Chester, CT Houses for Sale

/40
$749,900 Open Sun 1PM - 3PM
- 3 Beds
- 1.5 Baths
- 1,538 Sq Ft
43 N Main St, Chester, CT 06412

Fantastic home in wonderful private setting with views of Chester Creek and sounds of the waterfall across the street. Calling all artists, authors, creatives. This is the perfect space to create, dream, let your imagination bloom. Beautiful farm porch, detached two car garage, the "glass house" at the edge of Chester Creek to relax and watch nature. 3 bedrooms, 1 1/2 baths, beautiful propane

Susan Malan William Pitt Sotheby's Int'l

43 N Main St, Chester, CT 06412
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/21
$189,000
- 2 Beds
- 1 Bath
- 480 Sq Ft
7 Hazen St, Chester, CT 06412

Back on Market, seller could not get financing....CASH SALE ONLY. Seasonal home in Cedar Lake community and easily converted to year round home. Great space with enclosed porch to enjoy lake views. Update living room, kitchen, 1st floor bedroom and finish off bunk room upstairs for year round living. Corner lot with large usable backyard and shed. This is an Estate sale and will be sold as-is.

Judy Halleran RE/MAX on the Bay

7 Hazen St, Chester, CT 06412
/4
$985,000
- 2 Beds
- 2.5 Baths
- 2,240 Sq Ft
88 Winthrop Rd, Chester, CT 06412

The charming 3 bedroom colonial with a large attached garage and 2 outbuildings overlooks a lovely 5 acre pond. The home features a large kitchen and 2 1/2 baths with laundry on the second floor. Highlighting the living room is a 30 ft. Cathedral ceiling. Master bedroom includes an interior balcony, overlooking the living area. Generous windows and sliders afford beautiful open views of the

Peter Walsh Re/Max Valley Shore

88 Winthrop Rd, Chester, CT 06412
/40
$1,150,000
- 4 Beds
- 2.5 Baths
- 3,149 Sq Ft
7 Old Depot Rd, Chester, CT 06412

Bella Vista: A Timeless Italianate Treasure on 6 Acres. Step into a piece of history, a magnificent Italianate country villa that has graced the landscape since 1908. First time on the market, this storied estate has been lovingly preserved by the same family for generations, a testament to its enduring allure. Listed on the National Registry of Historic Places, Bella Vista is an architectural

Colette Harron William Pitt Sotheby's Int'l

7 Old Depot Rd, Chester, CT 06412
/40
$825,000
- 4 Beds
- 3 Baths
- 3,864 Sq Ft
8 Route 148, Killingworth, CT 06419

Tucked away in complete privacy, this stunning post and beam home offers a rare opportunity to live in harmony with nature. Situated on 6.4 acres of wooded serenity, the property is a true retreat and offers many outside features including a tranquil pond, ample space for gardens, hobbies, or simply room to roam. The home itself showcases timeless craftsmanship with exposed beams, soaring

Kara Bell J.M. REALTY

8 Route 148, Killingworth, CT 06419

Connecticut Chester

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.

Learn more about living in Chester

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 $537,000, up 22% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$537,000

Median Single Family Sale Price

$518,500

Average Price Per Sq Ft

$303

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

0.90

Median List Price

$522,000

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 5 houses for sale, offering an array of options for potential buyers. With houses priced between $189,000 to $1,150,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $522,000, while the average sale price is $665,374, offering insights into the local housing market. On average, houses spend 49 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.

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