Middlesex, CT Homes

• 

  Est $486,940 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,963 Sq Ft

  16 Middlesex Ave, Chester, CT 06412

  16 Middlesex Ave, Chester, CT 06412
• 

  $1,250,000 Sold May 02, 2025

  • 4,661 Sq Ft
  • $268/SF
  • 24 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1988

  16 Waterhouse Ln, Chester, CT 06412

  Discover the essence of elegance and tranquility in this exquisite Chester estate, boasting a host of 2024 upgrades including a new roof, furnace, and a tastefully renovated half bath. This property also comes with an approved separate building lot, enhancing your privacy and offering potential investment opportunities. The home is perfectly oriented to capture the morning sunrises, providing

  Teri Strain-Lewis William Pitt Sotheby's Int'l

  16 Waterhouse Ln, Chester, CT 06412
• 

  Est $571,851 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft

  8 Hickory Hill Dr, Chester, CT 06412

  8 Hickory Hill Dr, Chester, CT 06412
• 

  $675,000 Sold May 01, 2025

  • 4,056 Sq Ft
  • $166/SF
  • 65 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2002

  108 Middlesex Ave, Chester, CT 06412

  Welcome to 108 Middlesex Ave. A multi family Colonial income producing property in the heart of Chester! The home was built in 2002, and in 2006 an attached accessory dwelling unit / inlaw apartment was added and is now occupied at $2,000 a month. The main house features a bright and inviting layout with hardwood floors, a cozy fireplace in the living room and sliders from the dining room out to

  Trever Smith Chiarito Real Estate LLC

  108 Middlesex Ave, Chester, CT 06412
• 

  Est $367,782 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  47 Winthrop Rd, Chester, CT 06412

  47 Winthrop Rd, Chester, CT 06412
• 

  $975,000 Sold Apr 30, 2025

  • 2,680 Sq Ft
  • $364/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2002

  6 Old County Rd, Chester, CT 06412

  Private, pristine, and with proximity to the Connecticut River, many wonderful restaurants, and boutiques. This meticulously maintained four bedroom 2 1/2 bath home is less than 2 miles from fabulous Chester Village. Set on over 2 acres this beautiful home has been carefully updated and enhanced. The meandering driveway takes you to a perfectly sited home with an amazing heated barn which also

  Susan Malan William Pitt Sotheby's Int'l

  6 Old County Rd, Chester, CT 06412
• 

  Est $734,134 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,343 Sq Ft

  17 Wig Hill Rd, Chester, CT 06412

  17 Wig Hill Rd, 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
• 

  Est $716,823 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  17 Kings Hwy, Chester, CT 06412

  17 Kings Hwy, 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
• 

  Est $461,593 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,972 Sq Ft

  45 Winthrop Rd, Chester, CT 06412

  45 Winthrop 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
• 

  Est $377,179 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  54 Bokum Rd, Chester, CT 06412

  54 Bokum 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
• 

  Est $538,806 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,927 Sq Ft

  24 Deep Hollow Rd, Chester, CT 06412

  24 Deep Hollow Rd, 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
• 

  Est $419,790 Not Listed For Sale

  • 6 Beds
  • 2 Baths
  • 2,638 Sq Ft

  53 Main St, Deep River, CT 06417

  53 Main St, Deep River, CT 06417
• 

  $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
• 

  Est $463,118 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft

  6 Hickory Hill Dr, Chester, CT 06412

  6 Hickory Hill Dr, 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
• 

  Est $407,307 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  3 Cross Rd, Chester, CT 06412

  3 Cross Rd, 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
• 

  Est $665,699 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,422 Sq Ft

  123 Goose Hill Rd, Chester, CT 06412

  123 Goose Hill Rd, 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
• 

  Est $2,156,937 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,968 Sq Ft

  49 Parkers Point Rd, Chester, CT 06412

  49 Parkers Point 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
• 

  Est $907,876 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,363 Sq Ft

  83 Main St, Chester, CT 06412

  83 Main St, 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
• 

  Est $618,293 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,178 Sq Ft

  21 Baker Rd, Chester, CT 06412

  21 Baker Rd, 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
• 

  Est $624,327 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,936 Sq Ft

  7 Waterhouse Ln, Chester, CT 06412

  7 Waterhouse Ln, Chester, CT 06412
• 

  $430,000 Sold Nov 27, 2024

  • 2,268 Sq Ft
  • $190/SF
  • 40 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1963

  56 Castle View Dr, Chester, CT 06412

  Welcome to your dream home! This home features an open floor plan that seamlessly connects living spaces, perfect for both entertaining and everyday living, cozy front porch, perfect for relaxing and enjoying your morning cup of coffee, spacious 2nd floor primary bedroom suite with full bathroom and walk in closet, 4 generous sized bedrooms all with large closets. Enjoy the beauty of hardwood

  Sharon Linder Berkshire Hathaway NE Prop.

  56 Castle View Dr, Chester, CT 06412
• 

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,974 Sq Ft

  19 Parkers Point Rd, Chester, CT 06412

  19 Parkers Point Rd, Chester, CT 06412
• 

  $582,000 Sold Nov 21, 2024

  • 2,398 Sq Ft
  • $243/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1870

  28 Goose Hill Rd, Chester, CT 06412

  Step into history with this 1870 colonial home on over 1.5 acres. Featuring three bedrooms and two fully finished bathrooms, plus a third en suite awaiting your touch, this property is a canvas for your creativity. Enjoy high ceilings on the first floor, bathed in natural light from large windows that create a warm and inviting atmosphere. Relax on the front porch or in the screened-in back

  Cheryl Bergeron-Lucca LPT Realty - IConn Team

  28 Goose Hill Rd, Chester, CT 06412
• 

  Est $378,778 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,362 Sq Ft

  30 Middlesex Ave, Chester, CT 06412

  30 Middlesex Ave, Chester, CT 06412
• 

  $189,900 Sold Nov 08, 2024

  • 616 Sq Ft
  • $308/SF
  • 48 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1946

  11 Laurel St, Chester, CT 06412

  Seasonal 2 bedroom Cottage. Large Lot. Potential for year round conversion. Or simply update it for your own summer getaway!

  Craig Milton Re/Max Valley Shore

  11 Laurel St, Chester, CT 06412
• 

  Est $659,962 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,532 Sq Ft

  109 Main St, Chester, CT 06412

  109 Main St, Chester, CT 06412
• 

  $276,000 Sold Oct 30, 2024

  • 1,200 Sq Ft
  • $230/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  4 Bates Rd, Chester, CT 06412

  This classic ranch sits on a dead end street, close to downtown and less than a minute from the local elementary school. This home has an easy, useable floor plan and a private backyard on a road of similar homes. Original kitchen and simple fixtures throughout, the home does have central air and nothing but upside potential. This is an as-is sale. Note, the roof is not insurable and showing

  Cara Bernard Coldwell Banker Realty

  4 Bates Rd, Chester, CT 06412
• 

  Est $495,009 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  8 School Ln, Chester, CT 06412

  8 School Ln, Chester, CT 06412
• 

  $225,000 Sold Oct 25, 2024

  • 1,194 Sq Ft
  • $188/SF
  • 58 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  187 Middlesex Ave, Chester, CT 06412

  Come enjoy all Chester has to offer. Make this 3 bedroom 1 bathroom house your home. Town has a vibrant community and offers many amenities such as quaint shops, amazing restaurants, parks and is conveniently located between New York and Boston. Insured w/ Escrow(IE). FHA Case #061-400225. Eligible Bidders: Owner Occupants, Nonprofits,and Government Agencies only

  Team DAnna Statewide Premier Prop. LLC

  187 Middlesex Ave, Chester, CT 06412

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