Chester, CT Houses for Sale

/2
$282,225
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
3 Kirtland Ave, Chester, CT 06412

REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 1974, this one level home offers approximately 1344 finished square feet, two bedrooms and two full baths, fireplace, unfinished basement and attached one car garage. This home sits on an approximate 14810 sqft lot. "As is" cash only sale with no contingencies or inspections.

Sherry Price Realhome Services & Solutions

3 Kirtland Ave, Chester, CT 06412
Explore Chester
/34
$525,000
- 3 Beds
- 2 Baths
- 1,188 Sq Ft
135 Middlesex Ave, Chester, CT 06412

Coming in a few short days.... This WATERFRONT home on Chester Cove has the most spectacular views! Steps to fishing or kayaking! Enjoy watching the wildlife from the 20x10 deck just off the kitchen/dining/living rooms. Wonderful light enters through the numerous windows on the first floor with its open floor plan, full bath and sliders to the deck. On the second floor there are three bedrooms

Lisa Genovali Re/Max Valley Shore

135 Middlesex Ave, Chester, CT 06412
/38
$3,150,000
- 4 Beds
- 6 Baths
- 4,926 Sq Ft
288 Middlesex Ave, Chester, CT 06412

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

Nancy Mesham Coldwell Banker Realty

288 Middlesex Ave, Chester, CT 06412

Connecticut Middlesex County Chester

Why Live in Chester

Chester, Connecticut, offers a serene lifestyle along the Connecticut River, characterized by its historical charm and picturesque views. The Chester-Hadlyme Ferry, one of the few operational ferries on the river, adds to the town's historical ambiance, especially in the downtown area, which features structures listed on the National Register of Historic Places. Chester's downtown is pedestrian-friendly, with unique architecture and a variety of dining options, such as River Tavern and Whistle Stop, making it a delightful spot for a leisurely afternoon. The town is known for its older Victorian, Cape Cod, and colonial homes, with expansive lot sizes and no homeowners associations. Chester is part of the tri-town area, including Essex and Deep River, and boasts a crime rate lower than the national average. Educational opportunities are strong, with Regional School District 4 and Chester Elementary School receiving high ratings for their academic programs and extracurricular activities. For outdoor enthusiasts, the Pattaconk Recreation Area offers woodland and grassland spaces leading to the reservoir's edge, perfect for picnics and relaxation. Chester is conveniently located near Tweed/New Haven Airport, less than an hour away, and is accessible via Route 9 and CTtransit bus stops, providing efficient transportation options.

Learn more about living in Chester

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 62 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 22% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$610,000

Median Single Family Sale Price

$610,000

Average Price Per Sq Ft

$345

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

0.90

Median List Price

$649,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

22%

How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 3 houses for sale, offering an array of options for potential buyers. With houses priced between $282,225 to $3,150,000, there's a range to accomodate every budget. As of May, 2026 the median home price in Chester is $649,000, while the average sale price is $691,884, offering insights into the local housing market. On average, houses spend 62 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chester, CT and find the perfect place to call home.

Single-family Homes for Sale in Nearby Cities

Single-family Homes for Sale in Nearby Counties

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