11

Chester, CT Homes for Sale

Section Image Section Image
  • 131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    /28

    $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

    • 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
  • 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

    Back on market! Inspection will show there is some termite damage in one of beams in basement. 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
    /37

    $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

    $775,000

    • 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 away.

    Amy Graham William Pitt Sotheby's Int'l

    8 Butter Jones 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
  • 19 Castle View Dr, Chester, CT 06412
    19 Castle View Dr, Chester, CT 06412
    /2

    $209,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    19 Castle View Dr, Chester, CT 06412

    Investor/Builder Opportunity! Discover a rare opportunity in charming Chester, Connecticut! Minutes from Chester's vibrant village center known for its restaurants, boutiques, galleries, theater and farmer's market. This property offers tremendous potential for the right buyer. The existing structure is not currently habitable! This property require significant renovation/demolition due its

    Sharon Linder Berkshire Hathaway NE Prop.

    19 Castle View Dr, 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
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 $770,665.
How many homes have sold over the last 12 months in Chester, CT?
42 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 6.19%, your estimated principal and interest payment would be $3,180 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $136K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
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 53 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 $623,750, up 52% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$623,750
Median Single Family Sale Price
$610,000
Average Price Per Sq Ft
$331
Number of Homes for Sale
7
Last 12 months Home Sales
42
Months of Supply
2.00
Median List Price
$649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
52%
How to Buy a Home How to Finance a Home How to Sell a 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group