Chester Real Estate

Welcome to Chester, Connecticut – a charming New England town nestled in the heart of Middlesex County. With its picturesque landscapes and vibrant community spirit, Chester offers a unique blend of historical charm and modern convenience that makes it an ideal place to call home.

Steeped in rich history, Chester was established in 1836 and boasts a beautifully preserved downtown area that features a variety of quaint shops, art galleries, and delightful eateries. Stroll along the scenic streets lined with colonial-era buildings, and you’ll discover the town’s artistic flair, showcased through numerous local events and festivals throughout the year. One highlight is the annual Chester Fair, where residents gather to celebrate the town's agricultural roots with rides, games, and delicious local food.

Nature lovers will appreciate Chester’s stunning surroundings, with access to the Connecticut River and nearby state parks offering ample opportunities for hiking, fishing, and outdoor recreation. The Chester-Hadlyme Ferry, one of the oldest continuously operating ferries in the country, adds a touch of adventure, providing a scenic route across the river.

Education is a cornerstone of the Chester community, with highly-rated schools and a commitment to fostering a nurturing environment for students. Families will find a welcoming atmosphere, with a strong sense of community and numerous activities for children and adults alike.

Whether you’re drawn to Chester for its rich history, vibrant arts scene, or serene natural beauty, this delightful town is ready to welcome you home. Discover the charm of Chester, where every corner tells a story, and community spirit thrives.

Newest Listings in Chester

$385,000

2 Beds ⋅ 2 Baths ⋅ 24185639 MLS

Multiple offers - Seller requests highest and best, Monday, 7/27 by 5PM. No escalation clauses. Fantastic Opportunity in the Heart of Chester! Discover the potential of this charming 2 Bedroom, 1.5 bath ranch, perfectly situated within walking distance to downtown Chester. The highlight of this home is a newer, heated sunroom boasting wood floors, cathedral ceilings and an abundance of natural light overlooking a private 2.39 acre lot. The partially finished, walk-out lower level offers excellent flexible living space, complete with a half bath (with room to expand to a full shower) and a small kitchenette - ideal for an in-law or guest suite. Key features include: New oil-fired furnace; public water; central air; whole house generator; 200 amp electrical service; freshly painted interior, one car garage and storage shed. Bring your updates and vision to life! With fabulous expansion possibilities, this property is ready for its next chapter. Enjoy being just steps away from Chester's vibrant village center, known for its boutiques, acclaimed restaurants, art galleries, theater and the historic Chester Ferry crossing the Connecticut River.

25 Goose Hill Rd, Chester

$495,000

3 Beds ⋅ 3 Baths ⋅ 24192544 MLS

Discover the incredible potential of this custom-built Colonial, ready for your personal style and finishing touches. Designed with comfort and functionality in mind, the main level features a dedicated home office complete with extensive shelving and abundant storage, perfect for staying organized while working from home. Upstairs, you'll find three generously sized bedrooms and two full baths, including a beautifully glass tiled hall bath that adds beachy vibes. The spacious primary suite offers both a walk-in closet and an additional traditional closet, with ample room for a king-sized bed and your favorite furnishings. The bright, functional kitchen boasts an abundance of cabinetry, stainless steel appliances, and the convenience of a first-floor laundry room just steps away, between the kitchen and the powder room. The finished lower level provides valuable additional living space, ideal for a family room, recreation area, home gym, or hobby room, with direct access to the oversized two-car garage. With fresh paint and your personal decorating touches, this home can truly shine. Best of all, you're just a short walk from Chester's picturesque town center, where you'll enjoy charming shops, restaurants, galleries, and community events. Experience firsthand why Chester is consistently celebrated as one of Connecticut's most beloved small towns.

42 Straits Rd, Chester

$450,000

3 Beds ⋅ 3 Baths ⋅ 24192206 MLS

Welcome to this inviting 3-bedroom split-level ranch, ideally situated within walking distance to the heart of Chester Village. Designed for comfortable living and entertaining, the home features a spacious family room with sliders leading to a large deck overlooking the inground pool. The backyard is an outdoor retreat complete with a pool house, gazebo with electricity, mature fruit trees, and a large open yard offering endless possibilities. Inside, you'll find two fireplaces-one in the living room and another in the lower-level recreation room-creating warm and welcoming spaces throughout the seasons. The remodeled kitchen features granite countertops, ample cabinetry, and a functional layout for everyday living. The primary bedroom includes a private half bath, and the two-car attached garage provides plenty of storage and convenience. Recent upgrades include a newer boiler, central air condenser, and garage doors, providing added value and peace of mind. Just a short walk from Chester Village, you'll enjoy convenient access to art galleries, locally owned restaurants, unique boutiques, and seasonal community events. This home offers a wonderful opportunity to add your personal touches while enjoying a spacious property, exceptional outdoor amenities, and all that Chester has to offer.

22 Goose Hill Rd, Chester

$799,900

3 Beds ⋅ 3 Baths ⋅ 24179377 MLS

Set on 33.97 private acres in beautiful Chester, CT, this inviting home offers space, privacy, and scenic views. The main level features a primary bedroom with a full bath, while upstairs you'll find 3 additional bedrooms with 2 full baths. The bright, open living room features soaring ceiling and a second floor balcony overlooking the main living space, creating an airy feel. Large south facing windows bring in abundant natural light and capture lovely views of the lightly wooded landscape. The home's attractive vertical wood siding adds character, while the expansive acreage provides a peaceful setting just minutes from the charm, shops and restaurants of Chester village.

88 Winthrop Rd, Chester

$439,900

3 Beds ⋅ 2 Baths ⋅ 24190609 MLS

One floor living in this well maintained Ranch. 1 Full Bath & One 1/2 Bathroom. Hardwood floors. Fireplace in Living Room. Large Eat-in kitchen with Stainless Steel appliances. Recent upgrades include: New HVAC, New 200 AMP electric panel, new roof, new pellet stove, and remodeled bathroom. Open and level yard with nice plantings. Solar system recently installed to assure reasonable utility costs. All in a quiet neighborhood not far from Chester Village or CT River!

1 Kirtland Ave, 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

$3,675,000

24188369 MLS

Prime Investment Opportunity in Chester, CT Presenting 189-191 Middlesex Avenue, well located, mixed-use property offering an exceptional investment opportunity in the heart of Chester, Connecticut. This 21,905 SF complex features a mix of retail, office, and residential spaces, with long-term tenants, ensuring stability and consistent revenue. Property Highlights * Fully Leased with established tenants * Strong financials 2026 * Significant annual increases and pass-through for operating expenses * Ample on-site parking for tenants and visitors * High visibility on a well-trafficked state road * Well-maintained by current ownership for 19 years Location Benefits * 3.02-acre lot in a desirable commercial zone (C) * Built in 1986, offering modern infrastructure * Convenient access to Route 9 and Exit 3 on Route 154 * Proximity to Chester Village-a vibrant hub of dining, shopping, and scenic attractions About Chester, CT Nestled along the Connecticut River, Chester boasts a unique blend of New England charm and commercial opportunity. Its historic appeal, picturesque views, and strong community make it an attractive destination for businesses and residents alike. This turnkey investment offers immediate and long-term financial rewards in a thriving market. Don't miss out on securing a property with both stability and future growth potential.

189 Middlesex Ave, Chester

$525,000

3 Beds ⋅ 3 Baths ⋅ 24186457 MLS

Set at the end of a quiet dead-end road, this three-bedroom ranch offers the ease of one-floor living, exceptional privacy, and over four acres of peaceful surroundings in Chester. Inside, two inviting wood stoves create warm, comfortable gathering spaces, while a newer roof adds peace of mind. Step outside to a covered deck that flows seamlessly to an open deck overlooking the private backyard with seasonal views of the Connecticut River-an ideal setting for relaxing, entertaining, or enjoying the changing seasons. The home also features a spacious two-car attached garage and a large accessory dwelling unit (ADU) with a full walkout to the backyard, offering flexible space for extended living arrangements, guests, a home office, recreation, or other permitted uses. Combining acreage, privacy, versatile living space, and a tranquil setting, this property is ideally located just minutes from Chester Village, offering easy access to local shops, restaurants, art galleries, breweries, nearby marinas, and the scenic Connecticut River.

12 Meadow Ln, Chester

$299,900

3 Beds ⋅ 1 Baths ⋅ 24186867 MLS

Welcome to 92 Water St, a charming 1927 two-story Colonial offering a rare opportunity to own waterfront property in picturesque Chester, CT! This 3-bedroom, 1-bathroom home is perfectly situated right on the water, offering tranquil riverfront views and an unbeatable location just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining. Sitting on an 11,761 sq. ft. (0.27-acre) lot bounded directly by the water, this home features classic vinyl siding, a paved driveway, and a comfortable layout, making it a fantastic canvas for your dream riverfront retreat. Whether you are an investor seeking a value-add property or a homeowner looking for direct water access, the potential here is outstanding. Looking to expand your portfolio or create a larger waterfront compound? This property presents a unique dual-purchase opportunity: 92 Water St can be sold as a package with the neighboring property at 90 Water St. Buyers should note that the two properties conveniently share an existing septic system. This rare Chester waterfront offering is packed with potential and won't last long. Bring your vision and schedule your showing today!

92 Water St, Chester

$274,900

1 Beds ⋅ 1 Baths ⋅ 24186861 MLS

Rare waterfront opportunity! Nestled directly on the water, 90 Water St is a 1-bathroom Ranch currently configured as a 1-bedroom, but offering a spacious layout that easily converts to a 2-bedroom home. Built in 1950, the property provides a fantastic foundational footprint. It features a large 13'6" x 20'10" living room and a versatile 10'3" x 20'10" family room-the ideal space to partition into a second bedroom or home office. A combined 10'5" x 16'2" kitchen/dining area and a comfortable 12'5" x 10'3" primary bedroom complete the interior. Location is everything, and this property delivers. Situated right on the water, it offers tranquil views and the canvas for an incredible outdoor living space on the riverbank. Beyond the backyard, you are just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining. Looking to expand your portfolio or create a larger waterfront compound? This presents a unique dual-purchase opportunity: 90 Water St can be sold as a package with the neighboring property at 92 Water St (note: the two properties conveniently share an existing septic system). Whether you are an investor looking for a value-add rehab project or a buyer seeking a waterfront getaway with a vision to maximize this footprint, the possibilities are endless. Bring your contractor and imagination-schedule a showing today!

90 Water St, Chester

$2,200,000

4 Beds ⋅ 4 Baths ⋅ 24180698 MLS

A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Registery of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity with six fireplaces, original hardware, twelve-over-twelve windows, elegant period moldings, richly detailed mantels, and a commanding facade highlighted by Ionic columns, a Palladian window, fanlight entry, and granite foundation. A 19th-century carriage house on the property evokes the atmosphere of Warner's original gentleman-farmer estate. This historic landmark property sets the stage for unforgettable event possibilities on picturesque pastoral grounds. 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. Extensive original letters, bills, receipts, and construction records survived, documenting the artisans, materials, suppliers, and methods used to create this architectural masterpiece. Chester offer an abundance of amenities / local events, and borders the CT River.

47 E Kings Hwy, Chester

$805,000

2 Beds ⋅ 3 Baths ⋅ 24164157 MLS

Step into timeless New England charm with this beautifully updated 1901 Colonial, where classic character meets modern comfort just moments from the heart of Chester. Thoughtfully renovated between 2008 and 2023, this inviting home offers warm, sun-filled spaces designed for both everyday living and and entertaining. Gather in the formal living and dining rooms, enjoy casual meals in the updated kitchen with granite countertops and stainless steel appliances, or relax in the open family room that flows seamlessly to the deck-complete with an outdoor shower for summer living. A first floor office or den with built-ins and it's own private entrance provides the perfect space for working from home or welcoming clients. Upstairs, two comfortable bedrooms and a full bath surround a charming landing, while the third floor offers a cozy retreat with bedroom area and sitting room-ideal for guest or a peaceful hideaway. Set on a level usable property with mature landscaping, the grounds feature a rustic cabin currently used as an art studio, adding creative flexibility and a touch of whimsy. All this, just around the corner from Chester's vibrant town center with it's shops, restaurants and community events, makes this home a rare blend of historic charm, modern updates and walkable small-town living. This property is subject to probate approval.

6 Jagger Ln, Chester

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.