Chester, CT Homes

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  /6

  $145,000

  Under Contract

  • Land
  • 4.91 Acres
  • $29,532 per Acre

  0 Goose Hill Rd Unit 24180404, Chester, CT 06412

  New to the market! Discover the perfect canvas for your dream home on this beautiful, private 4.91-acre wooded lot. Nestled within a private 8-lot subdivision just off Goose Hill Road, this parcel offers a rare blend of ultimate privacy and convenience, featuring excellent frontage on a paved, private road. The location is truly unbeatable, sitting just over a mile from the charming, historic

  Amy Graham William Pitt Sotheby's Int'l

  0 Goose Hill Rd Unit 24180404, Chester, CT 06412
• 

  $580,000

  Sold Dec 10, 2025

  28 S Wig Hill Rd, Chester, CT 06412

  • 2 Beds
  • 3 Baths
  • 3,091 Sq Ft
  • Built 1770

  Last Sold Summary

  • 10% Below List Price
  • $188/SF
  • 138 Days On Market

  Last Listing Agent Andrew O'Reilly Seaport Real Estate Services

  28 S Wig Hill Rd, Chester, CT 06412
• 

  Est $939,479

  Not Listed For Sale

  22 Waterhouse Ln, Chester, CT 06412

  • 3 Beds
  • 2.5 Baths
  • 3,802 Sq Ft
  • Built 1999

  22 Waterhouse Ln, Chester, CT 06412

  Last Sold Summary

  • 69 Days On Market
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  /24

  $439,900

  • 3 Beds
  • 1.5 Baths
  • 1,198 Sq Ft

  1 Kirtland Ave, Chester, CT 06412

  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

  Craig Milton Re/Max Valley Shore

  1 Kirtland Ave, Chester, CT 06412
• 

  $550,000

  Sold Oct 15, 2025

  23 Spring St, Chester, CT 06412

  • 2 Beds
  • 1.5 Baths
  • 1,104 Sq Ft
  • Built 1920

  Last Sold Summary

  • 17% Above List Price
  • $498/SF
  • 15 Days On Market

  Current Estimated Value $558,575

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

  23 Spring St, Chester, CT 06412
• 

  Est $775,616

  Not Listed For Sale

  19 Hickory Hill Dr, Chester, CT 06412

  • 3 Beds
  • 3 Baths
  • 2,646 Sq Ft
  • Built 1984

  19 Hickory Hill Dr, Chester, CT 06412

  Last Sold Summary

  • 5 Days On Market
• 

  

  /35

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  135 Middlesex Ave, Chester, CT 06412

  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

  Lisa Genovali Re/Max Valley Shore

  135 Middlesex Ave, Chester, CT 06412
• 

  $375,000

  Sold Nov 13, 2025

  50 Bokum Rd, Chester, CT 06412

  • 2 Beds
  • 1.5 Baths
  • 807 Sq Ft
  • Built 1912

  Last Sold Summary

  • 12% Below List Price
  • $465/SF
  • 59 Days On Market

  Current Estimated Value $386,516

  Last Listing Agent Cynthia Sigurdson William Pitt Sotheby's Int'l

  50 Bokum Rd, Chester, CT 06412
• 

  Est $542,071

  Not Listed For Sale

  2 Sypher Rd, Chester, CT 06412

  • 4 Beds
  • 2.5 Baths
  • 2,278 Sq Ft
  • Built 1970

  2 Sypher Rd, Chester, CT 06412

  Last Sold Summary

  • 66 Days On Market
• 

  

  /5

  $799,900

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  88 Winthrop Rd, Chester, CT 06412

  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

  Peter Walsh Re/Max Valley Shore

  88 Winthrop Rd, Chester, CT 06412
• 

  $750,000

  Sold Feb 20, 2026

  9 Hickory Hill Dr, Chester, CT 06412

  • 3 Beds
  • 2.5 Baths
  • 2,888 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Below List Price
  • $260/SF
  • 101 Days On Market

  Current Estimated Value $784,370

  Last Listing Agent Kathy Schellens William Pitt Sotheby's Int'l

  9 Hickory Hill Dr, Chester, CT 06412
• 

  Est $536,405

  Not Listed For Sale

  42 Railroad Ave, Chester, CT 06412

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft
  • Built 1954

  42 Railroad Ave, Chester, CT 06412

  Last Sold Summary

  • 117 Days On Market
• 

  $530,000

  Sold Feb 26, 2026

  131 Middlesex Ave, Chester, CT 06412

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft
  • Built 1930

  Last Sold Summary

  • 18% Below List Price
  • $319/SF
  • 158 Days On Market

  Current Estimated Value $552,981

  Last Listing Agent Claudia O'Connell William Raveis Real Estate

  131 Middlesex Ave, Chester, CT 06412
• 

  Est $515,258

  Not Listed For Sale

  16 Middlesex Ave, Chester, CT 06412

  • 3 Beds
  • 2 Baths
  • 1,963 Sq Ft
  • Built 1945

  16 Middlesex Ave, Chester, CT 06412

  Last Sold Summary

  • 59 Days On Market
• 

  $618,000

  Sold Jun 11, 2026

  81 Main St, Chester, CT 06412

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1950

  Last Sold Summary

  • 12% Above List Price
  • $548/SF
  • 4 Days On Market

  Current Estimated Value $548,335

  Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

  81 Main St, Chester, CT 06412
• 

  Est $642,817

  Not Listed For Sale

  8 Hickory Hill Dr, Chester, CT 06412

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1984

  8 Hickory Hill Dr, Chester, CT 06412

  Last Sold Summary

  • 1 Day On Market
• 

  $875,000

  Sold Jul 25, 2025

  79 Cedar Lake Rd, Chester, CT 06412

  • 4 Beds
  • 3 Baths
  • 3,206 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Below List Price
  • $273/SF
  • 83 Days On Market

  Current Estimated Value $919,468

  Last Listing Agent Bill Heenan William Raveis Real Estate

  79 Cedar Lake Rd, Chester, CT 06412
• 

  Est $1,005,906

  Not Listed For Sale

  15 Gilbert Hill Rd, Chester, CT 06412

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

  15 Gilbert Hill Rd, Chester, CT 06412

  Last Sold Summary

  • 18 Days On Market
• 

  $252,500

  Sold Nov 17, 2025

  21 E Liberty St, Chester, CT 06412

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft
  • Built 1954

  Last Sold Summary

  • 28% Below List Price
  • $250/SF
  • 26 Days On Market

  Current Estimated Value $291,361

  Last Listing Agent Rachel Welch William Raveis Real Estate

  21 E Liberty St, Chester, CT 06412
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  Est $640,869

  Not Listed For Sale

  67 W Main St, Chester, CT 06412

  • 3 Beds
  • 1.5 Baths
  • 1,916 Sq Ft
  • Built 1917

  67 W Main St, Chester, CT 06412

  Last Sold Summary

  • 8 Days On Market
• 

  $470,000

  Sold Jun 12, 2026

  19 Castle View Dr, Chester, CT 06412

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Above List Price
  • $430/SF
  • 13 Days On Market

  Current Estimated Value $394,926

  Last Listing Agent Donna Genovese Great Estates, CT

  19 Castle View Dr, Chester, CT 06412
• 

  Est $792,127

  Not Listed For Sale

  17 Kings Hwy, Chester, CT 06412

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft
  • Built 1988

  17 Kings Hwy, Chester, CT 06412

  Last Sold Summary

  • 36 Days On Market
• 

  $225,000

  Sold Jun 10, 2026

  11 Kings Hwy, Chester, CT 06412

  • Land
  • 1.5 Acres
  • $150,000 per Acre

  Last Sold Summary

  • 13% Above List Price
  • 1,286 Days On Market

  Last Listing Agent Rachel Welch William Raveis Real Estate

  11 Kings Hwy, Chester, CT 06412
• 

  Est $546,512

  Not Listed For Sale

  45 Winthrop Rd, Chester, CT 06412

  • 4 Beds
  • 3 Baths
  • 1,972 Sq Ft
  • Built 1985

  45 Winthrop Rd, Chester, CT 06412

  Last Sold Summary

  • 60 Days On Market
• 

  $1,017,000

  Sold Oct 20, 2025

  95 Cedar Swamp Rd, Chester, CT 06412

  • 4 Beds
  • 3.5 Baths
  • 4,341 Sq Ft
  • Built 1999

  Last Sold Summary

  • $234/SF
  • 53 Days On Market

  Current Estimated Value $1,081,090

  Last Listing Agent Rachel Welch William Raveis Real Estate

  95 Cedar Swamp Rd, Chester, CT 06412
• 

  Est $522,725

  Not Listed For Sale

  24 E Liberty St, Chester, CT 06412

  • 4 Beds
  • 2 Baths
  • 1,926 Sq Ft
  • Built 1790

  24 E Liberty St, Chester, CT 06412

  Last Sold Summary

  • 13 Days On Market
• 

  $635,000

  Sold Apr 30, 2026

  1 Ferry Rd, Chester, CT 06412

  • 3 Beds
  • 3 Baths
  • 2,752 Sq Ft
  • Built 1790

  Last Sold Summary

  • 7% Below List Price
  • $231/SF
  • 86 Days On Market

  Current Estimated Value $643,683

  Last Listing Agent Jennifer D'Amato Real Broker CT, LLC

  1 Ferry Rd, Chester, CT 06412
• 

  Est $310,769

  Not Listed For Sale

  187 Middlesex Ave, Chester, CT 06412

  • 3 Beds
  • 1 Bath
  • 1,194 Sq Ft
  • Built 1965

  187 Middlesex Ave, Chester, CT 06412

  Last Sold Summary

  • 58 Days On Market
• 

  $695,000

  Sold Jul 02, 2026

  59 Wig Hill Rd, Chester, CT 06412

  • 5 Beds
  • 2.5 Baths
  • 3,862 Sq Ft
  • Built 1977

  Last Sold Summary

  • 4% Below List Price
  • $180/SF
  • 43 Days On Market

  Current Estimated Value $741,548

  Last Listing Agent Joseph Kelly William Pitt Sotheby's Int'l

  59 Wig Hill Rd, Chester, CT 06412
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  Est $516,383

  Not Listed For Sale

  6 Hickory Hill Dr, Chester, CT 06412

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft
  • Built 1964

  6 Hickory Hill Dr, Chester, CT 06412

  Last Sold Summary

  • 1 Day On Market
• 

  $975,000

  Sold Nov 17, 2025

  7 Old Depot Rd, Chester, CT 06412

  • 4 Beds
  • 2.5 Baths
  • 3,149 Sq Ft
  • Built 1908

  Last Sold Summary

  • 25% Below List Price
  • $310/SF
  • 236 Days On Market

  Current Estimated Value $1,005,095

  Last Listing Agent Colette Harron William Pitt Sotheby's Int'l

  7 Old Depot Rd, Chester, CT 06412
• 

  Est $457,812

  Not Listed For Sale

  3 Cross Rd, Chester, CT 06412

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1966

  3 Cross Rd, Chester, CT 06412

  Last Sold Summary

  • 48 Days On Market
• 

  $495,000

  Sold Jun 05, 2026

  275 W Main St, Chester, CT 06412

  • 4 Beds
  • 2 Baths
  • 1,906 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Above List Price
  • $260/SF
  • 6 Days On Market

  Current Estimated Value $494,704

  Last Listing Agent Kelly Puorro Puorro Realty Group

  275 W Main St, Chester, CT 06412
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  Est $2,325,389

  Not Listed For Sale

  49 Parkers Point Rd, Chester, CT 06412

  • 6 Beds
  • 4.5 Baths
  • 3,968 Sq Ft
  • Built 1987

  49 Parkers Point Rd, Chester, CT 06412

  Last Sold Summary

  • 29 Days On Market
• 

  $1,275,000

  Sold Dec 12, 2025

  47 Ferry Rd, Chester, CT 06412

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft
  • Built 1939

  Last Sold Summary

  • 16% Above List Price
  • $479/SF
  • 9 Days On Market

  Current Estimated Value $1,284,887

  Last Listing Agent Mary Poola William Raveis Real Estate

  47 Ferry Rd, Chester, CT 06412
• 

  Not Listed For Sale

  19 W Main St, Chester, CT 06412

  • 4 Beds
  • 3.5 Baths
  • 4,205 Sq Ft
  • Built 1999

  19 W Main St, Chester, CT 06412

  Last Sold Summary

  • 136 Days On Market
• 

  $780,000

  Sold Jan 15, 2026

  35 Maple St, Chester, CT 06412

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft
  • Built 1765

  Last Sold Summary

  • 2% Below List Price
  • $440/SF
  • 52 Days On Market

  Current Estimated Value $785,244

  Last Listing Agent Deborah Rowe William Raveis Real Estate

  35 Maple St, Chester, CT 06412
• 

  Est $519,419

  Not Listed For Sale

  56 Castle View Dr, Chester, CT 06412

  • 3 Beds
  • 3 Baths
  • 2,268 Sq Ft
  • Built 1963

  56 Castle View Dr, Chester, CT 06412

  Last Sold Summary

  • 40 Days On Market
• 

  $695,000

  Sold May 15, 2026

  226 Middlesex Ave, Chester, CT 06412

  • 4 Beds
  • 2.5 Baths
  • 2,029 Sq Ft
  • Built 1976

  Last Sold Summary

  • $343/SF
  • 30 Days On Market

  Current Estimated Value $691,497

  Last Listing Agent Peg Mitchel Coldwell Banker Realty

  226 Middlesex Ave, Chester, CT 06412
• 

  Est $1,187,420

  Not Listed For Sale

  25 Gilbert Hill Rd, Chester, CT 06412

  • 4 Beds
  • 4.5 Baths
  • 3,351 Sq Ft
  • Built 1987

  25 Gilbert Hill Rd, Chester, CT 06412

  Last Sold Summary

  • 16 Days On Market

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