Siesta Key Real Estate

Siesta Key Real Estate

Welcome to Siesta Key, Florida – a tropical paradise nestled in Sarasota County that epitomizes the allure of coastal living. Renowned for its powdery white sands and crystal-clear waters, Siesta Key boasts some of the most beautiful beaches in the United States, making it a haven for sun-seekers and water enthusiasts alike.

Siesta Key is not just about its stunning shoreline; it offers a vibrant community filled with charming boutiques, delightful restaurants, and lively nightlife. Stroll through the quaint village, where you can indulge in fresh seafood, shop for unique souvenirs, or enjoy a refreshing cocktail as you watch the sunset paint the sky in hues of orange and pink.

For nature lovers, Siesta Key is a gateway to outdoor adventures. Kayak through the mangroves, explore the local wildlife at the nearby parks, or take a leisurely bike ride along the scenic paths. The island's warm climate allows for year-round enjoyment of activities such as paddleboarding, fishing, and beach volleyball.

Families will appreciate the excellent schools and safe neighborhoods, making Siesta Key not only a vacation destination but also an ideal place to call home. With a strong sense of community and a laid-back lifestyle, residents enjoy a perfect blend of relaxation and recreation.

Whether you’re looking to invest in a vacation home, retire in paradise, or simply explore the beauty of Siesta Key, this enchanting island offers a unique lifestyle that captures the essence of Florida living. Discover your piece of paradise today!

Newest Listings in Siesta Key

523 Beach Road, Sarasota
$8,249,000
19 Beds ⋅ 12 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
EXCLUSIVE SIESTA KEY INVESTMENT OPPORTUNITY | 9 INCOME-PRODUCING RENTAL UNITS | 7+ Percent CAP RATE | STEPS from SIESTA KEY BEACH! An exceptional opportunity to acquire TWO adjacent income-producing properties at 523 BEACH ROAD and 530 CANAL ROAD, ideally located just a one-minute walk from Siesta Key Beach and five minutes from the vibrant Siesta Key Village. The portfolio comprises 9 established vacation rental units, including 7 on Beach Road and 2 on Canal Road, accommodating couples, families, and larger groups. Significant improvements have enhanced both properties, with five of the nine units reportedly fully renovated and additional upgrades completed through 2025. Key features include: modernized interiors, kitchens, and appliances, new HVAC systems installed in 2025, impact-resistant windows, heated swimming pool and tropical landscaping, private outdoor areas, BBQ facilities, and outdoor showers, 25+ parking spaces, complimentary beach amenities. This is A TURNKEY HOSPITALITY INVESTMENT. The properties offer an established short-term rental operation with professional management, strong visibility across major booking platforms, and a history of returning guests. Combining an exceptional location, recently upgraded accommodations, and an attractive 7+ Percent CAP rate, this portfolio presents a compelling opportunity to invest in one of Florida’s most desirable vacation destinations. Financial statements, operating performance, and supporting documentation are available to qualified buyers upon execution of a Non-Disclosure (NDA).

523 Beach Road, Sarasota
5760 Midnight Pass Road Unit 109, Sarasota
$1,289,000
3 Beds ⋅ 2 Baths ⋅ Gulf N Bay SubDv. ⋅ 34242 Zip Code
Rarely available and highly sought after, this beautifully renovated 3-bedroom, 2-bath residence is one of only a handful of lobby-level condominiums within Gulf & Bay Club. Perfectly positioned to capture expansive water views, the home offers breathtaking vistas from nearly every room, overlooking lush manicured grounds, serene lakes, and beautiful Gulf views stretching toward the horizon. The ever-changing backdrop of water, tropical landscaping, and coastal skies creates a sense of tranquility that is uniquely Gulf & Bay. A comprehensive floor-to-ceiling renovation has transformed the residence into a sophisticated coastal retreat. The living area was thoughtfully expanded to maximize both space and scenery, creating an open, light-filled environment where the spectacular views remain the focal point. With no elevator required and convenient access to the beach, pools, and community amenities, this coveted ground-floor location offers a level of accessibility and ease rarely found on Siesta Key. Lovingly maintained by its owners and never rented, the residence reflects pride of ownership throughout. Behind the beautiful finishes lies an extensive list of meaningful improvements, including impact-resistant windows and doors, a new HVAC system, luxury vinyl plank flooring, custom shades, and newer appliances, including a washer, dryer, garbage disposal, and a beverage/wine cooler at the dining area's dry bar, the perfect spot to prepare sunset cocktails and appetizers before heading out to enjoy another beautiful evening on Siesta Key. Offered turnkey furnished, this condo is ready to be enjoyed from day one. Brand-new La-Z-Boy furnishings enhance the living room, while carefully selected Pottery Barn pieces create a bright, serene atmosphere in the primary suite. The third bedroom features custom built-in cabinetry and provides office space including a full-size bed for guests. The spacious second guest bedroom comfortably accommodates two queen-size beds and includes built-in storage designed to maximize both function and comfort. Gulf & Bay Club offers a true resort-style experience set along 800 feet of private beachfront on world-famous Siesta Key Beach. Residents enjoy a beautifully maintained, gated community with on-site maintenance and an exceptional array of amenities, including three heated swimming pools, tennis and pickleball courts, fitness facilities, saunas, two clubhouses, beach chair service, and recently updated landscaping, fencing, beach enhancements, electric charging stations and grilling areas. Surrounded by tropical landscaping, scenic lakes, fountains, and winding pathways, Gulf & Bay delivers the atmosphere of a luxury coastal resort while offering the comfort and convenience of home. Location is key here, so close to shopping, dining, downtown Sarasota, the airport, and so much more! Need to head to Siesta Key Village for some fun? Hop on the free trolley; your possibilities are endless! Whether you're seeking a full-time residence or a seasonal escape, this exceptional property offers a rare combination of panoramic water views, extensive upgrades, turnkey convenience, and an unmatched Siesta Key lifestyle.

5760 Midnight Pass Road Unit 109, Sarasota
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
5880 Midnight Pass Road Unit 706, Sarasota
$1,250,000
2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
Experience ultimate coastal luxury at Casarina, ideally situated directly on the quartz-white sands of award-winning Crescent Beach. Welcome to Unit 706, a phenomenal 7th-floor residence offering wonderful elevated sightlines, a recently and tastefully remodeled interior, and the quintessential Siesta Key beachfront lifestyle. This thoughtfully maintained building provides exceptional resort-style amenities, including a heated beachfront swimming pool, soothing hot spring spa, clubhouse, fitness room, tennis courts, and private beach access. Boasting a perfect mid-Key location, you are just moments away from local island dining, boutiques, and convenient mainland access via the Stickney Point Bridge. Don’t miss this premier island opportunity.

5880 Midnight Pass Road Unit 706, Sarasota
6157 Midnight Pass Road Unit E24, Sarasota
$474,000
1 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
Elevated living awaits in this beautifully appointed 4th-floor condo, located just minutes from the quartz sands of Siesta Key Beach. This turn-key residence offers a seamless blend of relaxed Florida style and incredible investment potential. The bright, airy interior is flooded with natural light, leading out to an east-facing screened balcony that overlooks lush, tropical landscaping. This condo features durable ceramic tile flooring throughout the main living areas, a well-equipped kitchen with stainless steel appliances, and a generous walk-in pantry. Storage is effortless thanks to a separate large closet designed to house all your beach and pool gear. Recent mechanical updates, including a brand-new water heater and a newer A/C system, for greater peace of mind. Positioned as a premier vacation destination, this property allows for weekly rentals, offering a fantastic opportunity to offset ownership costs with gross rental income ranging from $30,000 to $40,000 annually. Residents enjoy access to a resort-style community pool, tennis courts, a social room, and a fishing pier. The unit includes one assigned covered parking space along with ample guest parking. Whether you are looking for a personal getaway or a high-performing rental, this condo delivers the ultimate coastal lifestyle.

6157 Midnight Pass Road Unit E24, Sarasota
1430 Point Crisp Road, Sarasota
$15,995,000
4 Beds ⋅ 7 Baths ⋅ Point Crisp SubDv. ⋅ 34242 Zip Code
Move Right In! One of a kind turnkey waterfront home with water views from every room in the house and over 800ft of waterfront on the private oasis. Tucked away near the end of Point Crisp Road, where Siesta Key narrows into Little Sarasota Bay and feels like an island of its own, this 2022 custom residence occupies a truly distinctive waterfront setting. As the second-to-last home on Point Crisp, the property offers a remarkable sense of privacy, sweeping water views and nearly three-quarters of an acre in one of Siesta Key’s most unique locations. Offering 5,301 square feet under air and 12,497 square feet under roof, with four bedrooms, six full baths and one half bath, the home combines newer construction with a setting that is increasingly difficult to replicate. Built by D.E. Robinson Construction Group, the interiors flow naturally toward the water. Corner pocket sliders open the main living area outdoors, while the kitchen features Thermador appliances, wood cabinetry and a hidden walk-in pantry. A wine bar with wine refrigerator and ice machine complements the entertaining spaces, along with whole-home surround sound and custom lighting. A dedicated office with pocket doors enjoys water views and connects to an ensuite bath that also serves the pool. All three guest suites are thoughtfully positioned on the main living level, with every bedroom offering an ensuite bath for comfortable and private accommodations for family and visitors. Upstairs, the owner’s suite is positioned on the sunset side as a true retreat. Separate his-and-hers bathrooms and walk-in closets create distinct personal spaces, with her bath featuring a soaking tub and his closet incorporating a second washer and dryer. Between the two bathrooms, a private outdoor space opens toward the water. Outside, a 54-foot infinity saltwater pool and spa anchor the outdoor living experience. An outdoor kitchen, generous decking, landscaped grounds and a lawn area along the water create multiple spaces for dining, lounging and entertaining. Although only a few years old, the home has received more than $1.3 million in major updates and improvements. New seawalls along the front and rear enhance the waterfront, while a dock with electrical service and a 30,000-pound boat lift complete the boating setup. The residence is offered fully furnished, with a boat and jet skis included for a truly turnkey Siesta Key lifestyle. The expansive 4+ car garage configuration adds flexibility, with generous vehicle space, built-ins and ample first-level storage. Air-conditioned garage areas add comfort and function, while the central garage can serve as a game room, hobby space or additional conditioned area and connects directly to the larger garage. A whole-home generator, water treatment system and elevator add everyday convenience. Direct lower-level access leads outside to an outdoor shower, ideal after time at the pool or on the water. What makes this property exceptional is the way everything comes together: newer construction, thoughtful interiors, extensive improvements, serious boating infrastructure, and water views that are difficult to replicate. From the office and guest suites to the owner’s retreat, pool, lawn and dock, the water remains part of the experience. This is one of those Siesta Key properties that simply has to be seen in person to fully appreciate.

1430 Point Crisp Road, Sarasota
8773 Midnight Pass Road Unit 302G, Sarasota
$500,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
WELCOME TO PARADISE AT ISLAND REEF! This beautiful condo at 8773 Midnight Pass Road, Unit 302-G, is your opportunity to experience the ultimate Siesta Key lifestyle! Located in the desirable Island Reef community, this incredible Gulf-to-Bay property offers the perfect combination of island charm, relaxation, and resort-style living. Enjoy an amazing selection of community amenities, including two heated swimming pools, private beach access, tennis and pickleball courts, a fitness center, clubhouse, game room, library, shuffleboard, boat docks, fishing pier, kayak launch, and grilling areas! There's always something to enjoy, whether you're soaking up the Florida sunshine, getting out on the water, staying active, or simply relaxing with friends and neighbors. And the location? Absolutely fantastic! Just moments from beautiful beaches, wonderful restaurants, shopping, parks, and everything that makes Siesta Key one of Florida's most desirable destinations. Whether you're searching for your forever home, a seasonal escape, or your own tropical getaway, this is an opportunity to make those Florida dreams come true. At Island Reef, every day feels like a vacation! Come see why you'll want to call this incredible community HOME!

8773 Midnight Pass Road Unit 302G, 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
5174 Sandy Cove Avenue, Sarasota
$1,975,990
Sara Sands SubDv. ⋅ 34242 Zip Code
This oversized cul-de-sac lot has just been cleared and is currently permitted and the slab has been poured. In addition a new 275 foot seawall has also been completed along with a dock and 10,000 lb boat lift. This lot is ready for your new home plans or use the existing plans that have been permitted and approved. Plans with existing builder can be taken over if desired or design your own home with your builder. Your back yard has south west exposure and plenty of room for 1 more boat lift if desired. Currently permitted for a 3700 square foot 4 bedroom 4 bath home. Don't miss this homesite with close proximity to the north village and all that Siesta Key has to offer. The last picture shows the proposed home that is permitted. This could also be changed.

5174 Sandy Cove Avenue, Sarasota
6287 Midnight Pass Road Unit 106, Sarasota
$630,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
PRICED $30,000 LESS THAN LAST APPRAISAL REPORT (May 2026). Enjoy the best of the Siesta Key lifestyle at Excelsior Beach to Bay! This beautifully appointed 2-bedroom, 2-bath condominium features new plank tile flooring throughout the main living areas, with traditional tile flooring in both bathrooms. Hurricane-impact windows provide additional piece of mind. Residents enjoy deeded access to world-famous Siesta Key Beach, along with beautifully maintained tropical grounds and an impressive array of resort-style amenities. Relax by either of the two community pools, stay active on the tennis and pickleball courts, or take advantage of the fitness center, shuffleboard and outdoor grilling stations. Additional amenities include a community room, library and convenient on-site management. Each building offers assigned covered parking with ample additional parking for guests. An additional storage unity provides convenient space for beach chairs, bicycles, and all you beach essentials. Whether you're looking for a full time residence, a seasonal getaway, or an investment opportunity, Excelsior offers exceptional flexibility. Ideally located near Siesta Key's beautiful beaches, popular restaurants, shopping and entertainment, this is an opportunity to enjoy the very best of coastal Florida living!

6287 Midnight Pass Road Unit 106, Sarasota
1200 Cove Ii Place Unit 832, Sarasota
$549,900
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
Turnkey 2BR/1.5BA Condo with Stunning Water Views – Steps from Crescent & Siesta Beaches! Welcome to your slice of paradise! This beautifully maintained 2-bedroom, 1.5-bath condo sits on the 3rd floor, directly across from the sugar sands of Crescent Beach and just a short stroll to world-famous Siesta Beach. Enjoy breathtaking views overlooking the marina and Intracoastal Waterway from your private balcony—perfect for morning coffee or sunset cocktails. Located in the highly sought-after Midnight Cove II, this community offers a vibrant coastal lifestyle with low maintenance fees that include Cable TV and Fiber Internet. No special assessments or surprises here as the community maintains fully funded reserves and passed the milestone inspection without missing a beat. Whether you're lounging at the heated pool, hitting the tennis, pickleball, or basketball courts, or simply soaking up the community vibe, there's something for everyone here. Offered turnkey furnished and priced to sell, this is a rare opportunity to own in one of the area's most desirable waterfront communities. Don't miss your chance to live the beach life or invest in a prime rental property!

1200 Cove Ii Place Unit 832, Sarasota
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