more about homes in this area?
Reach out to
Dylan Walter,
an experienced agent in this area.
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.
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On average, homes in Chester, CT sell after 65 days on the market compared to the national average of 57 days. The median sale price for homes in Chester, CT over the last 12 months is $610,000, up 14% from the median home sale price over the previous 12 months.
A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American
Rare waterfront opportunity! Nestled directly on the water, 90 Water St is a 1-bathroom Ranch currently configured as a 1-bedroom, but offering a spacious layout that easily converts to a 2-bedroom home. Built in 1950, the property provides a fantastic foundational footprint. It features a large 13'6" x 20'10" living room and a versatile 10'3" x 20'10" family room-the ideal space to partition
Welcome to 92 Water St, a charming 1927 two-story Colonial offering a rare opportunity to own waterfront property in picturesque Chester, CT! This 3-bedroom, 1-bathroom home is perfectly situated right on the water, offering tranquil riverfront views and an unbeatable location just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining.
Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and
Discover the perfect setting to build your dream home in the desirable Wig Hill area of Chester, Connecticut. Located near Cockaponset Sate Forest and the scenic Connecticut River valley. This beautiful one-acre level building lot features approximately 211 feet of road frontage and dimensions of roughly 200 x 200 feet, offering ample space and flexibility to bring your custom plans and ideas to
A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor.
Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and
One floor living in this well maintained Ranch. 1 Full Bath & One 1/2 Bathroom. Hardwood floors. Fireplace in Living Room. Large Eat-in kitchen with Stainless Steel appliances. Recent upgrades include: New HVAC, New 200 AMP electric panel, new roof, new pellet stove, and remodeled bathroom. Open and level yard with nice plantings. Solar system recently installed to assure reasonable utility
NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want
Nestled in the charming town of Deep River, between the villages of Essex and Chester, this beautiful Colonial offers the perfect blend of classic character and modern updates. Featuring 4 bedrooms, 2 full baths and 2 half baths, this spacious home is designed for comfortable living and entertaining. Enter through the welcoming foyer, where the dining room sits to the left, while French doors
AVAILABLE OCTOBER 2026: Recently renovated unit of a 2 family house in Chester CT. This 850 sq ft living space is heated by propane, has a flexible floor plan, in-unit laundry, new kitchen area floor & new fridge. 2 private entrances and outdoor space with small fire pit. Perfect for a solo renter or couple. WALK TO TOWN - just 8/10 mile to lovely downtown Chester. This charming, quaint town
Private 1 bedroom apartment in rear of Victorian estate property. Completely remodeled everything is new and utilities are included. Flexible on length of stay. No smoking, no pets please. Washer/dryer hookups are included. Arrange visit by appointment.
Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its bustling restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an
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