10

Chester, CT Houses for Sale

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  • 25 Spring St, Chester, CT 06412
    25 Spring St, Chester, CT 06412
    25 Spring St, Chester, CT 06412
    /37

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft

    25 Spring St, Chester, CT 06412

    Tucked away on Spring Street in the heart of Chester village, this stately two-story residence gracefully combines classic farmhouse tradition with all the amenities of modern living. As you enter the home through the foyer, sunlight pours through generous windows, illuminating the living room anchored by an elegant fireplace. Recessed lighting and gleaming wide-plank wood floors lend an

    Susan Malan William Pitt Sotheby's Int'l

    25 Spring St, Chester, CT 06412
  • 95 Cedar Swamp Rd, Chester, CT 06412
    95 Cedar Swamp Rd, Chester, CT 06412
    95 Cedar Swamp Rd, Chester, CT 06412
    /40

    $1,017,000

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft

    95 Cedar Swamp Rd, Chester, CT 06412

    Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester. Bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning views over Shailer Pond, this home brings the outdoors in from every angle.

    Rachel Welch William Raveis Real Estate

    95 Cedar Swamp 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
  • 95 Shailer Pond Rd, Deep River, CT 06417
    95 Shailer Pond Rd, Deep River, CT 06417
    95 Shailer Pond Rd, Deep River, CT 06417
    /40

    $1,017,000

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft

    95 Shailer Pond Rd, Deep River, CT 06417

    Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester, bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning panoramic views over Shailer Pond, this home brings the outdoors in from

    Rachel Welch William Raveis Real Estate

    95 Shailer Pond Rd, Deep River, CT 06417
  • 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 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    /40

    $645,000

    • 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
  • 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 Open Sat 10AM - 12PM

    • 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
  • 43 N Main St, Chester, CT 06412
    43 N Main St, Chester, CT 06412
    43 N Main St, Chester, CT 06412
    /40

    $749,900

    • 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 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
  • 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

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 102 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, CT over the last 12 months is $540,000.

Housing Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$540,000
Average Price Per Sq Ft
$440
Number of Homes for Sale
0
Last 12 months Home Sales
13
Months of Supply
0.00
Median List Price
$599,000
Median Change From 1st List Price
10%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 10 houses for sale, offering an array of options for potential buyers. With houses priced between $645,000 to $1,150,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $599,000, while the average sale price is $902,307, offering insights into the local housing market. On average, houses spend 102 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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