Old Saybrook, CT Homes

• 

  $400,000

  Sold Jun 12, 2026

  5 Sunrise Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Below List Price
  • $376/SF
  • 92 Days On Market

  Current Estimated Value $412,166

  Last Listing Agent Terry McDonald McDonald Real Estate, LLC

  5 Sunrise Ave, Old Saybrook, CT 06475
• 

  Est $736,648

  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.
• 

  

  

  /40

  $999,000

  Open Sat 11AM - 1PM $101K PRICE DROP Under Contract

  • 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
• 

  $725,000

  Sold Jun 30, 2026

  100 Dudley Ave Unit F27, Old Saybrook, CT 06475

  • 2 Beds
  • 2.5 Baths
  • 2,310 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $314/SF
  • 74 Days On Market

  Current Estimated Value $729,087

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  100 Dudley Ave Unit F27, 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
• 

  

  /38

  $799,999

  $99K PRICE DROP

  • 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
• 

  $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
• 

  Est $645,737

  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
• 

  

  /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
• 

  $722,500

  Sold Dec 05, 2025

  5 Fox Hollow Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3 Baths
  • 2,142 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $337/SF
  • 63 Days On Market

  Current Estimated Value $769,130

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  5 Fox Hollow Rd, Old Saybrook, CT 06475
• 

  Est $2,185,715

  Not Listed For Sale

  49 Cromwell Place, Old Saybrook, CT 06475

  • 3 Beds
  • 4 Baths
  • 3,965 Sq Ft
  • Built 1990

  49 Cromwell Place, Old Saybrook, CT 06475

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Tina Rupp William Pitt Sotheby's Int'l
• 

  

  /40

  $699,900

  Pending

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft

  18 Shepard St, Old Saybrook, CT 06475

  Enjoy the best of Old Saybrook from this spacious 3-bedroom, 2-bath Cape offering over 2,100 square feet of living space in a residential setting close to downtown and the shoreline. Just beyond Main Street and The Kate, with convenient access to Saybrook Point, restaurants, shopping, the train station and area amenities. Inside, an expansive living and family room offers hardwood floors, a brick

  Tony Walstra William Pitt Sotheby's Int'l

  18 Shepard St, 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 $677,100

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  14 Watrous Point Rd, Old Saybrook, CT 06475
• 

  Est $775,898

  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.
• 

  

  /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
• 

  $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 $791,396

  Last Listing Agent Chloe White KW Legacy Partners

  117 Ayers Point Rd, Old Saybrook, CT 06475
• 

  Est $652,459

  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
• 

  

  /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
• 

  $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 $693,995

  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

  $750,000

  $47K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,565 Sq Ft

  100 Dudley Ave Unit F30, Old Saybrook, CT 06475

  Spectacular North Cove unobstructed water views and downtown village living come together in this beautifully renovated townhouse-style condo, offering an exceptional opportunity for shoreline buyers seeking a turn-key home under $1 million. Enjoy captivating water views and wildlife from the open kitchen, dining and living areas, with a stylish renovated kitchen featuring a breakfast bar and

  Joel Lucas Coldwell Banker Realty

  100 Dudley Ave Unit F30, 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 $163,178

  Last Listing Agent Katie Schubert KW Legacy Partners

  6 South St, 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
• 

  

  /39

  $749,900

  $149K PRICE DROP Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,544 Sq Ft

  9 Barley Hill Rd, Old Saybrook, CT 06475

  This beautifully maintained home offers the perfect blend of luxury and comfort! The main level offers exceptional versatility with an open floor plan, hardwood floors, a luxurious primary bedroom suite, along with a living room, family room, gourmet kitchen and formal dining room designed for both relaxed living and elegant gatherings. The first floor primary bedroom suite features California

  Sharon Linder Berkshire Hathaway NE Prop.

  9 Barley Hill 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 $858,415

  Last Listing Agent Linda Toscano Coldwell Banker Realty

  1 Beamon Meadow Place, 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
• 

  

  /6

  $695,000

  $300K PRICE DROP

  • Land
  • 1.16 Acres
  • $599,138 per Acre

  1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475

  1.25 Acres in B4 Zone. Public water available, septic required. Traffic count 15,900.

  Maxwell Lyman Lyman Real Estate

  1333 Boston Post Rd Unit 1, 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 $705,223

  Last Listing Agent George Agnelli Agnelli Real Estate

  12 Bellaire Dr, Old Saybrook, CT 06475
• 

  Est $572,326

  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
• 

  

  /40

  $1,225,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 884 Sq Ft

  24 W Shore Dr, Old Saybrook, CT 06475

  Your Year-Round Beach Home Awaits in Cornfield Point Welcome to your opportunity to own a year-round home in Cornfield Point, one of Connecticut's most desirable beach communities. Ideally located just steps from the beach. This move-in-ready home offers the perfect combination of comfort, coastal living, and breathtaking water views. The home features 3 bedrooms and 1 full bath, along with a

  David Rodriguez William Pitt Sotheby's Int'l

  24 W Shore Dr, 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 $842,835

  Last Listing Agent Dylan Walter William Raveis Real Estate

  11 S View Terrace, Old Saybrook, CT 06475
• 

  Est $1,015,656

  Not Listed For Sale

  4 Willow Brook Farm Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 4,132 Sq Ft
  • Built 1998

  4 Willow Brook Farm Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Jan Murray J.M. REALTY
• 

  

  /40

  $899,000

  $76K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,569 Sq Ft

  18 Old South Cove Rd, Old Saybrook, CT 06475

  Whether your vision is to Move-in, Renovate, or Custom Build from the ground up, this water-view coastal property is for you! Currently home to a classic 1,569 sq. ft. coastal ranch built on an oversized .42-acre water-view parcel, the true value of this premier Residential District A property lies in its exceptional dimensions, rare zoning advantages, and all the possibilities that come with the

  Steven Koleno Beycome of Connecticut

  18 Old South Cove 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 $503,615

  Last Listing Agent Tim O'Hara William Raveis Real Estate

  258 School House Rd, Old Saybrook, CT 06475
• 

  Est $732,434

  Not Listed For Sale

  64 Atlantic Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1960

  64 Atlantic Dr, Old Saybrook, CT 06475

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Joel Lucas Coldwell Banker Realty
• 

  

  /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
• 

  $849,000

  Sold Sep 15, 2026

  17 Barnes Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1977

  Last Sold Summary

  • 13% Above List Price
  • $884/SF
  • 25 Days On Market

  Current Estimated Value $941,779

  Last Listing Agent Lynn Lehrman Re/Max Valley Shore

  17 Barnes Rd, Old Saybrook, CT 06475
• 

  Est $429,101

  Not Listed For Sale

  49 Hartford Ave, Old Saybrook, CT 06475

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

  49 Hartford Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.
• 

  

  /40

  $749,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,205 Sq Ft

  6 Nutmeg Cir, Old Saybrook, CT 06475

  This meticulously maintained hidden gem features an inviting open floor plan with a dramatic double-sided fireplace creating warmth and character between the main living areas. The living room is enhanced by beautiful built-ins and a charming reading nook, while the spacious kitchen features an expansive island, built in china cabinets with plenty of room for family gatherings, casual dining and

  Sharon Linder Berkshire Hathaway NE Prop.

  6 Nutmeg Cir, 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 $1,043,498

  Last Listing Agent Jennifer Gurnell William Raveis Real Estate

  4 Fenwood Ln, Old Saybrook, CT 06475

Showing Results 161 - 200, Page 5 of 18