Siesta Key Homes with Private Pool type

Siesta Key Homes with Private Pool type

Welcome to Siesta Key, Florida, a stunning barrier island nestled along the Gulf Coast, renowned for its powdery white sands and vibrant, laid-back atmosphere. Located in Sarasota County, Siesta Key offers an idyllic blend of natural beauty and charming coastal living. With its picturesque beaches, crystal-clear waters, and lush tropical landscapes, this enchanting locale is a haven for those seeking both relaxation and adventure.

Siesta Key is not just a beach lover’s paradise; it also boasts a rich cultural scene with art galleries, boutique shops, and a variety of dining options that cater to every palate. Whether you’re indulging in fresh seafood at a waterfront restaurant or exploring the local art scene, Siesta Key has something for everyone.

When it comes to real estate, Siesta Key offers a remarkable selection of homes, particularly those with private pools—an essential feature for enjoying the warm Florida sun. Imagine lounging by your very own pool, surrounded by lush landscaping, while savoring a refreshing drink after a day at the beach. These homes provide the perfect setting for entertaining friends and family or simply unwinding in your personal oasis.

Whether you’re looking for a cozy beach cottage, a luxurious waterfront estate, or a modern family home, Siesta Key's real estate market has it all. Embrace the lifestyle you’ve always dreamed of in this charming coastal community, where every day feels like a vacation. Discover your perfect home with a private pool in Siesta Key and experience the ultimate Florida living!

Newest Siesta Key Homes with Private Pool type

$2,250,000
3 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
LOCATION, WATERFRONT, BOATING AND INCOME POTENTIAL come together at 4937 Oxford Drive, an exceptionally spacious, one-story pool home with coveted frontage on Siesta Key's Grand Canal. Offering an impressive 2,539 square feet of living space with three bedrooms plus an office, this home stands out for its generous proportions, wide-open living areas and rare single-level floor plan. Even more noteworthy, the home has experienced NO WATER INTRUSION, an important distinction for island living. A previous remodel raised the ceilings, creating a wonderful sense of volume, light and openness throughout the main living spaces. Step outside and the reason for owning on Siesta Key becomes even more compelling. The screened lanai surrounds a heated saltwater pool, while beyond it lies the Grand Canal — one of the island's defining waterways and a tremendous advantage for those who want to embrace the Siesta Key boating lifestyle. Although the former dock was lost years ago, the existing pilings remain, presenting a potential opportunity to reestablish a dock and create your own waterfront setup, subject to applicable permitting and approvals. Beyond its appeal as a full-time residence or island retreat, this property has been a SUPERB INCOME PRODUCER, offering outstanding potential for an owner seeking both lifestyle and investment opportunity. And the location is hard to beat — close to Siesta Key Village, world-famous Siesta Beach, restaurants, shopping and all the energy of island life, with convenient access to the mainland. Large, one-story homes offering this much living space, a private pool, Grand Canal frontage, boating potential, strong income history and NO WATER INTRUSION are difficult to find. Whether you envision a personal waterfront retreat, an income-producing investment or the best of both, 4937 Oxford Drive delivers a rare combination of space, location and Siesta Key lifestyle.

4937 Oxford Drive, Siesta Key
$1,499,000
3 Beds ⋅ 2 Baths ⋅ Waterside East SubDv. ⋅ 34242 Zip Code
Exceptional Siesta Key Retreat on Over Half an Acre with Brand-New Heated Pool. This beautifully transformed 3-bedroom, 2-bathroom residence sits on an impressive 0.50-acre (21,977 SF) parcel, offering a rare blend of space, privacy, high-end craftsmanship, and indoor-outdoor living on Siesta Key. Inside, wide-plank flooring, designer lighting, and warm natural textures anchor a bright, open layout. The centerpiece is a chef’s kitchen equipped with premium Café series appliances, custom cabinetry, an oversized waterfall island with seating, expansive counter space, and elegant brass accents. The kitchen flows seamlessly into the main dining and living areas, creating an ideal setting for entertaining. A separate family room with a wood-burning fireplace offers a second gathering space, framed by large glass doors that open to the outdoor oasis. The primary suite features direct access to the lanai and a redesigned spa-inspired bathroom with dual vanities, an oversized glass-enclosed shower, warm wood detailing, and custom tilework. Two additional bedrooms and a refined guest bath provide high-end accommodations for visitors. Outside, the brand-new heated pool and expansive screened lanai create a resort-style environment for swimming and alfresco dining. Beyond the lanai, mature trees and a sprawling yard provide a level of privacy and green space rarely found with island living. Located minutes from world-famous beaches, dining, shopping, and boating in Sarasota. Schedule your private showing today.

670 Venice Lane, Sarasota
$2,995,000
3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
For the buyer who believes the best of Siesta Key is experienced by boat, 5178 Oakmont Place delivers an exceptional combination of deep-water canal frontage, estate-sized privacy, refined island living, and effortless access to Sarasota Bay. Set on more than half an acre along Siesta Key’s coveted Grand Canal, this tastefully updated custom residence pairs Caribbean-inspired architecture with 93 feet of waterfront, a private dock, and impressive 30,000-lb boat lift—creating a true luxury retreat for boating enthusiasts just minutes from the bay. A winding paver driveway introduces the private tropical setting, leading to a gracious residence by award-winning builder Lee Wetherington. Inside, high ceilings, substantial crown molding, elegant archways, tray ceilings, recessed lighting, and expansive windows create an airy sense of scale, while warm bamboo flooring brings natural sophistication throughout the primary living spaces. Designed for relaxed island living and entertaining, the open great room is anchored by a striking coral stone gas fireplace and framed by French doors connecting the interior to the expansive covered veranda. The updated kitchen features crisp white cabinetry, granite countertops, stainless steel appliances, breakfast-bar seating, generous storage, and an adjacent service bar, complemented by a separate dining area for effortless entertaining. The spacious primary suite overlooks the tropical grounds, pool, and waterway and features a tray ceiling, two walk-in closets, dual vanities, large shower, and jetted soaking tub. A desirable split-bedroom floor plan provides two additional bedroom suites, while a large private office offers flexibility for working from home, a media room, or additional lounge space. Outdoor living is a defining feature of this Siesta Key waterfront home. The wide covered veranda provides generous spaces for dining and lounging while overlooking the private swimming pool and lush tropical landscape. Beyond the pool, a pathway leads directly to the Grand Canal and an outstanding boating setup featuring approximately 93 feet of deep-water frontage, a large dock, and 30,000-lb boat lift. Cruise to Sarasota Bay, waterfront dining, or Gulf waters before returning home to enjoy sunset along the canal. Built with quality and longevity in mind, the residence was constructed above base flood elevation and includes hurricane shutters, UV window film, foil roof insulation, floored attic storage, central vacuum, and construction to Miami-Dade standards. An oversized three-car garage offers excellent space for vehicles, bikes, kayaks, paddleboards, fishing equipment, and additional storage. Despite its private, estate-like setting, the home is ideally positioned near Siesta Village, world-famous Siesta Key beaches, boating, dining, and island attractions, with downtown Sarasota approximately 15 minutes away by car. For the luxury buyer seeking a Siesta Key waterfront pool home with deep-water boating access, substantial boat lift, oversized private lot, and proximity to Sarasota Bay, 5178 Oakmont Place offers an extraordinary opportunity to embrace the coastal Florida lifestyle

5178 Oakmont Place, Sarasota
$669,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Discover effortless Siesta Key living in this beautifully updated and fully furnished 2-bedroom, 2-bath condo in the highly desirable Peppertree Bay community. Located on the Gulf side and just steps from the tennis and pickleball courts, heated pool, and private beach access, this second-floor residence offers a peaceful setting with scenic pond views. The interior has been thoughtfully updated with a renovated kitchen and bathrooms, crown molding, fresh paint, new impact windows on lanai and new flooring throughout. The spacious primary suite easily accommodates a king-size bed and features a generous walk-in closet. Additional conveniences include a full-size washer and dryer, tankless water heater, dedicated parking space, and a private storage unit located just outside the front door. Offered fully furnished and truly move-in ready, this condo makes it easy to begin enjoying the Siesta Key lifestyle from day one. Peppertree Bay offers an exceptional Gulf-to-Bay lifestyle with private beach access, a fishing pier, tennis and pickleball courts, two heated pools, two clubhouses, BBQ areas, beach chairs, car wash stations, on-site management, and a rental program. The fitness center and clubhouses are currently being renovated, adding even more to this amenity-rich community. This beautifully maintained residence is an excellent opportunity for a full-time home, seasonal retreat, or Siesta Key getaway. Just bring your suitcase and start enjoying island life!

1141 W Peppertree Drive Unit 1141, Sarasota
$4,190,000
5 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Currently under renovation. Welcome to an exceptional newly updated residence on he highly coveted Bay Island neighborhood on north Siesta Key, where timeless coastal architecture and modern luxury come together in one of Siesta Key’s most desirable locations. Situated on an expansive 0.48-acre homesite, this beautifully designed home offers 4,536 square feet of refined living space with a total of 5 bedrooms, 5 full bathrooms, and 1 half bath. Thoughtfully enhanced with new finishes, designer upgrades, and premium appliances throughout, the home also enjoys glimpses of the ocean water that complement its tranquil coastal setting. A private gated driveway leads to a detached 4-car garage, and guest suite with 2 bedrooms and 2 bathrooms, providing both privacy and convenience. At the center of the residence is a stunning chef’s kitchen designed for both everyday living and entertaining, complete with premium Sub-Zero refrigeration, professional-grade gas appliances, custom cabinetry, elegant stone surfaces, and a spacious center island. The adjoining great room and dining area seamlessly connect to the outdoor living spaces, while the luxurious primary suite provides a private retreat with a spa-inspired bathroom, generous walk-in closets, and peaceful views of the surrounding tropical landscape. Step outside to your own private coastal oasis, where a screened pool and expansive pool deck create the perfect setting for relaxation and entertaining year-round. Beautifully landscaped grounds and thoughtfully designed outdoor living areas enhance the home's resort-style atmosphere. Located just moments from Siesta Key’s world-renowned beaches, waterfront dining, boutique shopping, and Sarasota’s vibrant cultural amenities, this exceptional residence offers an unparalleled blend of privacy, sophistication, and convenience. A rare opportunity to own a luxury home on Norsota Way, where exceptional craftsmanship and the coveted island lifestyle come together. Photos and renderings may include virtual staging and virtual enhancements intended to illustrate the property's anticipated completion and design.

604 Norsota Way, Sarasota
$689,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code
Virtually Staged. Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale. Welcome to Beach Way, where island living begins just steps from world-famous Siesta Key Beach! Perfectly positioned directly across from the powdery white quartz sands and turquoise Gulf waters, this spacious 2-bedroom, 2-bath condominium offers an incredible opportunity to enjoy one of Florida's most sought-after coastal lifestyles. Inside, you'll find a traditional floor plan with defined living and dining spaces, creating a comfortable layout for everyday living or seasonal enjoyment. The kitchen features quartz countertops and ample cabinet space, while tile flooring throughout offers easy maintenance and timeless appeal. The screened lanai overlooks the peaceful community pool, creating the perfect place to relax after a day at the beach. The condo also includes assigned covered parking conveniently located directly in front of the building, elevator access, and private storage. Beach Way is a beautifully maintained community centered around a gorgeous pool, lush tropical landscaping, and ample guest parking. Owners enjoy the flexibility of one-month minimum rentals, up to 12 times per year, making this an excellent option as a primary residence, vacation retreat, or investment property. Ideally located just a short stroll from Siesta Key Village's restaurants, boutiques, and entertainment, this condo offers the best of island living with easy access to downtown Sarasota's dining, arts, and cultural attractions. Whether you're looking for a full-time residence, a winter escape, or an income-producing beach property, this Beach Way condo is ready for you to make it your own!

5600 Beach Way Drive Unit 111, Sarasota
$8,190,000
5 Beds ⋅ 5 Baths ⋅ Elliot M A Property Siesta Key SubDv. ⋅ 34242 Zip Code
A double waterfront, rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with 5 bedrooms, 4 full bathrooms, and 1 half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.

4034 Roberts Point Road, Sarasota
$4,150,000
4 Beds ⋅ 6 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Completed in 2025, this exceptional residence offers a rare opportunity to step into a brand-new partially furnished home without the wait. As opportunities to purchase newly built homes on Siesta Key become increasingly limited, this home delivers the quality, craftsmanship, and peace of mind of new construction in one of the island's most desirable neighborhoods, just moments from Siesta Beach. Spanning more than 5,200 sq ft, the home has been thoughtfully designed with a floor plan that feels as good as it looks. Natural light fills the interiors through expansive PGT impact-rated windows and sliding glass doors, while soaring cathedral and coffered ceilings, wide-plank wood flooring, and clean architectural detailing create a timeless backdrop throughout. The spaces flow naturally from one to the next, striking the right balance between openness and definition. At the center of the home, the kitchen anchors the main living spaces. An oversized quartz island, custom cabinetry, Sub-Zero refrigeration, a Wolf gas range, and generous prep space combine beauty with everyday practicality. Overlooking the great room and dining area, it's where family naturally comes together, while a beautifully appointed wet bar adds another gathering place when entertaining friends. Like any great Florida home, the living spaces don't stop at the back door. Walls of sliding glass open to a covered lanai with a wood-paneled ceiling, leading to a heated pool and spa surrounded by lush tropical landscaping. An outdoor kitchen, pool bath, and outdoor shower complete a backyard designed to be enjoyed year-round, whether hosting family and friends or simply enjoying the privacy of your own home. The thoughtful layout continues with a privately positioned primary suite on the first floor, offering cathedral ceilings, dual walk-in closets, and a beautifully finished bath with a freestanding soaking tub, oversized walk-in shower, and dual vanities. A dedicated office, mudroom, and laundry room complete the main level. Upstairs, three additional en-suite bedrooms, each with walk-in closets and private baths, are joined by a den overlooking the pool, a spacious bonus room with its own Romeo and Juliet balcony, and a second laundry room, providing flexibility as your needs evolve. Built with concrete block construction, a standing seam metal roof, and impact-rated windows and doors throughout, the home reflects the lasting quality buyers expect from a newly completed residence. A split three-car garage and generous paver driveway reinforce the home's thoughtful design and everyday functionality. The location is every bit as compelling as the home itself. Just moments from Siesta Key Beach, you'll have one of the country's most celebrated stretches of coastline practically at your doorstep, while Siesta Village's restaurants, boutiques, and cafés are just minutes away. Downtown Sarasota is an easy drive across the bridge, offering exceptional dining, waterfront parks, galleries, marinas, and the performing arts. It's a location that strikes a rare balance between the relaxed pace of island living and the conveniences of the city. For buyers considering building on Siesta Key, this presents an increasingly rare opportunity. Instead of spending years acquiring land, designing, permitting, and building, you can enjoy a brand-new home from day one, with the home being offered furnished. Beautifully executed and ready now, this is a home built for the next chapter.

656 Tropical Circle, Sarasota
$3,690,000
4 Beds ⋅ 5 Baths ⋅ Tortoise Estates SubDv. ⋅ 34242 Zip Code
With gulf sunset views, and 3-minute walkable private beach access, this New Construction Modern Beach House on Siesta Key mixes a sought-after location with modern luxury. Experience the best of coastal living in this brand-new 4 bed, 4.5 bath home with walking access to Turtle Beach. With 3,676 SF of thoughtfully designed space, this home offers ocean views throughout, multiple outdoor patios and terraces, rooftop deck, and seamless indoor-outdoor flow. Feel the sea breeze in the spacious backyard, including a pool, hot tub, and outdoor kitchen. Enjoy light-toned engineered hardwood floors, a chef’s kitchen with top-tier appliances, and spacious en-suite bedrooms, including a stunning primary suite with a private terrace and spa-like bath. Additional features include a 3-car garage, and 6 covered carport spaces for recreational utility vehicles such as, jet skis, golf carts, or a boat, with easy gate access. Enjoy an elevator included layout, and high-end finishes throughout—all just minutes from Siesta Village’s shops and dining. This newly built residence offers peace of mind with the latest in building codes, energy efficiency, and storm protection. Modern insulation, impact-rated windows and doors, and up-to-date mechanical systems translate into lower utility bills, reduced maintenance, and enhanced safety. You’ll also benefit from turnkey readiness—no need for costly renovations or updates. Whether for full-time living or a coastal getaway, this is Siesta Key luxury at its finest.

8800 Midnight Pass Road, Sarasota
$689,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code
Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale. Experience the best of Siesta Key living in this beautifully renovated first-floor condominium at Beach Way. Located directly across from the world-famous Siesta Key Beach and just a short stroll to Siesta Key Village, this 2-bedroom, 2-bath residence offers the perfect combination of luxury, convenience, and investment potential. Inside, you'll find a thoughtfully updated interior featuring elegant quartz countertops, brand-new stainless steel appliances, durable Cali luxury vinyl plank flooring throughout, and a bright, open floor plan that flows seamlessly into the enclosed lanai. The lanai overlooks the tropical landscaping with a partial view of the community pool, creating the perfect place to relax after a day at the beach. Built for peace of mind, the unit features PGT WinGuard impact-resistant windows (Series 710) and PGT 700 Series impact-resistant sliding glass doors. Convenience continues outside with assigned covered parking located directly in front of the unit, along with ample guest parking for family and friends. Beach Way's desirable monthly rental policy makes this property an excellent option for a primary residence, vacation home, seasonal retreat, or income-producing investment. Enjoy resort-style coastal living just steps from the white quartz sand of world-famous Siesta Key Beach, with the Siesta Key Trolley stop conveniently located right in front of the community for effortless access to Siesta Key Village, shopping, dining, entertainment, and everything the island has to offer.

5600 Beach Way Drive Unit 109, Sarasota
$1,295,000
3 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Island living begins here. Thoughtfully updated and meticulously maintained, this exceptional 2,216-square-foot, three-bedroom-plus-studio, two-bathroom residence seamlessly blends modern comforts with timeless coastal appeal in the heart of Siesta Key. From the moment you step through the front door, you're welcomed by a captivating view of the sparkling heated screened pool, setting the tone for a home designed to embrace effortless indoor-outdoor living. A desirable split-bedroom floor plan offers privacy and functionality, while porcelain tile flooring and impact-resistant windows and sliding glass doors enhance both comfort and peace of mind. The beautifully appointed kitchen features Cambria quartz countertops, a farmhouse sink, a gas cooktop, and a spacious island with additional storage, flowing seamlessly into the home's inviting living spaces. A charming shiplap-accented living room overlooks the tropical backyard, creating a warm and welcoming setting for everyday living and entertaining. Privately tucked away, the primary suite offers vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bath with a classic cast-iron clawfoot soaking tub. Step outside to your private island retreat, where the heated screened pool is surrounded by Shell-Lock pool deck and coping, an outdoor shower, landscape lighting, a mature oak tree, Christmas palm, and multiple Areca palms, creating a tranquil setting complete with a hammock for relaxing in the coastal breeze. Adding to the home's versatility, a private studio with its own exterior entrance offers endless possibilities as a home office, creative studio, fitness room, guest suite, or additional sleeping quarters. Additional highlights include a tankless water heater, a high-efficiency HVAC system with infrared filtration, recessed LED lighting throughout, and exceptional attention to detail. Perfectly positioned in the heart of Siesta Key, this remarkable home offers convenient access to world-renowned Siesta Beach, Siesta Village, and downtown Sarasota.

5125 Sandy Beach Avenue, Sarasota
$11,900,000
5 Beds ⋅ 6 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. The lot is also available as vacant land (MLS #A4682294) ($6.7M). Introducing the Miller Floorplan designed by award winning Konstant Architecture (plans complete and available), a to be built waterfront estate set on one of the most extraordinary parcels on the north end of Siesta Key, one of only 10 properties with water access on the east and west. This award-winning luxury custom build plan is the example of architectural excellence at the highest level. Positioned on over three quarters of an acre with 175 feet of pristine water frontage, this rare offering captures sweeping panoramic views from Big Pass to Bayou Louise. With unobstructed access to Sarasota Bay and the Gulf, boating enthusiasts can enjoy effortless days of fishing, cruising, or island hopping directly from their backyard. This is coastal living without compromise. Designed for both elevated beauty and resilience, the Miller Floorplan features approximately 4,325 square feet of conditioned living space with a raised main living level, private elevator access, and a multi-bay garage with dedicated boat storage below. The thoughtfully designed layout includes five bedrooms, five full bathrooms, and a powder room. The primary suite is privately positioned offering a spa-inspired bath with separate water closet, expansive closet space, and seamless connection to outdoor living. The heart of the home is an open-concept living and dining space anchored by a designer kitchen with pantry and butler’s area, all oriented toward breathtaking water views. Expansive porches, screened outdoor living areas, and a resort-style pool with integrated spa and swim-off areas create a true waterfront retreat. A standing seam metal roof and sophisticated coastal architectural detailing reflect timeless style while complementing the surrounding natural beauty. Located on the coveted north end of Siesta Key, this estate offers both privacy and convenience. The beach, boating, waterfront dining, and Sarasota’s vibrant cultural and entertainment scene are moments away. Large parcels of this caliber with 175 feet of frontage and water access on the east and west side of the property, are rarely available, making this an exceptional opportunity to secure a refined blend of modern luxury, prime location, and long-term value. Where coastal beauty, architectural sophistication, and thoughtful design converge, this residence delivers an unparalleled Siesta Key lifestyle.

3550 Bayou Louise Lane, Sarasota
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