6,258

Old Saybrook, CT Homes

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  • /38

    $675,000 Pending

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    2 Pequot Trail, Old Saybrook, CT 06475

    Welcome to 2 Pequot Trail, perfectly positioned within Old Saybrook's desirable Indian Town Association, this beautifully maintained coastal ranch offers a rare opportunity to enjoy shoreline living in one of the area's most established waterfront neighborhoods. This stunning home captures the relaxed charm and lifestyle that make Indian Town and Old Saybrook at large, so sought after. Completely

    Agent Photo

    Dylan Walter

    William Raveis Real Estate

    (860) 909-8203

    2 Pequot Trail, Old Saybrook, CT 06475
  • /35

    $2,950 - $4,270 per month plus fees

    Hanford Commons

    2 Beds

    99 Lynde St, Old Saybrook, CT 06475

    Welcome to Hanford Commons – The Definition of LuxuryDiscover modern living at its finest with our brand-new apartments in the picturesque town of Old Saybrook. Hanford Commons perfectly blends style, convenience, and comfort, offering you a home that exceeds expectations. Each thoughtfully designed unit features stainless steel appliances, an in-unit washer and dryer, central heating and

    99 Lynde St, Old Saybrook, CT 06475
  • 99 Maple Ave, Old Saybrook, CT 06475

    $675,000 Sold Feb 20, 2026

    99 Maple Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Above List Price
    • $577/SF
    • 34 Days On Market

    Current Estimated Value $636,670

    Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l

    99 Maple Ave, Old Saybrook, CT 06475
    • 11 Evans Ln, Old Saybrook, CT 06475

      Est $455,729 Not Listed For Sale

      11 Evans Ln, Old Saybrook, CT 06475

      • 2 Beds
      • 1 Bath
      • 684 Sq Ft
      • Built 1938
      11 Evans Ln, Old Saybrook, CT 06475

      Last Sold Summary

      • 2% Above List Price
      • $651/SF
      • 40 Days On Market

      Last Sold Price $445,000

      Last Listing Agent Jordan Ostrofsky LPT Realty

  • /40

    $840,000 Under Contract

    • 4 Beds
    • 1.5 Baths
    • 2,005 Sq Ft

    11 S View Terrace, Old Saybrook, CT 06475

    Perfectly positioned in one of Old Saybrook's most desirable shoreline neighborhoods, this beautifully updated 4-bedroom home offers the coastal lifestyle buyers dream about. Sun-filled living spaces and thoughtful updates create a setting that feels both refined and relaxed. Homes in locations like this rarely become available. Offering 2,005 square feet of inviting living space, the home has

    Agent Photo

    Dylan Walter

    William Raveis Real Estate

    (860) 775-7259

    11 S View Terrace, Old Saybrook, CT 06475
  • /22

    $3,500 total monthly price

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

    102 Chalker Beach Rd, Old Saybrook, CT 06475

    2026 Beach cottage -- April 15 to Oct 15 -- $3,500/month. One lucky renter will get to spend spring, summer, and fall in this charming Chalker Beach cottage! Located in a private association, this home is just a short walk to the large soft-sand beach. Walk for miles along adjoining beaches and neighborhoods during the day, and enjoy the magical pastel sunsets over the ocean at night. Inside,

    Erika Raffles William Pitt Sotheby's Int'l

    102 Chalker Beach Rd, 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 $551,658

    Last Listing Agent Lorenda DiMeo Century 21 AllPoints Realty

    143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475
    • 73 Ayers Point Rd, Old Saybrook, CT 06475

      Est $661,087 Not Listed For Sale

      73 Ayers Point Rd, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 1,861 Sq Ft
      • Built 1955
      73 Ayers Point Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 6% Above List Price
      • $336/SF
      • 34 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Lisa Genovali RE/MAX

  • /29

    $1,399,900 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,910 Sq Ft

    105 Fenwood Dr, Old Saybrook, CT 06475

    Welcome to 105 Fenwood Drive, nestled in the peaceful and picturesque community of Fenwood Beach Association. Experience waterfront living surrounded by natural beauty-where ospreys, great blue herons, and wintering bald eagles soar above thriving estuarine wetlands. Enjoy a short walk to the beach or an evening stroll to the causeway to watch the sunset. This golf cart friendly neighborhood

    Agent Photo

    Jodi Serapilia

    William Raveis Real Estate

    (959) 500-5352

    105 Fenwood Dr, Old Saybrook, CT 06475
  • /23

    $3,539 - $4,517 total monthly price

    Saybrook Station

    2 Beds

    7 N Main St, Old Saybrook, CT 06475

    Located in Old Saybrook, with easy access to Main Street and Boston Post Road, Saybrook Station Apartments are just a quick jaunt to the train station, a four-minute drive to the historic Town Green, and minutes away from 1000 acres of coastal forest at The Preserve. Not to mention, all of the shopping, dining, and entertainment that nearby New Haven has to offer. Picture coming home every day to

    7 N Main St, Old Saybrook, CT 06475
  • 40 Seabreeze Rd, Old Saybrook, CT 06475

    $952,000 Sold Mar 31, 2025

    40 Seabreeze Rd, Old Saybrook, CT 06475

    • 5 Beds
    • 1.5 Baths
    • 1,936 Sq Ft
    • Built 1943

    Last Sold Summary

    • 12% Above List Price
    • $492/SF
    • 10 Days On Market

    Current Estimated Value $1,023,987

    Last Listing Agent Terry McDonald McDonald Real Estate, LLC

    40 Seabreeze Rd, Old Saybrook, CT 06475
    • 9 Trolley Crossing, Old Saybrook, CT 06475

      Est $634,241 Not Listed For Sale

      9 Trolley Crossing, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 1,453 Sq Ft
      • Built 1973
      9 Trolley Crossing, Old Saybrook, CT 06475

      Last Sold Summary

      • 6% Above List Price
      • $413/SF
      • 40 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Jackie Lyman Lyman Real Estate

  • /2

    $995,000

    • Land
    • 1.25 Acres
    • $796,000 per Acre

    1333A Boston Post Rd, Old Saybrook, CT 06475

    An exceptional opportunity - Nestled on 1.25 acres of vacant land with public water access, this prime property is located in the sought-after Gateway Business B-4 District Within mile of national tenants, boasting a daily traffic count of 15,900. This versatile lot is zoned for a variety of uses such as retail stores, professional offices, medical clinics, theaters, and more. Its

    Ron Lyman Lyman Real Estate Brokerage & Development

    1333A Boston Post Rd, Old Saybrook, CT 06475
  • /31

    $3,000 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • House for Rent

    43 Pennywise Ln, Old Saybrook, CT 06475

    Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen

    Phoebe Schreiner William Pitt Sotheby's Int'l

    43 Pennywise Ln, Old Saybrook, CT 06475
  • 11 Chandler St, Old Saybrook, CT 06475

    $1,420,000 Sold Apr 11, 2025

    11 Chandler St, Old Saybrook, CT 06475

    • 3 Beds
    • 3 Baths
    • 2,052 Sq Ft
    • Built 2006

    Last Sold Summary

    • 29% Below List Price
    • $692/SF
    • 166 Days On Market

    Current Estimated Value $1,466,375

    Last Listing Agent Alyssa Gambell William Raveis Real Estate

    11 Chandler St, Old Saybrook, CT 06475
    • 35 Sherwood Terrace, Old Saybrook, CT 06475

      Est $645,812 Not Listed For Sale

      35 Sherwood Terrace, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 1,834 Sq Ft
      • Built 1984
      35 Sherwood Terrace, Old Saybrook, CT 06475

      Last Sold Summary

      • 6% Above List Price
      • $333/SF
      • 25 Days On Market

      Last Sold Price $610,000

      Last Listing Agent Jennifer Gurnell William Raveis Real Estate

  • /35

    $924,900 Open Sun 1PM - 3PM

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

    23 Clinton Ave, Old Saybrook, CT 06475

    Welcome to 23 Clinton Avenue, Old Saybrook - a stunning, fully renovated 3-bedroom, 2-bathroom home spanning 1,500 square feet, where modern farmhouse charm meets coastal elegance. Just a few hundred feet from the water and over a mile from the Old Saybrook Point Inn, this picture-perfect retreat is ideally situated for convenient access to downtown, the town beach, and the Fenwick area. Whether

    Luke Florian SSG Real Estate LLC

    23 Clinton Ave, Old Saybrook, CT 06475
  • /32

    $4,500 total monthly price

    • 4 Beds
    • 1.5 Baths
    • 1,316 Sq Ft
    • House for Rent

    33 Beach Rd W, Old Saybrook, CT 06475

    Adorable 4-bedroom, 1-1/2 bath beachfront retreat available as an academic rental from early September through the end of May in the highly sought-after Chalker Beach neighborhood of Old Saybrook. Offered fully furnished with all utilities included, this charming coastal home that was completely rebuilt in 1986 is the perfect place to enjoy off-season shoreline living. Warm coastal wood paneling

    Katie Smith Berkshire Hathaway NE Prop.

    33 Beach Rd W, 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 $447,621

    Last Listing Agent Bob Yostos Coldwell Banker Realty

    254 Hidden Cove Rd, Old Saybrook, CT 06475
    • 23 Red Bird Trail, Old Saybrook, CT 06475

      Est $1,501,475 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

      • 2% Above List Price
      • $572/SF
      • 158 Days On Market

      Last Sold Price $1,475,000

      Last Listing Agent Jay Cusack Executive Real Estate

  • /40

    $1,350,000

    • 4 Beds
    • 2.5 Baths
    • 3,301 Sq Ft

    6 Parkman Place, Old Saybrook, CT 06475

    Nestled on a quiet cul-de-sac in the heart of the Connecticut River Shoreline, this stunning 3,301 SF, 4-bedroom, 2.1 bath home represents a masterclass in coastal sophistication. Meticulously renovated, this residence offers a rare combination of high-end design, graceful grounds, and absolute peace of mind and privacy, situated in a town recognized as one of the top ten places to live in

    Rick Weiner William Pitt Sotheby's Int'l

    6 Parkman Place, Old Saybrook, CT 06475
  • /4

    $1,300 total monthly price

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • House for Rent

    1500 Boston Post Rd Unit 8, Old Saybrook, CT 06475

    Studio unit includes heat, hot water, electricity, cable, and internet. Recently remodeled. Clean and freshly painted. Private bath. Parking available. Conveniently located. Walking distance to beach.

    Brian Botti Botti Realty

    1500 Boston Post Rd Unit 8, Old Saybrook, CT 06475
  • 10 Cricket Ct, Old Saybrook, CT 06475

    $941,500 Sold Jan 22, 2026

    10 Cricket Ct, Old Saybrook, CT 06475

    • 3 Beds
    • 1.5 Baths
    • 1,740 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Above List Price
    • $541/SF
    • 24 Days On Market

    Current Estimated Value $894,354

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    10 Cricket Ct, Old Saybrook, CT 06475
    • 9 Pettipaug Ave, Old Saybrook, CT 06475

      Est $6,450,891 Not Listed For Sale

      9 Pettipaug Ave, Old Saybrook, CT 06475

      • 7 Beds
      • 5.5 Baths
      • 7,465 Sq Ft
      • Built 1905
      9 Pettipaug Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 2% Below List Price
      • $881/SF
      • 19 Days On Market

      Last Sold Price $6,575,000

      Last Listing Agent Christine Poppy Compass Connecticut, LLC

  • /36

    $1,450,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,560 Sq Ft

    24 Church St, Old Saybrook, CT 06475

    RARELY AVAILABLE NEW CONSTRUCTION IN NORTH COVE! This modern farmhouse-style Cape, built in 2023 in sought after North Cove, offers over 2,500 sq ft of bright, open living space. The high-end kitchen features a large center island, pantry, quartz countertops, and GE Cafe appliances including a duel fuel oven/stove. The layout includes 3 bedrooms and 3 full baths, with the flexibility to create a

    Lynn Toper CR Premier Properties

    24 Church St, Old Saybrook, CT 06475
  • /31

    $3,000 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft
    • House for Rent

    38 Mohican Rd, Old Saybrook, CT 06475

    This home is just one short block from the beach and has a nice sized yard with a patio and outdoor shower. The roomy kitchen opens to a large great room with a gas burning stove. There is also a separate living room to the front of the house. This home has plenty of room for parking and is a member of Cornfield Point with two beaches, a club house, pickleball court, tennis court and activities

    Bonnie Fillion Berkshire Hathaway NE Prop.

    38 Mohican Rd, Old Saybrook, CT 06475
  • 87 Chalker Beach Rd, Old Saybrook, CT 06475

    $699,000 Sold May 09, 2025

    87 Chalker Beach Rd, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft
    • Built 1961

    Last Sold Summary

    • $713/SF
    • 15 Days On Market

    Current Estimated Value $706,308

    Last Listing Agent Jay Lafleur William Pitt Sotheby's Int'l

    87 Chalker Beach Rd, Old Saybrook, CT 06475
    • 16 Fordham Trail, Old Saybrook, CT 06475

      Est $823,677 Not Listed For Sale

      16 Fordham Trail, Old Saybrook, CT 06475

      • 4 Beds
      • 2.5 Baths
      • 3,673 Sq Ft
      • Built 1992
      16 Fordham Trail, Old Saybrook, CT 06475

      Last Sold Summary

      • 22% Above List Price
      • $184/SF
      • 29 Days On Market

      Last Sold Price $675,000

      Last Listing Agent WAYNE ARUTE Law Realty Group

  • /40

    $949,900

    • 3 Beds
    • 2.5 Baths
    • 1,632 Sq Ft

    1 Beamon Meadow Place, Old Saybrook, CT 06475

    Tucked away in a tranquil setting overlooking an ever changing tidal marsh, this exceptional coastal retreat offers a rare blend of privacy, natural beauty, and coveted deeded access to Cornfield Point Beach just a short stroll away. Privately set on 1.44 acres and approached by a charming bridge, the property feels like a hidden sanctuary while remaining just moments from the vibrant heart of

    Linda Toscano Coldwell Banker Realty

    1 Beamon Meadow Place, Old Saybrook, CT 06475
  • /32

    $4,000 total monthly price

    • 4 Beds
    • 1.5 Baths
    • 2,180 Sq Ft
    • House for Rent

    422 Maple Ave, Old Saybrook, CT 06475

    Classic New England year round beach house across the street from the ocean in the private Knollwood beach area. This home has 4 bedrooms, 2 full baths and an outside shower ! Master bedroom has a king bed, 2nd bedroom has a full size bed, 3rd bedroom has a queen size bed and 4th bedroom has a full and twin bed. Stunning views on every side and amazing sunsets ! This is a great location the

    Dawn Caso Williams Realty Services

    422 Maple Ave, Old Saybrook, CT 06475
  • 175 Ferry Rd Unit 3, Old Saybrook, CT 06475

    $565,000 Sold Jan 09, 2026

    175 Ferry Rd Unit 3, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $338/SF
    • 77 Days On Market

    Current Estimated Value $583,768

    Last Listing Agent Kathy Schellens William Pitt Sotheby's Int'l

    175 Ferry Rd Unit 3, Old Saybrook, CT 06475
    • 1 Anchorage Ln, Old Saybrook, CT 06475

      Est $632,017 Not Listed For Sale

      1 Anchorage Ln, Old Saybrook, CT 06475

      • 5 Beds
      • 3 Baths
      • 1,840 Sq Ft
      • Built 1955
      1 Anchorage Ln, Old Saybrook, CT 06475

      Last Sold Summary

      • 12% Above List Price
      • $307/SF
      • 140 Days On Market

      Last Sold Price $565,000

      Last Listing Agent Renee McCammon Berkshire Hathaway Home Services

  • /39

    $1,199,000 Open Sun 12PM - 2PM

    • 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
  • /40

    $6,500 total monthly price

    • 4 Beds
    • 3 Baths
    • 3,762 Sq Ft
    • House for Rent

    17 Agawam Ave, Old Saybrook, CT 06475

    Fantastic Opportunity to Rent in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage is available from September, 2026, through June 20, 2027! Boasting 4 bedrooms and 4 baths plus a huge third-floor rec room/bunk room space, the home offers over 3,700 sq. ft. of comfortable beach living. Open floor plan living room with walls of windows and French door access to a spacious back

    Lynn Lehrman Re/Max Valley Shore

    17 Agawam Ave, Old Saybrook, CT 06475
  • 11 Coulter St Unit 28, Old Saybrook, CT 06475

    $650,000 Sold Mar 16, 2026

    11 Coulter St Unit 28, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 2,099 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $310/SF
    • 5 Days On Market

    Current Estimated Value $634,871

    Last Listing Agent Christine Fappiano Shoreline Real Estate Company

    11 Coulter St Unit 28, Old Saybrook, CT 06475
    • 41 Cypress Rd, Old Saybrook, CT 06475

      Est $1,312,100 Not Listed For Sale

      41 Cypress Rd, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 3,010 Sq Ft
      • Built 1976
      41 Cypress Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 17% Above List Price
      • $374/SF
      • 84 Days On Market

      Last Sold Price $1,125,000

      Last Listing Agent Lynn Toper CR Premier Properties

  • /31

    $1,075,000

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

    12 Hill Rd, Old Saybrook, CT 06475

    Welcome to Otter Cove Estates, located in Old Saybrook Ct. Live in the established area of residential homes that offer large lots of 2 acres at the mouth of the Ct River. This home offers 3 bedrooms with Master suite on the first floor with ensuite. Open floor plan large kitchen, built in newer appliances subzero built in fridge, Electrolux double ovens, Bosch dishwasher and newer microwave.

    Paula Stuart Berkshire Hathaway NE Prop.

    12 Hill Rd, Old Saybrook, CT 06475
  • /36

    $18,000 total monthly price

    • 4 Beds
    • 3 Baths
    • 1,120 Sq Ft
    • House for Rent

    8 Belaire Manor, Old Saybrook, CT 06475

    Summer 2026 -- Available: June 15-30 for $9,000 -- Rented: July/Aug/Sept. 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

    Erika Raffles William Pitt Sotheby's Int'l

    8 Belaire Manor, Old Saybrook, CT 06475
  • 22 Gates Rd, Old Saybrook, CT 06475

    $676,100 Sold Apr 22, 2025

    22 Gates Rd, Old Saybrook, CT 06475

    • 2 Beds
    • 1 Bath
    • 1,020 Sq Ft
    • Built 1948

    Last Sold Summary

    • 8% Above List Price
    • $663/SF
    • 3 Days On Market

    Current Estimated Value $703,451

    Last Listing Agent Jamie Bell Berkshire Hathaway NE Prop.

    22 Gates Rd, Old Saybrook, CT 06475
    • 10 Allendale Rd, Old Saybrook, CT 06475

      Est $710,146 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

      • 8% Above List Price
      • $343/SF
      • 91 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Dana Gibson William Raveis Real Estate

Showing Results 1 - 40, Page 1 of 18

Home Trends in Old Saybrook, CT

Housing Trends

Median Sale Price
$717,500
Median Single Family Sale Price
$763,250
Median Townhouse Sale Price
$540,000
Median 2 Bedroom Sale Price
$560,000
Median 1 Bedroom Sale Price
$215,000
Average Price Per Sq Ft
$493
Number of Homes for Sale
18
Last 12 months Home Sales
142
Months of Supply
1.50
Median List Price
$749,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
5%
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