Waterfront single family homes with sailboat access to Charlotte Harbor, Pine Island Sound, the ICW, the Gulf of Mexico and beyond.
1415 BAYSHORE DRIVE
ENGLEWOOD FL 34223
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 3,487 SqFt · $531/SqFt
Days on Market: 76
County: Sarasota
Subdiv/Community Name: Englewood Gardens
Legal Subdivision Name: ENGLEWOOD GARDENS
Year built: 2003
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.08
This exceptional custom estate sits on over an acre of lush, landscaped grounds overlooking the tranquil waters of Forked Creek. Designed to capture the essence of coastal living, it offers the perfect blend of privacy, natural beauty, and refined comfort. The tropical grounds feature coconut palms, banana trees, multiple mango varieties, olive trees, and more—creating an inviting oasis. A heated pool, spacious fire pit, and expansive entertaining areas provide the ideal setting for lively gatherings, breathtaking sunsets, or quiet evenings under the stars. With a private boat lift and two jet ski lifts, you’re minutes from Lemon Bay, the Intracoastal, and ... Read more....»
10580 POUGHKEEPSIE CIRCLE
PORT CHARLOTTE FL 33981
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 5,206 SqFt · $384/SqFt
Days on Market: 112
County: Charlotte
Complex/CommunityName: PORT CHARLOTTE
Subdiv/Community Name: Port Charlotte
Legal Subdivision Name: PORT CHARLOTTE SEC 87
Year built: 2009
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Live the Luxury Coastal lifestyle with this STUNNING SAILBOAT ACCESS 4 Bedroom, 4.5 Bathroom, 2 Car attached Garage & a 2 Car detached garage, TWO-STORY, Pool home with a Den, Family & Bonus rooms. Situated on a DOUBLE TIP Lot with 255ft of water frontage, a Wood dock & 16,000-lb boat lift, South Gulf Cove. Boasting over 5,200 square feet of living space, this home is bathed in natural light from expansive windows and offers BEAUTIFUL water views throughout, blending comfort, elegance, and scenic beauty. The living room impresses with soaring tray ceilings and breathtaking views, seamlessly connected to a ... Read more....»
4024 CASEY KEY ROAD
NOKOMIS FL 34275
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 4,347 SqFt · $541/SqFt
Days on Market: 303
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: ACREAGE & UNREC
Year built: 1979
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
BACK ON MARKET. CASEY KEY HOME RUN INVESTMENT! MOTIVATED SELLERS HAVE REDUCED. STORM RESISTANT Waterfront Residence on Casey Key, one of the most exclusive barrier islands on Florida’s West Coast! Looking for a waterfront residence MOVE-IN READY, with a deep-water dock, completely unaffected by the recent storms; & located on a magical Island that has no high rises, no traffic jams, exclusivity, resident-owned beaches, privacy, great medical, dining, and shopping, all extremely convenient? This Casey Key estate with over 4300 square feet of living space offers a rare combination of privacy & location, with stunning views of Little Sarasota ... Read more....»
21321 HARBORSIDE BOULEVARD
PORT CHARLOTTE FL 33952
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 6,484 SqFt · $384/SqFt
Days on Market: 332
County: Charlotte
Complex/CommunityName: GRASSY POINT ESTATES
Subdiv/Community Name: Grassy Point Estates
Legal Subdivision Name: GRASSY POINT ESTATES
Year built: 2008
Garage: Yes 6 vehicles
Private Pool: Yes
Waterfront: Yes
Live the LUXURY lifestyle with this Mediterranean style 5 bedroom, 5 1/2 bath, 6 Car garage home located in the upscale private deed restricted community of Grassy Point Yacht Club. Grassy Point is a WATERFRONT GATED COMMUNITY featuring 24 HOUR MANNED SECURITY, DEEDED DOCKS with a PRIVATE MARINA, DEEP WATER BASIN, CLUBHOUSE AND MUCH MORE! All docks are within OPEN WATERS with NO BRIDGES. Built-in 2008, this STUNNING two-story home boasts over 6400 square feet of living space with tile & wood flooring throughout, crown molding, tray & coffered ceilings, a working elevator, and SO MUCH MORE! French doors open ... Read more....»
300 GARDEN LANE
SARASOTA FL 34242
Residential / Single Family Residence
4 Bed · 4 Bath · 3,256 SqFt · $998/SqFt
Days on Market: 2
County: Sarasota
Subdiv/Community Name: Bay Island
Legal Subdivision Name: SIESTA REV OF
Year built: 1975
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
A Rare Opportunity on North Siesta Key – 350 Feet of Waterfront! Discover this unique single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—is truly a boater’s and fisherman’s paradise, just steps from Shell Beach and its breathtaking sunsets. The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom ... Read more....»
12400 PLACIDA ROAD
PLACIDA FL 33946
Residential / Single Family Residence
5 Bed · 3 Bath · 2 Half Baths · 3,968 SqFt · $1,046/SqFt
Days on Market: 42
County: Charlotte
Subdiv/Community Name: Placida Sub
Legal Subdivision Name: PLACIDA
Year built: 2003
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.75
Architect-designed and comprehensively restored, this contemporary waterfront estate on Placida Harbor offers bold design, structural integrity, and over $1M in premium upgrades. Originally created by architect Howard Holtzman and built by BCB Homes of Naples, the home was constructed with concrete and steel for lasting strength and peace of mind—just minutes from Boca Grande. Walls of impact-rated glass frame panoramic views and open to elevated terraces, a vanishing-edge pool, raised spa, and lush landscaping. The interior showcases refinished Brazilian cherry floors, restored stainless steel countertops, elevated outlets, and designer lighting. A custom stainless kitchen by Varenna & Foster features Sub-Zero, Miele, ... Read more....»
614 BAYSHORE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 4 Bath · 1 Half Bath · 4,048 SqFt · $1,359/SqFt
Days on Market: 20
County: Sarasota
Subdiv/Community Name: Bay Acres Sub
Legal Subdivision Name: BAY ACRES - RESUB
Year built: 2024
Garage: Yes 5 vehicles
Private Pool: Yes
Waterfront: Yes
Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand-new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted by sweeping water views and spectacular Casey Key sunsets, setting the stage for an extraordinary lifestyle. Designed for the boating connoisseur, the property boasts a new dock with water, electric, a 20,000 lb boat lift, and direct bay access—no bridges to the Gulf. For the automotive enthusiast, a 1,400 sq. ft. climate-controlled garage with 14-ft ceilings, professional-grade car lifts, epoxy floors, perfect showcase for your collection. Inside, the home ... Read more....»
5727 RIEGELS POINT ROAD
SARASOTA FL 34242
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 3,616 SqFt · $1,546/SqFt
Days on Market: 353
County: Sarasota
Subdiv/Community Name: Riegels Landing
Legal Subdivision Name: RIEGELS LANDING
Year built: 1982
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
When home feels like a permanent vacation, every day becomes a tropical escape where time slows down, the water is always nearby, and every day begins and ends with a coastal breeze. That’s the essence of 5727 Riegels Point—a casually luxurious, resort-style property where the lifestyle is as effortless as it is extraordinary. Nestled within the gated enclave of Riegels Landing on Siesta Key, an exclusive community with fewer than 30 estate homes, this unique property offers a lifestyle where outdoor living is as exceptional as the interior. Step into your own island sanctuary, surrounded by 357 feet of deep-water ... Read more....»
749 FREELING DRIVE
SARASOTA FL 34242
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 6,827 SqFt · $872/SqFt
Days on Market: 241
County: Sarasota
Complex/CommunityName: BAY ISLAND SHORES
Subdiv/Community Name: Bay Island Shores
Legal Subdivision Name: BAY ISLAND SHORES
Year built: 1997
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Experience coastal elegance and ultimate island living in this extraordinary gated waterfront estate, Casa della Fontana, the Fountain House. This home offers the ideal blend of luxury, privacy, and convenience on a tranquil street on Siesta Key's coveted north end. Just minutes from everything on and off the island, this residence is poised on a deep sailboat water bayou just off Sarasota Bay and the Intracoastal Waterway. Enjoy a quick boat ride through Big Pass to the Gulf of Mexico, making it a haven for boating enthusiasts. The heart of this magnificent property is the great room, offering tranquil water ... Read more....»
5132 JUNGLE PLUM ROAD
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 6,928 SqFt · $996/SqFt
Days on Market: 112
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....»
3441 GULFMEAD DRIVE
SARASOTA FL 34242
Residential / Single Family Residence
6 Bed · 6 Bath · 1 Half Bath · 4,769 SqFt · $2,202/SqFt
Days on Market: 41
County: Sarasota
Subdiv/Community Name: Gulfmead Estates
Legal Subdivision Name: GULFMEAD ESTATES
Year built: 2026
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Pre-Construction. To be built. This luxurious grand canal-front estate offers direct deep-water boating to the Gulf, out of one of the most exclusive neighborhoods on north Siesta Key. The upcoming new construction property by M&J Pham Development is on an expansive 17,842 SF and 0.41 acre lot, with a 4,769 SF traditional-style home to be built. Enjoy two separate guests suites on top of the two 2-car garages, for a total of 4 garage spaces, both with elevator access to the above suites. The master bedroom will have water views, and the grand entry home hosts a total of 6 ... Read more....»
4315 MANGROVE PLACE
SARASOTA FL 34242
Residential / Single Family Residence
6 Bed · 6 Bath · 3 Half Baths · 7,535 SqFt · $2,117/SqFt
Days on Market: 48
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
Experience the epitome of exclusivity with unheard of waterfront views, unmatched privacy, and breathtaking, expensive 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, covered breezeway. The main residence offers soaring ceilings, intricate ... 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.
