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Recently Sold Chester, CT Homes

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  • 25 Gilbert Hill Rd, Chester, CT 06412

    $1,135,000 Sold Jun 30, 2025

    • 3,351 Sq Ft
    • $339/SF
    • 16 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1987

    25 Gilbert Hill Rd, Chester, CT 06412

    Experience the stunning views of the Connecticut River, Lyme's hills, and the expansive valley from your heated Gunite in-ground swimming pool. The beautifully manicured grounds reflect years of dedicated care. This home showcases exceptional quality, featuring customized designs and meticulous details throughout, including custom moldings and cabinetry in the kitchen, bathrooms, and closets.

    Robin Linares William Pitt Sotheby's Int'l

    25 Gilbert Hill Rd, Chester, CT 06412
  • 15 Gilbert Hill Rd, Chester, CT 06412

    $1,000,050 Sold Jun 25, 2025

    • 3,054 Sq Ft
    • $327/SF
    • 18 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1950

    15 Gilbert Hill Rd, Chester, CT 06412

    Mid-Century Modern Private Compound Overlooking the CT River Valley. Discover this exceptional mid-century modern retreat, a private compound set in a park-like setting with distant water views of the Connecticut River Valley. This expanded Cape blends timeless design with modern updates, featuring an open floor plan flooded with natural light from skylights, two fireplaces, and hand-laid terra

    Angela Ruel Berkshire Hathaway NE Prop.

    15 Gilbert Hill Rd, Chester, CT 06412
  • 31 Parkers Point Rd, Chester, CT 06412

    $3,100,000 Sold Jun 10, 2025

    • 4,727 Sq Ft
    • $656/SF
    • 27 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2010

    31 Parkers Point Rd, Chester, CT 06412

    Nestled near the heart of the quaint Chester Village, this exquisite Nantucket-style home offers a serene retreat on the banks of the CT River. Spanning an impressive 4,727sqft, this architectural gem is all enveloped in traditional shingle elegance. As you step inside, you're welcomed by a two-story, paneled living room that exudes drama and sophistication. The space is adorned with beautiful

    Colette Harron William Pitt Sotheby's Int'l

    31 Parkers Point Rd, Chester, CT 06412
  • 67 Maple St, Chester, CT 06412

    $575,000 Sold May 29, 2025

    • 1,803 Sq Ft
    • $319/SF
    • 44 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    67 Maple St, Chester, CT 06412

    Welcome to this delightful meticulous Cape Cod home, featuring 3 spacious bedrooms, 2.5 baths and a home office. The primary bedroom suite is generous in size with his and her closets, a jacuzzi tub in the primary bathroom and is conveniently located on the first floor. The main level also includes a dedicated home office that has access to the beautiful, huge trex deck. The kitchen has been

    Laura Cariati Coldwell Banker Realty

    67 Maple St, Chester, CT 06412
  • 42 W Main St, Chester, CT 06412

    $651,500 Sold May 16, 2025

    • 1,766 Sq Ft
    • $369/SF
    • 35 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1925

    42 W Main St, Chester, CT 06412

    This newly renovated century-old bungalow home offers a harmonious blend of historic charm and modern amenities. The expansive front porch provides an ideal setting for enjoying morning coffee or evening beverages while appreciating the outdoors. The entirely new kitchen features quartz countertops and a marble backsplash, with ample natural light illuminating the space. An adjacent pantry

    Pardi & Zucco Team William Pitt Sotheby's Int'l

    42 W Main St, Chester, CT 06412
  • 24 E Liberty St, Chester, CT 06412

    $450,000 Sold May 14, 2025

    • 1,926 Sq Ft
    • $234/SF
    • 13 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1790

    24 E Liberty St, Chester, CT 06412

    Step back into Chester history! This home sits on over an acre within the town limits of Chester. It's sits on a quiet street with an expansive back yard. Much of structure has the historical details that antique home enthusiasts look for: wide plank chestnut floors, hand forged hardware, exposed beams, stone fireplaces, etc. Practicality also exists with the main house having higher ceilings

    Bonnie Fillion Berkshire Hathaway NE Prop.

    24 E Liberty St, Chester, CT 06412
  • 93 W Main St, Chester, CT 06412

    $180,000 Sold May 09, 2025

    • 752 Sq Ft
    • $239/SF
    • 32 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1955

    93 W Main St, Chester, CT 06412

    Charming One-Bedroom Ranch in Chester Village - A Hidden Gem! Discover the perfect investment opportunity with this delightful one-bedroom ranch located within walking distance to the picturesque downtown Chester Village. Known for its charming ambiance, this quaint town serves as a backdrop for Hallmark movies, offering a delightful mix of fantastic restaurants, unique galleries, and boutique

    Kelly Puorro Puorro Realty Group

    93 W Main St, Chester, CT 06412
  • 16 Waterhouse Ln, Chester, CT 06412

    $1,250,000 Sold May 02, 2025

    • 4,661 Sq Ft
    • $268/SF
    • 24 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1988

    16 Waterhouse Ln, Chester, CT 06412

    Discover the essence of elegance and tranquility in this exquisite Chester estate, boasting a host of 2024 upgrades including a new roof, furnace, and a tastefully renovated half bath. This property also comes with an approved separate building lot, enhancing your privacy and offering potential investment opportunities. The home is perfectly oriented to capture the morning sunrises, providing

    Teri Strain-Lewis William Pitt Sotheby's Int'l

    16 Waterhouse Ln, Chester, CT 06412
  • 108 Middlesex Ave, Chester, CT 06412

    $675,000 Sold May 01, 2025

    • 4,056 Sq Ft
    • $166/SF
    • 65 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2002

    108 Middlesex Ave, Chester, CT 06412

    Welcome to 108 Middlesex Ave. A multi family Colonial income producing property in the heart of Chester! The home was built in 2002, and in 2006 an attached accessory dwelling unit / inlaw apartment was added and is now occupied at $2,000 a month. The main house features a bright and inviting layout with hardwood floors, a cozy fireplace in the living room and sliders from the dining room out to

    Trever Smith Chiarito Real Estate LLC

    108 Middlesex Ave, Chester, CT 06412
  • 6 Old County Rd, Chester, CT 06412

    $975,000 Sold Apr 30, 2025

    • 2,680 Sq Ft
    • $364/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2002

    6 Old County Rd, Chester, CT 06412

    Private, pristine, and with proximity to the Connecticut River, many wonderful restaurants, and boutiques. This meticulously maintained four bedroom 2 1/2 bath home is less than 2 miles from fabulous Chester Village. Set on over 2 acres this beautiful home has been carefully updated and enhanced. The meandering driveway takes you to a perfectly sited home with an amazing heated barn which also

    Susan Malan William Pitt Sotheby's Int'l

    6 Old County Rd, Chester, CT 06412
  • 19 W Main St, Chester, CT 06412

    $1,363,500 Sold Apr 15, 2025

    • 4,205 Sq Ft
    • $324/SF
    • 136 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    19 W Main St, Chester, CT 06412

    Welcome to the Waterfall House, an iconic custom home perched above the scenic Pattaconk Brook in the heart of historic Chester Village. Overlooking a picturesque 15-foot waterfall and offering sweeping views of the serene Jennings Pond from every room, this home is a masterpiece. Meticulously renovated in 2021, it blends modern luxury with timeless historic charm. Just a 5-minute stroll from

    Michael Marsden Compass Connecticut, LLC

    19 W Main St, Chester, CT 06412
  • 14 Straits Rd, Chester, CT 06412

    $285,000 Sold Apr 09, 2025

    • 1,519 Sq Ft
    • $188/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1702

    14 Straits Rd, Chester, CT 06412

    **Incredible Opportunity Awaits!** Discover the potential of this charming three-bedroom colonial, ideally situated in the heart of Chester Village. With a new septic system, roof, and windows already installed, the groundwork is laid for your dream home. The interior is completely gutted down to the studs, offering a blank canvas for a full rehab or the perfect opportunity to build your own

    Kelly Puorro Puorro Realty Group

    14 Straits Rd, Chester, CT 06412
  • 11 Bishop Rd, Chester, CT 06412

    $350,000 Sold Apr 07, 2025

    • 1,188 Sq Ft
    • $295/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1964

    11 Bishop Rd, Chester, CT 06412

    Enjoy one-level living with protected year -round views of Cedar Lake in this 2-3 bedroom ranch. The smaller bedroom features convenient laundry access. A spacious living room with a fireplace and bay window offers a perfect spot to take in the scenic view. The home boasts hardwood floors throughout. The full basement is partially finished and offers plenty of potential. Located next to

    Craig Milton Re/Max Valley Shore

    11 Bishop Rd, Chester, CT 06412
  • 10 Old County Rd, Chester, CT 06412

    $900,000 Sold Mar 24, 2025

    • 2,755 Sq Ft
    • $327/SF
    • 26 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1998

    10 Old County Rd, Chester, CT 06412

    Private and peaceful with seasonal views of the Connecticut River yet less than two miles to fabulous Chester Village with shops, restaurants, art galleries, spectacular (in season) farmers market and more. This 4-bedroom custom built home has a wonderful floor plan consisting of 4 bedrooms, 3 1/2 baths, 9' ceilings, huge primary bedroom with cathedral ceilings, oversized ensuite full bath and

    Susan Malan William Pitt Sotheby's Int'l

    10 Old County Rd, Chester, CT 06412
  • 71 Maple St, Chester, CT 06412

    $540,000 Sold Mar 20, 2025

    • 2,144 Sq Ft
    • $252/SF
    • 172 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1980

    71 Maple St, Chester, CT 06412

    Close to the town center, yet on a two acre tree shaded lot set back from the street. Gambrel colonial with a two car attached garage and three car detached garage. Garden area with in-ground pool feature. Possible in-law apartment on first floor. Furnace is oil with optional wood burning capability. Living room fireplace has a wood burning stove. New washer and dryer. Newer septic tank. Wide

    Louisa Ketron Berkshire Hathaway NE Prop.

    71 Maple St, Chester, CT 06412
  • 15 Kirtland Terrace, Chester, CT 06412

    $280,000 Sold Mar 07, 2025

    • 1,170 Sq Ft
    • $239/SF
    • 3 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1951

    15 Kirtland Terrace, Chester, CT 06412

    Nestled at the end of a quiet street, this 3-bedroom, 1.5-bath ranch offers a rare chance to create your dream home in historic Chester. Overlooking the serene Chester Fairgrounds fields, this property features stunning views and a spacious lot, making it ideal for renovation or a fresh new build. With easy one-floor living and central air, this home offers comfort and convenience. Whether you

    Kristina Quinones William Pitt Sotheby's Int'l

    15 Kirtland Terrace, Chester, CT 06412
  • 261 Middlesex Ave, Chester, CT 06412

    $360,000 Sold Feb 25, 2025

    • 1,248 Sq Ft
    • $288/SF
    • 36 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1935

    261 Middlesex Ave, Chester, CT 06412

    Come & enjoy all that Chester has to offer! Chester is one of the most sought after Connecticut village towns! This sweet Colonial built in 1935 is set back from the road on 2 picturesque acres of land offering plenty of expansion possibilities! Family owned since 1935. First floor offers a living room with stone fireplace, a dining room, a kitchen & mud room. All original hardwood floors

    Theresa Bitondo Berkshire Hathaway NE Prop.

    261 Middlesex Ave, Chester, CT 06412
  • 67 W Main St, Chester, CT 06412

    $637,500 Sold Jan 31, 2025

    • 1,916 Sq Ft
    • $333/SF
    • 8 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1917

    67 W Main St, Chester, CT 06412

    Chester Village...a home you will love! Designed with natural grace and style, the timeless simplicity of this Quintessential New England Arts & Crafts style home offers the perfect blend of traditional architectural features with modern home design. Lovingly restored by the current owners, a welcoming front porch leads to a gracious entryway and elegant well-proportioned rooms that blend

    Kyle Hinding Coldwell Banker Realty

    67 W Main St, Chester, CT 06412
  • 96 Middlesex Ave, Chester, CT 06412

    $1,300,000 Sold Jan 31, 2025

    • 3,153 Sq Ft
    • $412/SF
    • 162 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1830

    96 Middlesex Ave, Chester, CT 06412

    Steeped in history, awash in modern amenities and conveniences, this 4 bed (2 en suite), 3 1/2 bath converted barn sits on over six acres just a spit from the Connecticut River and the quintessential town of Chester. The current homeowner's goal was to gently nudge the 1830s cider mill into this century with thought, care, and charm salvaging and repurposing as many original features as feasible.

    Susan Malan William Pitt Sotheby's Int'l

    96 Middlesex Ave, Chester, CT 06412
  • 2 Sypher Rd, Chester, CT 06412

    $450,000 Sold Jan 24, 2025

    • 2,278 Sq Ft
    • $198/SF
    • 66 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1970

    2 Sypher Rd, Chester, CT 06412

    Welcome to 2 Sypher Rd. Chester! Tucked away in the peaceful woods of Chester near Cedar Lake, this charming 2,278 sq ft, 4-bedroom, 2.5-bath colonial rests on a picturesque 2-acre lot. Inside, you'll find hardwood floors throughout and a beautifully remodeled kitchen with soft-close cabinets, Corian countertops, and stainless steel appliances. The spacious living room, complete with a cozy

    Stacey Wyeth William Pitt Sotheby's Int'l

    2 Sypher Rd, Chester, CT 06412
  • 5 Marina View Dr, Chester, CT 06412

    $500,000 Sold Jan 17, 2025

    • 2,037 Sq Ft
    • $245/SF
    • 81 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1993

    5 Marina View Dr, Chester, CT 06412

    Rare opportunity - one owner home! Lovely contemporary Cape Cod with open floor plan, updated kitchen, fanstastic family room with an expansive deck, and 3 bedrooms and 3 1/2 baths. Situated at the end of a cul de sac and with over 11 acres of privacy and just a stroll to The Anchor and Marker 37 restaurants and Hays Haven and Chester Point marinas.

    Susan Malan William Pitt Sotheby's Int'l

    5 Marina View Dr, Chester, CT 06412
  • 39 Castle View Dr, Chester, CT 06412

    $419,900 Sold Jan 07, 2025

    • 2,208 Sq Ft
    • $190/SF
    • 95 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2013

    39 Castle View Dr, Chester, CT 06412

    Nestled along the picturesque Connecticut River, minutes from the village of Chester, this 3 bedroom, 3.5 bath colonial home offers an exceptional opportunity. The open-concept living space seamlessly blends the kitchen and living room. The kitchen boasts an abundance of cabinetry, sleek granite countertops, and stainless steel appliances, complemented by a spacious center island. Open living

    Gene Pica RE/MAX Alliance

    39 Castle View Dr, Chester, CT 06412
  • 56 Castle View Dr, Chester, CT 06412

    $430,000 Sold Nov 27, 2024

    • 2,268 Sq Ft
    • $190/SF
    • 40 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1963

    56 Castle View Dr, Chester, CT 06412

    Welcome to your dream home! This home features an open floor plan that seamlessly connects living spaces, perfect for both entertaining and everyday living, cozy front porch, perfect for relaxing and enjoying your morning cup of coffee, spacious 2nd floor primary bedroom suite with full bathroom and walk in closet, 4 generous sized bedrooms all with large closets. Enjoy the beauty of hardwood

    Sharon Linder Berkshire Hathaway NE Prop.

    56 Castle View Dr, Chester, CT 06412
  • 28 Goose Hill Rd, Chester, CT 06412

    $582,000 Sold Nov 21, 2024

    • 2,398 Sq Ft
    • $243/SF
    • 5 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1870

    28 Goose Hill Rd, Chester, CT 06412

    Step into history with this 1870 colonial home on over 1.5 acres. Featuring three bedrooms and two fully finished bathrooms, plus a third en suite awaiting your touch, this property is a canvas for your creativity. Enjoy high ceilings on the first floor, bathed in natural light from large windows that create a warm and inviting atmosphere. Relax on the front porch or in the screened-in back

    Cheryl Bergeron-Lucca LPT Realty - IConn Team

    28 Goose Hill Rd, Chester, CT 06412
  • 11 Laurel St, Chester, CT 06412

    $189,900 Sold Nov 08, 2024

    • 616 Sq Ft
    • $308/SF
    • 48 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1946

    11 Laurel St, Chester, CT 06412

    Seasonal 2 bedroom Cottage. Large Lot. Potential for year round conversion. Or simply update it for your own summer getaway!

    Craig Milton Re/Max Valley Shore

    11 Laurel St, Chester, CT 06412
  • 4 Bates Rd, Chester, CT 06412

    $276,000 Sold Oct 30, 2024

    • 1,200 Sq Ft
    • $230/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1950

    4 Bates Rd, Chester, CT 06412

    This classic ranch sits on a dead end street, close to downtown and less than a minute from the local elementary school. This home has an easy, useable floor plan and a private backyard on a road of similar homes. Original kitchen and simple fixtures throughout, the home does have central air and nothing but upside potential. This is an as-is sale. Note, the roof is not insurable and showing

    Cara Bernard Coldwell Banker Realty

    4 Bates Rd, Chester, CT 06412
  • 187 Middlesex Ave, Chester, CT 06412

    $225,000 Sold Oct 25, 2024

    • 1,194 Sq Ft
    • $188/SF
    • 58 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1965

    187 Middlesex Ave, Chester, CT 06412

    Come enjoy all Chester has to offer. Make this 3 bedroom 1 bathroom house your home. Town has a vibrant community and offers many amenities such as quaint shops, amazing restaurants, parks and is conveniently located between New York and Boston. Insured w/ Escrow(IE). FHA Case #061-400225. Eligible Bidders: Owner Occupants, Nonprofits,and Government Agencies only

    Team DAnna Statewide Premier Prop. LLC

    187 Middlesex Ave, Chester, CT 06412
  • 41 Railroad Ave, Chester, CT 06412

    $390,000 Sold Oct 24, 2024

    • 1,771 Sq Ft
    • $220/SF
    • 46 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1952

    41 Railroad Ave, Chester, CT 06412

    This lovely Chester Cape is just the house you have been waiting for. A modern kitchen with beautiful granite countertops and newer Stainless appliances make preparing the days meals a pleasure. A cozy living room complete with a fireplace for chilly nights along with very nice, updated bathroom are just a few of the wonderful features found throughout this home. With two bedrooms downstairs

    Philip Warner William Pitt Sotheby's Int'l

    41 Railroad Ave, Chester, CT 06412
  • 142 Main St, Chester, CT 06412

    $537,000 Sold Oct 11, 2024

    • 2,188 Sq Ft
    • $245/SF
    • 58 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1952

    142 Main St, Chester, CT 06412

    Longing to live within walking distance to Chester Village? Look no further than this unique custom built stone home within walking distance to highly desirable Chester Village where people come to enjoy the dining, shopping & art galleries. Also close to North Quarter Park in Chester. This Gem built by Martin Lanzi is available for the 1st time in 72 years! The home features a gorgeous grey

    Theresa Bitondo Berkshire Hathaway NE Prop.

    142 Main St, Chester, CT 06412
  • 9 Gilbert Hill Rd, Chester, CT 06412

    $400,000 Sold Oct 09, 2024

    • 2,008 Sq Ft
    • $199/SF
    • 60 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1971

    9 Gilbert Hill Rd, Chester, CT 06412

    Great location just outside of Chester Village on a quiet cul de sac street. Main level features a living room with hardwood floors, kitchen with hardwood floors, large family room with gas fireplace and a screened in patio. Upper level has a large master bedroom with walk in closet and a balcony overlooking the back yard, a bedroom, office and laundry area. This home needs some cosmetics and

    Shane Bonanno Coldwell Banker Realty

    9 Gilbert Hill Rd, Chester, CT 06412
  • 68 W Main St, Chester, CT 06412

    $730,000 Sold Oct 02, 2024

    • 3,518 Sq Ft
    • $208/SF
    • 102 Days On Market
    • 6 Beds
    • 1.5 Baths
    • Built 1892

    68 W Main St, Chester, CT 06412

    This iconic Chester home, built by George Smith began as a single farmhouse in 1874 as the property of Samuel Gledhill. In 1883, the property was sold to Wilbur Brothwell, the son of a woodworker who worked for P.T. Barnum. Brothwell is responsible for many of the home's unique features such as the third-floor tower and the beautifully preserved dark wood interiors. You can see his safe still

    Marissa McCue William Pitt Sotheby's Int'l

    68 W Main St, Chester, CT 06412
  • 230 W Main St, Chester, CT 06412

    $405,000 Sold Sep 30, 2024

    • 1,530 Sq Ft
    • $265/SF
    • 24 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1986

    230 W Main St, Chester, CT 06412

    New England charm abounds in this wonderful home just steps from Cedar Lake and Cockaponset State Forest! NEW ROOF (2023) and new windows (2022)! Step inside to the open and bright living room with soaring ceiling, wide board wood floors and beautiful stone fireplace and the dining room perfect for entertaining. The kitchen overlooks the living room and features granite counters and stainless

    Siobhan McLaughlin William Raveis Real Estate

    230 W Main St, Chester, CT 06412
  • 42 Railroad Ave, Chester, CT 06412

    $460,000 Sold Sep 26, 2024

    • 2,092 Sq Ft
    • $220/SF
    • 117 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1954

    42 Railroad Ave, Chester, CT 06412

    BEST DEAL IN TOWN! RARE FIND, FULLY RENOVATED 2 FAMILY HOME LOCATED A SHORT DISTANCE TO DOWNTOWN CHESTER, DOWNTOWN DEEP RIVER AND LOCAL MARINA. GLEAMING HARDWOOD FLOORS THROUGHOUT, GRANITE COUNTERTOPS IN BOTH KITCHENS, TWO FULL BATHS, NEW HVAC SYSTEM, NEW ROOF, NEW WINDOWS, NEW ELECTRICAL. LARGE FAMILY ROOM, THREE SEASON ROOM AND TWO CAR DETACHED GARAGE. NEW SEPTIC SYSTEM AS WELL! LOTS OF

    George Sznaj DB Associates of CT, LLC

    42 Railroad Ave, Chester, CT 06412
  • 103 Goose Hill Rd, Chester, CT 06412

    $400,000 Sold Sep 25, 2024

    • 1,560 Sq Ft
    • $256/SF
    • 12 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1925

    103 Goose Hill Rd, Chester, CT 06412

    Experience the enchantment of quiet country living with this quintessential vintage farmhouse in Chester, Connecticut. Nestled on a tranquil 2.04-acre plot, this home offers a warm embrace of rustic charm and modern conveniences. Inside you will find an flexible floor plan ready for your creative updates, including three generously sized bedrooms, a full bath, and a half bath. The expansive

    Amy Graham William Pitt Sotheby's Int'l

    103 Goose Hill Rd, Chester, CT 06412
  • 35 -16 Castle View Dr, Chester, CT 06412

    $1,325,000 Sold Sep 06, 2024

    • 2,006 Sq Ft
    • $661/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1996

    35 -16 Castle View Dr, Chester, CT 06412

    WATERFRONT-NEW PRICE-Directly situated on the CT River, this 1.04 acre, 3 bedroom home with private dock and private viewing/seating area offers tranquility and stunning views. Updated/remodeled in 2017, this home offers an open floor plan with exquisite architectural details. Craftsmanship abounds showcasing custom millwork, wide plank wood flooring, wood beams and crown molding throughout.

    Sandra Manafort Silver and Oak Realty

    35 -16 Castle View Dr, Chester, CT 06412
  • 9 Old County Rd, Chester, CT 06412

    $842,000 Sold Aug 19, 2024

    • 4,361 Sq Ft
    • $193/SF
    • 64 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1998

    9 Old County Rd, Chester, CT 06412

    Welcome to 9 Old County Road in picturesque Chester. This 4 bedroom, 3.5 bath home is nestled atop a quiet 5 home cul-de-sac. You will fall in love as you pull into the driveway, admire the perfect balance of privacy and community. A newer front door with transom and sidelites welcomes you and warms the entryway with light. The main floor offers both living room and family room, a formal dining

    Sacha Armstrong William Pitt Sotheby's Int'l

    9 Old County Rd, Chester, CT 06412
  • 25 Spring St, Chester, CT 06412

    $695,000 Sold Jul 31, 2024

    • 2,164 Sq Ft
    • $321/SF
    • 1 Day On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1860

    25 Spring St, Chester, CT 06412

    This charming two-story Chester home offers a perfect blend of modern comfort and farmhouse character. Boasting 3 bedrooms and 2.5 bathrooms, this meticulously maintained property spans 2,344 square feet of living space. Upon entering, you are greeted by a spacious living room that opens to the back of the home giving natural light throughout the day. The living room boasts a fireplace, recessed

    Bonnie Fillion Berkshire Hathaway NE Prop.

    25 Spring St, Chester, CT 06412
  • 40 Gilbert Hill Rd, Chester, CT 06412

    $562,000 Sold Jul 31, 2024

    • 1,395 Sq Ft
    • $403/SF
    • 6 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1998

    40 Gilbert Hill Rd, Chester, CT 06412

    Renovated, one-floor living. This breezy, bright home lends itself to easy, one-floor living.... whether it's the vaulted ceilings or the open (white) kitchen that draws you in... there's a lot to see in this special home. This house is nestled at the end of a dead end street, moments to the village of Chester. Live all on one floor with two sizeable bedrooms and two baths or enjoy the finished

    Cara Bernard Coldwell Banker Realty

    40 Gilbert Hill Rd, Chester, CT 06412
  • 8 Bokum Rd, Chester, CT 06412

    $405,000 Sold Jul 31, 2024

    • 1,738 Sq Ft
    • $233/SF
    • 7 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1859

    8 Bokum Rd, Chester, CT 06412

    Located in this picturesque Town of Chester, known for its historical charm. This property is less than a mile away from downtown Chester! Near Chester Library and Route 9. This beautifully landscaped property and nestled on the hillside welcomes you to a quaint stone path leading up to this charming house. The first floor features a large living room that has been extended out. Skylights were

    Kimberly McHugh Puorro Realty Group

    8 Bokum Rd, Chester, CT 06412
  • 45 Winthrop Rd, Chester, CT 06412

    $419,000 Sold Jul 30, 2024

    • 1,972 Sq Ft
    • $212/SF
    • 60 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1985

    45 Winthrop Rd, Chester, CT 06412

    Discover your new sanctuary at 45 Winthrop Road, where comfort and charm meet in a lovely, picturesque location. Just minutes from Cedar Lake and Cockaponset State Forest which offers great swimming, hiking, and kayaking/canoeing. This charming Cape was built in 1985 and boasts 4 bedrooms and 3 full baths, situated on a serene level 2.12-acre lot. As you enter, the breezeway welcomes

    Kira Coon William Raveis Real Estate

    45 Winthrop Rd, Chester, CT 06412

Showing Results 1 - 40, Page 1 of 2

Connecticut Chester

Recently Sold Real Estate & Homes in Chester, CT

Frequently Asked Questions

What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $684,316.
What is the average time to sell a house in Chester, CT?
The houses for sale in Chester, CT spend an average of 49 days on the market.
What is the number of active homes for sale in Chester, CT?
There are 3 active homes for sale in Chester, CT.
How many homes have sold over the last 12 months in Chester, CT?
41 homes have sold in Chester, CT over the last 12 months.

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 49 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, CT over the last 12 months is $537,000, up 22% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$537,000
Median Single Family Sale Price
$518,500
Average Price Per Sq Ft
$303
Number of Homes for Sale
3
Last 12 months Home Sales
41
Months of Supply
0.90
Median List Price
$522,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
22%
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