Chester CT Real Estate & Homes for Sale

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 woodstove, is perfect for relaxing, while the formal dining room flows seamlessly into the kitchen, ideal for entertaining. A versatile additional living area, converted from the original two-car garage, adds even more space to enjoy. Upstairs, the primary bedroom features an en-suite bath, with three additional bedrooms and a second full bath on this level. The lower level offers ample storage and the potential for additional living space. Outside, a private backyard with mature fruit trees creates a peaceful retreat. With a durable 50-year roof installed in 2018 and energy-efficient solar panels, this property combines charm with modern updates. Enjoy a tranquil lifestyle with easy access to all that Chester has to offer!

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.

Lovely Colonial Home with Fabulous 2 Story In-law suite with private entrance. The main part of the home is highlighted with gleaming hardwood floors and both a finished great room in the attic and a spacious family room in the lower level. The kitchen features granite countertops and cherry cabinets while the front to back living room as a pretty fireplace and opens to a private deck overlooking the backyard. 3 generous size bedrooms are on the second floor with the potential for more bedrooms in the finished attic or the in-law side of the home. Extra amenities in this home are: irrigation system, solar panels, leased generator, storage shed, roomy paved driveway, front stone paver walkway, oversized garage with EV charging station, security cameras, built in safe and so much more.

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. The transformation included removal of randomly erected partition walls throughout, and reworking the floor plan. Original wall planks were unearthed, hand sawn chestnut flooring was restored, and extra planks were used to create mantles for the 2 fireplaces. The live-edge sheathing in the ceiling was preserved giving the space simultaneously a sense of grandiosity and warmth. The resulting home is an inviting and comfortable retreat for a few or a fabulous entertaining space for many. From the oversized deck complete with outdoor kitchen, look out over the vast field and watch the wildlife including foxes, deer, bobcats, coyotes, American Kestrels, goldfinch and eastern bluebirds, possums, raccoons and more. A few apple trees remain, the fields slope and undulate untouched by time. Enjoy a cup of coffee or a glass of wine in the gazebo or al fresco next to 'frog pond' or as you meander along the path around the pasture. The fully updated estate with new HVAC, roof, solar, kitchen, bathrooms, outdoor shower, electrical, plumbing and septic system is ready for your vision;

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 board wood floors throughout. Sold as-is awaiting your paint palette.

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.