Waterfront single family homes with sailboat access to Charlotte Harbor, Pine Island Sound, the ICW, the Gulf of Mexico and beyond.
565 GREEN DOLPHIN DRIVE S
PLACIDA FL 33946
Residential / Single Family Residence
5 Bed · 5 Bath · 5,328 SqFt · $1,117/SqFt
Days on Market: 350
County: Charlotte
Subdiv/Community Name: Cape Haze
Legal Subdivision Name: CAPE HAZE SUB
Year built: 2021
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Compelling New Price! Magnificent 5 bedroom, 5 bath waterfront estate with over 5,300 sq.ft. in the historic waterfront neighborhood of Cape Haze offers mesmerizing panoramic views in every direction and superb boating access. Built in 2021 the luxury home sits on maybe the most spectacular waterfront site in the area. The property is nearly a full acre and is surrounded by Pelican Bay and the Intracoastal Waterway with over 350 feet of seawall and excellent dockage opportunities. Permitting is in progress for twin 50' long docks for vessels with 14'10'' beams (attached site plan). And endless other dock ... Read more....»
5132 JUNGLE PLUM ROAD
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 6,928 SqFt · $864/SqFt
Days on Market: 374
County: Sarasota
Subdiv/Community Name: Hidden Harbor
Legal Subdivision Name: HIDDEN HARBOR
Year built: 2008
Garage: Yes 10 vehicles
Private Pool: Yes
Waterfront: Yes — Canal - Saltwater
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....»
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 — Bay/Harbor
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....»
3300 CASEY KEY ROAD
NOKOMIS FL 34275
Residential / Single Family Residence
4 Bed · 4 Bath · 4,350 SqFt · $1,448/SqFt
Days on Market: 96
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 2005
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
This captivating Gulf-to-Bay residence is the epitome of timeless coastal elegance. Begin your mornings on the lanai, coffee in hand, as the sun rises over the Intracoastal Waterway. Spend your days boating from the private bayside dock and your evenings on your stretch of sandy beach, where spectacular Gulf sunsets are a nightly ritual. Inside, expansive light-filled interiors frame breathtaking water views in nearly every room. The main living area enjoys bay and beach vistas, while a beachside family room and generously sized guest bedrooms easily accommodate king-sized furnishings. The kitchen is designed as a gathering place, complete with abundant ... Read more....»
3240 CASEY KEY ROAD
NOKOMIS FL 34275
Residential / Single Family Residence
5 Bed · 4 Bath · 5,765 SqFt · $1,110/SqFt
Days on Market: 7
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1978
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Experience true Florida coastal living in this impeccably maintained Key West–style home on Casey Key, offering the rare and coveted Gulf-to-Bay lifestyle. Thoughtfully designed with high ceilings and a bright, open feel, this residence blends relaxed island charm with modern updates throughout. Step outside to a beautifully landscaped, fenced, and gated backyard—your own private oasis. Enjoy the Pebble Tec resurfaced pool, perfect for entertaining or unwinding after a day on the water. Boaters will love the new composite dock with covered lift, providing effortless access to the bay and Gulf beyond. The dune walkover and 100 feet of ... Read more....»
290 N WASHINGTON DRIVE
SARASOTA FL 34236
Residential / Single Family Residence
5 Bed · 4 Bath · 6,799 SqFt · $1,021/SqFt
Days on Market: 359
County: Sarasota
Subdiv/Community Name: Saint Armands Division John Ringling Estates
Legal Subdivision Name: SAINT ARMANDS DIV JOHN RINGLING ESTATES
Year built: 2008
Garage: Yes 6 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
A boater's dream and RARE opportunity—One of just 39 homes on this EXCLUSIVE side of St. Armands Circle offering -DIRECT GULF ACCESS- NO FIXED BRIDGES - and NO OBSTACLES. True deep-water dockage that comfortably accommodates a vessel over 60 feet. Enjoy full waterfront views of Sarasota Bay and the iconic downtown Sarasota skyline from every north-facing room in this home. This stunning, gated waterfront estate showcases the timeless elegance of Mediterranean architecture, blending classical design with refined coastal living. Expertly engineered with solid poured concrete walls reinforced by structural steel beams, this residence offers unmatched strength, integrity, and long-term value—an ideal foundation ... Read more....»
2116 CASEY KEY ROAD
NOKOMIS FL 34275
Residential / Single Family Residence
4 Bed · 3 Bath · 5,590 SqFt · $1,251/SqFt
Days on Market: 89
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1984
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes — Bay/Harbor
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....»
350 S SHORE DRIVE
SARASOTA FL 34234
Residential / Single Family Residence
5 Bed · 6 Bath · 5,099 SqFt · $1,467/SqFt
Days on Market: 12
County: Sarasota
Subdiv/Community Name: Sapphire Shores
Legal Subdivision Name: SAPPHIRE SHORES RESUB
Year built: 1996
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Imagine owning one of Sarasota Bay’s most exciting waterfront properties, where panoramic views, deep water access, and resort-style living create the kind of lifestyle people dream about but rarely find. Set on an oversized 2/3-acre lot with 172 feet of direct bay frontage, this fully renovated Sapphire Shores estate was redesigned for unforgettable entertaining and vibrant coastal living. Enjoy breathtaking panoramic views stretching across Sarasota Bay from Downtown city lights to Longboat Key, a 100-foot deep water dock with dual lifts 10,000 and 15,000 lbs, brand new seawall, resort-style pool and new spa, outdoor kitchen, multiple expansive decks, and a ... Read more....»
5179 HIDDEN HARBOR ROAD
SARASOTA FL 34242
Residential / Single Family Residence
6 Bed · 6 Bath · 4,900 SqFt · $1,531/SqFt
Days on Market: 228
County: Sarasota
Subdiv/Community Name: Hidden Harbor
Legal Subdivision Name: HIDDEN HARBOR
Year built: 2026
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Pre-Construction. To be built. Welcome to this newly imagined Siesta Key residence, a world curated for those with a sophisticated palate for modern architecture at the edge of the sea. Here, light dances across water and peers through your windows blending luxury, privacy and resort-style living within the exclusive enclave of Hidden Harbor. The journey begins as you approach this designer estate—a vision of coastal modernism, 4,900 square feet under air and meticulously crafted by TDI Coastal Homes, celebrated for precision, integrity, and elegance. Clean lines and natural textures blend with lush tropical surroundings, setting the stage for a life ... Read more....»
560 HARBOR COVE CIRCLE
LONGBOAT KEY FL 34228
Residential / Single Family Residence
3 Bed · 3 Bath · 3,485 SqFt · $2,267/SqFt
Days on Market: 198
County: Sarasota
Subdiv/Community Name: Bay Isles
Legal Subdivision Name: BAY ISLES
Year built: 1981
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
An exceedingly rare offering within the exclusive Bay Harbour enclave of Bay Isles on Longboat Key, this extraordinary peninsula estate delivers exceptional privacy, dramatic Sarasota Bay views, and direct boating access to both the Intracoastal Waterway and the Gulf of Mexico. Positioned at the end of a quiet cul-de-sac on a three-sided waterfront peninsula, the property features two private docks with water and electric, including one with a 15,000-lb lift designed for easy access. The Gulf is reachable through the nearby jetty with drawbridge, with an additional route via the John Ringling Bridge. The seawall was newly capped in 2020, ... Read more....»
4511 BAY SHORE ROAD
SARASOTA FL 34234
Residential / Single Family Residence
6 Bed · 6 Bath · 5,812 SqFt · $1,376/SqFt
Days on Market: 67
County: Sarasota
Subdiv/Community Name: Indian Beach
Legal Subdivision Name: INDIAN BEACH
Year built: 1928
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Lot Size (in acres): 1.10
Nestled on 1.1 acres of pristine bayfront along Sarasota Bay, Etowah stands as a timeless icon of Sarasota’s rich architectural heritage, offering sweeping, wide-open bay views to the north and south, from the manicured lawn at the water’s edge all the way to the distant skyline of downtown Sarasota, with glowing sunset views that unfold nightly across the horizon. Originally built in 1925, this distinguished two-story Mediterranean Revival estate spans over 6,500 square feet and commands captivating views across the bay, all while being just 10 minutes from downtown Sarasota. Following an extensive year-long restoration, Etowah has been meticulously renewed ... Read more....»
3950 RED ROCK WAY
SARASOTA FL 34231
Residential / Single Family Residence
5 Bed · 5 Bath · 6,850 SqFt · $1,168/SqFt
Days on Market: 228
County: Sarasota
Subdiv/Community Name: Red Rock Terrace
Legal Subdivision Name: RED ROCK TERRACE
Year built: 2026
Garage: Yes 5 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Pre-Construction. To be built. Why choose between your perfect sanctuary and stunning sunsets when you can have both. Every evening, the horizon performs a breathtaking masterpiece and from your private terrace at 3950 Red Rock Way, you hold the best seat in the house. Set upon a rare half-acre waterfront lot with 50 feet of frontage on Roberts Bay, this 6,850-square-foot modern coastal estate captures the essence of Sarasota luxury: enchanting artistry, seductive serenity, and a seamless connection to water and light. This new-construction residence, designed for those who refuse to compromise beauty for function, rises with quiet confidence above ... Read more....»
1249 S BASIN LANE
SARASOTA FL 34242
Residential / Single Family Residence
6 Bed · 6 Bath · 10,642 SqFt · $841/SqFt
Days on Market: 20
County: Sarasota
Subdiv/Community Name: Siesta Properties Inc
Legal Subdivision Name: SIESTA PROPERTIES INC
Year built: 1951
Garage: Yes 8 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Lot Size (in acres): 1.57
Rarely does a property of this caliber become available on Siesta Key. Spanning approximately 1.6 acres, this exceptional waterfront estate is framed by majestic oak trees and lush, mature landscaping, creating a private, quiet, and timeless retreat. This legacy property showcases expansive bayfront views that wrap gracefully around to a protected canal, offering both breathtaking vistas and sheltered water access. At its heart stands a classic and formal Southern-style residence, remodeled in 2008, rich in character and designed for an elegant lifestyle. Grand, beautifully proportioned rooms are designed for effortless entertainment, highlighted by a stately formal dining room worthy of ... 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 — Bay/Harbor
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....»
740 N MANASOTA KEY ROAD
ENGLEWOOD FL 34223
Residential / Single Family Residence
4 Bed · 6 Bath · 7,515 SqFt · $1,317/SqFt
Days on Market: 17
County: Sarasota
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: MANASOTA KEY
Year built: 2018
Garage: Yes 9 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Lot Size (in acres): 1.12
Where the first light of dawn shimmers across the Intracoastal and the glow of sunset melts into the Gulf, this is a once-in-a-generation Gulf-to-Bay estate of uncompromising beauty and distinction. Gracefully positioned on approximately 1.1 acres along the gated north end of Manasota Key, this masterfully curated waterfront compound embodies refined coastal living with private beach access and a bayfront dock and lift. The property offers a balance of serenity and an elevated boating lifestyle. Expertly built by KIMCO and created by Suncoast, the main residence spans 5,839 sf of living space, and the guest house offers 1676 sf. Constructed ... Read more....»
1216 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 6 Bath · 8,050 SqFt · $1,335/SqFt
Days on Market: 311
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1999
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Lot Size (in acres): 1.10
This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water ... Read more....»
14 GROUPER HOLE DRIVE
BOCA GRANDE FL 33921
Residential / Single Family Residence
5 Bed · 5 Bath · 6,207 SqFt · $1,744/SqFt
Days on Market: 112
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 — Intracoastal Waterway
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. ROOF 2017. 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. ... Read more....»
4123 BAY SHORE ROAD
SARASOTA FL 34234
Residential / Single Family Residence
5 Bed · 6 Bath · 5,117 SqFt · $2,300/SqFt
Days on Market: 23
Cumulative Days on Market: 322
County: Sarasota
Subdiv/Community Name: Indian Beach
Legal Subdivision Name: INDIAN BEACH MAP OF
Year built: 2021
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Lot Size (in acres): 1.07
A modern masterpiece on Sarasota Bay, this architectural landmark embodies contemporary design and sustainable luxury. Set on over an acre in the prestigious Indian Beach neighborhood—Sarasota’s renowned “Museum Area”—the gated estate boasts nearly 180 feet of waterfront with panoramic views that extend endlessly across the Bay. Conceived by acclaimed architect Mark Sultana of DSDG and expertly built by Voigt Brothers, the elevated residence rests gracefully on monumental columns, appearing to float above the landscape. Open-air colonnades below provide serene shaded spaces and complete storm protection, while the reinforced concrete structure—including the roof—ensures enduring strength. Elegant wood accents and striking architectural details ... Read more....»
3550 BAYOU LOUISE LANE
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 4,325 SqFt · $2,751/SqFt
Days on Market: 95
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 — Gulf/Ocean to Bay
Pre-Construction. To be built. The lot is also available as vacant land (MLS #A4682294) ($6.7M). 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 ... Read more....»
1290 HIDDEN HARBOR WAY
SARASOTA FL 34242
Residential / Single Family Residence
5 Bed · 5 Bath · 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 — Canal - Saltwater
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....»
4315 MANGROVE PLACE
SARASOTA FL 34242
Residential / Single Family Residence
6 Bed · 6 Bath · 7,535 SqFt · $1,924/SqFt
Days on Market: 249
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 — Bay/Harbor
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....»
1310 S LAKE SHORE DRIVE
SARASOTA FL 34231
Residential / Single Family Residence
4 Bed · 4 Bath · 10,697 SqFt · $2,468/SqFt
Days on Market: 59
County: Sarasota
Subdiv/Community Name: Oyster Bay Estates
Legal Subdivision Name: OYSTER BAY ESTATES
Year built: 1992
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes — Intracoastal Waterway
Lot Size (in acres): 1.22
Welcome to Villa Meraviglia - A Home Beyond Imagination. An extraordinary Neo-Classical Italian Renaissance Estate set on 1.22 bayfront acres in Sarasota’s exclusive Oyster Bay Estates. Featuring 146 feet of pristine, direct frontage along the sparkling waters of Little Sarasota Bay, where sweeping panoramic views unfold, this walled and gated estate feels like a grand villa on the shores of Lake Como. A bold metallic gate, crowned with a striking Medusa head, sets the tone for the arrival experience, while two additional gold leafed gates - each equipped with electromagnetic openers - provide secure access, including a private entry to ... 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.
