Old Saybrook, CT Homes

• 

  

  

  /40

  $940,000

  • 2 Beds
  • 4 Baths
  • 2,151 Sq Ft

  25 Sheffield St Unit 7, Old Saybrook, CT 06475

  Step into refined, effortless living in this beautifully appointed luxury condo featuring 2 bedrooms, 2 full baths and 2 half baths. A charming entry welcomes you with a thoughtfully designed garden with roses, lilacs and a variety of other plantings setting a warm and inviting tone. Designed with an open floor plan and soaring cathedral ceilings, the space is filled with natural light and an

  Sue Bowes RE/MAX on the Bay

  25 Sheffield St Unit 7, Old Saybrook, CT 06475
• 

  $625,000 Sold Sep 03, 2025

  19 Hartford Ave, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 1,249 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Above List Price
  • $500/SF
  • 47 Days On Market

  Current Estimated Value $623,575

  Last Listing Agent Frank Fonteyn Prestige Realty Group

  19 Hartford Ave, Old Saybrook, CT 06475
• 

  Est $596,203 Not Listed For Sale

  367 Main St Unit 4, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • Built 1980

  367 Main St Unit 4, Old Saybrook, CT 06475

  Last Sold Summary

  • 11% Above List Price
  • $515/SF
  • 4 Days On Market

  • Last Sold Price $536,999
  • Apr 19, 2024

  Last Listing Agent Debbie Lupo The Agency
• 

  

  

  /38

  $6,600,000

  • 6 Beds
  • 4 Baths
  • 5,739 Sq Ft

  11 River Edge Rd, Old Saybrook, CT 06475

  Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 5,739 square feet, this residence combines timeless architectural sophistication with the serene beauty of nature. Additional 1,500 sqft in the lower

  Colette Harron William Pitt Sotheby's Int'l

  11 River Edge Rd, Old Saybrook, CT 06475
• 

  $1,495,000 Sold Dec 01, 2025

  66 Pennywise Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 2,425 Sq Ft
  • Built 1790

  Last Sold Summary

  • 7% Above List Price
  • $616/SF
  • 1 Day On Market

  Current Estimated Value $1,426,476

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  66 Pennywise Ln, Old Saybrook, CT 06475
• 

  Est $1,665,492 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

  • 9% Above List Price
  • $502/SF
  • 62 Days On Market

  • Last Sold Price $1,525,000
  • Jun 18, 2024

  Last Listing Agent Jason Malagutti Dave Jones Realty, LLC
• 

  

  /40

  $3,995,000

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

  41 Watrous Point Rd, Old Saybrook, CT 06475

  Discover one of the most coveted vantage points on the lower Connecticut River-a mid-century modern sanctuary perched on a private 2.7-acre waterfront peninsula where land, river, and sky converge in perfect harmony. With an extraordinary 875 feet of water frontage embracing both the Connecticut River and the pristine Turtle Creek nature preserve, this property is a haven for bird enthusiasts and

  Teri Lewis William Pitt Sotheby's Int'l

  41 Watrous Point Rd, Old Saybrook, CT 06475
• 

  $520,000 Sold May 16, 2025

  25 Sherman St, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,225 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $424/SF
  • 44 Days On Market

  Current Estimated Value $537,136

  Last Listing Agent Ginny Proft William Raveis Real Estate

  25 Sherman St, Old Saybrook, CT 06475
• 

  Est $799,853 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

  • 27% Above List Price
  • $240/SF
  • 151 Days On Market

  • Last Sold Price $630,000
  • Oct 15, 2024

  Last Listing Agent Kevin Geysen William Pitt
• 

  /2

  $19,000 Pending

  • Land
  • 34,848 Sq Ft
  • $23,750 per Acre

  0 Merritt Ln, Old Saybrook, CT 06475

  NOT BUILDABLE LOT! .80 acres overlooking Chalkers Millpond on cul-de-sac .

  Claude Cousins Berkshire Hathaway NE Prop.

  0 Merritt Ln, Old Saybrook, CT 06475
• 

  $575,000 Sold Jun 20, 2025

  3 Clark Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1940

  Last Sold Summary

  • $630/SF
  • 36 Days On Market

  Current Estimated Value $596,956

  Last Listing Agent Lorenda DiMeo Century 21 AllPoints Realty

  3 Clark Ave, Old Saybrook, CT 06475
• 

  Est $1,192,285 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

  • 6% Above List Price
  • $390/SF
  • 28 Days On Market

  • Last Sold Price $1,125,000
  • Oct 03, 2024

  Last Listing Agent Sharon Linder Berkshire Hathaway Home Services
• 

  

  /40

  $799,900 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,090 Sq Ft

  25 Sunset Rd Unit 7, Old Saybrook, CT 06475

  Your chance to own in highly desirable Oyster River Landing-just steps from a private marina and the community's inground pool. This beautifully maintained three-level townhouse offers comfortable luxury, expansive water views, and a lifestyle that blends coastal living with everyday convenience. A sun-filled home features seven rooms, including 2 bedrooms, 2 full bathrooms, 1 half bath, a

  Scott Nardozzi Cavanaugh & Company LLC

  25 Sunset Rd Unit 7, Old Saybrook, CT 06475
• 

  $505,000 Sold Jul 07, 2025

  104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475

  • 2 Beds
  • 1.5 Baths
  • 1,557 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $324/SF
  • 101 Days On Market

  Last Listing Agent Lisa Genovali Re/Max Valley Shore

  104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
• 

  Est $1,039,683 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

  • 9% Above List Price
  • $331/SF
  • 20 Days On Market

  • Last Sold Price $950,000
  • Jan 11, 2024

  Last Listing Agent Colette Harron William Pitt
• 

  

  /40

  $1,179,900

  • 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
• 

  $1,025,000 Sold Jul 25, 2025

  8 Cromwell Place, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,730 Sq Ft
  • Built 1957

  Last Sold Summary

  • 14% Below List Price
  • $275/SF
  • 58 Days On Market

  Current Estimated Value $1,057,619

  Last Listing Agent Roxanne Quinn Coldwell Banker Realty

  8 Cromwell Place, Old Saybrook, CT 06475
• 

  Est $645,351 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

  • 9% Above List Price
  • $242/SF
  • 38 Days On Market

  • Last Sold Price $590,000
  • Jul 15, 2024

  Last Listing Agent Sharon Linder Berkshire Hathaway Home Services
• 

  

  /14

  $329,000 Pending

  • Land
  • 13,503 Sq Ft
  • $1,061,290 per Acre

  124 Old Boston Post Rd, Old Saybrook, CT 06475

  Considering a new build now or in the future? Can't find, "just the right property?" It's time to secure this very special location. Welcome to 124 Old Boston Post Road, an incredible .31 acre building lot in the heart of downtown Old Saybrook. Walk to the Acton Library, Trask Park tennis/pickleball and splash pad and a half mile to Main Street restaurants, shops, town offices and schools. Enjoy

  Nancy Mesham Coldwell Banker Realty

  124 Old Boston Post Rd, Old Saybrook, CT 06475
• 

  $410,000 Sold Jul 15, 2025

  6 West St, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft
  • Built 1930

  Last Sold Summary

  • 11% Below List Price
  • $496/SF
  • 111 Days On Market

  Current Estimated Value $422,811

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  6 West St, Old Saybrook, CT 06475
• 

  Est $603,410 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

  • 10% Above List Price
  • $517/SF
  • 302 Days On Market

  • Last Sold Price $548,000
  • Oct 04, 2023

  Last Listing Agent Steven Koleno Beycome of Connecticut
• 

  

  /29

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft

  49 River St, Old Saybrook, CT 06475

  Spacious village area colonial with lot's of space and in what a location, a short stroll to Main Street and convenient to shops, highways and the railroad station. Featuring 9 rooms and 4 bedrooms with a second upper level kitchenette, this floorplan suits all of your housing needs at a price which won't bust the budget. Could potentially accommodate an in-law use with the second kitchen.

  Rick Allen William Raveis Real Estate

  49 River St, 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 $1,050,583

  Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

  122 Old Post Rd, Old Saybrook, CT 06475
• 

  Est $586,776 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

  • 28% Above List Price
  • $297/SF
  • 43 Days On Market

  • Last Sold Price $460,000
  • Oct 30, 2023

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

  

  /40

  $1,589,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,472 Sq Ft

  2 Old South Cove Rd, Old Saybrook, CT 06475

  At Saybrook Point, life is defined by the water. Morning walks by the marina, kayaking on quiet coves, beach days, coffee downtown, dinner at the Saybrook Point Inn, and summer evenings that feel like a resort vacation without ever leaving home. New construction in this location is nearly impossible to find, and the photos tell the story better than words ever could. Set where water, light, and

  Michael Riccio Calcagni Real Estate

  2 Old South 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 $740,514

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  5 Fox Hollow Rd, Old Saybrook, CT 06475
• 

  Est $1,652,772 Not Listed For Sale

  84 Church St, Old Saybrook, CT 06475

  • 4 Beds
  • 4 Baths
  • 3,567 Sq Ft
  • Built 2006

  84 Church St, Old Saybrook, CT 06475

  Last Sold Summary

  • 20% Above List Price
  • $385/SF
  • 6 Days On Market

  • Last Sold Price $1,375,000
  • Jun 30, 2023

  Last Listing Agent Joel Lucas Coldwell Banker Realty
• 

  

  /40

  $559,000

  • 2 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  92 Bokum Rd, Old Saybrook, CT 06475

  A rare and captivating offering, this enchanting storybook residence has been beautifully reimagined to deliver a seamless blend of historic charm and refined design. Whether you choose to continue its success as a turnkey Airbnb investment or keep it for your own year round or weekend retreat, the possibilities are as inviting as the home itself. Thoughtfully updated with a brand new roof and

  Linda Toscano Coldwell Banker Realty

  92 Bokum Rd, Old Saybrook, CT 06475
• 

  $993,500 Sold May 16, 2025

  11 Beach Rd E, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Below List Price
  • $603/SF
  • 43 Days On Market

  Current Estimated Value $966,516

  Last Listing Agent Kristin Davis Berkshire Hathaway NE Prop.

  11 Beach Rd E, Old Saybrook, CT 06475
• 

  Est $700,715 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

  • 3% Above List Price
  • $270/SF
  • 6 Days On Market

  • Last Sold Price $680,000
  • Aug 30, 2024

  Last Listing Agent Sharon Linder Berkshire Hathaway Home Services
• 

  

  /27

  $599,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  367 Main St Unit 7, Old Saybrook, CT 06475

  WOW! A free-standing condo in the highly sought-after Banbury Crossing community. This stunning 2-bedroom, 2-bath residence offers 1,235 sq. ft. of effortless single-floor living at its finest. From the moment you step inside, you'll notice how natural light pours into the home, creating a bright and uplifting atmosphere throughout. The heart of the home features a beautiful living area anchored

  Susan Santoro William Pitt Sotheby's Int'l

  367 Main St Unit 7, 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 $641,527

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  14 Watrous Point Rd, Old Saybrook, CT 06475
• 

  Est $621,167 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

  • 18% Above List Price
  • $568/SF
  • 2 Days On Market

  • Last Sold Price $525,000
  • Dec 05, 2024

  Last Listing Agent Joel Lucas Coldwell Banker Realty
• 

  

  /34

  $585,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,258 Sq Ft

  16 Lynde St, Old Saybrook, CT 06475

  Located in the center of Old Saybrook, 16 Lynde Street offers convenient proximity to Main Street shops, restaurants, and cafes including Liv's Oyster Bar & Restaurant, Swell, Sweet Luna's, and local boutiques, as well as the Town Green. This classic Cape Cod-style home, owned by one family since construction, reflects consistent maintenance and care. Interior features include hardwood floors

  Jennifer Gurnell William Raveis Real Estate

  16 Lynde St, 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 $729,687

  Last Listing Agent Chloe White KW Legacy Partners

  117 Ayers Point Rd, Old Saybrook, CT 06475
• 

  Est $1,451,308 Not Listed For Sale

  15 Beach View Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 3 Baths
  • 1,956 Sq Ft
  • Built 2016

  15 Beach View Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 16% Above List Price
  • $639/SF
  • 41 Days On Market

  • Last Sold Price $1,250,000
  • May 15, 2023

  Last Listing Agent Rick Weiner William Pitt
• 

  

  /32

  $449,000

  • 1 Bed
  • 1.5 Baths
  • 1,205 Sq Ft

  61 Ingham Hill Rd, Old Saybrook, CT 06475

  Step into the charm of this delightful 1920 year-round bungalow, just a stone's throw from Old Saybrook's stunning beaches. Thoughtfully remodeled, this cozy retreat blends historical character with modern comforts. As you enter, you'll find a spacious area that offers endless possibilities-use it as an eating area, a flex office, or even a sleeping space. The open floor plan invites effortless

  Gigi Giordano Taylor Compass Connecticut, LLC

  61 Ingham Hill Rd, 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 $1,308,808

  Last Listing Agent Lynn Toper CR Premier Properties

  24 Church St, Old Saybrook, CT 06475
• 

  Est $1,026,841 Not Listed For Sale

  15 Briarwood Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 3 Baths
  • 2,643 Sq Ft
  • Built 1958

  15 Briarwood Dr, Old Saybrook, CT 06475

  Last Sold Summary

  • 66% Above List Price
  • $233/SF
  • 4 Days On Market

  • Last Sold Price $617,000
  • Jun 06, 2023

  Last Listing Agent Jennifer Gurnell William Raveis Real Estate
• 

  

  /33

  $5,900,000

  • 4 Beds
  • 4 Baths
  • 5,651 Sq Ft

  12 Rocky Point Rd, Old Saybrook, CT 06475

  Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy

  Sharon Linder Berkshire Hathaway NE Prop.

  12 Rocky Point Rd, Old Saybrook, CT 06475

Showing Results 121 - 160, Page 4 of 18