Sarasota/Crescent Beach/Siesta Key Homes with Private Mailbox Exterior Features

Sarasota/Crescent Beach/Siesta Key Homes with Private Mailbox Exterior Features

Welcome to the enchanting shores of Siesta Key, nestled in the heart of Sarasota County, Florida. Known for its powdery white sand beaches and stunning turquoise waters, Siesta Key is a tropical paradise that offers a unique blend of relaxation and vibrant coastal living. With its charming neighborhoods, including the serene Crescent Beach, this idyllic region is perfect for those seeking a tranquil escape or an active lifestyle filled with outdoor adventures.

Siesta Key boasts an array of luxurious homes, many featuring private mailbox exterior options that enhance the charm and character of each property. Imagine pulling up to your beautiful beachside retreat, greeted by your very own distinctive mailbox, a personal touch that reflects your style and welcomes you home. These homes are designed to offer both comfort and elegance, often showcasing lush landscaping, modern amenities, and breathtaking views of the Gulf of Mexico.

Beyond the stunning properties, Siesta Key is a vibrant community where residents enjoy an array of recreational activities, from paddleboarding and kayaking to beach volleyball and sunset strolls along the shore. The local dining scene is equally inviting, with a variety of restaurants serving fresh seafood and local cuisine, perfect for a night out or a casual gathering with friends.

Whether you’re looking for a permanent residence or a vacation getaway, Siesta Key offers a unique lifestyle that combines the beauty of nature with the charm of a close-knit community. Discover your dream home with a private mailbox and make Siesta Key your own slice of paradise.

Newest Sarasota/Crescent Beach/Siesta Key Homes with Private Mailbox Exterior Features

310 Avenida Milano, Siesta Key
$1,100,000
3 Beds ⋅ 2 Baths ⋅ A4712120 MLS
Boater's paradise meets Village convenience in this premier Siesta Key waterfront property. Tucked away on a tranquil, low-traffic dead-end street just off Ocean Boulevard, this rare canal-front lot offers the ultimate canvas for custom coastal luxury. It represents a premier opportunity to build a private estate or complete a major renovation just steps from the heart of Siesta Key Village. Boasting 75 LINEAR FEET OF DIRECT CANAL FRONTAGE with immediate access to Sarasota Bay, the property is tailored perfectly for a true waterfront lifestyle. The location delivers the perfect balance of peaceful privacy and effortless daily convenience. Enjoy an easy stroll to the island's celebrated shops, vibrant dining, and nightlife, while keeping world-famous Siesta Key Beach just minutes away. Waterfront lots this close to the Village rarely come to market. Whether you are an investor looking to capitalize on premium island real estate or a buyer ready to design a personalized coastal retreat, this property provides the perfect foundation. Schedule your private viewing today to explore the endless possibilities. A 1% RATE BUY-DOWN IS AVAILABLE TO QUALIFIED BUYERS WHO WORK WITH THE SELLER'S PREFERRED LENDER.

310 Avenida Milano, Siesta Key
316 Beach Road, Siesta Key
$5,199,000
8 Beds ⋅ 10 Baths ⋅ A4712016 MLS
Experience elevated coastal living just steps from the shoreline at 316 Beach Road, an exceptional eight-bedroom Siesta Key retreat offering deeded beach access, panoramic Gulf views, and an established history as a high-performing vacation rental. Completely remodeled in 2021, this three-level residence combines modern coastal design with spacious accommodations and thoughtfully designed indoor-outdoor living. A private elevator connects all levels, while multiple Gulf-facing balconies capture sweeping water views and unforgettable sunsets. The fourth-floor main living area serves as the heart of the home, featuring an open-concept kitchen, dining area, and gathering space that flows onto an expansive balcony overlooking the Gulf. Each of the eight bedrooms features a private ensuite bathroom, offering comfort and privacy for family and guests. An additional club room with a wet bar provides another inviting space to entertain, while the outdoor retreat features a private pool, integrated spa, lush tropical landscaping, and a fully equipped outdoor kitchen with a built-in grill, refrigeration, and dining area. Ideally located near Siesta Key Village and the world-famous shores of Siesta Beach, this property offers convenient access to dining, shopping, and entertainment. With a proven rental history generating approximately $400,000 to $500,000 annually, 316 Beach Road presents a rare opportunity to enjoy the best of Siesta Key living while benefiting from exceptional income potential.

316 Beach Road, Siesta Key
5534 Cape Leyte Drive, Siesta Key
$1,549,000
3 Beds ⋅ 4 Baths ⋅ A4707910 MLS
LOCATION, LOCATION, LOCATION!!! STEPS TO THE BEACH....YOUR FURNISHED SIESTA KEY ESCAPE—BEAUTIFULLY REIMAGINED This extensively and tastefully renovated 3 bedroom, 3 and 1 half bath with quality finishes throughout has been meticulously maintained and is being offered furnished. This 2300 square feet under air, a 2 car garage and large pool with panoramic screened cage residence welcomes you with tropical landscaping, a circular paver driveway, and an inviting island style. Renovated in 2017–2018 this home offers a relaxed living space that with substantial improvements throughout. Each bedroom features its own private en suite bathroom, complemented by a separate guest half bath. All bathrooms were completely redone during the renovation. Improvements included a new metal roof, PGT WinGuard Aluminum 700 Series impact windows throughout, all new doors, plumbing, electrical, air-conditioning and ducts, drywall, lighting, insulation and tile flooring. The kitchen features white cabinetry, a contrasting island with seating, and an impressive appliance selection: a Thermador gas stove and oven/microwave combination, Bosch dishwasher, and Café refrigerator. A 250-gallon propane tank supplies the gas stove and tankless water heater. Open living and dining spaces provide a welcoming setting for entertaining, with warm-toned tile flooring and views of the surrounding greenery. Outside, the pool, paver deck, and lanai invite relaxed outdoor living. A Panoramic View pool enclosure enhances the outlook, creating a beautiful setting for morning coffee, poolside dining, and quiet afternoons. Additional conveniences include central vacuum throughout the home, wiring for ceiling fans in every room, and an oversized two-car garage. Thoughtfully updated with quality finishes throughout, this welcoming Siesta Key retreat is ready for your next chapter of island living.

5534 Cape Leyte Drive, Siesta Key
3441 Gulfmead Drive, Siesta Key
$10,500,000
6 Beds ⋅ 7 Baths ⋅ A4711149 MLS
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, Siesta Key
8800 Midnight Pass Road, Siesta Key
$3,588,000
4 Beds ⋅ 5 Baths ⋅ A4710718 MLS
With gulf sunset views, and 3-minute walkable private beach access, this New Construction Modern Beach House on Siesta Key mixes a sought-after location with modern luxury. Experience the best of coastal living in this brand-new 4 bed, 4.5 bath home with walking access to Turtle Beach and a marina just one minute away. With 3,676 SF of thoughtfully designed space, this home offers ocean views throughout, multiple outdoor patios and terraces, rooftop deck, and seamless indoor-outdoor flow. Feel the sea breeze in the spacious backyard, including a pool, hot tub, and outdoor kitchen. Enjoy light-toned engineered hardwood floors, a chef’s kitchen with top-tier appliances, and spacious en-suite bedrooms, including a stunning primary suite with a private terrace and spa-like bath. Additional features include a 3-car garage, and 6 covered carport spaces for recreational utility vehicles such as, jet skis, golf carts, or a boat, with easy gate access. Enjoy an elevator included layout, and high-end finishes throughout—all just minutes from Siesta Village’s shops and dining. This newly built residence offers peace of mind with the latest in building codes, energy efficiency, and storm protection. Modern insulation, impact-rated windows and doors, and up-to-date mechanical systems translate into lower utility bills, reduced maintenance, and enhanced safety. You’ll also benefit from turnkey readiness—no need for costly renovations or updates. Whether for full-time living or a coastal getaway, this is Siesta Key luxury at its finest.

8800 Midnight Pass Road, Siesta Key
8569 Midnight Pass Road, Siesta Key
$7,450,000
4 Beds ⋅ 5 Baths ⋅ A4710584 MLS
This private waterfront estate on Siesta Key combines modern Mediterranean architecture, beautifully updated interiors, and sweeping views of Little Sarasota Bay to create an exceptional coastal retreat. Set on over an acre of lush property behind a gated entrance and winding pavered driveway, this custom residence offers more than 100 feet of direct bay frontage, exceptional privacy, and unobstructed boating access to Sarasota Bay and the Intracoastal Waterway. Built in 2012 and extensively refreshed, the home encompasses more than 6,000 square feet of living space, four en-suite bedrooms, a four-car split garage, and an impressive collection of indoor and outdoor entertaining spaces. Offered fully furnished with contemporary pieces throughout, this remarkable home is ready for immediate enjoyment. A dramatic entry introduces soaring cathedral ceilings, a neutral color palette, and walls of floor-to-ceiling glass framing the waterfront. The grand living room features a fireplace and spectacular two-story windows, while the adjoining formal dining room provides an elegant setting for entertaining. Tile flooring complements the main living level, with beautiful hardwood flooring upstairs. The light-filled gourmet kitchen features quartz countertops, custom cabinetry, all-white appliances, gold fixtures, oversized center island, separate breakfast bar, dual built-in ovens, six-burner gas cooktop, and concealed 6-by-10-foot walk-in pantry. The adjoining informal dining area and spacious family room create an inviting gathering space overlooking the bay. Walls of pocketing glass sliders open completely to the covered outdoor cabana and fully equipped summer kitchen, seamlessly connecting indoor and outdoor living. Privately positioned on the main level, the beautiful primary suite features peaceful water views, an oversized dual walk-in closet, and a luxurious marble-appointed bathroom. A nearby office/den offers a quiet retreat, while private access to the pool deck enhances the suite's connection to the outdoors. A secluded second en-suite bedroom with its own exterior entrance provides an ideal arrangement for guests or extended family. The first-floor laundry room offers generous built-in storage. Upstairs, two spacious bedroom suites feature hardwood flooring, walk-in closets, updated en-suite bathrooms, and private balconies overlooking Little Sarasota Bay. An additional bonus room with dual closets and a wet bar overlooks the dramatic living room below and offers flexibility as a fifth bedroom, media room, or additional office. Outside, lush tropical landscaping surrounds an expansive pavered pool deck with a heated swimming pool, raised spa, and covered outdoor living area. A waterfront firepit, private basketball court, and extended dock with a 20,000-lbs. lift complete this exceptional setting. Boaters will appreciate the property's 103 feet of shoreline and direct access to the open waters of Sarasota Bay. Recent improvements include a new roof in 2025, three updated bathrooms, and HVAC replacements in 2024 and 2022. Ideally situated on Siesta Key, this private bayfront estate offers convenient access to Siesta Key Beach, Turtle Beach, Siesta Key Village, and the island's waterfront restaurants and recreational opportunities, just minutes away. Nearby mainland destinations include Downtown Sarasota, Marina Jack, Selby Botanical Gardens, renowned theaters, galleries, and cultural attractions.

8569 Midnight Pass Road, Siesta Key
838 Norsota Way, Siesta Key
$4,190,000
5 Beds ⋅ 7 Baths ⋅ A4710682 MLS
Under Construction. To be complete in a few months. Discover timeless coastal elegance in this upcoming traditional-style new construction home, perfectly situated in the highly coveted Bay Island neighborhood on Siesta Key. Designed to blend modern sophistication with classic charm, this residence offers an extraordinary lifestyle of luxury and tranquility. Set on a 13,815-square-foot homesite, this 3,001-square-foot residence features 5 spacious bedrooms, 5 full bathrooms, 2 half baths, an office, the opportunity for a private fitness studio, and 3 garage spaces. Thoughtfully curated interiors showcase refined finishes, soaring ceilings, and abundant natural light. At the heart of the home lies a gourmet chef’s kitchen with a striking quartz waterfall island, elegant pendant lighting, and custom cabinetry. The premium appliance suite includes a 72-inch Sub-Zero refrigerator, Cove dishwasher, and Wolf range, coffee maker, and microwave. The adjoining living and dining areas flow seamlessly outdoors. Step into a private tropical retreat featuring an elevated pool deck with a resort-style pool and champagne spa, a spacious outdoor patio, and a covered outdoor kitchen. Surrounded by lush landscaping and swaying palms, the patio offers ample room for outdoor dining, entertaining, and relaxing by the pool. Located in one of Sarasota’s most desirable neighborhoods, this remarkable new construction home offers privacy, convenience, and effortless access to world-class beaches, fine dining, and vibrant cultural attractions. A rare opportunity to own a brand-new luxury residence on Bay Island—where coastal beauty meets timeless design. Includes artist’s rendering of proposed completed residence.

838 Norsota Way, Siesta Key
120 Whispering Sands Drive Unit V20, Siesta Key
$725,000
3 Beds ⋅ 3 Baths ⋅ A4707425 MLS
RARELY AVAILABLE & EXQUISITELY REMODELED! Discover an exceptional 3 bedroom/3 bath freestanding villa with 2-car garage in Whispering Sands, Siesta Key’s coveted resort style GULF FRONT community on 800’ of private beach! Completely gutted and reimagined in 2016, this remarkable residence showcases creative design, quality finishes, and meticulous attention to detail throughout. An impressive 1,640 square feet of interior living space unfolds beneath soaring vaulted ceilings, with an open concept layout designed for effortless living and entertaining. The expansive 16' x 22' living room is delightfully complemented by sophisticated indirect LED illumination. Beautiful ceramic plank flooring flows throughout. The spacious entertainer’s kitchen combines style and function with granite countertops, a generous breakfast bar, soft close cabinetry & pullout drawers, LG and Bosch stainless appliances, and recessed and pendant lighting. The spacious primary suite offers two closets – a custom walk-in and a separate built-in. The third bedroom could also easily function as a home office, featuring a built-in desk, shelving, and custom closet. All three beautifully remodeled bathrooms feature granite counters, soft close cabinetry, tiled glass-enclosed walk-in showers, recessed lighting, and/or skylights. Two out of three bathrooms are ensuite — a rare advantage. All 2016 hurricane impact windows and sliders. Extend your entertaining outdoors into the private fenced brick paver patio, complete with a gas grill, with propane tank and gas hookup. The epoxy finished 2-car garage includes a full size LG washer and dryer, utility sink, workbench and shelving – and plenty of space for your bikes and beach essentials. Enjoy the Whispering Sands lifestyle. Just around the corner from famous Siesta Key Village, this 55+ Gulf front community includes 800’ of private quartz sand beach, two heated pools, clubhouse (currently undergoing complete remodeling), beachside Tiki Hut, shuffleboard, and canoe/kayak storage. Don’t miss this distinctive villa offering exceptional space, privacy, and effortless coastal living!

120 Whispering Sands Drive Unit V20, Siesta Key
1260 Dolphin Bay Way Unit 301, Siesta Key
$1,750,000
3 Beds ⋅ 3 Baths ⋅ A4707069 MLS ⋅ 1260 BLDG.
Experience refined waterfront living at Dolphin Bay, an intimate, pet-friendly community of just 50 residences on Siesta Key. Beautifully redesigned with a sophisticated coastal aesthetic, this exceptional three-bedroom, three-bath condominium offers nearly 2,500 square feet of beautifully appointed living space and captivating views of the Intracoastal Waterway. Bright, open interiors create an effortless sense of space, with 9-foot ceilings, elegant plank tile flooring, custom built-ins and beautifully updated baths. At the heart of the residence, an impressive chef's kitchen makes a striking statement with expansive countertops, generous gathering spaces, custom cabinetry and premium Sub-Zero, Monogram and Viking appliances. A dramatic six-foot, built-in double-door wine cellar adds a distinctive touch for entertaining. The spacious living and dining areas flow beautifully toward the waterfront, where walls of glass frame the Intracoastal views. An expansive, air-conditioned enclosed lanai extends the living space, creating an inviting year-round retreat for relaxing, entertaining or simply watching the boats pass by. Thoughtful details include custom cabinetry, recessed lighting and integrated theater speakers. The generously sized bedrooms and spa-inspired baths offer comfort and privacy for family and guests. Recent improvements include impact-resistant windows and sliding doors installed in 2025, along with custom motorized light-filtering and room-darkening shades. Additional updates include the HVAC system (2020) and water heater (2021). A private one-car garage beneath the building adds convenience and additional storage. Residents of Dolphin Bay enjoy an inviting coastal lifestyle with a beautifully updated clubhouse, fitness center, Har-Tru tennis courts, heated pool and spa, and a day dock for boating and fishing. Siesta Key's world-renowned white-sand beaches and the restaurants, boutiques, and entertainment of Siesta Village are just minutes away, with convenient trolley access. Combining beautifully curated interiors, remarkable waterfront views and easy elegance of island living, this is an exceptional opportunity to enjoy Siesta Key at its finest.

1260 Dolphin Bay Way Unit 301, Siesta Key
809 Idlewild Way, Siesta Key
$3,850,000
4 Beds ⋅ 5 Baths ⋅ A4708479 MLS
Completely remodeled from top to bottom and expanded with a new 1,200 square foot, two-level addition, 809 Idlewild Way is a one of one contemporary waterfront oasis offering the look, feel and comfort of a new home in a prime Siesta Key location. Set on a high elevation site that sustained zero water damage during the 2024 hurricanes, this boater’s paradise occupies a coveted cul-de-sac with 109 feet of water-frontage on the Grand Canal. The comprehensive renovation includes new electrical and plumbing, new HVAC systems, impact windows and doors, premium interior finishes and extensively redesigned outdoor living spaces. Extensive structural improvements opened the living room, kitchen and covered patio toward the water, removing obstructing columns and preserving uninterrupted views across the pool and waterfront. Expansive sliders surrounding the primary suite bring in natural light and further connect the room to the water. The renovation carries through the exterior, where lush landscaping, integrated architectural lighting, a distinctive pergola entry, standing seam metal roof and stone fascia reinforce the home’s modern architectural character. Inside, premium engineered hardwood flooring, custom tray ceilings with integrated designer lighting, meticulous level 5 drywall and masterfully executed finish carpentry create a sophisticated interior. The gourmet kitchen features custom cabinetry and natural quartzite surfaces, complemented by additional custom bar cabinetry and entertaining space in the dining area. Beautifully appointed bathrooms are extensively wrapped in tile with dramatic glass shower enclosures. The home is offered furnished and move-in ready. Resort style outdoor living, created with entertaining in mind, centers around a new saltwater pool with a sun shelf, integrated fire and water features, a sealed paver deck, outdoor kitchen and gathering spaces overlooking the waterfront. A custom U shaped dock with a 24,000lb boat lift, power, softened water and lighting completes the boating experience, with Sarasota Bay just a short boat ride away. The seller’s Formula boat is also available for purchase separately. A new elevated seawall cap and reinforcing wall, 500 gallon underground propane tank and whole home generator add comfort and resilience. All of this is complemented by the beaches, dining and relaxed island lifestyle that make Siesta Key such a distinctive place to call home.

809 Idlewild Way, Siesta Key
1256 Riegels Landing Drive, Siesta Key
$1,845,000
3 Beds ⋅ 4 Baths ⋅ A4708748 MLS
Designed by Sarasota School of Architecture.

1256 Riegels Landing Drive, Siesta Key
6204 Midnight Pass Road Unit 205, Siesta Key
$775,000
2 Beds ⋅ 2 Baths ⋅ A4708621 MLS ⋅ 6204 BLDG.
Welcome to Siesta Dunes! This bright and airy second-floor end-unit condominium offers a wonderful combination of comfort, updates, and location, with peaceful garden views and a peek-a-boo view of the Gulf. High ceilings and an abundance of natural light create a spacious, open feel throughout the residence, while new hurricane-impact windows provide added peace of mind. The roof and air conditioning system are also newer. The two bed, two bath layout features an updated kitchen with ample counter space and a convenient dinette area. The spacious living room opens through sliding glass doors to the balcony, extending the living space outdoors and providing a pleasant spot to enjoy the surrounding views. The primary suite offers a walk-in closet and ensuite bath, while the additional guest bedroom and full bath provide comfortable accommodations for family and friends. The desirable gulf front community of Siesta Dunes offers a saltwater pool & spa, tennis and pickleball courts, a beach deck and pavilion, carports, additional storage and small pets are allowed. Weekly rentals are also permitted, making this an appealing opportunity for those looking for a vacation home with rental potential or an investment property. With easy access to the renown Siesta Key Village, where you can enjoy the tropical ambiance of dining, shopping, and entertainment as well as everything Sarasota has to offer including the arts and culture of downtown. Whether you're looking for a place to enjoy yourself or an opportunity to generate rental income, this Siesta Dunes residence offers the flexibility, updates, and location to enjoy the best of the Florida lifestyle.

6204 Midnight Pass Road Unit 205, Siesta Key
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