Siesta Key Homes with Private Mailbox Exterior Features

Siesta Key Homes with Private Mailbox Exterior Features

Welcome to Siesta Key, Florida—a stunning barrier island located in Sarasota County, known for its powdery white sand beaches and vibrant coastal lifestyle. Nestled along the Gulf of Mexico, Siesta Key is not just a paradise for beach lovers; it’s a community rich in culture, outdoor activities, and a laid-back atmosphere that makes it a sought-after destination for both residents and vacationers alike.

Siesta Key boasts a variety of homes, each with its own unique charm. One of the standout features of many properties here is the presence of private mailboxes, adding a touch of individuality and convenience to your residence. Imagine coming home to a beautifully landscaped yard where your personalized mailbox greets you, enhancing the curb appeal of your home while providing a sense of privacy and ownership.

The architectural styles of homes in Siesta Key range from luxurious beachfront estates to cozy bungalows, each designed to complement the natural beauty of the island. Many properties feature outdoor spaces perfect for entertaining, with patios that overlook serene gardens or the sparkling waters of the Gulf.

Living in Siesta Key means embracing a lifestyle filled with sun-soaked days at the beach, fishing, boating, and exploring the vibrant local dining scene. With its friendly community and breathtaking views, Siesta Key is not just a place to live; it’s a way of life. Discover your dream home with a private mailbox in this enchanting coastal haven today!

Newest Siesta Key Homes with Private Mailbox Exterior Features

3936 Hamilton Club Circle Unit 6, Sarasota
$1,400,000
3 Beds ⋅ 4 Baths ⋅ Hamilton Club SubDv. ⋅ 34242 Zip Code
Siesta Key,exclusive gated community of only 18 homes with deep water marina,pool, and tennis court all within a private, lush, tropical paradise . Walking paths around a central lagoon , as well as a beautifully maintained boardwalk of Ipe wood bordered with mangroves , are among the things that make Hamilton Club so very special . Inspired by the architecture of Bermuda with its close ties to 17th Century Great Britian is recognized by its striking pastel colored walls and "welcoming arms"staircases . Very close to the Village and Crescent Beach yet equally convenient to Downtown Sarasota. This sophisticated townhome has been renovated with fine finishes , wood and stone are incorporated in a wonderfully artistic way. Soaring ceilings and a Southern exposure provide amazing ,cheerful lighting . Fabulous center island in a truly stunning kitchen with expansive counter space, premium appliances and elegant custom cabinetry .Large walk in pantry .

3936 Hamilton Club Circle Unit 6, Sarasota
1300 N Portofino Drive Unit 102, Sarasota
$449,995
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
THE SIESTA KEY LIFESTYLE, ALL IN ONE EXCEPTIONAL WATERFRONT COMMUNITY! Imagine starting your day with coffee overlooking a picturesque harbor, spending the afternoon with your toes in Siesta Key’s powdery white sand, and gathering with friends for sunset cocktails as another spectacular Florida day draws to a close. Welcome to Siesta Harbor Condominiums Association, a vibrant 55+ community where boating, beach days, and an inviting social scene come together in one extraordinary island setting. DIRECT WATERFRONT LIVING! Perfectly positioned on the ground floor, this beautifully updated, fully furnished 2-bedroom, 2-bath residence feels more like a private coastal home than a condo. Forget elevators and stairs - simply walk through your front door with groceries or beach bags and you’re home! Inside, a bright, breezy interior features attractive tile floors throughout and an open layout designed for easy entertaining. The remodeled kitchen is a showpiece, with gorgeous granite countertops, crisp white cabinetry, stainless steel appliances, a stylish glass backsplash, a generous breakfast bar opening to the living room, and the everyday luxury of a KITCHEN PANTRY—all with gorgeous views of the harbor! The living room flows into a spectacular glass-enclosed lanai, where walls of impact-resistant glass sliders frame intimate views of the harbor, lush tropical grounds, and boats gently resting along the waterway just beyond your windows. Imagine lingering here with a good book, watching the boats drift by, or savoring an evening cocktail in your own waterfront retreat. Two welcoming bedrooms include a flexible guest room with a Murphy bed, ideal for visitors or a home office. Updated bathrooms include a bidet toilet in the primary suite. Impact glass, tasteful furnishings, a private LOCKED STORAGE CAGE just down the hall, and on-site laundry and covered parking are welcome perks. Beyond your front door, the Florida lifestyle unfolds! Boaters will love the harbor's DIRECT INTRACOASTAL WATERWAY ACCESS WITH NO BRIDGES, situated just north of the South Bridge no-wake zone for convenient cruises south toward Venice. Imagine stepping aboard your boat just outside your home and setting off for a day on the water (slips subject to availability). Beach lovers will treasure DEEDED BEACH ACCESS directly across the street at Crescent Arms, opening the door to Siesta Key’s world-famous white quartz sand and sparkling Gulf waters. Spend sun-drenched afternoons by the community pool, relax in the hot tub, or enjoy the clubhouse, fitness center, library, billiards, and lively social activities. One of Siesta Harbor’s most cherished traditions is sunset happy hour on the waterfront sunset deck, where neighbors gather to toast another beautiful evening in paradise. Tucked into a peaceful waterfront setting, Siesta Harbor is just moments from South Siesta Key Village, with its grocery store, restaurants, bars, and charming boutiques. The nearby South Bridge makes mainland Sarasota wonderfully accessible, while the Breeze transit stops right in front of the clubhouse for a convenient way to explore the island. Whether your perfect day means cruising the Intracoastal, strolling the beach, sharing sunset cocktails, or simply relaxing beside the water, this is more than a condominium—it’s your invitation to live the SIESTA KEY LIFESTYLE you’ve always imagined! WHERE ELSE can you enjoy waterfront living and resort-style amenities under $500K on Siesta Key?

1300 N Portofino Drive Unit 102, Sarasota
5215 Calle De Costa Rica, Sarasota
$1,175,000
4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
LOCATION AND CHARM!!! Welcome to 5215 Calle De Costa Rica, a single-family home located in Siesta Key, FL just steps away from the highly desired Siesta Key Beach and Village. This charming cottage offers an unbeatable location along with 1,762 square feet of living space featuring 3 bedrooms and 2 bathrooms. The main house can have one interior door closed which creates a private mother-in-law suite with its own exterior entrance. In addition to the main house there is a quaint separate guest house that offers ample space for family and friends, an office or a creative space as a studio. The entire property is fenced and feels like its own private oasis surrounded by lush tropical landscaping and generous private outdoor spaces with brick paths and patios to enjoy your morning coffee or relax in a fabulous serene environment. Inside this 6-room property you will find luxury custom ceramic tile throughout and tongue-and-groove walls and ceilings. The many windows allow in plenty of gorgeous natural light, making every room bright and welcoming. New HVAC in main house in 2024 as well as kitchen flooring. You will also appreciate the quiet street where neighbors often gather while walking their dogs while being only 5 blocks to shopping, dining and the fantastic nightlife that Siesta Key Village offers. Just a half mile walk to Sunset Pier or Beach Access #7 and the powdery quartz sands of the top-rated Siesta Key Beach. This home is perfect as a primary residence, a vacation/second home or a fabulous opportunity as an investment property. Don't miss the opportunity to own this rare and special Siesta Key Cottage located in the most coveted of locations. Bring your bikes and beach chairs because this home offers endless possibilities and the Siesta Key lifestyle offers so much to be explored and enjoyed!!

5215 Calle De Costa Rica, Sarasota
546 Freeling Drive, Sarasota
$12,500,000
5 Beds ⋅ 7 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Expected to be complete in 3–4 months. Discover an extraordinary opportunity to own a new construction waterfront residence on an expansive 0.52-acre double lot on North Siesta Key. Designed and built by Pham Development, this single-story, transitional modern-style home offers 170 feet of deep-water canal frontage, 4,353 square feet under air, and 15,453 square feet under roof. Featuring 5 bedrooms, 5 full bathrooms, 2 half baths, a designated private office, and the option for a private fitness studio, the residence showcases soaring 17.5-foot vaulted ceilings, a striking glass wine wall, and designer finishes. Light-filled interiors capture tranquil water views, while lush landscaping across the canal—with no homes visible—creates a serene, private backdrop. Opportunities to customize finishes and style allow you to make the home your own. Designed for both everyday comfort and entertaining, the open-concept living spaces center around a chef’s kitchen featuring a 72-inch Sub-Zero refrigerator, Cove dishwasher, and Wolf range, coffee maker, and microwave. The living areas flow seamlessly onto an expansive back patio equipped with remote-controlled electric mosquito screens, allowing you to enclose the space at the touch of a button. A spectacular pool with a champagne hot tub spa, generous outdoor lounging areas, and a fully equipped Wolf outdoor kitchen create an inviting setting for alfresco dining and waterfront entertaining. The primary suite offers a private sanctuary with spa-inspired amenities and thoughtfully designed personal spaces. An elegant circular driveway creates a grand arrival, while the expansive ground level offers room for up to 10 cars, complemented by an impressive 10-car garage—ideal for collectors or additional storage. Combining exceptional canal frontage, peaceful views, and beautifully appointed indoor and outdoor spaces, this distinctive North Siesta Key residence offers refined coastal living.

546 Freeling Drive, Sarasota
4644 Higel Avenue, Sarasota
$6,300,000
4 Beds ⋅ 6 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Expected to be completed in a few months, this new construction North Siesta Key residence blends innovative design, exceptional craftsmanship, and timeless coastal elegance. Designed and built by Pham Development, the home offers 3,482 square feet of living space and is nestled on a nearly 14,000-square-foot lot with 118 feet of prime canal frontage, a waterfront backyard, and a private boat dock. Featuring 4 spacious bedrooms, 4 full and 2 half beautifully appointed bathrooms, and a 3-car garage, this residence is thoughtfully designed for both comfort and style. At the heart of the open-concept layout is a well-appointed kitchen featuring a stunning quartz island with waterfall edges, elegant pendant lighting, and sleek custom cabinetry. An exceptional appliance package includes a 72-inch Sub-Zero refrigerator, Cove dishwasher, and Wolf range, coffee maker, and microwave, making this space ideal for everyday living and entertaining. Light-filled living areas maximize the beautiful water views and provide a seamless connection to the outdoors. Step outside to a private oasis, where a resort-style pool and lush landscaping create a tranquil retreat framed by swaying palms and shimmering waters. An outdoor kitchen provides the perfect setting for alfresco dining and entertaining. A private boat dock with a 10,000-pound lift and seating area invites days on the water and relaxed evenings along the canal. Located in one of Sarasota’s most desirable neighborhoods, just a short distance from world-class beaches, fine dining, and entertainment, this extraordinary property offers an exceptional blend of privacy, convenience, and waterfront luxury.

4644 Higel Avenue, Sarasota
310 Avenida Milano, Sarasota
$1,100,000
3 Beds ⋅ 2 Baths ⋅ Siesta Manor SubDv. ⋅ 34242 Zip Code
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, Sarasota
316 Beach Road, Sarasota
$5,199,000
8 Beds ⋅ 10 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
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, Sarasota
5534 Cape Leyte Drive, Sarasota
$1,549,000
3 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
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, 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
8800 Midnight Pass Road, Sarasota
$3,690,000
4 Beds ⋅ 5 Baths ⋅ Tortoise Estates SubDv. ⋅ 34242 Zip Code
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, Sarasota
8569 Midnight Pass Road, Sarasota
$7,450,000
4 Beds ⋅ 5 Baths ⋅ Saah Sub SubDv. ⋅ 34242 Zip Code
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, Sarasota
838 Norsota Way, Sarasota
$4,190,000
5 Beds ⋅ 7 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
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, Sarasota
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