Old Saybrook, CT Homes

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  $985,000 Under Contract

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

  4 Fenwood Ln, Old Saybrook, CT 06475

  Refined coastal retreat at 4 Fenwood Lane, in the Fenwood Beach Association of Old Saybrook, offering distant views of Long Island Sound and a seamless blend of luxury and shoreline living. This freshly painted, thoughtfully updated beach house is ideally located just one home from the main road, providing both convenience and a private setting. Enjoy deeded beach rights and a short walk to

  Jennifer Gurnell William Raveis Real Estate

  4 Fenwood Ln, Old Saybrook, CT 06475
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  /17

  $3,500 Per Month

  • 3 Beds
  • 2 Baths
  • 2,946 Sq Ft
  • House for Rent

  958 Middlesex Turnpike, Old Saybrook, CT 06475

  Annual Unfurnished Rental in a Prime Location Between Old Saybrook and Essex This spacious and versatile property offers 3 bedrooms and 2 full baths, with 1,826 square feet of main-level living plus an additional 1,120 square feet of finished lower level, complete with a full bath-ideal for extended living, recreation, or workspace. Zoned for both residential and commercial use, this property

  Lisa Fekete William Raveis Real Estate

  958 Middlesex Turnpike, Old Saybrook, CT 06475
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  $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 $663,344

  Last Listing Agent Charles Conti Coldwell Banker Realty

  37 Fenwood Rd, Old Saybrook, CT 06475
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  Est $794,764 Not Listed For Sale

  16 Fordham Trail, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,673 Sq Ft
  • Built 1992

  16 Fordham Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 18% Above List Price
  • $184/SF
  • 29 Days On Market

  • Last Sold Price $675,000
  • Aug 16, 2024

  Last Listing Agent WAYNE ARUTE Law Realty Group
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  /31

  $1,075,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 3,496 Sq Ft

  12 Hill Rd, Old Saybrook, CT 06475

  Welcome to Otter Cove Estates, located in Old Saybrook Ct. Live in the established area of residential homes that offer large lots of 2 acres at the mouth of the Ct River. This home offers 3 bedrooms with Master suite on the first floor with ensuite. Open floor plan large kitchen, built in newer appliances subzero built in fridge, Electrolux double ovens, Bosch dishwasher and newer microwave.

  Paula Stuart Berkshire Hathaway NE Prop.

  12 Hill Rd, Old Saybrook, CT 06475
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  $4,500 Per Month

  • 4 Beds
  • 1.5 Baths
  • 1,316 Sq Ft
  • House for Rent

  33 Beach Rd W, Old Saybrook, CT 06475

  Adorable 4-bedroom, 1-1/2 bath beachfront retreat available as an academic rental from early September through the end of May in the highly sought-after Chalker Beach neighborhood of Old Saybrook. Offered fully furnished with all utilities included, this charming coastal home that was completely rebuilt in 1986 is the perfect place to enjoy off-season shoreline living. Warm coastal wood paneling

  Katie Smith Berkshire Hathaway NE Prop.

  33 Beach Rd W, 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 $844,622

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

  7 Sharon Ln, Old Saybrook, CT 06475
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  Est $598,921 Not Listed For Sale

  1 Anchorage Ln, Old Saybrook, CT 06475

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft
  • Built 1955

  1 Anchorage Ln, Old Saybrook, CT 06475

  Last Sold Summary

  • 6% Above List Price
  • $307/SF
  • 140 Days On Market

  • Last Sold Price $565,000
  • Sep 13, 2024

  Last Listing Agent Renee McCammon Berkshire Hathaway Home Services
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  /40

  $899,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,170 Sq Ft

  129 Old Boston Post Rd, Old Saybrook, CT 06475

  Charm and convenience come together in this beautifully reconstructed farmhouse offering 2,200 sq ft of stylish, easy living. Designed for comfort and flexibility, the home features a sought-after first-floor primary suite, ideal for one-level living, along with two additional bedrooms for guests, family, or home office needs. Rich hardwood floors and a thoughtfully designed kitchen with high-end

  Joel Lucas Coldwell Banker Realty

  129 Old Boston Post Rd, Old Saybrook, CT 06475
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  /15

  $8,400 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 $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
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  $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 $824,819

  Last Listing Agent Fran Manganello Coldwell Banker Realty

  92 Fenwood Dr, Old Saybrook, CT 06475
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  Est $1,279,597 Not Listed For Sale

  41 Cypress Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 3,010 Sq Ft
  • Built 1976

  41 Cypress Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 14% Above List Price
  • $374/SF
  • 84 Days On Market

  • Last Sold Price $1,125,000
  • Nov 18, 2024

  Last Listing Agent Lynn Toper CR Premier Properties
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  /35

  $875,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  13 Cove St, Old Saybrook, CT 06475

  Saybrook Point! This fully renovated coastal retreat with partial water views offers an exceptional blend of privacy, charm and effortless lifestyle. Steps aways from desired Saybrook Point, marinas, mini golf, Fenwick Golf Course and a stroll to beaches, restaurants and Main Street - everything that defines the Old Saybrook lifestyle is just steps away. Set on a generous sized lot this home is

  Sharon Linder Berkshire Hathaway NE Prop.

  13 Cove St, Old Saybrook, CT 06475
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  $6,500 Per Month

  • 4 Beds
  • 3 Baths
  • 3,762 Sq Ft
  • House for Rent

  17 Agawam Ave, Old Saybrook, CT 06475

  Fantastic Opportunity to Rent in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage is available from September, 2026, through June 20, 2027! Boasting 4 bedrooms and 4 baths plus a huge third-floor rec room/bunk room space, the home offers over 3,700 sq. ft. of comfortable beach living. Open floor plan living room with walls of windows and French door access to a spacious back

  Lynn Lehrman Re/Max Valley Shore

  17 Agawam Ave, 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 $751,452

  Last Listing Agent Terry Kemper Coldwell Banker Realty

  16 Howard St, Old Saybrook, CT 06475
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  Est $674,880 Not Listed For Sale

  10 Allendale Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,924 Sq Ft
  • Built 1969

  10 Allendale Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 2% Above List Price
  • $343/SF
  • 91 Days On Market

  • Last Sold Price $660,000
  • Aug 09, 2024

  Last Listing Agent Dana Gibson William Raveis Real Estate
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  $1,300,000

  • 2 Beds
  • 2.5 Baths
  • 2,294 Sq Ft

  446 Main St Unit 9, Old Saybrook, CT 06475

  Nestled along the serene shores of North Cove, this exceptional 2,300+ square foot detached shingle-style condo perfectly blends coastal elegance with unmatched privacy. Opportunities like this are rare, as high-end, detached units in this coveted waterfront location seldom become available on the market. The interior showcases a sophisticated open layout featuring a custom chef's kitchen,

  Maureen OGrady Compass Connecticut, LLC

  446 Main St Unit 9, Old Saybrook, CT 06475
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  /27

  $4,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • House for Rent

  509 Main St Unit 4, Old Saybrook, CT 06475

  Rare opportunity --Available June 15 - ANNUAL LEASE! Walk or bike to Saybrook Point or to town! Stunning 3 bedroom Colonial in quaint small enclave of 4 Free Standing condo's with water views is being offered for the first time in years. Fantastic in-town location -- In between North and South Coves, walk or bike to town and Saybrook Point. Hardwood floors, granite kitchen, open floor plan;

  Lisa Genovali Re/Max Valley Shore

  509 Main St Unit 4, 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
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  Est $2,419,510 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

  • 18% Below List Price
  • $698/SF
  • 13 Days On Market

  • Last Sold Price $2,950,000
  • Sep 05, 2024

  Last Listing Agent Teri Lewis William Pitt
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  /40

  $995,000

  • 3 Beds
  • 1.5 Baths
  • 1,772 Sq Ft

  37 Mohican Rd, Old Saybrook, CT 06475

  Nestled in the highly sought-after Cornfield Point Beach community, this beautifully maintained 3-bedroom, 2.5-bath residence offers an exceptional opportunity to enjoy coastal living just steps from the water. Blending timeless charm with thoughtful upgrades, this home is designed for both everyday comfort and effortless entertaining. At the heart of the home is a thoughtfully updated kitchen,

  Wendy Visgilio Coldwell Banker Realty

  37 Mohican Rd, Old Saybrook, CT 06475
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  $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 $672,412

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  37 Woodland Dr, Old Saybrook, CT 06475
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  Est $661,468 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

  • 32% Above List Price
  • $230/SF
  • 78 Days On Market

  • Last Sold Price $500,000
  • Jul 31, 2024

  Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC
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  $985,000 Under Contract

  • 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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  $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 $598,302

  Last Listing Agent Carla Mousch William Raveis Real Estate

  227 Hidden Cove Rd Unit 227, Old Saybrook, CT 06475
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  Est $616,891 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
  • Nov 15, 2024

  Last Listing Agent Dawn D'Auria Coldwell Banker
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  $975,000

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

  18 Old South Cove Rd, Old Saybrook, CT 06475

  Situated in Old Saybrook's most protected and prominent corridor, 18 Old South Cove Road provides the rare opportunity to Renovate or Custom Build a "Legacy Estate" where privacy and scenic integrity are guaranteed by zoning. Currently home to a classic 1,569 Sq. Ft. ranch built in 1964, the true value of this Residential District A property lies in its exceptional dimensions and unique

  Steven Koleno Beycome of Connecticut

  18 Old South Cove Rd, Old Saybrook, CT 06475
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  $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 $875,088

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

  26 College St, Old Saybrook, CT 06475
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  Est $642,342 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

  • 1% Below List Price
  • $555/SF
  • 12 Days On Market

  • Last Sold Price $650,000
  • Aug 09, 2024

  Last Listing Agent Craig Hebert RE/MAX
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  $1,038,880

  • 2 Beds
  • 2 Baths
  • 1,952 Sq Ft

  24 Seabreeze Rd, Old Saybrook, CT 06475

  Nestled in the prestigious Cornfield Point Beach Association neighborhood. This ranch has one-level living, with ocean views! With upgrades and improvements including new flooring, active solar, Thermopane windows, Vinyl Siding, rain gutters, central air and heating system. Huge extra room includes a Murphy bed that could be used as a third bedroom. A spacious open plan living room. Wall to wall

  Brian Beaulieu Berkshire Hathaway NE Prop.

  24 Seabreeze Rd, Old Saybrook, CT 06475
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  $935,000 Sold Dec 16, 2025

  19 Lynde St, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • Built 1918

  Last Sold Summary

  • 1% Above List Price
  • $390/SF
  • 62 Days On Market

  Current Estimated Value $933,935

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  19 Lynde St, Old Saybrook, CT 06475
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  Est $953,077 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

  • $436/SF
  • 17 Days On Market

  • Last Sold Price $949,500
  • Aug 01, 2024

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  $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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  $410,000 Sold Dec 22, 2025

  227 Essex Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Below List Price
  • $397/SF
  • 69 Days On Market

  Current Estimated Value $422,980

  Last Listing Agent Sandy Orsie Berkshire Hathaway NE Prop.

  227 Essex Rd, Old Saybrook, CT 06475
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  Est $1,079,490 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

  • 20% Above List Price
  • $295/SF
  • 33 Days On Market

  • Last Sold Price $900,000
  • Oct 31, 2024

  Last Listing Agent Rose McWaid William Raveis Real Estate
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  $699,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,916 Sq Ft

  3 Deerfield Rd, Old Saybrook, CT 06475

  Exceptional Colonial! This stunning 1916 sq.ft. home is in the desirable Meadowood area, offering convenient access to restaurants, shops, beaches & some water views. It is ideal for commuters, with proximity to I-95, and Boston & New York City only 2.5 hr. away. The home boasts hardwood floors, with a tile floor in the kitchen. The spacious living room is complete with a wood-burning fireplace.

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

  3 Deerfield Rd, Old Saybrook, CT 06475
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  $377,000 Sold Oct 08, 2025

  52 Chalker Beach Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1948

  Last Sold Summary

  • 16% Below List Price
  • $337/SF
  • 77 Days On Market

  Current Estimated Value $445,275

  Last Listing Agent Patrick Farley Statewide Premier Prop. LLC

  52 Chalker Beach Rd, Old Saybrook, CT 06475
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  Est $445,097 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

  • 27% Above List Price
  • $572/SF
  • 48 Days On Market

  • Last Sold Price $350,000
  • May 22, 2024

  Last Listing Agent Matt Diamond Houlihan Lawrence WD
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  /24

  $499,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,404 Sq Ft

  240 Elm St, Old Saybrook, CT 06475

  Welcome to a home where quality meets comfort, starting with a charming brick walkway and vibrant perennials that lead to an inviting front entrance with a character-filled full dining area. This seamless one-floor layout continues into the eat-in kitchen, which boasts a spacious countertop, and a convenient first-floor laundry room complete with a half bath. Relax in the living room, featuring a

  Sang Jee Eagle Eye Realty PLLC

  240 Elm St, Old Saybrook, CT 06475
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  $2,970,000 Sold Apr 24, 2026

  6 Point Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 3 Baths
  • 2,363 Sq Ft
  • Built 1950

  Last Sold Summary

  • 24% Above List Price
  • $1,257/SF
  • 2 Days On Market

  Current Estimated Value $1,952,808

  Last Listing Agent Sue Darmon William Pitt Sotheby's Int'l

  6 Point Rd, Old Saybrook, CT 06475

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