Old Saybrook, CT Homes

• 

  Est $1,841,412

  Not Listed For Sale

  16 Fenbrook Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 4.5 Baths
  • 3,036 Sq Ft
  • Built 2007

  16 Fenbrook Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Jason Malagutti Dave Jones Realty, LLC
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  /9

  $1,750,000

  • Land
  • 20,037 Sq Ft
  • $3,804,348 per Acre

  101-A Sequassen Ave, Old Saybrook, CT 06475

  APPROVED OCEANFRONT LOT - WALK TO THE BEACH FROM YOUR BACKYARD Design the life you've always envisioned. Whether you dream of a timeless shingle-style coastal retreat or a striking modern waterfront masterpiece, this exceptional homesite offers the perfect canvas to bring your vision to life. This fully approved, level building lot is ready for construction, allowing you to move forward with

  Fationa Meco Houlihan Lawrence WD

  101-A Sequassen Ave, Old Saybrook, CT 06475
• 

  $566,000

  Sold Oct 01, 2025

  14 Watrous Point Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft
  • Built 1966

  Last Sold Summary

  • 13% Below List Price
  • $263/SF
  • 3 Days On Market

  Current Estimated Value $681,481

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  14 Watrous Point Rd, Old Saybrook, CT 06475
• 

  Est $585,445

  Not Listed For Sale

  64 Obed Heights, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Built 1958

  64 Obed Heights, Old Saybrook, CT 06475

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Joshua Young Berkshire Hathaway NE Prop.
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  /39

  $1,850,000

  Open Sun 10AM - 12PM $350K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,188 Sq Ft

  108 Maple Ave, Old Saybrook, CT 06475

  Contemporary coastal elegance meets exceptional privacy along South Cove in Old Saybrook. Set on an extraordinary 1.8-acre parcel, this cedar-sided, 3,188-square-foot residence offers breathtaking water views from nearly every room and a setting that is virtually impossible to recreate. Originally built in 1965 and thoughtfully rebuilt in 1991, the home was designed to capture its spectacular

  Jessica Blancato William Pitt Sotheby's Int'l

  108 Maple Ave, Old Saybrook, CT 06475
• 

  $695,000

  Sold Nov 21, 2025

  117 Ayers Point Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,824 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $246/SF
  • 63 Days On Market

  Current Estimated Value $787,936

  Last Listing Agent Chloe White KW Legacy Partners

  117 Ayers Point Rd, Old Saybrook, CT 06475
• 

  Est $887,571

  Not Listed For Sale

  5 Watch Hill Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 2,630 Sq Ft
  • Built 1980

  5 Watch Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 151 Days On Market

  Last Listing Agent Kevin Geysen William Pitt Sotheby's Int'l
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  /40

  $1,025,000

  Open Sun 11AM - 1PM $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  37 Woodland Dr, Old Saybrook, CT 06475

  Experience coastal luxury in this stunning 3-bedroom, 2-bathroom ranch style home nestled in Knollwood Beach. Set on a rare .33 acre lot, it offers picturesque marsh and South Cove views. Step inside to discover a newly remodeled interior featuring an expansive remodeled white kitchen with quartz counters, large center island. The family room boasts a dramatic fireplace, while a sunlit dining

  Joel Lucas Coldwell Banker Realty

  37 Woodland Dr, Old Saybrook, CT 06475
• 

  $1,425,000

  Sold Apr 23, 2026

  24 Church St, Old Saybrook, CT 06475

  • 3 Beds
  • 3 Baths
  • 2,560 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $557/SF
  • 18 Days On Market

  Current Estimated Value $1,438,851

  Last Listing Agent Lynn Toper CR Premier Properties

  24 Church St, Old Saybrook, CT 06475
• 

  Est $1,332,528

  Not Listed For Sale

  15 Crest Rd, Old Saybrook, CT 06475

  • 5 Beds
  • 4.5 Baths
  • 2,884 Sq Ft
  • Built 1971

  15 Crest Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.
• 

  

  /38

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  119 Great Hammock Rd, Old Saybrook, CT 06475

  Every Day a Getaway! Some properties ask you to choose between full-time living & vacation living. Not this one. Set in the heart of Old Saybrook, this fully furnished 7-room Cape Cod delivers the ease of a residence with the spirit of a seasonal retreat - and comes with a private guest house. The main home offers 3 bdrms,, 2 baths & includes a coveted 1st fl bdrm for single-level living. A large

  Pardi & Zucco Team William Pitt Sotheby's Int'l

  119 Great Hammock Rd, Old Saybrook, CT 06475
• 

  $162,000

  Sold May 14, 2026

  6 South St, Old Saybrook, CT 06475

  • Land
  • 6,969 Sq Ft
  • $1,012,500 per Acre

  Last Sold Summary

  • 1% Above List Price
  • 16 Days On Market

  Current Estimated Value $158,451

  Last Listing Agent Katie Schubert KW Legacy Partners

  6 South St, Old Saybrook, CT 06475
• 

  Est $1,171,249

  Not Listed For Sale

  16 James Ct, Old Saybrook, CT 06475

  • 3 Beds
  • 3.5 Baths
  • 2,870 Sq Ft
  • Built 1995

  16 James Ct, Old Saybrook, CT 06475

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Colette Harron William Pitt Sotheby's Int'l
• 

  

  /31

  $529,000

  • 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
• 

  $625,000

  Sold Sep 19, 2025

  3 Glen Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,915 Sq Ft
  • Built 1969

  Last Sold Summary

  • $326/SF
  • 68 Days On Market

  Current Estimated Value $669,800

  Last Listing Agent Lisa Genovali Re/Max Valley Shore

  3 Glen Dr, Old Saybrook, CT 06475
• 

  Est $726,791

  Not Listed For Sale

  3 Pepperidge Trail, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1985

  3 Pepperidge Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.
• 

  

  /39

  $775,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 1,675 Sq Ft

  14 Seagull Rd, Old Saybrook, CT 06475

  Welcome to 14 Seagull Road, where the best of Connecticut shoreline living begins just outside your front door. Tucked within the sought-after Knollwood Beach community, this updated cape is just a 3-minute walk to the ocean. Enjoy waterfront strolls, kayaking, swimming, pickleball at the clubhouse, and spectacular sunsets over Long Island Sound. Knollwood Beach is more than a neighborhood...

  Kristina Quinones William Pitt Sotheby's Int'l

  14 Seagull Rd, Old Saybrook, CT 06475
• 

  $840,000

  Sold Jun 16, 2026

  1 Beamon Meadow Place, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $515/SF
  • 81 Days On Market

  Current Estimated Value $863,580

  Last Listing Agent Linda Toscano Coldwell Banker Realty

  1 Beamon Meadow Place, Old Saybrook, CT 06475
• 

  Est $629,306

  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
• 

  

  /12

  $12,000,000

  • 4 Beds
  • 1 Bath
  • 2,059 Sq Ft

  1445 Boston Post Rd, Old Saybrook, CT 06475

  A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a

  Casey Fisher Houlihan Lawrence WD

  1445 Boston Post Rd, Old Saybrook, CT 06475
• 

  $650,000

  Sold Nov 19, 2025

  12 Bellaire Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 1954

  Last Sold Summary

  • $589/SF
  • 8 Days On Market

  Current Estimated Value $697,772

  Last Listing Agent George Agnelli Agnelli Real Estate

  12 Bellaire Dr, Old Saybrook, CT 06475
• 

  Est $631,435

  Not Listed For Sale

  11 Coulter St Unit 21, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 1986

  11 Coulter St Unit 21, Old Saybrook, CT 06475

  Last Sold Summary

  • 43 Days On Market

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

  

  /32

  $699,000

  • 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
• 

  $840,000

  Sold May 08, 2026

  11 S View Terrace, Old Saybrook, CT 06475

  • 4 Beds
  • 1.5 Baths
  • 2,005 Sq Ft
  • Built 1964

  Last Sold Summary

  • $419/SF
  • 48 Days On Market

  Current Estimated Value $841,170

  Last Listing Agent Dylan Walter William Raveis Real Estate

  11 S View Terrace, Old Saybrook, CT 06475
• 

  Est $778,804

  Not Listed For Sale

  24 Pepperidge Trail, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 1987

  24 Pepperidge Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.
• 

  

  /31

  $585,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 2,149 Sq Ft

  207 School House Rd, Old Saybrook, CT 06475

  A rare opportunity awaits to become the second owner of this lovingly maintained ranch on desirable Schoolhouse Road. Thoughtfully designed for comfortable one-level living, this spacious 2,149-square-foot home offers four generously sized bedrooms, wide hallways, gleaming hardwood floors, and central air conditioning. Step inside to a welcoming living room featuring a classic wood-burning

  Tracy Lenz William Pitt Sotheby's Int'l

  207 School House Rd, Old Saybrook, CT 06475
• 

  $430,000

  Sold Oct 03, 2025

  258 School House Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • Built 1967

  Last Sold Summary

  • 4% Below List Price
  • $269/SF
  • 48 Days On Market

  Current Estimated Value $490,363

  Last Listing Agent Tim O'Hara William Raveis Real Estate

  258 School House Rd, Old Saybrook, CT 06475
• 

  Est $636,219

  Not Listed For Sale

  20 George Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1957

  20 George Dr, Old Saybrook, CT 06475

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Joel Lucas Coldwell Banker Realty
• 

  

  /38

  $1,425,000

  $565K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,745 Sq Ft

  4 Beach Rd, Old Saybrook, CT 06475

  DEEDED BEACH RIGHTS TO CORNFIELD POINT! One of Old Saybrook's most sought after beach communities! Enjoy beach days, sunset strolls, and the relaxed charm of shoreline living. This impeccably maintained Nantucket-style reverse floor plan home promotes scenic views from upper level main living space with private primary ensuite and 1st floor indoor/outdoor entertainment suite below offering

  Sharon Linder Berkshire Hathaway NE Prop.

  4 Beach Rd, Old Saybrook, CT 06475
• 

  $1,036,000

  Sold May 21, 2026

  4 Fenwood Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Above List Price
  • $529/SF
  • 27 Days On Market

  Current Estimated Value $1,039,143

  Last Listing Agent Jennifer Gurnell William Raveis Real Estate

  4 Fenwood Ln, Old Saybrook, CT 06475
• 

  Est $691,017

  Not Listed For Sale

  3 Lookout Hill Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,881 Sq Ft
  • Built 1991

  3 Lookout Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Coleen Brakenwagen Real Broker CT, LLC
• 

  

  /40

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,643 Sq Ft

  32 King St, Old Saybrook, CT 06475

  You are walking distance to shopping, restaurants and public transportation from this in-town cape with 4 bedrooms, 2 full baths, hardwood floors, oversized two car garage and an amazingly private backyard and large deck. Oil heat and a full dry basement complement this nicely proportioned 1643 square foot home. Town Beach and Long Island Sound are only a short drive away.

  Cherie Suhie J.M. REALTY

  32 King St, Old Saybrook, CT 06475
• 

  $375,000

  Sold Sep 05, 2025

  49 Hartford Ave, Old Saybrook, CT 06475

  • 1 Bed
  • 1 Bath
  • 504 Sq Ft
  • Built 1950

  Last Sold Summary

  • 25% Below List Price
  • $744/SF
  • 41 Days On Market

  Current Estimated Value $419,692

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  49 Hartford Ave, Old Saybrook, CT 06475
• 

  Not Listed For Sale

  23 Hill St, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Built 1930

  23 Hill St, Old Saybrook, CT 06475

  Last Sold Summary

  • 50 Days On Market

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

  

  /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
• 

  $3,750,000

  Sold Aug 10, 2026

  41 Watrous Point Rd, Old Saybrook, CT 06475

  • 6 Beds
  • 4.5 Baths
  • 5,536 Sq Ft
  • Built 1958

  Last Sold Summary

  • 6% Below List Price
  • $677/SF
  • 125 Days On Market

  Current Estimated Value $3,826,147

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

  41 Watrous Point Rd, Old Saybrook, CT 06475
• 

  Est $623,291

  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
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  /7

  $495,000

  • Land
  • 32.66 Acres
  • $15,156 per Acre

  0 Middlesex Turnpike, Old Saybrook, CT 06475

  32.66 ac at a prime intersection in Old Saybrook right off I-95. W/ Plans for various layouts of multiple building to totaling as much as 50,000 sqft +/-. B4 Zone offers a wide variety of uses. A large portion of this parcel is wetlands.

  Craig Milton Re/Max Valley Shore

  0 Middlesex Turnpike, Old Saybrook, CT 06475
• 

  $925,000

  Sold Sep 22, 2025

  45 Farview Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,791 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Above List Price
  • $331/SF
  • 11 Days On Market

  Current Estimated Value $976,439

  Last Listing Agent Amy Rubin William Raveis Real Estate

  45 Farview Ave, Old Saybrook, CT 06475
• 

  Est $558,141

  Not Listed For Sale

  15 Farview Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1948

  15 Farview Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Sang Jee Eagle Eye Realty PLLC

Showing Results 161 - 200, Page 5 of 18