Siesta Key Homes with Boatable Water Water Frontage

Siesta Key Homes with Boatable Water Water Frontage

Welcome to Siesta Key, Florida – a captivating island paradise nestled in Sarasota County, renowned for its stunning beaches, vibrant community, and tranquil lifestyle. With its powdery white sands and crystal-clear waters, Siesta Key is consistently ranked among the top beaches in the United States, making it a dream destination for both residents and visitors alike.

Imagine waking up each day to the gentle sound of waves lapping against your boat dock and the sun rising over the horizon. In Siesta Key, homes with boatable water frontage offer you this idyllic lifestyle. Whether you’re an avid boater, a fishing enthusiast, or simply someone who enjoys the serenity of waterfront living, these properties provide direct access to the Gulf of Mexico. With your boat just steps away, you can explore the surrounding islands, enjoy a sunset cruise, or partake in a day of fishing, all from the comfort of your backyard.

The sense of community in Siesta Key is as inviting as its natural beauty. With a variety of local shops, restaurants, and cultural attractions, residents enjoy a laid-back yet vibrant atmosphere. Spend your evenings dining al fresco at a waterfront restaurant or enjoying live music at one of the local hotspots.

Siesta Key is not just a place to live; it’s a lifestyle. With homes boasting boatable water frontage, you’ll find the perfect blend of luxury, adventure, and relaxation. Come discover your slice of paradise in Siesta Key, where every day feels like a vacation!

Newest Siesta Key Homes with Boatable Water Water Frontage

1129 Seaside Drive Unit 23, Sarasota
$615,000
1 Beds ⋅ 1 Baths ⋅ Sea Crest Apts SubDv. ⋅ 34242 Zip Code
Steps from the White Sands of Crescent Beach! Welcome to Sea Crest, one of Siesta Key's most desirable boutique beachfront communities, offering an intimate setting with just 40 residences. Known for its exclusivity, outstanding beachfront location, and exceptional rental flexibility, Sea Crest offers a unique opportunity to experience the very best of Siesta Key. Ideally positioned within the community, Unit #23 enjoys one of Sea Crest's most appealing features: its close proximity to the beach. Step outside your door and you're just a short stroll from the beautiful white sands of Crescent Beach and breathtaking sunsets over the Gulf of Mexico. This charming one-bedroom, one-bath condominium offers a comfortable and inviting coastal retreat with an open living and dining area, beautiful wood-look flooring, exposed ceiling beams, and tasteful coastal furnishings throughout. The fully equipped kitchen, spacious living area, and bedroom with ample storage provide everything needed for a relaxing beach getaway. Offered completely turnkey furnished, this residence is ready for immediate enjoyment or continued rental use. What truly sets Sea Crest apart is its combination of an intimate beachfront setting and outstanding rental flexibility. Short-term rentals are permitted, and the community offers a phenomenal on-site management team that assists with reservations, guest services, and property management. Unit #23 is already participating in the on-site rental program, offering a convenient transition for buyers interested in continuing rental activity while enjoying the property for their own personal use. Residents and guests enjoy direct access to the world-famous sands of Crescent Beach, a heated swimming pool, beachfront lounging areas, and incredible Gulf sunsets. All of this is conveniently located near some of Siesta Key's favorite restaurants, shopping, and entertainment. Whether you're looking for a personal beach retreat, an investment opportunity, or a combination of both, Unit #23 offers an exceptional combination of location, convenience, and flexibility. With just 40 residences and the beach only steps away, it's easy to see why Sea Crest remains such a special place on Siesta Key!

1129 Seaside Drive Unit 23, Sarasota
1129 Seaside Drive Unit 14, Sarasota
$630,000
1 Beds ⋅ 1 Baths ⋅ Sea Crest Apts SubDv. ⋅ 34242 Zip Code
Completely Renovated, Turnkey Furnished, and Located in One of Siesta Key's Most Desirable Boutique Beachfront Communities! Welcome to Sea Crest, an intimate 40-unit community along the beautiful white sands of Crescent Beach. Known for its exclusivity, outstanding location, and relaxed coastal atmosphere, Sea Crest offers a unique opportunity to own in one of Siesta Key's most sought-after beachfront settings. This beautifully renovated one-bedroom, one-bath condominium has been completely transformed with high-end finishes and a fresh coastal design throughout. The bright, open-concept floor plan features beautiful wood-look flooring, exposed ceiling beams, crisp white cabinetry, stainless steel appliances, and an impressive kitchen with an oversized island and breakfast bar seating. Soft coastal colors, tasteful furnishings, and thoughtful details create a beautiful, inviting space that perfectly captures the Siesta Key lifestyle. The bathroom has also been completely updated with a beautifully tiled walk-in shower, glass enclosure, and modern finishes. Offered fully turnkey furnished, this property is ready to enjoy from day one, with nothing left to do! What truly sets Sea Crest apart is its boutique setting combined with exceptional rental flexibility. **Short-term rentals are permitted**, and the community offers a phenomenal on-site management team to help oversee rentals and guest services, making ownership especially convenient for those looking to generate rental income while enjoying their own personal beach getaway. Residents and guests enjoy direct access to the world-famous sands of Crescent Beach, a heated swimming pool, beachfront lounging, and incredible Gulf sunsets. All of this is conveniently located near some of Siesta Key's favorite restaurants, shopping, and entertainment. Whether you're looking for a personal coastal retreat, an investment opportunity, or the best of both worlds, this fully renovated residence offers an exceptional combination of quality, location, and flexibility. With just 40 units, Sea Crest provides the intimate beachfront experience that makes this community so special.

1129 Seaside Drive Unit 14, Sarasota
4938 Commonwealth Drive, Sarasota
$2,650,000
4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Exceptional luxury coastal living on Siesta Key! Positioned on Siesta Key’s Grand Canal with quick access to Sarasota Bay, this fully renovated estate offers the perfect blend of high-end comfort and modern efficiency. Powered by solar panels with battery storage, this eco-conscious home delivers peace of mind and low utility costs. The sprawling open floor plan highlights a newly integrated primary guest suite and seamless indoor-outdoor flow opening to a resort-style heated cocktail pool and spa. A standout feature is the expansive, grandfathered 1,300 sq. ft. bonus space—providing endless possibilities for a game room, home gym, or customized lounge. Complete with high-end boating amenities and located just minutes from world-famous Siesta Key Beach and Village. Move-in ready perfection!

4938 Commonwealth Drive, Sarasota
3607 Flamingo Avenue, Sarasota
$4,950,000
3 Beds ⋅ 4 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Exceptional Waterfront in North Siesta Key's Bay Island Shores Community. Experience the best of coastal living in this custom built residence with direct access just minutes to the Intracoastal Waterway. The home features a 2023 14,000lb dock/lift with electric and 3pnt moorage. Step inside a welcoming slate tile entry foyer to discover timeless quality design with Brazilian Ipe hardwood flooring throughout, hurricane rated windows, French doors and volume Pine ceilings. At the heart of the home is a true cook's kitchen with Wolff Gas Range, built-in Sub-Zero stainless refrigerator, Fisher Paykel dishwasher and soap-stone countertop. A walk-in chef's pantry, abundant cabinetry and full wet-bar with wine refrigeration elevate the entertaining experience. The Primary Bedroom Suite, set it its own private wing, offers a tranquil retreat w/French doors opening to a full private deck, perfect to enjoy sunrise and enjoy the water vistas; generous closet space and spa-inspired Bath; Guests Private Wing and other rooms offer flexibility. Laundry room w/sink; office nook and mudroom are conveniently located off the 3-car garage. Outdoors, enjoy multiple covered decks, one with gas fireplace for perfect evening waterfront ambiance; overlooking heated salt-water pool/spa; tropical lighted landscape and water view. Located just minutes to downtown Sarasota; shopping; restaurants and cultural venues.

3607 Flamingo Avenue, Sarasota
5619 Midnight Pass Road Unit 502, Sarasota
$489,900
2 Beds ⋅ 2 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code
Enjoy the laid-back island lifestyle in this beautifully maintained 2-bedroom, 2-bath furnished second-floor condo in the highly desirable White Sands Village. Overlooking a serene canal, this move-in-ready residence offers tranquil water views and an ideal location just moments from Siesta Key's world-famous beaches. Freshly painted and tastefully furnished, the condo features a bright, open layout, an in-unit washer and dryer, and the convenience of a covered carport. Relax in your living room while enjoying peaceful canal views and Florida's year-round sunshine. White Sands Village offers exceptional amenities, including a community pool, clubhouse, and grilling patio perfect for entertaining family and friends. Boating enthusiasts will appreciate the availability of boat slips through the community waitlist. Ideally located within walking distance to Siesta Key Beach and less than a mile from the shops, restaurants, and nightlife of Siesta Village, this property makes an excellent primary residence, vacation getaway, or investment opportunity. With a two-week minimum rental policy, owners enjoy flexibility and income potential. A shared first floor storage unit is included for all your beach supplies. Seller is motivated to sell by year end.

5619 Midnight Pass Road Unit 502, Sarasota
6157 Midnight Pass Road Unit E75, Sarasota
$419,000
1 Beds ⋅ 1 Baths ⋅ Bay Oaks SubDv. ⋅ 34242 Zip Code
Experience the best of Siesta Key living in this beautifully updated, turnkey furnished condo located in the desirable Bay Oaks community. Situated on the top floor in a quiet corner of Building E, this one-bedroom, one-bathroom residence offers added privacy, abundant natural light, and peaceful views toward the Intracoastal Waterway. With its inviting coastal atmosphere and convenient island location, this property is an ideal beach getaway, seasonal retreat, or investment opportunity. The thoughtfully designed interior features an open living and dining area that flows into an updated kitchen complete with granite countertops, stainless steel appliances, and generous cabinet space. Sliding glass doors lead to a private screened lanai, perfect for enjoying the morning breeze and relaxing in the Florida sunshine. The spacious primary bedroom comfortably accommodates a king-size bed and includes a separate vanity area and large walk-in closet. A built-in Murphy bed provides additional sleeping accommodations for guests, while an in-unit washer and dryer adds everyday convenience. The residence also includes its own assigned covered parking space, a valuable feature for island living. Bay Oaks offers a wonderful selection of amenities surrounded by mature tropical landscaping, including a heated swimming pool, tennis and pickleball courts, saunas, a clubhouse with billiards, and an on-site manager. Along the Intracoastal Waterway, residents can enjoy a fishing pier and a shaded waterfront picnic and grilling area, ideal for watching boats pass by. Just minutes from Siesta Key's world-famous white sand beaches, Bay Oaks is perfectly positioned to enjoy everything the island has to offer. The free Siesta Key Trolley stops directly outside the community, providing easy access to Siesta Key Village, restaurants, shopping, and entertainment. The nearby Stickney Point Bridge also offers convenient access to mainland Sarasota. Whether you're looking for a personal island escape or an income-producing property, Bay Oaks offers the flexibility of weekly rentals in a sought-after Siesta Key location. With its top-floor corner setting, covered parking, updated interior, and excellent community amenities, this condo presents a wonderful opportunity to enjoy the Siesta Key lifestyle.

6157 Midnight Pass Road Unit E75, Sarasota
8900 Blind Pass Road Unit A303, Sarasota
$799,900
1 Beds ⋅ 1 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code
Top-floor, turnkey beachfront living with your own assigned boat slip—experience the best of both worlds on the quiet southern end of world-renowned Siesta Key in Sarasota, Florida. Breathtaking Gulf views greet you from every room of this beautifully remodeled 1-bedroom, 1-bathroom condo, where tranquil turquoise waters and a beachfront setting create an extraordinary coastal retreat. An enclosed patio with hurricane-impact windows offers a cruise-ship-like perspective over the Gulf. Open the windows to welcome coastal breezes and the soothing sound of waves along the shore. With the Gulf on one side and Blind Pass Lagoon on the other, enjoy both sunrise and sunset, sand between your toes, and boating adventures from your assigned slip. Launch a kayak or paddleboard to explore the waterways, or head out by boat toward Sarasota Bay and the open Gulf with no bridges along the way. Thoughtfully remodeled throughout, the interior features ceramic wood-look tile, soft coastal colors, updated fans and light fixtures, and an open floor plan designed to showcase the views. The beautifully renovated kitchen features granite countertops, custom wood cabinetry with soft-close doors, a tile backsplash, and stainless steel appliances. An opened kitchen wall enhances sightlines, while an additional glass door brings in views of Blind Pass Lagoon, where wildlife, kayakers, and boaters provide an ever-changing backdrop. Beautifully appointed furnishings complement inviting spaces for dining and entertaining, including a kitchen breakfast bar, a full dining area, and additional dining space on the enclosed patio. Thoughtful furniture with built-in storage and an additional interior closet provide room for beach essentials. Wake to water views in the primary bedroom, complete with an expansive walk-in closet housing a full-size washer and dryer—a rare convenience in this community for owners and renters alike. The thoughtfully renovated bathroom features a glass-enclosed walk-in shower, an updated vanity with a granite countertop, and updated lighting. Additional highlights include air conditioning updated in 2023 and a new building roof in 2025. Monthly fees include water, sewer, internet, and cable. Enjoy long beach walks, a heated community swimming pool, boating, kayaking, and fishing—all at your fingertips. Walk to waterfront dining at Turtles Restaurant and Ophelia’s on the Bay, or take the free trolley to Siesta Key Village for dining, live entertainment, and charming shops. Discover downtown Sarasota’s cultural offerings, including ballet, symphony performances, the Van Wezel Performing Arts Hall, and the farmers market, with convenient access to Sarasota Bradenton International Airport. Whether you seek a turnkey beachfront escape, an investment opportunity with one-week minimum rentals, or a full-time coastal residence, this exceptional Fishermans Cove condo brings together beachfront beauty and a bonus boating lifestyle if desired!

8900 Blind Pass Road Unit A303, Sarasota
5970 Midnight Pass Road Unit 177, Sarasota
$650,000
1 Beds ⋅ 2 Baths ⋅ Palm Bay Club SubDv. ⋅ 34242 Zip Code
Beach to bay, turnkey and ready to enjoy—this one-bedroom residence at the Palm Bay Club offers an approachable way to own a piece of the Siesta Key lifestyle without sacrificing the amenities that make this community so desirable. Positioned on the Gulf side of Midnight Pass Road, the powder-white sands and turquoise waters of Crescent Beach are just steps from your door. Inside, the thoughtfully designed floor plan makes excellent use of every space. Handsome vinyl plank flooring provides a durable, low-maintenance foundation for relaxed coastal décor, while the kitchen pairs crisp white cabinetry with bold black granite countertops and stainless-steel appliances. The open living and dining area is comfortably furnished and ready for everything from quiet mornings to recharging between Siesta Key adventures. An enclosed lanai has been incorporated into the living space, where three large glass sliders welcome abundant natural light and open to capture the island breeze. The peaceful bedroom features two beds to maximize guest accommodations, while the updated bath continues the condo’s fresh, easygoing aesthetic. Offered turnkey furnished, this residence makes the transition from closing day to beach day refreshingly simple. And at Palm Bay Club, ownership extends well beyond your front door. Enjoy private Crescent Beach access, two heated swimming pools, a waterfront hot tub overlooking the Intracoastal, fitness center, lighted tennis and pickleball courts, BBQ grills, fishing pier and boat docks available for daily rental. With a three-night minimum rental policy and established onsite management, this efficient one-bedroom residence presents a compelling combination of personal enjoyment, rental flexibility and exceptional Siesta Key value.

5970 Midnight Pass Road Unit 177, Sarasota
1207 Sharswood Lane, Sarasota
$3,195,000
3 Beds ⋅ 4 Baths ⋅ Spice Bay SubDv. ⋅ 34242 Zip Code
LIVE THE SIESTA KEY LIFESTYLE IN SPICE BAY—an intimate, gated enclave of just 14 estate-sized homesites in one of Siesta Key’s most distinctive Intracoastal communities. Custom built by award-winning builder Ryan Perrone of Nautilus Homes, this sophisticated residence offers approximately 3,235 square feet of beautifully designed SINGLE-LEVEL LIVING with exceptional craftsmanship, privacy, and effortless indoor-outdoor entertaining. Offered FURNISHED, this exceptional home is ready for you to immediately begin enjoying the Siesta Key lifestyle. From the moment you enter through the impressive mahogany front door, a dramatic wall of glass sliders draws your eye to the lush tropical surroundings and expansive outdoor living areas beyond. Filled with NATURAL LIGHT, the home blends refined finishes with relaxed “barefoot elegance,” creating a coastal retreat that feels both luxurious and inviting. The thoughtfully designed floor plan features 3 BEDROOMS, EACH WITH ITS OWN ENSUITE BATH, providing exceptional privacy and comfort for family and guests. The spacious primary suite includes a private den/study and a luxurious spa-inspired bath, while the additional bedrooms are generously sized and beautifully appointed. A PRIVATE CASITA LOCATED JUST OFF THE PORCH adds even more flexibility—perfect for visiting guests, extended family, a private retreat, studio, or home office. Throughout the home, you’ll find wide-plank oil-finished wood flooring, handcrafted details, custom closets and built-ins that reflect the quality of this custom residence. At the heart of the home, the GOURMET CHEF’S KITCHEN was created for entertaining and features a 6-burner gas range, steam oven, two dishwashers, generous workspace and a large walk-in pantry. Open the sliders and embrace true Florida indoor-outdoor living. The extended courtyard and lanai enjoy DESIRABLE SOUTHERN EXPOSURE and a private tropical setting—perfect for morning coffee, entertaining friends, relaxing with an evening cocktail or unwinding in the spa. For boating enthusiasts, enjoy access to a DEEP-WATER BOAT DOCK WITH A 13,000-LB LIFT, making it easy to spend your days exploring Sarasota Bay and the surrounding waterways. An oversized THREE-CAR TANDEM GARAGE provides exceptional space for vehicles, storage and all your island toys. Spice Bay offers the rare combination of PRIVACY AND CONVENIENCE on Siesta Key. Walk or bike to the beach, nearby shops and restaurants, spend your days enjoying the world-famous quartz sands of Siesta Key Beach, then head downtown for Sarasota’s celebrated dining, arts and cultural scene. This exceptional TURNKEY FURNISHED custom residence captures the very best of luxury coastal living—private, refined and unmistakably Siesta Key.

1207 Sharswood Lane, Sarasota
6157 Midnight Pass Road Unit E93, Sarasota
$475,000
2 Beds ⋅ 2 Baths ⋅ Siesta Plat SubDv. ⋅ 34242 Zip Code
Exceptional opportunity on SIESTA KEY! Whether you're searching for a vacation getaway, full-time island residence, or income-producing investment, this TURNKEY 2-bedroom, 2-bath condo at Bay Oaks offers an unbeatable combination of location, flexibility and value. With WEEKLY RENTALS ALLOWED, owners have the freedom to take advantage of Siesta Key's highly desirable vacation rental market while still enjoying the property themselves. Outside rental management and self-management is allowed, providing added flexibility for investors. Located on the third floor, this spacious 1,101 sq. ft. condo is being sold TURNKEY and ready to enjoy from day one. The kitchen has been beautifully renovated creating a fresh, updated space with stainless steel appliances, gorgeous quartz countertops, large island with seating, and coastal backsplash. The open living and dining areas flow onto a screened in balcony overlooking mature tropical landscaping—the perfect spot to enjoy your morning coffee or unwind after a day at the beach. A generous outdoor storage closet provides convenient space for beach chairs, umbrellas and all your island essentials. The split bedroom layout offers privacy for owners and guests, with two spacious bedrooms and two full bathrooms. An IN-UNIT WASHER AND DRYER adds another sought-after convenience for both personal use and vacation rentals. Bay Oaks provides an impressive collection of amenities including a heated community pool, fishing pier along the Intracoastal Waterway, tennis and pickleball courts, BBQ and picnic areas, and covered parking. Leave the car behind and embrace the island lifestyle with the Siesta Key trolley providing convenient transportation to Siesta Key Village, local restaurants, shops, entertainment and Siesta Key's world-famous white-sand beaches. With weekly rentals permitted, flexible management options, turnkey furnishings, a renovated kitchen and an outstanding Siesta Key location, this condo offers an incredible opportunity to own your own piece of paradise while enjoying the potential for vacation rental income. Bring you sunscreen and come experience everything that makes Siesta Key one of Florida's most sought-after island destinations!

6157 Midnight Pass Road Unit E93, Sarasota
8773 Midnight Pass Road Unit 504G, Sarasota
$615,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Welcome home to your tropical retreat at Island Reef on south Siesta Key! Island Reef is a Gulf to Bay resort style community. Amenities include: 2 heated pools, private beach, pickleball, tennis, clubhouse and docks. There is an active social calendar and in-house rental management as well. This beautiful penthouse unit has a wonderful pool and courtyard view. 504G is being offered Turnkey Furnished. This beachy condo has been extensively upgraded including the kitchen, both bathrooms, a laundry with full-size washer and dryer, and a raised ceiling in the dining area. The knotty pine floors and doors are reminiscent of a coastal cottage. Indirect lighting can be dimmed to suite your needs. A new AC was installed in Oct 2026 and the warranty will be transferred to the new owners. The kitchen and bathrooms have solid wood paneled cabinets, granite countertops, and subway tile bath and shower surrounds. In the kitchen the lighted cabinets allow for a beautiful display of dishes, glassware, and favorite collectibles. The living room and dining area have comfortable coastal furniture. The large dining table holds 6-8. Glass sliding doors open to a garden style lanai with slate tile flooring. Enjoy the tropical breeze and pool view while sipping your morning coffee on this wonderful lanai. Throughout the condo there are several unique antique wood chests and other furniture pieces., which are perfect for additional storage. The coastal artwork and knick-knacks are included in the purchase of this home. From the primary bedroom, you can also access the lanai through sliding glass doors. There is a large walk-in closet and an ensuite bathroom with dual sinks and large shower. The guest bedroom has a three-piece full wall shelving /desk unit. There is also a full wall built-in closet. Across the hallway is a laundry and storage room. If you are ready to make a move to paradise, please call for a private showing. When you see 504G you will fall in love! Buy now and enjoy winter on Siesta Key!

8773 Midnight Pass Road Unit 504G, Sarasota
3441 Gulfmead Drive, Sarasota
$10,500,000
6 Beds ⋅ 7 Baths ⋅ Gulfmead Estates SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. This grand canal-front estate in one of North Siesta Key’s most exclusive neighborhoods is expected to be complete in a few months. Designed and built by Pham Development on a 17,842-square-foot (0.41-acre) lot, the traditional-style home will provide 4,769 square feet, 6 bedrooms, 6 full baths, and 1 powder bath. There are two separate guest suites above the two-car garages providing 4 garage spaces in total, with elevator access to each suite. Enjoy water views throughout the home, with the opportunity to create an office, a fitness room, or both. At the heart of the home, a gourmet chef’s kitchen will feature a striking quartz waterfall island, elegant pendant lighting, and custom cabinetry. The premium appliance suite includes a 72-inch Sub-Zero refrigerator, a Cove dishwasher, and a Wolf range, coffee maker, and microwave. The adjoining living and dining areas will flow seamlessly outdoors to a Wolf-equipped outdoor kitchen, private pool and hot tub spa, spacious backyard, and lush new landscaping. The deep-water Grand Canal offers direct, bridge-free boating access to the Gulf and can accommodate vessels with drafts of up to 13 feet. A new dock and boat lift are planned, completing this waterfront setting for boating, entertaining, and time with family. Images contain virtual staging.

3441 Gulfmead Drive, Sarasota
Start Your Search

How much is your home worth?

Get instant property value now!