Most expensive homes for sale in Old Saybrook, CT

$3,995,000

4 beds • 4.5 baths • 3,518 sqft

175 N Cove Rd, Old Saybrook, CT 06475

#24090901, Kyle Hinding, Listing Office: Coldwell Banker Realty

$3,395,000

5 beds • 6.5 baths • 4,269 sqft

48 Sound Bch, Old Greenwich, CT 06870

#H6328930, Listing Office: Coldwell Banker Realty

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$2,850,000

3 beds • 3 baths • 4,789 sqft

372 Maple Ave, Old Saybrook, CT 06475

#24051865, Colleen Nemec, Listing Office: Showcase Realty, Inc.

$10,000 Closing Credit¹

$2,345,000

1 bed • 1.5 baths • 7,985 sqft

125 Main St, Old Saybrook, CT 06475

#24063444, Gary Marino, Listing Office: William Raveis Real Estate

$10,000 Closing Credit¹

$1,895,000

3 beds • 3.5 baths • 2,500 sqft

2 Old S Cove Road, Old Saybrook, CT 06475

#24086895, Michael Riccio, Listing Office: Calcagni Real Estate

$10,000 Closing Credit¹

$1,850,000

4 beds • 2.5 baths • 2,994 sqft

4 Old Fenwick Rd, Old Saybrook, CT 06475

#24076865, Joel Lucas, Listing Office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,575,000

3 beds • 2.5 baths • 2,236 sqft

26 Meadowood Ln, Old Saybrook, CT 06475

#24087397, Jennifer Gurnell, Listing Office: William Raveis Real Estate

Room to negotiate?

Median Sold Price

$691.2K

Based on our April 2025 Market Report.

$10,000 Closing Credit¹

$1,495,000

4 beds • 4 baths • 4,546 sqft

30 Watrous Point Rd, Old Saybrook, CT 06475

#24076728, Nancy Mesham, Listing Office: Coldwell Banker Realty

Backup offers

$10,000 Closing Credit¹

$1,490,000

5 beds • 4 baths • 4,792 sqft

55 Otter Cove Dr, Old Saybrook, CT 06475

#24077497, Kristina Demaria, Listing Office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,299,000

3 beds • 3 baths • 2,132 sqft

15 Buckingham Ave, Old Saybrook, CT 06475

#24088424, Colette Harron, Listing Office: William Pitt Sotheby's Int'l

$10,000 Closing Credit¹

$1,250,000

3 beds • 1.5 baths • 1,408 sqft

21 Wildwood Rd, Old Saybrook, CT 06475

#24090361, Marc DeLise, Listing Office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,145,000

3 beds • 2.5 baths • 3,286 sqft

1 Lighthouse Ln, Old Saybrook, CT 06475

#24093509, Lynne Ferrigno, Listing Office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,095,000

5 beds • 3 baths • 2,898 sqft

26 College St, Old Saybrook, CT 06475

#24093401, Joel Lucas, Listing Office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,085,000

2 beds • 2 baths • 1,952 sqft

24 Seabreeze Rd, Old Saybrook, CT 06475

#24084826, Brian Beaulieu, Listing Office: KW Legacy Partners

$10,000 Closing Credit¹

$949,900

3 beds • 1 bath • 762 sqft

27 Barnes Rd, Old Saybrook, CT 06475

#24095679, Debra Pliego, Listing Office: Essentia Realty

$10,000 Closing Credit¹

$949,000

4 beds • 2 baths • 2,249 sqft

86 Chalker Beach Rd, Old Saybrook, CT 06475

#24092785, Jodi Serapilia, Listing Office: William Raveis Real Estate

6 days on Rocket

$10,000 Closing Credit¹

$929,000

3 beds • 1 bath • 1,104 sqft

12 Bellaire Dr, Old Saybrook, CT 06475

#24098228, George Agnelli, Listing Office: Agnelli Real Estate

$10,000 Closing Credit¹

$925,000

4 beds • 2.5 baths • 4,559 sqft

134 School House Rd, Old Saybrook, CT 06475

#24094378, Tina Rupp, Listing Office: William Pitt Sotheby's Int'l

$10,000 Closing Credit¹

$899,900

3 beds • 3 baths • 2,261 sqft

10 Cottage Ave, Old Saybrook, CT 06475

#24086621, Joe Scarpellino, Listing Office: Coldwell Banker Realty

$10,000 Closing Credit¹

$889,900

4 beds • 2.5 baths • 3,472 sqft

3 Town Beach Rd, Old Saybrook, CT 06475

#24080659, George Agnelli, Listing Office: Agnelli Real Estate

$10,000 Closing Credit¹

$859,900

4 beds • 2.5 baths • 2,756 sqft

24 Lynde St, Old Saybrook, CT 06475

#24092439, Carol York, Listing Office: For Sale By Owner Connecticut

$10,000 Closing Credit¹

$849,500

3 beds • 1 bath • 890 sqft

78 Hartford Ave, Old Saybrook, CT 06475

#24091706, Robert Perriello, Listing Office: Century 21 AllPoints Realty

$9,856 Closing Credit¹

$830,000

3 beds • 2 baths • 1,452 sqft

45 Knollwood Dr, Old Saybrook, CT 06475

#24093931, Rose McWaid, Listing Office: William Raveis Real Estate

Backup offers

$9,488 Closing Credit¹

$799,000

3 beds • 2.5 baths • 2,152 sqft

107 Ayers Point Rd, Old Saybrook, CT 06475

#24090432, Joel Lucas, Listing Office: Coldwell Banker Realty

$9,132 Closing Credit¹

$769,000

2 beds • 2 baths • 1,500 sqft

37 Woodland Dr, Old Saybrook, CT 06475

#24085997, Joel Lucas, Listing Office: Coldwell Banker Realty

5 days on Rocket

$8,609 Closing Credit¹

$725,000

3 beds • 3.5 baths • 5,016 sqft

18 King St, Old Saybrook, CT 06475

#24098255, Jennifer Gurnell, Listing Office: William Raveis Real Estate

$8,307 Closing Credit¹

$699,500

2 beds • 1 bath • 1,070 sqft

28 Cypress Rd, Old Saybrook, CT 06475

#24094439, Rick Loranger, Listing Office: Coldwell Banker Realty

Backup offers

$8,301 Closing Credit¹

$699,000

3 beds • 2.5 baths • 1,870 sqft

7 Beaver Dam Trl, Old Saybrook, CT 06475

#24093818, Joel Lucas, Listing Office: Coldwell Banker Realty

Backup offers

$8,253 Closing Credit¹

$695,000

2 beds • 2.5 baths • 1,830 sqft

100 Sheffield St Unit B4, Old Saybrook, CT 06475

#24095974, Kevin Geysen, Listing Office: William Pitt Sotheby's Int'l

14 Meadowood Ln, Old Saybrook, CT 06475 - colonial home featuring an attached garage, driveway, a front yard, and a chimney

Coming soon

$7,113 Closing Credit¹

$599,000

3 beds • 2 baths • 1,812 sqft

14 Meadowood Ln, Old Saybrook, CT 06475

#24099185, Rick Allen, Listing Office: William Raveis Real Estate

$7,054 Closing Credit¹

$594,000

2 beds • 1.5 baths • 1,557 sqft

118 Sandy Point Rd Unit 118, Old Saybrook, CT 06475

#24079450, Carla Mousch, Listing Office: William Raveis Real Estate

Backup offers

$6,828 Closing Credit¹

$575,000

3 beds • 1.5 baths • 1,203 sqft

15 Waterbury Ave, Old Saybrook, CT 06475

#24080952, Eric Engdall, Listing Office: Coldwell Banker Realty

$6,828 Closing Credit¹

$575,000

3 beds • 1.5 baths • 1,176 sqft

5 Aladdin Ave, Old Saybrook, CT 06475

#24076371, Matt Diamond, Listing Office: Houlihan Lawrence WD

Backup offers

$6,828 Closing Credit¹

$575,000

2 beds • 1 bath • 912 sqft

3 Clark Ave, Old Saybrook, CT 06475

#24093785, Lorenda Dimeo, Listing Office: Century 21 AllPoints Realty

$6,757 Closing Credit¹

$569,000

3 beds • 1 bath • 1,196 sqft

14 Denmore Ln, Old Saybrook, CT 06475

#24092177, Terence Dominick, Listing Office: Complete Real Estate

Backup offers

$6,531 Closing Credit¹

$550,000

4 beds • 2 baths • 2,112 sqft

69 Essex Rd, Old Saybrook, CT 06475

#24089090, Brittany O'hara, Listing Office: William Raveis Real Estate

Backup offers

$6,233 Closing Credit¹

$524,900

2 beds • 2 baths • 922 sqft

25 Chalker Beach Rd, Old Saybrook, CT 06475

#24072448, Susan Malton, Listing Office: Coldwell Banker Realty

Backup offers

$6,233 Closing Credit¹

$524,900

2 beds • 1.5 baths • 1,557 sqft

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

#24083727, Lisa Genovali, Listing Office: Re/Max Valley Shore

$5,926 Closing Credit¹

$499,000

1 bed • 1 bath • 504 sqft

49 Hartford Ave, Old Saybrook, CT 06475

#24093479, Sharon Linder, Listing Office: Berkshire Hathaway NE Prop.

$5,581 Closing Credit¹

$470,000

2 beds • 1 bath • 576 sqft

74 Chalker Beach Rd, Old Saybrook, CT 06475

#24096521, Jackie Lyman, Listing Office: Lyman Real Estate

Old Saybrook, CT Real Estate Market Overview

There are 44 most expensive homes for sale in Old Saybrook, CT. The following market insights reflect all property types in the Old Saybrook, CT real estate market. In April 2025 in Old Saybrook, CT there were 22.4% more homes for sale than in March 2025. While the average time on the market in April 2025 was 0 days, the median list price was $691,222. In April 2025 more than 8 listings in Old Saybrook, CT were sold above the asking price. During the same period more than 0 listings were sold at asking price, while more than 1 were sold below.

From Rocket Homes Real Estate and based on county public records data

Most expensive homes for sale in Old Saybrook, CT

Old Saybrook, CT Real Estate Market Overview

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Housing market reports in Middlesex County

Homes for sale near Old Saybrook, CT

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