1,700

Chester, CT Homes

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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
  • 9 Maple St Unit E, Chester, CT 06412
    9 Maple St Unit E, Chester, CT 06412
    /2

    $1,400

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    9 Maple St Unit E, Chester, CT 06412

    1 Bedroom apartment in the heart of downtown Chester.

    9 Maple St Unit E, Chester, CT 06412
  • 28 Hoop Pole Hill Rd, Chester, CT 06412

    $760,000

    Sold Nov 03, 2025

    28 Hoop Pole Hill Rd, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 3,396 Sq Ft
    • Built 2008

    Last Sold Summary

    • 5% Below List Price
    • $224/SF
    • 83 Days On Market

    Current Estimated Value $815,484

    Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

    28 Hoop Pole Hill Rd, Chester, CT 06412
  • 12 Meadow Ln, Chester, CT 06412
    12 Meadow Ln, Chester, CT 06412
    12 Meadow Ln, Chester, CT 06412
    /40

    $525,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,971 Sq Ft

    12 Meadow Ln, Chester, CT 06412

    Set at the end of a quiet dead-end road, this three-bedroom ranch offers the ease of one-floor living, exceptional privacy, and over four acres of peaceful surroundings in Chester. Inside, two inviting wood stoves create warm, comfortable gathering spaces, while a newer roof adds peace of mind. Step outside to a covered deck that flows seamlessly to an open deck overlooking the private backyard

    Agent Photo

    Kelly Puorro

    Puorro Realty Group

    12 Meadow Ln, Chester, CT 06412
  • 68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
    /11

    $2,400

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412

    Private 1 bedroom apartment in rear of Victorian estate property. Completely remodeled everything is new and utilities are included. Flexible on length of stay. No smoking, no pets please. Washer/dryer hookups are included. Arrange visit by appointment.

    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
  • 15 Hazen St, Chester, CT 06412

    $220,000

    Sold Apr 21, 2026

    15 Hazen St, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 748 Sq Ft
    • Built 1900

    Last Sold Summary

    • 10% Above List Price
    • $294/SF
    • 14 Days On Market

    Current Estimated Value $221,239

    Last Listing Agent Anthony La Penna Exceptional Real Estate LLC

    15 Hazen St, Chester, CT 06412
  • 22 Goose Hill Rd, Chester, CT 06412
    22 Goose Hill Rd, Chester, CT 06412
    22 Goose Hill Rd, Chester, CT 06412
    /39

    $450,000

    • 3 Beds
    • 3 Baths
    • 1,714 Sq Ft

    22 Goose Hill Rd, Chester, CT 06412

    Welcome to this inviting 3-bedroom split-level ranch, ideally situated within walking distance to the heart of Chester Village. Designed for comfortable living and entertaining, the home features a spacious family room with sliders leading to a large deck overlooking the inground pool. The backyard is an outdoor retreat complete with a pool house, gazebo with electricity, mature fruit trees, and

    Agent Photo

    Kelly Puorro

    Puorro Realty Group

    22 Goose Hill Rd, Chester, CT 06412
  • 3 Maple St Unit 3-1, Chester, CT 06412
    3 Maple St Unit 3-1, Chester, CT 06412
    3 Maple St Unit 3-1, Chester, CT 06412
    /6

    $1,100

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    3 Maple St Unit 3-1, Chester, CT 06412

    1st floor Apartment in the heart of Downtown Chester. Off Street Parking available.

    3 Maple St Unit 3-1, Chester, CT 06412
  • 14 Ferry Rd, Chester, CT 06412

    $420,000

    Sold Sep 24, 2025

    14 Ferry Rd, Chester, CT 06412

    • 4 Beds
    • 1.5 Baths
    • 2,025 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Above List Price
    • $207/SF
    • 35 Days On Market

    Current Estimated Value $437,134

    Last Listing Agent Ian Sacks Coldwell Banker Realty

    14 Ferry Rd, 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
  • 86 Spring St, Chester, CT 06412
    86 Spring St, Chester, CT 06412
    86 Spring St, Chester, CT 06412
    /10

    $1,900

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft
    • House for Rent

    86 Spring St, Chester, CT 06412

    AVAILABLE OCTOBER 2026: Recently renovated unit of a 2 family house in Chester CT. This 850 sq ft living space is heated by propane, has a flexible floor plan, in-unit laundry, new kitchen area floor & new fridge. 2 private entrances and outdoor space with small fire pit. Perfect for a solo renter or couple. WALK TO TOWN - just 8/10 mile to lovely downtown Chester. This charming, quaint town

    86 Spring St, Chester, CT 06412
  • 16 Sypher Rd, Chester, CT 06412

    $616,000

    Sold Jul 14, 2026

    16 Sypher Rd, Chester, CT 06412

    • 2 Beds
    • 2.5 Baths
    • 1,726 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Above List Price
    • $357/SF
    • 42 Days On Market

    Current Estimated Value $577,960

    Last Listing Agent Peg Mitchel Coldwell Banker Realty

    16 Sypher Rd, 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
  • 11 Maple St Unit B, Chester, CT 06412
    11 Maple St Unit B, Chester, CT 06412
    /2

    $2,000

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    11 Maple St Unit B, Chester, CT 06412

    2 Bedroom Apartment in the heart of Downtown Chester. Property includes in unit washer/dryer. One bedroom larger than the second. Kitchen includes dishwasher.

    11 Maple St Unit B, Chester, CT 06412
  • 7 Hickory Hill Dr, Chester, CT 06412

    $549,000

    Sold Mar 24, 2026

    7 Hickory Hill Dr, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,202 Sq Ft
    • Built 1984

    Last Sold Summary

    • $249/SF
    • 6 Days On Market

    Current Estimated Value $552,954

    Last Listing Agent Craig Milton Re/Max Valley Shore

    7 Hickory Hill Dr, 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

    $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
  • 65 Maple St, Chester, CT 06412
    65 Maple St, Chester, CT 06412
    65 Maple St, Chester, CT 06412
    /18

    $1,595

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • House for Rent

    65 Maple St, Chester, CT 06412

    Totally renovated one bedroom apartment w/large bedroom with slider to private deck; large walk-in closet; all new: stainless appliances, counters cabinets, LVT carpet flooring, heating, bathroom; spacious living room; plenty of parking; Located in country setting with easy access to I95 and Route 9, shoreline area or north to Middletown area; one dog or cat allowed with approval; application

    65 Maple St, Chester, CT 06412
  • 25 Spring St, Chester, CT 06412

    $860,000

    Sold Sep 17, 2025

    25 Spring St, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft
    • Built 1860

    Last Sold Summary

    • 4% Below List Price
    • $367/SF
    • 38 Days On Market

    Current Estimated Value $862,425

    Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

    25 Spring St, 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
  • 55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    /21

    $2,500

    Total Monthly Price

    • 2 Beds
    • 3 Baths
    • House for Rent

    55 Liberty St, Chester, CT 06412

    Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its bustling restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an

    55 Liberty St, Chester, CT 06412
  • 12 Deep Hollow Rd, Chester, CT 06412

    $319,900

    Sold Jan 20, 2026

    12 Deep Hollow Rd, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1960

    Last Sold Summary

    • $351/SF
    • 52 Days On Market

    Current Estimated Value $334,541

    Last Listing Agent Craig Milton Re/Max Valley Shore

    12 Deep Hollow Rd, Chester, CT 06412
  • 3 Kirtland Ave, Chester, CT 06412
    3 Kirtland Ave, Chester, CT 06412
    /2

    $282,225

    Pending
    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3 Kirtland Ave, Chester, CT 06412

    REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 1974, this one level home offers approximately 1344 finished square feet, two bedrooms and two full baths, fireplace, unfinished basement and attached one car garage. This home sits on an approximate 14810 sqft lot. "As is" cash only sale with no contingencies or inspections.

    Sherry Price Realhome Services & Solutions

    3 Kirtland Ave, Chester, CT 06412
  • 30 Bokum Rd, Chester, CT 06412

    $442,500

    Sold Oct 20, 2025

    30 Bokum Rd, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 1,198 Sq Ft
    • Built 1930

    Last Sold Summary

    • 4% Above List Price
    • $369/SF
    • 59 Days On Market

    Current Estimated Value $451,454

    Last Listing Agent Max Gill Puorro Realty Group

    30 Bokum 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
  • 80 W Main St, Chester, CT 06412

    $795,000

    Sold Jul 31, 2025

    80 W Main St, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 2,389 Sq Ft
    • Built 1835

    Last Sold Summary

    • 14% Above List Price
    • $333/SF
    • 3 Days On Market

    Current Estimated Value $818,493

    Last Listing Agent Mary Jean Agostini RE/MAX Right Choice

    80 W Main St, Chester, CT 06412
    • 12 Liberty St, Chester, CT 06412

      Est $723,918

      Not Listed For Sale

      12 Liberty St, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 2,713 Sq Ft
      • Built 1925
      12 Liberty St, Chester, CT 06412

      Last Sold Summary

      • 3 Days On Market

  • 6 Jagger Ln, Chester, CT 06412
    6 Jagger Ln, Chester, CT 06412
    6 Jagger Ln, Chester, CT 06412
    /40

    $805,000

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 2,428 Sq Ft

    6 Jagger Ln, Chester, CT 06412

    Step into timeless New England charm with this beautifully updated 1901 Colonial, where classic character meets modern comfort just moments from the heart of Chester. Thoughtfully renovated between 2008 and 2023, this inviting home offers warm, sun-filled spaces designed for both everyday living and and entertaining. Gather in the formal living and dining rooms, enjoy casual meals in the updated

    Maddy Mattson Coldwell Banker Realty

    6 Jagger Ln, Chester, CT 06412
  • 14 Maple St, Chester, CT 06412

    $810,000

    Sold Nov 14, 2025

    14 Maple St, Chester, CT 06412

    • 3 Beds
    • 3.5 Baths
    • 2,322 Sq Ft
    • Built 1755

    Last Sold Summary

    • 1% Above List Price
    • $349/SF
    • 6 Days On Market

    Current Estimated Value $841,974

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    14 Maple St, Chester, CT 06412
    • 230 W Main St, Chester, CT 06412

      Est $425,611

      Not Listed For Sale

      230 W Main St, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 1,530 Sq Ft
      • Built 1986
      230 W Main St, Chester, CT 06412

      Last Sold Summary

      • 24 Days On Market

  • 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
  • 69 Spring St, Chester, CT 06412

    $715,000

    Sold Jul 25, 2025

    69 Spring St, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,702 Sq Ft
    • Built 1883

    Last Sold Summary

    • 10% Above List Price
    • $420/SF
    • 30 Days On Market

    Current Estimated Value $728,360

    Last Listing Agent Rachel Welch William Raveis Real Estate

    69 Spring St, Chester, CT 06412

Showing Results 1 - 40, Page 1 of 18

Connecticut Middlesex County

Real Estate & Homes

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 64 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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