Waterfront single family homes with sailboat access to Charlotte Harbor, Pine Island Sound, the ICW, the Gulf of Mexico and beyond.
16 GROUPER HOLE DRIVE
BOCA GRANDE FL 33921
Residential / Single Family Residence
3 Bed · 3 Bath · 3,317 SqFt · $1,807/SqFt
Days on Market: 8
County: Charlotte
Complex/CommunityName: EAST SHORE ACRES
Subdiv/Community Name: East Shores Acres
Legal Subdivision Name: EAST SHORE ACRES
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Private custom designed home with deepwater protected dockage on a lot and a half (150’) — situated directly across from the Boca Grande Club! This exquisite 3-bedroom, 3-bathroom BIG VIEW waterfront Estate Property is a 1996 National award winning architectural design, set within a lush tropical oasis with rich verdant greenery and mature native landscaping. Incredible and expansive views front Gasparilla Sound and the ICW, additionally with multiple decks facing East and West with over 4,000 sq. ft. under roof! The main level features an open-concept layout ideal for effortless entertaining, seamlessly connecting the kitchen, dining, and living areas, boasting ... Read more....»
5132 JUNGLE PLUM ROAD
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 6,928 SqFt · $924/SqFt
Days on Market: 208
County: Sarasota
Subdiv/Community Name: Hidden Harbor
Legal Subdivision Name: HIDDEN HARBOR
Year built: 2008
Garage: Yes 10 vehicles
Private Pool: Yes
Waterfront: Yes
Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living ... Read more....»
2116 CASEY KEY ROAD
NOKOMIS FL 34275
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 5,590 SqFt · $1,251/SqFt
Days on Market: 19
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1984
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Gulf-to-Bay estate on Casey Key offering rare, deeded private beach access a few steps from the front door and deep-water frontage on Blackburn Bay. Set on more than a half-acre, this elevated coastal residence spans more than 5,500 square feet and delivers a true dual-waterfront lifestyle with boating on one side and the Gulf of Mexico on the other. The bayfront setting is designed for outdoor living and entertaining, featuring a multi-level tropical environment with expansive pavered decks, covered lounge areas, a gazebo dining space with fully equipped summer kitchen and built-in grilling station, and an open pool terrace with heated ... Read more....»
5215 HIDDEN HARBOR ROAD
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 4,863 SqFt · $1,625/SqFt
Days on Market: 77
County: Sarasota
Subdiv/Community Name: Hidden Harbor
Legal Subdivision Name: HIDDEN HARBOR
Year built: 2025
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
One or more photo(s) has been virtually staged. Under Construction. This brand-new waterfront estate is being brought to life by Dynan Construction, Sarasota’s premier local luxury builder celebrated for impeccable craftsmanship, architectural integrity, and enduring coastal design. Built to the Fortified Gold Standard, the residence is engineered for long-term resilience against Florida’s coastal elements while embodying the artistry and refinement that define Dynan’s signature builds. Interiors are curated by acclaimed designer Annalise O’Brien, ensuring every space reflects elevated taste and timeless sophistication. This 5-bedroom estate features 5 full baths plus a dedicated pool bath and powder bath, offering a rare ... Read more....»
65 LIGHTHOUSE POINT DRIVE
LONGBOAT KEY FL 34228
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,921 SqFt · $1,625/SqFt
Days on Market: 20
County: Sarasota
Subdiv/Community Name: Lighthouse Point
Legal Subdivision Name: LIGHTHOUSE POINT
Year built: 2001
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 15,898.00
Longboat Key Waterfront Estate Lifestyle Unrivaled in privacy, craftsmanship, and waterfront lifestyle, this gated Lighthouse Point residence lives like a grand coastal estate, with 4 Bedrooms, 4-1/2 Baths, and nearly 5,000 square feet of refined interiors opening to sweeping terraces on two levels and serene views over a secluded, bridgeless-access lagoon leading directly to the Gulf of Mexico. Extensively renovated in 2021, the two-story Mediterranean-inspired home blends timeless architecture with a sophisticated contemporary aesthetic, framed by manicured tropical grounds on over one-third of an acre in one of Longboat Key’s most exclusive enclaves. Dramatic Arrival & Entertaining Spaces A soaring central foyer with ... Read more....»
1500 BAYVIEW DRIVE
SARASOTA FL 34239
Residential / Single Family Residence
5 Bed · 5 Bath · 4,031 SqFt · $2,419/SqFt
Days on Market: 17
County: Sarasota
Subdiv/Community Name: Bay View Heights
Legal Subdivision Name: BAY VIEW HEIGHTS ADD
Year built: 2017
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Nestled in the heart of Sarasota, Florida, "The Seathrough House" stands as a testament to timeless elegance and modern sophistication. Designed by the acclaimed architectural firm Sweet Sparkman and meticulously crafted by builder Josh Wynne, this mid-century marvel redefines luxury living. From the moment you step inside, the panoramic bay views captivate the senses, seamlessly blending the indoors with the breathtaking natural beauty of the surroundings. Every room boasts expansive windows, offering an uninterrupted vista of Sarasota Bay that is nothing short of mesmerizing. This architectural masterpiece features five bedrooms and five baths, providing ample space for both relaxation and ... Read more....»
14 GROUPER HOLE DRIVE
BOCA GRANDE FL 33921
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 6,207 SqFt · $1,744/SqFt
Days on Market: 71
County: Charlotte
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: EAST SHORE ACRES
Year built: 1997
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
2 DEEP-WATER DOCKS AND A COVERED 7,000 LB LIFT. 5 BEDROOMS AND 5.5 BATHROOMS. MYRTHA POOL. INDOOR GUN RANGE. NO FIXED BRIDGES TO GULF WATERS. Welcome to a true Sportsman’s Paradise at 14 Grouper Hole Drive on Gasparilla Island in Boca Grande, Florida. This exceptional waterfront estate offers an unparalleled lifestyle, where breathtaking views of the Gasparilla Sound greet you the moment you step through the grand double doors. Designed for both adventure and relaxation, this residence seamlessly blends refined elegance with world-class amenities. The main living area is on the second floor, accessible by a three-stop elevator. A bright ... Read more....»
1290 HIDDEN HARBOR WAY
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 3 Half Baths · 6,079 SqFt · $1,970/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Hidden Harbor
Legal Subdivision Name: HIDDEN HARBOR ADD
Year built: 2026
Garage: Yes 5 vehicles
Private Pool: Yes
Waterfront: Yes
Under Construction. Introducing one of Hidden Harbor’s most significant new offerings—a waterfront estate meticulously crafted by Dynan Construction Co. one of Sarasota’s most respected and sought-after luxury builders. Known for their uncompromising standards, Fortified Gold engineering, and elite coastal construction methods, Dynan Construction Co. has earned a prestigious reputation across Florida for delivering residences that marry innovative design with enduring structural integrity. This home represents a rare level of elevated coastal living, where artistry and engineering come together in flawless harmony. This bay front property’s unique footprint extends across to a deep saltwater canal, allowing unobstructed panoramic Bay views while ... Read more....»
3550 BAYOU LOUISE LANE
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,325 SqFt · $2,820/SqFt
Days on Market: 2
County: Sarasota
Subdiv/Community Name: Siesta Rev
Legal Subdivision Name: SIESTA REV OF
Year built: 2027
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Pre-Construction. To be built. The lot is also available as vacant land (MLS #A4682294). Introducing the Miller Floorplan designed by award winning Konstant Architecture (plans complete and available), a to be built waterfront estate set on one of the most extraordinary parcels on the north end of Siesta Key, one of only 10 properties with water access on the east and west. This award-winning luxury custom build plan is the example of architectural excellence at the highest level. Positioned on over three quarters of an acre with 175 feet of pristine water frontage, this rare offering captures sweeping panoramic views from ... Read more....»
4315 MANGROVE PLACE
SARASOTA FL 34242
Residential / Single Family Residence
6 Bed · 6 Bath · 3 Half Baths · 7,535 SqFt · $1,924/SqFt
Days on Market: 221
County: Sarasota
Subdiv/Community Name: South Cocoanut Bayou
Legal Subdivision Name: SOUTH COCOANUT BAYOU
Year built: 2005
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Private Island, Gated Home, Private access to deeded beach! Experience the epitome of exclusivity with unheard of waterfront views, unmatched privacy, and breathtaking, expansive vistas from your own private island retreat. Tucked away on a private island in Siesta Key’s South Cocoanut Bayou, this Tuscan-inspired estate feels like it’s been plucked from the pages of a storybook. The estate at 4315 Mangrove Place features a Tuscan-inspired central courtyard with over 4000 sq ft designed as the heart of the home. It is a grand, open-air courtyard enclosed by both the main residence and the guest villa, connected via an elegant, ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.
