6,229

Old Saybrook, CT Homes

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  • 9 Barley Hill Rd, Old Saybrook, CT 06475
    9 Barley Hill Rd, Old Saybrook, CT 06475
    9 Barley Hill Rd, Old Saybrook, CT 06475
    /39

    $850,000

    $49K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,544 Sq Ft

    9 Barley Hill Rd, Old Saybrook, CT 06475

    This beautifully maintained home offers the perfect blend of luxury and comfort! The main level offers exceptional versatility with an open floor plan, hardwood floors, a luxurious primary bedroom suite, along with a living room, family room, gourmet kitchen and formal dining room designed for both relaxed living and elegant gatherings. The first floor primary bedroom suite features California

    Sharon Linder Berkshire Hathaway NE Prop.

    9 Barley Hill Rd, Old Saybrook, CT 06475
  • 41 Briarwood Dr, Old Saybrook, CT 06475

    $720,000

    Sold Mar 03, 2026

    41 Briarwood Dr, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 1,076 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $669/SF
    • 47 Days On Market

    Current Estimated Value $723,720

    Last Listing Agent Rick Allen William Raveis Real Estate

    41 Briarwood Dr, Old Saybrook, CT 06475
    • 4 Willow Brook Farm Rd, Old Saybrook, CT 06475

      Est $1,018,588

      Not Listed For Sale

      4 Willow Brook Farm Rd, Old Saybrook, CT 06475

      • 4 Beds
      • 3.5 Baths
      • 4,132 Sq Ft
      • Built 1998
      4 Willow Brook Farm Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Jan Murray J.M. REALTY

  • 14 Cedarwood Ln, Old Saybrook, CT 06475
    14 Cedarwood Ln, Old Saybrook, CT 06475
    14 Cedarwood Ln, Old Saybrook, CT 06475
    /28

    $595,000

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,033 Sq Ft

    14 Cedarwood Ln, Old Saybrook, CT 06475

    BACK ON MARKET - BUYER GOT COLD FEET! Welcome to your new shoreline home - a ranch-style retreat in the heart of Old Saybrook. This beautifully maintained 3-bedroom, 1 1/2-bathroom home offers a perfect blend of comfortable living and coastal New England lifestyle - all just approx. 1 mile from the private Cornfield Point beach with deeded beach rights. Inside you'll discover a bright,

    Chelsea Daley Haven Compass Realty LLC

    14 Cedarwood Ln, Old Saybrook, CT 06475
  • 515 Maple Ave, Old Saybrook, CT 06475

    $2,125,000

    Sold Oct 10, 2025

    515 Maple Ave, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1954

    Last Sold Summary

    • 6% Above List Price
    • $1,557/SF
    • 38 Days On Market

    Current Estimated Value $2,313,914

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

    515 Maple Ave, Old Saybrook, CT 06475
    • 64 Atlantic Dr, Old Saybrook, CT 06475

      Est $723,154

      Not Listed For Sale

      64 Atlantic Dr, Old Saybrook, CT 06475

      • 3 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1960
      64 Atlantic Dr, Old Saybrook, CT 06475

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Joel Lucas Coldwell Banker Realty

  • 1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    /6

    $695,000

    $300K PRICE DROP
    • 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.

    Maxwell Lyman Lyman Real Estate

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

    $887,000

    Sold Nov 24, 2025

    3 Jorgensen Ln, Old Saybrook, CT 06475

    • 4 Beds
    • 2.5 Baths
    • 2,784 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $319/SF
    • 26 Days On Market

    Current Estimated Value $934,548

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    3 Jorgensen Ln, Old Saybrook, CT 06475
    • 7 Beaver Dam Trail, Old Saybrook, CT 06475

      Est $713,081

      Not Listed For Sale

      7 Beaver Dam Trail, Old Saybrook, CT 06475

      • 3 Beds
      • 2.5 Baths
      • 1,870 Sq Ft
      • Built 1980
      7 Beaver Dam Trail, Old Saybrook, CT 06475

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Joel Lucas Coldwell Banker Realty

  • 25 Sunset Rd Unit 3, Old Saybrook, CT 06475
    25 Sunset Rd Unit 3, Old Saybrook, CT 06475
    25 Sunset Rd Unit 3, Old Saybrook, CT 06475
    /39

    $660,000

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

    25 Sunset Rd Unit 3, Old Saybrook, CT 06475

    Looking for a home that feels like vacation every day? Carefree coastal living can be yours at this stylish townhouse at the Oyster River Landing condos. With just 20 homes, residents enjoy beautiful grounds, sunsets, and a pool overlooking the private boat basin on the Oyster River. This leads out to Long Island Sound and is excellent for fishing, kayaking, and paddle boarding. As you enter the

    Rose McWaid William Raveis Real Estate

    25 Sunset Rd Unit 3, Old Saybrook, CT 06475
  • 12 Hill Rd, Old Saybrook, CT 06475

    $991,000

    Sold Jul 15, 2026

    12 Hill Rd, Old Saybrook, CT 06475

    • 3 Beds
    • 3 Baths
    • 3,496 Sq Ft
    • Built 1996

    Last Sold Summary

    • 8% Below List Price
    • $283/SF
    • 104 Days On Market

    Current Estimated Value $1,081,533

    Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

    12 Hill Rd, Old Saybrook, CT 06475
    • 95 Chalker Beach Rd, Old Saybrook, CT 06475

      Est $602,241

      Not Listed For Sale

      95 Chalker Beach Rd, Old Saybrook, CT 06475

      • 3 Beds
      • 1 Bath
      • 950 Sq Ft
      • Built 1952
      95 Chalker Beach Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 35 Days On Market

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

  • 18 Old South Cove Rd, Old Saybrook, CT 06475
    18 Old South Cove Rd, Old Saybrook, CT 06475
    18 Old South Cove Rd, Old Saybrook, CT 06475
    /40

    $899,000

    $76K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,569 Sq Ft

    18 Old South Cove Rd, Old Saybrook, CT 06475

    Whether your vision is to Move-in, Renovate, or Custom Build from the ground up, this water-view coastal property is for you! Currently home to a classic 1,569 sq. ft. coastal ranch built on an oversized .42-acre water-view parcel, the true value of this premier Residential District A property lies in its exceptional dimensions, rare zoning advantages, and all the possibilities that come with the

    Steven Koleno Beycome of Connecticut

    18 Old South Cove Rd, Old Saybrook, CT 06475
  • 350 Middlesex Turnpike, Old Saybrook, CT 06475

    $725,000

    Sold Aug 12, 2025

    350 Middlesex Turnpike, Old Saybrook, CT 06475

    • Land
    • 1.38 Acres
    • $525,362 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 468 Days On Market

    Current Estimated Value $757,552

    Last Listing Agent Michael Hvizdo Coldwell Banker Realty

    350 Middlesex Turnpike, Old Saybrook, CT 06475
    • 11 Shepard St, Old Saybrook, CT 06475

      Est $942,647

      Not Listed For Sale

      11 Shepard St, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 2,400 Sq Ft
      • Built 1865
      11 Shepard St, Old Saybrook, CT 06475

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Rick Allen William Raveis Real Estate

  • 81 Hartford Ave, Old Saybrook, CT 06475
    81 Hartford Ave, Old Saybrook, CT 06475
    81 Hartford Ave, Old Saybrook, CT 06475
    /40

    $2,150,000

    $145K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,440 Sq Ft

    81 Hartford Ave, Old Saybrook, CT 06475

    Experience the pinnacle of Connecticut shoreline living in this exquisitely remodeled coastal retreat, ideally located just three homes from the private association beach in the Saybrook Manor Beach community. Blending timeless coastal elegance with today's most desirable amenities, this exceptional four-bedroom, two-bath home provides the perfect balance of luxury, comfort, and effortless

    Gigi Giordano Taylor Compass Connecticut, LLC

    81 Hartford Ave, Old Saybrook, CT 06475
  • 20 Hill St, Old Saybrook, CT 06475

    $700,000

    Sold Jan 07, 2026

    20 Hill St, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1930

    Last Sold Summary

    • 12% Below List Price
    • $489/SF
    • 132 Days On Market

    Current Estimated Value $714,782

    Last Listing Agent Pardi & Zucco Team William Pitt Sotheby's Int'l

    20 Hill St, Old Saybrook, CT 06475
    • 41 Dudley Ave, Old Saybrook, CT 06475

      Est $656,664

      Not Listed For Sale

      41 Dudley Ave, Old Saybrook, CT 06475

      • 3 Beds
      • 1.5 Baths
      • 1,621 Sq Ft
      • Built 1940
      41 Dudley Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

  • 5 Cove Landing, Old Saybrook, CT 06475
    5 Cove Landing, Old Saybrook, CT 06475
    5 Cove Landing, Old Saybrook, CT 06475
    /40

    $1,649,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,787 Sq Ft

    5 Cove Landing, Old Saybrook, CT 06475

    Nestled within an enclave of distinguished homes in the heart of Old Saybrook, this exceptional residence captures sweeping water views and breathtaking morning sunrises, offering a rare blend of sophistication, and timeless coastal charm. From the moment you enter this light filled home, exceptional craftsmanship and design are evident. Custom millwork defines each space, while rich wood

    Terry Kemper Coldwell Banker Realty

    5 Cove Landing, Old Saybrook, CT 06475
  • 21 Fenwick St, Old Saybrook, CT 06475

    $799,000

    Sold Mar 27, 2026

    21 Fenwick St, Old Saybrook, CT 06475

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1938

    Last Sold Summary

    • $558/SF
    • 120 Days On Market

    Current Estimated Value $805,971

    Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

    21 Fenwick St, Old Saybrook, CT 06475
    • 5 Barley Hill Rd, Old Saybrook, CT 06475

      Est $942,518

      Not Listed For Sale

      5 Barley Hill Rd, Old Saybrook, CT 06475

      • 4 Beds
      • 5 Baths
      • 3,048 Sq Ft
      • Built 1995
      5 Barley Hill Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Rick Allen William Raveis Real Estate

  • 28 Bellaire Dr, Old Saybrook, CT 06475
    28 Bellaire Dr, Old Saybrook, CT 06475
    28 Bellaire Dr, Old Saybrook, CT 06475
    /40

    $850,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,175 Sq Ft

    28 Bellaire Dr, Old Saybrook, CT 06475

    Welcome to the highly sought-after Cornfield Point Beach Association, where coastal charm meets effortless year-round living. This beautifully maintained cottage-style ranch offers the perfect seaside retreat for those seeking an upscale second home or an easy-to-maintain retirement residence in one of Old Saybrook's most desirable beach communities. The newer white kitchen opens to inviting

    Joel Lucas Coldwell Banker Realty

    28 Bellaire Dr, Old Saybrook, CT 06475
  • 129 Old Boston Post Rd, Old Saybrook, CT 06475

    $900,000

    Sold Jun 30, 2026

    129 Old Boston Post Rd, Old Saybrook, CT 06475

    • 3 Beds
    • 2.5 Baths
    • 2,170 Sq Ft
    • Built 1900

    Last Sold Summary

    • $415/SF
    • 80 Days On Market

    Current Estimated Value $882,252

    Last Listing Agent Joel Lucas Coldwell Banker Realty

    129 Old Boston Post Rd, Old Saybrook, CT 06475
    • 32 Willard Ave, Old Saybrook, CT 06475

      Est $1,604,929

      Not Listed For Sale

      32 Willard Ave, Old Saybrook, CT 06475

      • 5 Beds
      • 3.5 Baths
      • 3,502 Sq Ft
      • Built 1961
      32 Willard Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Nancy Mesham Coldwell Banker Realty

  • 6 Watch Hill Rd, Old Saybrook, CT 06475
    6 Watch Hill Rd, Old Saybrook, CT 06475
    6 Watch Hill Rd, Old Saybrook, CT 06475
    /15

    $460,000

    $91K PRICE DROP Under Contract
    • 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
  • 450 Maple Ave, Old Saybrook, CT 06475

    $3,200,000

    Sold Sep 10, 2025

    450 Maple Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 5 Baths
    • 4,435 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $722/SF
    • 20 Days On Market

    Current Estimated Value $3,420,547

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

    450 Maple Ave, Old Saybrook, CT 06475
    • 10 Vista Terrace, Old Saybrook, CT 06475

      Est $570,205

      Not Listed For Sale

      10 Vista Terrace, Old Saybrook, CT 06475

      • 3 Beds
      • 2.5 Baths
      • 2,143 Sq Ft
      • Built 1955
      10 Vista Terrace, Old Saybrook, CT 06475

      Last Sold Summary

      • 70 Days On Market

      Last Listing Agent Sandra Ciarleglio William Raveis Real Estate

  • 33 Fenwood Rd, Old Saybrook, CT 06475

    $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 $832,257

    Last Listing Agent Joel Lucas Coldwell Banker Realty

    33 Fenwood Rd, Old Saybrook, CT 06475
    • 6 Parkman Place, Old Saybrook, CT 06475

      Est $1,412,957

      Not Listed For Sale

      6 Parkman Place, Old Saybrook, CT 06475

      • 4 Beds
      • 2.5 Baths
      • 3,301 Sq Ft
      • Built 2002
      6 Parkman Place, Old Saybrook, CT 06475

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Joel Lucas Coldwell Banker Realty

  • 446 Main St Unit 9, Old Saybrook, CT 06475

    $1,420,000

    Sold Jun 17, 2026

    446 Main St Unit 9, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 2,294 Sq Ft
    • Built 2004

    Last Sold Summary

    • 9% Above List Price
    • $619/SF
    • 30 Days On Market

    Current Estimated Value $1,294,225

    Last Listing Agent Maureen OGrady Compass Connecticut, LLC

    446 Main St Unit 9, Old Saybrook, CT 06475
    • 1 Boulder Dr, Old Saybrook, CT 06475

      Est $1,021,163

      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

      • 6 Days On Market

      Last Listing Agent Suzanne McConville William Raveis Real Estate

  • 3 4th Ave, Old Saybrook, CT 06475

    $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 $350,463

    Last Listing Agent Phil Ledwith Century 21 AllPoints Realty

    3 4th Ave, Old Saybrook, CT 06475
    • 4 Patterson Place, Old Saybrook, CT 06475

      Est $648,658

      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

      • 60 Days On Market

      Last Listing Agent Lynn Lehrman Re/Max Valley Shore

  • 30 Sunset Ave, Old Saybrook, CT 06475

    $395,000

    Sold Jul 17, 2026

    30 Sunset Ave, Old Saybrook, CT 06475

    • 4 Beds
    • 1 Bath
    • 1,670 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $237/SF
    • 8 Days On Market

    Current Estimated Value $408,679

    Last Listing Agent Sheila Hilton Coldwell Banker Realty

    30 Sunset Ave, Old Saybrook, CT 06475
    • 216 School House Rd, Old Saybrook, CT 06475

      Est $714,915

      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

      • 0 Days On Market

      Last Listing Agent Joel Lucas Coldwell Banker Realty

  • 46 Maple Ave, Old Saybrook, CT 06475

    $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 $560,222

    Last Listing Agent Fran Manganello Coldwell Banker Realty

    46 Maple Ave, Old Saybrook, CT 06475
    • 33 Old Boston Post Rd, Old Saybrook, CT 06475

      Est $1,335,511

      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

      • 28 Days On Market

      Last Listing Agent Brieanne Vinyard Berkshire Hathaway NE Prop.

  • 78 Hartford Ave, Old Saybrook, CT 06475

    $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 $775,453

    Last Listing Agent Robert Perriello Century 21 AllPoints Realty

    78 Hartford Ave, Old Saybrook, CT 06475
    • 502 Main St, Old Saybrook, CT 06475

      Est $2,225,975

      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

      • 46 Days On Market

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

  • 25 Sunset Rd Unit 7, Old Saybrook, CT 06475

    $750,000

    Sold May 28, 2026

    25 Sunset Rd Unit 7, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 2,090 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $359/SF
    • 62 Days On Market

    Last Listing Agent Scott Nardozzi Cavanaugh & Company LLC

    25 Sunset Rd Unit 7, Old Saybrook, CT 06475

Showing Results 201 - 240, Page 6 of 18

Connecticut Middlesex County

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