Chester Homes for Sale

Welcome to Chester, Connecticut – a hidden gem nestled in the heart of Middlesex County. This charming town, known for its picturesque landscapes and vibrant community, offers a unique blend of history, culture, and natural beauty. With its quaint downtown area lined with boutique shops, delightful cafes, and art galleries, Chester exudes a warm, welcoming atmosphere that invites both residents and visitors to explore its rich heritage.

One of the town's standout features is the stunning Connecticut River, which provides ample opportunities for outdoor enthusiasts. Whether you enjoy kayaking, fishing, or simply taking a leisurely stroll along the riverbank, Chester’s natural surroundings are sure to inspire. The town also boasts numerous parks and hiking trails, making it an ideal location for those who appreciate an active lifestyle.

For those considering a move to this enchanting town, Chester offers a diverse array of homes for sale. From charming historic houses that reflect the town’s rich past to modern, spacious family homes that cater to today’s lifestyle, there’s something for everyone. Whether you’re a first-time buyer, looking to downsize, or searching for a vacation retreat, Chester’s real estate market is brimming with options that cater to various tastes and budgets.

As you explore the homes for sale in Chester, you’ll discover not just a place to live, but a vibrant community to be a part of. With its friendly neighbors, excellent schools, and a strong sense of community, Chester is truly a place where you can put down roots and thrive. Come experience the charm of Chester, where your dream home awaits!

Newest Chester Homes for Sale

$824,900

4 Beds ⋅ 4 Baths ⋅ 24204638 MLS

Completely Reimagined 4 Bedrooms, 3.5 Bathrooms, 2 Acres, Luxury Primary Suite, Finished Lower Level. This classic New England charm meets a stunning, comprehensive renovation. Directly across from Cockaponset State Forest, this exceptional Chester home has been thoughtfully transformed to deliver modern luxury, comfort, and effortless turnkey living. From the moment you step inside, you'll notice the attention to detail. Central air with heating and cooling. Home has audio and visual hardwired security system on property. Beautifully refinished hardwood floors flow throughout the home, complementing bright, open living spaces designed for both everyday comfort and entertaining. Multiple fireplaces preserve the warmth and character of the original home while the extensive upgrades bring it firmly into the modern era. At the heart of the home is a show-stopping new kitchen, beautifully appointed with quartz countertops and premium THOR Gordon Ramsay Collection appliances. Whether you're hosting family and friends or enjoying a quiet evening at home, this kitchen was designed to impress. Retreat upstairs to the luxurious primary suite, complete with a 6-foot walk-in closet. The spa-inspired primary bathroom creates your own private escape, featuring a custom rain shower and freestanding soaking tub-the perfect place to unwind. And the living space doesn't stop upstairs. The approximately 800-square-foot permitted finished lower level has been transformed.

275 W Main St, Chester

$465,000

3 Beds ⋅ 2 Baths ⋅ 24102694 MLS

One level living at its best! Tucked away in a peaceful neighborhood, 6 Castle View Drive offers the perfect blend of comfort, charm, and convenience. This lovingly cared for home features 3 bedrooms, 1.5 baths, and 2,031 square feet of thoughtfully designed living space all set on a beautifully level 0.43 acre lot. Step inside through the breezeway, kick off your shoes, hang your coat, and make your way into the completely renovated kitchen before settling into the sun filled living room, where a wood burning fireplace creates the perfect spot for cozy evenings. Just beyond, the bonus room offers a quiet place to read your favorite book, work from home, or simply unwind. Outside, the large fenced in backyard is ready for summer barbecues, a garden, kids at play, or four-legged friends to roam. Sit back and enjoy a quiet afternoon while listening for the nostalgic whistle of the Essex Steam Train in the distance, a small reminder of the timeless New England charm that makes this area so special. Recent upgrades include a brand new roof and siding, offering added peace of mind for years to come. When you're ready to venture out, the charm of Chester Village is just minutes away. Enjoy dinner downtown, wander through the local shops and galleries, or make an evening of it with a show at the Goodspeed. Whether you're putting down roots or looking to simplify. 6 Castle View Drive is a wonderful place to call home and ready for its next chapter

6 Castle View Dr, Chester

$499,000

3 Beds ⋅ 3 Baths ⋅ 24204497 MLS

Set on nearly 34 acres and directly abutting state forest, this unique contemporary home offers privacy, space, and endless potential. The open-concept interior features soaring cathedral ceilings and exposed beams, creating a dramatic and inviting living space. The home offers 3 bedrooms, 2.5 bathrooms, and an oversized 2-car attached garage. A separate approximately 800-square-foot barn/shop provides additional workspace, storage, or hobby potential and includes a dedicated garage bay. This home is an excellent opportunity for a buyer looking to restore and customize the property to their vision. With substantial acreage, direct access to nature, and versatile outbuildings, this property presents a rare opportunity to create a private estate, homestead, or retreat.

88 Winthrop Rd, Chester

$764,900

4 Beds ⋅ 3 Baths ⋅ 24198973 MLS

Privacy, space, and location come together in this classic custom colonial nestled on over two private acres at the end of a quiet cul-de-sac just minutes from the heart of Chester Village. Lovingly cared for by its original owners, this 2,662-square-foot home offers a rare opportunity to enjoy the tranquility of a tucked-away setting without sacrificing proximity to downtown. An inviting covered front porch welcomes you to sit down and admire the professionally landscaped front yard before entering the home. Inside, the entryway is bordered by both a living room and a formal dining room with a bay window. There is also a spacious family room with a propane fireplace, and a sunny kitchen with a center island and ample cabinet space, a breakfast nook, and pantry. The nook leads to the large back deck overlooking the backyard, perfect for al fresco dining, entertaining, or simply enjoying the natural beauty and quiet surroundings. The second story offers four bedrooms, including the primary suite with a generous walk-in closet and ensuite bathroom that features both a soaking tub and shower. Three more bedrooms share another full bath, and there is also a bonus room over the garage that could serve as a den, office, or playroom. There is a two-bay, two car garage and a full unfinished basement. Ideally situated near Chester's acclaimed restaurants, shops, galleries, and village amenities, this property offers the best of both worlds: a private retreat with the character and

13 High Field Ln, Chester

$499,900

3 Beds ⋅ 2 Baths ⋅ 24202647 MLS

Set in the charming town of Chester, this three-bedroom, two-bath home offers a versatile layout with thoughtfully updated spaces throughout. The main level features an updated kitchen, wood floors, and an inviting living room anchored by a striking raised gas fireplace that serves as a beautiful focal point. Recent improvements include a new roof and new central air conditioning condenser, adding to the home's appeal. Step outside to a multilevel deck overlooking the private backyard, creating a wonderful extension of the living space. The lower level adds exceptional flexibility with an ADU featuring its own private entrance, along with a separate laundry room and access to the two-car garage. Whether used for additional living space, guests, a home office, or other needs, the layout offers plenty of possibilities. Just a short distance from Chester Village, known for its acclaimed restaurants, independent shops, galleries, and distinctive small-town atmosphere. A unique opportunity to enjoy flexible living, outdoor space, and all that Chester has to offer.

55 Wig Hill Rd, Chester

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 24201816 MLS

Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile, deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge.

288 Middlesex Ave, Chester

$284,900

3 Beds ⋅ 1 Baths ⋅ 24198196 MLS

Charming 1927 Colonial offering a rare chance to own directly on the water in the heart of Chester. This 3-bedroom, 1-bath home spans 1,217 sq ft across two stories, with a classic layout featuring a living room and dining room on the main level and three bedrooms upstairs. Set on a 0.27-acre lot with vinyl siding and a paved driveway, the home sits right on the water with tranquil river views - a fantastic canvas for a riverfront retreat, whether you're an investor or a homeowner seeking direct water access. Just a short stroll to downtown Chester's boutiques, art galleries, and acclaimed dining. This property can also be purchased together with the adjacent 90 Water St for a larger waterfront compound (the two share an existing septic system). Bring your vision - this rare Chester waterfront offering won't last long!

92 Water St, Chester

$269,900

1 Beds ⋅ 1 Baths ⋅ 24198111 MLS

Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and comfortable primary bedroom round out the interior. Step outside to direct river frontage with sweeping water views and endless potential for outdoor living on the riverbank. All of this just a short stroll from downtown Chester's boutiques, galleries, and acclaimed restaurants. This property can also be purchased together with the adjacent 92 Water St for a larger waterfront compound (the two share an existing septic system). A fantastic value-add opportunity for an investor or a buyer with vision - bring your contractor and imagination!

90 Water St, Chester

$499,000

3 Beds ⋅ 2 Baths ⋅ 24189125 MLS

NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new electrical; the updates continued along with a new roof in 2017, and just recently new carpeting on second floor, new stove and microwave plus a new dryer. Bring your creativity to finish the lower walk-out level with its charming brick architecture along with newer radiant-heated, poured concrete floors and french doors -- this could be an amazing walkout steps to the water! This house would be a perfect vacation rental.... Rent a few weeks/Stay a few weeks!

135 Middlesex Ave, Chester

$825,000

4 Beds ⋅ 3 Baths ⋅ 24172811 MLS

Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and entertaining. At the heart of the home is a spectacular chef's kitchen featuring an oversized island, quartz counters, stainless steel appliances, custom wet bar area, formal dining space, and inviting sitting area. Just beyond the kitchen, the great room showcases vaulted ceilings, a fireplace, and an abundance of natural light. The first-floor primary suite is a true retreat with a spacious walk-in closet, and a beautifully remodeled spa inspired bathroom. Upstairs, you'll find three additional bedrooms, another full bathroom, and a dedicated laundry room for added convenience. The finished lower level offers flexible space perfect for a media room, home gym, recreation area, or playroom. Step outside onto the oversized two-tier deck overlooking the expansive backyard - an ideal setting for entertaining or relaxing in total privacy. Additional upgrades include a new roof, windows, siding, HVAC system, and brand-new 5-bedroom septic system. Complete with a 2-car garage and set in a picturesque location, this turnkey property offers the perfect blend of luxury, comfort, and functionality.

136 Goose Hill Rd, Chester

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