1,162

Saybrook Manor, CT Homes

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  • /38

    $800,000

    • 2 Beds
    • 1 Bath
    • 1,478 Sq Ft

    25 River Ave, Old Saybrook, CT 06475

    Welcome to the heart of Saybrook Manor! This beautifully maintained ranch-style home offers the perfect blend of shoreline charm and everyday convenience. Situated on a desirable corner lot, this one-level home features comfortable living spaces, thoughtful updates, and a relaxed coastal lifestyle. Enjoy easy access to the private Saybrook Manor beaches, Oyster River, nearby marinas, restaurants,

    Agent Photo

    Linda O'Hara

    William Raveis Real Estate

    25 River Ave, Old Saybrook, CT 06475
  • /20

    $4,500 Plus Fees

    • 3 Beds
    • 2 Baths
    • 1,358 Sq Ft
    • House for Rent

    28 Beach Rd E, Old Saybrook, CT 06475

    Amazing views every day at 28 Beach Rd West, Old Saybrook! This beautiful Academic Rental beach home has 3 bedrooms and 2 baths and is available for your enjoyment ... across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

    28 Beach Rd E, Old Saybrook, CT 06475
  • 143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475

    $550,000

    Sold Nov 19, 2025

    143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475

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

    Last Sold Summary

    • 11% Below List Price
    • $353/SF
    • 133 Days On Market

    Current Estimated Value $590,541

    Last Listing Agent Lorenda DiMeo Century 21 AllPoints Realty

    143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475
    • 23 Red Bird Trail, Old Saybrook, CT 06475

      Est $1,716,112

      Not Listed For Sale

      23 Red Bird Trail, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 2,580 Sq Ft
      • Built 1955
      23 Red Bird Trail, Old Saybrook, CT 06475

      Last Sold Summary

      • 158 Days On Market

      Last Listing Agent Jay Cusack Better Homes and Gardens Real Estate Executive Real Estate

  • /40

    $649,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    8 Kenn Rd, Old Saybrook, CT 06475

    Coastal living is calling! This is a fully furnished shoreline retreat set within the sought-after Chalker Beach Association. Offered As-Is and thoughtfully updated, this inviting home is ideal as a year-round residence, weekend escape, or classic summer getaway. With marsh views, salt air, and a relaxed beach-community setting, this is a turnkey opportunity designed for immediate enjoyment

    Agent Photo

    Michael Marsden

    Compass Connecticut, LLC

    8 Kenn Rd, Old Saybrook, CT 06475
  • /6

    $2,650 Plus Fees

    • 2 Beds
    • 1 Bath
    • 904 Sq Ft
    • House for Rent

    31 River Ave, Old Saybrook, CT 06475

    Welcome to your new home in the charming Saybrook Manor district of Old Saybrook, Connecticut! This inviting Academic rental property offers a perfect blend of comfort and convenience, making it an ideal choice for those seeking a vibrant community atmosphere. Key property features include spacious bedrooms and well-appointed bathrooms, offering ample space for relaxation and daily living.

    31 River Ave, Old Saybrook, CT 06475
  • 254 Hidden Cove Rd, Old Saybrook, CT 06475

    $570,000

    Sold Feb 02, 2026

    254 Hidden Cove Rd, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 1,557 Sq Ft
    • Built 1977

    Last Sold Summary

    • 1% Below List Price
    • $366/SF
    • 117 Days On Market

    Current Estimated Value $589,269

    Last Listing Agent Bob Yostos Coldwell Banker Realty

    254 Hidden Cove Rd, Old Saybrook, CT 06475
    • 10 Allendale Rd, Old Saybrook, CT 06475

      Est $737,497

      Not Listed For Sale

      10 Allendale Rd, Old Saybrook, CT 06475

      • 3 Beds
      • 2.5 Baths
      • 1,924 Sq Ft
      • Built 1969
      10 Allendale Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 91 Days On Market

      Last Listing Agent Dana Gibson William Raveis Real Estate

  • /40

    $2,899,900

    • 5 Beds
    • 4.5 Baths
    • 5,062 Sq Ft

    2 Captains Ln, Old Saybrook, CT 06475

    Join us for our latest 'Sunset Roll Out' Party / Saturday 6.20.26 / 4-7 pm. Great Music, Light Fare & Drink. It is always a great time! Dynamic 5000 Sq/Ft Contemporary Colonial w/ a Fabulous 700 Sq/Ft In-Law Apartment (seperate entrance) built in 2021 in the coveted Indian Town Beach Association! Check out those Pics! 5 Brs , 4.5 Bths, Soaring Ceilings w/ Open Balconies, Two Story Linear

    Bill Heenan William Raveis Real Estate

    2 Captains Ln, Old Saybrook, CT 06475
  • /34

    $2,600 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft
    • House for Rent

    4 Elinor Rd, Old Saybrook, CT 06475

    CHALKER BEACH ACADEMIC RENTAL AVAILABLE 9/15/26 - 5/15/26. Adorable fully furnished 3 bedroom, 1.1 bathroom Cape featuring kitchen open to dining room, living room, 1 bedroom on the main level, 2 bedrooms on the 2nd floor, 3 season screened in porch, outdoor shower, off street parking for 4 cars. Tenants will be responsible for water, electric (lights, hot water, AC & Heat) and snow removal. The

    Gera Delavega KW Legacy Partners

    4 Elinor Rd, Old Saybrook, CT 06475
  • 95 Middletown Ave, Old Saybrook, CT 06475

    $1,049,900

    Sold Jul 30, 2026

    95 Middletown Ave, Old Saybrook, CT 06475

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1926

    Last Sold Summary

    • 5% Below List Price
    • $670/SF
    • 70 Days On Market

    Current Estimated Value $1,016,587

    Last Listing Agent Tracy Molloy Coldwell Banker Realty

    95 Middletown Ave, Old Saybrook, CT 06475
    • 28 Attawanhood Trail, Old Saybrook, CT 06475

      Est $736,217

      Not Listed For Sale

      28 Attawanhood Trail, Old Saybrook, CT 06475

      • 3 Beds
      • 1 Bath
      • 1,172 Sq Ft
      • Built 1953
      28 Attawanhood Trail, Old Saybrook, CT 06475

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Craig Hebert RE/MAX Right Choice

  • /38

    $999,000

    $201K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    170 Old Post Rd, Old Saybrook, CT 06475

    Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. The Bushnell-Dickinson House is a Georgian colonial that retains its original features inside and out. including original wide-board pine flooring, paneled walls, four fireplaces, two staircases, dentil moldings, authentic hardware and classic

    Rose McWaid William Raveis Real Estate

    170 Old Post Rd, Old Saybrook, CT 06475
  • /18

    $2,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • House for Rent

    9 Red Bird Trail, Old Saybrook, CT 06475

    ACADEMIC RENTAL until mid May 2027. Three BR Colonial with Sun Room located in the beautiful Indian Town Beach Association. Views of LIS and harbor. Bright and spacious rooms. This location is perfect for walking, biking or strolling along the beach. Conveniently located to I95, Train Station, Shopping and The Kate. Sorry NO pets or smoking allowed.

    Sandy Orsie Berkshire Hathaway NE Prop.

    9 Red Bird Trail, Old Saybrook, CT 06475
  • 3 Deerfield Rd, Old Saybrook, CT 06475

    $715,000

    Sold May 29, 2026

    3 Deerfield Rd, Old Saybrook, CT 06475

    • 4 Beds
    • 2.5 Baths
    • 1,916 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Above List Price
    • $373/SF
    • 1 Day On Market

    Current Estimated Value $721,401

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

    3 Deerfield Rd, Old Saybrook, CT 06475
    • 15 Cranton Ave, Old Saybrook, CT 06475

      Est $467,910

      Not Listed For Sale

      15 Cranton Ave, Old Saybrook, CT 06475

      • 1 Bed
      • 1 Bath
      • 612 Sq Ft
      • Built 1938
      15 Cranton Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Matt Diamond Houlihan Lawrence WD

  • /33

    $750,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft

    25 Uncas Trail, Old Saybrook, CT 06475

    Welcome to the desirable Indiantown Beach community, where endless possibilities await. This well-loved home offers a spacious floor plan featuring a bright sunroom, generous family room with a floor-to-ceiling gas fireplace and built-ins, and a large primary suite with its full bath and own private deck. Ready for cosmetic updates, this home presents an excellent opportunity to create your dream

    Sharon Linder Berkshire Hathaway NE Prop.

    25 Uncas Trail, Old Saybrook, CT 06475
  • /36

    $18,000 Per Month

    • 4 Beds
    • 3 Baths
    • 1,360 Sq Ft
    • House for Rent

    8 Belaire Manor, Old Saybrook, CT 06475

    Summer 2027 -- Available: June, July, August, September. This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the

    Erika Raffles William Pitt Sotheby's Int'l

    8 Belaire Manor, Old Saybrook, CT 06475
  • 14 Denmore Ln, Old Saybrook, CT 06475

    $460,000

    Sold Jun 16, 2026

    14 Denmore Ln, Old Saybrook, CT 06475

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft
    • Built 1950

    Last Sold Summary

    • 9% Below List Price
    • $385/SF
    • 25 Days On Market

    Current Estimated Value $473,442

    Last Listing Agent Terence Dominick Exceptional Real Estate LLC

    14 Denmore Ln, Old Saybrook, CT 06475
    • 6 Tucker Rd, Old Saybrook, CT 06475

      Est $666,771

      Not Listed For Sale

      6 Tucker Rd, Old Saybrook, CT 06475

      • 2 Beds
      • 1.5 Baths
      • 780 Sq Ft
      • Built 1954
      6 Tucker Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Terry McDonald McDonald Real Estate, LLC

  • /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
  • /22

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,358 Sq Ft
    • House for Rent

    28 Beach Rd W, Old Saybrook, CT 06475

    Amazing views of Long Island Sound at 28 Beach Rd West, Old Saybrook! Beautiful Academic Rental "beach" home, with 3 bedrooms and 2 baths, available for your enjoyment, across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

    Terry McDonald McDonald Real Estate, LLC

    28 Beach Rd W, Old Saybrook, CT 06475
  • 39 Middletown Ave, Old Saybrook, CT 06475

    $385,000

    Sold Jul 15, 2026

    39 Middletown Ave, Old Saybrook, CT 06475

    • 4 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1908

    Last Sold Summary

    • 14% Below List Price
    • $602/SF
    • 130 Days On Market

    Current Estimated Value $408,583

    Last Listing Agent Tracy Pentalow Property Shoppe, LLC

    39 Middletown Ave, Old Saybrook, CT 06475
    • 235 Hidden Cove Rd, Old Saybrook, CT 06475

      Est $561,377

      Not Listed For Sale

      235 Hidden Cove Rd, Old Saybrook, CT 06475

      • 2 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1978
      235 Hidden Cove Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 0 Days On Market

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

  • /30

    $510,000

    $19K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,557 Sq Ft

    256 Hidden Cove Rd, Old Saybrook, CT 06475

    Discover effortless shoreline living at Summerwood in Old Saybrook. This beautifully maintained 2-bedroom, 1.5-bath condominium offers 1,557 SqFt of light-filled living space with tranquil marsh views and an upper-level loft perfect for a home office, guest space, or reading retreat. The updated kitchen features granite countertops, stainless steel appliances, and a center island, while hardwood

    Carla Mousch William Raveis Real Estate

    256 Hidden Cove Rd, Old Saybrook, CT 06475
  • /14

    $2,450 Per Month

    • 3 Beds
    • 2 Baths
    • 1,139 Sq Ft
    • House for Rent

    54 Hartford Ave, Old Saybrook, CT 06475

    Live at the beach from October 1, 2026 - April 30, 2027. Spacious ranch with an open layout. The primary bedroom has access to the backyard and is next to the full bathroom which has a walk in shower and washer/dryer. On the other side of the home you will find 2 generous sized bedrooms and a full bathroom with bath/tub combo. Central air. Outdoor shower. Private backyard with patio and grill.

    Kate Lombardi Coccomo Real Estate LLC

    54 Hartford Ave, Old Saybrook, CT 06475
  • 129 Nehantic Trail, Old Saybrook, CT 06475

    $850,000

    Sold May 26, 2026

    129 Nehantic Trail, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 944 Sq Ft
    • Built 1971

    Last Sold Summary

    • 6% Above List Price
    • $900/SF
    • 9 Days On Market

    Current Estimated Value $846,243

    Last Listing Agent Lynn Toper CR Premier Properties

    129 Nehantic Trail, Old Saybrook, CT 06475
    • 20 Whitney Ave, Old Saybrook, CT 06475

      Est $624,074

      Not Listed For Sale

      20 Whitney Ave, Old Saybrook, CT 06475

      • 1 Bed
      • 1 Bath
      • 1,107 Sq Ft
      • Built 1946
      20 Whitney Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Joanne Breen ERA Hart Sargis-Breen

  • /32

    $699,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,120 Sq Ft

    52 Chalker Beach Rd, Old Saybrook, CT 06475

    No stone was left unturned at this turn key beach house in the Chalker Beach Association! Completely and professionally renovated from bottom to top, this 3 bedroom cottage is open, light and airy and ready for you to move in, just in time for summer! A spacious living room opens into the lovely eat-in kitchen with custom cabinets, stainless steel appliances and beautiful crown moulding. A bright

    Tina Rupp William Pitt Sotheby's Int'l

    52 Chalker Beach 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
    • 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

  • /33

    $649,900

    • 3 Beds
    • 1 Bath
    • 968 Sq Ft

    96 Chalker Beach Rd, Old Saybrook, CT 06475

    Welcome to your seasonal sanctuary at Chalker Beach, where sun-soaked days and starry nights create lasting memories. Offered fully furnished and thoughtfully styled with relaxed coastal charm, this seasonal cottage is the perfect place to slow down, unwind, and enjoy easy shoreline living. Just a short walk or golf cart ride to the beach, the home is tucked into one of the shoreline's most loved

    Danielle Spada Coldwell Banker Realty

    96 Chalker Beach Rd, 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
    • 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

  • /40

    $1,995,000

    $300K 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
  • 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 Middletown Ave, Old Saybrook, CT 06475

      Est $656,399

      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

      • 302 Days On Market

      Last Listing Agent Steven Koleno Beycome of Connecticut

  • 122 Old Post Rd, Old Saybrook, CT 06475

    $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 $997,794

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

    122 Old Post Rd, Old Saybrook, CT 06475
    • 45 Middletown Ave, Old Saybrook, CT 06475

      Est $637,542

      Not Listed For Sale

      45 Middletown Ave, Old Saybrook, CT 06475

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1929
      45 Middletown Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jason Saphire www.HomeZu.com

  • 21 Baum Ave, Old Saybrook, CT 06475

    $600,000

    Sold Aug 24, 2026

    21 Baum Ave, Old Saybrook, CT 06475

    • 2 Beds
    • 1.5 Baths
    • 1,290 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Above List Price
    • $465/SF
    • 4 Days On Market

    Current Estimated Value $585,561

    Last Listing Agent Courtney Cusano Coldwell Banker Realty

    21 Baum Ave, Old Saybrook, CT 06475

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