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Chester, CT Homes for Sale

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  • /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, sure to reward with year-round views! Completely and thoughtfully 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,

    Agent Photo

    Claudia O'Connell

    William Raveis Real Estate

    (860) 590-3562

    131 Middlesex Ave, Chester, CT 06412
  • /18

    $199,497

    • Land
    • 25.53 Acres
    • $7,814 per Acre

    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412

    Residential - 25.53 ac Lot in Chester, CTPricing Details:Seller Financing: $43,889.34 Down | $3,332.59 per monthHere’s your chance to own a remarkable 25.53-acre property in the heart of Chester, CT, Middlesex County. While the parcel is landlocked with no legal access, it can be reached via the Deep River through state-owned land, and Pine Ledge Road comes close to the

    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
  • /12

    $350,000

    • 2 Beds
    • 1 Bath
    • 1,012 Sq Ft

    21 E Liberty St, Chester, CT 06412

    Rehab property - CASH only - AS-IS Sale. There is a buried oil tank - seller will not be removing.

    Rachel Welch William Raveis Real Estate

    21 E Liberty 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
  • /33

    $469,900

    • 4 Beds
    • 2 Baths
    • 1,516 Sq Ft

    36 Kings Hwy, Chester, CT 06412

    Charming Stone Home on Nearly 4 Acres! Just minutes from Chester Village, this distinctive home blends character and modern updates. Enjoy an eat-in kitchen with quartz counters, 3-4 bedrooms, and a versatile home office. Recent upgrades include hardwood floors, new roof and gutters, furnace, oil tank, solar panels, and surveillance system. A detached stone 2-car garage completes this rare find!

    Craig Milton Re/Max Valley Shore

    36 Kings Hwy, 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
  • /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
  • /37

    $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
  • /18

    $199,497

    • Land
    • 25.53 Acres
    • $7,814 per Acre

    00 Hoop Pole Hill Rd, Chester, CT 06412

    Here's your chance to own a remarkable 25.53-acre property in the heart of Chester, CT, Middlesex County. While the parcel is landlocked with no legal access, it can be reached via the Deep River through state-owned land, and Pine Ledge Road comes close to the boundary, making it ideal for recreational activities and hunting. Conveniently located near Route 9, just off Exit 8, this expansive

    Derek Greene Derek Greene

    00 Hoop Pole Hill Rd, 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
  • /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
  • /10

    $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
  • /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
  • /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
  • /29

    $525,000 Coming Soon

    • 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
  • /40

    $715,000

    • 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

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.

Frequently Asked Questions

What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $750,902.
How many homes have sold over the last 12 months in Chester, CT?
38 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 $600,000. If you put a 20% down payment of $120,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $2,970 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $127K 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

Housing Trends

Median Sale Price
$557,500
Median Single Family Sale Price
$549,000
Average Price Per Sq Ft
$318
Number of Homes for Sale
7
Last 12 months Home Sales
38
Months of Supply
2.20
Median List Price
$600,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
31%
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