6,196

Old Saybrook, CT Homes

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  • 13 College St, Old Saybrook, CT 06475
    13 College St, Old Saybrook, CT 06475
    13 College St, Old Saybrook, CT 06475
    /3

    $1,490,000

    New Construction $100K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,070 Sq Ft

    13 College St, Old Saybrook, CT 06475

    13 College Street | Old Saybrook, CT TO BE BUILT Discover the opportunity to build your dream home in one of Old Saybrook's most desirable locations-Saybrook Point. Thoughtfully designed with luxury, comfort, and flexibility in mind, this exceptional new construction home offers approximately 2,070 square feet, four bedrooms, two and one-half baths, and the ability to personalize finishes to suit

    Lisa Fekete William Raveis Real Estate

    13 College St, Old Saybrook, CT 06475
  • 23 Clinton Ave, Old Saybrook, CT 06475

    $905,000

    Sold May 08, 2026

    23 Clinton Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $599/SF
    • 50 Days On Market

    Current Estimated Value $911,257

    Last Listing Agent Luke Florian SSG Real Estate LLC

    23 Clinton Ave, Old Saybrook, CT 06475
    • 11 Beechwood Rd, Old Saybrook, CT 06475

      Est $1,345,114

      Not Listed For Sale

      11 Beechwood Rd, Old Saybrook, CT 06475

      • 4 Beds
      • 3 Baths
      • 2,448 Sq Ft
      • Built 1953
      11 Beechwood Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Debbie Huscher Real Broker CT, LLC

  • 84 Ayers Point Rd, Old Saybrook, CT 06475
    84 Ayers Point Rd, Old Saybrook, CT 06475
    84 Ayers Point Rd, Old Saybrook, CT 06475
    /17

    $675,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    84 Ayers Point Rd, Old Saybrook, CT 06475

    Located in the highly sought-after shoreline town of Old Saybrook, this charming Cape offers character, comfort, and exceptional curb appeal. Set on 1.14 beautiful acres in the desirable Otter Cove neighborhood, this well-maintained three-bedroom, two-bath home is ready for its next owners. The updated kitchen features heated tiled floors, while the main level offers a spacious bedroom with a

    Lisa Aranci Berkshire Hathaway NE Prop.

    84 Ayers Point Rd, Old Saybrook, CT 06475
  • 1 Hartford Ave, Old Saybrook, CT 06475

    $620,000

    Sold Sep 30, 2025

    1 Hartford Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 2 Baths
    • 1,762 Sq Ft
    • Built 1940

    Last Sold Summary

    • 11% Below List Price
    • $352/SF
    • 45 Days On Market

    Current Estimated Value $708,496

    Last Listing Agent Bryan Neurath Country Manor Realty

    1 Hartford Ave, Old Saybrook, CT 06475
    • 9 Watrous Point Rd, Old Saybrook, CT 06475

      Est $1,539,777

      Not Listed For Sale

      9 Watrous Point Rd, Old Saybrook, CT 06475

      • 4 Beds
      • 4 Baths
      • 3,952 Sq Ft
      • Built 1997
      9 Watrous Point Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 76 Days On Market

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

  • 17 College St, Old Saybrook, CT 06475
    17 College St, Old Saybrook, CT 06475
    17 College St, Old Saybrook, CT 06475
    /39

    $999,000

    • 3 Beds
    • 3 Baths
    • 1,960 Sq Ft

    17 College St, Old Saybrook, CT 06475

    Discover the perfect blend of comfort, style, and convenience in this beautifully remodeled home. Tucked in a prime location just minutes from fine dining, shopping, the golf course, and the train station, this property offers unparalleled access to everything you need. Walking along the shore to Saybrook Point Inn and Saybrook Lighthouse. Step into the heart of the home: a chef's kitchen with

    Deborah Pach Compass Connecticut, LLC

    17 College St, Old Saybrook, CT 06475
  • 175 Ferry Rd Unit 10, Old Saybrook, CT 06475

    $570,000

    Sold Feb 11, 2026

    175 Ferry Rd Unit 10, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 1,711 Sq Ft
    • Built 2005

    Last Sold Summary

    • $333/SF
    • 26 Days On Market

    Current Estimated Value $609,005

    Last Listing Agent Claire Kilmer Coldwell Banker Realty

    175 Ferry Rd Unit 10, Old Saybrook, CT 06475
    • 1 Dwayne Rd, Old Saybrook, CT 06475

      Est $665,146

      Not Listed For Sale

      1 Dwayne Rd, Old Saybrook, CT 06475

      • 3 Beds
      • 2.5 Baths
      • 2,196 Sq Ft
      • Built 1973
      1 Dwayne Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Sang Jee Eagle Eye Realty PLLC

  • 46 Farview Ave, Old Saybrook, CT 06475
    46 Farview Ave, Old Saybrook, CT 06475
    46 Farview Ave, Old Saybrook, CT 06475
    /35

    $599,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,552 Sq Ft

    46 Farview Ave, Old Saybrook, CT 06475

    Location, location, location. Enjoy shoreline lifestyle in one of Old Saybrook's in demand neighborhoods. Level corner lot. Solid home ready for you to make it your own. Eight total room, three bedrooms, two full baths one updated. Fireplace in the Living room. Sunroom, one car attached garage. Full unfinished basement. Incredible opportunity to create the home of your dreams. Enjoy coastal

    Sheila Burke J.M. REALTY

    46 Farview Ave, Old Saybrook, CT 06475
  • 100 Dudley Ave Unit F31, Old Saybrook, CT 06475

    $735,000

    Sold May 15, 2026

    100 Dudley Ave Unit F31, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 2,310 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Below List Price
    • $318/SF
    • 57 Days On Market

    Current Estimated Value $741,207

    Last Listing Agent Joel Lucas Coldwell Banker Realty

    100 Dudley Ave Unit F31, Old Saybrook, CT 06475
    • 32 Cricket Ct, Old Saybrook, CT 06475

      Est $883,183

      Not Listed For Sale

      32 Cricket Ct, Old Saybrook, CT 06475

      • 4 Beds
      • 2.5 Baths
      • 1,911 Sq Ft
      • Built 1976
      32 Cricket Ct, Old Saybrook, CT 06475

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  • 30 Neptune Dr, Old Saybrook, CT 06475
    30 Neptune Dr, Old Saybrook, CT 06475
    30 Neptune Dr, Old Saybrook, CT 06475
    /39

    $899,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 1,706 Sq Ft

    30 Neptune Dr, Old Saybrook, CT 06475

    Live every day like you're on vacation in sought-after Knollwood Beach! Lovingly enjoyed by the same family for nearly 50 years, this attractive four-bedroom, one-and-a-half-bath home offers a wonderful opportunity to become part of one of Old Saybrook's most desirable beach communities. Inside, the comfortable floor plan features a welcoming living room with built-in bookcases, and a cozy

    Meghan Flood William Raveis Real Estate

    30 Neptune Dr, Old Saybrook, CT 06475
  • 118 Sandy Point Rd, Old Saybrook, CT 06475

    $540,000

    Sold Jun 29, 2026

    118 Sandy Point Rd, Old Saybrook, CT 06475

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

    Last Sold Summary

    • 11% Below List Price
    • $347/SF
    • 469 Days On Market

    Current Estimated Value $546,072

    Last Listing Agent Carla Mousch William Raveis Real Estate

    118 Sandy Point Rd, Old Saybrook, CT 06475
    • 24 Middletown Ave, Old Saybrook, CT 06475

      Est $674,789

      Not Listed For Sale

      24 Middletown Ave, Old Saybrook, CT 06475

      • 3 Beds
      • 1 Bath
      • 1,016 Sq Ft
      • Built 1967
      24 Middletown Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Carla Corrigan eXp Realty

  • 2 Old South Cove Rd, Old Saybrook, CT 06475
    2 Old South Cove Rd, Old Saybrook, CT 06475
    2 Old South Cove Rd, Old Saybrook, CT 06475
    /38

    $1,499,000

    New Construction Pending
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    2 Old South Cove Rd, Old Saybrook, CT 06475

    Welcome to one of Old Saybrook's most compelling brand-new luxury opportunities. Built by one of Connecticut's premier shoreline designers and builders, this exceptional coastal residence showcases a level of craftsmanship, architectural detail, and thoughtful design rarely found in today's market. Summer is in full swing, and with immediate occupancy and flexible closing arrangements available

    Michael Riccio Calcagni Real Estate

    2 Old South Cove Rd, Old Saybrook, CT 06475
  • 43 Indianola Dr, Old Saybrook, CT 06475

    $1,750,000

    Sold Jul 31, 2026

    43 Indianola Dr, Old Saybrook, CT 06475

    • 3 Beds
    • 2.5 Baths
    • 2,978 Sq Ft
    • Built 2012

    Last Sold Summary

    • 3% Above List Price
    • $588/SF
    • 74 Days On Market

    Current Estimated Value $1,696,687

    Last Listing Agent Marc Delise Coldwell Banker Realty

    43 Indianola Dr, Old Saybrook, CT 06475
    • 10 Cliff Dr, Old Saybrook, CT 06475

      Est $564,237

      Not Listed For Sale

      10 Cliff Dr, Old Saybrook, CT 06475

      • 2 Beds
      • 2 Baths
      • 1,555 Sq Ft
      • Built 1992
      10 Cliff Dr, Old Saybrook, CT 06475

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Lewis Jump III RE/MAX One

  • 1324 Boston Post Rd, Old Saybrook, CT 06475
    1324 Boston Post Rd, Old Saybrook, CT 06475
    1324 Boston Post Rd, Old Saybrook, CT 06475
    /20

    $550,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    1324 Boston Post Rd, Old Saybrook, CT 06475

    One floor living in Old Saybrook! This ranch home is a part of the Indian Town Beach association and also conveniently located on Boston Post Road which has beautiful new sidewalks connecting this property to both beaches and shops and restaurants all within walking distance. A picture window gives the living room lovely natural light and a wood burning fireplace for chilly winter nights. An open

    Tina Rupp William Pitt Sotheby's Int'l

    1324 Boston Post Rd, Old Saybrook, CT 06475
  • 8 Owaneco Trail, Old Saybrook, CT 06475

    $1,950,000

    Sold Sep 04, 2026

    8 Owaneco Trail, Old Saybrook, CT 06475

    • 4 Beds
    • 3.5 Baths
    • 2,881 Sq Ft
    • Built 1929

    Last Sold Summary

    • 11% Below List Price
    • $677/SF
    • 37 Days On Market

    Current Estimated Value $2,072,473

    Last Listing Agent Maddy Mattson Coldwell Banker Realty

    8 Owaneco Trail, Old Saybrook, CT 06475
    • 21 Nehantic Trail, Old Saybrook, CT 06475

      Est $741,643

      Not Listed For Sale

      21 Nehantic Trail, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 1,274 Sq Ft
      • Built 1952
      21 Nehantic Trail, Old Saybrook, CT 06475

      Last Sold Summary

      • 26 Days On Market

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

  • 96 Ayers Point Rd, Old Saybrook, CT 06475
    96 Ayers Point Rd, Old Saybrook, CT 06475
    96 Ayers Point Rd, Old Saybrook, CT 06475
    /40

    $1,029,000

    $134K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,109 Sq Ft

    96 Ayers Point Rd, Old Saybrook, CT 06475

    Experience a rare combination of privacy, panoramic marsh and Connecticut River views, and resort-style living at 96 Ayers Point Road in Old Saybrook, with no flood insurance required. This exceptional 4/5-bedroom coastal home features an in-ground gunite pool, expansive wraparound deck, walls of glass, multiple fireplaces, and a flexible floor plan with the option for a main-level or

    Jennifer Gurnell William Raveis Real Estate

    96 Ayers Point Rd, Old Saybrook, CT 06475
  • 7 Ridge Rd, Old Saybrook, CT 06475

    $1,440,000

    Sold Jun 10, 2026

    7 Ridge Rd, Old Saybrook, CT 06475

    • 4 Beds
    • 3.5 Baths
    • 2,413 Sq Ft
    • Built 1926

    Last Sold Summary

    • 4% Below List Price
    • $597/SF
    • 67 Days On Market

    Current Estimated Value $1,458,248

    Last Listing Agent Karen Floriano William Raveis Real Estate

    7 Ridge Rd, Old Saybrook, CT 06475
    • 367 Main St Unit 4, Old Saybrook, CT 06475

      Est $633,607

      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

      • 4 Days On Market

      Last Listing Agent Debbie Lupo Regency Real Estate, LLC

  • 108 Maple Ave, Old Saybrook, CT 06475
    108 Maple Ave, Old Saybrook, CT 06475
    108 Maple Ave, Old Saybrook, CT 06475
    /37

    $1,550,000

    Under Contract
    • 4 Beds
    • 4 Baths
    • 3,188 Sq Ft

    108 Maple Ave, Old Saybrook, CT 06475

    Contemporary coastal elegance meets remarkable privacy along South Cove in Old Saybrook. Set well back from the road on 1.8 acres, this distinctive 3,188-square-foot cedar-sided residence captures sweeping water views from nearly every room. Originally built in 1965 and completely rebuilt in 1991, the home was thoughtfully designed to embrace its spectacular setting, with vaulted ceilings,

    Jessica Blancato William Pitt Sotheby's Int'l

    108 Maple Ave, Old Saybrook, CT 06475
  • 195 Bokum Rd, Old Saybrook, CT 06475

    $350,000

    Sold Feb 24, 2026

    195 Bokum Rd, Old Saybrook, CT 06475

    • 3 Beds
    • 2 Baths
    • 2,340 Sq Ft
    • Built 1799

    Last Sold Summary

    • 12% Below List Price
    • $150/SF
    • 32 Days On Market

    Current Estimated Value $367,918

    Last Listing Agent Dotty Owens Sunset Creek Realty, LLC

    195 Bokum Rd, Old Saybrook, CT 06475
    • 16 Fenbrook Rd, Old Saybrook, CT 06475

      Est $1,873,929

      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

      • 62 Days On Market

      Last Listing Agent Jason Malagutti Dave Jones Realty, LLC

  • 6 Overlook Dr, Old Saybrook, CT 06475
    6 Overlook Dr, Old Saybrook, CT 06475
    6 Overlook Dr, Old Saybrook, CT 06475
    /24

    $935,000

    Coming Soon Pre-Foreclosure
    • 4 Beds
    • 3.5 Baths
    • 2,816 Sq Ft

    6 Overlook Dr, Old Saybrook, CT 06475

    Step into this beautiful and charming farmhouse, where timeless character meets a bright, open and inviting floor plan. A welcoming grand foyer sets the tone, leading into sun-filled living spaces accented by hardwood floors, skylights and abundant windows throughout. The stunning wraparound deck is a true focal point of the home, offering the perfect setting for entertaining, relaxing or simply

    Sharon Linder Berkshire Hathaway NE Prop.

    6 Overlook Dr, Old Saybrook, CT 06475
  • 9 2nd Ave, Old Saybrook, CT 06475

    $500,000

    Sold May 08, 2026

    9 2nd Ave, Old Saybrook, CT 06475

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1959

    Last Sold Summary

    • 9% Above List Price
    • $481/SF
    • 2 Days On Market

    Current Estimated Value $490,059

    Last Listing Agent Sally Tucker Coldwell Banker Realty

    9 2nd Ave, Old Saybrook, CT 06475
    • 64 Obed Heights, Old Saybrook, CT 06475

      Est $578,013

      Not Listed For Sale

      64 Obed Heights, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 1,636 Sq Ft
      • Built 1958
      64 Obed Heights, Old Saybrook, CT 06475

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Joshua Young Berkshire Hathaway NE Prop.

  • 12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    /38

    $5,900,000

    • 4 Beds
    • 4 Baths
    • 5,651 Sq Ft

    12 Rocky Point Rd, Old Saybrook, CT 06475

    Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy

    Sharon Linder Berkshire Hathaway NE Prop.

    12 Rocky Point Rd, Old Saybrook, CT 06475
  • 175 Ferry Rd Unit 4, Old Saybrook, CT 06475

    $585,000

    Sold Mar 13, 2026

    175 Ferry Rd Unit 4, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 1,852 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $316/SF
    • 16 Days On Market

    Current Estimated Value $603,122

    Last Listing Agent Gigi Giordano Taylor Compass Connecticut, LLC

    175 Ferry Rd Unit 4, Old Saybrook, CT 06475
    • 5 Watch Hill Rd, Old Saybrook, CT 06475

      Est $870,320

      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

      • 151 Days On Market

      Last Listing Agent Kevin Geysen William Pitt Sotheby's Int'l

  • 101-A Sequassen Ave, Old Saybrook, CT 06475
    101-A Sequassen Ave, Old Saybrook, CT 06475
    101-A Sequassen Ave, Old Saybrook, CT 06475
    /9

    $1,750,000

    • Land
    • 20,037 Sq Ft
    • $3,804,348 per Acre

    101-A Sequassen Ave, Old Saybrook, CT 06475

    APPROVED OCEANFRONT LOT - WALK TO THE BEACH FROM YOUR BACKYARD Design the life you've always envisioned. Whether you dream of a timeless shingle-style coastal retreat or a striking modern waterfront masterpiece, this exceptional homesite offers the perfect canvas to bring your vision to life. This fully approved, level building lot is ready for construction, allowing you to move forward with

    Fationa Meco Houlihan Lawrence WD

    101-A Sequassen Ave, Old Saybrook, CT 06475
  • 55 Cypress Rd, Old Saybrook, CT 06475

    $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 $1,018,054

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

    55 Cypress Rd, Old Saybrook, CT 06475
    • 15 Crest Rd, Old Saybrook, CT 06475

      Est $1,345,153

      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

      • 28 Days On Market

      Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  • 5 Sand Creek Dr, Old Saybrook, CT 06475
    5 Sand Creek Dr, Old Saybrook, CT 06475
    5 Sand Creek Dr, Old Saybrook, CT 06475
    /40

    $1,249,000

    • 4 Beds
    • 3 Baths
    • 3,684 Sq Ft

    5 Sand Creek Dr, Old Saybrook, CT 06475

    Welcome to 5 Sand Creek Drive, a truly unique coastal contemporary in Old Saybrook, beautifully positioned to capture stunning marsh and water views. Filled with natural light and designed around its exceptional setting, this distinctive home offers an open floor plan, brand-new windows throughout, and wonderful spaces for both everyday living and entertaining. The dramatic living room is a

    Gigi Giordano Taylor Compass Connecticut, LLC

    5 Sand Creek Dr, Old Saybrook, CT 06475
  • 66 Pennywise Ln, Old Saybrook, CT 06475

    $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 $1,516,613

    Last Listing Agent Joel Lucas Coldwell Banker Realty

    66 Pennywise Ln, Old Saybrook, CT 06475
    • 16 James Ct, Old Saybrook, CT 06475

      Est $1,183,405

      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

      • 20 Days On Market

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

  • 5 Tudor Ct E, Old Saybrook, CT 06475
    5 Tudor Ct E, Old Saybrook, CT 06475
    5 Tudor Ct E, Old Saybrook, CT 06475
    /40

    $795,000

    • 3 Beds
    • 1 Bath
    • 2,002 Sq Ft

    5 Tudor Ct E, Old Saybrook, CT 06475

    Spectacular South Cove views, deeded beach rights and remarkably low taxes make this nicely updated shoreline home an exceptional opportunity! Set on a beautiful half-acre lot, this spacious split-level offers 3-4 bedrooms, a versatile floor plan and wonderful water views that bring the coastal setting right into your everyday life. Inside you'll find hardwood floors, double oven, a fireplace for

    Joel Lucas Coldwell Banker Realty

    5 Tudor Ct E, Old Saybrook, CT 06475

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