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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

    $649,000

    • 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
  • 0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
    /18

    $249,497

    • Land
    • 25.53 Acres
    • $9,773 per Acre

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

    Residential - 25.53 ac Lot in Chester, CTPricing Details:Seller Financing: $54,889.34 Down | $4,167.84 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

    Timothy Ebie

    0 Hoop Pole Hill Rd Unit 24625958, 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

    • 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
  • 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
  • 14 Maple St, Chester, CT 06412
    14 Maple St, Chester, CT 06412
    14 Maple St, Chester, CT 06412
    /9

    $799,000 Open House 9/27

    • 3 Beds
    • 3.5 Baths
    • 2,322 Sq Ft

    14 Maple St, Chester, CT 06412

    Quintessential Chester! This Federal Greek Revival Post and Beam Antique Colonial has been lovingly restored and updated. Mere steps to the Town Center! Taste the true flavor of New England by enjoying this characteristically charming Connecticut Village, well known for its resturants, art galleries, and seasonal events, along with boat marinas and yacht clubs for summer fun. Special features of

    Deborah Rowe William Raveis Real Estate

    14 Maple St, Chester, CT 06412
  • 8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    /40

    $775,000 Open Sat 1PM - 3PM

    • 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 Open Sat 11AM - 1PM

    • 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
  • 00 Hoop Pole Hill Rd, Chester, CT 06412
    00 Hoop Pole Hill Rd, Chester, CT 06412
    00 Hoop Pole Hill Rd, Chester, CT 06412
    /18

    $239,497

    • Land
    • 25.53 Acres
    • $9,381 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
  • 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
  • 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
  • 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
  • 11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, 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
  • 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
  • 1 Route 148, Killingworth, CT 06419
    1 Route 148, Killingworth, CT 06419
    1 Route 148, Killingworth, CT 06419
    /39

    $699,900 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,927 Sq Ft

    1 Route 148, Killingworth, CT 06419

    Just Four Years Young - Cape-Style Beauty on Eight Private Acres! This one-floor living opportunity truly checks all the boxes! Privately sited on a rear eight-acre lot-level, landscaped, and professionally maintained-this gorgeous cape-style home offers both comfort and classic design. Features include a spacious and gracious first-floor primary suite, an inviting open floor plan, and quality

    Lynn Lehrman Re/Max Valley Shore

    1 Route 148, Killingworth, CT 06419
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 $748,433.
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 $640,000. If you put a 20% down payment of $128,000 and had a 30-year fixed mortgage with an interest rate of 6.35%, 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 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 $538,500, up 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$538,500
Median Single Family Sale Price
$582,000
Average Price Per Sq Ft
$324
Number of Homes for Sale
10
Last 12 months Home Sales
42
Months of Supply
2.90
Median List Price
$640,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
19%
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