Refine Search
Map
Sort by
$1,305,000
4 Beds ⋅ 4 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
EXCEPTIONALLY RARE - A Siesta Key Unicorn! This 4-bedroom, 4-bath property offers the opportunity to use as a Personal Residence (perfect for multi-generation living), Vacation Home or Duplex. This property is zoned for DAILY rentals, making it ideal for AirBNB! Just a short stroll to the world-famous sugary white sands of Siesta Key Beach, this charming coastal gem is beautifully renovated, decorated in soft beach-inspired hues with comfortable furnishings, tropical décor, and easy-maintenance tile flooring throughout. Designed for both lifestyle and performance, the property is being sold fully furnished and turnkey. Outside, enjoy a fenced, heated pool area surrounded by lush tropical landscaping that creates a private oasis for relaxation. The pool area offers brand-new lounge chairs, a grilling area, and outdoor dining for six—perfect for entertaining guests or unwinding after a day at the beach. There are four assigned parking spaces directly in front, adding convenience for owners and guests alike. This property offers exceptional flexibility and appeal. It is currently being professionally managed as a duplex with future bookings in place and a strong rental history. Whether you are looking for a personal residence for multi-generational living, a place to live AND generate rental income, or a high-performing short-term rental investment, this is it! The property is currently managed by a professional local vacation rental company, making ownership seamless and low-stress. Located close to shopping, dining, trolley stops, South Siesta Key Village, and more, this is a prime location that continues to attract repeat visitors year after year. Call now to schedule a private showing of this must-see property.

1123 Crescent Street Unit 1123/1125, Sarasota
$690,000
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
Enjoy this ultimate beach getaway and investment opportunity! This updated 2-bedroom 2 bath townhome is located directly across from Siesta Key beach and offers a generous split-bedroom and bi-level layout. Featuring high ceilings, a large light-filled eat-in kitchen, inside laundry, separate dining and living room areas and a spacious balcony overlooking the serene lake. The master bedroom suite also opens onto a balcony and includes an en-suite bathroom with ample closets and a dressing area. Our House at the Beach allows for weekly rentals, making for fantastic investment potential, or a perfect place to call home. New Hurricane Impact windows and sliding glass doors are being scheduled for installation at the Lake Houses. The central location on Siesta Key is unbeatable, and with your own garage, beach parking will never be a concern again. Simply load your beach cart and enjoy the breathtaking sunsets or catch the Siesta Breeze Bus to Siesta Village, South Siesta or Downtown Sarasota. Our House at the Beach is a well-maintained complex with a heated swimming pool, two tennis courts, pavilion, grilling area, and on-site rental management. Just minutes from Siesta Key Village where you can explore a variety of restaurants and shops. This unit is not only a perfect beach escape but also a smart investment opportunity.

1159 Lake House Circle Unit C120, Sarasota
$670,000
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
Price Drop of 20K - best price for a Tower Unit in Our House at the Beach !Strong Rental Income – Across from Siesta Beach! Totally updated 2 bed / 2 bath condo in the West Tower of “Our House at the Beach”, directly across from Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor in 2024. This second-floor unit offers incredible natural light and nearly 270 degrees of wraparound views thanks to 46 feet of sliding glass doors in the living and dining areas. This unit is turnkey furnished (excluding some artwork and personal items) and features luxury plank vinyl flooring throughout, with updated bathrooms and a gorgeous, remodeled kitchen with granite countertops, stainless steel appliances, and a pass-through to the main living area. The spacious primary bedroom offers abundant windows and a bright, airy feel. Both bathrooms have been tastefully upgraded. Enjoy two oversized balconies, perfect for relaxing after a day at the beach or hosting guests. This is not just a beach retreat—it’s a solid investment: • $32,900 gross rental income in 2023 • $28,000 in 2024 (despite storms) • Projected $40,000+ in 2025 with owner use! Weekly rentals allowed, boosting occupancy and revenue potential. The $45,000 special assessment (impact glass & more) is fully paid by the seller. Community amenities include: • Heated pool • 2 tennis courts • Grilling pavilion • Assigned covered parking • In-unit full-size washer/dryer • Pet-friendly (owners may have 1 pet up to 15 lbs) Units in the West Tower rarely come on the market—last year’s sale went for significantly more. This is your chance to own a beautifully maintained, income-producing condo across from one of the world’s most beautiful beaches!

1001 Beach Road Unit A203, Sarasota
$2,535,000
4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Welcome to “Villa del Roble” (Oak Villa) on Siesta Key’s Grand Canal—a true boater’s dream and an elevated waterfront residence that remained free of flooding during recent hurricanes. Timeless elegance and refined sophistication hallmark this thoughtfully remodeled home, beautifully preserving its authentic old world charm and offering 3,200+ square feet on two floors, including four bedrooms, an office, and three full and one-half baths. A masterpiece of craftmanship, this light-filled home showcases soaring ceilings, walls of windows, and expansive outdoor living spaces. And with over 70 feet of water frontage on the coveted Grand Canal, a 10,000-lb lift, two davits, and a Trex dock, the property provides effortless boating access directly from your backyard. Enjoy the heated pool and spa, intimate al fresco dining, a charming Tiki Hut, and a serene courtyard anchored by the majestic oak tree that inspired the home’s name. The remodeled kitchen shines with Sub-Zero and Thermador appliances, a gas cooktop, pendant lighting, stone countertops, and a well-appointed pantry – ideal for any culinary enthusiast. The sunroom, filled with natural light, has a convenient wet bar and offers peaceful canal views. The elevated main-level primary suite includes private outdoor access, a generous walk-in closet, and a spa-inspired bathroom with dual vanities, a soaking tub, and a walk-in shower. A dedicated office and powder bath complete the main floor, while three additional bedrooms (one that could serve as a secondary primary) and two full bathrooms upstairs provide ideal accommodations for family and guests. Conveniently located near Out-of-Door Academy and minutes from Siesta Key Beach, Siesta Key Village, and Sarasota’s world-class dining and shopping, this home combines exceptional boating amenities, elevated construction, and refined coastal living in one of Sarasota’s most coveted waterfront settings.

4757 Higel Avenue, Sarasota
$1,200,000
2 Beds ⋅ 2 Baths ⋅ Siesta Breakers SubDv. ⋅ 34242 Zip Code
Rare, exquisitely curated beachfront condo on Siesta Key. This lightly used - meticulously cared for - end unit home has never been rented, although the community allows much desired weekly rentals generating healthy investment income. Located on Crescent Beach, known for its tranquil beach vibe, enjoy 300 feet of prime location deeded beach access with quartz-crystal, powder-soft fine white sand that remains cool even on the hottest days. This two-bedroom, two-bath condo has been renovated and designed with an upscale and sophisticated feel within a light and airy beach home. All furnishings, accessories, dishes and linens included in this TURNKEY FURNISHED condo. The open floorplan is perfect for entertaining family and friends. The resort feel primary bedroom includes a large walk-in closet and oversized bathroom. The second bedroom has been redesigned to comfortably sleep 4 with ample storage. The living room, primary bedroom and balcony all feature stunning views of the beach, gulf and Siesta’s spectacular sunsets. This condo is in Siesta Breakers, a gated complex within easy walking distance of dining, shopping, and a full-service marina with boat rentals. Play a game of tennis or pickleball on the two community courts. Leave your car at home and walk or take the free Trolley to nearby Siesta Key Village. This ideal location features easy access on and off the Key allowing more time to enjoy your coastal waterfront living. Welcome home to Siesta Key.

6480 Midnight Pass Road Unit 211, Sarasota
$500,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
Major Price Reduction for this buildable lot.... New Years Resolution.. Build the Dream House on Siesta Key!!! Seize this rare opportunity to own a ready-to-build lot just steps from Siesta Key Village in one of the island’s most sought-after locations! Why You'll Love This Property: ~Cleared & Ready to Build – No demolition needed—just bring your vision to life! ~Flexible Use – Ideal for a luxury residence, vacation retreat, or high-income rental. ~Prime Location – Walk to Siesta Key Village for dining, shopping, and entertainment. ~Beach Life Awaits – Minutes from Siesta Key Beach, known for its powder-soft quartz sand & breathtaking sunsets. Whether you're dreaming of an elegant coastal oasis or a savvy investment property, this blank canvas is waiting for you. Don’t miss out—make your Siesta Key dream a reality today!

5219 Calle De Rio, Sarasota
$3,330,000
4 Beds ⋅ 4 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
This is the renovation you would do for yourself…. If you’ve toured new construction homes recently and thought to yourself, did the architects just give up? Then this home might just be for you… *Elegance. Charm. Attention to detail.* Three phrases we don’t hear enough anymore, but that changes today as we step inside ‘Casa Alegre’ on Featherbed Lane. Located in the heart of Siesta Key Village and positioned at one of the most impressive intersections of waterways the Grand Canal offers, there is no more sought-after location on all of Siesta Key than right here. An 8-minute walk into the Village merges proximity with privacy in the exact way you’ve been imagining. This fully renovated Mediterranean Revival is overflowing with pride of ownership. Featuring major upgrades including a new roof, new seawall, all new hurricane windows and doors, new flooring, new electrical, and more; this is the renovation you would do for yourself, and that translates into true confidence, not just fresh finishes. Inside, the home lives bright and open, in part from its southern facing pool, and even more-so with volumes of natural light pouring in through NINE sets of brand-new sliding glass doors and a layout designed for effortless island living and entertaining. With 4 true bedrooms, 4 baths, plus an incredible bonus room ready for a billiards table or game room, a heated pool and boating lifestyle at your doorstep, this is a rare opportunity to own a home with genuine character, in a location that simply can’t be replicated. Private showings available upon request.

4833 Featherbed Lane, Sarasota
$1,350,000
Harmony Sub SubDv. ⋅ 34242 Zip Code
Primrose path is a quiet street one block long. The property has 250 feet of wide canal front which is extremely rare. It includes a newer extra large cement cap. The pretty setting is next to a picturesque bridge and has another long canal view facing the front of the lot. It is very close to Siesta village. The existing structure could possibly support a second floor addition as the first floor was flooded. The area supports housing over 4 million. The owner is a licensed broker. Value is in the land.

4839 Primrose Path, Sarasota
$1,350,000
4 Beds ⋅ 4 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
Primrose Path is a quiet street only one block long. The property has 250 feet of wide canal front which is extremely rare. It includes a newer extra-large cement cap. The pretty setting is nest to a picturesque bridge and has another long canal view facing the front of the lot. It is very close to Siesta Village. The existing structure could possibly support a second-floor addition as the first floor was flooded. The area supports housing over 4 million. The owner is a licensed broker. Value is in the land.

4839 Primrose Path, Sarasota
$535,000
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Experience coastal living at Sunrise Cove, one of Siesta Key’s most amenity-rich and sought-after waterfront communities. This beautifully updated 2-bedroom, 2-bath residence offers an ideal location directly on Sarasota Bay and just across from the turquoise waters and sandy shoreline of Turtle Beach. Updated within the last four years and offered turn-key furnished, this home features impact-rated windows, new flooring, upgraded lighting, HVAC, and kitchen improvements, all designed with a bright coastal aesthetic. The open concept layout flows from the kitchen to the dining and living areas and out to a private terrace where breathtaking sunrises over the bay greet you each morning. With the recent opening of Midnight Pass, the bay now boasts exceptional water clarity in vibrant blues and greens. Boaters will appreciate the rare ability to dock on property at the expansive new dock and slips currently under construction, with an additional full-service marina conveniently located at the adjacent property. Sunrise Cove offers true resort-style amenities including two heated waterfront pools, a recently updated clubhouse with kitchen, ping-pong and billiards, a fitness center, BBQ and picnic area, two lighted tennis/pickleball courts, kayak storage and launch, covered parking, and a washer and dryer on every floor. A popular bayfront restaurant is just steps away, with more dining, shopping, and nightlife a short distance up the road in Crescent Village. This residence delivers the perfect combination of beach access, boating, and amenity-rich island living—move in this season and enjoy the best of Siesta Key.

8977 Midnight Pass Road Unit 223, Sarasota
$1,175,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Experience elevated coastal living in this beachfront penthouse condo on Siesta Key, where direct Gulf views greet you the moment you walk through the door. Bathed in natural light, this turnkey furnished residence captures breathtaking sunsets and offers an effortless blend of luxury and comfort. The bright kitchen is thoughtfully designed with granite countertops and solid wood cabinetry, perfect for both everyday living and entertaining. The flexible guest bedroom features Murphy beds, maximizing space while maintaining style and functionality. New impact windows enhance peace of mind while framing endless views of the Gulf. Located within the highly sought-after Whispering Sands, a 25-acre resort-style community, residents enjoy more than 800 feet of private Siesta Beach with powdery white sand. Amenities include two swimming pools, two clubhouses, exercise rooms, a picnic area with tiki hut and grills, kayak and canoe storage, a tranquil lagoon, and meticulously landscaped grounds. Just moments from Siesta Village, this penthouse offers the perfect balance of privacy and proximity to world-class dining, shopping, and entertainment. Whether as a full-time residence or a luxury retreat, this exceptional penthouse delivers the ultimate Siesta Beach lifestyle.

19 Whispering Sands Drive Unit 1204, Sarasota
$3,250,000
3 Beds ⋅ 3 Baths ⋅ Sara Sands SubDv. ⋅ 34242 Zip Code
This custom-built home received the “Best Overall” award in the 2021 Manatee and Sarasota County Parade of Homes. Experience the pinnacle of Siesta Key waterfront living in this 2019-built masterpiece by Nutter Custom Construction. Designed with precision and built to last, this solar-powered coastal retreat sits on high elevation and spans over 3,400 living square feet, offering 3 bedrooms, 3 baths, and two versatile flex rooms that redefine modern island living. Every element blends elegance, performance, and peace of mind. You walk into a wide-open floor plan that immediately draws you in. To the left, the primary suite offers total privacy with a spacious bedroom, spa-inspired bathroom featuring double vanities, a soaking tub, glass-enclosed shower with 4 shower heads, and a private outdoor shower with 2 shower heads, connected directly to the master bath a truly open-air sanctuary. To the right, your dedicated office provides focus and functionality and can easily serve as a fourth bedroom, with the flex room ideal for a home office or bonus space. The heart of the home opens to expansive living and dining spaces with a chef’s kitchen showcasing high-end cabinetry, premium flooring, designer lighting, and top-of-the-line Sub-Zero and Wolf appliances. Each guest bedroom includes its own private en-suite bath, offering comfort and privacy for family and visitors alike. A large walk-in pantry and laundry room are conveniently positioned near the kitchen. A whole-home water softening system, an In-wall pest control system with access ports, 2 air conditioning systems to keep the home evenly comfortable during the warmest weather, and 2 tankless water heaters to provide plenty of hot water. An oversized three-car garage for everyday ease. An additional flex room opens to the pool through oversized sliders, perfect for a second office, game room, or guest suite. There are automated window shades in the living room and game room. The home runs entirely on solar power and includes a multi-room sound system that fills the home and outdoor living space with your favorite music. Massive hurricane-rated sliding glass doors wrap the back of the home, creating a seamless flow to your backyard oasis, including landscape lighting and an irrigation system. An Integrated Security System with perimeter cameras provides extra peace of mind. Step out onto the beautiful travertine pool deck, featuring a heated pool and champagne-edged spa, outdoor lounge, and covered dining area with a built-in outdoor chef’s kitchen powered by propane, perfect for entertaining in style, and all with a sunset view. Beyond the pool, enjoy a lush, manicured backyard with direct access to the wide Siesta Key Grand Canal. A dedicated 14,000-pound boat lift allows you to launch your boat with ease, making days on the water effortless. A separate private docking area is available for your friends to arrive by boat or for jet skis. Enjoy kayaking, paddleboarding, and scenic canal rides, or simply relax and take in the sunsets from your extended concrete pad with a built-in concrete firepit, ideal for gatherings by the water. Every detail of this home is custom-crafted, from its hurricane-rated construction and elevated-lot placement to its energy-efficient systems and timeless coastal design. 5058 Windward Ave isn’t just a home, it’s a statement in waterfront living: high elevation, solar-powered, elegant, and built for those who expect the very best on Siesta Key.

5058 Windward Avenue, Sarasota
$1,125,000
4 Beds ⋅ 4 Baths ⋅ Twin Oak Pond SubDv. ⋅ 34242 Zip Code
Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire property has been updated with wood-looking vinyl, interior/exterior paint, custom baseboard and trim, contemporary lighting fixtures, modern fans and fresh marcite in the refinished pool. The studio provides new vinyl windows and a mini-split AC unit for energy efficient climate controlling of this private space. You will love the floor plan of both the main house and studio! The main house provides a great room concept with an abundance of joyful natural light and multiple sets of French doors leading to the pool. Each bedroom receives a private bath with 2 primary suites enjoying idyllic views of the pool and tropical landscape. Simply stated, this estate property is meant for hosting large groups, comfortably. Located inside the charming Canopy Roads of Twin Oak, this beach property is private, serene and inspiring. Live by the beach, but away from the noise. The good life is found here

5244 Winding Way, Sarasota
$690,000
3 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
This beautifully reimagined, 3 bed/2 bath, detached freestanding villa with garage in the GULF FRONT property of Whispering Sands has been thoughtfully updated from top to bottom in 2025, offering 1,327 square feet of sophisticated, light-filled living space – blending modern style with effortless comfort. NEW 2025 villa roof. Elegant finishes include fresh interior paint, crown molding, textured ceilings, recessed lighting throughout, ceramic tile flooring in the main living areas, and newly carpeted bedrooms. At the heart of the home is a NEW open kitchen designed for both style and function, featuring granite countertops, breakfast bar, stainless Whirlpool appliances, abundant soft-close cabinetry, and pantry with convenient pull-out drawers. Recessed and under cabinet lighting complete this inviting space. NEW hurricane impact sliders in the living areas and bedrooms provide total peace of mind. A spacious brick paver patio creates an ideal setting for sunny relaxation, entertaining, or grilling under the stars. Both bathrooms have been tastefully updated with granite countertops, soft-close cabinetry, modern fixtures, lighting, and glassed walk-in showers. NEW full sized washer and dryer. Community enhancements include scheduled exterior pressure washing and villa painting in January 2026, with beautiful new landscaping to follow. FURNITURE minus a small exclusion list is included with the sale of the property.

204 Hourglass Way Unit V9, Sarasota
$3,750,000
4 Beds ⋅ 4 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Nestled within the exclusive gated Siesta Key waterfront enclave of Spice Bay, home to just 14 residences, The Somerset by London Bay Homes defines the pinnacle of coastal contemporary luxury with distinctive West Indies architecture. This two-story, four-bedroom estate harmonizes seamlessly with its lush tropical surroundings, offering serene garden views framed by palms and vibrant flowering landscapes. Just a short stroll from the home, a fully equipped, privately assigned dock along Little Sarasota Bay provides effortless boating access, featuring a 14,000-lb boat lift at the pier’s end. View the immersive 3D Interior Tour One. Spanning more than 5,000 square feet of air-conditioned living space, the estate is designed for both elegance and effortless entertainment. Expansive sliding glass walls open the great room to the pool deck and covered outdoor living area. French oak flooring and silver-toned designer lighting unify the interior, connecting the dining room, gourmet kitchen, study, and master suite with a refined, cohesive flow. A hidden entry room—currently housing a Control 4 home automation system—offers the potential for a future elevator while controlling lighting, music, and security throughout the home. Exquisite millwork enhances the interiors, including beadboard, custom built-ins, and architectural beams along the entry stair wall, great room media feature, and gallery leading to the master suite. Floating beams and polished nickel pendant lighting highlight the kitchen and dining area, while a dramatic pyramid ceiling elevates the master bedroom. The study, with its beamed ceiling and pool deck access, opens via double doors for privacy and elegance. The chef’s kitchen is outfitted with Pompeii white mist quartz countertops, a smoked stiletto tile backsplash, an oversized apron-front breakfast bar, and seamless access to the wine room and butler’s pantry. The dining area flows to the alfresco living space, complete with a fully equipped outdoor kitchen and a dedicated full pool bath. Upstairs, a loft and family room are joined by two guest suites and a fourth bedroom, offering private accommodation for visitors which includes a convenient washer dryer closet. The master suite overlooks the pool and outdoor fireplace and features a private sitting area. Its luxurious bath includes emerald quartz dual vanities, a polished nickel chandelier, a beamed ceiling, and a freestanding soaking tub beneath a picture window. Outdoor living is elevated with a motorized retractable screen, covered lounge and dining area, and a custom Bahama blue linear pool with sun shelf, spa, raised glass-tiled wall with bronze scuppers, and built-in planter. A sun deck, waterfall feature, mosquito misting system, and nearby fireplace create a serene, resort-style experience in complete privacy. The award winning white powdery sands Siesta Key beach, restaurants and fun shopping are a short three miles away. Quick access to downtown Sarasota with entertainment, dining and cultural options. Additional amenities include a three-car air-conditioned garage with motorized storage and bike lifts, a 24kW whole-house Generac generator connected to natural gas, fenced in pet exercise area and irrigation supplied by a private on-site well.

1202 Sharswood Lane, Sarasota
$725,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
LOCATION, LOCATION, LOCATION!!! THIS LOT IS ONLY 2 BLOCKS TO SIESTA KEY BEACH, WITH NO HOA'S! Come see the possibilities of this lot to build your dream home. This location gives you a short walk, or use of the Frog Hop to the village, or a Sunset walk on the beach. This home DID take on water, and is UNINHABITABLE to live in. Both buildings on the property will be locked, and unavailable to go inside.

5531 Calle Del Verano, Sarasota
$5,250,000
3 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
A truly one-of-a-kind beachfront home with spectacular western-facing Gulf views, this is one of only 7 homes on private Tenacity Lane at the north end of Siesta Key. A few steps along your private backyard path lead you to the powdery white sands of Siesta Key Beach. Built with the main living areas above county elevation requirements, the home captures sweeping beach-and-ocean panoramas from nearly every room. The living room features a stone fireplace, soaring ceilings, and a wall of sliding glass doors that frame the Gulf and fill the space with natural light. The kitchen and dining area also afford water views and include stainless steel appliances, a gas cooktop, built-in oven/microwave, and a wet bar—ideal for entertaining. A standout feature is the upper loft overlooking the beach with its own private deck for an even higher vantage point. The spacious primary suite includes a beach-facing alcove—perfect for a private office or reading nook—along with a large bath with dual sinks, a jetted tub, a separate shower, and a private balcony. Two additional bedrooms are generous in size with large windows, en-suite baths, and water views. Outside, the expansive beachfront deck is partially covered and provides scenic space for grilling, stargazing, or simply enjoying the beach view. The ground level houses a two-car garage, abundant storage, and a full bath. The expansive driveway accommodates parking for 12+ vehicles, alongside a large covered outdoor space for relaxing in the shade. Zoned Residential Multi-Family and offered furnished, this private, direct beachfront property is just steps to Siesta Key Village, renowned for it’s nightlife, dining, shopping, and entertainment. The true value of this property is in the land - it's location, direct beach frontage and access. This is an exceptional opportunity to enjoy as-is, renovate, or reimagine entirely. A prime Siesta Key setting with endless potential—a truly rare opportunity to secure a legacy property and create something extraordinary on one of Florida’s most coveted stretches of sand.

216 Tenacity Lane, Sarasota
$800,000
Siesta Key SubDv. ⋅ 34242 Zip Code
An extraordinary opportunity awaits to create your own private waterfront oasis on world-renowned Siesta Key. Located at 7676 Midnight Pass Road, this expansive 0.43-acre cleared and level lot offers the ideal canvas for a custom coastal retreat that embodies tranquility, luxury, and the essence of island living. Positioned along the serene waters of Heron Lagoon, the property features approximately 111 feet of peaceful, protected waterfront—perfect for designing your own dock for kayaking, paddleboarding, or simply enjoying the beautiful views of the lagoon. The setting is quiet, secluded, and immersed in natural beauty, delivering a true sense of sanctuary. All just moments away from the dazzling white sands of Siesta Key Beach, consistently ranked the #1 beach in the United States for its powder-soft quartz sand, vibrant turquoise waters, and breathtaking sunsets. Here, you are close enough to stroll or bike to the shoreline yet tucked away in your own world of serene waterfront living. The lot is cleared, spacious, and ready to build, with utilities already available—offering a seamless start to designing your dream coastal estate without the delays of demolition or site preparation. This is truly a rare chance to craft your own slice of paradise on one of Florida’s most coveted barrier islands. Do not miss the opportunity to transform this exceptional property into the Siesta Key retreat you’ve always imagined.

7676 Midnight Pass Road, Sarasota
$720,000
4 Beds ⋅ 4 Baths ⋅ Siesta Manor SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Build Your Coastal Dream on Siesta Key – Hurricane-Ready Luxury by SeaSafe Homes. This offering includes both the canal-front lot on Avenida Leona in Siesta Key and the construction of the Battery Point Model by SeaSafe Homes. This is a rare opportunity to build a high-performance coastal home in one of Siesta Key’s most desirable neighborhoods. Located just a short stroll from Siesta Village and world-renowned beaches, this canal-front lot is being offered with a full construction package for the Battery Point Model by SeaSafe Homes—a cutting-edge residence built for strength, speed, and style. Engineered to excel in extreme coastal environments, the Battery Point features a fortified 2x10 floor system, 2x6 walls, and a 180 MPH wind rating—far exceeding Florida’s standard building code. Built using advanced off-site construction methods, this home can be completed in 75% less time than traditional builds, minimizing weather exposure and maximizing efficiency. The design blends resilience with refined living: 4 spacious bedrooms, 3.5 baths, and an open-concept elevated floorplan with a chef’s kitchen, large walk-in pantry, and 10-foot island for entertaining. Expansive windows and sliders open to a covered porch that invites seamless indoor-outdoor living. The primary suite offers direct porch access, a spa-style bath, and dual walk-in closets. The lower level entry includes a welcoming foyer with an optional elevator to all floors. Every SeaSafe home is Zero Energy Ready, with high-efficiency sealed systems and superior insulation included as standard—features that often come at a premium elsewhere. Whether you're looking for a full-time residence, seasonal escape, or vacation rental investment, this pre-construction package offers you the chance to create a resilient and thoughtfully designed retreat in one of Siesta Key’s most coveted locations. Plans and pricing subject to change. Renderings and features are conceptual and represent the proposed home.

312 Avenida Leona, Sarasota
$720,000
Siesta Manor SubDv. ⋅ 34242 Zip Code
20% Down Seller Financing Offered. Design Your Legacy on Siesta Key – Premier Waterfront Lot in Siesta Manor Welcome to Lot 17 on Avenida Leona—an extraordinary opportunity to create your own masterpiece in one of Florida’s most coveted coastal enclaves. Nestled along a private, tree-lined lane in Siesta Manor, this canal-front parcel offers the rare combination of deep water access, walkability to Siesta Key Village, and the serenity of a tucked-away residential setting. Spanning .183 acres, this build-ready lot offers 64 feet of seawall-lined frontage on a peaceful boating canal, granting direct access to the shimmering Intracoastal Waterway and beyond. Whether your dream home includes a sleek infinity-edge pool, a private dock for sunset cruises, or a lush tropical garden oasis, this lot provides the perfect canvas for refined waterfront living. Step outside and find yourself just moments from the soft quartz sands of world-famous Siesta Beach. Stroll to the vibrant Village for gourmet dining, boutique shopping, and a lively arts scene—all while retreating each evening to the tranquil rhythm of the water and the gentle call of seabirds overhead. As Sarasota continues to rise as one of the nation’s premier luxury destinations, Siesta Key remains its crown jewel—where timeless beauty, natural splendor, and elevated lifestyle converge. Whether you’re envisioning a coastal escape or a showstopping modern estate, Lot 17 is your blank slate in paradise. This is more than just land—it’s your legacy in the making.

Avenida Leona, Sarasota
$963,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
REMODELED GULF FRONT CONDO. NEW HURRICAN WINDOWS ON GULFRONT ROOM ALSO EQUIPPED WITH HURRICANE SHUTTERS ON OTHER WINDOWS. NEW TEAK WOOD CEILING IN BONUS ROOM OVERLOOKING THE PRISTINE QUARTZ BEACH. STYLISH GRANITE AND ALL WOOD SHAKER CABINETS. NEW KITCHENAIDE STAINLESS APPLIANCES. ALL NEW MINKAIRE CEILING FANS, BEACHY LAMINATE FLOORS, NEW SHOWER TILING, OVERSIZED VANITIES AND SOLID WOOD BARN DOORS. ONE OF ONLY 12 TRUE BEACHFRONT UNITS IN PEPPERTREE. COMPLEX HAS GATED BEACH, BBQ GRILLS, CLUBHOUSE, FITNESS AND TENNIS COURTS. WAKE UP AND TAKE A STROLL ON THE PRESTINE QUARTS BEACH, WHAT A WAY TO START YOUR DAY FINSIH WITH A SPECTULAR SUNSET.

1013 W Peppertree Drive Unit 115, Sarasota
$640,000
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
Price Reduction - Motivated to Sell! This beautifully updated condo at Harbor Towers Yacht & Racquet Club presents an exceptional opportunity for both luxurious coastal living and strong investment potential. Thoughtfully renovated with attention to every detail, recent upgrades include a NEW HVAC system (Nov. 2025), NEW electrical panel (Nov. 2025), luxury vinyl flooring, and a remodeled kitchen featuring solid wood cabinetry and granite countertops. Just in time for the upcoming rental season, the condo is also being offered with new furniture and small appliances, enhancing comfort, style, and rental appeal. Located in the heart of tropical Siesta Key, this residence enjoys breathtaking water views along one of the widest stretches of Intracoastal frontage on the island—an increasingly rare and valuable feature. The resort-style community offers an impressive array of amenities, including a state-of-the-art fitness center, two heated pools, and three illuminated Har-Tru tennis courts, perfectly suited for both relaxation and recreation. Additional highlights include high-speed Wi-Fi, gas grilling areas, a boat basin, and the tranquil Island Gazebo, ideal for unwinding or watching dolphins pass by. The location is equally exceptional. Just minutes from Siesta Key Village, residents enjoy easy access to boutique shopping, dining, and entertainment, along with complimentary use of the Siesta Key Open Air Trolley for effortless island exploration. World-famous Siesta Key beaches are only moments away, and Sarasota’s vibrant arts, dining, and cultural attractions are a short drive from home. Whether you’re looking for a primary residence, a vacation getaway, or a highly desirable investment property, this move-in-ready condo delivers an unmatched lifestyle in one of the world’s most sought-after beach destinations. Schedule your private showing today.

5855 Midnight Pass Road Unit 311, Sarasota
$3,500,000
4 Beds ⋅ 5 Baths ⋅ Point Crisp SubDv. ⋅ 34242 Zip Code
Welcome to 1364 Point Crisp, a breathtaking waterfront home on one of the most private and interesting streets on Siesta Key. With only seven homes on this secluded section of road, you’ll enjoy peace, quiet, and incredible views of Little Sarasota Bay and the Intracoastal Waterway. Watch sailboats glide by or fishermen return from a great day out in the Gulf. This home is a boater’s dream, featuring a 16,000# boat lift and a 10,000# personal watercraft lift not to mention a separate day dock and kayak Launch in the back yard. The heated saltwater pool was custom built and features a spacious deck, and plenty of room to entertain family and friends. Relax on one of the two large second-floor balconies with an outdoor grill area and roll-down screens—perfect for enjoying a glass of wine while watching the sunset. Other features include: a 100KW Kohler commercial backup generator powered by natural gas, Impact-rated doors and windows, well water for irrigation and city water access at multiple points, including the dock. Six climate-controlled garage spaces plus tons of extra storage on the first level, with easy access to the backyard and pool. Inside, with an elevator serving all levels of the home, you’ll find 4 spacious bedrooms, 5 full bathrooms, and a modern kitchen with a Sub-Zero refrigerator, Thermador induction cooktop, and GE Monogram appliances. The wet bar includes a beverage fridge and extra storage—perfect for entertaining. This home has been meticulously maintained and offers countless hidden conveniences that make life easier. Don’t miss your chance to own this incredible waterfront retreat!

1364 Point Crisp Road, Sarasota
$555,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Peppertree is a Gulf-to-Bay community of resort style living situated on 16 acres of beautifully landscaped tropical grounds, providing private access to Crescent Beach and within easy walking distance of Siesta Key Beach and Siesta Village. Amenities include two clubhouses, two heated pools, tennis courts, a recently renovated fitness center with locker and sauna, and a fishing pier on the Intracoastal Waterway, BBQ grills, on-site management, rental program and security. Original owners! This vintage unit is located on the gulf side of the property and is ready for a remodel, allowing you to create your dream coastal retreat. Spacious supersized laundry/utility inside the unit. Secure elevators and under building parking is provided. New hurricane windows to be installed by the association at no cost to the owners. Shopping, golfing, restaurants and the Arts are all just minutes away. This is a rare opportunity to own in one of Siesta Key's most desirable communities. Don't miss out - schedule your private showing today!

1055 W Peppertree Drive Unit 505AA, Sarasota
$1,000,000
3 Beds ⋅ 3 Baths ⋅ Sara Sands SubDv. ⋅ 34242 Zip Code
An exceptional opportunity on iconic Higel Avenue in Sarasota, where value is firmly rooted in land, location, and waterfront lifestyle. Situated on over 15,000 square feet, nearly half an acre, this property offers 92 feet of canal frontage and endless potential to renovate, expand, or build your dream coastal retreat.The existing residence features 3 bedrooms, 2 full bathrooms, and 1 half bath, providing immediate functionality while allowing flexibility for future plans. Whether envisioned as a personal residence, investment, or redevelopment opportunity, the setting alone is truly compelling.The location is unmatched. Just 0.6 miles to the vibrant Siesta Village, enjoy easy access to boutique shopping, acclaimed dining, and local nightlife. Beach lovers will appreciate being only 0.7 miles to the nearest beach access, with the main entrance to world-renowned Siesta Beach just over a mile away, celebrated for its powdery white sands and crystal-clear waters.This is more than a property. It is a rare chance to secure a premier canal-front parcel in one of Sarasota’s most desirable coastal corridors, offering a lifestyle defined by proximity to the water, the beach, and everything that makes Siesta Key extraordinary.

5036 Higel Avenue, Sarasota
$1,000,000
Sara Sands SubDv. ⋅ 34242 Zip Code
An exceptional opportunity on iconic Higel Avenue in Sarasota, where value is firmly rooted in land, location, and waterfront lifestyle. Situated on over 15,000 square feet, nearly half an acre, this property offers 92 feet of canal frontage and endless potential to renovate, expand, or build your dream coastal retreat.The existing residence features 3 bedrooms, 2 full bathrooms, and 1 half bath, providing immediate functionality while allowing flexibility for future plans. Whether envisioned as a personal residence, investment, or redevelopment opportunity, the setting alone is truly compelling.The location is unmatched. Just 0.6 miles to the vibrant Siesta Village, enjoy easy access to boutique shopping, acclaimed dining, and local nightlife. Beach lovers will appreciate being only 0.7 miles to the nearest beach access, with the main entrance to world-renowned Siesta Beach just over a mile away, celebrated for its powdery white sands and crystal-clear waters.This is more than a property. It is a rare chance to secure a premier canal-front parcel in one of Sarasota’s most desirable coastal corridors, offering a lifestyle defined by proximity to the water, the beach, and everything that makes Siesta Key extraordinary.

5036 Higel Avenue, Sarasota
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Knock, knock your slice of paradise is calling! There’s no place like this home or home away from home! A gorgeous view in an exquisitely updated condo on the world’s finest beach! What more could you ask for?!! HURRICANE WINDOWS, Quartz countertops EVERYWHERE (even in the laundry room!), wine refrigerator, Kitchen Aid appliances, new cabinetry (including in the bathrooms), closet built-ins, luxury vinyl plank flooring, tasteful, coastal furniture, electronic remote control Hunter Douglas shades on windows, ample storage, full size utility room, enclosed balcony professionally done so it truly feels like part of the home. Being sold furnished with everything you need to get started living the good life! The Gulf & Bay community is packed with amenities and spacious grounds, located mid-key with easy access to the north or south bridge, with a guarded gate and on-site property management, you will not be disappointed! 4 Tennis (3 Plexi cushion, 1 clay), 6 pickleball courts, and 2 racquetball courts, shuffleboard, a fitness room and clubhouse with a library, computer and meeting/event room and card room. The common area and multiple pools are lushly landscaped and manicured, giving you that true resort feel. The parking lot is pavered and carports, with deeded parking spaces, are included with units as well as ample guest spaces. There is also a carwash area and there are electric vehicle charging stations. Building E has the advantage of being closer to the water and therefore a more up-close view of the Gulf. Click your heels together and power up that hot air balloon (or whatever mode of transport you prefer) and hurry over to follow your heart and mind and gather the courage to grab your slice of paradise before it’s gone! This is not a dream, it’s a dream come true!

5750 Midnight Pass Road Unit 508 E, Sarasota
$700,000
Siesta Isles SubDv. ⋅ 34242 Zip Code
Nestled on picturesque Shadow Lawn Drive, this 12,800-square-foot lot offers an exceptional canvas for your custom home. Framed by mature live oaks on the front left and back right corners, the property blends natural beauty with an enviable location. Enjoy the best of Siesta Key living—just an 8-minute stroll to the powdery sands of world-famous Siesta Beach and just over a mile to the dining and shopping of Siesta Village. Despite its proximity to these sought-after amenities, the property feels peaceful and secluded, tucked away on a quiet street removed from the island’s main thoroughfares. With nearly 100 feet of street frontage and a depth of 120 feet, the lot offers a generous and flexible building footprint. Whether you envision a sleek, modern coastal retreat or a charming, classic island cottage, this is a rare opportunity to create your ideal Siesta Key home in one of its most desirable neighborhoods.

5587 Shadow Lawn Drive, Sarasota
$635,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
You have the best of both worlds with this unit, a View to the East overlooking over the Intracoastal waterway and the Private Beach to the West. As you walk into the dining/living room you will become enchanted with the mesmerizing view. Whether its a daytime view of the intracoastal boats of many sizes and shapes-yachts-sailboats, and dont forget its birds, sea faring animals; or when nighttime falls you will see the twinkle of the city lights under your watchful eye. Going Turnkey Furnished! Not much to do in this unit; impact windows on lanai, bathrooms and kitchen updated. Where else can you get a supersized utility room, parking under the building two heated pools, tennis and pickle ball courts, fishing pier, clubhouses and of course beach access. Management on site.

1255 E Peppertree Drive Unit 506, Sarasota
$1,835,000
3 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
INCREDIBLE FULL Sunset & Gulf Views!....INCREDIBLE "Everything" UPDATES & FINISHES!....INCREDIBLE Boutique Beachside Community!....Rarely Available, You will be WOWED! by this Stunning (3) Bedroom TOP FLOOR residence with GARAGE PARKING in Sought After Casarina---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 Full Gulf and Beach Views, to be further enjoyed with Morning Coffee and Evening Cocktails on the Generously Sized Lanai*****Bright & Spacious Open Floorplan with Well-Appointed Interiors were COMPLETELY and THROUGHLY renovated, including: ALL Plumbing & Fixtures; Multi-Speed HVAC along with Ductwork; Electrical; Ceilings, Custom Millwork; Polished Porcelain Tile Throughout, Hurricane Windows/Doors; and Kitchen & Baths: Layout, Solid-Wood Cabinetry; Custom Tile Backsplashes; Countertops and CAFE Appliances*****Deeded Beach Access, perfect 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---- Ideal as Second Home/Vacation, Investment or Year-Round Residence. Island Living @ It's Finest......

5880 Midnight Pass Road Unit 910, Sarasota