Old Saybrook, CT Homes

• 

  Est $630,526 Not Listed For Sale

  44 Middletown Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,352 Sq Ft
  • Built 1958

  44 Middletown Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 13% Above List Price
  • $414/SF
  • 156 Days On Market

  • Last Sold Price $560,000
  • Jun 06, 2023

  Last Listing Agent Steven Koleno Beycome of Connecticut
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  /34

  $504,900

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  14 Denmore Ln, Old Saybrook, CT 06475

  This beautifully renovated ranch style home provides a perfect blend of modern style, comfort and luxury. As you enter you will be greeted by beautiful hardwood flooring creating a seamless flow from room to room elevating each space with enduring charm, comfort, and sophistication. This home boasts three spacious bedrooms and one full bathroom featuring sleek and modern finishes. The

  Terence Dominick Exceptional Real Estate LLC

  14 Denmore Ln, Old Saybrook, CT 06475
• 

  $358,000 Sold Nov 10, 2025

  Unlisted Address

  • 1 Bed
  • 1 Bath
  • 1,111 Sq Ft
  • Built 1800

  Last Sold Summary

  • 6% Above List Price
  • $322/SF
  • 2 Days On Market

  Current Estimated Value $376,273

  Last Listing Agent Jeanette Baigert Berkshire Hathaway NE Prop.

  Unlisted Address
• 

  Est $548,733 Not Listed For Sale

  235 Hidden Cove Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1978

  235 Hidden Cove Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 5% Below List Price
  • $417/SF
  • 0 Days On Market

  • Last Sold Price $575,000
  • Dec 13, 2024

  Last Listing Agent Brian Jermainne Team Jermainne Real Estate Services, LLC
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  /25

  $419,900

  • 4 Beds
  • 1 Bath
  • 640 Sq Ft

  39 Middletown Ave, Old Saybrook, CT 06475

  Charming and beautifully updated 4 bedroom Seasonal Cottage in desireable Saybrook Manor beach community. This home offers the perfect blend of character and modern improvements with vaulted ceilings and exposed beams. The completely remodeled kitchen features Corian countertops, a classic farmhouse sink, skylight for natural light and matching rolling kitchen cart for added prep and storage

  Tracy Pentalow Property Shoppe, LLC

  39 Middletown Ave, Old Saybrook, CT 06475
• 

  $850,000 Sold Sep 08, 2025

  122 College St, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 3,200 Sq Ft
  • Built 1890

  Last Sold Summary

  • 29% Below List Price
  • $266/SF
  • 77 Days On Market

  Current Estimated Value $917,681

  Last Listing Agent Mary McDonald Coldwell Banker Realty

  122 College St, Old Saybrook, CT 06475
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  Est $1,060,979 Not Listed For Sale

  8 Maynard Cir, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 3,178 Sq Ft
  • Built 2008

  8 Maynard Cir, Old Saybrook, CT 06475

  Last Sold Summary

  • 21% Above List Price
  • $275/SF
  • 66 Days On Market

  • Last Sold Price $875,000
  • Aug 29, 2024

  Last Listing Agent Craig Milton RE/MAX
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  /28

  $799,900 Pending

  • 2 Beds
  • 2 Baths
  • 944 Sq Ft

  129 Nehantic Trail, Old Saybrook, CT 06475

  MOVE-IN READY! Remodeled story book Cape Cod in the desirable Indian Town beach community with marsh and ocean views! This designer remodeled year round beach home is anything but average. Fall in love with the gorgeous new kitchen with GE Cafe appliances, stunning Taj Mahal Quartzite counters, and large island. Relax in the impressive great room with vaulted ceilings, substantial exposed

  Lynn Toper CR Premier Properties

  129 Nehantic Trail, Old Saybrook, CT 06475
• 

  $860,000 Sold Jan 15, 2026

  1 Lighthouse Ln, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 3,286 Sq Ft
  • Built 1987

  Last Sold Summary

  • 25% Below List Price
  • $262/SF
  • 214 Days On Market

  Current Estimated Value $890,539

  Last Listing Agent Lynne Ferrigno Coldwell Banker Realty

  1 Lighthouse Ln, Old Saybrook, CT 06475
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  Est $461,329 Not Listed For Sale

  7 North St, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1950

  7 North St, Old Saybrook, CT 06475

  Last Sold Summary

  • 19% Above List Price
  • $449/SF
  • 26 Days On Market

  • Last Sold Price $387,900
  • Feb 01, 2024

  Last Listing Agent Lisa Genovali RE/MAX
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  /39

  $675,000

  • 3 Beds
  • 1.5 Baths
  • 1,033 Sq Ft

  14 Cedarwood Ln, Old Saybrook, CT 06475

  Welcome to your new shoreline home - a charming ranch-style retreat nestled in the heart of Old Saybrook. This beautifully maintained 3-bedroom, 1 1/2-bathroom home offers a perfect blend of comfortable living and coastal New England lifestyle - all just approx. 1 mile from the private Cornfield Point beach. Step inside to discover a bright, open-concept floor plan that flows from the living area

  Chelsea Daley Real Broker CT, LLC

  14 Cedarwood Ln, Old Saybrook, CT 06475
• 

  $620,000 Sold Sep 30, 2025

  1 Hartford Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,762 Sq Ft
  • Built 1940

  Last Sold Summary

  • 11% Below List Price
  • $352/SF
  • 45 Days On Market

  Current Estimated Value $676,368

  Last Listing Agent Bryan Neurath Country Manor Realty

  1 Hartford Ave, Old Saybrook, CT 06475
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  Est $569,650 Not Listed For Sale

  20 Whitney Ave, Old Saybrook, CT 06475

  • 1 Bed
  • 1 Bath
  • 1,107 Sq Ft
  • Built 1946

  20 Whitney Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 23% Above List Price
  • $420/SF
  • 37 Days On Market

  • Last Sold Price $465,000
  • Dec 01, 2023

  Last Listing Agent Joanne Breen ERA Hart Sargis-Breen
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  /39

  $750,000 Under Contract

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

  100 Dudley Ave Unit F31, Old Saybrook, CT 06475

  Enjoy effortless shoreline living with sweeping views of North Cove from this beautifully renovated, move-in ready townhouse-style condo in the heart of Old Saybrook. Perfect as a second home or easy downsize, this light-filled residence offers an open layout designed to capture the water from the updated kitchen open to the dining and living areas taking in the water views. The spacious

  Joel Lucas Coldwell Banker Realty

  100 Dudley Ave Unit F31, Old Saybrook, CT 06475
• 

  $749,000 Sold Aug 01, 2025

  509 Main St Unit 6, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 2011

  Last Sold Summary

  • $436/SF
  • 47 Days On Market

  Current Estimated Value $750,899

  Last Listing Agent Jake Pulcini Chiarito Real Estate LLC

  509 Main St Unit 6, Old Saybrook, CT 06475
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  Est $1,285,479 Not Listed For Sale

  11 Beechwood Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft
  • Built 1953

  11 Beechwood Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 9% Above List Price
  • $480/SF
  • 68 Days On Market

  • Last Sold Price $1,175,000
  • Dec 29, 2023

  Last Listing Agent Debbie Huscher Real Broker CT, LLC
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  /29

  $508,000

  • 2 Beds
  • 1.5 Baths
  • 1,557 Sq Ft

  118 Sandy Point Rd, Old Saybrook, CT 06475

  Summerwood on the Sound. Step into this stunning townhouse condominium featuring a fabulous kitchen with spacious quartz counters and breakfast bar, custom designed cabinetry and stainless steel appliances. The open concept living room and dining area boast beautiful wood flooring, elegant crown molding and glass doors to the private deck area, perfect for relaxing and entertaining. There is also

  Carla Mousch William Raveis Real Estate

  118 Sandy Point Rd, Old Saybrook, CT 06475
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  $570,000 Sold Feb 11, 2026

  175 Ferry Rd Unit 10, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,711 Sq Ft
  • Built 2005

  Last Sold Summary

  • $333/SF
  • 26 Days On Market

  Current Estimated Value $570,267

  Last Listing Agent Claire Kilmer Coldwell Banker Realty

  175 Ferry Rd Unit 10, Old Saybrook, CT 06475
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  Est $580,610 Not Listed For Sale

  175 Ferry Rd Unit 8, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,799 Sq Ft
  • Built 2006

  175 Ferry Rd Unit 8, Old Saybrook, CT 06475

  Last Sold Summary

  • 11% Above List Price
  • $291/SF
  • 114 Days On Market

  • Last Sold Price $523,000
  • Aug 31, 2023

  Last Listing Agent Charene Clark Coldwell Banker Realty
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  /40

  $1,695,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,978 Sq Ft

  43 Indianola Dr, Old Saybrook, CT 06475

  Enjoy coastal living at its finest in the coveted Cornfield Point community. This custom-built home offers nearly 3,000 square feet of thoughtfully designed space, featuring 4 bedrooms, 3 full baths, and a versatile main-level office, den, or media room to suit your lifestyle. Step outside to a spacious deck where you can take in serene marsh and water views of Cornfield Point Beach, with a

  Marc Delise Coldwell Banker Realty

  43 Indianola Dr, Old Saybrook, CT 06475
• 

  $725,000 Sold May 12, 2025

  8 Acorn Dr, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,448 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Above List Price
  • $296/SF
  • 17 Days On Market

  Current Estimated Value $754,694

  Last Listing Agent Craig Milton Re/Max Valley Shore

  8 Acorn Dr, Old Saybrook, CT 06475
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  Est $1,428,400 Not Listed For Sale

  9 Watrous Point Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 4 Baths
  • 3,952 Sq Ft
  • Built 1997

  9 Watrous Point Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 30% Above List Price
  • $278/SF
  • 76 Days On Market

  • Last Sold Price $1,100,000
  • Jul 25, 2024

  Last Listing Agent Tina Rupp William Pitt
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  /39

  $425,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  5 Sunrise Ave, Old Saybrook, CT 06475

  Welcome to this well-maintained rambler ranch offering comfortable one-level living in beautiful Old Saybrook. This home features 3 spacious bedrooms and 1.5 bathrooms with central air, perfect for everyday living or hosting guests. Inside, you'll find beautiful hardwood floors that add warmth and character throughout much of the home. The layout includes a dedicated laundry room for added

  Terry McDonald McDonald Real Estate, LLC

  5 Sunrise Ave, Old Saybrook, CT 06475
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  $350,000 Sold Feb 24, 2026

  195 Bokum Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft
  • Built 1799

  Last Sold Summary

  • 12% Below List Price
  • $150/SF
  • 32 Days On Market

  Current Estimated Value $367,412

  Last Listing Agent Dotty Owens Sunset Creek Realty, LLC

  195 Bokum Rd, Old Saybrook, CT 06475
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  Est $630,291 Not Listed For Sale

  1 Dwayne Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • Built 1973

  1 Dwayne Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 36% Above List Price
  • $212/SF
  • 20 Days On Market

  • Last Sold Price $465,000
  • Mar 12, 2024

  Last Listing Agent Sang Jee Eagle Eye Realty PLLC
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  /37

  $725,000 Under Contract

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

  100 Dudley Ave Unit F27, Old Saybrook, CT 06475

  Enjoy effortless shoreline living with sweeping views of North Cove from this beautifully renovated, move-in ready townhouse-style condo in the heart of Old Saybrook. Perfect as a second home or easy downsize, this light-filled residence offers an open layout designed to capture the water. A desirable end-unit, this spacious two-bedroom design includes a stunning primary suite with its own full

  Joel Lucas Coldwell Banker Realty

  100 Dudley Ave Unit F27, Old Saybrook, CT 06475
• 

  $500,000 Sold May 08, 2026

  9 2nd Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1959

  Last Sold Summary

  • 9% Above List Price
  • $481/SF
  • 2 Days On Market

  Current Estimated Value $448,789

  Last Listing Agent Sally Tucker Coldwell Banker Realty

  9 2nd Ave, Old Saybrook, CT 06475
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  Est $786,045 Not Listed For Sale

  32 Cricket Ct, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 1,911 Sq Ft
  • Built 1976

  32 Cricket Ct, Old Saybrook, CT 06475

  Last Sold Summary

  • 22% Above List Price
  • $337/SF
  • 48 Days On Market

  • Last Sold Price $644,000
  • Nov 08, 2023

  Last Listing Agent Sharon Linder Berkshire Hathaway Home Services
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  /10

  $159,900 Under Contract

  • Land
  • 6,969 Sq Ft
  • $999,375 per Acre

  6 South St, Old Saybrook, CT 06475

  Highest & Best by 3pm on 4/28! Move into your dream home by autumn! This exceptional lot is truly shovel-ready, and includes full plans for a beautifully designed 3-bedroom home with water views. All essential approvals and documentation are in place, including septic plans and B100, along with fully transferable building permits-saving you time and effort! Prefer your own design? You can easily

  Katie Schubert KW Legacy Partners

  6 South St, Old Saybrook, CT 06475
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  $585,000 Sold Mar 13, 2026

  175 Ferry Rd Unit 4, Old Saybrook, CT 06475

  • 2 Beds
  • 2.5 Baths
  • 1,852 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $316/SF
  • 16 Days On Market

  Current Estimated Value $597,029

  Last Listing Agent Gigi Giordano Taylor Compass Connecticut, LLC

  175 Ferry Rd Unit 4, Old Saybrook, CT 06475
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  Est $656,338 Not Listed For Sale

  6 Willard St, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,796 Sq Ft
  • Built 1973

  6 Willard St, Old Saybrook, CT 06475

  Last Sold Summary

  • 25% Above List Price
  • $292/SF
  • 2 Days On Market

  • Last Sold Price $525,000
  • Oct 16, 2023

  Last Listing Agent Pardi & Zucco Team William Pitt
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  /38

  $849,900

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

  1 Beamon Meadow Place, Old Saybrook, CT 06475

  Coastal colonial with deeded beach rights to Cornfield Point, set on 1.44 private acres overlooking a scenic tidal marsh in Old Saybrook. This 3-bedroom, 3-bath home offers water views, hardwood floors throughout, and a flexible layout ideal for year-round living or a weekend retreat. A front-to-back living room with fireplace provides a spacious gathering area, while the formal dining room

  Linda Toscano Coldwell Banker Realty

  1 Beamon Meadow Place, Old Saybrook, CT 06475
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  $893,500 Sold Dec 05, 2025

  55 Cypress Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $466/SF
  • 21 Days On Market

  Current Estimated Value $913,839

  Last Listing Agent Tammy Tinnerello William Pitt Sotheby's Int'l

  55 Cypress Rd, Old Saybrook, CT 06475
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  Est $617,394 Not Listed For Sale

  24 Middletown Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1967

  24 Middletown Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 4% Below List Price
  • $630/SF
  • 6 Days On Market

  • Last Sold Price $640,000
  • Oct 30, 2024

  Last Listing Agent Carla Corrigan eXp Realty
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  /30

  $2,195,000 Under Contract

  • 1 Bed
  • 1.5 Baths
  • 7,985 Sq Ft

  125 Main St, Old Saybrook, CT 06475

  Great mixed-use opportunity. Fully leased office building with town-approved one-bedroom apartment on Second Floor with kitchen, full bath including washer/dryer. Great opportunity to own a mixed-use property on beautiful Main Street in Old Saybrook. Established salon with long term lease on first floor. The one bedroom apartment on the second floor has been carpeted and painted and has separate

  Gary Marino William Raveis Real Estate

  125 Main St, Old Saybrook, CT 06475
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  $520,000 Sold Jul 07, 2025

  25 Chalker Beach Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 922 Sq Ft
  • Built 1986

  Last Sold Summary

  • 10% Below List Price
  • $564/SF
  • 122 Days On Market

  Current Estimated Value $510,796

  Last Listing Agent Susan Malton Coldwell Banker Realty

  25 Chalker Beach Rd, Old Saybrook, CT 06475
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  Est $514,113 Not Listed For Sale

  10 Cliff Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft
  • Built 1992

  10 Cliff Dr, Old Saybrook, CT 06475

  Last Sold Summary

  • 33% Above List Price
  • $248/SF
  • 5 Days On Market

  • Last Sold Price $386,000
  • Dec 21, 2023

  Last Listing Agent Lewis Jump III RE/MAX
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  /38

  $1,700,000

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  104 Knollwood Dr, Old Saybrook, CT 06475

  Knollwood Beach waterfront on South Cove with amazing views! Nestled on the waterfront in the highly sought-after South Cove, this Knollwood Beach property offers sweeping panoramic views from every room. Privately set on a generous 0.37-acre lot, this 3-bedroom home provides direct water access-perfect for kayaking out to Long Island Sound right from your backyard. Inside, the home blends charm

  Karen Lee Coldwell Banker Realty

  104 Knollwood Dr, Old Saybrook, CT 06475
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  $539,000 Sold Aug 27, 2025

  18 Lynde St, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,185 Sq Ft
  • Built 1947

  Last Sold Summary

  • 2% Below List Price
  • $455/SF
  • 43 Days On Market

  Current Estimated Value $549,617

  Last Listing Agent Liz Squillacote William Pitt Sotheby's Int'l

  18 Lynde St, Old Saybrook, CT 06475
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  Est $672,393 Not Listed For Sale

  21 Nehantic Trail, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1952

  21 Nehantic Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 2% Below List Price
  • $538/SF
  • 26 Days On Market

  • Last Sold Price $685,000
  • Jun 28, 2024

  Last Listing Agent Teri Lewis William Pitt

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