Old Saybrook, CT Homes

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  $893,500 Sold Dec 05, 2025

  55 Cypress Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $466/SF
  • 21 Days On Market

  Current Estimated Value $914,232

  Last Listing Agent Tammy Tinnerello William Pitt Sotheby's Int'l

  55 Cypress Rd, Old Saybrook, CT 06475
• 

  Est $602,049 Not Listed For Sale

  367 Main St Unit 4, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • Built 1980

  367 Main St Unit 4, Old Saybrook, CT 06475

  Last Sold Summary

  • 12% Above List Price
  • $515/SF
  • 4 Days On Market

  Last Sold Price $536,999

  Last Listing Agent Debbie Lupo The Agency
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  /40

  $4,250,000

  • 6 Beds
  • 4.5 Baths
  • 5,536 Sq Ft

  41 Watrous Point Rd, Old Saybrook, CT 06475

  Presenting a single level light-filled mid-century modern masterpiece, set on a prominent 2.7 acre private waterfront peninsula! Enjoy 875' of frontage along the CT River and adjacent Turtle Creek nature preserve. This dreamlike property comes with two docks. A deep water dock on the river, plus a second dock on Turtle Creek! Drink in views from Essex Harbor to the north, across the river to Old

  Rick Weiner William Pitt Sotheby's Int'l

  41 Watrous Point Rd, Old Saybrook, CT 06475
• 

  $520,000 Sold Jul 07, 2025

  25 Chalker Beach Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 922 Sq Ft
  • Built 1986

  Last Sold Summary

  • 10% Below List Price
  • $564/SF
  • 122 Days On Market

  Current Estimated Value $527,453

  Last Listing Agent Susan Malton Coldwell Banker Realty

  25 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  Est $1,712,222 Not Listed For Sale

  16 Fenbrook Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 4.5 Baths
  • 3,036 Sq Ft
  • Built 2007

  16 Fenbrook Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 12% Above List Price
  • $502/SF
  • 62 Days On Market

  Last Sold Price $1,525,000

  Last Listing Agent Jason Malagutti Regency Real Estate, LLC
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  /28

  $685,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  167 Ingham Hill Rd, Old Saybrook, CT 06475

  Privacy, acreage, and beach-town access converge in this 1.09-acre Ingham Hill property in Old Saybrook. Built in 1984 by Bob Day and offered for the first time by the original owner, this Colonial delivers rare space along the Connecticut Shoreline just minutes from beaches, marinas, and downtown amenities. With under 1,400 square feet, two full baths, and an attached garage, the flexible layout

  Jennifer Gurnell William Raveis Real Estate

  167 Ingham Hill Rd, Old Saybrook, CT 06475
• 

  $539,000 Sold Aug 27, 2025

  18 Lynde St, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,185 Sq Ft
  • Built 1947

  Last Sold Summary

  • 2% Below List Price
  • $455/SF
  • 43 Days On Market

  Current Estimated Value $541,338

  Last Listing Agent Liz Squillacote William Pitt Sotheby's Int'l

  18 Lynde St, Old Saybrook, CT 06475
• 

  Est $825,512 Not Listed For Sale

  5 Watch Hill Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 2,630 Sq Ft
  • Built 1980

  5 Watch Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 31% Above List Price
  • $240/SF
  • 151 Days On Market

  Last Sold Price $630,000

  Last Listing Agent Kevin Geysen William Pitt
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  /40

  $380,000 Coming Soon

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft

  13 College St, Old Saybrook, CT 06475

  Adorable seasonal beach cottage nestled in the heart of Old Saybrook! This charming 2-bedroom, 1 bath retreat offers the perfect blend of coastal charm and convenience. Enjoy the large deep back yard and outdoor shower after you return from a day at the beach. Connected to public water and ideally located just a short stroll to town, or the Saybrook Point Inn. Whether you're dreaming of summer

  Maddy Mattson Coldwell Banker Realty

  13 College St, Old Saybrook, CT 06475
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  $625,000 Sold Sep 03, 2025

  19 Hartford Ave, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 1,249 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Above List Price
  • $500/SF
  • 47 Days On Market

  Current Estimated Value $622,005

  Last Listing Agent Frank Fonteyn Prestige Realty Group

  19 Hartford Ave, Old Saybrook, CT 06475
• 

  Est $1,239,416 Not Listed For Sale

  15 Crest Rd, Old Saybrook, CT 06475

  • 5 Beds
  • 4.5 Baths
  • 2,884 Sq Ft
  • Built 1971

  15 Crest Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 10% Above List Price
  • $390/SF
  • 28 Days On Market

  Last Sold Price $1,125,000

  Last Listing Agent Sharon Linder Berkshire Hathaway Home Services
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  /25

  $575,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  18 Quarry St, Old Saybrook, CT 06475

  Downtown Old Saybrook location offers true small town charm, a first floor primary bedroom, and two full baths. Tucked away on a quiet dead end street just steps to sidewalks, this classic New England style home presents a renovation opportunity in one of the shoreline's most desirable neighborhoods. Walk to Trask Park, the Old Saybrook Library, local shops, and favorites like Walt's Market.

  Jennifer Gurnell William Raveis Real Estate

  18 Quarry St, Old Saybrook, CT 06475
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  $1,495,000 Sold Dec 01, 2025

  66 Pennywise Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 2,425 Sq Ft
  • Built 1790

  Last Sold Summary

  • 7% Above List Price
  • $616/SF
  • 1 Day On Market

  Current Estimated Value $1,413,628

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  66 Pennywise Ln, Old Saybrook, CT 06475
• 

  Est $1,024,183 Not Listed For Sale

  16 James Ct, Old Saybrook, CT 06475

  • 3 Beds
  • 3.5 Baths
  • 2,870 Sq Ft
  • Built 1995

  16 James Ct, Old Saybrook, CT 06475

  Last Sold Summary

  • 8% Above List Price
  • $331/SF
  • 20 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Colette Harron William Pitt
• 

  /2

  $695,000

  • Land
  • 1.16 Acres
  • $599,138 per Acre

  1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475

  1.25 Acres in B4 Zone. Public water available, septic required. Traffic count 15,900. Within 1/2 mile of national tenants.

  Ron Lyman Lyman Real Estate

  1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
• 

  $520,000 Sold May 16, 2025

  25 Sherman St, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,225 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $424/SF
  • 44 Days On Market

  Current Estimated Value $535,191

  Last Listing Agent Ginny Proft William Raveis Real Estate

  25 Sherman St, Old Saybrook, CT 06475
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  Est $683,419 Not Listed For Sale

  3 Pepperidge Trail, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1985

  3 Pepperidge Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 16% Above List Price
  • $242/SF
  • 38 Days On Market

  Last Sold Price $590,000

  Last Listing Agent Sharon Linder Berkshire Hathaway Home Services
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  /27

  $1,325,000 Open Sun 12PM - 3PM

  • 3 Beds
  • 1 Bath
  • 884 Sq Ft

  24 W Shore Dr, Old Saybrook, CT 06475

  Welcome to 24 W. Shore Dr., Old Saybrook, ideally located in one of Connecticut's most renowned beach communities-Cornfield Point Association. This year-round home offers the perfect blend of comfort, convenience, and stunning water views. This solid brick residence is move-in ready and features a remodeled kitchen with brand-new appliances, a sun-filled living room, three full-sized bedrooms, a

  David Rodriguez William Pitt Sotheby's Int'l

  24 W Shore Dr, Old Saybrook, CT 06475
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  $575,000 Sold Jun 20, 2025

  3 Clark Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1940

  Last Sold Summary

  • $630/SF
  • 36 Days On Market

  Current Estimated Value $595,606

  Last Listing Agent Lorenda DiMeo Century 21 AllPoints Realty

  3 Clark Ave, Old Saybrook, CT 06475
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  Est $619,693 Not Listed For Sale

  21 Middletown Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,060 Sq Ft
  • Built 1964

  21 Middletown Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 13% Above List Price
  • $517/SF
  • 302 Days On Market

  Last Sold Price $548,000

  Last Listing Agent Steven Koleno Beycome of Connecticut
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  /26

  $650,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,872 Sq Ft

  73 Knollwood Dr, Old Saybrook, CT 06475

  Welcome to Knollwood Beach Association, this ranch-style home nestled in the heart of Old Saybrook is set on a lot that includes Beamon Creek at the back edge which leads to South Cove. It boasts a full walkout basement, with exceptional potential for expansion, or customization. Inside, the home provides comfortable single level living with an easy layout. The lower-level walkout leads directly

  Rachel Welch William Raveis Real Estate

  73 Knollwood Dr, Old Saybrook, CT 06475
• 

  $505,000 Sold Jul 07, 2025

  104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475

  • 2 Beds
  • 1.5 Baths
  • 1,557 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $324/SF
  • 101 Days On Market

  Last Listing Agent Lisa Genovali Re/Max Valley Shore

  104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
• 

  Est $609,268 Not Listed For Sale

  11 Coulter St Unit 21, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 1986

  11 Coulter St Unit 21, Old Saybrook, CT 06475

  Last Sold Summary

  • 32% Above List Price
  • $297/SF
  • 43 Days On Market

  Last Sold Price $460,000

  Last Listing Agent Brian Jermainne Team Jermainne Real Estate Services, LLC
• 

  

  /31

  $699,900

  • 2 Beds
  • 1 Bath
  • 1,198 Sq Ft

  10 Edwards Rd, Old Saybrook, CT 06475

  Charming 2 bedroom ranch set on a .20 acre lot in desirable Old Saybrook Cornfield Point Beach community. This home features an open and inviting living room that flows into the dining area and beautifully remodeled kitchen, creating an ideal space for everyday living and entertaining. The updated kitchen and remodeled bathroom add modern touches while maintaining the home's comfortable charm.

  Craig Milton Re/Max Valley Shore

  10 Edwards Rd, Old Saybrook, CT 06475
• 

  $1,025,000 Sold Jul 25, 2025

  8 Cromwell Place, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,730 Sq Ft
  • Built 1957

  Last Sold Summary

  • 14% Below List Price
  • $275/SF
  • 58 Days On Market

  Current Estimated Value $1,055,066

  Last Listing Agent Roxanne Quinn Coldwell Banker Realty

  8 Cromwell Place, Old Saybrook, CT 06475
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  Est $1,671,376 Not Listed For Sale

  84 Church St, Old Saybrook, CT 06475

  • 4 Beds
  • 4 Baths
  • 3,567 Sq Ft
  • Built 2006

  84 Church St, Old Saybrook, CT 06475

  Last Sold Summary

  • 22% Above List Price
  • $385/SF
  • 6 Days On Market

  Last Sold Price $1,375,000

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  $410,000 Sold Jul 15, 2025

  6 West St, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft
  • Built 1930

  Last Sold Summary

  • 11% Below List Price
  • $496/SF
  • 111 Days On Market

  Current Estimated Value $413,762

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  6 West St, Old Saybrook, CT 06475
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  Est $744,607 Not Listed For Sale

  24 Pepperidge Trail, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 1987

  24 Pepperidge Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 10% Above List Price
  • $270/SF
  • 6 Days On Market

  Last Sold Price $680,000

  Last Listing Agent Sharon Linder Berkshire Hathaway Home Services
• 

  $962,500 Sold Mar 19, 2026

  122 Old Post Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,467 Sq Ft
  • Built 1991

  Last Sold Summary

  • 14% Below List Price
  • $390/SF
  • 158 Days On Market

  Current Estimated Value $1,053,481

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

  122 Old Post Rd, Old Saybrook, CT 06475
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  Est $611,861 Not Listed For Sale

  20 George Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1957

  20 George Dr, Old Saybrook, CT 06475

  Last Sold Summary

  • 17% Above List Price
  • $568/SF
  • 2 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  $722,500 Sold Dec 05, 2025

  5 Fox Hollow Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3 Baths
  • 2,142 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $337/SF
  • 63 Days On Market

  Current Estimated Value $727,933

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  5 Fox Hollow Rd, Old Saybrook, CT 06475
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  Est $1,504,479 Not Listed For Sale

  15 Beach View Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 3 Baths
  • 1,956 Sq Ft
  • Built 2016

  15 Beach View Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 20% Above List Price
  • $639/SF
  • 41 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Rick Weiner William Pitt
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  $993,500 Sold May 16, 2025

  11 Beach Rd E, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Below List Price
  • $603/SF
  • 43 Days On Market

  Current Estimated Value $972,949

  Last Listing Agent Kristin Davis Berkshire Hathaway NE Prop.

  11 Beach Rd E, Old Saybrook, CT 06475
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  Est $988,765 Not Listed For Sale

  15 Briarwood Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 3 Baths
  • 2,643 Sq Ft
  • Built 1958

  15 Briarwood Dr, Old Saybrook, CT 06475

  Last Sold Summary

  • 60% Above List Price
  • $233/SF
  • 4 Days On Market

  Last Sold Price $617,000

  Last Listing Agent Jennifer Gurnell William Raveis Real Estate
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  $566,000 Sold Oct 01, 2025

  14 Watrous Point Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft
  • Built 1966

  Last Sold Summary

  • 13% Below List Price
  • $263/SF
  • 3 Days On Market

  Current Estimated Value $636,531

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  14 Watrous Point Rd, Old Saybrook, CT 06475
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  Est $644,183 Not Listed For Sale

  3 Lookout Hill Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,881 Sq Ft
  • Built 1991

  3 Lookout Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 23% Above List Price
  • $279/SF
  • 59 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Coleen Brakenwagen Real Broker CT, LLC
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  $695,000 Sold Nov 21, 2025

  117 Ayers Point Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,824 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $246/SF
  • 63 Days On Market

  Current Estimated Value $717,036

  Last Listing Agent Chloe White KW Legacy Partners

  117 Ayers Point Rd, Old Saybrook, CT 06475
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  Est $791,115 Not Listed For Sale

  4 Old Colony Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1958

  4 Old Colony Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 21% Above List Price
  • $487/SF
  • 14 Days On Market

  Last Sold Price $655,000

  Last Listing Agent Ali White Coldwell Banker Realty
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  $625,000 Sold Sep 19, 2025

  3 Glen Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,915 Sq Ft
  • Built 1969

  Last Sold Summary

  • $326/SF
  • 68 Days On Market

  Current Estimated Value $632,758

  Last Listing Agent Lisa Genovali Re/Max Valley Shore

  3 Glen Dr, Old Saybrook, CT 06475
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  Not Listed For Sale

  23 Hill St, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Built 1930

  23 Hill St, Old Saybrook, CT 06475

  Last Sold Summary

  • $349/SF
  • 50 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Brian Jermainne Team Jermainne Real Estate Services, LLC

Showing Results 121 - 160, Page 4 of 18