The median home value in Chester, CT is $607,500.
This is
higher than
the county median home value of $299,950.
The national median home value is $308,980.
The average price of homes sold in Chester, CT is $607,500.
Approximately 64% of Chester homes are owned,
compared to 26% rented, while
10% are vacant.
Chester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you like to see a property, contact Chester real estate agent to arrange a tour today!
Learn more about Chester.
Open House:
Sunday, 5/18 11:00-2:00PM
Calling all artists, authors, creatives. This is the perfect space to create, dream, let your imagination bloom. Surrounded by Chester Creek and across the street from a beautiful waterfall sits 43 North Main Street Chester. Beautiful farm porch, detached two car garage, the "glass house" at the edge of Chester Creek to relax and watch nature. 3 bedrooms, 1 1/2 baths, beautiful propane fireplace, updated yet all the original charm and character remain. Sidewalk to Chester Village with restaurants, shops, art galleries, and the incredible (in season) farmers market.
A perfect opportunity for a 'Gentleman's Farm' in this wonderful 3200 Sq/Ft Farmhouse Colonial on 11.8 Acres of Great Equestrian Lands w/ Beautiful Plantings, Custom Gardens & Direct Access to the Riding Trails of the Cockaponset State Forest & a short walk to Cedar Lake. You cannot beat this location! Check out our Virtual Reality Tour & those Pics! The Open & Contemporary Floor Plan has 'Nothing but Glass & Sunlight throughout it! Gleaming Hardwoods, Spectacular Fieldstone Fireplace w/ Insert, Large Eat-In Kitchen w/ Breakfast Island, Corian Counters & Built In Ovens. Oil Hot Water Heat, Central AC, Mini Split Hyper Heat & AC, Oversized 2 Car Garage w/ terrific private access to finished space above for those 'Work from Home' Buyers. Four Bedrooms w/ 3 Full Bathrooms and additional living space in the full walk up attic w/ plenty of space for those aging teenagers! It is a great time to buy your dream home! We are always here to help!
Open House:
Sunday, 5/18 12:00-2:00PM
Welcome to a one-of-a-kind estate where history meets modern comfort - located within walking distance to Chester's charming downtown. This home was a barn that stood on farmland since 1740, thoughtfully relocated to the stunning 5.31-acre rocky hillside it occupies today. The barn was transformed into a breathtaking residence, preserving its rustic character while infusing modern functionality and elegant design. Step inside to the open-concept kitchen and living area, where 12-ft glass French Doors fill every corner with natural light. The loft above, nestled within exposed beams, offers a bedroom and versatile space. The main floor features a spacious walk-in pantry, a study/sitting room with floor-to-ceiling shelves, and a primary bedroom retreat with cashmere-lined walls and 40-ft ensuite bathroom and laundry room. The lower level includes a bedroom and large area ready to be finished into extra living space if desired. Venture further down to discover the wine cellar and the unique 'Rock Room' showcasing the natural quarry beneath. Outside, the large deck and patio provides sweeping views of the park like setting - framed by stone walls, lush gardens, and fruit trees. More highlights include a 2 car garage, shed, whole house generator, and foundation with utilities ready for a greenhouse, workshop, or other use. A valuable land strip offers potential for a 2nd driveway or subdivision. Don't miss this remarkable home with a story to tell - your next chapter starts here!
The charming 3 bedroom colonial with a large attached garage and 2 outbuildings overlooks a lovely 5 acre pond. The home features a large kitchen and 2 1/2 baths with laundry on the second floor. Highlighting the living room is a 30 ft. Cathedral ceiling. Master bedroom includes an interior balcony, overlooking the living area. Generous windows and sliders afford beautiful open views of the property. Additionally, there is classic pine paneling throughout the home.
Bella Vista: A Timeless Italianate Treasure on 6 Acres. Step into a piece of history, a magnificent Italianate farmhouse 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 gem inspired by the quintessential farmhouses of northern Italy. Its grandeur is immediately apparent upon arrival, with six sprawling acres that offer a private and serene retreat. The European-style open terrace is a highlight, adorned with elegant pergolas that invite leisurely afternoons soaking in the panoramic views. It's the perfect setting for hosting gatherings or simply enjoying the tranquility of your surroundings. Inside, the residence boasts four well-appointed bedrooms, two and a half baths, and an impressive five fireplaces, ensuring a warm and inviting atmosphere throughout the home. Each room is a celebration of the past, with meticulous attention to detail that honors the original design while offering modern comforts. Bella Vista is not just a home; it's a legacy waiting to be continued by those who appreciate the romance and craftsmanship of a bygone era. Embrace the chance to make Bella Vista your own and carry on the tradition of elegance and sophistication that only a home of this caliber can provide
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 hot water heater, oil tank (2022), and a whole-house generator, ensuring modern comfort while maintaining historic charm. A delightful patio with a gazebo, adorned with wine grapes, provides a perfect spot to relax and enjoy the picturesque surroundings. Additionally, the property features a 1020 square foot heated "artist studio" complete with a kitchen, full bath, and loft. This versatile space is ideal for an in-law suite, office, workshop, art studio, or potential rental. The property also includes a detached garage with its own driveway and a storage shed, enhancing its functionality. Located close to Chester's fine dining, boutique shopping, and the recreational offerings of Cedar Lake with its two public beaches, this home offers a blend of historic elegance and modern convenience. Perfect for those seeking a serene, yet accessible retreat, 28 S Wig Hill Road is a unique opportunity to own a piece of Chester's rich history, set amidst a stunning natural landscape.
