An extraordinary offering in one of Connecticut's most beloved river towns. Stunning sunrises over unobstructed views of Chester Creek sets the tone for this rare piece of Chester history. The Bani Denison homestead dates to 1781 and once served as Chester's first post office. Thoughtfully restored, this classic embankment Colonial with Dutch kick gambrel style roof offers modern amenities while preserving exceptional period detail throughout. Original wide-board chestnut floors and wall panels, six fireplaces (five working and wood-burning), original mantels and millwork, and two stairways, including the captain's staircase in the front foyer, define the home's character. The spacious primary bedroom features a barrel ceiling, fireplace and remodeled en-suite bath. A newly renovated kitchen blends seamlessly with the home's historic charm, while the finished lower level provides flexible space for a home office/studio/guest space with private entry. The home is filled with natural light throughout the day, the established backyard gardens providing privacy, and a seasonal floating dock offering access to the river for kayaks and small boats. Located in the picturesque Lower Connecticut River Valley, Chester is known for its charming village, galleries, shops, dining, and brewery. Nearby you'll find the historic Haddam-Chester Ferry, Goodspeed Opera House, and Gillette Castle State Park. Cockaponset State Forest nearby offers miles of trails for hiking, biking, and riding.
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 cheerful & sunny dining room opens to a huge back deck overlooking a private yard that backs up to North Quarter Park-perfect for entertaining, walking trails or relaxing outdoors. Two first floor bedrooms and a full bath offer easy one-floor living. The light & bright upper-level multipurpose room is perfect for a home office, hobby room, studio or den. The updated electrical service is equipped with a generator transfer switch & the generator conveys. Plenty of storage in the full basement. Enjoy peaceful surroundings with mature trees and a park-like backyard, yet just a short stroll to restaurants, galleries, coffee shops, and the Sunday Farmers' Market in the heart of Chester. Convenient to Route 9, the Connecticut River, the Chester Ferry and the scenic shoreline. A truly special property offering charm, flexibility, and the lifestyle of one of Connecticut's most beloved villages-welcome home to 79 Middlesex Avenue, Chester CT.
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. Inside, the home is a masterpiece of artisan post and beam craftsmanship, with a spacious great room featuring soaring ceilings, skylights that bathe the space in natural light, and exquisite woodwork that brings warmth and character to every corner. The thoughtful layout includes a generous primary suite with its own bath, two additional bedrooms, a full bath, and a convenient powder room for guests. Outside, the property is equally enchanting. The oversized detached garage and expansive workshop, both with the artisan craftsmanship of the main house, provide plenty of room for your hobbies and projects, while the barn and stables are ready for your animals. Whether you dream of an equestrian escape or simply crave a peaceful haven to enjoy nature, this home offers it all. From the captivating craftsmanship to the stunning natural surroundings, this is more than just a home, it's a retreat, a sanctuary, and a lifestyle.

Chester is located in Connecticut. Chester, Connecticut has a population of 3,787. Chester is less family-centric than the surrounding county with 25.99% of the households containing married families with children. The county average for households married with children is 27.85%.
The median household income in Chester, Connecticut is $93,333. The median household income for the surrounding county is $90,833 compared to the national median of $69,021. The median age of people living in Chester is 49.5 years.
The average high temperature in July is 84.4 degrees, with an average low temperature in January of 19.1 degrees. The average rainfall is approximately 50.4 inches per year, with 30.3 inches of snow per year.