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Chester, CT Homes 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

    $549,000

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

    131 Middlesex Ave, Chester, CT 06412

    Discover this waterfront delight in charming Chester, rewarding with year-round views! Completely renovated in 2012 from the ground up (including brand new septic system), 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 1st floor spaces (roomy mudroom, full bath and laundry

    Agent Photo

    Claudia O'Connell

    William Raveis Real Estate

    (860) 590-3562

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

    $799,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    9 Hickory Hill Dr, Chester, CT 06412

    Welcome to 9 Hickory Hill Drive! Set high on a hill in the heart of the charming Connecticut River Village of Chester. This striking Contemporary offers over 2800 sqft. of light-filled living space on 1.23 private acres-just a 3/10 mi stroll to Main St. The inviting foyer opens to a stunning, sun-drenched living area with skylights and gleaming hardwood floors throughout the living room, dining

    Kathy Schellens William Pitt Sotheby's Int'l

    9 Hickory Hill Dr, Chester, CT 06412
  • 35 Maple St, Chester, CT 06412
    35 Maple St, Chester, CT 06412
    35 Maple St, Chester, CT 06412
    /37

    $799,000 Open Sun 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    35 Maple St, Chester, CT 06412

    Steps to the Village! Vintage 1765 Cape with many updates but still true to the original charm of the Joseph Shipman House. Two staircases, 4 working firplaces, King's Board floors, wonderful floorplan and an up-to-date kitchen makes this home a step back in time but with the amenities of today. Quartz countertops and a complete kitchen renovation in 2017. New rear pressure treated deck in 2017.

    Deborah Rowe William Raveis Real Estate

    35 Maple St, Chester, CT 06412
  • 15 Hazen St, Chester, CT 06412
    15 Hazen St, Chester, CT 06412
    15 Hazen St, Chester, CT 06412
    /32

    $229,000

    • 3 Beds
    • 1 Bath
    • 748 Sq Ft

    15 Hazen St, Chester, CT 06412

    Highest & best by Monday 11/17. OH Saturday 11/15. Charming 4-season cottage with views of Cedar Lake! Corner lot with deck, outdoor shower, and parking. Features an eat-in kitchen, open living area, 3 bedrooms, and hardwood floors.

    Dillon Cass eRealty Advisors, Inc.

    15 Hazen St, Chester, CT 06412
  • 79 Middlesex Ave, Chester, CT 06412
    79 Middlesex Ave, Chester, CT 06412
    79 Middlesex Ave, Chester, CT 06412
    /32

    $449,000

    • 2 Beds
    • 1 Bath
    • 1,470 Sq Ft

    79 Middlesex Ave, Chester, CT 06412

    Charming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends timeless New England character with everyday comfort and walk-to-village convenience. Warm hardwood floors flow throughout the light-filled living room into the updated kitchen with its beautiful bow window and dining area. The kitchen is replete with ample granite counters, perfect for the aspiring chef! The

    Gigi Giordano Taylor Compass Connecticut, LLC

    79 Middlesex Ave, Chester, CT 06412
  • 6 W Main St, Chester, CT 06412
    6 W Main St, Chester, CT 06412
    6 W Main St, Chester, CT 06412
    /39

    $725,000

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft

    6 W Main St, Chester, CT 06412

    EXCELLENT LOCATION, EXCELLENT CONDITION! Lovingly restored 2-family in the heart of Chester Village with historic provenance. Perfect blend of old-school New England charm and modern updates including new siding, full insulation, and A/C. PRIME VILLAGE LOCATION - walk to Chester's vibrant fairs, events, dining, and shopping. Easy commute to Rt. 9. BOTH UNITS FEATURE: * 2 bedrooms with original

    MJ Derisio William Pitt Sotheby's Int'l

    6 W Main St, Chester, CT 06412
  • 60 Goose Hill Rd, Chester, CT 06412
    60 Goose Hill Rd, Chester, CT 06412
    60 Goose Hill Rd, Chester, CT 06412
    /36

    $849,900

    • 7 Beds
    • 2 Baths
    • 2,402 Sq Ft

    60 Goose Hill Rd, Chester, CT 06412

    Spectacular 2 Family home newly renovated. Separate entrances and separate driveways. One unit has 4 bedrooms and a bonus room and the other has 3 bedrooms. New septic system. Central air and washer/dryer hookups in each unit. Huge open kitchen/dining/living room area in both units. All wood and tile floors. Even the basement looks new with all new mechanicals. Stone wall along the driveway

    Alexis Devlin Coldwell Banker Realty

    60 Goose Hill Rd, Chester, CT 06412
  • 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
  • 8 Butter Jones Rd, Chester, CT 06412
    8 Butter Jones Rd, Chester, CT 06412
    8 Butter Jones Rd, Chester, CT 06412
    /36

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft

    8 Butter Jones Rd, Chester, CT 06412

    Enchanting Cape with Artisan Post & Beam Charm - Just Down the Road from Chester Village! Tucked away on 2 acres of picturesque land, this whimsical 3-bedroom, 2.5-bath Cape Cod home invites you to live among nature in style. Only a short distance from Cedar Lake and Chester Village, you'll have easy access to endless outdoor adventures and world-class restaurants and shopping just moments

    Amy Graham William Pitt Sotheby's Int'l

    8 Butter Jones Rd, Chester, CT 06412
  • 6 Spring St, Chester, CT 06412
    6 Spring St, Chester, CT 06412
    6 Spring St, Chester, CT 06412
    /40

    $775,000

    • 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
  • 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
  • 11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    /11

    $232,500

    • Land
    • 1.5 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
  • 43 Bokum Rd, Chester, CT 06412
    43 Bokum Rd, Chester, CT 06412
    /2

    $200,000

    • Land
    • 2.25 Acres
    • $88,889 per Acre

    43 Bokum Rd, Chester, CT 06412

    Beautiful potential building lot. Access via Private road, 2.25 acres. Undeveloped.

    Nicholas Tomanelli Coldwell Banker Realty

    43 Bokum Rd, Chester, CT 06412
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    /2

    $985,000

    • Land
    • 33.97 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
  • 5 Mitchell Ln, Deep River, CT 06417
    5 Mitchell Ln, Deep River, CT 06417
    5 Mitchell Ln, Deep River, CT 06417
    /30

    $319,900 Open Sun 12PM - 3PM

    • 2 Beds
    • 1.5 Baths
    • 1,081 Sq Ft

    5 Mitchell Ln, Deep River, CT 06417

    With front porch charm, blooming perennial gardens, and that unmistakable storybook feeling, this home instantly captures your heart. Lovingly cared for over the years, it offers the perfect balance of comfort and character. The updated kitchen opens to a sunlit dining and family area, creating a welcoming space for gatherings. A cozy reading nook and an inviting office and half bath makes the

    Nancy Leonard William Raveis Real Estate

    5 Mitchell Ln, Deep River, CT 06417
Connecticut Middlesex County Chester

Real Estate & Homes 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

Frequently Asked Questions

What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $774,749.
How many homes have sold over the last 12 months in Chester, CT?
40 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 06412, 06417, 06419, 06438 and 06371.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $649,000. If you put a 20% down payment of $129,800 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $3,190 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $137K 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, Lyme-Old Lyme Middle School and Haddam-Killingworth High School. Browse all the schools in Chester, CT to learn more.

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 47 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, CT over the last 12 months is $596,000, up 45% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$596,000
Median Single Family Sale Price
$610,000
Average Price Per Sq Ft
$334
Number of Homes for Sale
9
Last 12 months Home Sales
40
Months of Supply
2.70
Median List Price
$649,000
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
45%
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