Chester CT Real Estate & Homes for Sale

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.

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 area leads to the wraparound deck, featuring mahogany handrails and stainless steel cables. The first-floor primary suite features a full bathroom with slate flooring, while the remainder of the main level is adorned with beautiful white oak hardwood floors throughout. Upstairs, two generously proportioned bedrooms await, one with a full en-suite bathroom also featuring slate floors. The second-floor layout offers the flexibility to easily convert one of the bedrooms into two, accommodating a four-bedroom home if desired. A convenient laundry room and white oak hardwood floors. Heated floors throughout, including the walkout basement, and a five-zone heating system. Ample closet space, while the private, tucked-away location provides a serene and quiet neighborhood setting. Conveniently situated, this property offers unparalleled access to the Chester ferry and the renowned Gillette Castle, as well as proximity to the village, restaurants, and a wealth of local attractions. All offers are subject to the seller's attorney review and approval.

Welcome to the WATERFALL HOUSE an iconic 4-bedroom, 3-bathroom treasure, perched above the scenic Pattaconk River in the heart of historic Chester Village, overlooking a 15-foot waterfall and offering pastoral views over the fabled Jennings Pond from every room. This property was gutted and tastefully renovated in 2022, blending modern luxury with historic charm. Just a 5-minute walk to the Village's restaurants, shops, and art galleries, the home offers unparalleled convenience. Inside, you'll find new wide board floors, a new chef's kitchen, mahogany posts/beams, and high ceilings. The master bedroom suite is truly one of a kind, with a fireplace, dressing room, and a library/sitting room in a separate tower. The lower level boasts a private bedroom suite with a separate entrance and deck, a fireplace, bamboo flooring, and a large cedar closet. Outdoor spaces include new bronze fencing around multi-level decks and terraces, and a large riverside meadow perfect for gatherings. Mature landscaping with ornamental trees, bushes, and perennials. Additional features include a separate carriage house with guest suite, new state-of-the-art mechanicals, a new whole-house generator, and proximity to major commuting lines and Amtrak stops. This piece of heaven in Chester Village offers the discerning buyer a perfect blend of history, luxury, and convenience. Don't miss this opportunity to see this truly unique property home. Schedule your private tour today!

This Bright and Comfortable Home features a lovely main living area, highlighted with a great finished lower level and a quiet finished 3rd floor. In addition, there is a spacious In-law suite with living room, kitchen area, main floor bedroom, laundry and a 2nd floor living space, with 2 private / separate entrance. Ample paved parking is available for all. The main space includes a lovely kitchen accented with granite counters, cherry cabinets and pantry. A formal dining room, a front to back living room opening to a large deck overlooking the private back yard, storage shed, above ground pool, and fire-pit area. Upstairs are the Primary Bedroom, 2 spacious bedrooms and access to the 3rd floor. The oversized garage has extra space for a workbench, storage and many extras; including an EV charging station. There are so many extra features: Solar panels, whole house generator (leased), sprinkler system for the yard, automatic exterior lighting, decorative stone and paver walls and walkway, security system, built-in safe and so much more. This home has so much potential for all your needs.

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.