11

Chester, CT Houses for Sale

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  • 131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    /27

    $649,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    131 Middlesex Ave, Chester, CT 06412

    Discover this waterfront delight in charming Chester, sure to reward you with year-round views! Completely and thoughtfully renovated in 2012 from the ground up, this pristine Colonial offers 3 floors of living space and a smart L-shape open floor plan ensuring that you always have a gorgeous view. In addition to some hardworking first floor spaces (roomy mudroom, full bath and laundry room), the

    Agent Photo

    Claudia O'Connell

    William Raveis Real Estate

    (860) 590-3562

    131 Middlesex Ave, Chester, CT 06412
  • 16 Hickory Hill Dr, Chester, CT 06412
    16 Hickory Hill Dr, Chester, CT 06412
    16 Hickory Hill Dr, Chester, CT 06412
    /40

    $785,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    16 Hickory Hill Dr, Chester, CT 06412

    Welcome to this well maintained 3 Bedroom Cape in the charming town of Chester, just a short distance from downtown. The first floor of this home has an upscaled eat-in kitchen with newer appliances, breakfast bar and granite countertops, a Living/Dining room running front to back, an Office with built-in custom bookshelves and file drawers and a large (17 X 14), inviting Family Room with Propane

    Suzanne McConville William Raveis Real Estate

    16 Hickory Hill Dr, Chester, CT 06412
  • 6 Spring St, Chester, CT 06412
    6 Spring St, Chester, CT 06412
    6 Spring St, Chester, CT 06412
    /40

    $790,000

    • 2 Beds
    • 3 Baths
    • 1,598 Sq Ft

    6 Spring St, Chester, CT 06412

    Welcome to 6 Spring Street, a residence that transcends the ordinary. Known affectionately as "The Recycle House," this home is a testament to over a decade of meticulous craftsmanship, with the majority of its structure composed of upcycled materials. Its acclaim extends beyond its eco-friendly design, having been rated as one of the top 70 Airbnbs near NYC by the online magazine "Curbed" and

    Amy Graham William Pitt Sotheby's Int'l

    6 Spring St, Chester, CT 06412
  • 28 Hoop Pole Hill Rd, Chester, CT 06412
    28 Hoop Pole Hill Rd, Chester, CT 06412
    28 Hoop Pole Hill Rd, Chester, CT 06412
    /39

    $774,000

    • 4 Beds
    • 3.5 Baths
    • 3,396 Sq Ft

    28 Hoop Pole Hill Rd, Chester, CT 06412

    Discover the perfect blend of elegance and convenience in this custom Cape Cod home, nestled privately in Chester, CT. Boasting 4 bedrooms and 3.5 baths, this residence is convenient to the vibrant downtown area and easily accessible to the highway, yet set in a quiet woodland sanctuary, directly across from over 100 acres of state forest and trails. With timeless decor that exudes classic charm,

    Teri Strain-Lewis William Pitt Sotheby's Int'l

    28 Hoop Pole Hill Rd, 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
  • 8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    /40

    $775,000

    • 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
  • 288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    /40

    $3,375,000

    • 4 Beds
    • 6 Baths
    • 4,926 Sq Ft

    288 Middlesex Ave, Chester, CT 06412

    East View is a long-admired Connecticut Riverfront property, a rare offering that perfectly marries historic provenance with elevated modern living. The circa 1800 home was masterfully renovated and expanded in 2010 with an architect's eye and a reverence for its storied past. Meticulous attention to detail is found in the extensive millwork, custom built-ins and hand-hewn beams lending warmth

    Nancy Mesham Coldwell Banker Realty

    288 Middlesex Ave, Chester, CT 06412
  • 50 Bokum Rd, Chester, CT 06412
    50 Bokum Rd, Chester, CT 06412
    50 Bokum Rd, Chester, CT 06412
    /31

    $425,000

    • 2 Beds
    • 1.5 Baths
    • 807 Sq Ft

    50 Bokum Rd, Chester, CT 06412

    Welcome to this delightful 2-bedroom, 1.5 bath home tucked in the heart of historic Chester, CT. Brimming with character, this cozy home blends modern updates with small-town New England charm. Step inside to find a bright and inviting living space, an updated kitchen, and thoughtful touches throughout. Perfectly sized for easy living, the property offers a low-maintenance yard ideal for

    Cynthia Sigurdson William Pitt Sotheby's Int'l

    50 Bokum Rd, Chester, CT 06412
  • 13 Cross Rd, Chester, CT 06412
    13 Cross Rd, Chester, CT 06412
    13 Cross Rd, Chester, CT 06412
    /40

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,324 Sq Ft

    13 Cross Rd, Chester, CT 06412

    Set on a private 4.48-acre rear lot, this inviting Colonial offers over 2,300 sq. ft. of comfortable living space with 8 spacious rooms, including 3 bedrooms. The welcoming family room features a fireplace, built-ins, soaring cathedral ceilings, a large skylight, and sliders leading to the rear deck, filling the home with natural light. Enjoy the tranquility and privacy of the setting while still

    Curtiss Clemens Jr. Century 21 Clemens Group

    13 Cross Rd, Chester, CT 06412
  • 28 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    /40

    $625,000

    • 2 Beds
    • 3 Baths
    • 3,091 Sq Ft

    28 S Wig Hill Rd, Chester, CT 06412

    Step into history with this 1770 Cape, part of "Old Homes of Chester." Nestled on beautiful grounds featuring rolling hills, gardens, and stunning stone walls, the property abuts 8 acres of serene land trust, offering unparalleled privacy and a park-like setting. The main house spans 1303 square feet and includes 2 bedrooms and 2 full baths. Recent upgrades include a new furnace (2023), electric

    Andrew O'Reilly Seaport Real Estate Services

    28 S Wig Hill 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
Connecticut Middlesex County Chester

Houses for Sale in Chester, CT

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 48 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, CT over the last 12 months is $537,000, up 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$537,000
Median Single Family Sale Price
$578,500
Average Price Per Sq Ft
$323
Number of Homes for Sale
10
Last 12 months Home Sales
41
Months of Supply
2.90
Median List Price
$635,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
19%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 11 houses for sale, offering an array of options for potential buyers. With houses priced between $425,000 to $3,375,000, there's a range to accomodate every budget. As of September, 2025 the median home price in Chester is $635,000, while the average sale price is $661,701, offering insights into the local housing market. On average, houses spend 48 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.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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