Siesta Key Homes with Tennis Court(s) Community Features

Siesta Key Homes with Tennis Court(s) Community Features

Welcome to Siesta Key, Florida—an enchanting barrier island renowned for its stunning beaches, vibrant culture, and a lifestyle that embraces both relaxation and recreation. Nestled in Sarasota County, Siesta Key is famous for its powdery white sand beaches, which have consistently ranked among the best in the nation. The island’s picturesque coastline is complemented by charming boutiques, delectable dining options, and a lively arts scene, making it a perfect destination for both residents and visitors alike.

For those seeking a luxurious lifestyle infused with an active spirit, Siesta Key offers a unique community feature: homes with private tennis courts. Imagine waking up in your beautifully designed residence, stepping outside to your very own court, and enjoying a morning match under the Florida sun. These exceptional homes provide an ideal setting for both seasoned players and beginners, fostering a sense of community and camaraderie among neighbors who share a passion for the game.

In addition to the tennis courts, many of these homes boast stunning views, spacious layouts, and modern amenities, allowing for a seamless blend of comfort and elegance. Whether you are hosting a friendly game or unwinding after a long day, the outdoor spaces are perfect for entertaining or simply soaking in the serene surroundings.

Siesta Key is not just a place to live; it’s a lifestyle choice filled with sun-soaked days, vibrant sunsets, and the thrill of an active community. Discover your dream home with a tennis court in Siesta Key, where every day feels like a vacation. Come and experience the charm of island living!

Newest Siesta Key Homes with Tennis Court(s) Community Features

$899,900
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
**PANORAMIC GULF VIEWS**TURNKEY FURNISHED**STEPS FROM SIESTA KEY BEACH**A HISTORY OF STRONG RENTAL NUMBERS** Wake up to breathtaking panoramic views of the Gulf of Mexico and distant Sarasota skyline from this spacious sixth-floor, two-bedroom, two-bath condominium located directly across the street from world-famous Siesta Key Beach. Offered turnkey furnished, this exceptional vacation property is ready for immediate personal enjoyment or continued use as a rental investment. The spacious primary bedroom features a king-size bed, while the second bedroom comfortably accommodates guests with two queen-size beds. Enjoy spectacular sunsets, city skyline and coastal breezes from two large terraces, or relax in the quiet privacy of this intimate community with just the right amount of amenities. This unit also includes a rare under-building assigned parking space, one of only eight located under the building. Enjoy a quick walk to the beach, or cool off in the community pool! On-site gas grills and two tennis courts are also available for your enjoyment! The location is truly exceptional. Siesta Key Beach is renowned for its powdery white quartz sand and is consistently recognized among the nation’s finest beaches. The public beach area offers lifeguards, restrooms, concessions and beach amenities, making it especially appealing to families and vacationers. Inside, the residence is thoughtfully furnished and equipped for comfortable coastal living, continued rental income or a combination of both! The condo was extensively remodeled and has been enjoyed as a popular vacation destination. New impact windows and sliders give you the peace of mind and protect your investment. High-end finishes, stunning views and an inside laundry closet make this a guest favorite. Recent upgrades include impact windows and doors (2026), HVAC (2023), Water Heater (2026), Electrical Panel (2025) Beyond the beach, you’re just a short walk, bike ride or drive from Siesta Key Village, where you’ll find an array of restaurants, bars, shops and entertainment. Whether you’re looking for a personal beach retreat, a vacation home, or an income-producing investment, this turnkey Siesta Key condo offers an outstanding combination of location, Gulf views, privacy, covered parking and proven rental potential. Bring your suitcase and start enjoying the Siesta Key lifestyle! Very strong rental numbers - ask agent for more details. 2027 high season bookings are already in place!

1055 Beach Road Unit B602, Sarasota
$669,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Discover effortless Siesta Key living in this beautifully updated and fully furnished 2-bedroom, 2-bath condo in the highly desirable Peppertree Bay community. Located on the Gulf side and just steps from the tennis and pickleball courts, heated pool, and private beach access, this second-floor residence offers a peaceful setting with scenic pond views. The interior has been thoughtfully updated with a renovated kitchen and bathrooms, crown molding, fresh paint, new impact windows on lanai and new flooring throughout. The spacious primary suite easily accommodates a king-size bed and features a generous walk-in closet. Additional conveniences include a full-size washer and dryer, tankless water heater, dedicated parking space, and a private storage unit located just outside the front door. Offered fully furnished and truly move-in ready, this condo makes it easy to begin enjoying the Siesta Key lifestyle from day one. Peppertree Bay offers an exceptional Gulf-to-Bay lifestyle with private beach access, a fishing pier, tennis and pickleball courts, two heated pools, two clubhouses, BBQ areas, beach chairs, car wash stations, on-site management, and a rental program. The fitness center and clubhouses are currently being renovated, adding even more to this amenity-rich community. This beautifully maintained residence is an excellent opportunity for a full-time home, seasonal retreat, or Siesta Key getaway. Just bring your suitcase and start enjoying island life!

1141 W Peppertree Drive Unit 1141, Sarasota
$479,000
1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
Beautifully Updated One-Bedroom Condo on Siesta Key Enjoy the best of island living in this beautifully updated one-bedroom, one-bath condominium on Siesta Key. This inviting unit has been completely updated and features all-new appliances and a new water heater, offering a fresh, move-in-ready interior. The community offers an impressive selection of on-site amenities, including: • Two swimming pools • Tennis courts • Four shuffleboard courts • Beach access Located on beautiful Siesta Key, this condo offers the perfect combination of comfort, convenience, and the relaxed Florida lifestyle. Whether you’re looking for a full-time residence, seasonal getaway, or investment opportunity, this property provides an excellent opportunity to own a piece of paradise just steps from the beach.

6006 Midnight Pass Road Unit 60, Sarasota
$824,000
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
Experience effortless island living in this immaculate, beautifully renovated 2-bedroom, 2-bath residence ideally situated directly across from world-famous Siesta Key Beach. The bright, open interior features a stylish kitchen with granite countertops and stainless-steel appliances. Hurricane-impact windows and sliding glass doors provide added security and efficiency, while the private lanai offers peaceful views of the community’s tranquil lake. Numerous recent improvements enhance the home’s move-in-ready appeal, including, in 2026, new windows, sliders, garage doors, a new air-conditioning system, and, in 2025, new blinds and water heater. Primary bathroom fully renovated in 2023. An attached oversized private garage provides generous space for vehicles, beach equipment and additional storage. The community’s beautifully maintained tropical grounds feature a heated swimming pool, tennis and pickleball courts, an outdoor shower, and a pavilion with grills for relaxed outdoor gatherings. Just beyond the property, the powder-soft sand and clear Gulf waters of Siesta Key Beach and the restaurants, boutiques and entertainment of Siesta Key Village are just minutes from home. Short-term rental flexibility makes this an especially attractive investment opportunity. Owners may take advantage of professional on-site property management or manage the residence independently, providing greater control over rental income and personal use. Most furnishings are negotiable, creating the possibility of a fully furnished, turnkey purchase ready for immediate enjoyment or rental. Whether envisioned as a primary residence, coastal getaway or income-producing investment, this exceptional Siesta Key property offers location, lifestyle and versatility in one of Florida’s most desirable beach communities.

1187 Lake House Circle Unit C127, Sarasota
$1,099,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium complex. If you are looking for a great investment or the perfect place to call home, look no further. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi, thermostat keyless entry! Your new condominium will be sold turnkey furnished, nothing to do except move in. Open floor plan great for entertaining. A super beverage cooler has been installed in the kitchen. You will find pull-outs and soft close doors & drawers. Two full sized beds in the guest room, and the main suite has gulf views, double vanities for convenience. Both bathrooms have walk-in showers. This is a split plan as well. What I really want you to see are the community grounds… the condo is fabulous, and this community is spectacular!!! You can search the state of Florida... no other community can compare itself to Gulf & Bay. Plus, END UNIT condos are the best - nothing compares to having an END UNIT. Gulf & Bay has 2 pools, new fitness center just steps away from the elevator plus saunas, tennis & PICKLEBALL courts, basketball, electric car charging stations, clubhouse, indoor hot tub. Another cool item is the complex is mapped out with its own app. Owners can easily navigate in and out of the grounds with your phone. No more fobs. Gulf & Bay is great for rental income. If you want rental income, this condo has it for 2027. Rentals must be a 30-day minimum 12 times a year. I know it just got better, right? Want to head to the village? Just hop on the free trolley out of the gates and head to the village for dinner and shopping. The condo is easy to show. Don’t miss seeing this community and condominium… the search is over... get here before this opportunity is gone! here are the dates booked for this coming season! Feb 1, 2027-Feb 28, 2027 27 nights $8,913.00 Mar 1, 2027-Mar 29, 2027 28 nights $10,052.00 Jan 1, 2027-Jan 31, 2027 30 nights $6,760.10 _____________ $25,725.10 As of 8-10-2026

5770 Midnight Pass Road Unit 301, Sarasota
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code
Virtually Staged. Rarely available 5th-floor residence in Siesta Gulf View’s coveted 08 stack. This exceptional beach retreat showcases an extended wrap balcony with unobstructed west and south panoramic views of Siesta Key’s white-sand beaches and glowing Gulf sunsets. Bathed in natural light, the spacious split-bedroom layout offers walk-in closets in both bedrooms, motorized storm shutters, an interior laundry room, and abundant flexibility to create a tailored coastal home—reimagine the breakfast nook as a den or keep the expansive office area. Offered for the first time in nearly 30 years, this is a rare opportunity to personalize a premier view property. Enjoy deeded beach access via the private community boardwalk, along with a pool, tennis, pickleball, fitness room, clubhouse with meeting room and kitchen, and beachside grilling and seating area—all within Siesta Gulf View’s intimate 59-residence setting, just two blocks to famous Siesta Key Village.

420 Beach Road Unit 508, Sarasota
$649,900
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Ready to Enjoy the Great Life? Welcome to your own piece of paradise at Island Reef, one of Siesta Key's most sought-after Gulf-to-Bay Communities. Perfectly positioned in the desirable "A" Building, this beautifully maintained and furnished second-floor end unit offers breathtaking panoramic views of the Gulf of Mexico from the moment you walk through the door. Natural light pours into the residence, while expansive water views create a peaceful backdrop that defines true coastal living. Offering over 1,200 square feet, this two-bedroom, two-bath residence features a desirable split-bedroom floor plan that provides comfort and privacy for both owners and guests. Thoughtfully updated over the years and offered turnkey furnished, the condo is ready to enjoy immediately while still providing the opportunity to personalize over time. Whether you're preparing dinner with the Gulf as your backdrop, enjoying your morning coffee on the lanai, or ending the day with one of Siesta Key's unforgettable sunsets, every space is designed to embrace the waterfront lifestyle. Life at Island Reef extends well beyond your front door. Begin your mornings with a walk along the private beach at Turtle Beach, spend afternoons kayaking or paddleboarding through Little Sarasota Bay, or watch dolphins play in the Gulf from the community's beachfront pool. Boating enthusiasts will appreciate the community's bayside docks with lift capability and direct access to Sarasota Bay and the Intracoastal Waterway. Residents enjoy an impressive collection of resort-style amenities, including two heated pools, private beach access, tennis and pickleball courts, shuffleboard, a fitness center, clubhouse, library, fishing pier, kayak and bike storage, beautifully landscaped walking paths, on-site management, and covered parking. Ideally located on the quieter southern end of Siesta Key, Island Reef offers a relaxed coastal atmosphere while remaining just minutes from Siesta Key Village's dining, shopping, and entertainment. Don't forget to check out the complimentary trolley that goes directly to the village!! Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this is a Rare Opportunity to own a beautifully furnished & spacious Gulf-front Condominium in Island Reef one of Siesta Key's premier Gulf-to-Bay communities, where lush tropical landscaping, resort-style amenities, private beach access and unmatched Coastal lifestyle come together harmoniously to create the perfect place to feel at Home. Call today to Book a Private Showing - these opportunities don't last long!

8764 Midnight Pass Road Unit A201, Sarasota
$1,589,000
2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Welcome to Dolphin Bay, one of Siesta Key's premier waterfront communities, where luxury coastal living meets breathtaking scenery. This beautifully maintained 2-bedroom, 2-bath residence offers 2,217 square feet of thoughtfully designed living space with panoramic views of the Intracoastal Waterway, downtown Sarasota, and beyond. Filled with natural light, the open-concept floor plan was designed to maximize the spectacular waterfront views. Floor-to-ceiling windows create an inviting atmosphere where you can relax, entertain, and watch boats glide by as the Sarasota skyline transforms from sunrise to sunset. The spacious kitchen offers abundant cabinetry, generous counter space, Thermador appliances, and a breakfast area that opens seamlessly to the main living spaces, making everyday living and entertaining effortless. Wake up each morning to stunning water views from the luxurious primary suite, complete with a spacious walk-in closet and a spa-inspired en-suite bath featuring a large walk-in shower. The generously sized guest suite also features a large walk-in closet and is conveniently located adjacent to a full bath, providing exceptional comfort and privacy for family and guests. Life at Dolphin Bay extends far beyond your residence. Enjoy resort-style amenities including a pool and spa, Har-Tru tennis courts, fitness center, elegant clubhouse, kayak launch, fishing pier, and day dock with direct access to Sarasota Bay and the Gulf. Perfectly positioned just minutes from the award-winning white quartz sands of Siesta Key Beach, this exceptional residence also places you close to the restaurants, boutiques, and vibrant atmosphere of Siesta Key Village. A short drive brings you to downtown Sarasota, home to the Van Wezel Performing Arts Hall, Sarasota Opera House, The John and Mable Ringling Museum of Art, waterfront parks, fine dining, galleries, shopping, and year-round cultural events. Whether you're searching for a full-time waterfront residence, a seasonal retreat, or the ultimate Florida lifestyle, this exceptional Dolphin Bay residence offers the rare opportunity to enjoy luxury, boating, world-class beaches, and breathtaking waterfront views—all in one of Siesta Key's most desirable communities.

1280 Dolphin Bay Way Unit 402, Sarasota
$849,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Discover this one-of-a-kind unit in Excelsior, featuring two spacious bedrooms and two bathrooms, complemented by an added staircase leading to a spacious second-story LOFT. A structural beam has been expertly installed to support the loft, and ceilings have been RAISED, enhanced with foam insulation throughout the attic for improved energy efficiency. The kitchen boasts custom solid wood cabinetry, elegant crown molding, and solid core doors. BRAND NEW carpet installed throughout bedrooms, loft and staircase. Enjoy year-round comfort with a Newer HVAC system (2023). Looking out from your front door, take in the breathtaking Gulf views, perfect for watching gorgeous sunsets. The Gulf to Bay community offers private deeded beach access and a wealth of amenities, including two large heated swimming pools with poolside restrooms and hot water showers, shuffleboard, two heated whirlpools, two lighted tennis courts, and two pickleball courts. For fitness enthusiasts, a well-equipped fitness center awaits, along with a spacious Gulf side sun deck, beach loungers and chairs, and outdoor barbecues and picnic areas. 2 Week rental minimums for those seeking to generate some income. Additionally, enjoy the intercoastal fishing pier with a shaded viewing area, a welcoming community room, and engaging monthly community events. Don’t miss your opportunity to own this exceptional property with unparalleled amenities!

6263 Midnight Pass Road Unit 403, Sarasota
$499,000
2 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
New Listing Photos now attached! Weekly rentals, prime Siesta Key location, and immediate income potential—this is the beach investment opportunity buyers wait for. Welcome to Bay Oaks, where island living meets exceptional rental flexibility in one of the most desirable communities on Siesta Key. This beautifully updated 2-bedroom, 2-bath condo is being offered fully turn-key furnished, making ownership effortless from day one. Even better, future rental bookings are already in place, allowing you to start generating income immediately—no waiting, no setup, no downtime. Just close and collect. Since its last listing, the home has been enhanced with a newly renovated kitchen, featuring stylish modern finishes that elevate both form and function. The bright, open-concept layout creates an inviting coastal feel, with seamless flow between the kitchen, dining, and living spaces—perfect for relaxing after a day at the beach or entertaining guests. Enjoy peaceful mornings on your private balcony surrounded by lush tropical landscaping, while both spacious bedrooms provide comfortable retreats filled with natural light. Bay Oaks is beloved for its unbeatable location and resort-style amenities. Situated on the bayside of Siesta Key and just moments from the powdery sands of world-famous Siesta Key Beach, residents and guests enjoy access to a sparkling pool, private fishing pier, tennis courts, shuffleboard, and beautifully maintained grounds. Hop on the free trolley for quick access to the restaurants, boutiques, and nightlife of Siesta Key Village. For investors, the biggest advantage is Bay Oaks’ highly desirable weekly rental policy—a rare and valuable feature on Siesta Key that opens the door to strong vacation rental demand and attractive income potential. Whether you're searching for a personal beach getaway, a savvy investment property, or the perfect combination of both, this Bay Oaks condo delivers. Flip-flops encouraged. **Updated Listing Photos Now Attached!**

6157 Midnight Pass Road Unit E12, Sarasota
$559,000
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Ideally on the south end of Siesta Key, directly across from the free Siesta Key trolley and less than a quarter mile to Turtle Beach, this two-bedroom, two-bath residence offers 1,093 square feet of living space with panoramic Sarasota Bay views and glimpses of the Gulf. The open-concept great room is designed to maximize the water views and features luxury vinyl tile flooring, built-in surround sound and direct access to the screened lanai. Motorized blinds enhance the lanai, creating a comfortable space to enjoy the serene bayfront scenery. The kitchen is open to the living area and offers granite countertops, stainless steel appliances, creamy white cabinetry, a spacious pantry, and views of the Gulf and Sarasota Bay. Water views continue into the primary suite, where owners can wake to spectacular sunrises from the comfort of their bedroom. The primary suite also features a custom walk-in closet system and en-suite bath. The guest bedroom offers Gulf views and a large walk-in closet. Additional conveniences include a dedicated storage space, communal laundry facilities on the same floor adjacent to the elevator, an assigned covered carport space near the elevator and abundant guest parking. Recent improvements include a new electrical panel in 2021 and a new water heater in 2026. Sunrise Cove offers an array of amenities, including a renovated clubhouse with social spaces and kitchen, fitness center, library, billiards and table tennis, two heated swimming pools, tennis courts, pickleball courts, grilling areas and boat slips available for lease. Residents can also take advantage of the kayak, canoe and paddleboard storage available for lease, along with convenient marina access nearby. Enjoy easy access to Turtle Beach, boating, waterfront recreation and all the shopping, dining and entertainment of Siesta Village. Experience the best of Siesta Key living with bayfront views, beach access and resort-style amenities in one exceptional location.

8911 Midnight Pass Road Unit 409, Sarasota
$8,000,000
Siesta Properties Inc SubDv. ⋅ 34242 Zip Code
An Extraordinary Gulf-Front Estate Opportunity There are few opportunities remaining to create a legacy estate directly on the Gulf of Mexico. At 7740 Sanderling Road, nearly one acre of pristine beachfront offers an exceptional canvas for a world-class custom residence in one of Florida's most exclusive coastal communities. Positioned along the sugar-white sands of Siesta Key, this rare Gulf-front homesite presents an unparalleled opportunity to design a private waterfront retreat with sweeping panoramic views of the Gulf of Mexico, spectacular year-round sunsets, and direct access to one of the world's most celebrated beaches. With expansive frontage and generous dimensions, the property invites limitless architectural possibilities—from a contemporary coastal masterpiece to a timeless estate designed for generations to enjoy. Located within the prestigious Sanderling Club, this exceptional property enjoys the distinction of being part of Siesta Key's only private, gated Gulf-front community with 24-hour manned security. Originally envisioned by renowned Architect Paul Rudolph, Sarasota School of Architecture, Sanderling Club has long been recognized as one of Sarasota's most coveted residential enclaves, where privacy, natural beauty, and architectural excellence come together in a setting unlike any other on Florida's Gulf Coast. Residents enjoy an exclusive collection of amenities, including a private beachfront clubhouse overlooking the Gulf, tennis and pickleball courts, a marina with boating access to Sarasota Bay, scenic nature canopy roads , and beautifully maintained grounds that preserve the community's tranquil coastal character. The neighborhood's low density and commitment to preserving its natural environment have made Sanderling Club one of the region's most enduring luxury addresses. Beyond the gates, Siesta Key offers an internationally acclaimed lifestyle defined by its powder-soft quartz beaches, turquoise Gulf waters, and relaxed sophistication. From waterfront dining and boutique shopping in Siesta Key Village to boating, paddleboarding, fishing, and endless days on the water, the island offers an effortless blend of recreation and refinement. Just minutes away, downtown Sarasota provides a vibrant cultural scene that rivals much larger metropolitan destinations. Residents enjoy world-class performing arts, acclaimed restaurants, private clubs, championship golf, luxury shopping, art galleries, marinas, and exceptional healthcare. From evenings at the Sarasota Opera or the Van Wezel Performing Arts Hall to waterfront dining at Marina Jack and shopping at St. Armands Circle, Sarasota continues to rank among the nation's premier luxury lifestyle destinations. Large Gulf-front homesites of this caliber have become exceedingly rare. Combining nearly an acre of buildable beachfront, extraordinary privacy, direct Gulf frontage, and the prestige of Sanderling Club, 7740 Sanderling Road represents an opportunity to create an iconic waterfront estate in one of the most desirable addresses on Florida's Gulf Coast. This is more than a homesite—it is the foundation for a legacy. Architectural Rendering Of What Could Be Built Are For Planning Purposes Only And Not Included In The Sale Price. Building Price Is Available On Request.

7740 Sanderling Road, Sarasota
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