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$2,895,000
5 Beds ⋅ 7 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

Sarasota
$2,895,000
5 Beds ⋅ 7 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

6910 Midnight Pass Road Unit B, Sarasota
$575,000
1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an exceptional investment opportunity or personal beach vacation retreat. Perfectly positioned within the complex and just steps from the pool, this bright and modern unit features a spacious layout with a welcoming foyer (found in only select units), a large bedroom with abundant closet space, and a versatile Florida room overlooking the courtyard and pool...ideal for relaxing, morning coffee, or hosting guests. Hurricane-rated windows and doors provide peace, quiet, and year-round comfort. Enjoy resort-style amenities including two pools (one heated), tennis and pickleball courts, shuffleboard, BBQ grilling areas, picnic spaces, and lush tropical landscaping, all within a no-road-to-cross beachfront setting. Recent community upgrades include a NEW ROOF, NEW SEAWALL, landscaping, and a secure gated entry for added privacy. Additional conveniences include covered parking just steps from your door, nearby laundry facilities, onsite management, and a private mailbox. This high-demand weekly rental property offers both immediate income and future upside, with OWNER FINANCING AVAILABLE for added flexibility. Located just minutes from dining, shopping, and Siesta Key Village, with trolley access right outside, this is a rare opportunity to own a piece of paradise that seamlessly blends income potential with effortless coastal living. Seller financing and private financing available. Do NOT WAIT, it will not last long!

6006 Midnight Pass Road Unit 51, Sarasota
$6,500,000
Coral Shores SubDv. ⋅ 34242 Zip Code
Under contract-accepting backup offers. An exceptionally rare opportunity to acquire a fully renovated, income-producing, nine-unit, waterfront condominium complex located adjacent to Turtle Beach on world-renowned Siesta Key. Coral Shores offers immediate short-term rental income opportunity, paired with long-term redevelopment and appreciation potential, in one of Florida’s most supply-constrained coastal markets. Property Highlights: • Nine (9) condominium units sold as a package • Just under 0.50-acre waterfront site • Direct Sarasota Bay to Gulf of Mexico access – no bridges • Four private docks with eight slips (up to ~40’+ vessels) • Heated in-ground swimming pool • Large central parking lot for tenants and guests • Shared laundry and owner storage facilities • Predominantly 2BR units with select 1BR and studio layouts Renovations & Interior Upgrades: All units have recently completed extensive renovations featuring modern coastal interiors, updated kitchens with new appliances, stone countertops and new cabinetry, glass-enclosed contemporary bathrooms, new flooring, trim, windows, and select in-unit laundry, new common pay laundry appliances with storage closets, new raised HVAC units, new pool pump equipment, and more. The property is fully turnkey for continued short-term rental use. Income & Zoning Upside: Currently operating as weekly short-term rentals with strong seasonal occupancy. Zoned for low-rise condominiums (2–3 stories), with surrounding properties zoned mid-rise (4–6 stories), providing future redevelopment or density expansion potential subject to approvals. More detail is available with executed NDA.

9022 Midnight Pass Road, Sarasota
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Welcome to Old World Siesta Key...this 1940s Bungalow Home was converted approx 40 years ago into a Triplex and a Cottage was added at the rear of the property. Siesta Key is World Renown for it's White Powdery Sand Beaches and is so convenient to the Mainland and all the Attractions Sarasota has to offer such as the Arts, St Armands and Unbelievable Shopping. The Property is located approximately three blocks behind Siesta Key Village, the Hub of Restaurants, Nightlife, and Shops, and there you will find this Graceful Triplex and Cottage. There are several Private Patios as well as Open Areas for Outdoor Entertainment and Relaxation both in the Front and Rear of the Triplex. There are Storage Units for Each Rental and there is a Shared Laundry Area in the middle of the Backyard. Convenience is really key for this Property as you can Walk to the Beach or the Village in 15 Minutes. Island Life is Unique, Exciting, Colorful but can also be Quiet and Slow, it's the perspective of the Offering and it's a sought after way of living. For the past 20 years the units have been long term rentals. Some of the tenants have been there for years and all four would like to stay and continue their Florida Island Lifestyle. Rents shown are the Expected rents that could be charged as the Owner currently charges less... just his way of doing business. There is one option that could change the dynamics and that would be to keep the Triplex as long term rentals and use the rear Cottage as an AirBNB and Owners Use unit. This would drastically change the income stream. The water and internet/cable is currently paid for by the Owner and the Electric is split between the Tenants based on unit size, of course all of this is subject to change based on the New Owner's intentions. This is an Amazing Opportunity to have both Income and Personal Enjoyment all wrapped up with a Special Place we call Siesta Key Living!

618 Avenida De Mayo, Sarasota
$3,195,000
4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Discover an exceptional income-generating property in the heart of coveted Siesta Key right on Beach Road! This fully renovated raised multi-unit compound features a spacious 2-bedroom, 2-bathroom unit and a 2-bedroom, 1-bathrooom unit (side by side). An impressive gross income in 2023 and n 2024 (despite hurricane-related downtime), this turnkey investment provides immediate cash flow. Note: This property is zoned an RMF (Residential Multifamily) and is legally able to accept nightly rentals. The property boasts recent upgrades including new AC (2022), updated flooring (2025), modernized plumbing (2022), electrical (2022), and hot tubs (2022). This amazing opportunity is the best cap rate on any house on Siesta Key. Whether you're seeking a high-performing Airbnb rental portfolio or a strategic redevelopment opportunity in one of Florida's most desirable beach destinations, this property delivers both immediate income and long-term appreciation potential. Absentee owner managed; turnkey operation available at on a management fee with all staff staying in place. This house already has engineering drawings to enclose the bottom area adding 2,000 additonal square foot, that would increase rent by or more. This property could be purchased as a portfolio with 5228 Calle Menorca and 6550 Sabal Road.

527 Beach Road, Sarasota
$4,400,000
9 Beds ⋅ 11 Baths ⋅ Siesta Sunset SubDv. ⋅ 34242 Zip Code
5.9% Seller Financing and Nightly rentals, a unicorn. This 7-unit investment property is unique in that it operates more similar to hotel than a single family vacation rental. It has years of returning guests and it's one of very few elevated properties allowing the former mentioned, nightly rentals. 2-studios, 2-1 bedrooms, 2-2 bedrooms, and a penthouse suite with wrap around balcony. Your guests will enjoy a great pool area, sizable covered space with a grill, on site laundry, and a roof top deck. It's 1 block to both the Village and beach, guests walk everywhere. Park your car in one of the 7 newly pavered spaces and don't start it again until the vacation is over. Now for you the owner, a private office/guest check in, 2 storage areas for linens housewares etc, and a commercial laundry for turnovers. These types never trade, don't let another 20 years pass before this sells again. Cap rate and NOI is proforma

5322 Calle De La Siesta, Sarasota
$3,350,000
Siesta SubDv. ⋅ 34242 Zip Code
Discover Unrivaled Coastal Elegance Steps from Siesta Key Beach! This rare gem features two meticulously remodeled canal-front homes with stunning partial views of the bay, perfectly situated in a prestigious neighborhood. The main residence boasts a contemporary design with open and spacious layouts, highlighted by soaring 24 ft ceilings adorned with stylish gray wooden accent beams. Culinary enthusiasts will be captivated by the gourmet kitchen, featuring custom-made wood cabinets complemented by exquisite Carrara Quartz countertops. Equipped with top-of-the-line appliances, including a new stainless Thermador refrigerator, Bosch dishwasher, and an impressive center island with a bar area, it truly caters to the most discerning chefs. Zoned RMF2 while located in a single-family neighborhood, this property allows for daily Airbnb rentals, making it an excellent investment opportunity. A private, charming guest cottage serves as an ideal retreat or rental for additional cash flow. Recent upgrades include new Window World Hurricane-rated windows, French doors, and a newly installed seawall (2025), ensuring your investment remains safe and secure. The main house spans 3,005 sq ft, featuring three bedrooms and 2.5 baths adorned with luxurious Panaria marble and 24x48 tile flooring. Bathrooms boast contemporary Miseno vanities and premium Grohe and Hansgrohe fixtures. The decadent master suite invites relaxation with a rain cap shower and a sumptuous soaking tub. Both homes are equipped with new Rheem A/C units, while the property’s outdoor oasis features a large screened lanai overlooking the canal and bay. Dive into the newly resurfaced pool with a stunning stone waterfall or enjoy the expansive outdoor space, surrounded by tropical landscaping. The cozy guest cottage, covering 1,700 sq ft, includes three bedrooms and two full baths, showcasing beach-washed ceramic tile flooring, white wood Shaker cabinets, and modern KitchenAid and Bosch appliances. The new dock provides easy access to pristine boating waters with no bridges obstructing your path to the bay. Siesta Key is a haven for music lovers and foodies alike, while Sarasota delights with its vibrant art scene, ballet performances, the Asolo Performing Arts Center, the Ringling Art Museum, and world-class shopping. Relax with your favorite beverage on the rear patio, shaded by a majestic live oak, or grab your fishing rod, bathing suit, and water toys to fully embrace the Siesta Salt Life. Act fast! This exquisite property offers a luxurious lifestyle and lucrative potential in one of Florida’s most sought-after destinations!

1240 Solitude Lane, Sarasota
$2,550,000
6 Beds ⋅ 4 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
Exceptional four-unit boutique coastal hospitality investment ideally positioned directly across from PB13 public beach access on legendary Siesta Key. This distinguished property represents one of the island’s most compelling income-producing opportunities, offering immediate access to Siesta Beach, ranked the #1 Beach in America and #4 worldwide by TripAdvisor’s 2025 Travelers’ Choice Awards. Renowned for its 99% pure quartz crystal sand and vibrant turquoise Gulf waters, this iconic destination delivers an unparalleled coastal experience that drives year-round demand. The intimate complex features a desirable mix of one and two bedroom residences and is professionally managed and offered fully turnkey, with all systems, furnishings, and operational components optimized for short-term rental performance. This established, high-performing hospitality asset demonstrates strong guest appeal, repeat bookings, and the ability to command premium nightly rates, allowing a new owner to seamlessly step into a stabilized operation from day one. Guests are consistently drawn to the unbeatable across-the-street beach access, eliminating parking hassles and enhancing walkability, an increasingly rare and highly sought-after advantage that supports rate premiums throughout the year. The property’s boutique scale and coastal charm deliver the personalized, resort-style experience today’s travelers prefer, further strengthening occupancy and guest loyalty. No rental restrictions provide a critical competitive edge, offering complete flexibility to optimize booking strategies, pricing models, and minimum stays without regulatory limitations. Strong financials underscore the property’s exceptional performance. With limited comparable inventory, enduring demand for high-quality coastal accommodations, and an irreplaceable location on Siesta Key, this offering represents a rare opportunity to acquire a trophy boutique hospitality asset in one of Florida’s most coveted beach markets. The Point of Rocks location further elevates market performance, placing guests within walking distance of Crescent Village’s restaurants, shops, and boutiques, while maintaining direct proximity to one of the world’s most celebrated beaches. This is a truly exceptional acquisition for investors seeking immediate cash flow, long-term appreciation, and a premier presence in an iconic coastal destination.

6905 Point Of Rocks Road, Sarasota
$1,305,000
4 Beds ⋅ 4 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
EXCEPTIONALLY RARE Siesta Key Income Property | Zoned for DAILY Rentals — a true Siesta Key Unicorn. This rare 4-bedroom, 4-bath duplex offers a unique opportunity to acquire a short-term rental asset just a short stroll from the world-famous white sands of Siesta Key Beach, one of the most supply-constrained and consistently in-demand vacation markets in Florida. Configured as two fully renovated 2BR/2BA residences, this property delivers unmatched flexibility—ideal as a high-performing investment, 1031 replacement property, vacation home, or personal residence with income potential. Zoned for DAILY rentals—a highly limited and valuable designation on Siesta Key—the property is currently operated as a professionally managed short-term rental with future bookings in place. Designed for both guest appeal and operational efficiency, each unit features open-concept living spaces, updated kitchens, in-unit laundry, durable tile flooring throughout, and tasteful coastal furnishings. The property is being sold fully furnished and turnkey, allowing for a seamless transition of ownership with no operational downtime. Outdoor amenities further support strong occupancy and repeat bookings, including a fenced, heated pool, tropical landscaping, lounging and dining areas, and a private grilling space. Four dedicated off-street parking spaces (two per unit) add a meaningful competitive advantage in this highly desirable beach location. Professionally operated as a vacation rental since 2020, the property has achieved documented gross rental income approaching $200,000 annually. A temporary decline in late 2024 and early 2025 was event-driven rather than demand-driven, due to regional hurricane-related cancellations. Travel demand to Siesta Key is now rebounding, and bookings are steadily returning—positioning the property for revenue normalization and potential growth consistent with prior peak years. Whether you are a short-term rental investor, 1031 exchange buyer, or an owner seeking to blend lifestyle with income, this property offers a rare combination of location, zoning, resilience, and upside in one of Florida’s most desirable coastal markets. Detailed income and expense reports available upon request. Buyer to verify exchange eligibility and tax treatment with qualified advisors. Private showings by appointment only.

1123 Crescent Street Unit 1123/1125, Sarasota
$1,200,000
4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Back on the market! Beautiful triplex that went through a total renovation 2024. A re-roof project was completed in 2022 and is under a transferable warranty. Property can be rented as 3 separate units - Studio, One Bedroom, Three Bedroom. Property could easily be converted to a duplex (2 BR / 1 BA + 3 BR / 2 BA) in the event the owner prefers to live in one unit and rent the other. Just a few blocks from Siesta Village and an easy stroll to the beach, this is a great location to enjoy what Siesta Key has to offer! Total living Space - 2173 SF Main Unit - 3 BR / 2 BA - Approx - 1400 SF Second Unit - 1 BR / 1 BA - Approx. 600 SF Third Unit - Studio / 1 BR 1 BA - Approx - 200 SF Total living Space - 2173 SF Main Unit - 3 BR / 2 BA - Approx - 1400 SF Second Unit - 1 BR / 1 BA - Approx. 600 SF Third Unit - Studio / 1 BR 1 BA - Approx - 200 SF

604 Avenida De Mayo, Sarasota
$599,900
4 Beds ⋅ 4 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
An exceptional opportunity on coveted Siesta Key, this duplex property with two units is offered as-is, with flexibility to restore the existing structure or rebuild to suit your vision. Situated on an expansive lot just minutes from Shell Beach and Siesta Key Public Beach, the property offers convenient access to world-famous sand beaches, dining, and shopping. Whether you are a builder, investor, or owner looking to create a custom coastal retreat or income-producing duplex, this property presents outstanding potential in one of Florida’s most desirable island communities. All offers are welcomed and encouraged.

3615 Higel Avenue, Sarasota
$1,160,000
4 Beds ⋅ 2 Baths ⋅ Sarasota By The Sea SubDv. ⋅ 34242 Zip Code
Exceptional Investment Opportunity Awaits! Just a two-minute stroll from the stunning white sands of Siesta Key Beach, Sun & Sea Island Hideaways presents a rare chance to own a fully remodeled, high-income-producing duplex in an ideal island setting. With zoning for short-term rentals, this incredible retreat offers remarkable flexibility: live in one unit while renting the other, or maximize your earnings by leasing both units to vacationers year-round. The property is fully furnished and has future bookings in place, ensuring immediate income potential. Nestled in the sought-after south end of Siesta Key, the property exudes tropical allure with interiors featuring updated terrazzo floors, chic furnishings, and modern upgrades, including new appliances, a new roof, and new AC units for both residences. Each 2-bedroom, 1-bathroom unit is thoughtfully designed for comfort, featuring bright, open living spaces that embody the essence of island living. A shared indoor laundry area adds convenience, while an outdoor shower provides the perfect way to conclude a beach day. The expansive, fully fenced backyard is a private oasis, with lush, low-maintenance landscaping, synthetic turf, and a sizable composite deck perfect for sunset gatherings, outdoor dining, or relaxation. A nearby community pool is accessible to owners and guests, and four designated parking spaces offer added convenience for owners and visitors. With a proven track record of strong rentals and high demand from vacationers, Sun & Sea Island Hideaways is more than just a home—it’s an investment in the ultimate island lifestyle. Whether you're seeking a profitable rental property or a private sanctuary with income potential, this Siesta Key treasure is ready to fulfill your island dreams.

1141 Sun N Sea Drive, Sarasota
$3,800,000
8 Beds ⋅ 8 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
SIESTA KEY INVESTMENT PROPERTY. Great location! Welcome to the Wildflower. Just steps from the #1 Beach in USA. Nestled within a tropical oasis, this charming 8 plex 4 ground level units and 4 second level units, with 8 parking spaces offers a unique blend of comfort and natural beauty. Surrounded by vibrant tropical flora, enter the common area courtyard centered around a sparkling heated pool, perfect for relaxing after a day at the beach. The courtyard backdrop includes a standing waterfall that offers the tranquil sounds of nature. A very unique detail to any outdoor living space. Adjacent from the pool are two screened communal areas. A game room, with tv, ping pong table, pool table, arcade & washer/dryers and restroom with shower. The second lanai has a sectional sitting area with tv, fire pit and sauna. Plenty of beach and pool accessories, noodles, rafts, beach chairs, carts, etc,. for guests to enjoy. There is also a dock, across the street that is included with the sale of the property. Ideal for kayak launching or fishing. The canal leads to the Siesta Key Grand Canal. The interiors are adorned with NEW modern finishes, appliances, and furnishings. Interior spaces can be combined by interior door. Each room has been eloquently decorated with a coastal theme. Guests can take leisurely strolls to Siesta Key Village shops, restaurants and entertainment. The free trolley stop is also around the corner. This turnkey property is in like NEW CONDITION and is the perfect investment opportunity. Schedule your showing to see this amazing slice of paradise.

544 Canal Road, Sarasota
$700,000
Siesta Beach SubDv. ⋅ 34242 Zip Code
2 minute Stroll to Beautiful Siesta Key Beach! 2 Bed 1 Bath on each side. Seller pays quarterly for access to the inground pool just a few feet away as well. Nearby eating and shopping also walking distance. Lenny'z Pizza & Island Bar just a few feet away. No insurance claims or FEMA claims were made on the property. Just paid to mitigate for water damage and remove all damaged surfaces. Terrazzo floors and room for a courtyard area in the back. Indoor laundry hook up in between both units. Membership to Calini Beach club is optional but is what allows for the private beach access and the use of the pool.

1138 Sun N Sea Drive, Sarasota
$1,735,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
Location is Everything with this Fantastic Property. Only a few short steps to having your feet in the Crystal Sands of Siesta Beach and a short leisurely walk to Siesta Village. Zoned Multi-Family with NO HOA. You can rebuild one of the 1940's bungalows and repair the other two or start all over with a fresh new look. This has been a huge income producing property over the years for the owner. ***Seller is not warranting the structures on the land***

303 Beach Road, Sarasota
$2,200,000
Grand Siesta SubDv. ⋅ 34242 Zip Code
Welcome to Grand Siesta! Rarely available Opportunity! Where else on Siesta Key can you find this unique location, offering Siesta Beach Access a block away, the Siesta Village two blocks away, directly on the Grand Canal with a boat lift, while all within the weekly rental zone. Paradise awaits at this fabulous, 3 bedroom/3.5 bath luxury townhouse. This amazing, spacious, luxury townhouse draws you in with an inviting, professionally designed interior with a comfortable, coastal vibe. The home is being sold furnished. The concrete block exterior provides structural integrity. An excellent space for entertaining family & friends in your custom gourmet kitchen with gas range and open-concept living area with magnificent views. This truly extraordinary property boasts: 10 ft. ceilings, custom window treatments, Thermador appliances, porcelain tile, hardwood flooring, granite countertops, custom cabinetry, elevator service to all floors, as well as other high-end finishes. Enjoy sweeping views of the Grand Canal & fabulous sunrises from your living area & covered porches as well as the exquisite, primary suite. A boater’s dream house…water fun is guaranteed with a private, heated, saltwater pool, dock with power & water, and a 10,000 lb. boat lift. View playful manatees, jumping fish, and colorful sea birds from the covered porches. A two-car garage is a rare feature for a beach retreat. Enjoy an early morning walk or bike ride on the beach, take a quiet kayak ride or paddle board in the canals or on the beach, watch the beautiful sunrises on your covered porch, or just relax in your private pool. Perfectly located on the Grand Canal, while just one block to the powdery, crystal sands & turquoise waters of Siesta Key Beach. You’ll love strolling to the Iconic, Siesta Village where you’ll enjoy a variety of restaurants, live music, dancing, shopping or just sipping margaritas at happy hour. It’s the perfect trifecta for location. When not using as your own personal retreat, the weekly rental opportunity can generate income to offset expenses. This coastal sanctuary offers an unsurpassed lifestyle for anyone looking for their own piece of Island Paradise! Considered the cultural gem of Florida’s West Coast, you’ll be only 5 miles from wonderful cultural and social activities in Downtown Sarasota. You’ll fall in love with this exquisite , tranquil, Canal Front Property on Siesta Key whether it’s your winter escape, family getaway, or permanent residence. Embrace Your Beach Life! What are you waiting for?

447 Canal Road Unit 447, Sarasota
$1,125,000
Point Of Rocks SubDv. ⋅ 34242 Zip Code
Exceptional investment opportunity in a prime location! Just steps away from the iconic Siesta Key Beach, this property is zoned for residential multi-family use and offers excellent short-term rental potential with a 7-day minimum. Imagine building a brand-new, high-earning duplex to generate steady income all year. County approval is already secured for a new duplex, and the current structure is set up as a duplex house with separate electrical panels and two private lanais. The property sustained significant flood damage from the recent hurricanes, resulting in the removal of all kitchen appliances. It currently requires extensive repairs, or you have the option to start fresh with a complete rebuild. The oversized pool adds fantastic appeal and convenience, complete with a recently installed motor, and the fully fenced backyard offers a private oasis for relaxation. With two generous driveways that fit up to 10 cars, plus a paved backyard perfect for gatherings and entertainment, this property is designed for relaxation. The property is in walking distance from the beach. Siesta Key enjoys a strong vacation rental market as the top-rated beach in the U.S., investment properties are in high demand. Vacationers enjoy the free Siesta Key Breeze Trolley that stops just next door and offers transportation to the Village. This is the most competitively priced multi-family property on the Key—don’t let this incredible opportunity pass by!

1132 Crescent Street, Sarasota
$569,000
1 Beds ⋅ 1 Baths ⋅ Ebbtide SubDv. ⋅ 34242 Zip Code
Investor Alert! Let the numbers do the talking. *Gross revenue after tourist taxes was $71,189. *Occupancy in ’23 was 45 weeks. *All expenses are $19.1k, giving you a net of $52.4k, that’s a cap rate of over 9. EBBTIDE has some of the lowest HOA dues on the Key, and is one of the few properties on the Key that allow One Day Minimum Rentals - no need to miss a revenue producing day. Now for what you get. *A 600 sq ft 1 bedroom with 1 full bath with a washer/dryer. *Was renovated in 2020 with a new kitchen and furniture. The patio is 240 sq ft, and has a dedicated outdoor shower. It has deeded gulf beach access and use of the Association by the Sea heated saltwater pool. What the renters say – ‘Fantastic location’, ‘We love this spot’, 'Perfect Siesta Key getaway’. Check out the reviews on Airbnb- 202 reviews that average 4.95 out of 5! The location is outstanding. Ebb Tide is directly across Midnight Pass Rd from the Crescent Club, Capt. Curt’s, the Daiquiri Deck and everything in the south village. You can walk everywhere! The Siesta Key Trolly stops feet from your door, giving you a FREE ride to the north village and many other places on the Key. No need for a car here. This is perfect for an owner/operator or seamlessly fold it into your current rentals. Bookings so far this year are $61,142 (including $10K for the remainder of 2024, with 130 days to go. Call now to view this outstanding rental unit.

6610 Midnight Pass Road Unit 11, Sarasota
$1,200,000
Sarasota By The Sea SubDv. ⋅ 34242 Zip Code
Welcome to your dream investment opportunity! This stunning duplex, ideally situated in a highly sought-after vacation destination, offers an exceptional chance to own a lucrative income-producing property. With modern amenities, stylish interiors, and a prime location, this property is perfect for vacation rentals, ensuring high occupancy rates and excellent returns. This exceptional property, featuring two newer A/C units (2022), a new water heater (2025), and a durable metal roof, promises both comfort and peace of mind. This turnkey duplex has been extensively renovated in 2025, featuring brand-new kitchens with modern cabinetry, countertops, and appliances, as well as updated electrical and plumbing systems for worry-free ownership. The metal roof has been professionally inspected and maintained, ensuring its durability and optimal condition for long-term reliability. Additional upgrades include stylish contemporary furnishings, making this property a fully equipped, move-in-ready investment opportunity. The one-bedroom, one-bath residence exudes charm with its contemporary kitchen and bath, tile floors, washer and dryer outside, and cozy living space, making it perfect for a single occupant or couple. The two-bedroom, two-and-a-half-bath townhome-style residence, spread over two levels, offers spacious living with wood floors upstairs, updated bathrooms, a modern kitchen, tile floors downstairs, and a laundry room for additional washer and dryer, ideal for families or larger groups. Outdoor living is a delight with low-maintenance landscaping, a generous patio area, and a private, gated backyard. The shared screened porch entry adds to the property's charm and functionality, while outside parking accommodates up to five cars. Residents could enjoy the heated pool and deeded beach access just one block away, offering the ultimate in convenience and leisure. Positioned within close proximity to shopping and restaurants, this property ensures that all your needs are met. With a proven rental history, this duplex is perfect for vacation rentals, promising excellent returns for the savvy investor. Experience the best of Siesta Key living at 6630 Midnight Pass Rd, where every detail has been curated for an exceptional coastal lifestyle. This duplex is a proven income producer with an established rental history and strong demand from vacationers year-round. The current owner has also used the property for family stays, suggesting that even higher income could be achieved with more dedicated rental availability. Don’t miss this rare opportunity to own a piece of paradise with outstanding income potential.

6630 Midnight Pass Road, Sarasota
$1,630,000
4 Beds ⋅ 4 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
A must see duplex situated on Siesta Key where the ' Number 1' beach in the world is located. This complex is within a 5 minute walk on Crescent Street to a public access. The double 2 bedroom/2 bath unit comes 'turn-key' furnished and ready for occupancy. The present owners family has owned it since it was built in 1969 and kept it well maintained. The second unit has not been rented and only occupied by family and friends. The property is within walking distance to restaurants , boating, shopping and the Siesta Trolley stops. The Trolley will take you to SIESTA VILLAGE (no charge) where you can enjoy more shopping, restaurants and Kilwins ice cream store. They also make stops at Siesta Key beach which has been chosen as the NUMBER 1 beach in the world many times. The sand on this beach is white quartz and is very fine. Downtown Sarasota (CBD) excels in fine dining along with Van Wezel Performing Arts Hall, Sarasota Opera, The Players Studio plus Selby Botanical Gardens, Burns Court area, John Ringling Museum/House and much more. West of downtown is the famous St Armands for shopping/dining, Lido Beach, Mote Marine Laboratory and Aquarium. Sarasota International Airport (SRQ) is only a couple of mies from downtown. Great opportunity to own an excellent income property or family compound on Siesta Key.

1131-1133 Crescent Street, Sarasota
$4,000,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
Featuring the highly coveted RMF zoning, this property offers legal short term rentals-a rarity across the region and a game-changer for income potential. Set on high ground, it has proven its durability by remaining high and dry during recent hurricanes, providing unmatched security and peace of mind. The property comes fully turnkey furnished, ensuring a seamless and effortless transition to ownership. As we look toward the future, this property stands as the Crown Jewel of assets on Siesta Key, a rare gem built to endure the test of time while offering unmatched beauty, functionality, and investment opportunity. With its robust construction, prime location, and exceptional earning potential, this property truly embodies the future of Siesta Key real estate. A smart investment that delivers both safety and style, it’s your chance to own a slice of paradise that pays for itself.

645 Beach Road, Sarasota
$1,550,000
5 Beds ⋅ 5 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Create income in this three-unit property. Turnkey and ready to rent daily or weekly. Completely remodeled-2 swimming pools.

5408 Plaza Des Las Palmas, Sarasota
$1,400,000
Island House SubDv. ⋅ 34242 Zip Code
INVESTOR ALERT! Rarely available 4 bedroom, 3 bath villa at Island House on Siesta Key. This fabulous duplex consists of two units; the upper unit is 2 bed/1 bath, and the lower unit is 2 bed/2 bath. Both were completely renovated in 2017 with state-of-the-art stainless appliances & farmhouse sinks, subway tile backsplashes, and custom shaker cabinets. There is crown molding throughout, ceiling fans in all rooms, plantation shutters, and wood-look ceramic tile floors creating a warm, chic living space that will make you feel right at home. There are spacious lanais on both units and the second-story unit overlooks the Olympic-sized swimming pool with a clubhouse that offers a pool table, ping pong table, and air hockey. A two-car carport is included as well as a private laundry room and additional storage room. This 73-unit complex has great amenities, including a private beach, cabanas, beach chairs, shuffleboard, and gas grills. Pets are not allowed but short-term rentals are. This duplex has a myriad of options for how it is used. Either or both units could be rented when not in use by the new owners, either together for a family gathering or as two separate units. Conveniently located about 1 mile from all the south Siesta restaurants and shopping and about 2 miles from Siesta Key Village and all it has to offer. Don’t feel like walking? Take the Free Shuttle to your favorite Siesta Key dinner spot. Downtown Sarasota is just 7 miles away with live theatre, museums, ballet, opera, and lots of great restaurants.

6150 Midnight Pass Rd Unit 40 A&B, Sarasota
$5,475,000
11 Beds ⋅ 10 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
Emersed in a lush oasis-like setting, Siesta Key Inn is an enchanting experience of luxurious leisure with an island resort ambiance. The dream vacation lifestyle is a reality with full-service amenities complemented by tranquil tropical views afforded nearly every residence while being mere seconds away from the soft powdery sands of Siesta Beach. Comprised of eight one- and two-bedroom units, impeccable improvements and design aesthetics throughout meet even the highest standards. Each residence includes a full kitchen, quality finishes of Quartzite countertops, soft-close wood cabinetry, Moen and Kohler fixtures, Jacuzzi jetted tubs, upscale crown molding and LED lighting, and an inside washer and dryer to establish a true sense of home. Feel rest assured that Siesta Key Inn has been built to exceed expectation for security and comfort with prestressed concrete walls and floors with whisper mat rubber membranes between the floors, Pex plumbing, multiple tankless water heaters with natural gas and multiple electric water heaters, open-cell foam insulation in the attic, Square D electric panels, Eco-flow water filtration systems, and hurricane impact windows and doors. The property has been thoughtfully designed for you to enjoy opportunities of serene indulgence where you can lounge by the expansive pool boasting therapy jets and waterfall features, a nearby grilling area, gazebo and bike rack. To make your beach adventures all the better, there are beach chairs, umbrellas, towels and coolers to use as well. Explore the sights and attractions of Siesta Village just beyond the beach and journey over the bridge to fall in love with downtown Sarasota.

1125 Point Of Rocks Road, Sarasota
$570,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
TOTALLY REMODELED KEYWEST STYLE SIESTA DUPLEX WITH GARAGE FOR EACH SIDE.INCLUDES LAUNDRY AREA. BRAND NEW SOLAR HEATED POOL AND DECKING. LOTS OF UPGRADES. NEW ROOF, NEW VINYL SIDING, NEW LANDSCAPING. M ANAGEMENT IN PLACE-PROJECTED 2001 INCOME - $75,000 - GROSS - NET APPROXIMATELY $55,000.CALL LISTER FOR PACKAGE. (BOOKED THROUGH MAY 2001 AT $1,300 WK.)

312-314 Canal Road, Sarasota