1,680

Chester, CT Homes

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  • 131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    /27

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    131 Middlesex Ave, Chester, CT 06412

    Discover this waterfront delight in charming Chester, rewarding with year-round views! Completely renovated in 2012 from the ground up (including brand new septic system), this pristine Colonial offers 3 floors of living space and a smart L-shape open floor plan ensuring that you always have a gorgeous view. In addition to some hardworking 1st floor spaces (roomy mudroom, full bath and laundry

    Agent Photo

    Claudia O'Connell

    William Raveis Real Estate

    (860) 590-3562

    131 Middlesex Ave, Chester, CT 06412
  • 55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    /27

    $2,500 total monthly price

    • 2 Beds
    • 2.5 Baths
    • 1,328 Sq Ft
    • 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 delicious restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an

    Agent Photo

    Janet Cronin-Rumanoff

    William Pitt Sotheby's Int'l

    (860) 730-1941

    55 Liberty St, Chester, CT 06412
  • 16 Hickory Hill Dr, Chester, CT 06412

    $755,000 Sold Nov 19, 2025

    • 1,896 Sq Ft
    • $398/SF
    • 48 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    16 Hickory Hill Dr, Chester, CT 06412

    Welcome to this well maintained 3 Bedroom Cape in the charming town of Chester, just a short distance from downtown. The first floor of this home has an upscaled eat-in kitchen with newer appliances, breakfast bar and granite countertops, a Living/Dining room running front to back, an Office with built-in custom bookshelves and file drawers and a large (17 X 14), inviting Family Room with Propane

    Suzanne McConville William Raveis Real Estate

    16 Hickory Hill Dr, Chester, CT 06412
  • 9 Hickory Hill Dr, Chester, CT 06412
    9 Hickory Hill Dr, Chester, CT 06412
    9 Hickory Hill Dr, Chester, CT 06412
    /40

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    9 Hickory Hill Dr, Chester, CT 06412

    Welcome to 9 Hickory Hill Drive! Set high on a hill in the heart of the charming Connecticut River Village of Chester. This striking Contemporary offers over 2800 sqft. of light-filled living space on 1.23 private acres-just a 3/10 mi stroll to Main St. The inviting foyer opens to a stunning, sun-drenched living area with skylights and gleaming hardwood floors throughout the living room, dining

    Kathy Schellens William Pitt Sotheby's Int'l

    9 Hickory Hill Dr, Chester, CT 06412
  • 42 Bokum Rd Unit 2nd Floor Apartment, Chester, CT 06412
    42 Bokum Rd Unit 2nd Floor Apartment, Chester, CT 06412
    42 Bokum Rd Unit 2nd Floor Apartment, Chester, CT 06412
    /11

    $1,600 total monthly price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    42 Bokum Rd Unit 2nd Floor Apartment, Chester, CT 06412

    2 bedroom 1 bath private entrance with small deck overlooking yard with koi pond, located in a quaint small town with local restaurants, hiking areas, near Rt. 9 for ease of commute, 45 minutes to Hartford, 40 Minutes from New Haven or New London area.

    42 Bokum Rd Unit 2nd Floor Apartment, Chester, CT 06412
  • 21 E Liberty St, Chester, CT 06412

    $252,500 Sold Nov 17, 2025

    • 1,012 Sq Ft
    • $250/SF
    • 26 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1954

    21 E Liberty St, Chester, CT 06412

    Rehab property - CASH only - AS-IS Sale. There is a buried oil tank - seller will not be removing.

    Rachel Welch William Raveis Real Estate

    21 E Liberty St, Chester, CT 06412
  • 35 Maple St, Chester, CT 06412
    35 Maple St, Chester, CT 06412
    35 Maple St, Chester, CT 06412
    /40

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    35 Maple St, Chester, CT 06412

    Steps to the Village! Vintage 1765 Cape with many updates but still true to the original charm of the Joseph Shipman House. Two staircases, 4 working firplaces, King's Board floors, wonderful floorplan and an up-to-date kitchen makes this home a step back in time but with the amenities of today. Quartz countertops and a complete kitchen renovation in 2017. New rear pressure treated deck in 2017.

    Deborah Rowe William Raveis Real Estate

    35 Maple St, Chester, CT 06412
  • 15 Laurel St, Chester, CT 06412
    15 Laurel St, Chester, CT 06412
    15 Laurel St, Chester, CT 06412
    /20

    $2,200 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,366 Sq Ft
    • House for Rent

    15 Laurel St, Chester, CT 06412

    Three-bedroom rental featuring one full bathroom, a private back patio, and an attached one-car garage. The lower level is partially finished, offering additional living or storage space. Located near Cedar Lake, this home includes new double-paned, energy-efficient windows throughout. Credit and background/criminal checks are required with application submission.

    Craig Milton Re/Max Valley Shore

    15 Laurel St, Chester, CT 06412
  • 7 Old Depot Rd, Chester, CT 06412

    $975,000 Sold Nov 17, 2025

    • 3,149 Sq Ft
    • $310/SF
    • 236 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1908

    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
  • 8 Butter Jones Rd, Chester, CT 06412
    8 Butter Jones Rd, Chester, CT 06412
    8 Butter Jones Rd, Chester, CT 06412
    /36

    $775,000

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft

    8 Butter Jones Rd, Chester, CT 06412

    Enchanting Cape with Artisan Post & Beam Charm - Just Down the Road from Chester Village! Tucked away on 2 acres of picturesque land, this whimsical 3-bedroom, 2.5-bath Cape Cod home invites you to live among nature in style. Only a short distance from Cedar Lake and Chester Village, you'll have easy access to endless outdoor adventures and world-class restaurants and shopping just moments away.

    Amy Graham William Pitt Sotheby's Int'l

    8 Butter Jones Rd, Chester, CT 06412
  • 53 Main St Unit A, Deep River, CT 06417
    53 Main St Unit A, Deep River, CT 06417
    53 Main St Unit A, Deep River, CT 06417
    /31

    $2,400 total monthly price

    • 4 Beds
    • 1 Bath
    • 1,462 Sq Ft
    • Condo for Rent

    53 Main St Unit A, Deep River, CT 06417

    This apartment is part of a side by side duplex is available now!Don't miss your chance to rent this beautiful home. Located on Main st, this property is a brisk walk from the center of town. With 4 bedrooms and a spacious backyard, this apartment is perfect for families and renters in need of a lot of personal space.Owner pays for water, trash, and sewer. Renter pays for gas and

    53 Main St Unit A, Deep River, CT 06417
  • 14 Maple St, Chester, CT 06412

    $810,000 Sold Nov 14, 2025

    • 2,322 Sq Ft
    • $349/SF
    • 6 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1755

    14 Maple St, Chester, CT 06412

    Quintessential Chester! This Federal Greek Revival Post and Beam Antique Colonial has been lovingly restored and updated. Mere steps to the Town Center! Taste the true flavor of New England by enjoying this characteristically charming Connecticut Village, well known for its resturants, art galleries, and seasonal events, along with boat marinas and yacht clubs for summer fun. Special features of

    Deborah Rowe William Raveis Real Estate

    14 Maple St, Chester, CT 06412
  • 47 Ferry Rd, Chester, CT 06412
    47 Ferry Rd, Chester, CT 06412
    47 Ferry Rd, Chester, CT 06412
    /40

    $1,095,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,664 Sq Ft

    47 Ferry Rd, Chester, CT 06412

    A unique offering in Chester on the CT. River in the Pattaconk/Fort Hill area, bordering the Chester ferry. A small historic town known for its Main Street, art galleries, restaurants and hiking in the Cockaponset State Forest. Privately situated, fully remodeled charming colonial home sits above the River overlooking 5+ acres of waterfront meadow landscape. Ferry activity, views of Gillette's

    Mary Poola William Raveis Real Estate

    47 Ferry Rd, Chester, CT 06412
  • 159 W Main St Unit E, Chester, CT 06412
    159 W Main St Unit E, Chester, CT 06412
    159 W Main St Unit E, Chester, CT 06412
    /17

    $2,100 total monthly price

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

    159 W Main St Unit E, Chester, CT 06412

    SPACIOUS 2 BEDROOM RANCH APARTMENT WITH NEWLY RENOVATED KITCHEN / LOCATED IN PICTURESQUE MIXED USE BUILDING / FRESHLY PAINTED WITH NEW APPLIANCES, HARDWOOD FLOORS & 9 FOOT CEILINGS / MAIN BEDROOM HAS WALKIN CLOSET / ENJOY HIKING & LIVING NEXT TO "NORTH QUARTER PARK" AND THE CONVENIENCE OF BEAUTIFUL DOWNTOWN CHESTER

    Tom Clancy William Pitt Sotheby's Int'l

    159 W Main St Unit E, Chester, CT 06412
  • 50 Bokum Rd, Chester, CT 06412

    $375,000 Sold Nov 13, 2025

    • 807 Sq Ft
    • $465/SF
    • 59 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1912

    50 Bokum Rd, Chester, CT 06412

    Welcome to this delightful 2-bedroom, 1.5 bath home tucked in the heart of historic Chester, CT. Brimming with character, this cozy home blends modern updates with small-town New England charm. Step inside to find a bright and inviting living space, an updated kitchen, and thoughtful touches throughout. Perfectly sized for easy living, the property offers a low-maintenance yard ideal for

    Cynthia Sigurdson William Pitt Sotheby's Int'l

    50 Bokum Rd, Chester, CT 06412
  • 13 Cross Rd, Chester, CT 06412
    13 Cross Rd, Chester, CT 06412
    13 Cross Rd, Chester, CT 06412
    /40

    $629,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,324 Sq Ft

    13 Cross Rd, Chester, CT 06412

    Set on a private 4.48-acre lot, this inviting Colonial offers over 2,300 sq. ft. of comfortable living space with 8 spacious rooms, including 3 bedrooms. The welcoming family room features a fireplace, built-ins, soaring cathedral ceilings, a large skylight, and sliders leading to the rear deck, filling the home with natural light. Enjoy the tranquility and privacy of the setting while still

    Curtiss Clemens Jr. Century 21 Clemens Group

    13 Cross Rd, Chester, CT 06412
  • 15 Liberty St, Chester, CT 06412
    15 Liberty St, Chester, CT 06412
    15 Liberty St, Chester, CT 06412
    /39

    $7,500 total monthly price

    • 4 Beds
    • 4.5 Baths
    • 4,708 Sq Ft
    • House for Rent

    15 Liberty St, Chester, CT 06412

    Exceptional Rental Opportunity in Chester's Quintessential New England Village. Experience refined living in this estate-like setting, exquisitely furnished and thoughtfully remodeled to the highest standards. Offering over 4,000 sq. ft. of light-filled luxury, this stunning home is available October 2025 through mid-May 2026. Property Highlights: 4 Bedrooms | 5 Baths - including an

    Lynn Lehrman Re/Max Valley Shore

    15 Liberty St, Chester, CT 06412
  • 28 Hoop Pole Hill Rd, Chester, CT 06412

    $760,000 Sold Nov 03, 2025

    • 3,396 Sq Ft
    • $224/SF
    • 83 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2008

    28 Hoop Pole Hill Rd, Chester, CT 06412

    Discover the perfect blend of elegance and convenience in this custom Cape Cod home, nestled privately in Chester, CT. Boasting 4 bedrooms and 3.5 baths, this residence is convenient to the vibrant downtown area and easily accessible to the highway, yet set in a quiet woodland sanctuary, directly across from over 100 acres of state forest and trails. With timeless decor that exudes classic charm,

    Teri Lewis William Pitt Sotheby's Int'l

    28 Hoop Pole Hill Rd, Chester, CT 06412
  • 28 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    /40

    $625,000 Under Contract

    • 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
  • 30 Bokum Rd, Chester, CT 06412

    $442,500 Sold Oct 20, 2025

    • 1,198 Sq Ft
    • $369/SF
    • 59 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    30 Bokum Rd, Chester, CT 06412

    Enjoy the perfect blend of small-town charm and everyday comfort in this inviting Cape, ideally located just a few minutes from Chester center. The home features 3 bedrooms upstairs, each with unique charm and natural light, plus 2 full baths-one on the main floor with a sleek walk-in shower and one upstairs with a tub/shower combo. Gleaming hardwood floors run throughout the main living areas,

    Max Gill Puorro Realty Group

    30 Bokum Rd, Chester, CT 06412
  • 12 Deep Hollow Rd, Chester, CT 06412
    12 Deep Hollow Rd, Chester, CT 06412
    12 Deep Hollow Rd, Chester, CT 06412
    /16

    $319,900

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft

    12 Deep Hollow Rd, Chester, CT 06412

    Enjoy convenient one level living on a quiet, charming dead-end street just steps from Chester Village. This home offers a full unfinished walkout basement, vinyl siding, thermal windows, and a 200-amp electrical panel. A new furnace was installed in 2019. The neighborhood is truly exceptional, residents are unbelievably kind and feel like family. With a little TLC, this property is ready for

    Craig Milton Re/Max Valley Shore

    12 Deep Hollow Rd, Chester, CT 06412
  • 95 Cedar Swamp Rd, Chester, CT 06412

    $1,017,000 Sold Oct 20, 2025

    • 4,341 Sq Ft
    • $234/SF
    • 53 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    95 Cedar Swamp Rd, Chester, CT 06412

    Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester. Bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning views over Shailer Pond, this home brings the outdoors in from every angle.

    Rachel Welch William Raveis Real Estate

    95 Cedar Swamp Rd, Chester, CT 06412
  • 79 Middlesex Ave, Chester, CT 06412
    79 Middlesex Ave, Chester, CT 06412
    79 Middlesex Ave, Chester, CT 06412
    /32

    $449,000

    • 2 Beds
    • 1 Bath
    • 1,470 Sq Ft

    79 Middlesex Ave, Chester, CT 06412

    Charming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends timeless New England character with everyday comfort and walk-to-village convenience. Warm hardwood floors flow throughout the light-filled living room into the updated kitchen with its beautiful bow window and dining area. The kitchen is replete with ample granite counters, perfect for the aspiring chef! The

    Gigi Giordano Taylor Compass Connecticut, LLC

    79 Middlesex Ave, Chester, CT 06412
  • 23 Spring St, Chester, CT 06412

    $550,000 Sold Oct 15, 2025

    • 1,104 Sq Ft
    • $498/SF
    • 15 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1920

    23 Spring St, Chester, CT 06412

    This precious 1920 bungalow has had only 2 owners! It has been updated and extremely well cared for. Central a/c, 2 bedrooms, 1 1/2 baths, full basement, and the most perfect front porch to sit and watch the world go by. A fabulous two-story barn/garage with a full loft and wonderful lawn and garden area. Peaceful, private and quiet but just a short stroll to Main Street Chester with shops,

    Susan Malan William Pitt Sotheby's Int'l

    23 Spring St, Chester, CT 06412
  • 6 W Main St, Chester, CT 06412
    6 W Main St, Chester, CT 06412
    6 W Main St, Chester, CT 06412
    /37

    $725,000

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft

    6 W Main St, Chester, CT 06412

    EXCELLENT LOCATION, EXCELLENT CONDITION! Lovingly restored 2-family in the heart of Chester Village with historic provenance. Perfect blend of old-school New England charm and modern updates including new siding, full insulation, and A/C. PRIME VILLAGE LOCATION - walk to Chester's vibrant fairs, events, dining, and shopping. Easy commute to Rt. 9. BOTH UNITS FEATURE: * 2 bedrooms with original

    MJ Derisio William Pitt Sotheby's Int'l

    6 W Main St, Chester, CT 06412
  • 14 Ferry Rd, Chester, CT 06412

    $420,000 Sold Sep 24, 2025

    • 2,025 Sq Ft
    • $207/SF
    • 35 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1950

    14 Ferry Rd, Chester, CT 06412

    Located by the Chester-Hadlyme Ferry, this 4 bedroom, 1.5 bath home is waiting your customization. Built in 1950, this home has original wainscoting in the living room, hardwood floors and built-in cabinets throughout. A large family room with fireplace is the perfect location to enjoy a cold winter night. There are three bedrooms on the main floor and a fourth on the second floor, which is

    Ian Sacks Coldwell Banker Realty

    14 Ferry Rd, Chester, CT 06412
  • 60 Goose Hill Rd, Chester, CT 06412
    60 Goose Hill Rd, Chester, CT 06412
    60 Goose Hill Rd, Chester, CT 06412
    /36

    $849,900

    • 7 Beds
    • 2 Baths
    • 2,402 Sq Ft

    60 Goose Hill Rd, Chester, CT 06412

    Spectacular 2 Family home newly renovated. Separate entrances and separate driveways. One unit has 4 bedrooms and a bonus room and the other has 3 bedrooms. New septic system. Central air and washer/dryer hookups in each unit. Huge open kitchen/dining/living room area in both units. All wood and tile floors. Even the basement looks new with all new mechanicals. Stone wall along the driveway

    Alexis Devlin Coldwell Banker Realty

    60 Goose Hill Rd, Chester, CT 06412
  • 25 Spring St, Chester, CT 06412

    $860,000 Sold Sep 17, 2025

    • 2,344 Sq Ft
    • $367/SF
    • 38 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1860

    25 Spring St, Chester, CT 06412

    Tucked away on Spring Street in the heart of Chester village, this stately two-story residence gracefully combines classic farmhouse tradition with all the amenities of modern living. As you enter the home through the foyer, sunlight pours through generous windows, illuminating the living room anchored by an elegant fireplace. Recessed lighting and gleaming wide-plank wood floors lend an

    Susan Malan William Pitt Sotheby's Int'l

    25 Spring St, Chester, CT 06412
  • 288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    /40

    $3,375,000

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

    288 Middlesex Ave, Chester, CT 06412

    East View is a long-admired Connecticut Riverfront property, a rare offering that perfectly marries historic provenance with elevated modern living. The circa 1800 home was masterfully renovated and expanded in 2010 with an architect's eye and a reverence for its storied past. Meticulous attention to detail is found in the extensive millwork, custom built-ins and hand-hewn beams lending warmth

    Nancy Mesham Coldwell Banker Realty

    288 Middlesex Ave, Chester, CT 06412

Showing Results 1 - 40, Page 1 of 18

Connecticut Middlesex County Chester

Real Estate & Homes

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 52 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, CT over the last 12 months is $637,500, up 54% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$637,500
Median Single Family Sale Price
$644,500
Average Price Per Sq Ft
$339
Number of Homes for Sale
7
Last 12 months Home Sales
41
Months of Supply
2.00
Median List Price
$649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
54%
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