Chester, CT Homes

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  $685,000

  • 3 Beds
  • 3 Baths
  • 2,752 Sq Ft

  1 Ferry Rd, Chester, CT 06412

  An extraordinary offering in one of Connecticut's most beloved river towns. Stunning sunrises over unobstructed views of Chester Creek sets the tone for this rare piece of Chester history. The Bani Denison homestead dates to 1781 and once served as Chester's first post office. Thoughtfully restored, this classic embankment Colonial with Dutch kick gambrel style roof offers modern amenities while

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (860) 454-6525

  1 Ferry Rd, Chester, CT 06412
• Explore Chester

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  /16

  $2,400 total monthly price

  • 4 Beds
  • 1 Bath
  • 1,462 Sq Ft
  • Townhouse for Rent

  53 Main St, Deep River, CT 06417

  Property Id: 2300089Welcome to this charming 4 bedroom, 1 bathroom townhouse in Deep River, CT. This lovely home features a fenced yard, washer/dryer in unit, and is pet-friendly for cats and dogs. Enjoy the convenience of included utilities and modern amenities. Don't miss out on this opportunity!

  53 Main St, Deep River, CT 06417
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  $1,000,050 Sold Jun 25, 2025

  15 Gilbert Hill Rd, Chester, CT 06412

  • 4 Beds
  • 3 Baths
  • 3,054 Sq Ft
  • Built 1950

  Last Sold Summary

  • 22% Above List Price
  • $327/SF
  • 18 Days On Market

  Current Estimated Value $998,361

  Last Listing Agent Angela Ruel Berkshire Hathaway NE Prop.

  15 Gilbert Hill Rd, Chester, CT 06412
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  Est $898,052 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,033 Sq Ft

  75 Pinnacle Ln, Chester, CT 06412

  75 Pinnacle Ln, Chester, CT 06412
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  $549,000

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft

  131 Middlesex Ave, Chester, CT 06412

  Discover this waterfront delight in charming Chester, rewarding with year-round views! Completely renovated in 2012 from the ground up (including brand new septic system), this pristine Colonial offers 3 floors of living space and a smart L-shape open floor plan ensuring that you always have a gorgeous view. In addition to some hardworking 1st floor spaces (roomy mudroom, full bath and laundry

  

  Claudia O'Connell

  William Raveis Real Estate

  (860) 590-3562

  131 Middlesex Ave, Chester, CT 06412
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  /19

  $2,600 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • House for Rent

  48 E Kings Hwy, Chester, CT 06412

  Freshly painted apartment with all new kitchen appliances on quiet residential street a short distance to Chester Village. Close to Rt 9 providing access to Middletown, Hartford to the north and Old Saybrook and Amtrak station to the south. This apartment is roomy, comfortable and provides the very best in convenient living. This duplex with the two units each have one car attached garages. The

  Richard Greene Coldwell Banker Realty

  48 E Kings Hwy, Chester, CT 06412
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  $760,000 Sold Nov 03, 2025

  28 Hoop Pole Hill Rd, Chester, CT 06412

  • 4 Beds
  • 3.5 Baths
  • 3,396 Sq Ft
  • Built 2008

  Last Sold Summary

  • 5% Below List Price
  • $224/SF
  • 83 Days On Market

  Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

  28 Hoop Pole Hill Rd, Chester, CT 06412
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  Est $566,032 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft

  22 Hickory Hill Dr, Chester, CT 06412

  22 Hickory Hill Dr, Chester, CT 06412
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  $850,000

  • 4 Beds
  • 2 Baths
  • 8,382 Sq Ft

  26 Ferry Rd, Chester, CT 06412

  Located in the Town of Chester, this mixed-use property presents a rare opportunity to acquire a distinctive asset in one of Connecticut's most desirable markets. As it stands, the property consists of approximately 5,000 square feet of commercial space, including one loading dock, three (3) garages, and an oversized on-site parking lot, supporting a wide range of operational and occupancy needs.

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1600

  26 Ferry Rd, Chester, CT 06412
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  /3

  $2,400 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,190 Sq Ft
  • House for Rent

  17 Pratt St, Chester, CT 06412

  Welcome to your new home in the heart of Chester Center, CT! This charming property offers a comfortable living space perfect for those looking for convenience and style. Embrace the vibrant lifestyle with several outstanding restaurants just a stone's throw away, ensuring you’ll always have delightful dining options at your fingertips.The residence features well-appointed bedrooms and

  17 Pratt St, Chester, CT 06412
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  $540,000 Sold Mar 20, 2025

  71 Maple St, Chester, CT 06412

  • 2 Beds
  • 1.5 Baths
  • 2,144 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $252/SF
  • 172 Days On Market

  Current Estimated Value $599,154

  Last Listing Agent Louisa Ketron Berkshire Hathaway NE Prop.

  71 Maple St, Chester, CT 06412
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  Est $424,453 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  8 Winthrop Rd, Chester, CT 06412

  8 Winthrop Rd, Chester, CT 06412
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  $200,000

  • Land
  • 2.25 Acres
  • $88,889 per Acre

  43 Bokum Rd, Chester, CT 06412

  Beautiful potential building lot. Access via Private road, 2.25 acres. Undeveloped.

  Nicholas Tomanelli Coldwell Banker Realty

  43 Bokum Rd, Chester, CT 06412
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  /20

  $2,200 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft
  • House for Rent

  15 Laurel St, Chester, CT 06412

  Three-bedroom rental featuring one full bathroom, a private back patio, and an attached one-car garage. The lower level is partially finished, offering additional living or storage space. Located near Cedar Lake, this home includes new double-paned, energy-efficient windows throughout. Credit and background/criminal checks are required with application submission.

  Craig Milton Re/Max Valley Shore

  15 Laurel St, Chester, CT 06412
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  $420,000 Sold Sep 24, 2025

  14 Ferry Rd, Chester, CT 06412

  • 4 Beds
  • 1.5 Baths
  • 2,025 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Above List Price
  • $207/SF
  • 35 Days On Market

  Current Estimated Value $407,532

  Last Listing Agent Ian Sacks Coldwell Banker Realty

  14 Ferry Rd, Chester, CT 06412
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  Est $455,245 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,771 Sq Ft

  41 Railroad Ave, Chester, CT 06412

  41 Railroad Ave, Chester, CT 06412
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  $319,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  12 Deep Hollow Rd, Chester, CT 06412

  Enjoy convenient one level living on a quiet, charming dead-end street just steps from Chester Village. This home offers a full unfinished walkout basement, vinyl siding, thermal windows, and a 200-amp electrical panel. A new furnace was installed in 2019. The neighborhood is truly exceptional, residents are unbelievably kind and feel like family. With a little TLC, this property is ready for

  Craig Milton Re/Max Valley Shore

  12 Deep Hollow Rd, Chester, CT 06412
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  /17

  $1,950 total monthly price

  • 2 Beds
  • 1 Bath
  • 790 Sq Ft
  • Apartment for Rent

  159 W Main St Unit E, Chester, CT 06412

  SPACIOUS 2 BEDROOM RANCH APARTMENT WITH NEWLY RENOVATED KITCHEN / LOCATED IN PICTURESQUE MIXED USE BUILDING / FRESHLY PAINTED WITH NEW APPLIANCES, HARDWOOD FLOORS & 9 FOOT CEILINGS / MAIN BEDROOM HAS WALKIN CLOSET / ENJOY HIKING & LIVING NEXT TO "NORTH QUARTER PARK" AND THE CONVENIENCE OF BEAUTIFUL DOWNTOWN CHESTER

  Tom Clancy William Pitt Sotheby's Int'l

  159 W Main St Unit E, Chester, CT 06412
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  $180,000 Sold May 09, 2025

  93 W Main St, Chester, CT 06412

  • 1 Bed
  • 1 Bath
  • 752 Sq Ft
  • Built 1955

  Last Sold Summary

  • 5% Below List Price
  • $239/SF
  • 32 Days On Market

  Current Estimated Value $200,882

  Last Listing Agent Kelly Puorro Puorro Realty Group

  93 W Main St, Chester, CT 06412
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  Est $1,204,607 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,862 Sq Ft

  248 Middlesex Ave, Chester, CT 06412

  248 Middlesex Ave, Chester, CT 06412
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  $779,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,888 Sq Ft

  9 Hickory Hill Dr, Chester, CT 06412

  Welcome to 9 Hickory Hill Drive! Set high on a hill in the heart of the charming Connecticut River Village of Chester. This striking Contemporary offers over 2800 sqft. of light-filled living space on 1.23 private acres-just a 3/10 mi stroll to Main St. The inviting foyer opens to a stunning, sun-drenched living area with skylights and gleaming hardwood floors throughout the living room, dining

  Kathy Schellens William Pitt Sotheby's Int'l

  9 Hickory Hill Dr, Chester, CT 06412
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  $7,500 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 4,708 Sq Ft
  • House for Rent

  15 Liberty St, Chester, CT 06412

  Exceptional Rental Opportunity in Chester's Quintessential New England Village. Experience refined living in this estate-like setting, exquisitely furnished and thoughtfully remodeled to the highest standards. Offering over 4,000 sq. ft. of light-filled luxury, this stunning home is available October 2025 through mid-May 2026. Property Highlights: 4 Bedrooms | 5 Baths - including an

  Lynn Lehrman Re/Max Valley Shore

  15 Liberty St, Chester, CT 06412
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  $975,000 Sold Apr 30, 2025

  6 Old County Rd, Chester, CT 06412

  • 4 Beds
  • 2.5 Baths
  • 2,680 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Above List Price
  • $364/SF
  • 5 Days On Market

  Current Estimated Value $994,363

  Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

  6 Old County Rd, Chester, CT 06412
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  Est $503,179 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  37 Castle View Dr, Chester, CT 06412

  37 Castle View Dr, Chester, CT 06412
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  $725,000

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft

  6 W Main St, Chester, CT 06412

  EXCELLENT LOCATION, EXCELLENT CONDITION! Lovingly restored 2-family in the heart of Chester Village with historic provenance. Perfect blend of old-school New England charm and modern updates including new siding, full insulation, and A/C. PRIME VILLAGE LOCATION - walk to Chester's vibrant fairs, events, dining, and shopping. Easy commute to Rt. 9. BOTH UNITS FEATURE: * 2 bedrooms with original

  MJ Derisio William Pitt Sotheby's Int'l

  6 W Main St, Chester, CT 06412
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  $280,000 Sold Mar 07, 2025

  15 Kirtland Terrace, Chester, CT 06412

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft
  • Built 1951

  Last Sold Summary

  • 24% Above List Price
  • $239/SF
  • 3 Days On Market

  Current Estimated Value $241,429

  Last Listing Agent Kristina Quinones William Pitt Sotheby's Int'l

  15 Kirtland Terrace, Chester, CT 06412
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  Est $584,339 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  25 Deep Hollow Rd, Chester, CT 06412

  25 Deep Hollow Rd, Chester, CT 06412
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  $232,500

  • Land
  • 1.5 Acres
  • $155,000 per Acre

  11 Kings Hwy, Chester, CT 06412

  1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line

  Rachel Welch William Raveis Real Estate

  11 Kings Hwy, Chester, CT 06412
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  $1,250,000 Sold May 02, 2025

  16 Waterhouse Ln, Chester, CT 06412

  • 4 Beds
  • 4.5 Baths
  • 4,661 Sq Ft
  • Built 1988

  Last Sold Summary

  • $268/SF
  • 24 Days On Market

  Current Estimated Value $1,299,631

  Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

  16 Waterhouse Ln, Chester, CT 06412
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  Est $633,919 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  16 Ridge Rd, Chester, CT 06412

  16 Ridge Rd, Chester, CT 06412
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  /40

  $799,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  35 Maple St, Chester, CT 06412

  Steps to the Village! Vintage 1765 Cape with many updates but still true to the original charm of the Joseph Shipman House. Two staircases, 4 working firplaces, King's Board floors, wonderful floorplan and an up-to-date kitchen makes this home a step back in time but with the amenities of today. Quartz countertops and a complete kitchen renovation in 2017. New rear pressure treated deck in 2017.

  Deborah Rowe William Raveis Real Estate

  35 Maple St, Chester, CT 06412
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  $860,000 Sold Sep 17, 2025

  25 Spring St, Chester, CT 06412

  • 3 Beds
  • 2.5 Baths
  • 2,344 Sq Ft
  • Built 1860

  Last Sold Summary

  • 4% Below List Price
  • $367/SF
  • 38 Days On Market

  Current Estimated Value $864,178

  Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

  25 Spring St, Chester, CT 06412
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  Est $543,595 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  4 Turkey Hill Rd, Chester, CT 06412

  4 Turkey Hill Rd, Chester, CT 06412
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  $745,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  8 Butter Jones Rd, Chester, CT 06412

  Enchanting Cape with Artisan Post & Beam Charm - Just Down the Road from Chester Village! Tucked away on 2 acres of picturesque land, this whimsical 3-bedroom, 2.5-bath Cape Cod home invites you to live among nature in style. Only a short distance from Cedar Lake and Chester Village, you'll have easy access to endless outdoor adventures and world-class restaurants and shopping just moments away.

  Amy Graham William Pitt Sotheby's Int'l

  8 Butter Jones Rd, Chester, CT 06412
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  $442,500 Sold Oct 20, 2025

  30 Bokum Rd, Chester, CT 06412

  • 3 Beds
  • 2 Baths
  • 1,198 Sq Ft
  • Built 1930

  Last Sold Summary

  • 4% Above List Price
  • $369/SF
  • 59 Days On Market

  Last Listing Agent Max Gill Puorro Realty Group

  30 Bokum Rd, Chester, CT 06412
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  Est $729,794 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,713 Sq Ft

  12 Liberty St, Chester, CT 06412

  12 Liberty St, Chester, CT 06412
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  $449,000

  • 2 Beds
  • 1 Bath
  • 1,470 Sq Ft

  79 Middlesex Ave, Chester, CT 06412

  Charming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends timeless New England character with everyday comfort and walk-to-village convenience. Warm hardwood floors flow throughout the light-filled living room into the updated kitchen with its beautiful bow window and dining area. The kitchen is replete with ample granite counters, perfect for the aspiring chef! The

  Gigi Giordano Taylor Compass Connecticut, LLC

  79 Middlesex Ave, Chester, CT 06412
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  $795,000 Sold Jul 31, 2025

  80 W Main St, Chester, CT 06412

  • 3 Beds
  • 2 Baths
  • 2,389 Sq Ft
  • Built 1835

  Last Sold Summary

  • 14% Above List Price
  • $333/SF
  • 3 Days On Market

  Current Estimated Value $778,340

  Last Listing Agent Mary Jean Agostini RE/MAX Right Choice

  80 W Main St, Chester, CT 06412
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  Est $422,450 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  230 W Main St, Chester, CT 06412

  230 W Main St, Chester, CT 06412
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  /2

  $209,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  19 Castle View Dr, Chester, CT 06412

  Investor/Builder Opportunity! Discover a rare opportunity in charming Chester, Connecticut! Minutes from Chester's vibrant village center known for its restaurants, boutiques, galleries, theater and farmer's market. This property offers tremendous potential for the right buyer. The existing structure is not currently habitable! This property require significant renovation/demolition due its

  Sharon Linder Berkshire Hathaway NE Prop.

  19 Castle View Dr, Chester, CT 06412

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