Old Saybrook, CT Homes

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  /5

  $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.

  Ron Lyman Lyman Real Estate

  1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
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  $815,000 Sold Apr 17, 2026

  33 Fenwood Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft
  • Built 1953

  Last Sold Summary

  • 5% Below List Price
  • $399/SF
  • 9 Days On Market

  Current Estimated Value $831,653

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  33 Fenwood Rd, Old Saybrook, CT 06475
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  Est $936,304 Not Listed For Sale

  1 Boulder Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,563 Sq Ft
  • Built 1965

  1 Boulder Dr, Old Saybrook, CT 06475

  Last Sold Summary

  • 1% Below List Price
  • $369/SF
  • 6 Days On Market

  • Last Sold Price $945,000
  • Nov 01, 2024

  Last Listing Agent Suzanne McConville William Raveis Real Estate
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  /39

  $685,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,272 Sq Ft

  33 Briarwood Dr, Old Saybrook, CT 06475

  Direct waterfront living in Old Saybrook with deeded Cornfield Point beach rights and a private dock (dock in need of repair). Set on a private lot at 33 Briarwood Dr, this 3 bedroom, 2 bath residence captures expansive marsh and tidal channel views with stunning daily sunsets that define the coastal lifestyle. Out with the old and in with the new! Move-in ready with thoughtful updates including

  Jennifer Gurnell William Raveis Real Estate

  33 Briarwood Dr, Old Saybrook, CT 06475
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  $309,000 Sold Nov 04, 2025

  3 4th Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1966

  Last Sold Summary

  • 23% Below List Price
  • $358/SF
  • 143 Days On Market

  Current Estimated Value $349,388

  Last Listing Agent Phil Ledwith Century 21 AllPoints Realty

  3 4th Ave, Old Saybrook, CT 06475
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  Est $598,358 Not Listed For Sale

  4 Patterson Place, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,752 Sq Ft
  • Built 1987

  4 Patterson Place, Old Saybrook, CT 06475

  Last Sold Summary

  • 8% Above List Price
  • $317/SF
  • 60 Days On Market

  • Last Sold Price $555,000
  • Mar 28, 2025

  Last Listing Agent Lynn Lehrman RE/MAX
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  /40

  $3,695,000

  • 4 Beds
  • 4.5 Baths
  • 3,518 Sq Ft

  175 N Cove Rd, Old Saybrook, CT 06475

  An exceptional offering in the heart of North Cove, this storied estate presents a rare convergence of history, scale, and coastal prestige in Old Saybrook. Set on over an acre of beautifully sited grounds with direct water access and a private dock, the property offers a lifestyle that is both tranquil and connected, just moments from the Cove, local marinas, and the village center. The setting

  Susan Malan William Pitt Sotheby's Int'l

  175 N Cove Rd, Old Saybrook, CT 06475
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  $530,000 Sold Dec 05, 2025

  46 Maple Ave, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 3,190 Sq Ft
  • Built 1950

  Last Sold Summary

  • 18% Below List Price
  • $166/SF
  • 77 Days On Market

  Current Estimated Value $527,485

  Last Listing Agent Fran Manganello Coldwell Banker Realty

  46 Maple Ave, Old Saybrook, CT 06475
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  Est $662,271 Not Listed For Sale

  216 School House Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1960

  216 School House Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 3% Above List Price
  • $373/SF
  • 0 Days On Market

  • Last Sold Price $645,000
  • Oct 05, 2023

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  /27

  $1,325,000

  • 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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  $751,500 Sold Oct 15, 2025

  78 Hartford Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 890 Sq Ft
  • Built 1930

  Last Sold Summary

  • 12% Below List Price
  • $844/SF
  • 106 Days On Market

  Current Estimated Value $750,535

  Last Listing Agent Robert Perriello Century 21 AllPoints Realty

  78 Hartford Ave, Old Saybrook, CT 06475
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  Est $1,217,352 Not Listed For Sale

  33 Old Boston Post Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,120 Sq Ft
  • Built 1791

  33 Old Boston Post Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 6% Above List Price
  • $369/SF
  • 28 Days On Market

  • Last Sold Price $1,150,000
  • Dec 15, 2023

  Last Listing Agent Brieanne Vinyard Berkshire Hathaway Home Services
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  /25

  $650,000

  • 2 Beds
  • 2.5 Baths
  • 1,565 Sq Ft

  100 Dudley Ave Unit H42, Old Saybrook, CT 06475

  Coastal elegance meets low-maintenance living in this beautifully appointed townhouse-style 2 bedroom condominium, ideally situated within walking distance of charming downtown Old Saybrook. Located at Sheltered Cove, a coveted community, step inside an open concept floor plan with a living room showcasing custom cabinetry, fireplace and serene views of the tidal marsh that invite the outdoors

  Kirsten Adams William Pitt Sotheby's Int'l

  100 Dudley Ave Unit H42, Old Saybrook, CT 06475
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  $662,500 Sold Jun 18, 2025

  100 Sheffield St Unit D4, Old Saybrook, CT 06475

  • 2 Beds
  • 2.5 Baths
  • 2,002 Sq Ft
  • Built 1976

  Last Sold Summary

  • 2% Below List Price
  • $331/SF
  • 62 Days On Market

  Current Estimated Value $677,209

  Last Listing Agent Dawn Satagaj William Raveis Real Estate

  100 Sheffield St Unit D4, Old Saybrook, CT 06475
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  Est $2,023,425 Not Listed For Sale

  502 Main St, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,771 Sq Ft
  • Built 1988

  502 Main St, Old Saybrook, CT 06475

  Last Sold Summary

  • 8% Below List Price
  • $583/SF
  • 46 Days On Market

  • Last Sold Price $2,200,000
  • Nov 13, 2024

  Last Listing Agent Teri Lewis William Pitt
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  /15

  $551,000

  • 3 Beds
  • 3 Baths
  • 2,830 Sq Ft

  6 Watch Hill Rd, Old Saybrook, CT 06475

  Attention Investors and Motivated Home Buyers. Welcome to 6 Watch Hill. Home offers eclectic feel. New owner will build off of this design. Home boast beautiful views and you can not help but to feel peace as you appreciate all the nature around you. Great stand alone garage with wonderful workspace on 2nd level. Sale is subject to probate approval.

  Tony Martin Home Pro Real Estate

  6 Watch Hill Rd, Old Saybrook, CT 06475
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  $900,000 Sold Oct 30, 2025

  21 Wildwood Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Built 1953

  Last Sold Summary

  • 28% Below List Price
  • $639/SF
  • 171 Days On Market

  Current Estimated Value $917,252

  Last Listing Agent Marc Delise Coldwell Banker Realty

  21 Wildwood Rd, Old Saybrook, CT 06475
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  Est $706,791 Not Listed For Sale

  125 Ingham Hill Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 2,795 Sq Ft
  • Built 1700

  125 Ingham Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 9% Above List Price
  • $233/SF
  • 46 Days On Market

  • Last Sold Price $650,000
  • Dec 22, 2023

  Last Listing Agent LaurieAnn Hansen Coldwell Banker Realty
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  /31

  $699,900 Pending

  • 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
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  $595,000 Sold Mar 30, 2026

  25 Pond Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,731 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Above List Price
  • $344/SF
  • 18 Days On Market

  Current Estimated Value $587,407

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  25 Pond Rd, Old Saybrook, CT 06475
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  Est $593,200 Not Listed For Sale

  77 Chalker Beach Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,102 Sq Ft
  • Built 1937

  77 Chalker Beach Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 9% Above List Price
  • $492/SF
  • 68 Days On Market

  • Last Sold Price $542,500
  • Dec 14, 2023

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  $810,000 Sold Jun 30, 2025

  27 Birch St, Old Saybrook, CT 06475

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Above List Price
  • $386/SF
  • 4 Days On Market

  Current Estimated Value $829,866

  Last Listing Agent Jennifer Pagan RE/MAX One

  27 Birch St, Old Saybrook, CT 06475
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  Est $519,610 Not Listed For Sale

  26 Lookout Hill Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1995

  26 Lookout Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 3% Above List Price
  • $291/SF
  • 20 Days On Market

  • Last Sold Price $505,000
  • Mar 14, 2024

  Last Listing Agent Cheryl Cook RE/MAX
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  $800,000 Sold Aug 20, 2025

  12 4th Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 2,297 Sq Ft
  • Built 1958

  Last Sold Summary

  • 20% Below List Price
  • $348/SF
  • 68 Days On Market

  Current Estimated Value $805,153

  Last Listing Agent Maddy Mattson Coldwell Banker Realty

  12 4th Ave, Old Saybrook, CT 06475
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  Est $1,635,779 Not Listed For Sale

  32 Fenbrook Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 3,886 Sq Ft
  • Built 2015

  32 Fenbrook Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 2% Above List Price
  • $412/SF
  • 21 Days On Market

  • Last Sold Price $1,600,000
  • May 03, 2023

  Last Listing Agent Teri Lewis William Pitt
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  $1,450,000 Sold Dec 05, 2025

  30 Watrous Point Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 5 Baths
  • 4,546 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $319/SF
  • 153 Days On Market

  Current Estimated Value $1,514,182

  Last Listing Agent Nancy Mesham Coldwell Banker Realty

  30 Watrous Point Rd, Old Saybrook, CT 06475
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  Est $716,604 Not Listed For Sale

  65 Springbrook Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,098 Sq Ft
  • Built 1985

  65 Springbrook Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 43% Above List Price
  • $161/SF
  • 86 Days On Market

  • Last Sold Price $500,000
  • Oct 28, 2024

  Last Listing Agent Alan Spotlow William Raveis Real Estate
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  $995,000 Sold Dec 02, 2025

  18 Cottage Place, Old Saybrook, CT 06475

  • 5 Beds
  • 3.5 Baths
  • 3,184 Sq Ft
  • Built 1939

  Last Sold Summary

  • $312/SF
  • 53 Days On Market

  Current Estimated Value $984,529

  Last Listing Agent Tina Rupp William Pitt Sotheby's Int'l

  18 Cottage Place, Old Saybrook, CT 06475
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  Est $1,014,165 Not Listed For Sale

  35 Old Boston Post Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 3,046 Sq Ft
  • Built 1979

  35 Old Boston Post Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 2% Above List Price
  • $328/SF
  • 101 Days On Market

  • Last Sold Price $998,120
  • Feb 28, 2025

  Last Listing Agent Lisa Genovali RE/MAX
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  $1,526,000 Sold Nov 03, 2025

  81 Coulter St Unit 4, Old Saybrook, CT 06475

  • 2 Beds
  • 2.5 Baths
  • 2,524 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Above List Price
  • $605/SF
  • 17 Days On Market

  Last Listing Agent Susan Malton Coldwell Banker Realty

  81 Coulter St Unit 4, Old Saybrook, CT 06475
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  Est $1,037,523 Not Listed For Sale

  3 Shetucket Trail, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 2,688 Sq Ft
  • Built 1957

  3 Shetucket Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 30% Above List Price
  • $298/SF
  • 189 Days On Market

  • Last Sold Price $800,000
  • Jan 25, 2024

  Last Listing Agent Lisa Golebiewski Coldwell Banker Realty
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  $705,000 Sold Dec 02, 2025

  367 Main St Unit 31, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft
  • Built 1980

  Last Sold Summary

  • 18% Above List Price
  • $477/SF
  • 20 Days On Market

  Current Estimated Value $693,135

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

  367 Main St Unit 31, Old Saybrook, CT 06475
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  Not Listed For Sale

  406 Maple Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,489 Sq Ft
  • Built 1940

  406 Maple Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • $1,004/SF
  • 52 Days On Market

  • Last Sold Price $2,500,000
  • Mar 19, 2024

  Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway Home Services
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  $1,625,000 Sold Jul 01, 2025

  9 Overlook Dr, Old Saybrook, CT 06475

  • 4 Beds
  • 4.5 Baths
  • 3,556 Sq Ft
  • Built 2025

  Last Sold Summary

  • 14% Below List Price
  • $457/SF
  • 105 Days On Market

  Current Estimated Value $1,586,069

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  9 Overlook Dr, Old Saybrook, CT 06475
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  Est $688,674 Not Listed For Sale

  478 Main St, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 1,352 Sq Ft
  • Built 1945

  478 Main St, Old Saybrook, CT 06475

  Last Sold Summary

  • 27% Above List Price
  • $401/SF
  • 37 Days On Market

  • Last Sold Price $542,000
  • Jul 07, 2023

  Last Listing Agent Meghan Flood William Raveis Real Estate
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  $569,000 Sold Nov 07, 2025

  4 Sea View Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $527/SF
  • 25 Days On Market

  Current Estimated Value $584,312

  Last Listing Agent Laurie Warshavsky L.J. Shoreline Realty

  4 Sea View Ave, Old Saybrook, CT 06475
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  Est $603,651 Not Listed For Sale

  7 Buck Hill Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft
  • Built 2001

  7 Buck Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 12% Above List Price
  • $305/SF
  • 3 Days On Market

  • Last Sold Price $540,000
  • Jun 16, 2023

  Last Listing Agent Kelly Britt Berkshire Hathaway Home Services
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  $895,000 Sold May 12, 2025

  75 Fenwood Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1964

  Last Sold Summary

  • 15% Above List Price
  • $469/SF
  • 1 Day On Market

  Current Estimated Value $927,213

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

  75 Fenwood Dr, Old Saybrook, CT 06475
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  Est $1,084,056 Not Listed For Sale

  23 Park Ave, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 2,444 Sq Ft
  • Built 1958

  23 Park Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 19% Above List Price
  • $372/SF
  • 5 Days On Market

  • Last Sold Price $910,000
  • Jul 24, 2023

  Last Listing Agent Lauren Iraeta KW Legacy Partners

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