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Explore Similar Townhomes Within 25 Miles of Chester, CT

  • 23 Fort Pond Rd, Montauk, NY 11954
    23 Fort Pond Rd, Montauk, NY 11954
    23 Fort Pond Rd, Montauk, NY 11954
    /23

    $1,350,000

    • 2 Beds
    • 2 Baths
    • 893 Sq Ft

    23 Fort Pond Rd, Montauk, NY 11954

    Just listed , renovated and Large two bedroom, two bath condominium situated on Fort Pond Bay with the most beautiful sunsets. This gated thirty-acre community offers many amenities which include a 32 x 70 heated gunite pool, Jacuzzi, sauna and 5 tennis courts. Enjoy relaxing on the bay beach with a 1,075 ft. fishing pier with gazebo. Grab a bite at Navy Beach Restaurant on adjacent beach or

    Agent Photo

    William Wolff

    Douglas Elliman Real Estate

    (631) 614-4958

    23 Fort Pond Rd, Montauk, NY 11954
  • 81 Shea Cir, Cheshire, CT 06410
    81 Shea Cir, Cheshire, CT 06410
    81 Shea Cir, Cheshire, CT 06410
    /13

    $778,572 Open Sat 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,975 Sq Ft

    81 Shea Cir, Cheshire, CT 06410

    Carriage home complete with designer appointed finishes! Available in the Summer of 2025. Carriage Home is stylish and sophisticated, yet every bit as warm, our Carriage homes provide the perfect mix of luxury, function, and comfort. You'll feel its charm upon entering the foyer, which leads to the heart of the home. A bright, open kitchen overlooks the dining area and wow-factor, the 2-story

    Felicity LeClair EG Group Realty

    81 Shea Cir, Cheshire, CT 06410
  • 31 Soderman Way Unit 36683451, Cheshire, CT 06410
    31 Soderman Way Unit 36683451, Cheshire, CT 06410
    31 Soderman Way Unit 36683451, Cheshire, CT 06410
    /14

    $534,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    Townhome Plan at The Reserve at Stonebridge Crossing, Cheshire, CT 06410

    Builder Photo

    EG Home

    Builder

    31 Soderman Way Unit 36683451, Cheshire, CT 06410
  • 500 Meadow Ct Unit 28, Southold, NY 11971
    500 Meadow Ct Unit 28, Southold, NY 11971
    500 Meadow Ct Unit 28, Southold, NY 11971
    /29

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 3,735 Sq Ft

    500 Meadow Ct Unit 28, Southold, NY 11971

    Lovely light-filled 3-bedroom 3 bath inland end-unit in The Cove – a small hidden gem of a waterfront community nestled in the heart of the North Fork. There are boat slips for your boat with easy access to the beautiful Peconic Bay, boat racks for your paddleboard/kayak, a gunite in-ground pool, and combination tennis/pickleball court – both of which were just resurfaced this year! The airy open

    Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

    500 Meadow Ct Unit 28, Southold, NY 11971
  • 90 Shea Cir Unit 90, Cheshire, CT 06410
    90 Shea Cir Unit 90, Cheshire, CT 06410
    90 Shea Cir Unit 90, Cheshire, CT 06410
    /13

    $674,900 Open Sat 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    90 Shea Cir Unit 90, Cheshire, CT 06410

    Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy,

    Michael Helmuth EG Group Realty

    90 Shea Cir Unit 90, Cheshire, CT 06410
  • 89 Shea Cir Unit 89, Cheshire, CT 06410
    89 Shea Cir Unit 89, Cheshire, CT 06410
    89 Shea Cir Unit 89, Cheshire, CT 06410
    /13

    $674,900 Open Sat 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    89 Shea Cir Unit 89, Cheshire, CT 06410

    Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy,

    Michael Helmuth EG Group Realty

    89 Shea Cir Unit 89, Cheshire, CT 06410
  • 13 Heritage Ln, Woodbridge, CT 06525
    13 Heritage Ln, Woodbridge, CT 06525
    13 Heritage Ln, Woodbridge, CT 06525
    /19

    $669,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,239 Sq Ft

    13 Heritage Ln, Woodbridge, CT 06525

    This beautifully crafted home offers 2,239 square feet, 3 bedrooms, and 2.5 baths. Featuring a sun-soaked entry, this free-flowing home design is brimming with natural light. The kitchen boasts upgraded Century cabinets, quartz countertops, and stainless steel appliances. The first-floor primary bedroom features a walk-in closet and a lavish bath. Ready for move-in late summer 2025. Disclaimer:

    Builder Photo

    Toll Brothers, Inc.

    Builder

    13 Heritage Ln, Woodbridge, CT 06525
  • 5 Heritage Ln, Woodbridge, CT 06525
    5 Heritage Ln, Woodbridge, CT 06525
    5 Heritage Ln, Woodbridge, CT 06525
    /19

    $569,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,006 Sq Ft

    5 Heritage Ln, Woodbridge, CT 06525

    Love everything about this home. The enormous kitchen boasts name-brand appliances, upgraded countertops, and ample cabinet space. The two-story great room boasts a fireplace and plenty of natural light. The appealing first-floor primary bedroom suite boasts a lavish bath and ample closet space. The versatile loft can be suited to fit your lifestyle. Schedule an appointment to learn more about

    Builder Photo

    Toll Brothers, Inc.

    Builder

    5 Heritage Ln, Woodbridge, CT 06525
  • 3 Heritage Ln, Woodbridge, CT 06525
    3 Heritage Ln, Woodbridge, CT 06525
    3 Heritage Ln, Woodbridge, CT 06525
    /19

    $599,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,239 Sq Ft

    3 Heritage Ln, Woodbridge, CT 06525

    Experience contemporary design in a versatile living space with this move-in ready home. The beautiful foyer welcomes you home with stunning views of the main living space and rear yard. Tall windows in the expanded great room allow for an abundance of natural light. The first-floor primary bedroom suite boasts a spa-like bath and large walk-in closet. This home is situated within walking

    Builder Photo

    Toll Brothers, Inc.

    Builder

    3 Heritage Ln, Woodbridge, CT 06525
  • 10 Hillcrest Dr Unit 36358183, Woodbridge, CT 06525

    $599,995 New Construction

    • 3 Beds
    • 2.5 - 3.5 Baths
    • 1,938 Sq Ft

    Pierpont Plan at Regency at Woodbridge, Woodbridge, CT 06525

    The expertly designed Pierpont immediately impresses with its elegant two-story main living level, featuring a bright foyer and hallway that leads into the spacious great room that offers convenient access to the rear yard. The well-equipped kitchen overlooks a sizable casual dining area and is complemented by a large center island with breakfast bar, plenty of counter and cabinet space, as well

    Builder Photo

    Toll Brothers, Inc.

    Builder

    10 Hillcrest Dr Unit 36358183, Woodbridge, CT 06525
  • 10 Hillcrest Dr Unit 36358185, Woodbridge, CT 06525
    10 Hillcrest Dr Unit 36358185, Woodbridge, CT 06525
    /2

    $645,995 New Construction

    • 3 Beds
    • 2.5 - 3.5 Baths
    • 2,188 Sq Ft

    Pierson Plan at Regency at Woodbridge, Woodbridge, CT 06525

    A thoughtfully designed floor plan that features modern architecture with elegant features defines the beautiufl Pierson. The soaring two-story foyer opens onto a charming two-story great room with desirableaccess to the rear yard. Overlooking a spacious casual dining area, the well-appointed kitchen offers an oversized center island with breakfast bar and ample counter and cabinet space. The

    Builder Photo

    Toll Brothers, Inc.

    Builder

    10 Hillcrest Dr Unit 36358185, Woodbridge, CT 06525
  • 10 Hillcrest Dr Unit 36358187, Woodbridge, CT 06525

    $615,995 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    Silliman Plan at Regency at Woodbridge, Woodbridge, CT 06525

    The beautifully crafted Silliman makes an immediate impression with its inviting porch and foyer that opens onto a palatial two-story casual dining area and soaring two-story great room with desirable access to the rear yard. Adjacent, the well-appointed two-story kitchen features a roomy pantry as well as wraparound counter and cabinet space that surrounds a large center island with breakfast

    Builder Photo

    Toll Brothers, Inc.

    Builder

    10 Hillcrest Dr Unit 36358187, Woodbridge, CT 06525
  • 10 Hillcrest Dr Unit 36358184, Woodbridge, CT 06525

    $665,995 New Construction

    • 3 Beds
    • 2.5 - 3.5 Baths
    • 1,938 Sq Ft

    Pierpont Elite Plan at Regency at Woodbridge, Woodbridge, CT 06525

    An open-concept floor plan with versatile living spaces defines the wonderfully designed Pierpont Elite. The beautiful two-story main living level features a charming foyer offering alluring views of the expansive great room and casual dining area with access to the rear yard. The expertly crafted kitchen is enhanced by an oversized center island with breakfast bar as well as ample counter and

    Builder Photo

    Toll Brothers, Inc.

    Builder

    10 Hillcrest Dr Unit 36358184, Woodbridge, CT 06525
  • 10 Hillcrest Dr Unit 36358186, Woodbridge, CT 06525

    $685,995 New Construction

    • 3 Beds
    • 2.5 - 3.5 Baths
    • 2,188 Sq Ft

    Pierson Elite Plan at Regency at Woodbridge, Woodbridge, CT 06525

    The Pierson Elite features a versatile mix of open-concept living spaces and private retreats. A two-story great room complete with rear yard access is central to an expansive two-story foyer and the expertly crafted kitchen, enhanced by a sizable casual dining area as well as plenty of counter and cabinet space that surrounds a large center island with breakfast bar. Complementing the secluded

    Builder Photo

    Toll Brothers, Inc.

    Builder

    10 Hillcrest Dr Unit 36358186, Woodbridge, CT 06525
  • 22 Lombard Cir Unit 22, North Haven, CT 06473
    22 Lombard Cir Unit 22, North Haven, CT 06473
    22 Lombard Cir Unit 22, North Haven, CT 06473
    /31

    $615,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    22 Lombard Cir Unit 22, North Haven, CT 06473

    This Patton model is sheetrocked and waiting for your interior selections to be made. The Patton model consists of a kitchen in the heart of the living space which opens to the great room and the dining room which makes entertaining a dream. Retire to the upper level where all of your sleeping quarters are located, including the owners bedroom with full bathroom, three additional bedrooms, jack &

    Bridie Bradbury Calcagni Real Estate

    22 Lombard Cir Unit 22, North Haven, CT 06473
  • 2 Lombard Cir Unit 2, North Haven, CT 06473
    2 Lombard Cir Unit 2, North Haven, CT 06473
    2 Lombard Cir Unit 2, North Haven, CT 06473
    /27

    $615,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,906 Sq Ft

    2 Lombard Cir Unit 2, North Haven, CT 06473

    This Stiles Model at Pierpont Hill is the final Stiles model to be built. Currently ready for you to make your selections on the interior. Pierpont Hill's next generation of cleaner, energy-efficient electric-powered duplex homes! This community has all the luxuries of today's standards in a home, along with the ease of outdoor maintenance free living and energy efficient built homes. Offering

    Kristin Daly-Murphy Calcagni Real Estate

    2 Lombard Cir Unit 2, North Haven, CT 06473
  • 20 Lombard Cir Unit 20, North Haven, CT 06473
    20 Lombard Cir Unit 20, North Haven, CT 06473
    20 Lombard Cir Unit 20, North Haven, CT 06473
    /32

    $605,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    20 Lombard Cir Unit 20, North Haven, CT 06473

    This Patton model is a quick delivery unit with all of the upgrades that you will love! It is a complete unit and could close as quickly as you can. The Patton model has the kitchen in the heart of the living space that opens to the great room and the dining room which makes entertaining a dream. Retire to the upper level where all of your sleeping quarters are located, including the owners

    Kristin Daly-Murphy Calcagni Real Estate

    20 Lombard Cir Unit 20, North Haven, CT 06473
  • 4 Lombard Cir Unit 4, North Haven, CT 06473
    4 Lombard Cir Unit 4, North Haven, CT 06473
    4 Lombard Cir Unit 4, North Haven, CT 06473
    /23

    $595,000 New Construction

    • 3 Beds
    • 3 Baths
    • 1,880 Sq Ft

    4 Lombard Cir Unit 4, North Haven, CT 06473

    This Wallace Model at Pierpont Hill is the final Wallace model to be built. Currently ready for you to make your selections on the interior. Pierpont Hill's next generation of cleaner, energy-efficient electric-powered duplex homes! This community has all the luxuries of today's standards in a home, along with the ease of outdoor maintenance free living and energy efficient built homes. Offering

    Bridie Bradbury Calcagni Real Estate

    4 Lombard Cir Unit 4, North Haven, CT 06473
  • 707 Old Montauk Hwy Unit A-57, Montauk, NY 11954
    707 Old Montauk Hwy Unit A-57, Montauk, NY 11954
    707 Old Montauk Hwy Unit A-57, Montauk, NY 11954
    /14

    $949,000 New Construction

    • 2 Beds
    • 1 Bath
    • 601 Sq Ft

    707 Old Montauk Hwy Unit A-57, Montauk, NY 11954

    Spectacular ocean views from this first floor corner apartment located directly across from the Atlantic Ocean. Open year around, this property features two bedrooms, one bath, kitchen, fireplace, with basement storage, laundry on premises, heated in-ground pool, designated parking, internet and Direct TV included in maintenance fees. Property Superintendent on duty year-around. Walking

    Kenneth Kalafut DUNE RESORTS REALTY LLC

    707 Old Montauk Hwy Unit A-57, Montauk, NY 11954
  • 182 Summer St, Portland, CT 06480
    182 Summer St, Portland, CT 06480
    182 Summer St, Portland, CT 06480
    /34

    $274,900

    • 2 Beds
    • 2.5 Baths
    • 1,314 Sq Ft

    182 Summer St, Portland, CT 06480

    Here's an opportunity to "Come on Over" to Portland! Don't miss this move in ready condo 5 minutes off the Arrigoni Bridge with convenience to everything while tucked on a quiet residential street. Summer Meadow provides stress free outdoor maintenance for low fees allowing more time to relax at home. 2 bedrooms each feature full baths, the primary was fully renovated in 2023! Main level features

    Tracy Wagner Rockoff Realty

    182 Summer St, Portland, CT 06480
  • 103 Hillcrest Ave, West Hartford, CT 06110
    103 Hillcrest Ave, West Hartford, CT 06110
    103 Hillcrest Ave, West Hartford, CT 06110
    /11

    $198,000

    • 3 Beds
    • 1.5 Baths
    • 1,071 Sq Ft

    103 Hillcrest Ave, West Hartford, CT 06110

    Experience the best of West Hartford living! This beautifully maintained HALF-DUPLEX offers 3 bedrooms and 1.5 baths. The large, eat-in kitchen is equipped with stainless steel appliances, perfect for everyday meals or entertaining. Hardwood floors flow throughout the home, adding warmth and charm. Enjoy a spacious basement for storage or potential additional living space. Conveniently located

    Eli Joseph eXp Realty

    103 Hillcrest Ave, West Hartford, CT 06110
  • 90 Apple Gate Unit 77, Southington, CT 06489
    90 Apple Gate Unit 77, Southington, CT 06489
    90 Apple Gate Unit 77, Southington, CT 06489
    /25

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,758 Sq Ft

    90 Apple Gate Unit 77, Southington, CT 06489

    Welcome to this beautifully maintained 3 bedroom, 2 bath condo in the highly sought after Apple Gate community, a 55 and over neighborhood known for its peaceful setting and strong sense of community. This spacious unit offers an open floor plan with a bright living room, a well appointed kitchen with plenty of cabinet space, and a dining area perfect for entertaining or quiet evenings at home.

    David Borges The Borges Group LLC

    90 Apple Gate Unit 77, Southington, CT 06489
  • 45 Hart St, Southington, CT 06489
    45 Hart St, Southington, CT 06489
    45 Hart St, Southington, CT 06489
    /25

    $307,900

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    45 Hart St, Southington, CT 06489

    Half-duplex townhouse built in 2001 offering 6 rooms, 3 bedrooms, and 2 full bathrooms across 1,260 square feet. The main level includes a formal dining room and living room with hardwood flooring. The primary bedroom features a walk-in closet. Additional amenities include central air, oil heat, and electric hot water. The one-car garage is located under the unit for added convenience. Vinyl

    Michael Calabro Coldwell Banker Calabro

    45 Hart St, Southington, CT 06489
  • 82 Summer St Unit B, Southington, CT 06489
    82 Summer St Unit B, Southington, CT 06489
    82 Summer St Unit B, Southington, CT 06489
    /24

    $439,900

    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft

    82 Summer St Unit B, Southington, CT 06489

    Beautiful Condo Duplex with no HOA costs. Three story dwelling with lots of room and storage. Great location across from the walking trails and in close vicinity to all Downtown restaurants and shopping. You're greeted with hardwood floors and great floor plan as you enter. Nicely placed living room leads to a full eat-in kitchen with stainless steel appliances & granite counters and a half

    Rebecca Davis Putnam Agency Real Estate LLC

    82 Summer St Unit B, Southington, CT 06489
  • 82 Summer St Unit A, Southington, CT 06489
    82 Summer St Unit A, Southington, CT 06489
    82 Summer St Unit A, Southington, CT 06489
    /24

    $439,900

    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft

    82 Summer St Unit A, Southington, CT 06489

    Beautiful Condo Duplex with no HOA costs. Three story dwelling with lots of room and storage. Great location across from the walking trails and in close vicinity to all Downtown restaurants and shopping. You're greeted with hardwood floors and great floor plan as you enter. Nicely placed living room leads to a full eat-in kitchen with stainless steel appliances & granite counters and a half

    Rebecca Davis Putnam Agency Real Estate LLC

    82 Summer St Unit A, Southington, CT 06489
Connecticut Middlesex County Chester

Townhomes 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

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 $557,500, up 31% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$557,500
Median Single Family Sale Price
$582,000
Average Price Per Sq Ft
$313
Number of Homes for Sale
6
Last 12 months Home Sales
42
Months of Supply
1.70
Median List Price
$640,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
31%
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