Old Saybrook, CT Homes

• 

  Est $651,136

  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
• 

  

  

  /39

  $2,200,000

  Open Sat 12PM - 2PM

  • 4 Beds
  • 4 Baths
  • 3,188 Sq Ft

  108 Maple Ave, Old Saybrook, CT 06475

  Contemporary coastal elegance meets exceptional privacy along South Cove in Old Saybrook. Set on an extraordinary 1.8-acre parcel, this cedar-sided, 3,188-square-foot residence offers breathtaking water views from nearly every room and a setting that is virtually impossible to recreate. Designed to capture its spectacular surroundings, the home features vaulted ceilings, expansive windows, and

  Jessica Blancato William Pitt Sotheby's Int'l

  108 Maple Ave, 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 $756,269

  Last Listing Agent Chloe White KW Legacy Partners

  117 Ayers Point Rd, Old Saybrook, CT 06475
• 

  Est $768,753

  Not Listed For Sale

  4 Old Colony Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1958

  4 Old Colony Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 14 Days On Market
• 

  

  

  /40

  $755,000

  $40K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,720 Sq Ft

  46 Lynde St, Old Saybrook, CT 06475

  Convenient & Desirable In-Town Living with Stunning New Kitchen & Accessible Primary Suite with Heated Bath Floor! This thoughtfully updated ranch offers over 1,700+ square feet of above-grade living space and delivers a true in-town lifestyle just moments from everything Old Saybrook has to offer. Spacious yet cozy, inviting, and sun-drenched, this one-level home features a large backyard with

  Stephano Stravoravdis Real Broker CT, LLC

  46 Lynde St, 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 $1,343,695

  Last Listing Agent Lynn Toper CR Premier Properties

  24 Church 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
• 

  

  /40

  $1,665,000

  Open Sun 12PM - 2PM $125K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,125 Sq Ft

  5 Woodland Dr, Old Saybrook, CT 06475

  Rare opportunity to enjoy sweeping views of Long Island Sound from a quiet street just off Maple Avenue in sought-after Knollwood Beach. This beautifully renovated 3-bedroom, 3-bath coastal retreat, just one street from the water, offers unobstructed views and is ideal as a year-round home or second getaway. The bright, open floor plan is designed to capture the scenery, with an oversized

  Joel Lucas Coldwell Banker Realty

  5 Woodland Dr, 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 $144,615

  Last Listing Agent Katie Schubert KW Legacy Partners

  6 South St, Old Saybrook, CT 06475
• 

  Est $577,055

  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
• 

  

  /40

  $1,100,000

  Open Sat 11AM - 1PM

  • 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
• 

  $625,000

  Sold Sep 19, 2025

  3 Glen Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,915 Sq Ft
  • Built 1969

  Last Sold Summary

  • $326/SF
  • 68 Days On Market

  Current Estimated Value $659,235

  Last Listing Agent Lisa Genovali Re/Max Valley Shore

  3 Glen Dr, Old Saybrook, CT 06475
• 

  Est $544,358

  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
• 

  

  /40

  $645,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,890 Sq Ft

  2 Cinnamon Way, Old Saybrook, CT 06475

  Surrounded by a peaceful preserve with beautiful views, this light filled custom contemporary Colonial offers a rare blend of privacy, flexibility, and classic Old Saybrook charm. Step through the new custom front door into an open, airy layout where natural light pours through new windows and skylights, setting a warm tone from the moment you enter. The stylish kitchen features stainless steel

  Julie Corrado Coldwell Banker Realty

  2 Cinnamon Way, 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 $914,625

  Last Listing Agent Linda Toscano Coldwell Banker Realty

  1 Beamon Meadow Place, Old Saybrook, CT 06475
• 

  Est $983,852

  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
• 

  

  /31

  $529,000

  • 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
• 

  $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 $677,260

  Last Listing Agent George Agnelli Agnelli Real Estate

  12 Bellaire Dr, Old Saybrook, CT 06475
• 

  Est $701,561

  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
• 

  

  /12

  $12,000,000

  • 4 Beds
  • 1 Bath
  • 2,059 Sq Ft

  1445 Boston Post Rd, Old Saybrook, CT 06475

  A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a

  Casey Fisher Houlihan Lawrence WD

  1445 Boston Post Rd, 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 $821,152

  Last Listing Agent Dylan Walter William Raveis Real Estate

  11 S View Terrace, Old Saybrook, CT 06475
• 

  Est $605,416

  Not Listed For Sale

  95 Chalker Beach Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1952

  95 Chalker Beach Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 35 Days On Market
• 

  

  /32

  $699,000

  Open Sun 12PM - 2PM

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

  52 Chalker Beach Rd, Old Saybrook, CT 06475

  No stone was left unturned at this turn key beach house in the Chalker Beach Association! Completely and professionally renovated from bottom to top, this 3 bedroom cottage is open, light and airy and ready for you to move in, just in time for summer! A spacious living room opens into the lovely eat-in kitchen with custom cabinets, stainless steel appliances and beautiful crown moulding. A bright

  Tina Rupp William Pitt Sotheby's Int'l

  52 Chalker Beach 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 $491,263

  Last Listing Agent Tim O'Hara William Raveis Real Estate

  258 School House Rd, Old Saybrook, CT 06475
• 

  Est $852,079

  Not Listed For Sale

  11 Shepard St, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1865

  11 Shepard St, Old Saybrook, CT 06475

  Last Sold Summary

  • 10 Days On Market
• 

  

  /17

  $850,000

  Under Contract

  • Land
  • 26.41 Acres
  • $32,185 per Acre

  62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475

  Beautiful 26+ Acre Wooded Lot with Subdivision Potential. This stunning 26+ acre wooded parcel offers incredible potential for a variety of uses-from a private gentleman's farm to a multi-generational compound or subdivision development. Bucolic stone walls and mature trees create a serene, timeless setting. The sale includes parcels identified as Tax Map 62, Lots 14, 15, and 16. Access is

  Kevin Kennedy Kennedy Real Estate Solutions

  62-14,15,16 Middlesex Turnpike, 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 $979,294

  Last Listing Agent Jennifer Gurnell William Raveis Real Estate

  4 Fenwood Ln, Old Saybrook, CT 06475
• 

  Est $612,340

  Not Listed For Sale

  41 Dudley Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,621 Sq Ft
  • Built 1940

  41 Dudley Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 42 Days On Market
• 

  

  /39

  $1,790,000

  $200K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,745 Sq Ft

  4 Beach Rd, Old Saybrook, CT 06475

  Welcome to the coastal lifestyle you've been dreaming of, where beach days, sunset strolls, boating adventures, and the relaxed charm of shoreline living are part of everyday life. This impeccably maintained home with breathtaking, expansive marsh views, featuring a timeless elegance with modern luxury at every turn. The home features a spectacular, fully renovated chef's kitchen featuring

  Sharon Linder Berkshire Hathaway NE Prop.

  4 Beach Rd, Old Saybrook, CT 06475
• 

  $375,000

  Sold Sep 05, 2025

  49 Hartford Ave, Old Saybrook, CT 06475

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

  Last Sold Summary

  • 25% Below List Price
  • $744/SF
  • 41 Days On Market

  Current Estimated Value $410,690

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  49 Hartford Ave, Old Saybrook, CT 06475
• 

  Est $879,819

  Not Listed For Sale

  5 Barley Hill Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 5 Baths
  • 3,048 Sq Ft
  • Built 1995

  5 Barley Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 56 Days On Market
• 

  

  /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
• 

  $925,000

  Sold Sep 22, 2025

  45 Farview Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,791 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Above List Price
  • $331/SF
  • 11 Days On Market

  Current Estimated Value $950,046

  Last Listing Agent Amy Rubin William Raveis Real Estate

  45 Farview Ave, Old Saybrook, CT 06475
• 

  Est $1,449,740

  Not Listed For Sale

  32 Willard Ave, Old Saybrook, CT 06475

  • 5 Beds
  • 3.5 Baths
  • 3,502 Sq Ft
  • Built 1961

  32 Willard Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 55 Days On Market
• 

  

  /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
• 

  $720,000

  Sold Mar 03, 2026

  41 Briarwood Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 2.5 Baths
  • 1,076 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $669/SF
  • 47 Days On Market

  Current Estimated Value $732,544

  Last Listing Agent Rick Allen William Raveis Real Estate

  41 Briarwood Dr, Old Saybrook, CT 06475
• 

  Est $540,925

  Not Listed For Sale

  10 Vista Terrace, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Built 1955

  10 Vista Terrace, Old Saybrook, CT 06475

  Last Sold Summary

  • 70 Days On Market
• 

  

  /21

  $2,000,000

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  14 Anchorage Ln, Old Saybrook, CT 06475

  This exceptional Cape Cod-style waterfront home has the perfect blend of luxury, comfort, and coastal charm. Nestled on a private canal off the CT River, the recently renovated open concept design features a dramatic vaulted Great Room with a wood-burning stove and expansive windows that fill the home with natural light. The gourmet eat-in kitchen is designed for both everyday living and

  Steven Koleno Beycome of Connecticut

  14 Anchorage Ln, Old Saybrook, CT 06475
• 

  $2,125,000

  Sold Oct 10, 2025

  515 Maple Ave, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Above List Price
  • $1,557/SF
  • 38 Days On Market

  Current Estimated Value $2,252,188

  Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

  515 Maple Ave, Old Saybrook, CT 06475
• 

  Est $1,411,022

  Not Listed For Sale

  6 Parkman Place, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,301 Sq Ft
  • Built 2002

  6 Parkman Place, Old Saybrook, CT 06475

  Last Sold Summary

  • 0 Days On Market

Showing Results 161 - 200, Page 5 of 18