Siesta Key Homes with Street Lights Community Features

Siesta Key Homes with Street Lights Community Features

Welcome to Siesta Key, Florida—a tropical paradise renowned for its stunning beaches, vibrant culture, and laid-back lifestyle. Nestled in Sarasota County, this charming barrier island boasts some of the finest white sand beaches in the United States, making it a haven for sun-seekers and nature lovers alike. Whether you're strolling along the picturesque shoreline, indulging in fresh seafood at local eateries, or exploring the unique boutiques and art galleries, Siesta Key offers a delightful blend of relaxation and adventure.

One of the standout features of this enchanting community is the Homes with Street Lights neighborhood. This inviting community is designed to enhance your living experience with well-lit streets that promote safety and accessibility for residents and visitors alike. Imagine evening strolls under the glow of street lights, where friendly neighbors greet you and the warm breeze carries the sound of laughter and joy.

In addition to its charming ambiance, the Homes with Street Lights community offers a variety of housing options, from cozy beach cottages to luxurious waterfront estates, catering to diverse lifestyles and preferences. Residents enjoy easy access to nearby parks, recreational facilities, and of course, the breathtaking beaches that make Siesta Key a sought-after destination.

Whether you're looking for a permanent residence or a vacation getaway, Siesta Key's Homes with Street Lights community provides the perfect blend of comfort, safety, and coastal charm. Discover your dream home in this idyllic setting, where every day feels like a vacation!

Newest Siesta Key Homes with Street Lights Community Features

$3,995,000
4 Beds ⋅ 3 Baths ⋅ Ten35 Seaside SubDv. ⋅ 34242 Zip Code
Welcome to Ten35 Seaside Drive, a newer mid-rise community at the south end of world-renowned Siesta Key Beach, where turquoise Gulf waters meet pristine quartz sand. Ten35 Seaside elevates island living with luxurious residences designed to highlight the area’s natural beauty. Gulf-view residence 502 offers four bedrooms, three baths and 2,385 square feet of thoughtfully designed living space. Floor-to-ceiling glass, an open-concept interior, and expansive terraces frame sweeping views of the sea, sand and sky. Refined finishes include porcelain tile floors, premium cabinetry, top-of-the-line appliances and a spacious primary suite with a spa-inspired bath. The main terrace is ideal for enjoying spectacular sunsets, while a second terrace off the en-suite guest bedroom captures beautiful sunrises. The kitchen features solid-wood cabinetry, Wolf and Sub-Zero appliances, a gas cooktop and a wine refrigerator. Additional highlights include solid-core entry and interior doors, floor-to-ceiling, hurricane-resistant balcony doors with laminated solar-tinted glass, sound-reducing laminated windows with solar-tinted glass, a recirculating hot-water system, high-efficiency heating and air conditioning, stained tongue-and-groove cypress terrace ceilings, tiled terrace floors and two covered parking spaces. Ten35 Seaside offers amenities that complement its beachfront setting, including a swimming pool and spa, fire pit, beach lounge chairs and umbrellas, kayaks, paddleboards, concierge-arranged water activities, fitness center and Gulf-front barbecue area. Daily beach chairs and umbrellas are also available. Residence 502 presents a rare opportunity to own a fully operational, potential income-producing property on Siesta Key’s Crescent Beach, one of Florida’s desirable vacation rental destinations. The residence is enrolled in the community’s on-site professional rental management program, providing immediate revenue while eliminating the setup time and day-to-day demands of vacation-rental ownership. Marketing, guest services, housekeeping and operations are managed on-site, allowing owners to potentially earn income while reserving time for personal use. Rental terms permit one-week minimum stays during the off-season and two-week minimum stays during peak season, balancing revenue potential with property preservation. Just moments from the dining and shopping of Siesta Key’s South Village, the property consistently attracts repeat visitors, supporting strong occupancy. Whether you are expanding an investment portfolio, completing a 1031 exchange or seeking a vacation home that can offset ownership costs, Residence 502 offers a rare combination of a Gulf-front location, professional management and potential rental income from day one. A must-see opportunity.

1035 Seaside Drive Unit 502, Sarasota
$670,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Live the Siesta Key lifestyle! This beautifully maintained 2-bedroom, 2-bath condo offers the perfect combination of island living, rental potential, and resort-style amenities. Ideally situated in the desirable Gulf-side community of Peppertree, this second-floor residence is just a short stroll from the tennis and pickleball courts, heated pools, and Siesta Key’s private-access beach. From the moment you arrive, you’ll appreciate the peaceful setting and tranquil views overlooking one of Peppertree’s picturesque ponds. The condo has been thoughtfully updated with all new impact windows, renovated kitchen and bathrooms, and updated flooring, creating a comfortable and inviting beach retreat. The spacious primary bedroom easily accommodates a king-size bed and features a walk-in closet. The home is offered turnkey furnished, making it ready to enjoy immediately or continue as a seasonal rental. It has consistently generated rental income during peak season, while also providing the flexibility to enjoy it personally during the off-season. Additional features include a full-size washer and dryer, newer A/C installed in 2019, a private storage unit conveniently located just outside the back patio, and a dedicated parking space. Peppertree is truly a destination within Siesta Key, offering direct Gulf-to-Bay access, a private fishing pier, tennis and pickleball courts, two heated pools, two clubhouses, BBQ grills throughout the community, beach chairs, car wash areas, and on-site management with a rental program. High and dry with no storm damage, this exceptional condo offers the opportunity to own your own piece of paradise on world-famous Siesta Key. Whether you’re looking for a personal beach getaway, an investment property, or the best of both, this inviting Peppertree residence is ready to welcome you home.

1130 W Peppertree Lane Unit 118, Sarasota
$399,000
2 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
Enjoy easy island living in this beautifully maintained first-floor condominium at Bay Oaks on Siesta Key. With your assigned carport just steps from the front door, there's no need to wait for elevators, making everyday living and guest arrivals effortless. This versatile one-bedroom residence features a converted den that functions as a second bedroom, allowing the property to be successfully marketed and rented as a two-bedroom vacation rental. A favorite among returning guests, this turnkey-furnished unit offers an excellent opportunity for personal enjoyment or investment income. Inside, ceramic tile flooring flows throughout the living and dining areas, while the flexible floor plan comfortably accommodates family and visitors. Step outside to a private patio surrounded by mature trees, providing a peaceful retreat and convenient rear access to the community's resort-style amenities. Residents and guests enjoy Bay Oaks' impressive amenities, including a heated pool, tennis courts, fishing dock, social room, and outdoor grilling areas. Located directly on the free Siesta Key trolley route, you'll have easy access to world-famous Siesta Beach and the shops, dining, and entertainment of Siesta Key Village. Bay Oaks permits one-week rentals, making this a highly desirable and consistently popular rental property. Sold turnkey furnished, this island getaway is ready for immediate enjoyment or rental income from day one.

6157 Midnight Pass Road Unit G11, Sarasota
$1,400,000
3 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
A TRUE 3-bedroom condo residence in desirable Casarina, a premier building positioned directly on the quartz white sands of #1 Siesta Key beach and the Gulf of Mexico. Step into this beautiful spacious residence and experience the flow of this 2,165-square foot open floor plan conducive to daily living, entertaining and accommodating family and friends. Sold turnkey furnished, this residence boasts impact windows & sliders providing security and protection, large ceramic floor tile throughout perfect for beach living and rich new carpet in the primary bedroom. The updated kitchen is stunning boasting neutral cabinetry, quartz countertops, stainless Jenn-Air appliances, Fisher & Paykel double dishwasher, quartzite island & breakfast bar, instant hot water faucet & 3 spacious pantries. The primary bathroom was updated in 2026 with quartzite countertops and upgraded dual vanities. Custom wood closet organizers are featured in all the bedrooms and an electric fireplace in the living room. The A/C was replaced in 2025 and tankless water heater in 2023. Casarina is a secure building which has just undergone a complete building renovation & infrastructure. It offers an onsite manager and is fully funded with a 10-year capital plan and no special assessments. Besides the powder-white sand beach, experience tropical living on 7 acres of refreshed lush Florida landscaping, large refurbished heated pool and spa, cabana with outdoor kitchen & dining area, new poolside pergola with seating, 2 grilling areas, sunset decks, gas firepit with Adirondack chairs, resurfaced & lighted tennis court, 2 pickle ball courts, basketball hoop, fitness center, and social room/library. This condo offers secure under-building garage parking with an adjacent storage closet #5. The building renovation & infrastructure within the past two years includes a new reengineered resilient roof, new electrical and fire alarm systems elevated to the 2nd floor, new raised backup generator, new secured A/C units, multiple custom flood-prevention panels/dams, new ground water pump infrastructure, relined plumbing pipes, and refurbished elevators. Minutes to Siesta Village, shopping, restaurants and the culture of downtown Sarasota! So come on down and enjoy Florida living!

5880 Midnight Pass Road Unit 307, Sarasota
$680,000
2 Beds ⋅ 2 Baths ⋅ Castaway Cove SubDv. ⋅ 34242 Zip Code
It's time to SIMPLIFY! Sun. Sand. Surf. Fantastic Opportunity and sure to impress! The last unit in this community sold for 800,000. Welcome to this completely renovated residence at Castaway Cove, a boutique waterfront condominium community tucked away on the quiet south end of Siesta Key, just a short walk to Turtle Beach. This second-floor unit offers a rare coastal vantage point with sweeping views of Blind Pass Lagoon, the Intracoastal Waterway, and the Gulf of Mexico, delivering a rarely found three-water perspective. Morning light reflects across the lagoon, afternoons might feature manatees or dolphins, and evenings are reserved for unforgettable sunsets over the Gulf. Dock space is available for boating enthusiasts, and the calm lagoon waters provide ideal conditions for kayaking and paddleboarding from Castaway’s private launch toward the newly-opened Midnight Pass. The residence has been remodeled wall to wall and floor to ceiling since 2020, with thoughtful attention to both design and infrastructure. The open floor plan blends the kitchen, dining, and living areas seamlessly, allowing water views to take center stage from nearly every angle. Porcelain tile flooring runs throughout the entire unit, creating a clean, cohesive look that complements the seaside setting. The kitchen features shaker-style Providence White cabinetry with glass-front display cabinets and interior lighting, a pantry with pull-out shelving, Pompeii Quartz countertops, a Glazzio tile backsplash, and updated appliances including refrigerator, range, dishwasher, built-in microwave, washer, dryer, and HVAC system. The primary suite, perched above Blind Pass, is a serene retreat with crown molding, solid core doors, and custom closet systems with mirrored panels. The ensuite bath offers dual vanities topped with Pompeii Quartz, a walk-in shower with glass enclosure, tiled bench, multiple body jets, subway tile walls, and subtle motion-sensor lighting. The guest suite, with views of the ICW, features a barn door entry and a bath with cast-iron tub and quartz-topped vanity. A screened lanai extends the living space outdoors with porcelain tile flooring, a tongue-and-groove ceiling, new screens and railings, and tranquil water views that invite morning coffee or evening relaxation. Additional features include recessed lighting throughout, ceiling fans, a woven dining area chandelier, sheer and room-darkening solar shades, Schlage door lock, Ring doorbell, and Nest thermostat. Castaway Cove is a low-density community of just eight residences offering ample parking, professional management, and exceptionally low association fees. Recent community improvements include a new seawall, refreshed landscaping, updated exterior lighting and irrigation system, and a freshly painted building. The two-story structure is NOT subject to a Milestone Inspection.

9226 Midnight Pass Road Unit 3B, Sarasota
$529,000
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Experience true waterfront living at Sunrise Cove with spectacular Intracoastal Waterway views, breathtaking sunrises each morning, and beautiful moonrises each evening. This TURNKEY FURNISHED 2- bedroom, 2-bath condo is located on the second floor and offers the perfect blend of comfort, convenience, and resort-style amenities. The spacious living room features sliding glass doors that open to a screened-in lanai, creating the perfect setting to relax and enjoy panoramic Intracoastal views throughout the day. The primary bedroom offers a walk-in closet and en-suite bath, while the second bedroom also features a walk-in closet and beautiful views toward the Gulf of Mexico and the beach across the street. The hall bathroom includes a walk-in shower and tile flooring. The kitchen features a convenient pass-through to the dining and living areas, making entertaining effortless. Sunrise Cove offers an impressive array of amenities, including two heated swimming pools, an Olympicsize pool with restrooms and a covered lounge area, pickleball and tennis courts, a state-of-the-art fitness center, and a game room. On-site management and 30-day minimum rentals provide flexibility and excellent income-producing potential. Turtle Beach is directly across the street, while the free Siesta Key Breeze trolley stops nearby approximately every 15 minutes, making it easy to explore Siesta Key. Two popular waterfront restaurants, Turtles on the Bay and Ophelia’s on the Bay, are conveniently located right next door. Additional features include an extra storage closet conveniently located near the elevators in the laundry room. Recent community improvements include new roofs, new docks, and newly completed carports. Whether you’re looking for a vacation getaway, income-producing property, or full-time residence, this fabulous waterfront condo offers an exceptional opportunity to enjoy the best of Siesta Key living.

8977 Midnight Pass Road Unit 219, Sarasota
$45,000
4 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code
Fractional Ownership. FRACTIONAL OWNERSHIP **GUARANTEED GULF FRONT DELUXE UNIT** Imagine a perfect family retreat every year for Memorial Weekend on world famous Siesta Key Beach! Why not let the Hyatt Vacation Club manage all your entertainment and luxury high-end. GULF FRONT WITH GULF VIEW accommodations! For local residents and all owners, enjoy the alternative lifestyle for two weeks a year with an additional float week. This year’s dates are May 22-May 29 and May 29 to June 5 in 2027. Enjoy the option of the Hyatt Vacation Club’s exchange program, reservation procedures, point values, and availability to change your family get-togethers! This floorplan offers a primary suite, a junior suite, a guest bedroom, and a den with a sleeper sofa. These units overlook the pool and beach; not all units do. The best part of Siesta Key is that you will not need a vehicle. Trolley, buses, golf carts are all available for Siesta Key transportation. For casual dining, fine dining, live entertainment every day, this is the destination everyone is discovering. Easy flights, easy drive! More details upon request. This is a great opportunity to act on at these exceptionally low prices!

915 Seaside Dr Unit 405, WEEKS 22-23, Sarasota
$6,300,000
5 Beds ⋅ 5 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
NEW 2026 MODERN TROPICAL ESTATE | 5 BEDROOMS | 2 PRIMARY SUITES | 3-CAR GARAGE | POOL CABANA | INTRACOASTAL VIEWS Completed in 2026 by CribbsCo Development, this modern tropical residence makes an architectural statement with an approximately 9.5' x 9' Sapele wood pivot entry door handcrafted in the U.S. Two primary suites feature custom finished walk-in closets. The upstairs main primary is separated from the additional bedrooms by a glass breezeway and offers a pool-view balcony, custom cabinetry with integrated wet bar and built-in writing desk. Its spa-inspired bath features a soaking tub, oversized walk-in shower, dual vanities, private water closet and custom solid-oak barn door. Bathrooms feature Biancatto leathered dolomite, Kohler and California Faucets fixtures, and TOTO toilets. The ground-floor primary opens to a private patio overlooking the garden and outdoor gym. Two additional upstairs bedrooms share a full bath; one offers a large balcony with Intracoastal Waterway views, while the other features a private pool-view balcony. A powder bath serves the living area. A pool cabana guest suite with full ensuite bath, built-in desk and custom cabinetry offers flexibility for guests or multigenerational living. Nearby is a laundry room with dual washers and dryers. At the heart of the home is an approximately 18-foot Biancatto leathered dolomite island comfortably seating six. The chef's kitchen features Sub-Zero refrigeration, Wolf microwave, six-burner range with flat-top, dual ovens, two Bosch dishwashers, wine/beverage refrigeration, 1,000-CFM ventilation, reverse-osmosis hot/cold water faucet and custom cabinetry fabricated in the USA from German-imported materials. Biancatto leathered dolomite is carried throughout the kitchen, bathrooms, bedroom suites and outdoor kitchen. Custom-made solid oak doors were commissioned for every bedroom and closet and high-end Emtek hardware. The home opens to a covered outdoor lounge and custom dolomite outdoor kitchen with built-in BBQ, refrigerator, ice maker and sink. Ceiling fans extend throughout the residence and covered outdoor space. A large limestone patio provides additional outdoor dining. Natural limestone finishes patios, terraces, balconies, poolside areas, the outdoor gym and an exterior wall. The limestone does not get hot underfoot in the Florida sun, ideal for barefoot poolside living. Real teak is used throughout all soffits, covered patios and exterior cladding, complemented by smooth stucco, aluminum Geolam and architectural trellises. The heated saltwater pool and spa feature PebbleTec and natural stone, Pentair smart controls, LED lighting and bubblers, creating a private resort setting with the covered lounge, outdoor kitchen, cabana, gardens and outdoor gym. The residence and pool are elevated approximately 10 feet for FEMA compliance, with a privacy wall, walking path and mature landscaping. A spacious 3-car garage is designed for the car enthusiast. Additional features include five independently air-conditioned zones, triple-pane high-efficiency glazing, triple-pane PGT sliders, low-voltage smart-home wiring, Sugar Oak Natural Luxe wood flooring, oversized 4' x 4' porcelain tile, imported Plyboo wall treatments and custom artisan lighting. Furniture is available separately. An optional boat package at Safe Harbor featuring a 2023 Yamaha 25' FSH fishing boat and boat slip is also available, with slip transfer subject to marina approval.

1355 Roberts Bay Lane, Sarasota
$874,900
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
ENDLESS POSSIBILITIES ON SIESTA KEY. Welcome to 19 Whispering Sands Drive, Unit 201, an exceptional opportunity to create your own Gulf Coast retreat in one of Siesta Key’s most established beachfront communities. Whether you choose to enjoy the residence as it is, renovate it over time, or completely reimagine the interior to reflect your own style, the possibilities are nearly endless. For buyers who want a more turnkey path, a renovation package can also be made available to help transform the residence into a beautifully updated coastal home. What cannot be recreated is the setting. Whispering Sands offers approximately 800 feet of private quartz-sand beach directly on the Gulf, two heated swimming pools, a beachside Tiki Hut and grills, fitness facilities, kayak and canoe storage, shuffleboard and beautifully maintained grounds. The community continues to invest in its future, with the Clubhouse and exclusive Tower Lounge undergoing renovation and improvements throughout the property. Here, the lifestyle begins outside your door. Spend mornings along the Gulf shoreline, afternoons by the pool and evenings watching Siesta Key’s celebrated sunsets. Siesta Key Village is just moments away, putting restaurants, boutiques, entertainment and island life within easy reach. Make it your own, renovate it with our available design and renovation package, or explore its rental possibilities subject to association requirements. The location is already extraordinary. The next chapter is yours to create.

19 Whispering Sands Drive Unit 201, 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
$544,900
1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Welcome to your own slice of paradise at Jamaica Royale on world-famous Siesta Key. This beautifully updated, turnkey one-bedroom, one-bath villa offers the convenience of ground-floor living in an all-ground-level association, meaning no stairs and no milestone inspections required. Renovated in 2025, this villa is move-in ready and ideally positioned with relaxing views. Jamaica Royale is a sought-after beachfront community featuring three swimming pools, private beach access with lounge chairs, grilling areas, shuffleboard, and a variety of recreational amenities, creating the perfect setting for both relaxation and fun. Whether you're searching for a personal beach retreat or a proven investment property, this villa delivers. With a strong rental history and existing bookings, it offers immediate income potential while giving you the opportunity to enjoy the sugar-white sands and turquoise waters of Siesta Key whenever you choose. As the best-priced turnkey one-bedroom villa currently available in Jamaica Royale, this is an exceptional opportunity to own a beachfront getaway at an outstanding value. Schedule your private showing today!

5830 Midnight Pass Road Unit 43, Sarasota
$549,000
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 3rd floor condo in Sunrise Cove, offered turnkey furnished and ready for you to move in and start enjoying island life immediately. Enjoy next level comfort with a brand-new 2026 A/C system and an LED whole home in duct air purifier cool, refreshing comfort and cleaner, fresher indoor air all year long. Take in stunning back bay views from your home and enjoy an unbeatable location directly across from Turtle Beach and Park, with boat, kayak, and canoe launches, a playground, and a convenient trolley stop. Sunrise Cove delivers an exceptional amenity lineup, 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 slips are available for rent with water and electric hookups, and the community includes full-time onsite facility and maintenance managers for added peace of mind. Step outside to Turtles Pub & Café, Turtles Restaurant, and a nearby marina right next door. Plus, you’re moments away from world famous Siesta Key Beach, known for its powdery quartz sand, sparkling water, and unforgettable sunsets.

9011 Midnight Pass Road Unit 329, Sarasota
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