8

Chester, CT Homes for Sale

Section Image
  • /22

    $329,900

    • 1 Bed
    • 1 Bath
    • 642 Sq Ft

    96 Goose Hill Rd, Chester, CT 06412

    A thoughtfully designed home set on four acres in the heart of Chester. With a mix of open land and lightly wooded areas, the property offers both privacy and usable space in a peaceful, natural setting. Inside, the home features a bedroom on the main level, a full bathroom, and a full eat-in kitchen equipped with a stove, refrigerator, microwave, and ample cabinet space. The open living area is

    Jason Archer PMI East Lyme

    96 Goose Hill Rd, Chester, CT 06412
  • /40

    $699,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,389 Sq Ft

    80 W Main St, Chester, CT 06412

    Nestled in the storybook town of Chester, Connecticut-renowned for its vibrant arts scene, scenic countryside, and charming village center-this one-of-a-kind historic home lovingly maintained by its current steward,offers a truly inspiring lifestyle. Set on lush, idyllic grounds framed by mature trees, gardens,&stone walls, the property exudes timeless New England beauty.A collection of

    Mary Jean Agostini RE/MAX Right Choice

    80 W Main St, Chester, CT 06412
  • /39

    $764,900

    • 3 Beds
    • 1.5 Baths
    • 1,538 Sq Ft

    43 N Main St, Chester, CT 06412

    Calling all artists, authors, creatives. This is the perfect space to create, dream, let your imagination bloom. Surrounded by Chester Creek and across the street from a beautiful waterfall sits 43 North Main Street Chester. 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 fireplace,

    Susan Malan William Pitt Sotheby's Int'l

    43 N Main 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
  • /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
  • /40

    $694,000

    • 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
  • /10

    $232,500

    • Land
    • 1.50 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

    $985,000

    • Land
    • 34 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

Why Live in Chester

Chester is situated alongside the Connecticut River, offering a tranquil country lifestyle and picturesque water vistas. Additionally, the town boasts a distinctive feature known as the Chester-Hadlyme Ferry. It is one of the few remaining operational ferries on the Connecticut River and provides an enjoyable means of transportation to Hadlyme. It contributes to the pervasive feeling of historical significance that permeates Chester, particularly in the downtown area. “Chester is smaller than most towns, like nearby Mystic, but it has a seclude ...

Frequently Asked Questions

What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $681,800.
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 06457, 06443, 06437, 06405 and 06424.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $525,000. If you put a 20% down payment of $105,000 and had a 30-year fixed mortgage with an interest rate of 6.84%, your estimated principal and interest payment would be $2,750 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $118K 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, Haddam-Killingworth High School and Lyme-Old Lyme Middle School. Browse all the schools in Chester, CT to learn more.

Home Trends in Chester, CT

Housing Trends

Median Sale Price
$475,000
Median Single Family Sale Price
$537,000
Average Price Per Sq Ft
$302
Number of Homes for Sale
5
Last 12 months Home Sales
42
Months of Supply
1.40
Median List Price
$525,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
How to Buy a Home How to Finance a Home How to Sell a Home