Old Saybrook, CT Homes

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  /40

  $949,000

  • 4 Beds
  • 2 Baths
  • 2,249 Sq Ft

  86 Chalker Beach Rd, Old Saybrook, CT 06475

  Welcome to Year-Round Beach Living with Room to Spare! Welcome to 86 Chalker Beach Rd. Do you desire a year-round beach home with plenty of space? Look no further! Welcome to 86 Chalker Beach Rd-your gateway to coastal living in one of Old Saybrook's most vibrant beach communities. With nearly 2,300 square feet of living space, this rare find offers four spacious bedrooms and two full bathrooms,

  

  Jodi Serapilia

  William Raveis Real Estate

  (860) 809-5460

  86 Chalker Beach Rd, Old Saybrook, CT 06475
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  /32

  $3,500 per month

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Apartment for Rent

  725 Boston Post Rd, Old Saybrook, CT 06475

  Updated 4-Bedroom, 2-Bathroom Year-Round Rental in the Heart of Old Saybrook Enjoy the convenience of living just steps from downtown Old Saybrook, with easy access to restaurants, shops, and stunning beaches. This beautifully updated home features a newly renovated kitchen with an open-concept design, Corian countertops, stainless steel appliances, and a spacious island with additional seating.

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 905-0075

  725 Boston Post Rd, Old Saybrook, CT 06475
• 

  $550,000 Sold Jun 09, 2025

  • 2,112 Sq Ft
  • $260/SF
  • 44 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1957

  69 Essex Rd, Old Saybrook, CT 06475

  ***OFFERING A $5000 closing cost credit to buyers!!! Welcome to this spacious Cape-style home offering over 2,000 sq ft of living space, nestled in the desirable Ferry Point neighborhood. Just steps from a 10' right of way to the Connecticut River, this home is perfect for those who love the water and the outdoors. Inside, you'll find beautiful hardwood floors, a first-floor bedroom and full bath

  Brittany O'Hara William Raveis Real Estate

  69 Essex Rd, Old Saybrook, CT 06475
• 

  Est $536,708 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,930 Sq Ft

  175 Ferry Rd Unit 11, Old Saybrook, CT 06475

  175 Ferry Rd Unit 11, Old Saybrook, CT 06475
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  /33

  $575,000

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  5 Aladdin Ave, Old Saybrook, CT 06475

  GET YOUR SPOT AT THE BEACH! The perfect getaway, just a short walk from the Chalker Beach Sandy Shoreline. Ready for love, sun, swim, and enjoying all the fun-with no traffic and plenty of relaxation right outside this home. A spacious deck overlooks a beautiful backyard, ideal for entertaining family and friends. Rinse off the day in the outdoor shower. Chalker Beach offers an abundance of

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 590-4441

  5 Aladdin Ave, Old Saybrook, CT 06475
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  /35

  $3,265 - $3,500 per month

  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
• 

  $745,000 Sold Jun 06, 2025

  • 2,152 Sq Ft
  • $346/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  107 Ayers Point Rd, Old Saybrook, CT 06475

  Enjoy the ease of one-floor living in a serene, private setting with this charming ranch style home nestled on a full acre just moments from the Connecticut River and the scenic Turtle Creek Preserve-perfect for daily walks and enjoying nature. Designed with comfort and convenience in mind, this spacious residence features generously sized rooms, both formal and informal living spaces, and ample

  Joel Lucas Coldwell Banker Realty

  107 Ayers Point Rd, Old Saybrook, CT 06475
• 

  Est $633,032 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  24 Willard St, Old Saybrook, CT 06475

  24 Willard St, Old Saybrook, CT 06475
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  /37

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,812 Sq Ft

  14 Meadowood Ln, Old Saybrook, CT 06475

  Make this warm, inviting home your own this spring! Ideally located in one of the most desirable neighborhoods in town and conveniently located a short walk to the high school and close to beaches and the village. This home offers a very flexible floor plan with hardwood floors, a new roof and recently replaced septic system. A spacious, private deck with a hot tub complete the package! Schedule

  

  Rick Allen

  William Raveis Real Estate

  (860) 773-4719

  14 Meadowood Ln, Old Saybrook, CT 06475
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  /9

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  9A Cedarwood Ln, Old Saybrook, CT 06475

  Academic Rental Only - available September 1, 2025, to May 31, 2026. The home is furnished. Lovely wooded half an acre in a quiet neighborhood. Beach rights to Cornfield Point Beach. Pets are to be considered on a case-by-case basis. A credit check, security deposit, and lease are required.

  Nick Prevost William Raveis Real Estate

  9A Cedarwood Ln, Old Saybrook, CT 06475
• 

  $490,000 Sold Jun 04, 2025

  • 1,740 Sq Ft
  • $282/SF
  • 4 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1972

  10 Cricket Ct, Old Saybrook, CT 06475

  A Diamond in the Rough that offers Tremendous Potential! Located in the desirable Cricket Court neighborhood of Old Saybrook, this traditional 3-bedroom, 1 & 1/2 bath colonial offers 1,740 square feet of living space on a spacious 1/2-acre lot with a fenced in back yard. With a 2-car attached garage, an oversized deck, underground utilities and a prime location close to town, Saybrook Point, and

  Kevin Kennedy Kennedy Real Estate Solutions

  10 Cricket Ct, Old Saybrook, CT 06475
• 

  Est $631,324 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  40 Bokum Rd, Old Saybrook, CT 06475

  40 Bokum Rd, Old Saybrook, CT 06475
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  /23

  $699,500

  • Land
  • 8 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 100-foot inland wetlands setback. I-95 is easily accessible,

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 735-1229

  60 Ingham Hill Rd, Old Saybrook, CT 06475
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  /40

  $5,250 per month

  • 4 Beds
  • 4 Baths
  • 2,686 Sq Ft
  • House for Rent

  6 Barton Ave, Old Saybrook, CT 06475

  FURNISHED ACADEMIC RENTAL AVAILABLE FROM OCTOBER 1, 2025 - MAY 15, 2026. Welcome to the Oyster River and Saybrook Cove where you can move into this fully furnished rental and you will not need anything other than your personal effects. A lovely open concept remodel with a bright window filled living room, gourmet kitchen, and two areas for dining. The outdoor backyard patio is well equipped with

  Kara Bell J.M. REALTY

  6 Barton Ave, Old Saybrook, CT 06475
• 

  $5,995,000 Sold Jun 03, 2025

  • 5,592 Sq Ft
  • $1072/SF
  • 4 Days On Market

  • 6 Beds
  • 8 Baths
  • Built 1732

  91 N Cove Rd, Old Saybrook, CT 06475

  A masterful fusion of Colonial New England heritage and refined modernity, this landmark estate has been meticulously reimagined through a comprehensive 2020 restoration. Every element has been crafted with precision, marrying historic authenticity with world-class design. Upon entry, the home reveals a breathtaking harmony of 18th-century character and contemporary sophistication-oak floors,

  Angela Ruel Berkshire Hathaway NE Prop.

  91 N Cove Rd, Old Saybrook, CT 06475
• 

  Est $763,071 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,502 Sq Ft

  456 Main St, Old Saybrook, CT 06475

  456 Main St, Old Saybrook, CT 06475
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  /40

  $695,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,830 Sq Ft

  100 Sheffield St Unit B4, Old Saybrook, CT 06475

  This creek/estuary facing unit at "The Cove" in the heart of Old Saybrook has been completely & tastefully remodeled! Enjoy shoreline living on North Cove within walking distance of North Cove Yacht Club as well as Main Street with it's restaurants, shops & of course the "Kate". It features water views of North Cove along with access to launch your kayak just outside your slider door! Amenities

  

  Kevin Geysen

  William Pitt Sotheby's Int'l

  (860) 385-8517

  100 Sheffield St Unit B4, Old Saybrook, CT 06475
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  /15

  $6,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • House for Rent

  25 W Shore Dr, Old Saybrook, CT 06475

  BEACHFRONT Beautifully renovated Furnished luxury waterfront monthly rental $6900 a month 9/30/25 to 5/15/26 (some flexibility with dates). Waterviews from all rooms, private beach, plus cornfield point assocation amenties. Enjoy 3 bedrooms all with water-views, 2 full bathrooms, 1 half bathroom, fireplace, CA, new gourmet kitchen, generator, in beautiful seaside setting and neighborhood. Sandy

  Joel Lucas Coldwell Banker Realty

  25 W Shore Dr, Old Saybrook, CT 06475
• 

  $697,000 Sold Jun 03, 2025

  • 2,315 Sq Ft
  • $301/SF
  • 18 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1948

  57 Lynde St, Old Saybrook, CT 06475

  Did I say FABULOUS?! A Cape with a contemporary twist and oozing with charm! You will be pleasantly surprised to discover spacious, sunny and inviting rooms with an open floor plan. The main living space boasts a tremendous great room with a large bay window and built ins. This room can accommodate a sitting area, a reading nook and dining area that opens into the kitchen. Culinary delights can

  Susan Malton Coldwell Banker Realty

  57 Lynde St, Old Saybrook, CT 06475
• 

  Est $1,788,742 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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  /40

  $995,900

  • 3 Beds
  • 2 Baths
  • 2,297 Sq Ft

  12 4th Ave, Old Saybrook, CT 06475

  Nestled on Ferry Point, where the Ct River meets the L.I. Sound, this charming waterfront home offers breathtaking views and direct access to the water. The private dock, complete with Jet ski port and well suited to an array of different boat designs,invites endless maritime adventures. Enjoy watching Osprey on their nest along with boats drifting by from the kitchen, living room, and dining

  

  Maddy Mattson

  Coldwell Banker Realty

  (860) 787-8257

  12 4th Ave, Old Saybrook, CT 06475
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  /14

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,052 Sq Ft
  • House for Rent

  16 Clearwater Rd, Old Saybrook, CT 06475

  *Academic Rental August - June* Welcome to 16 Clearwater Rd, Academic Rental that's fully furnished with 3 Bedrooms and 2 full baths. New flooring throughout the main floor with brand new bay windows that really make you feel at home. Open spaced living room that flows right into your dining room with plenty of space to sit and relax. Updated kitchen with all the cooking appliances you need to

  Marco Rondinone Berkshire Hathaway NE Prop.

  16 Clearwater Rd, Old Saybrook, CT 06475
• 

  $811,000 Sold Jun 02, 2025

  • 1,761 Sq Ft
  • $461/SF
  • 2 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1976

  17 Cricket Ct, Old Saybrook, CT 06475

  Beautiful beaches and the charming downtown of Old Saybrook are just minutes away from this tastefully remodeled Colonial style home. Enter through the front door and you are drawn to the sun soaked eat-in kitchen (remodeled 2020) with granite countertops and Frigidaire stainless steel appliances. The stunning kitchen opens to a family room with river rock fireplace (propane insert 2020) and

  Jessica Blancato William Pitt Sotheby's Int'l

  17 Cricket Ct, Old Saybrook, CT 06475
• 

  Est $601,477 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  99 Maple Ave, Old Saybrook, CT 06475

  99 Maple Ave, Old Saybrook, CT 06475
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  /26

  $1,200,000

  • 4 Beds
  • 2 Baths
  • 3,200 Sq Ft

  122 College St, Old Saybrook, CT 06475

  Iconic Old Saybrook 1890's Captain's home with it's own widow's walk-venture up and enjoy 360 degree views of the CT River, North Cove, and Long Island Sound-or relax on the wrap around porch and watch the world go by. Situated on .80 level acres w/an inground pool-2 car detached garage w/1/2 bath for the pool-possibly could be renovated for guest quarters. This home is like a blank slate w/3200

  Mary McDonald Coldwell Banker Realty

  122 College St, Old Saybrook, CT 06475
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  /19

  $2,400 per month

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • House for Rent

  38 Seabreeze Rd, Old Saybrook, CT 06475

  Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with three bedrooms, an updated bathroom, eat-in kitchen, living room with fireplace, a wonderful sun porch and an outside

  Terry McDonald McDonald Real Estate, LLC

  38 Seabreeze Rd, Old Saybrook, CT 06475
• 

  $847,500 Sold May 30, 2025

  • 2,424 Sq Ft
  • $350/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1969

  11 Crest Rd, Old Saybrook, CT 06475

  Welcome to 11 Crest Road in beautiful Old Saybrook, Connecticut! This tastefully maintained 3-bedroom, 2.5- bathroom 'L' shape ranch sits on an impressive 2.2-acre lot and offers 2,424 square feet of spacious, single-level living. Home office can also be used as a 4th bedroom. Located in a quiet community, this home features a warm and inviting layout with a cozy living room, a sun-drenched

  Eric Ryalls William Pitt Sotheby's Int'l

  11 Crest Rd, Old Saybrook, CT 06475
• 

  Est $6,711,830 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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  /28

  $849,000

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  12 Bellaire Dr, Old Saybrook, CT 06475

  Cornfield point ready to go back yard with pool like oasis low association charge, beach is rake daily all summer boat ramp beach parties golf cart parades palm trees a really fun place to live. Backyard has huge deck for privacy, tennis court and club house with a boat ramp. If you want to live somewhere and enjoy a nice friendly association this is it.

  George Agnelli Agnelli Real Estate

  12 Bellaire Dr, Old Saybrook, CT 06475
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  /12

  $2,400 per month

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

  41 Town Beach Rd, Old Saybrook, CT 06475

  Academic lease only. Fully furnished rental available 9/2/25. Sparkling clean, hurry, this one won't last! Remodeled kitchen, fenced in back yard, new furniture, fireplace. Owner is a licensed Broker in the State of Connecticut. a great little place to live amazing sunsets trash pick up included

  George Agnelli Agnelli Real Estate

  41 Town Beach Rd, Old Saybrook, CT 06475
• 

  $560,000 Sold May 29, 2025

  • 1,203 Sq Ft
  • $466/SF
  • 70 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1926

  15 Waterbury Ave, Old Saybrook, CT 06475

  Welcome to Saybrook Manor, one of Old Saybrook's most desirable coastal communities! This year-round 3-bedroom, 1.5-bathroom Cape-style within the Saybrook manor beach association offering access to sandy shores and calm waters-perfect for swimming, picnicking, or a leisurely shoreline stroll. Set on a .27-acre corner lot, this home features a beautifully remodeled kitchen with granite

  Eric Engdall Coldwell Banker Realty

  15 Waterbury Ave, Old Saybrook, CT 06475
• 

  Est $387,537 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  310 Springbrook Rd, Old Saybrook, CT 06475

  310 Springbrook Rd, Old Saybrook, CT 06475
• 

  

  /19

  $949,900

  • 3 Beds
  • 1 Bath
  • 762 Sq Ft

  27 Barnes Rd, Old Saybrook, CT 06475

  After being cherished by the same family for 70 years, this quintessential New England cottage ON THE WATER of Long Island Sound is ready for its next chapter. Located in the much sought after summer beach community of Great Hammock Beach, this property, situated on an oversized lot, offers direct access to fishing, swimming, kayaking and breathtaking sunset views from the deck. Inside, you'll

  Debra Pliego Essentia Realty

  27 Barnes Rd, Old Saybrook, CT 06475
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  /20

  $2,950 per month

  • 3 Beds
  • 1.5 Baths
  • 1,196 Sq Ft
  • House for Rent

  12 Allendale Rd, Old Saybrook, CT 06475

  Desirable MEADOW WOOD location -----Academic rental available between September 15, 2025 thru May 15, 2026. Wonderful FURNISHED home in cul-de-sac -- 1200 square foot ranch with central air, close to beaches, Peaceful area -- Walk to Dairy Queen, Luigi's Restaurant! One floor living offers renovated, modern open kitchen, dining room, living room. There are 3 spacious bedrooms. Generous sized

  Lisa Genovali Re/Max Valley Shore

  12 Allendale Rd, Old Saybrook, CT 06475
• 

  $1,460,000 Sold May 28, 2025

  • 4,792 Sq Ft
  • $305/SF
  • 83 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1979

  55 Otter Cove Dr, Old Saybrook, CT 06475

  Welcome to 55 Otter Cove Dr, a charming New England residence that offers an unparalleled multi-generational living experience in the prestigious Otter Cove Estates. This exquisite home, located in a serene community with private beach access to the Connecticut River, is more than just a house-it's a lifestyle. Property Features: 5 Beds, 4 Baths, 4,792 SqFt on 2.4 Acres with Water Views of the

  Kristina Demaria Coldwell Banker Realty

  55 Otter Cove Dr, Old Saybrook, CT 06475
• 

  Est $657,731 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,813 Sq Ft

  5 Crowley Dr, Old Saybrook, CT 06475

  5 Crowley Dr, Old Saybrook, CT 06475
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  /40

  $1,145,000

  • 3 Beds
  • 2.5 Baths
  • 3,286 Sq Ft

  1 Lighthouse Ln, Old Saybrook, CT 06475

  Set in coveted Saybrook Point, this Cape-style home blends coastal charm with thoughtful custom touches, offers STUNNING WATER VIEWS and is walkable to both the Point and town center. A spacious (3200+ sq.ft) home, features include built-ins, cabinetry, crown moldings and bay windows framing views of South Cove from multiple rooms. Step outside to a stone patio set beneath a graceful pergola,

  Lynne Ferrigno Coldwell Banker Realty

  1 Lighthouse Ln, Old Saybrook, CT 06475
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  /36

  $4,500 per month

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

  8 Belaire Manor, Old Saybrook, CT 06475

  Academic rental available November 1, 2025 - May 28, 2026 (year-round possible as well). 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 watch the panoramic sunrises and sunsets which are magical with colors ranging from cotton candy on one side of the beach to deep orange on

  Erika Raffles William Pitt Sotheby's Int'l

  8 Belaire Manor, Old Saybrook, CT 06475
• 

  $626,000 Sold May 21, 2025

  • 1,557 Sq Ft
  • $402/SF
  • 77 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1978

  140 Sandy Point Rd, Old Saybrook, CT 06475

  Dreaming of summer? Start right here with a private beach just a short stroll away in the desirable place to be, SummerWood on the Sound, for a vacation year round! Begin and end each day with gorgeous sunrises and sunsets of the marsh and LI Sound from your backyard! Walking up from the front steps past the foyer you will find, a rare half bath to the right, with a convenient laundry area to the

  Carolyn DiPietro Berkshire Hathaway NE Prop.

  140 Sandy Point Rd, Old Saybrook, CT 06475
• 

  Est $574,117 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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