1,680

Chester, CT Homes

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  • 19 W Main St, Chester, CT 06412

    $1,363,500 Sold Apr 15, 2025

    • 4,205 Sq Ft
    • $324/SF
    • 136 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    19 W Main St, Chester, CT 06412

    Welcome to the Waterfall House, an iconic custom home perched above the scenic Pattaconk Brook in the heart of historic Chester Village. Overlooking a picturesque 15-foot waterfall and offering sweeping views of the serene Jennings Pond from every room, this home is a masterpiece. Meticulously renovated in 2021, it blends modern luxury with timeless historic charm. Just a 5-minute stroll from

    Michael Marsden Compass Connecticut, LLC

    19 W Main St, Chester, CT 06412
  • 14 Straits Rd, Chester, CT 06412

    $285,000 Sold Apr 09, 2025

    • 1,519 Sq Ft
    • $188/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1702

    14 Straits Rd, Chester, CT 06412

    **Incredible Opportunity Awaits!** Discover the potential of this charming three-bedroom colonial, ideally situated in the heart of Chester Village. With a new septic system, roof, and windows already installed, the groundwork is laid for your dream home. The interior is completely gutted down to the studs, offering a blank canvas for a full rehab or the perfect opportunity to build your own

    Kelly Puorro Puorro Realty Group

    14 Straits Rd, Chester, CT 06412
  • 11 Bishop Rd, Chester, CT 06412

    $350,000 Sold Apr 07, 2025

    • 1,188 Sq Ft
    • $295/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1964

    11 Bishop Rd, Chester, CT 06412

    Enjoy one-level living with protected year -round views of Cedar Lake in this 2-3 bedroom ranch. The smaller bedroom features convenient laundry access. A spacious living room with a fireplace and bay window offers a perfect spot to take in the scenic view. The home boasts hardwood floors throughout. The full basement is partially finished and offers plenty of potential. Located next to

    Craig Milton Re/Max Valley Shore

    11 Bishop Rd, Chester, CT 06412
  • 10 Old County Rd, Chester, CT 06412

    $900,000 Sold Mar 24, 2025

    • 2,755 Sq Ft
    • $327/SF
    • 26 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1998

    10 Old County Rd, Chester, CT 06412

    Private and peaceful with seasonal views of the Connecticut River yet less than two miles to fabulous Chester Village with shops, restaurants, art galleries, spectacular (in season) farmers market and more. This 4-bedroom custom built home has a wonderful floor plan consisting of 4 bedrooms, 3 1/2 baths, 9' ceilings, huge primary bedroom with cathedral ceilings, oversized ensuite full bath and

    Susan Malan William Pitt Sotheby's Int'l

    10 Old County Rd, Chester, CT 06412
  • 71 Maple St, Chester, CT 06412

    $540,000 Sold Mar 20, 2025

    • 2,144 Sq Ft
    • $252/SF
    • 172 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1980

    71 Maple St, Chester, CT 06412

    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

    Louisa Ketron Berkshire Hathaway NE Prop.

    71 Maple St, Chester, CT 06412
  • 15 Kirtland Terrace, Chester, CT 06412

    $280,000 Sold Mar 07, 2025

    • 1,170 Sq Ft
    • $239/SF
    • 3 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1951

    15 Kirtland Terrace, Chester, CT 06412

    Nestled at the end of a quiet street, this 3-bedroom, 1.5-bath ranch offers a rare chance to create your dream home in historic Chester. Overlooking the serene Chester Fairgrounds fields, this property features stunning views and a spacious lot, making it ideal for renovation or a fresh new build. With easy one-floor living and central air, this home offers comfort and convenience. Whether you

    Kristina Quinones William Pitt Sotheby's Int'l

    15 Kirtland Terrace, Chester, CT 06412
  • 261 Middlesex Ave, Chester, CT 06412

    $360,000 Sold Feb 25, 2025

    • 1,248 Sq Ft
    • $288/SF
    • 36 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1935

    261 Middlesex Ave, Chester, CT 06412

    Come & enjoy all that Chester has to offer! Chester is one of the most sought after Connecticut village towns! This sweet Colonial built in 1935 is set back from the road on 2 picturesque acres of land offering plenty of expansion possibilities! Family owned since 1935. First floor offers a living room with stone fireplace, a dining room, a kitchen & mud room. All original hardwood floors

    Theresa Bitondo Berkshire Hathaway NE Prop.

    261 Middlesex Ave, Chester, CT 06412
  • 67 W Main St, Chester, CT 06412

    $637,500 Sold Jan 31, 2025

    • 1,916 Sq Ft
    • $333/SF
    • 8 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1917

    67 W Main St, Chester, CT 06412

    Chester Village...a home you will love! Designed with natural grace and style, the timeless simplicity of this Quintessential New England Arts & Crafts style home offers the perfect blend of traditional architectural features with modern home design. Lovingly restored by the current owners, a welcoming front porch leads to a gracious entryway and elegant well-proportioned rooms that blend

    Kyle Hinding Coldwell Banker Realty

    67 W Main St, Chester, CT 06412
  • 96 Middlesex Ave, Chester, CT 06412

    $1,300,000 Sold Jan 31, 2025

    • 3,153 Sq Ft
    • $412/SF
    • 162 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1830

    96 Middlesex Ave, Chester, CT 06412

    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.

    Susan Malan William Pitt Sotheby's Int'l

    96 Middlesex Ave, Chester, CT 06412
  • 2 Sypher Rd, Chester, CT 06412

    $450,000 Sold Jan 24, 2025

    • 2,278 Sq Ft
    • $198/SF
    • 66 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1970

    2 Sypher Rd, Chester, CT 06412

    Welcome to 2 Sypher Rd. Chester! Tucked away in the peaceful woods of Chester near Cedar Lake, this charming 2,278 sq ft, 4-bedroom, 2.5-bath colonial rests on a picturesque 2-acre lot. Inside, you'll find hardwood floors throughout and a beautifully remodeled kitchen with soft-close cabinets, Corian countertops, and stainless steel appliances. The spacious living room, complete with a cozy

    Stacey Wyeth William Pitt Sotheby's Int'l

    2 Sypher Rd, Chester, CT 06412
  • 5 Marina View Dr, Chester, CT 06412

    $500,000 Sold Jan 17, 2025

    • 2,037 Sq Ft
    • $245/SF
    • 81 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1993

    5 Marina View Dr, Chester, CT 06412

    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.

    Susan Malan William Pitt Sotheby's Int'l

    5 Marina View Dr, Chester, CT 06412
  • 39 Castle View Dr, Chester, CT 06412

    $419,900 Sold Jan 07, 2025

    • 2,208 Sq Ft
    • $190/SF
    • 95 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2013

    39 Castle View Dr, Chester, CT 06412

    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

    Gene Pica RE/MAX Alliance

    39 Castle View Dr, Chester, CT 06412

Showing Results 81 - 120, Page 3 of 18

Connecticut Middlesex County Chester

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