Old Saybrook, CT Homes

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  $699,500 Pending

  • Land
  • 8.11 Acres
  • $86,252 per Acre

  60 Ingham Hill Rd, Old Saybrook, CT 06475

  Picturesque waterfront 8.1-acre lot on the tranquil Oyster River in historic Old Saybrook. 1,400 feet of river frontage leading to Long Island Sound. Currently set as farmland, this could be a home run for builders sensitive to the needs of the land. With its beauty, you have 50-plus feet of road frontage and large footprint within the 50-foot tidal wetlands setback. I-95 is easily accessible,

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 735-1229

  60 Ingham Hill Rd, Old Saybrook, CT 06475
• Explore Old Saybrook

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  $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
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  $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

  Last Listing Agent Lorenda DiMeo Century 21 AllPoints Realty

  143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475
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  Est $572,285 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  6 Briarwood Dr, Old Saybrook, CT 06475

  6 Briarwood Dr, Old Saybrook, CT 06475
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  /36

  $849,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,898 Sq Ft

  26 College St, Old Saybrook, CT 06475

  Discover a truly enchanting antique home nestled in the heart of Old Saybrook's quaint, historic charm. This beautiful 4/5 bedroom residence overflows with character and period details, offering a rare opportunity to own a piece of local history. Adding to its significant appeal is a separate guest suite, providing an excellent private space for guests or extended family. Experience small-town

  

  Tammy Tinnerello

  William Pitt Sotheby's Int'l

  (860) 532-7885

  26 College St, Old Saybrook, CT 06475
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  $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 Finch William Pitt Sotheby's Int'l

  43 Pennywise Ln, Old Saybrook, CT 06475
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  $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 $964,625

  Last Listing Agent Terry McDonald McDonald Real Estate, LLC

  40 Seabreeze Rd, Old Saybrook, CT 06475
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  Est $833,250 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  Unlisted Address

  Unlisted Address
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  $1,399,900 Open Sun 12PM - 2PM

  • 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

  

  Jodi Serapilia

  William Raveis Real Estate

  (959) 500-5352

  105 Fenwood Dr, Old Saybrook, CT 06475
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  $2,350 - $4,365 total monthly price

  Saybrook Station Apartments

  1 - 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
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  $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 $1,379,443

  Last Listing Agent Alyssa Gambell William Raveis Real Estate

  11 Chandler St, Old Saybrook, CT 06475
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  Est $1,589,408 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,580 Sq Ft

  23 Red Bird Trail, Old Saybrook, CT 06475

  23 Red Bird Trail, Old Saybrook, CT 06475
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  $995,000

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

  1333A Boston Post Rd, Old Saybrook, CT 06475

  1.25 Acres in B4 Zone. Public water available, septic required. Traffic count 15,900. Within 1/2 mile of national tenants.

  Ron Lyman Lyman Real Estate

  1333A Boston Post Rd, Old Saybrook, CT 06475
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  $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

  Katherine Smith Berkshire Hathaway NE Prop.

  33 Beach Rd W, Old Saybrook, CT 06475
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  $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

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  10 Cricket Ct, Old Saybrook, CT 06475
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  Est $6,402,496 Not Listed For Sale

  • 7 Beds
  • 5.5 Baths
  • 7,465 Sq Ft

  9 Pettipaug Ave, Old Saybrook, CT 06475

  9 Pettipaug Ave, Old Saybrook, CT 06475
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  $1,045,000

  • 2 Beds
  • 2 Baths
  • 1,952 Sq Ft

  24 Seabreeze Rd, Old Saybrook, CT 06475

  Nestled in the prestigious Cornfield Point Beach Association neighborhood, this upgraded ranch offers one-level living at its finest with ocean views! With upgrades and improvements including new flooring, active solar, Thermopane windows, Vinyl Siding, central air, a huge bonus room you can convert to a third bedroom, this home provides comfort and style. A spacious open plan living room

  Brian Beaulieu KW Legacy Partners

  24 Seabreeze Rd, Old Saybrook, CT 06475
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  $2,500 total monthly price

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

  22 Denmore Ln, Old Saybrook, CT 06475

  Enjoy comfort and privacy in this newly renovated 1-bedroom apartment in a quiet Old Saybrook neighborhood. The unit is attached to the home but fully separate, featuring its own private entrance and no shared interior spaces.Inside are brand-new matching GE appliances, including an all-in-one GE Profile washer/dryer, full-size refrigerator, oven, microwave, and dishwasher. The apartment

  22 Denmore Ln, Old Saybrook, CT 06475
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  $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 $692,304

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

  87 Chalker Beach Rd, Old Saybrook, CT 06475
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  Est $785,317 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,673 Sq Ft

  16 Fordham Trail, Old Saybrook, CT 06475

  16 Fordham Trail, Old Saybrook, CT 06475
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  $1,075,000

  • 3 Beds
  • 2.5 Baths
  • 2,467 Sq Ft

  122 Old Post Rd, Old Saybrook, CT 06475

  Did you ever dream of owning two vacation homes, one near the water within walking distance to a beach, and another quiet cabin somewhere in the mountains or woods where you are surrounded by natural beauty? This unique home is both! Tucked away on 2+ private acres in the coveted Indian Town Beach Association, it is a spacious custom-built post and beam timber frame with amenities that rival a

  Susan Malan William Pitt Sotheby's Int'l

  122 Old Post Rd, Old Saybrook, CT 06475
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  $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
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  $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

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

  175 Ferry Rd Unit 3, Old Saybrook, CT 06475
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  Est $607,360 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft

  1 Anchorage Ln, Old Saybrook, CT 06475

  1 Anchorage Ln, Old Saybrook, CT 06475
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  $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
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  /15

  $5,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,791 Sq Ft
  • House for Rent

  45 Farview Ave, Old Saybrook, CT 06475

  An opportunity for a year around costal leaving, close to downtown and beach. A Refined Coastal Estate in the Heart of Old Saybrook, Connecticut. Set on nearly an acre along a tranquil tidal inlet leading into the Ferry Point Marsh Wildlife Management Area, this coastal estate offers a rare blend of privacy, natural beauty, and enduring craftsmanship. A true retreat, where every element has been

  Svetlana Goletz Compass Connecticut, LLC

  45 Farview Ave, Old Saybrook, CT 06475
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  $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 $687,811

  Last Listing Agent Jamie Bell Berkshire Hathaway NE Prop.

  22 Gates Rd, Old Saybrook, CT 06475
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  Est $1,204,272 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,010 Sq Ft

  41 Cypress Rd, Old Saybrook, CT 06475

  41 Cypress Rd, Old Saybrook, CT 06475
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  $999,900

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

  1 Beamon Meadow Place, Old Saybrook, CT 06475

  Surrounded by natural beauty and overlooking an ever-changing marsh, this inviting coastal retreat offers rare privacy, scenic views, and coveted deeded beach rights to Cornfield Point Beach, just a stroll away. Set on 1.44 acres and approached by a charming private bridge, the property feels peacefully removed while remaining moments from the heart of Old Saybrook. The picturesque grounds framed

  Linda Toscano Coldwell Banker Realty

  1 Beamon Meadow Place, Old Saybrook, CT 06475
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  $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
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  $840,000 Sold May 15, 2025

  41 Meadowood Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,380 Sq Ft
  • Built 1961

  Last Sold Summary

  • 8% Above List Price
  • $353/SF
  • 2 Days On Market

  Current Estimated Value $858,979

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

  41 Meadowood Ln, Old Saybrook, CT 06475
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  Est $694,735 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,924 Sq Ft

  10 Allendale Rd, Old Saybrook, CT 06475

  10 Allendale Rd, Old Saybrook, CT 06475
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  $949,900

  • 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
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  $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
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  $707,500 Sold Dec 19, 2025

  355 Main St, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 2,194 Sq Ft
  • Built 1919

  Last Sold Summary

  • 6% Below List Price
  • $322/SF
  • 187 Days On Market

  Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

  355 Main St, Old Saybrook, CT 06475
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  Est $2,412,019 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,225 Sq Ft

  468 Main St, Old Saybrook, CT 06475

  468 Main St, Old Saybrook, CT 06475
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  $985,000

  • 5 Beds
  • 2.5 Baths
  • 3,472 Sq Ft

  0 Town Beach Rd, Old Saybrook, CT 06475

  Enjoy your summers at Cornfield Point with a 5 bedroom Colonial with large of space for everyone. After a refreshing day at the beach come home to plenty of space for fun family gatherings. Parking is plentiful with extra storage. Your summers can be filled with boating, beaching, amazing sunsets, and fine dining at a many local restaurants. Don't miss your change to chance to live in Cornfield

  George Agnelli Agnelli Real Estate

  0 Town Beach Rd, Old Saybrook, CT 06475
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  $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, 2025, through June 20, 2026! 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

  Lynn Lehrman Re/Max Valley Shore

  17 Agawam Ave, Old Saybrook, CT 06475
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  $1,200,000 Sold Jan 05, 2026

  25 Maplewood Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 2,850 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $421/SF
  • 97 Days On Market

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  25 Maplewood Rd, Old Saybrook, CT 06475
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  Est $639,782 Not Listed For Sale

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

  21 Baum Ave, Old Saybrook, CT 06475

  21 Baum Ave, Old Saybrook, CT 06475

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