Chester Real Estate

Welcome to Chester, Connecticut – a charming town nestled in the heart of Middlesex County. Known for its picturesque landscapes and vibrant community, Chester is the perfect blend of small-town charm and modern convenience. With its rich history dating back to the 17th century, the town boasts a delightful mix of historic architecture and contemporary amenities that make it a truly unique place to call home.

One of Chester's standout features is its stunning natural beauty. Surrounded by lush forests and rolling hills, outdoor enthusiasts will find plenty of opportunities for hiking, biking, and exploring the great outdoors. The nearby Connecticut River offers idyllic spots for kayaking and fishing, while the town’s parks provide serene spaces for picnics and leisurely strolls.

Chester is also known for its thriving arts scene. The town hosts various cultural events throughout the year, including art shows, music festivals, and farmers' markets that showcase local artisans and fresh produce. The historic downtown area is lined with charming boutiques, cafes, and restaurants, making it a delightful place to spend an afternoon.

Families will appreciate Chester’s strong sense of community and excellent school system, which emphasizes both academic achievement and character development. With a welcoming atmosphere and a range of recreational activities, Chester is an ideal place for families, retirees, and anyone looking to enjoy a peaceful lifestyle.

Whether you’re drawn to its rich history, vibrant culture, or beautiful surroundings, Chester, CT, is a hidden gem that promises a fulfilling and enriching living experience. Discover the charm of Chester and find your perfect home in this enchanting town!

Newest Listings in Chester

$749,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217528 MLS

Privacy, space, and location combine with this custom colonial on over two private acres at the end of a quiet cul-de-sac. This 2,662-square-foot home offers a rare opportunity to enjoy the tranquility of a tucked-away setting without sacrificing proximity to downtown Chester. An inviting covered front porch welcomes you to sit and enjoy the peace of this quiet neighborhood. Once inside, the entryway is bordered by 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, an eat-in kitchen, and pantry. The kitchen leads to a large deck overlooking the backyard, perfect for dining, entertaining, or simply enjoying the natural beauty of the property. 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. Two sizable bedrooms and a guest bedroom share a full bath. There is a bonus room over the two-car garage that could serve as a den, office, or playroom 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 convenience of downtown Chester just moments away. A special opportunity to make this well-established property your own.

13 High Field Ln, Chester

$450,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24216914 MLS

Just a quick stroll from the heart of Chester Village, this absolutely charming three-bedroom, one-bath home offers a wonderful combination of classic character, recent improvements, and an exceptional location. From the moment you arrive, the inviting enclosed front porch welcomes you, providing additional living space and a wonderful spot to relax. Inside, the home retains much of its original charm, with beautiful hardwood floors, rich wood moldings throughout, and a lovely built-in corner hutch in the dining room. The kitchen has been updated from its original design, offering modern convenience while complementing the home's character. Recent improvements in 2026 include a freshly painted interior, refinished hardwood floors, and a professionally waterproofed basement. A walk-up attic offers potential for future expansion or additional storage. Situated on just under half an acre and only 0.2 miles from downtown, you'll enjoy easy access to Chester's wonderful restaurants, art galleries, boutiques, theater, and summer farmers market. With its timeless architectural details, thoughtful updates, and proximity to one of Connecticut's most vibrant villages, this home presents a wonderful opportunity to enjoy all that Chester has to offer. A must-see!

6 School Ln, Chester

$525,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24215476 MLS

Welcome home to this meticulously maintained Cape Cod-style residence, nestled on a tranquil cul-de-sac just steps from vibrant Chester Village. Cherished by the same owner for over 34 years, this home radiates pride of ownership, classic charm and everyday functionality. The main level features gleaming hardwood floors and a beautifully updated kitchen; complete with granite countertops, newer stainless steel appliances, a breakfast bar, and French doors providing access to the deck and private backyard. The seamless flow leads into a light-filled living room anchored by a cozy pellet stove, a formal dining room, and a generous laundry/pantry room with custom built-ins. A main-floor bedroom and full bath offer flexible options for guests, main-level living, or a dedicated home office. Upstairs, find two spacious bedrooms, including a primary suite with its own private bath. The second bedroom boasts a walk-in closet plus a separate oversized dressing/flex room. The lower level features a second pellet stove, offering endless potential for additional living space. Step outside to enjoy your backyard oasis featuring a custom-built, oversized fireplace ~ the ideal setting to unwind and entertain. Schedule your private showing today to experience the perfect blend of comfort, character; and village convenience! Please note: Professional Photos to follow.

6 Gilbert Hill Rd, Chester

$775,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24213471 MLS

Village Charm, Private Setting, Modern Comfort. Discover the best of Chester living in this recently updated Colonial, ideally situated in the heart of downtown. Blending New England character with fresh, refined updates, this inviting home offers a wonderful balance of classic charm, modern comfort, and everyday convenience. Privately nestled...while just steps from the shops, restaurants, galleries, and local favorites that make downtown Chester so special, the property offers a sense of retreat without sacrificing walkability or connection to the community. Thoughtfully refreshed and beautifully presented, the home feels welcoming, with the enduring appeal of traditional Colonial architecture and the ease of modern living. Whether enjoying a quiet morning at home, strolling into the village for dinner, or taking in the charm of one of Connecticut's most beloved small towns, this is a home that makes the most of its exceptional setting. A rare opportunity to enjoy the character of a classic Colonial, the privacy of a tucked-away setting, and the convenience of being right where you want to be. **Charming, polished, and unmistakably Chester.**

7 Hickory Hill Dr, Chester

$289,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24214929 MLS

Recently remodeled retreat nestled along the Pattaconck Brook, just seconds from the heart of Chester and conveniently located near Route 9. This 2 bedroom 1 bathroom home set on 2 acres offers a peaceful setting with the charm of nature. Extensive updates completed, including new siding, roofing, electrical, sheetrock, flooring, and a fully remodeled kitchen in 2021. A spacious living room and dining area with a wood stove for an alternative heat source. Additional improvements include a well pump, on-demand hot water and furnace heat exchanger. An impressive 45' x 28' garage with a walk-up loft offering another place to escape and unwind. Take advantage of this one of a kind opportunity! This is a manufactured home with additions and will not qualify for financing. CASH ONLY. Book your showing today!

173 W Main St, Chester

$715,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24213774 MLS

Discover move-in-ready living in desirable Chester, one of the Connecticut River Valley's most charming towns! Set on two picturesque acres across from Cockaponset State Forest, this beautifully renovated 4-bedroom, 3.5-bath home blends classic New England character with modern comfort, approximately three miles from Chester Village and Cedar Lake. Inside, refinished hardwood floors, multiple fireplaces, and inviting living spaces create a warm welcome, all updated & freshly painted. The stunning new kitchen features, beautiful cabinets, quartz countertops and premium THOR Gordon Ramsay Collection appliances. A first-floor bedroom & full bath offer flexibility for guests or main-level living. Upstairs, the primary suite boasts a fireplace, 6-foot walk-in closet, a spa-inspired bath with a rain shower and soaking tub! Two more bedrooms & yet another newly remodeled full bathroom complete this level. Approximately 800 square feet of permitted finished lower-level space, complete with a fireplace and bathroom adds room to relax, work, or entertain. Major improvements include a NEW SEPTIC SYSTEM, new plumbing, updated electrical with 200-amp service, new windows, siding, and gutters, plus three-zone central heating and air conditioning. Outside, enjoy a new 12' x 12' wood deck, landscaped grounds, and a private pond along the scenic rear approach. Two access points add convenience to this peaceful setting. Beautifully updated & ready to enjoy at an amazing price. Welcome home!

275 W Main St, Chester

$379,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210808 MLS

One floor living in a quiet neighborhood just outside Chester Village. The main floor has a large Living Room, Kitchen and Dining Room, 3 bedrooms, 1 bathroom. The partially finished basement has 2 addional rooms, and storage. Some unfinished projects! Ready for your updating!

40 Castle View Dr, Chester

$699,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24212291 MLS

Welcome home this beautifully redesigned house set on over 2.5 acres in picturesque Chester, a quintessential New England town celebrated for its art, history, music, theater and exceptional dining. Completely renovated for today's lifestyle while retaining its warmth and character, this three-bedroom, 2.5-bath home offers beautifully refinished hardwood floors, 9-foot ceilings and thoughtfully designed living spaces throughout. The main level is ideal for entertaining, featuring an inviting living room with fireplace and sliders opening to a balcony/deck overlooking the property. The stunning new kitchen features quartz countertops, new cabinetry, a center island, new appliances, wine cooler and a charming dining nook. A spacious 17' x 13 room provides wonderful flexibility as a home office, or guest room. An updated half bath completes the main level. Upstairs, the primary suite offers a beautifully remodeled luxury bath and walk-in closet. Two additional bedrooms and a remodeled full bath complete the second floor. The finished lower level adds even more living space with an 11' x 21' family room, interior and direct garage access. The auxiliary generator has you covered for New England winters. Move-in ready and beautifully updated inside and out, this special property combines privacy, space and modern comfort with the charm of one of Connecticut's most desirable small towns. The home you've been waiting for-just in time for the holidays!

42 Straits Rd, Chester

$579,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24207359 MLS

Rare opportunity to own a hard to find multifamily in the beautiful town of Chester! This unique 2 unit property offers space, character and flexibility in a wonderful location, just a short drive to Cedar Lake and approximately a 15 minute walk to charming downtown Chester with its shops, restaurants and small town New England appeal. Unit 1 spans 3 levels and features 3 bedrooms, with 2 upstairs and 1 on the main level, 1.5 baths, hardwood floors, exposed beams in the living room and mini splits for heat and A/C. The half bath is ready to be completed, with the seller leaving the toilet, vanity and lighting for the next owner. Some windows have been replaced and the porch features new decking. Unit 2 offers 1 bedroom, 1 full bath, propane heat and a spacious living room with high ceilings. The bathroom features a new vanity and walk in shower. Each unit enjoys its own separate yard space. Major improvements include a new roof, new septic system and new insulation. The property also has a tankless hot water heater and separate electrical meters. Generator stays! A very large basement provides excellent storage and includes an area a previous owner began framing, along with multiple additional storage spaces. A rare opportunity for an investor or owner occupant looking to enjoy all that Chester has to offer!

84-86 Spring St, Chester

$1,900,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24206419 MLS

The Johnathan Warner house, and later known as the Warner-Brooks House was built by Johnathan Warner in 1798 and is a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Register of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity. Heavily documented during construction are original bills, receipts, and construction records documenting the artisans materials, suppliers, and methods used to create this architectural masterpiece. Revered by historians and preserved with exceptional care, this irreplaceable legacy property offers a rare opportunity to own one of Connecticut's most significant surviving Federal residences. A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Jonathan Warner was the founder of the Chester-Hadlyme Ferry which is right down the road and is still in operation today. Johnathan was a Civic Leader, director of the Middlesex Turnpike, Merchant, Ship Owner, Farmer, Constable, and a justice of the peace with his courtroom right at the house. This is all documented in a book called Johnathan Warner 1728-1810 " A Man of Parts" telling all about the home building and Johnathan's life. Copies can be found at the Chester Historical Society. Buyer must due diligence regarding subdivision possibilities. 3.2 acres of which most is a huge level cleared open field.

47 E Kings Hwy, Chester

$2,995,000

4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 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

$252,500

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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! One of the parties to the LLC has an active real estate license

92 Water St, Chester

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Chester Real Estate

Newest Listings in Chester

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