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Chester, CT Homes for Sale

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  • 47 E Kings Hwy, Chester, CT 06412
    47 E Kings Hwy, Chester, CT 06412
    47 E Kings Hwy, Chester, CT 06412
    /40

    $2,200,000

    • 4 Beds
    • 3.5 Baths
    • 3,957 Sq Ft

    47 E Kings Hwy, Chester, CT 06412

    A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American

    Agent Photo

    Al Chiarito

    Chiarito Real Estate LLC

    47 E Kings Hwy, Chester, CT 06412
  • 90 Water St, Chester, CT 06412
    90 Water St, Chester, CT 06412
    90 Water St, Chester, CT 06412
    /24

    $274,900

    $25K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 1,034 Sq Ft

    90 Water St, Chester, CT 06412

    Rare waterfront opportunity! Nestled directly on the water, 90 Water St is a 1-bathroom Ranch currently configured as a 1-bedroom, but offering a spacious layout that easily converts to a 2-bedroom home. Built in 1950, the property provides a fantastic foundational footprint. It features a large 13'6" x 20'10" living room and a versatile 10'3" x 20'10" family room-the ideal space to partition

    Luke Florian SSG Real Estate LLC

    90 Water St, Chester, CT 06412
  • 92 Water St, Chester, CT 06412
    92 Water St, Chester, CT 06412
    92 Water St, Chester, CT 06412
    /29

    $299,900

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,217 Sq Ft

    92 Water St, Chester, CT 06412

    Welcome to 92 Water St, a charming 1927 two-story Colonial offering a rare opportunity to own waterfront property in picturesque Chester, CT! This 3-bedroom, 1-bathroom home is perfectly situated right on the water, offering tranquil riverfront views and an unbeatable location just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining.

    Luke Florian SSG Real Estate LLC

    92 Water St, Chester, CT 06412
  • 136 Goose Hill Rd, Chester, CT 06412
    136 Goose Hill Rd, Chester, CT 06412
    136 Goose Hill Rd, Chester, CT 06412
    /40

    $900,000

    Open Sat 11AM - 12:30PM $95K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,343 Sq Ft

    136 Goose Hill Rd, Chester, CT 06412

    Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and

    Chris Torrez RE/MAX One

    136 Goose Hill Rd, Chester, CT 06412
  • 0 Turkey Hill Rd, Chester, CT 06412
    0 Turkey Hill Rd, Chester, CT 06412
    0 Turkey Hill Rd, Chester, CT 06412
    /19

    $75,000

    $25K PRICE DROP
    • Land
    • 1 Acre
    • $75,000 per Acre

    0 Turkey Hill Rd, Chester, CT 06412

    Discover the perfect setting to build your dream home in the desirable Wig Hill area of Chester, Connecticut. Located near Cockaponset Sate Forest and the scenic Connecticut River valley. This beautiful one-acre level building lot features approximately 211 feet of road frontage and dimensions of roughly 200 x 200 feet, offering ample space and flexibility to bring your custom plans and ideas to

    Charles Kroopneck Charles Kroopneck Real Estate

    0 Turkey Hill Rd, Chester, CT 06412
  • 42 Straits Rd, Chester, CT 06412
    42 Straits Rd, Chester, CT 06412
    42 Straits Rd, Chester, CT 06412
    /24

    $495,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    42 Straits Rd, Chester, CT 06412

    Discover the incredible potential of this custom-built Colonial, ready for your personal style and finishing touches. Designed with comfort and functionality in mind, the main level features a dedicated home office complete with extensive shelving and abundant storage, perfect for staying organized while working from home. Upstairs, you'll find three generously sized bedrooms and two full baths,

    Stephanie Stone William Raveis/First Town RE

    42 Straits Rd, Chester, CT 06412
  • 59 Maple St, Chester, CT 06412
    59 Maple St, Chester, CT 06412
    59 Maple St, Chester, CT 06412
    /37

    $2,100,000

    • 11 Beds
    • 12 Baths
    • 8,500 Sq Ft

    59 Maple St, Chester, CT 06412

    A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor.

    Connor Wenchell VC Property Group, LLC

    59 Maple St, Chester, CT 06412
  • 288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    /38

    $3,150,000

    • 4 Beds
    • 6 Baths
    • 4,926 Sq Ft

    288 Middlesex Ave, Chester, CT 06412

    Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and

    Nancy Mesham Coldwell Banker Realty

    288 Middlesex Ave, Chester, CT 06412
  • 135 Middlesex Ave, Chester, CT 06412
    135 Middlesex Ave, Chester, CT 06412
    135 Middlesex Ave, Chester, CT 06412
    /35

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    135 Middlesex Ave, Chester, CT 06412

    NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want

    Lisa Genovali Re/Max Valley Shore

    135 Middlesex Ave, Chester, CT 06412
  • 25 Goose Hill Rd, Chester, CT 06412
    25 Goose Hill Rd, Chester, CT 06412
    25 Goose Hill Rd, Chester, CT 06412
    /24

    $385,000

    Open Sat 10AM - 12PM Coming Soon
    • 2 Beds
    • 1.5 Baths
    • 1,454 Sq Ft

    25 Goose Hill Rd, Chester, CT 06412

    Fantastic Opportunity in the Heart of Chester! Discover the potential of this charming 2 Bedroom, 1.5 bath ranch, perfectly situated within walking distance to downtown Chester. The highlight of this home is a newer, heated sunroom boasting wood floors, cathedral ceilings and an abundance of natural light overlooking a private 2.39 acre lot. The partially finished, walk-out lower level offers

    Janet Mashia William Pitt Sotheby's Int'l

    25 Goose Hill Rd, Chester, CT 06412
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    /5

    $799,900

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    88 Winthrop Rd, Chester, CT 06412

    Set on 33.97 private acres in beautiful Chester, CT, this inviting home offers space, privacy, and scenic views. The main level features a primary bedroom with a full bath, while upstairs you'll find 3 additional bedrooms with 2 full baths. The bright, open living room features soaring ceiling and a second floor balcony overlooking the main living space, creating an airy feel. Large south facing

    Peter Walsh Re/Max Valley Shore

    88 Winthrop Rd, Chester, CT 06412
  • 38 Main St, Deep River, CT 06417
    38 Main St, Deep River, CT 06417
    38 Main St, Deep River, CT 06417
    /39

    $650,000

    • 4 Beds
    • 4 Baths
    • 2,560 Sq Ft

    38 Main St, Deep River, CT 06417

    Nestled in the charming town of Deep River, between the villages of Essex and Chester, this beautiful Colonial offers the perfect blend of classic character and modern updates. Featuring 4 bedrooms, 2 full baths and 2 half baths, this spacious home is designed for comfortable living and entertaining. Enter through the welcoming foyer, where the dining room sits to the left, while French doors

    Sue Bowes RE/MAX on the Bay

    38 Main St, Deep River, CT 06417
Connecticut Middlesex County

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 $706,814.
Are home prices dropping in Chester?
Yes, home prices in Chester are down 8% in the last 12 months.
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, 06438, 06419 and 06423.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $645,000. If you put a 20% down payment of $129,000 and had a 30-year fixed mortgage with an interest rate of 6.55%, your estimated principal and interest payment would be $3,280 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $141K 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 Middle School, Lyme-Old Lyme High School and Haddam-Killingworth High School. Browse all the schools in Chester, CT to learn more.

Home Prices in Chester, CT

The median home sale price in Chester, CT is $613,000, up 14% year-over-year. Homes in Chester sell in 65 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$613,000
Median Single Family Sale Price
$610,000
Median 2 Bedroom Sale Price
$550,000
Median 1 Bedroom Sale Price
$274,900
Average Price Per Sq Ft
$343
Number of Homes for Sale
9
Last 12 months Home Sales
38
Months of Supply
2.80
Median List Price
$645,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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