Section Image Section Image

Explore Similar Homes Within 2 Miles of Chester, CT

  • 2 Porges Rd, East Haddam, CT 06423
    2 Porges Rd, East Haddam, CT 06423
    2 Porges Rd, East Haddam, CT 06423
    /20

    $2,600 per month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

    2 Porges Rd, East Haddam, CT 06423

    Newly renovated 1-bedroom, 1-bath apartment with air conditioning and all utilities-including internet-fully included. This bright, single-level unit features large glass doors that fill the space with natural light, no stairs, and a private backyard perfect for relaxing or entertaining. Conveniently located just up the road from the Goodspeed Opera House, the Gelston House, and Route 9, this

    Agent Photo

    Cory Tyler

    Berkshire Hathaway NE Prop.

    (860) 772-0481

    2 Porges Rd, East Haddam, CT 06423
  • 105 Bridge Rd, Haddam, CT 06438
    105 Bridge Rd, Haddam, CT 06438
    105 Bridge Rd, Haddam, CT 06438
    /21

    $1,950 - $2,050 per month

    Bridge Road Commons

    1 Bed

    105 Bridge Rd, Haddam, CT 06438

    Experience modern living in the heart of Haddam, CT, where our open concept apartment units seamlessly blend comfort and style. Nestled in this picturesque town, our community features a clubhouse and inviting outdoor spaces, offering a perfect backdrop to enjoy Haddam's quaint charm. With scenic trails, historic landmarks, and the gentle flow of the nearby Connecticut River, Bridge Road Commons

    105 Bridge Rd, Haddam, CT 06438
  • 171 Main St, Deep River, CT 06417
    171 Main St, Deep River, CT 06417
    171 Main St, Deep River, CT 06417
    /11

    $2,000 per month

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

    171 Main St, Deep River, CT 06417

    Fully Remodeled 1 Bedroom Unit 1 Floor Living Right in Downtown, Living room, Kitchen, bedroom and Full bathroom - No pets Allowed. 700 SQFT.

    Craig Milton Re/Max Valley Shore

    171 Main St, Deep River, CT 06417
  • 26 Sunset Terrace Unit 26C, Essex, CT 06426
    26 Sunset Terrace Unit 26C, Essex, CT 06426
    26 Sunset Terrace Unit 26C, Essex, CT 06426
    /9

    $1,500 per month

    Apartment for Rent

    1 Bed

    26 Sunset Terrace Unit 26C, Essex, CT 06426

    26 Sunset Terrace Unit 26C, Essex, CT 06426
  • 164 Main St Unit A, Deep River, CT 06417
    164 Main St Unit A, Deep River, CT 06417
    164 Main St Unit A, Deep River, CT 06417
    /12

    $1,250 per month

    • 1 Bath
    • 500 Sq Ft
    • Apartment for Rent

    164 Main St Unit A, Deep River, CT 06417

    Don't miss this fantastic rental opportunity, available for immediate occupancy! This charming first-floor studio-style apartment offers 1 bedroom and 1 full bathroom, ideal for comfortable and efficient living. Brand-new mini split system for year-round comfort recently installed. Enjoy the convenience of off-street parking with one assigned space in the shared driveway. Situated in a prime

    Alexander Cortez-Rich Silver and Oak Realty

    164 Main St Unit A, Deep River, CT 06417
  • 15 Sunset Terrace, Essex, CT 06426
    15 Sunset Terrace, Essex, CT 06426
    15 Sunset Terrace, Essex, CT 06426
    /17

    $1,800 per month

    • Studio
    • 1 Bath
    • 540 Sq Ft
    • Condo for Rent

    15 Sunset Terrace, Essex, CT 06426

    Embrace the charm of this modern Essex, CT studio condo! Unit #10 has an open floor plan and is located on the second floor. Step through the private entrance to a staircase leading up to the studio, where you are welcomed by large windows and a skylight that bathes the space in natural light, creating a bright and inviting ambiance. The updated full bath has a contemporary tile shower, a chic

    15 Sunset Terrace, Essex, CT 06426
  • 10 Phelps Ln, Deep River, CT 06417
    10 Phelps Ln, Deep River, CT 06417
    10 Phelps Ln, Deep River, CT 06417
    /34

    $2,500 per month

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • House for Rent

    10 Phelps Ln, Deep River, CT 06417

    Great Ranch Rental - Newly Remodeled - 3 Bedrooms, Large Living Room and Kitchen. All New Appliances with newer dishwasher. New Countertops and new flooring. Washer and Drier in the unit. Central Air. Garage with electric. Great back yard fenced in. Walking distance to the Connecticut River where you can have lunch in the gazebo, take a ride on the Becky Thatcher in the summer months, and ride on

    Sharon Fox Carl Guild & Associates

    10 Phelps Ln, Deep River, CT 06417
  • 107 Main St Unit 107A, Ivoryton, CT 06442
    107 Main St Unit 107A, Ivoryton, CT 06442
    107 Main St Unit 107A, Ivoryton, CT 06442
    /3

    $2,000 per month

    • 2 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Condo for Rent

    107 Main St Unit 107A, Ivoryton, CT 06442

    Located in the heart of Ivoryton Village in the town of Essex. Just miles from the Connecticut river and the Long Island Sound. Second and third floor apartment with each floor having it's own full bath.

    107 Main St Unit 107A, Ivoryton, CT 06442
  • 82 River Rd, Essex, CT 06426
    82 River Rd, Essex, CT 06426
    82 River Rd, Essex, CT 06426
    /21

    $2,200 per month

    • 2 Beds
    • 1.5 Baths
    • 912 Sq Ft
    • House for Rent

    82 River Rd, Essex, CT 06426

    River Road Essex. This is a charming antique 2 bedroom converted gate house cottage with wonderful details. Wood floors and paneled walls. Large windows, beautiful stone walls and beamed ceilings in the living room. Kitchen has washer and dryer. Includes one car parking in the barn/garage. Private lawn area for gardening is also included. This property is non smoking and no pets are allowed.

    Susan Malan William Pitt Sotheby's Int'l

    82 River Rd, Essex, CT 06426
  • 6 Summit St Unit 1 Bedroom ALL Utility Inc, Essex, CT 06442
    6 Summit St Unit 1 Bedroom ALL Utility Inc, Essex, CT 06442
    6 Summit St Unit 1 Bedroom ALL Utility Inc, Essex, CT 06442
    /25

    $1,975 per month

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

    6 Summit St Unit 1 Bedroom ALL Utility Inc, Essex, CT 06442

    All Utilities inclusive- 600 SF 1 BedroomFull Bathheat, hot water, electricity, water, wifi includedlarge deck off kitchenclose to all restaurants, theatrefurnished or notdriveway with parkingno petsno smokingPlease reply with your details, situation etc -

    6 Summit St Unit 1 Bedroom ALL Utility Inc, Essex, CT 06442
  • 15 Main St Unit 1, Essex, CT 06426
    15 Main St Unit 1, Essex, CT 06426
    15 Main St Unit 1, Essex, CT 06426
    /10

    $1,950 per month

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

    15 Main St Unit 1, Essex, CT 06426

    Tired of the Hamptons, need change? Centrally located on the CT River for year round weekend getaways in the small quaint town of Essex, CT. Completely newly renovated one bedroom apartment, located in the center of historic village. The perfect seasonal year round rental for Manhattanites, or locals / boaters, golfers, CT country goers, 2 Hours from Manhattan & 2 Hours from Boston... Amtrack

    Kathy Schellens William Pitt Sotheby's Int'l

    15 Main St Unit 1, Essex, CT 06426
  • 538 Winthrop Rd Unit 9, Deep River, CT 06417
    538 Winthrop Rd Unit 9, Deep River, CT 06417
    538 Winthrop Rd Unit 9, Deep River, CT 06417
    /12

    $2,375 per month

    • 2 Beds
    • 1 Bath
    • 680 Sq Ft
    • House for Rent

    538 Winthrop Rd Unit 9, Deep River, CT 06417

    Beautiful home located at the most amazing location right on Star Lake! This home features new appliances and is ready for new occupants. This 2 bedroom features 50 feet of Lake Star frontage and it is perfect for kayaks and fishing! Apply online and get the chance to live right next to beautiful nature.

    Mikail Naska Eagle Eye Realty PLLC

    538 Winthrop Rd Unit 9, Deep River, CT 06417
  • 26 Sunset Terrace Unit B3, Essex, CT 06426
    26 Sunset Terrace Unit B3, Essex, CT 06426
    26 Sunset Terrace Unit B3, Essex, CT 06426
    /9

    $1,850 per month

    • 2 Beds
    • 1 Bath
    • 650 Sq Ft
    • House for Rent

    26 Sunset Terrace Unit B3, Essex, CT 06426

    Welcome to Essex Hills apartment complex. This charming 2-bedroom, 1-bath rental in Essex provides a comfortable and updated living space. Recently renovated, it features bright living areas and a modernized bathroom. Located in a quiet neighborhood close to Essex Village, this home provides easy access to local shops, dining, and scenic spots. A great option for anyone looking for a welcoming

    Mantas Laureckis William Raveis Real Estate

    26 Sunset Terrace Unit B3, Essex, CT 06426
  • 23 Main St Unit 5 The Chace Suite, East Haddam, CT 06423
    23 Main St Unit 5 The Chace Suite, East Haddam, CT 06423
    23 Main St Unit 5 The Chace Suite, East Haddam, CT 06423
    /18

    $1,900 per month

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Apartment for Rent

    23 Main St Unit 5 The Chace Suite, East Haddam, CT 06423

    ALL UTILITIES INCLUDED. Brand new unit - totally remodeled in 2024. Handicapped accessible throughout, Quality throughout. Set up primarily as a B+B so all kitchen implements, pots and pans, glasses etc are there. Linens and towels can be provided. Cleaning service is available at an extra charge. Two other units in the building, including a 2BR are being finished off, to be available by mid

    Allen Jacobs Sunset Creek Realty, LLC

    23 Main St Unit 5 The Chace Suite, East Haddam, CT 06423
  • 12 Scholes Ln, Essex, CT 06426
    12 Scholes Ln, Essex, CT 06426
    12 Scholes Ln, Essex, CT 06426
    /25

    $4,400 per month

    • 2 Beds
    • 1.5 Baths
    • 1,329 Sq Ft
    • House for Rent

    12 Scholes Ln, Essex, CT 06426

    Rarely available! This historic 1860 Essex Village waterfront home is nestled on a quiet lane with direct waterfront on Middle Cove. Step back in time and experience the charm of this Vintage home, complete with many original features, while still enjoying modern amenities and updated appliances. The home boasts original wood floors, a stunning floor-to-ceiling bay window in the living room, and

    Kathy Schellens William Pitt Sotheby's Int'l

    12 Scholes Ln, Essex, CT 06426
  • 23 Main St Unit 2 - The Burton Suite, East Haddam, CT 06423
    23 Main St Unit 2 - The Burton Suite, East Haddam, CT 06423
    23 Main St Unit 2 - The Burton Suite, East Haddam, CT 06423
    /18

    $1,800 per month

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

    23 Main St Unit 2 - The Burton Suite, East Haddam, CT 06423

    Brand new unit to be completed soon- The Burton Suite available at the completely remodeled Society Hall, a stone's throw from The Gelston House, Goodspeed Opera House, and the rest of downtown East Haddam!

    Stephanie Jacobs Sunset Creek Realty, LLC

    23 Main St Unit 2 - The Burton Suite, East Haddam, CT 06423
  • 52 Essex St, Deep River, CT 06417
    52 Essex St, Deep River, CT 06417
    52 Essex St, Deep River, CT 06417
    /11

    $1,695 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Apartment for Rent

    52 Essex St, Deep River, CT 06417

    Village View Apartment Homes where you can expect a touch of style. Beautiful newly renovated 2 bedroom energy efficient apartment homes come with hardwood flooring, open kitchens with an island, and plenty of storage. After returning home to our quiet community you can take a short walk into charming Deep River town center for great food and entertainment, or hike one of the local nature trails

    Mark Reyher Reyher Real Estate

    52 Essex St, Deep River, CT 06417
Connecticut Chester

Homes for Rent in Chester, CT

Why Live in Chester

Chester, nestled along the Connecticut River, provides a serene country lifestyle with scenic water views. The Chester-Hadlyme Ferry, one of the few operational ferries on the river, adds to the town's historical charm, particularly in its pedestrian-friendly downtown area, which features buildings listed on the National Register of Historic Places. Chester's downtown is known for its well-preserved historic ambiance and local attractions, including the popular River Tavern, Fresh Salt, and Whistle Stop. The neighborhood experiences distinct seasonal weather, enhancing its picturesque setting. Homes in Chester range from older Victorian, Cape Cod, and colonial styles, with properties spanning from three-bedroom houses on nearly 2,000 square feet of land to larger estates on over 1.5 acres. The area is part of the tri-town region, including Essex and Deep River, known for its expansive lot sizes and proximity to the Connecticut River. Chester's crime rate is lower than the national average, contributing to its appeal. Students attend highly rated schools in Regional School District 4, including Chester Elementary School and Valley Regional High School, both recognized for their strong academic programs. Outdoor enthusiasts can visit the Pattaconk Recreation Area, which offers woodland trails and access to the Pattaconk Reservoir. Unique transportation options include the Chester-Hadlyme Ferry and a local airport, with Route 9 serving as the main thoroughfare. Chester's combination of historical charm, natural beauty, and practical amenities makes it a distinctive neighborhood within the tri-town area.
Learn more about living in Chester

Frequently Asked Questions

What are the most popular neighborhoods in Chester, CT for renters?
The most popular neighborhood in Chester, CT for renters is Westfield.
What are the most popular zip codes in Chester, CT for renters?
The most popular zip codes in Chester, CT for renters include 06405, 06443, 06457, 06320 and 11957.
How to Rent 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