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Chester, CT Homes for Sale

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  • 43 N Main St, Chester, CT 06412
    43 N Main St, Chester, CT 06412
    43 N Main St, Chester, CT 06412
    /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
  • 7 Hazen St, Chester, CT 06412
    7 Hazen St, Chester, CT 06412
    7 Hazen St, Chester, CT 06412
    /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
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, 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
  • 7 Old Depot Rd, Chester, CT 06412
    7 Old Depot Rd, Chester, CT 06412
    7 Old Depot 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
  • 11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    /10

    $232,500

    • Land
    • 1.50 Acres
    • $155,000 per Acre

    11 Kings Hwy, Chester, CT 06412

    1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line

    Rachel Welch William Raveis Real Estate

    11 Kings Hwy, Chester, CT 06412
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    /2

    $985,000

    • Land
    • 34 Acres
    • $28,996 per Acre

    88 Winthrop Rd, Chester, CT 06412

    The wooded 33.97 acre site has extensive open water views with frontage on Winthrop Road (Rt 145) and Butter Jones Road. The property abuts Deep River and Killingworth with convenient access to charming shopping areas. Also, the Chester Airport is within walking distance. A long driveway winds through the spacious, park-like setting, ideal for a planned unit development.

    Peter Walsh Re/Max Valley Shore

    88 Winthrop Rd, Chester, CT 06412
  • 8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    /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

Real Estate & Homes for Sale in Chester, CT

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

Frequently Asked Questions

What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $685,773.
How many homes have sold over the last 12 months in Chester, CT?
41 homes have sold in Chester, CT over the last 12 months.
What are the most popular zip codes in Chester, CT?
The most popular zip codes in Chester, CT include 06457, 06437, 06443, 06405 and 06492.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $525,000. If you put a 20% down payment of $105,000 and had a 30-year fixed mortgage with an interest rate of 6.67%, your estimated principal and interest payment would be $2,700 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 $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
$537,000
Average Price Per Sq Ft
$307
Number of Homes for Sale
4
Last 12 months Home Sales
41
Months of Supply
1.20
Median List Price
$525,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
22%
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