Old Saybrook, CT Homes

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  $859,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft

  33 Fenwood Rd, Old Saybrook, CT 06475

  Fenwood Beach Association! This beautifully renovated home is ready for you to move right in to this newly updated home. The light-filled interior offers an open flow between the kitchen, dining, and living areas, perfect for relaxed coastal living. The primary suite features a gorgeous new full bath, while the finished lower level adds 700 sq ft of flexible space currently used as a family room

  Joel Lucas Coldwell Banker Realty

  33 Fenwood Rd, Old Saybrook, CT 06475
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  /23

  $3,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,137 Sq Ft
  • House for Rent

  8 Clinton Ave, Old Saybrook, CT 06475

  Turn-key Academic Shoreline Rental for today's modern-living and tastefully decorated in Old Saybrook, CT. Beautifully renovated home in South Cove neighborhood great for morning walks with coffee or evening strolls with a cocktail in hand. This lovely light filled home has an open floor plan, custom built kitchen with modern stainless steel appliances, new hardwood floors throughout, first floor

  Terry McDonald McDonald Real Estate, LLC

  8 Clinton Ave, Old Saybrook, CT 06475
• 

  $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 $880,345

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

  41 Meadowood Ln, Old Saybrook, CT 06475
• 

  Est $2,487,691 Not Listed For Sale

  468 Main St, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 4,225 Sq Ft
  • Built 1995

  468 Main St, Old Saybrook, CT 06475

  Last Sold Summary

  • 16% Below List Price
  • $698/SF
  • 13 Days On Market

  Last Sold Price $2,950,000

  Last Listing Agent Teri Lewis William Pitt
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  /40

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 4,109 Sq Ft

  96 Ayers Point Rd, Old Saybrook, CT 06475

  Discover the serenity of Ayers Point in this spacious 3400 sq ft home with captivating views of the Connecticut River and surrounding marshland. Privately set with a beautiful inground pool and lush gardens, this retreat is perfect for those seeking a coastal lifestyle near boating and village charm. The home features both main and upper level primary suites, offering flexibility and comfort for

  Joel Lucas Coldwell Banker Realty

  96 Ayers Point Rd, Old Saybrook, CT 06475
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  /19

  $2,400 total monthly price

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

  38 Seabreeze Rd, Old Saybrook, CT 06475

  This spectacular home with a fantastic location is an Academic Rental; from September 15, 2026 through May 15, 2027. 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

  Terry McDonald McDonald Real Estate, LLC

  38 Seabreeze Rd, Old Saybrook, CT 06475
• 

  $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

  Current Estimated Value $720,980

  Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

  355 Main St, Old Saybrook, CT 06475
• 

  Est $621,790 Not Listed For Sale

  21 Baum Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 1.5 Baths
  • 1,290 Sq Ft
  • Built 1959

  21 Baum Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 25% Above List Price
  • $387/SF
  • 3 Days On Market

  Last Sold Price $499,000

  Last Listing Agent Maria Szewczyk Gorski Realty LLC
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  /2

  $985,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  24 Cottage Place, Old Saybrook, CT 06475

  Experience the perfect blend of timeless character and contemporary convenience in this stunning colonial. The residence welcomes you with an open-concept floor plan and an expertly updated chef's kitchen, featuring premium Sub-Zero refrigeration for an upscale culinary experience. Designed for both relaxation and entertaining, the home offers four bedrooms and three full baths, including a cozy

  Jacqueline Stevens William Pitt Sotheby's Int'l

  24 Cottage Place, Old Saybrook, CT 06475
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  /15

  $8,400 total monthly price

  • 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 $8400 weekly rental or 1200 a day for June 1st thru Sept. 15th or weekly at $8400. 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.

  Joel Lucas Coldwell Banker Realty

  25 W Shore Dr, Old Saybrook, CT 06475
• 

  $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

  Current Estimated Value $1,169,082

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  25 Maplewood Rd, Old Saybrook, CT 06475
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  Est $667,223 Not Listed For Sale

  8 East St, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,170 Sq Ft
  • Built 1963

  8 East St, Old Saybrook, CT 06475

  Last Sold Summary

  • 33% Above List Price
  • $230/SF
  • 78 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC
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  /23

  $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

  60 Ingham Hill Rd, Old Saybrook, CT 06475
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  /22

  $4,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • House for Rent

  28 Beach Rd W, Old Saybrook, CT 06475

  Amazing views of Long Island Sound at 28 Beach Rd West, Old Saybrook! Beautiful Academic Rental "beach" home, with 3 bedrooms and 2 baths, available for your enjoyment, across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

  Terry McDonald McDonald Real Estate, LLC

  28 Beach Rd W, Old Saybrook, CT 06475
• 

  $650,000 Sold May 15, 2025

  37 Fenwood Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Built 1953

  Last Sold Summary

  • 6% Below List Price
  • $516/SF
  • 33 Days On Market

  Current Estimated Value $668,261

  Last Listing Agent Charles Conti Coldwell Banker Realty

  37 Fenwood Rd, Old Saybrook, CT 06475
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  Est $619,760 Not Listed For Sale

  18 Pheasant Hill Ln, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,288 Sq Ft
  • Built 1970

  18 Pheasant Hill Ln, Old Saybrook, CT 06475

  Last Sold Summary

  • 12% Above List Price
  • $241/SF
  • 45 Days On Market

  Last Sold Price $551,000

  Last Listing Agent Dawn D'Auria Coldwell Banker
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  /25

  $450,000

  • 4 Beds
  • 1 Bath
  • 640 Sq Ft

  39 Middletown Ave, Old Saybrook, CT 06475

  Charming and beautifully updated 4 bedroom 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 space. The

  Tracy Pentalow Property Shoppe, LLC

  39 Middletown Ave, Old Saybrook, CT 06475
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  $870,000 Sold Nov 20, 2025

  7 Sharon Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1978

  Last Sold Summary

  • 13% Below List Price
  • $330/SF
  • 129 Days On Market

  Current Estimated Value $879,216

  Last Listing Agent Jessica Blancato William Pitt Sotheby's Int'l

  7 Sharon Ln, Old Saybrook, CT 06475
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  Est $680,488 Not Listed For Sale

  28 Attawanhood Trail, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft
  • Built 1953

  28 Attawanhood Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 5% Above List Price
  • $555/SF
  • 12 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Craig Hebert RE/MAX
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  /34

  $519,900

  • 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
• 

  $800,000 Sold Jul 29, 2025

  92 Fenwood Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Above List Price
  • $442/SF
  • 2 Days On Market

  Current Estimated Value $817,044

  Last Listing Agent Fran Manganello Coldwell Banker Realty

  92 Fenwood Dr, Old Saybrook, CT 06475
• 

  Est $118,428 Not Listed For Sale

  22 Ragged Rock Rd, Old Saybrook, CT 06475

  22 Ragged Rock Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 49% Above List Price
  • 183 Days On Market

  Last Sold Price $79,500

  Last Listing Agent Al Chiarito Chiarito Real Estate LLC
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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
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  $742,900 Sold Oct 31, 2025

  16 Howard St, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Below List Price
  • $529/SF
  • 3 Days On Market

  Current Estimated Value $738,324

  Last Listing Agent Terry Kemper Coldwell Banker Realty

  16 Howard St, Old Saybrook, CT 06475
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  Est $1,006,289 Not Listed For Sale

  11 Fenwood Ave, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,178 Sq Ft
  • Built 1963

  11 Fenwood Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 6% Above List Price
  • $436/SF
  • 17 Days On Market

  Last Sold Price $949,500

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  /29

  $519,000

  • 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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  $775,000 Sold Aug 05, 2025

  16, 18 Bayberry Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1958

  Last Sold Summary

  • 9% Below List Price
  • $1,009/SF
  • 97 Days On Market

  Last Listing Agent Cherie Suhie J.M. REALTY

  16, 18 Bayberry Rd, Old Saybrook, CT 06475
• 

  Est $1,126,687 Not Listed For Sale

  10 Turnstone Rd, Essex, CT 06426

  • 4 Beds
  • 2.5 Baths
  • 3,048 Sq Ft
  • Built 2005

  10 Turnstone Rd, Essex, CT 06426

  Last Sold Summary

  • 25% Above List Price
  • $295/SF
  • 33 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Rose McWaid William Raveis Real Estate
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  /36

  $459,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  9 2nd Ave, Old Saybrook, CT 06475

  Experience the charm of picturesque Old Saybrook & enjoy all that shoreline living has to offer incl. beaches, boating, fine dining, theater & Main Street shopping.This well-maintained ranch-style home offers comfortable one-level living on a quiet dead-end street, conveniently located just minutes to downtown, Routes 9, I- 95, marinas & a public boat launch. The home is nicely landscaped &

  Sally Tucker Coldwell Banker Realty

  9 2nd Ave, Old Saybrook, CT 06475
• 

  $620,000 Sold Jul 31, 2025

  37 Woodland Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 22% Below List Price
  • $413/SF
  • 94 Days On Market

  Current Estimated Value $664,518

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  37 Woodland Dr, Old Saybrook, CT 06475
• 

  Est $429,224 Not Listed For Sale

  15 Cranton Ave, Old Saybrook, CT 06475

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft
  • Built 1938

  15 Cranton Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 23% Above List Price
  • $572/SF
  • 48 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Matt Diamond Houlihan Lawrence WD
• 

  

  /38

  $449,999

  • 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
• 

  $575,000 Sold May 15, 2025

  227 Hidden Cove Rd Unit 227, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,898 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $303/SF
  • 57 Days On Market

  Current Estimated Value $584,025

  Last Listing Agent Carla Mousch William Raveis Real Estate

  227 Hidden Cove Rd Unit 227, Old Saybrook, CT 06475
• 

  Est $513,867 Not Listed For Sale

  136 Sandy Point Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 1.5 Baths
  • 1,288 Sq Ft
  • Built 1977

  136 Sandy Point Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 4% Above List Price
  • $382/SF
  • 34 Days On Market

  Last Sold Price $492,500

  Last Listing Agent Lisa Genovali RE/MAX
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  $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
• 

  $890,999 Sold Apr 24, 2025

  49 Atlantic Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Above List Price
  • $543/SF
  • 0 Days On Market

  Current Estimated Value $938,480

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  49 Atlantic Dr, Old Saybrook, CT 06475
• 

  Est $650,725 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

  • 16% Above List Price
  • $414/SF
  • 156 Days On Market

  Last Sold Price $560,000

  Last Listing Agent Steven Koleno Beycome of Connecticut
• 

  

  /22

  $799,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  21 Fenwick St, Old Saybrook, CT 06475

  This home is being sold "AS IS".Right place at the right time! This home now wants a new owner. Renovations are needed but location, location, location.Water views with walking ability to Saybrook Point and Fenwick golf course. Ranch with 3 beds and 2 baths. This is an opportunity to enjoy and experience Old Saybrook at its best. The beautiful views from inside the home is an ever-changing

  Paula Stuart Berkshire Hathaway NE Prop.

  21 Fenwick St, Old Saybrook, CT 06475
• 

  $840,000 Sold Jan 30, 2026

  26 College St, Old Saybrook, CT 06475

  • 5 Beds
  • 3 Baths
  • 2,898 Sq Ft
  • Built 1929

  Last Sold Summary

  • 1% Below List Price
  • $290/SF
  • 52 Days On Market

  Current Estimated Value $854,404

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

  26 College St, Old Saybrook, CT 06475
• 

  Est $537,808 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

  • 6% Below List Price
  • $417/SF
  • 0 Days On Market

  Last Sold Price $575,000

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

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