Chester Real Estate

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

$495,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
$799,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
$499,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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
ACTIVE Status ⋅ 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
$299,900
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
$900,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
$2,100,000
11 Beds ⋅ 12 Baths ⋅ ACTIVE Status ⋅ 24170551 MLS
A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor. The portfolio is fully occupied and generates approximately $210,000+ in current gross income, with upside to over $280,000 stabilized, driven by residential and commercial rent growth. At stabilization, the portfolio delivers approximately $175,748 NOI and a 8.37% cap rate, supported by a strong 1.58x DSCR. The possibility to develop the 3rd floor of 163 Main Street into additional units can drive returns even higher! This is a rare opportunity to acquire scale across two supply-constrained markets, combining in-place cash flow with clear mark-to-market upside across both residential and commercial components.

59-65 Maple St, Chester
$3,150,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24166793 MLS
Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.

288 Middlesex Ave, Chester
$75,000
ACTIVE Status ⋅ 24164488 MLS
Discover the perfect setting to build your dream home in the desirable Wig Hill area of Chester, Connecticut. Located near Cockaponset Sate Forest and the scenic Connecticut River valley. This beautiful one-acre level building lot features approximately 211 feet of road frontage and dimensions of roughly 200 x 200 feet, offering ample space and flexibility to bring your custom plans and ideas to life. Set in a scenic location and not located in a flood zone per MLS property flood zone map, the lot provides both privacy and room to grow. Enjoy Chester's exceptional quality of life with its charming village center, vibrant arts scene, unique shops, acclaimed dining, and year-round community events, plus easy access to hiking trails and the Connecticut River. Bring your vision and make your dream home a reality in this inviting and picturesque setting.

Turkey Hill Rd, Chester
$1,450,000
ACTIVE Status ⋅ 24149430 MLS
Two industrial buildings. 1961 building is 9,875 sf; 1987 building 18,650. Loading docks, overhead doors, several offices, break room, security system, ample parking, located off Rte 154 with proximity to Route 9 and I-95. Owner/user occupied for decades and have outgrown the space. Available immediately.

10 Denlar Dr, Chester
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