Sarasota Homes with Sailboat Water Water Frontage

Sarasota Homes with Sailboat Water Water Frontage

Welcome to Sarasota County, Florida, a stunning coastal gem known for its vibrant arts scene, pristine beaches, and a lifestyle that embraces both relaxation and adventure. Nestled along the Gulf Coast, Sarasota is a paradise for those who appreciate natural beauty, cultural richness, and an active outdoor lifestyle. With an average year-round temperature of 73 degrees, residents enjoy sun-drenched days and balmy evenings, perfect for exploring the many parks, trails, and waterfront activities that abound in the area.

One of the most sought-after features in Sarasota real estate is homes with sailboat water frontage. Imagine stepping out of your back door and onto your boat, ready to set sail on the shimmering waters of the Gulf of Mexico. These exceptional properties offer direct access to deep-water canals, making them ideal for boating enthusiasts and water lovers alike. Whether you’re looking to indulge in a leisurely afternoon of fishing, enjoy a sunset cruise, or simply bask in the tranquility of waterfront living, these homes provide the perfect backdrop for your aquatic adventures.

Sarasota's waterfront communities are renowned for their luxurious amenities, stunning architectural designs, and breathtaking views. From modern estates with private docks to charming bungalows nestled among lush tropical landscapes, there’s a home to suit every taste and lifestyle. Embrace the Sarasota way of life, where every day feels like a vacation, and the allure of sailboat water living is just a step away. Come explore the possibilities and discover your dream home in this enchanting coastal paradise!

Newest Sarasota Homes with Sailboat Water Water Frontage

5 Beds ⋅ 6 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. 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 from Big Pass to Bayou Louise. With unobstructed access to Sarasota Bay and the Gulf, boating enthusiasts can enjoy effortless days of fishing, cruising, or island hopping directly from their backyard. This is coastal living without compromise. Designed for both elevated beauty and resilience, the Miller Floorplan features approximately 4,325 square feet of conditioned living space with a raised main living level, private elevator access, and a multi-bay garage with dedicated boat storage below. The thoughtfully designed layout includes five bedrooms, five full bathrooms, and a powder room. The primary suite is privately positioned offering a spa-inspired bath with separate water closet, expansive closet space, and seamless connection to outdoor living. The heart of the home is an open-concept living and dining space anchored by a designer kitchen with pantry and butler’s area, all oriented toward breathtaking water views. Expansive porches, screened outdoor living areas, and a resort-style pool with integrated spa and swim-off areas create a true waterfront retreat. A standing seam metal roof and sophisticated coastal architectural detailing reflect timeless style while complementing the surrounding natural beauty. Located on the coveted north end of Siesta Key, this estate offers both privacy and convenience. The beach, boating, waterfront dining, and Sarasota’s vibrant cultural and entertainment scene are moments away. Large parcels of this caliber with 175 feet of frontage and water access on the east and west side of the property, are rarely available, making this an exceptional opportunity to secure a refined blend of modern luxury, prime location, and long-term value. Where coastal beauty, architectural sophistication, and thoughtful design converge, this residence delivers an unparalleled Siesta Key lifestyle.

3550 Bayou Louise Lane, Sarasota

4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Privately set on Palm Island in the heart of Siesta Key, this residence offers an exceptional combination of generous living space, thoughtful design and effortless access to the island’s most celebrated destinations. Just a short distance from the powdery, white quartz sands of Siesta Beach and the boutiques, dining and lively atmosphere of Siesta Village, this beautifully reimagined waterfront residence presents a rare opportunity to enjoy a relaxed coastal lifestyle without compromising comfort, privacy or quality. Nearly every aspect of the home was transformed, creating a fresh, modern interior, designed for both everyday living and gracious entertaining. Soaring ceilings, abundant natural light, a contemporary custom staircase and impact-rated windows and doors establish an open, airy atmosphere, while luxury vinyl and engineered hardwood flooring, recessed lighting, and thoughtfully integrated storage add warmth and architectural interest. The expansive kitchen serves as the centerpiece of the home, featuring custom cabinetry, stone countertops, upgraded stainless steel appliances, wine storage and an oversized quartz island with generous seating. Designed to accommodate everything from casual mornings to larger gatherings, the kitchen flows naturally into the surrounding living and dining spaces and continues outdoors to the pool, lawn, and waterfront beyond. The main-level primary suite provides a serene private retreat with direct access to the pool area, a spacious custom-fitted closet and a beautifully appointed spa-inspired bathroom. Three additional bedrooms offer comfortable accommodations for family and guests, while an upstairs, separate flex space is ideally suited for a private office, exercise room or personalized retreat. A sunroom and conveniently positioned pool bath further enhance the home’s easy indoor-outdoor connection. Outside, the property reveals one of its most distinctive features: an unusually spacious backyard for Siesta Key. A broad lawn surrounds the heated pool, creating room for outdoor dining, recreation, pets, and relaxed afternoons beneath the Florida sun. Beyond the pool, peaceful canal views and a private dock provide a tranquil waterfront setting with boating access. A well supplies the irrigation system, helping maintain the lush tropical landscape. A detached two-car garage offers valuable parking and additional storage for beach equipment, bicycles, paddleboards and other island essentials to enjoy the Siesta Key lifestyle. Morning walks along Siesta Beach, afternoons beside the pool and evenings dining in Siesta Village can all become part of everyday life. Spacious, extensively remodeled, and ideally positioned near the beach, Village and boating water, 430 Island Circle is a sophisticated, yet wonderfully comfortable island retreat designed for those who want to experience the very best of Siesta Key.

430 Island Circle, Sarasota

Roberts Point SubDv. ⋅ 34242 Zip Code

An exceptional opportunity to create a custom waterfront residence in one of North Siesta Key’s most desirable neighborhoods. Surrounded by substantial luxury homes, this property offers a peaceful bayou setting with direct water access to Sarasota Bay for motorized craft, kayaks and paddleboards. The site is enhanced by mature tropical landscaping and tranquil water views, providing an inviting natural backdrop for a thoughtfully designed new home. Multiple outdoor living areas, terraces and elevated gathering spaces could be incorporated to take full advantage of the waterfront setting and relaxed Siesta Key lifestyle. An existing residence currently occupies the property, offering flexibility for use, rental or renovation while future building plans are developed. The home includes a roof completed in August 2023, hurricane shutters and completed storm remediation; however, the property’s compelling value lies in its land, location and potential to build new within a neighborhood known for impressive coastal residences. Conveniently positioned on North Siesta Key, the property provides easy access to Siesta Beach, Siesta Village, downtown Sarasota, shopping, dining and entertainment. Whether envisioned as a full-time residence or private island retreat, this is a rare opportunity to design a home tailored to your lifestyle in an established waterfront community.

4114 Roberts Point Circle, Sarasota

4 Beds ⋅ 3 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code

Set along a quiet bayou in Roberts Point, one of North Siesta Key’s most coveted and established neighborhoods, this well-cared-for waterfront residence offers an appealing combination of immediate livability, flexible space and exceptional future potential. Enjoy the home as it is, thoughtfully update it over time or create an entirely new island retreat among the neighborhood’s impressive luxury residences. The primary living spaces are positioned on the upper level, where vaulted ceilings and an open layout create a bright, comfortable setting for everyday living and entertaining. Multiple decks extend the living areas outdoors, offering peaceful views of the water and surrounding tropical landscape. A hot tub overlooking the bayou provides a relaxing place to unwind at the end of the day. The legal ground level (non-conforming) adds valuable versatility with a private bedroom and bath, bonus room, screened lanai and two-car garage—well suited for guests, extended family, a home office or recreational space. A new roof completed in August 2023, hurricane shutters and completed storm remediation provide added peace of mind. The property offers direct water access to Sarasota Bay for motorized craft, kayaks and paddleboards, making it easy to enjoy Siesta Key’s natural surroundings from your own backyard. Ideally located near Siesta Beach, Siesta Village, shopping, dining, and entertainment, and easy access to mainland Sarasota, this is a distinctive opportunity to live, renovate or rebuild in a coveted North Siesta Key setting.

4114 Roberts Point Circle, Sarasota

4 Beds ⋅ 4 Baths ⋅ Manasota Bay Estates SubDv. ⋅ 34223 Zip Code

Imagine waking each morning to the gentle shimmer of Lemon Bay, coffee in hand as the sun rises over the water and ending your evenings with your toes in the sand, watching the Gulf paint the sky in breathtaking shades of orange and pink. This is more than a home; it’s a lifestyle few ever experience. Hidden behind the gates of the exclusive North Manasota Key community, along a secluded two-mile private road, this extraordinary Gulf-to-Bay estate offers the rare privilege of living where boating adventures and beach days become part of your everyday routine. Here, privacy, luxury, and nature exist in perfect harmony. Spanning more than 3,400 square feet, this thoughtfully designed waterfront retreat offers four bedrooms and four bathrooms with expansive living spaces bathed in natural light. Walls of windows frame panoramic views of Lemon Bay, creating a seamless connection between the beauty outside and the comfort within. Every room invites you to slow down, breathe deeply, and savor the rhythm of coastal living. Step outside and discover your own slice of paradise. Jump on your boat from the private bayfront dock for a day exploring the waterways, spend the afternoon kayaking or paddleboarding through calm waters, or cast a line just steps from home. When the Gulf calls, your deeded private beach access is only 300 feet away via an exclusive 8-foot-wide walkway, making spontaneous sunset strolls and shelling adventures effortless. After a day on the water, retreat to the private Jacuzzi just outside the primary suite, where peaceful bay views provide the perfect backdrop to unwind beneath the stars. The expansive pressure-treated wood deck wraps the rear of the home, creating endless opportunities for outdoor dining, entertaining, or simply enjoying the soothing coastal breeze and abundant wildlife that make North Manasota Key so special. Designed with both elegance and peace of mind, the home has been meticulously updated with a durable 2020 metal roof, 2022 impact windows, hurricane protection for the sliding glass doors, three air conditioning systems, two water heaters, a 250-gallon propane tank, central vacuum system, and an oversized laundry room. The spacious garage easily accommodates vehicles, golf carts, kayaks, paddleboards, fishing gear, and all the essentials for your waterfront lifestyle. Whether you’re searching for a luxurious year-round residence, an unforgettable family retreat, or the ultimate waterfront escape, this remarkable Gulf-to-Bay property delivers an unparalleled Florida lifestyle. Here, every sunrise over Lemon Bay, every sunset on the Gulf, and every gentle sea breeze become daily reminders that you’ve found the place where others only dream of vacationing.

721 N Manasota Key Road, Englewood

3 Beds ⋅ 2 Baths ⋅ Brucewood Bayou SubDv. ⋅ 34223 Zip Code

Nestled on nearly one-half acre along the Intracoastal Waterway in Englewood, Florida, this beautifully renovated waterfront residence offers an exceptional blend of luxury, comfort, and coastal living. Encompassing 1,707 square feet under air, the home features three bedrooms, two bathrooms, and an oversized three-car garage, all thoughtfully designed to maximize both functionality and breathtaking water views. Extensively renovated with custom upgrades throughout to include wood cabinets, granite countertops, marble backsplash, pendant lighting, and over $25,000 in solar panels which is included free and clear; the property also offers peace of mind with a new roof, updated plumbing, and a new air conditioning system. The home's open and inviting layout seamlessly connects indoor and outdoor living spaces, creating the perfect setting for entertaining or simply enjoying the tranquil waterfront surroundings. Positioned to capture spectacular sunset views over the Intracoastal Waterway, this exceptional deep-water property provides direct Gulf access, making it an ideal retreat for boating enthusiasts and those seeking the ultimate Florida waterfront lifestyle. The expansive lot offers privacy and ample space for outdoor enjoyment, while the hurricane protection enhances energy efficiency and long-term value. Whether you're relaxing on the water's edge, heading out for a day on the Gulf, or enjoying an evening sunset from your own backyard, this remarkable Englewood waterfront home delivers a rare opportunity to experience the very best of Southwest Florida living. Make this your next home and enjoy easy access to beautiful beaches, shopping, and world class dining experiences. Call today to schedule your private tour.

211 Bahia Vista Drive, Englewood

2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code

Experience the best of Siesta Key living in this beautifully updated 2 bedroom, 2 bath condo on the 3rd floor of Sunrise Cove. Offered turnkey furnished, this inviting residence is ready for you to move right in and start enjoying the island lifestyle. ****Enjoy next-level comfort with a brand-new 2026 A/C system and LED whole-home in-duct air purifier a standout upgrade delivering cool, refreshing comfort and cleaner, fresher indoor air all year long!**** Take in stunning back bay views and enjoy the unbeatable location directly across from Turtle Beach and Park, where you’ll find boat, kayak, and canoe launches, a playground, and a convenient trolley stop. Sunrise Cove offers an exceptional lineup of amenities, including two community pools, a fitness center, tennis and pickleball courts, kayak and bike storage, bayside BBQ grills, and picnic areas overlooking the water. Boat lovers will appreciate the boat slips available for rent with water and electric hookups. The community also features a full-time onsite facility manager and maintenance manager for added peace of mind. Step outside and enjoy the convenience of Turtles Pub & Café, Turtles Restaurant, and a nearby marina, all just next door. Just down the road, indulge in waterfront dining at Ophelia’s on the Bay, one of Sarasota’s most beloved dining destinations. And of course, you’re moments away from world-famous Siesta Key Beach, celebrated for its powdery quartz sand, sparkling water, and unforgettable sunsets.

9011 Midnight Pass Road Unit 329, Sarasota

2 Beds ⋅ 2 Baths ⋅ Bella Costa SubDv. ⋅ 34285 Zip Code

Coastal Style Turnkey Furnished Condominium at Bella Costa is situated on the sparkling blue waters of the Intracoastal Waterway on desirable Venice Island! Offering a relaxed Florida West Coast lifestyle and premiere location you are just one mile from the sandy shores of gorgeous Venice Beach and a short stroll to charming Downtown Venice. The walkable, tree-lined streets of downtown Venice feature delightful boutique shops, inviting alfresco dining at local cafes and restaurants, the Venice Theater, Saturday Farmer's Market, Friday night music under the stars at the Gazebo and regular community events including art fairs, car shows and holiday parades. The southern trailhead of scenic Legacy Trail, for outdoor enthusiasts, is adjacent to the historic Venice Train Depot. You will love the garden style setting of this first-floor condo. Step outside to an outdoor patio where you can relax and unwind with friends and family and enjoy an open-concept Great Room design, Turnkey Coastal Style decor and furnishings, 18" ceramic tile throughout, and a split bedroom plan both with roomy walk-in closets and ensuite bathrooms. Kitchen includes stainless steel appliances, solid surface countertops, casual dining bar and stackable washer/dryer. Wind-compliant windows and slider, assigned covered parking, and storage complete this delightful condo. Residents also enjoy access to lifestyle amenities including a socially active clubhouse with gathering room, heated pool, fitness center, and scenic waterfront picnic areas to enjoy the stunning waterfront sunsets. We invite you to begin your Venice Island lifestyle!

220 Santa Maria Street Unit 139, Venice

2 Beds ⋅ 2 Baths ⋅ Condo On The Bay SubDv. ⋅ 34236 Zip Code

Step into the most luxurious waterfront condo that awaits you in this stunning two bedroom, two-bath condo in the heart of Sarasota! Enjoy breathtaking views of the Bay of Sarasota and The Gulf of America from one of two of your private balconies. This stunning 100% completely renovated 5 stack VanGogh located on the 17th floor will leave you breathless. You will not believe your eyes when you see the attention to detail built into this stunning condo. Floor to ceiling mirrors in entryway accentuate the grand view as you enter the condo. Seller did a complete demolition of all interior drywall, ceiling tiles, all interior AC ductwork, plumbing, flooring and electrical. Installed all new plumbing, electrical, AC ductwork and / outdoor lighting. All new indoor lighting design and hardware throughout. The gorgeous all new wood flooring is in main areas and bedrooms, with all new tile in the bathrooms and patios. Raised the ceilings for maximum grand feeling and the stunning views. Both bathrooms completely remodeled with top of the line marble, quartz and waterworks hardware. Extended the width of the hall to open up laundry area with a stackable washer and dryer as well as a tankless water heater. Installed all new hurricane doors at both patios. Custom doors and hardware throughout. Brand new cabinetry along with custom closet cabinetry in primary suite. Installation of a completely new and hard wired AV system for Sound, TV, lighting & shades for the entire house. Hard wired the WiFi Sonos system through out the entire condo. And wait until you see this extraordinary kitchen, it is a culinary dream… brand new top of the line Fulgor Italian appliances! Waterfall quartz island countertop and quartz backsplash. Full size counter depth refrigerator, wine cellar, and 2 freezers. Microwave, convection combo, built in coffee maker, induction range top, oven & dishwasher. Smart home features include Ring and Nest. When you are ready to retire for the evening you simply use the remote powered shade system by Creston for all windows. Entry into 888 Boulevard of the Arts has a 24 hour guarded gate station. Just steps outside the condo you will find access to kayaks and/or boats. You can also enjoy the resort style heated pool along with pickleball, tennis courts and fitness room. Assigned underground parking (this unit has the best spot in the building) as well as 2 EV charging stations up on the top deck. You are close to all the key spots that beautiful Sarasota has to offer: Lido Beach, Siesta Key, Anna Maria Island, Long Boat Key and St Armands Circle. Sarasota offers exquisite restaurants, shopping, theaters and many cultural activities including Asolo Theater, Van Wezel Performing Arts Center and John Ringling Museum. You don’t want to miss this extraordinary condo with the most precise attention to detail at every turn. This unit is truly perfection. (furniture has been removed by seller)

888 Boulevard Of The Arts Unit 1705, Sarasota

3 Beds ⋅ 2 Baths ⋅ Barrington Woods SubDv. ⋅ 34234 Zip Code

Discover the potential in this maintenance-free 3-bedroom, 2-bath condo villa, tucked away at the end of a quiet enclave of just 66 residences. With a spacious open floor plan and abundant natural light, this home is the perfect opportunity to update and customize to your own style. Inside, you'll find tile and laminate flooring throughout, an eat-in kitchen with a breakfast bar, a primary suite with an en-suite bath featuring a walk-in shower, an interior laundry room with a washer and dryer, and a year-round enclosed lanai with tile flooring—ideal for enjoying your morning coffee or relaxing in any season. A covered carport provides convenient parking and additional parking available. Residents of Barrington Woods enjoy maintenance-free living along with a community pool, covered cabana, scenic ponds with fountains, and beautifully landscaped grounds filled with mature Florida tropical foliage. Conveniently located just minutes from Downtown Sarasota, you'll have easy access to world-class dining, shopping, the marina, cultural attractions including The Ringling Museum and Asolo Repertory Theatre, as well as the boutiques and restaurants of St. Armands Circle and the white sands of Lido Beach. Whether you're searching for a seasonal getaway, investment opportunity, or full-time residence, this home offers incredible value in one of Sarasota's most desirable locations.

5080 Barrington Circle Unit 3102, Sarasota

1 Beds ⋅ 1 Baths ⋅ Bahia Vista Gulf SubDv. ⋅ 34285 Zip Code

One bedroom, one bath, taken to the studs and rebuilt, a short walk from the South Jetty at Bahia Vista Gulf. Open kitchen plan, quartz counters, luxury vinyl throughout, stainless appliances, and finishes that are perfect for this beachside gem. New sliders installed in 2023. A/C and water heater 2019. Nothing here is waiting on you. Step outside to deeded beach access and a heated community pool set above the Gulf. Water views run out over the deep water canal with direct Gulf access. Downtown Venice is minutes away for shopping and dining, and the community social calendar runs year round. This unit has an established rental history on a monthly minimum, which means qualified seasonal tenants and less turnover than a nightly rental. Buy it as income. Buy it as your February. It does both.

902 Gibbs Road Unit 283, Venice

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

An easy access slip with the views to along with the superb amenity package, Slip B-16 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 85 x 29.5, and a usable beam of 25 feet and a long and extra wide finger pier. This 'inside the T-head' slip location provides close proximity to the Marina Village, Restaurant, and Pool. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Club also reciprocates with 400 of Clubs throughout the country. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 80 feet. Beam depends on the vessel type and measure. Vessel must be approved by the Board of Directors prior to entering the Marina. Membership in the Longboat Key Club is required.

2600 Harbourside Drive Unit B-16, Longboat Key

Start Your Search