NOMADEReal Estate
Shoreline & Waterfront Properties

Waterfront Homes in Old Saybrook, CT

100 active listings on the market right now

Discover waterfront homes in Middlesex County in Old Saybrook, CT. Old Saybrook sits where the Connecticut River meets Long Island Sound, offering a vibrant Main Street, multiple beach neighborhoods, the iconic Saybrook Point area, and the famous Katharine Hepburn Cultural Arts Center. It's a beloved shoreline community with deep summer-resident roots. Median home price in Old Saybrook: $575,000. School rating: A-.

Active Listings

Available Waterfront Homes in Old Saybrook

100 Dudley Avenue F30ActiveCondo/Co-Op For Sale
$797,000

100 Dudley Avenue F30

Old Saybrook, Connecticut 06475

2 bd
3 ba
1,565 sqft
71 Knollwood DriveActiveSingle Family For Sale
$799,500

71 Knollwood Drive

Old Saybrook, Connecticut 06475

3 bd
2 ba
1,856 sqft
24 Shore DriveActiveSingle Family For Sale
$1,245,000

24 Shore Drive

Old Saybrook, Connecticut 06475

3 bd
1 ba
884 sqft
93 Elm StreetActiveCommercial For Lease
$21

93 Elm Street

Old Saybrook, Connecticut 06475

5,048 sqft
26 Willard AvenueActiveSingle Family For Sale
$1,175,000

26 Willard Avenue

Old Saybrook, Connecticut 06475

3 bd
2 ba
2,904 sqft
18 Shepard StreetActiveSingle Family For Sale
$699,900

18 Shepard Street

Old Saybrook, Connecticut 06475

3 bd
2 ba
2,114 sqft
2 Captains LaneActiveSingle Family For Sale
$2,899,900

2 Captains Lane

Old Saybrook, Connecticut 06475

5 bd
5 ba
5,062 sqft
11 Fencove CourtActiveSingle Family For Sale
$1,699,000

11 Fencove Court

Old Saybrook, Connecticut 06475

4 bd
3 ba
3,515 sqft
17 College StreetActiveSingle Family For Sale
$1,099,000

17 College Street

Old Saybrook, Connecticut 06475

3 bd
3 ba
1,960 sqft
96 Ayers Point RoadActiveSingle Family For Sale
$1,099,000

96 Ayers Point Road

Old Saybrook, Connecticut 06475

4 bd
3 ba
4,109 sqft
13 Meadowood LaneActiveResidential Rental
$2,300

13 Meadowood Lane

Old Saybrook, Connecticut 06475

1 bd
1 ba
947 sqft
43 Quarry StreetActiveSingle Family For Sale
$285,000

43 Quarry Street

Old Saybrook, Connecticut 06475

3 bd
1 ba
941 sqft
86 Fenwood DriveActiveSingle Family For Sale
$874,900

86 Fenwood Drive

Old Saybrook, Connecticut 06475

2 bd
3 ba
2,209 sqft
880 Boston Post RoadActiveCommercial For Sale
$1,500,000

880 Boston Post Road

Old Saybrook, Connecticut 06475

0 bd
1 ba
13,836 sqft
104 Knollwood DriveActiveSingle Family For Sale
$1,495,000

104 Knollwood Drive

Old Saybrook, Connecticut 06475

3 bd
2 ba
1,809 sqft
1324 Boston Post RoadActiveSingle Family For Sale
$550,000

1324 Boston Post Road

Old Saybrook, Connecticut 06475

3 bd
1 ba
1,104 sqft
46 Farview AvenueActiveSingle Family For Sale
$599,000

46 Farview Avenue

Old Saybrook, Connecticut 06475

3 bd
2 ba
1,552 sqft
37 Woodland DriveActiveSingle Family For Sale
$1,025,000

37 Woodland Drive

Old Saybrook, Connecticut 06475

3 bd
2 ba
1,426 sqft
108 Maple AvenueActiveSingle Family For Sale
$1,550,000

108 Maple Avenue

Old Saybrook, Connecticut 06475

4 bd
4 ba
3,188 sqft
11 Kitteridge Hill RoadActiveSingle Family For Sale
$699,000

11 Kitteridge Hill Road

Old Saybrook, Connecticut 06475

3 bd
3 ba
2,755 sqft
9 Old Colony RoadActiveSingle Family For Sale
$675,000

9 Old Colony Road

Old Saybrook, Connecticut 06475

4 bd
2 ba
1,344 sqft
11 Cambridge CourtActiveSingle Family For Sale
$1,625,000

11 Cambridge Court

Old Saybrook, Connecticut 06475

4 bd
3 ba
2,178 sqft
43 Quarry StreetActiveLots and Land For Sale
$285,000

43 Quarry Street

Old Saybrook, Connecticut 06475

-- sqft
900 Boston Post RoadActiveCommercial For Lease
$24

900 Boston Post Road

Old Saybrook, Connecticut 06475

-- sqft
FAQ

Frequently asked questions

How many waterfront homes are currently for sale in Old Saybrook, CT?

Active inventory in Old Saybrook, CT changes daily as listings come on and go off market. The grid above shows the most recently updated listings — refresh for the latest count.

What is the median home price in Old Saybrook, CT?

The median home price in Old Saybrook, CT is approximately $575,000. Actual sale prices depend on location, condition, lot size, and timing of the listing.

What are property taxes like in Old Saybrook, CT?

Old Saybrook has a mill rate of approximately 20.90. Annual taxes equal the mill rate × the assessed value (70% of fair market value) ÷ 1,000.

Can Nomade Real Estate help me buy a home in Old Saybrook, CT?

Yes. Nomade represents buyers across all eight Connecticut counties with on-the-ground knowledge of Old Saybrook, CT pricing, schools, commute, and what makes each neighborhood different. Reach out via the contact form on any property page to start a search.

Is Old Saybrook a good place to live year-round?

Yes — while Old Saybrook has a strong summer-resident base, the year-round community is engaged with active downtown, schools, and arts. The lower mill rate (20.90) makes it especially attractive.

Looking in Old Saybrook?

Talk to a Nomade agent who actually knows Old Saybrook— pricing, schools, taxes, and what's not on the MLS yet.