Sailboat Waterfront Homes and Condos

To be considered sailboat waterfront and property must not have access restricted by fixed bridges or shallow water.

Sailboat Waterfront on Siesta Key

All Listings $200,000 - $300,000 $300,000 - $400,000
$400,000 - $500,000 $500,000 - $600,000 $600,000 - $700,000
$700,000 - $800,000 $800,000 - $900,000 $900,000 - $1,000,000
Over $1,000,000
55 Properties Found. Showing Page 1 of 5
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Status Price Type City Bed Bath Subdiv Address SqFt
Situated On 1.5 Acres ...
Status:
Not FC
Price:
$11,900,000
Type:
Single Family Home
City:
Siesta Key
Beds:
6
Baths:
5
Subdiv:
Hidden Harbor
Address:
1300 Hidden Harbor Way
SqFt:
6,850
One-of-a-kind Beachfro...
Status:
Not FC
Price:
$8,250,000
Type:
Single Family Home
City:
Siesta Key
Beds:
4
Baths:
6
Subdiv:
Siesta Rev Of
Address:
3975 Shell Rd
SqFt:
5,079
Tucked Away On North S...
Status:
Not FC
Price:
$5,750,000
Type:
Single Family Home
City:
Siesta Key
Beds:
6
Baths:
9
Subdiv:
Siesta Rev Of
Address:
3701 White Ln
SqFt:
7,376
The Style: Pure Palm B...
Status:
Not FC
Price:
$5,495,000
Type:
Single Family Home
City:
Siesta Key
Beds:
4
Baths:
5
Subdiv:
Cocoanut Bayou
Address:
4205 Higel Ave
SqFt:
8,571
Gorgeous Waterfront Es...
Status:
Not FC
Price:
$4,988,000
Type:
Single Family Home
City:
Siesta Key
Beds:
4
Baths:
5
Subdiv:
Siesta Rev Of
Address:
3550 Bayou Louise Ln
SqFt:
4,931
This Is Siesta Key's "...
Status:
Not FC
Price:
$3,950,000
Type:
Single Family Home
City:
Siesta Key
Beds:
6
Baths:
8
Subdiv:
Ocean View
Address:
8233 Midnight Pass Rd
SqFt:
7,648
Paradise Found On Sies...
Status:
Not FC
Price:
$3,599,000
Type:
Single Family Home
City:
Siesta Key
Beds:
4
Baths:
5
Subdiv:
Ocean View
Address:
8307 Midnight Pass Rd
SqFt:
5,312
Bay Breezes From This ...
Status:
Not FC
Price:
$3,295,000
Type:
Single Family Home
City:
Siesta Key
Beds:
4
Baths:
5
Subdiv:
Siesta Beach
Address:
767 Tropical Cir
SqFt:
5,011
Incredible North Siest...
Status:
Not FC
Price:
$3,099,000
Type:
Single Family Home
City:
Siesta Key
Beds:
4
Baths:
4
Subdiv:
Bay Island Shores
Address:
3535 Flamingo Ave
SqFt:
4,103
Coastal Design And Arc...
Status:
Not FC
Price:
$2,999,000
Type:
Single Family Home
City:
Siesta Key
Beds:
5
Baths:
6
Subdiv:
Royal Palm Harbor
Address:
1208 Northport Dr
SqFt:
5,980
Delight In Serene Bayf...
Status:
Not FC
Price:
$2,995,000
Type:
Single Family Home
City:
Siesta Key
Beds:
6
Baths:
7
Subdiv:
Hidden Harbor
Address:
5151 Jungle Plum Rd
SqFt:
6,812
Just Move In And Start...
Status:
Not FC
Price:
$2,250,000
Type:
Single Family Home
City:
Siesta Key
Beds:
4
Baths:
4
Subdiv:
Siesta Beach
Address:
815 Tropical Cir
SqFt:
7,019
Status: Not FC = Not Foreclosure, SS = Short Sale, BO = Bank Owned

Situated On 1.5 Acres ...

$11,900,000
Siesta Key, FL
6 br, 5 ba, 6,850 ft², Single Family Home Residential
Price:
$11,900,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
354 DOM
Type:
Single Family Home
Beds:
6 br,
Baths:
5 ba
Subdiv:
Hidden Harbor
SqFt:
6,850 SqFt

Situated On 1.5 Acres On A Private Peninsula, Also, 3 Dedicated Building Lots, Hidden Harbor Is ...

Photo of Listing #A4156345

One-of-a-kind Beachfro...

$8,250,000
Siesta Key, FL
4 br, 6 ba, 5,079 ft², Single Family Home Residential
Price:
$8,250,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
327 DOM
Type:
Single Family Home
Beds:
4 br,
Baths:
6 ba
Subdiv:
Siesta Rev Of
SqFt:
5,079 SqFt

One-of-a-kind Beachfront Parcel On Siesta Key. 2.4 Acres With 264ft Directly On The Beach. Wester...

Photo of Listing #A4158589

Tucked Away On North S...

$5,750,000
Siesta Key, FL
6 br, 9 ba, 7,376 ft², Single Family Home Residential
Price:
$5,750,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
111 DOM
Type:
Single Family Home
Beds:
6 br,
Baths:
9 ba
Subdiv:
Siesta Rev Of
SqFt:
7,376 SqFt

Tucked Away On North Siesta Key, This Gated Estate On Deep Boating Water Is A Superb Expression O...

Photo of Listing #A4176892

The Style: Pure Palm B...

$5,495,000
Siesta Key, FL
4 br, 5 ba, 8,571 ft², Single Family Home Residential
Price:
$5,495,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
373 DOM
Type:
Single Family Home
Beds:
4 br,
Baths:
5 ba
Subdiv:
Cocoanut Bayou
SqFt:
8,571 SqFt

The Style: Pure Palm Beach. The Setting: Sun-soaked Siesta Key. This Flawlessly Accomplished Wate...

Photo of Listing #A4179706

Gorgeous Waterfront Es...

$4,988,000
Siesta Key, FL
4 br, 5 ba, 4,931 ft², Single Family Home Residential
Price:
$4,988,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
177 DOM
Type:
Single Family Home
Beds:
4 br,
Baths:
5 ba
Subdiv:
Siesta Rev Of
SqFt:
4,931 SqFt

Gorgeous Waterfront Estate Offering Sweeping Views From Big Pass To Bayou Louise! Rarely Availabl...

Photo of Listing #A4171152

This Is Siesta Key's "...

$3,950,000
Siesta Key, FL
6 br, 8 ba, 7,648 ft², Single Family Home Residential
Price:
$3,950,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
21 DOM
Type:
Single Family Home
Beds:
6 br,
Baths:
8 ba
Subdiv:
Ocean View
SqFt:
7,648 SqFt

This Is Siesta Key's "villa Ipanema" Built In 2001-2002 This Home Was Inspired By A Similar Itali...

Photo of Listing #A4185775

Paradise Found On Sies...

$3,599,000
Siesta Key, FL
4 br, 5 ba, 5,312 ft², Single Family Home Residential
Price:
$3,599,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
429 DOM
Type:
Single Family Home
Beds:
4 br,
Baths:
5 ba
Subdiv:
Ocean View
SqFt:
5,312 SqFt

Paradise Found On Siesta Key! This Fabulous Contemporary Designed Home Including A 1bed/1ba Priva...

Photo of Listing #A4149728

Bay Breezes From This ...

$3,295,000
Siesta Key, FL
4 br, 5 ba, 5,011 ft², Single Family Home Residential
Price:
$3,295,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
37 DOM
Type:
Single Family Home
Beds:
4 br,
Baths:
5 ba
Subdiv:
Siesta Beach
SqFt:
5,011 SqFt

Bay Breezes From This Spectacular Renovated And Expanded Siesta Key Luxury Home. Situated On Dee...

Photo of Listing #A4184343

Incredible North Siest...

$3,099,000
Siesta Key, FL
4 br, 4 ba, 4,103 ft², Single Family Home Residential
Price:
$3,099,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
271 DOM
Type:
Single Family Home
Beds:
4 br,
Baths:
4 ba
Subdiv:
Bay Island Shor
SqFt:
4,103 SqFt

Incredible North Siesta Key Pool Home With Bay Views And Protected Deep Water Boat Basin. This Ho...

Photo of Listing #A4162146

Coastal Design And Arc...

$2,999,000
Siesta Key, FL
5 br, 6 ba, 5,980 ft², Single Family Home Residential
Price:
$2,999,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
468 DOM
Type:
Single Family Home
Beds:
5 br,
Baths:
6 ba
Subdiv:
Royal Palm Harb
SqFt:
5,980 SqFt

Coastal Design And Architecture Sitting Perfectly Among Old Oaks On The North End Of Siesta Key. ...

Photo of Listing #A4145410

Delight In Serene Bayf...

$2,995,000
Siesta Key, FL
6 br, 7 ba, 6,812 ft², Single Family Home Residential
Price:
$2,995,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
215 DOM
Type:
Single Family Home
Beds:
6 br,
Baths:
7 ba
Subdiv:
Hidden Harbor
SqFt:
6,812 SqFt

Delight In Serene Bayfront Living At This Wonderfully Spacious Six-bedroom Estate, Just Minutes F...

Photo of Listing #A4167124

Just Move In And Start...

$2,250,000
Siesta Key, FL
4 br, 4 ba, 7,019 ft², Single Family Home Residential
Price:
$2,250,000
Waterfrontage
Waterview
City:
Siesta Key
DOM:
558 DOM
Type:
Single Family Home
Beds:
4 br,
Baths:
4 ba
Subdiv:
Siesta Beach
SqFt:
7,019 SqFt

Just Move In And Start Enjoying The Gracious Home. Sarasota’s Signature Barrier Island, Siesta Ke...

Photo of Listing #A4169014

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on May 28th, 2017 at 9:33pm EDT.

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