Siesta Key Real Estate

Waterfront Homes for Sale in Siesta Key, FL

Welcome to your dedicated resource for waterfront homes for sale in Siesta Key, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Siesta Key, FL agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the waterfront properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Siesta Key, FL

Be the First to Know About New Siesta Key Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Siesta Key Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Waterfront Homes for Sale in Siesta Key, FL

$2,550,000
2 Beds ⋅ 3 Baths ⋅ A4692379 MLS ⋅ Ten35 BLDG.
This version sells privacy, scarcity, design, and effortless service first. The rental history supports the value proposition without cheapening the residence. A rare opportunity within Ten35 Seaside, the newest boutique Gulf-front community on South Siesta Key. Residence #308 offers an elevated coastal lifestyle defined by contemporary design, exceptional amenities, private beach access, and the personalized atmosphere discerning buyers seek from an intimate luxury property. This beautifully appointed 2-bedroom, 2.5-bath residence pairs refined interiors with effortless lock-and-leave living. An open, light-filled floor plan features Wolf and Sub-Zero appliances, custom cabinetry, designer finishes, and expansive sliding glass doors that extend the living space onto a private terrace. The spacious primary suite is a serene retreat with a spa-inspired bath and walk-in closet, while the guest suite—enhanced by custom built-in bunk beds—provides stylish flexibility for family and guests. Ten35 Seaside delivers a resort-caliber experience with direct private beach access, a Gulf-front pool and spa, fitness center, private cabanas, and a more intimate alternative to Siesta Key’s larger condominium communities. Its coveted south-key location offers convenient access to Siesta Key Village, acclaimed dining, shopping, boating, and downtown Sarasota. Beyond its lifestyle appeal, the residence offers compelling financial flexibility. It generated more than $164,800 in gross rental income and has already recorded over $101,000 in 2026, providing documented performance that may help offset ownership expenses while preserving the opportunity for personal enjoyment. For the buyer seeking a beachfront retreat, second residence, or luxury property with established rental demand, Residence #308 presents a distinctive combination of newer construction, boutique exclusivity, Gulf-front amenities, and proven income performance in one of Florida’s most celebrated coastal destinations. Buyer shall independently verify rental policies and income history, association information, room dimensions, and all property details deemed material.

1035 Seaside Drive Unit 308, Siesta Key
$2,499,000
2 Beds ⋅ 3 Baths ⋅ A4672742 MLS ⋅ Ten35 Seaside BLDG.
Experience beachfront ownership that works for you. Residence 404 at Ten35 Seaside offers a rare opportunity to own a fully operational, income-producing property on Siesta Key’s Crescent Beach — one of the most sought-after vacation rental destinations in Florida. This residence is enrolled in the community’s on-site professional rental management program, providing immediate revenue and eliminating the uncertainty, setup time, and operational burden typical of vacation rental ownership. Owners benefit from a true turnkey investment: marketing, guest services, housekeeping, and day-to-day management are handled on-site, allowing you to generate income while still reserving personal use. Inside, the unit is designed specifically for both durability and guest appeal. Floor-to-ceiling hurricane-rated glass fills the open living space with natural light, while porcelain wood-look flooring, custom finishes, and curated furnishings create the upscale coastal experience today’s renters actively seek and review highly. The kitchen features quartz countertops and premium Wolf appliances, opening seamlessly to the living area — ideal for group stays and longer bookings. The flexible floor plan maximizes occupancy potential, with a spacious primary suite, guest bedroom, and an integrated Italian fold-down bed system that expands sleeping capacity without sacrificing aesthetics — an important driver of rental performance. The private covered lanai captures panoramic Gulf views, a major booking advantage and one of the most requested amenities among Siesta Key vacationers. Ten35 Seaside functions as a boutique resort for guests and owners alike, offering: • Direct beach access to Crescent Beach • Gulf-front pool and spa • Private cabanas • Fitness center • Fire pit and gathering areas • Daily beach chair and umbrella service Rental parameters allow one-week minimum stays in the off-season and two-week minimums during peak season, striking an ideal balance between revenue generation and property preservation. Located moments from Siesta Key’s South Village dining and shopping, the property consistently attracts repeat visitors — a key factor in maintaining strong occupancy. Whether you are expanding a portfolio, completing a 1031 exchange, or seeking a vacation home that offsets ownership costs, Unit 404 offers a combination rarely found on Siesta Key: Gulf-front location, professional management, and immediate rental income from day one.

1035 Seaside Drive Unit 404, Siesta Key
$2,490,000
3 Beds ⋅ 4 Baths ⋅ A4684184 MLS ⋅ Casarina BLDG.
You will be WOWED! by this Furnished 2400+ Sq Ft of Elegant BEACHSIDE LIVING with (3) Generously Sized Bedrooms & (3.5) Baths with STUNNING FINISHES THROUGHOUT!.....RARELY AVAILABLE Corner Unit in this Special Boutique Community---a Resort-Style PET FRIENDLY "low density" plush 7 acre residential complex with over 200 feet of Powdery Quartz sand frontage along with "Old Florida" Clubhouse; Courts; Beachside Pool & Cabanas and an Onsite Manager....Upon Entrance you will be Greeted with a Grand Hallway that leads to a BRIGHT & SPACIOUS Floor Plan, reminiscent of a Single Story Home...Each Bedroom is Privately Located, each with it's own Full Baths....ENTERTAINING is "Extra Special" with Expansive Living Areas and Ideally Centrally Located Wet Bar....WELL-APPOINTED INTERIORS, including: Porcelain Tile throughout; Quartz Countertops; Hurricane Impact Windows/Sliders; "Hotel Style" Primary Suite with Seating Enclave & Sumptuous Ensuite Bath; Abundant Storage & Closet Space; In-Unit Laundry and Importantly...ease of Indoor/Outdoor Living with Multiple Sliders leading to "Wrap-Around" Balcony/Lanai--Perfect for Morning Coffees or Indulging your Favorite Cocktails while Watching Majestic Sunsets over the Gulf....*****Deeded Beach Access, convenient for long strolls collecting Seashells or just "Toes in the Sand" relaxing at Top Rated Siesta Key Beach. Dining/Shopping and Nightlife of the main village are just minutes away...GARAGE PARKING...---Ideal as Second Home/Vacation, Investment or Year-Round Residence. Island Living @ It's Finest!

5880 Midnight Pass Road Unit 511, Siesta Key
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.