Siesta Key FL Real Estate, Homes for Sale With Fence - Ed Grabowski

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

$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

$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

$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

$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

$1,550,000

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

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