Old Saybrook, CT Homes

• 

  $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

  Last Listing Agent Sandy Orsie Berkshire Hathaway NE Prop.

  227 Essex Rd, Old Saybrook, CT 06475
• 

  Est $528,394 Not Listed For Sale

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

  235 Hidden Cove Rd, Old Saybrook, CT 06475

  235 Hidden Cove Rd, Old Saybrook, CT 06475
• 

  

  

  /24

  $459,999

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  5 Sunrise Ave, Old Saybrook, CT 06475

  Welcome to 5 Sunrise Ave., Old Saybrook on the Connecticut Shoreline nothing to do with this one level ranch. This lovely home has three bedrooms, updated bath, updated kitchen, dining / living room. Hardwood floors, Stainless Steel Appliances, white cabinetry and an island for the inspiring chef to create and perfect their culinary skills. Entertain at home enjoy a lovely backyard with an

  Terry McDonald McDonald Real Estate, LLC

  5 Sunrise Ave, Old Saybrook, CT 06475
• 

  $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 $406,575

  Last Listing Agent Patrick Farley Statewide Premier Prop. LLC

  52 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  Est $981,003 Not Listed For Sale

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

  8 Maynard Cir, Old Saybrook, CT 06475

  8 Maynard Cir, Old Saybrook, CT 06475
• 

  

  /27

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  1780 Boston Post Rd, Old Saybrook, CT 06475

  Commercial Mixed Use, cross-posted on MLS alternative # 24149460. 7.06 CAP r a t e ~ Prime mixed-use investment property offered at $850,000 along the high-visibility Route 1 corridor. The asset consists of three total units of office/retail space with direct road frontage and two residential apartments privately situated in the rear. Trusted General Contractor currently rents the rear yard space

  Nicholas Tarquino Carbutti & Co., Realtors

  1780 Boston Post Rd, 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

  Last Listing Agent Jeanette Baigert Berkshire Hathaway NE Prop.

  Unlisted Address
• 

  Est $427,675 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  7 North St, Old Saybrook, CT 06475

  7 North St, Old Saybrook, CT 06475
• 

  

  /40

  $2,550,000

  • 3 Beds
  • 3 Baths
  • 3,389 Sq Ft

  372 Maple Ave, Old Saybrook, CT 06475

  Most beach homes ask you to choose: location or amenities, space or style, primary home or vacation retreat. This one says "why not both?" Perfectly positioned just 50 steps from Knollwood Beach, this spacious 3-bedroom 3-bath sanctuary delivers the rare combination of prime beach access and every amenity you'd expect from a year-round residence. A stress free move-in is possible here, as this

  Teri Lewis William Pitt Sotheby's Int'l

  372 Maple 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 $888,704

  Last Listing Agent Mary McDonald Coldwell Banker Realty

  122 College St, Old Saybrook, CT 06475
• 

  Est $457,830 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 910 Sq Ft

  29 Whitewood St, Old Saybrook, CT 06475

  29 Whitewood St, Old Saybrook, CT 06475
• 

  

  /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
• 

  $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

  Last Listing Agent Lynne Ferrigno Coldwell Banker Realty

  1 Lighthouse Ln, Old Saybrook, CT 06475
• 

  Est $538,576 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,107 Sq Ft

  20 Whitney Ave, Old Saybrook, CT 06475

  20 Whitney Ave, Old Saybrook, CT 06475
• 

  

  /5

  $575,000

  • Land
  • 0.48 Acre
  • $1,197,917 per Acre

  10 Mulberry St, Old Saybrook, CT 06475

  Approved building lot with water views. Located at the end of Mulberry, very private location yet close to downtown and Saybrook Point Resort & Marina. 1/2 ac already cleared. Lot must be sold with 7 Willard Ave

  Steve Wollman Wollman Realty

  10 Mulberry St, 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 $628,896

  Last Listing Agent Bryan Neurath Country Manor Realty

  1 Hartford Ave, Old Saybrook, CT 06475
• 

  Est $1,275,218 Not Listed For Sale

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

  11 Beechwood Rd, Old Saybrook, CT 06475

  11 Beechwood Rd, Old Saybrook, CT 06475
• 

  

  /35

  $625,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,744 Sq Ft

  103 Maple Ave, Old Saybrook, CT 06475

  Well-maintained 1,744 sq ft ranch offering easy one-floor living in a desirable location near beaches and the town center. Features include 2 bedrooms, including a primary suite with private bath, hardwood floors, three fireplaces, and a bright kitchen with skylight. Recent updates include a new roof and septic system. Additional highlights include a partially finished basement, 2-car garage, and

  Lisa Golebiewski Coldwell Banker Realty

  103 Maple Ave, 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 $744,354

  Last Listing Agent Jake Pulcini Chiarito Real Estate LLC

  509 Main St Unit 6, Old Saybrook, CT 06475
• 

  Est $611,411 Not Listed For Sale

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

  175 Ferry Rd Unit 8, Old Saybrook, CT 06475

  175 Ferry Rd Unit 8, Old Saybrook, CT 06475
• 

  

  /35

  $599,000

  • 2 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  100 Dudley Ave Unit H43, Old Saybrook, CT 06475

  Beautiful Condominium offered in Sheltered Cove. Set within the serene, meticulously maintained grounds of Sheltered Cove, this charming two-story condominium offers a rare chance to enjoy North Cove and the Connecticut River. Expansive lawns, picturesque views and tranquil surroundings create a setting that feels both private and welcoming. Residents enjoy a newly remodeled swimming pool,

  Robin Linares William Pitt Sotheby's Int'l

  100 Dudley Ave Unit H43, 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 $734,583

  Last Listing Agent Craig Milton Re/Max Valley Shore

  8 Acorn Dr, Old Saybrook, CT 06475
• 

  Est $1,412,483 Not Listed For Sale

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

  9 Watrous Point Rd, Old Saybrook, CT 06475

  9 Watrous Point Rd, Old Saybrook, CT 06475
• 

  

  /7

  $495,000 Under Contract

  • 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
• 

  $476,000 Sold Feb 19, 2025

  12 Forest Glen Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 2,248 Sq Ft
  • Built 1979

  Last Sold Summary

  • 39% Below List Price
  • $212/SF
  • 207 Days On Market

  Current Estimated Value $523,911

  Last Listing Agent Nick Prevost William Raveis Real Estate

  12 Forest Glen Rd, Old Saybrook, CT 06475
• 

  Est $604,335 Not Listed For Sale

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

  1 Dwayne Rd, Old Saybrook, CT 06475

  1 Dwayne Rd, Old Saybrook, CT 06475
• 

  

  /40

  $4,250,000

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

  41 Watrous Point Rd, Old Saybrook, CT 06475

  Presenting a single level light-filled mid-century modern masterpiece, set on a prominent 2.7 acre private waterfront peninsula! Enjoy 875' of frontage along the CT River and adjacent Turtle Creek nature preserve. This dreamlike property comes with two docks. A deep water dock on the river, plus a second dock on Turtle Creek! Drink in views from Essex Harbor to the north, across the river to Old

  Rick Weiner William Pitt Sotheby's Int'l

  41 Watrous Point Rd, Old Saybrook, CT 06475
• 

  $555,000 Sold Mar 28, 2025

  4 Patterson Place, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,752 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $317/SF
  • 60 Days On Market

  Current Estimated Value $572,228

  Last Listing Agent Lynn Lehrman Re/Max Valley Shore

  4 Patterson Place, Old Saybrook, CT 06475
• 

  Est $746,416 Not Listed For Sale

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

  32 Cricket Ct, Old Saybrook, CT 06475

  32 Cricket Ct, Old Saybrook, CT 06475
• 

  

  /40

  $675,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 2,272 Sq Ft

  33 Briarwood Dr, Old Saybrook, CT 06475

  Direct waterfront property on a private lot at 33 Briarwood Drive with expansive marsh and tidal channel views. This well maintained three bedroom two bath home features hardwood floors throughout and an open spacious interior layout. The bright studio space positioned well for a future glass enclosed sunroom offers flexible room for work hobbies or quiet relaxation. The setting provides a strong

  Jennifer Gurnell William Raveis Real Estate

  33 Briarwood Dr, Old Saybrook, CT 06475
• 

  $225,000 Sold Mar 24, 2025

  711 Middlesex Turnpike, Old Saybrook, CT 06475

  • Land
  • 2.2 Acres
  • $102,273 per Acre

  Last Sold Summary

  • 25% Below List Price
  • 147 Days On Market

  Current Estimated Value $231,158

  Last Listing Agent Rick Allen William Raveis Real Estate

  711 Middlesex Turnpike, Old Saybrook, CT 06475
• 

  Est $638,153 Not Listed For Sale

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

  6 Willard St, Old Saybrook, CT 06475

  6 Willard St, Old Saybrook, CT 06475
• 

  

  /25

  $595,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  18 Quarry St, Old Saybrook, CT 06475

  Downtown Old Saybrook Home | First-Floor Primary Suite | Walk to Town & Beach. This classic New England-style home nestled on a quiet dead-end street just steps from downtown Old Saybrook. Enjoy sidewalks leading to shops, restaurants, library, beaches, parks, and schools-everything you love is within easy reach. Set on a cleared half-acre lot, this property features professional landscaping with

  Jennifer Gurnell William Raveis Real Estate

  18 Quarry St, Old Saybrook, CT 06475
• 

  $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

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

  55 Cypress Rd, Old Saybrook, CT 06475
• 

  Est $642,050 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,016 Sq Ft

  24 Middletown Ave, Old Saybrook, CT 06475

  24 Middletown Ave, Old Saybrook, CT 06475
• 

  $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 $523,600

  Last Listing Agent Susan Malton Coldwell Banker Realty

  25 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  Est $531,253 Not Listed For Sale

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

  10 Cliff Dr, Old Saybrook, CT 06475

  10 Cliff Dr, Old Saybrook, CT 06475
• 

  $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 $537,880

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

  18 Lynde St, Old Saybrook, CT 06475
• 

  Est $708,114 Not Listed For Sale

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

  21 Nehantic Trail, Old Saybrook, CT 06475

  21 Nehantic Trail, 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 $612,044

  Last Listing Agent Frank Fonteyn Prestige Realty Group

  19 Hartford Ave, Old Saybrook, CT 06475

Showing Results 81 - 120, Page 3 of 18