luxury houses with pool for sale Sarasota, United States

One or more photo(s) has been virtually staged. 3 HOMES for the Price of ONE... A Rare Opportunity with unmatched value to Own Three Distinct Residences on One Exceptional Property. This 5+ acre homesite has NO HOA, NO CDD's and NO DEED RESTRICTIONS providing you the freedom to tailor the property to your personality. This is a true MULTI-GENERATIONAL and/or INCOME PRODUCING OPPORTUNITY! Two separate 3BR/2BA Homes + an additional 2BR/2BA Apartment. Each of the homes enjoys its own private entrance, separate driveway and its own garage ~ allowing households to live side by side while maintaining independence. This property is positioned in the most dynamic growth corridor of Sarasota County! Just minutes to the newest LAKEWOOD RANCH WATERSIDE ~ where premier shopping, exceptional dining and modern conveniences continue to flourish! The Workshop features a Full Bath and Laundry Room. In addition, there is another Barn which could accommodate 4+ Cars. Whether accommodating extended family, long-term guests or providing a private residence for caregivers, the thoughtful layout offers exceptional versatility. At the heart of the property, a beautiful SOLAR HEATED POOL and expansive screened lanai create an inviting backdrop for a Florida indoor/outdoor lifestyle. This outdoor retreat is positioned so both residences could enjoy easy access, making it a natural gathering place for family and guests alike. A dedicated pool bath adds convenience for swimmers and guests, keeping the indoor living areas pristine while enhancing seamless flow between indoor comfort and outdoor enjoyment. Expanding the living possibilities, perhaps you might want to consider using part or all of this property as an Airbnb or VRBO rental. The second-level apartment offers privacy with a light and airy vibe featuring an open plan and full kitchen. The unique adjoining sunroom spanning the length of the unit would be ideal for a yoga studio, game room or added entertainment space. Unlock the potential of this versatile apartment as a guest retreat, income-producing rental, inspiring studio or private office suite. The large detached pole barn adds tremendous utility, providing ample space for farm animals, boats, RVs, equipment, hobbies or workshop use, ideal for those who need room to store, build or play. Buy with confidence knowing this home has a WHOLE HOUSE GENERATOR, updated plumbing with no cast iron or copper piping. New plumbing replaced with PVC and the copper potable water pipes have been replaced with CPVC. The 4Point Inspection and Wind Mit has been completed. Homeowner's Insurance only $6700 per year! BRING your RVS, CAR COLLECTIONS & BUSINESS EQUIPMENT! There is plenty of room for a Pond, Horses, Chickens, Cows & Goats! Experience the balance of peaceful country living with an unbeatable location. Within minutes of restaurants, boutiques, farmers markets, parks and year-round events! Enjoy the breathtaking sunsets, only a short drive from your home to the award winning GULF COAST BEACHES! Just minutes to Sarasota's downtown arts, dining and cultural attractions. Whether you envision a private family compound, a multi-generational retreat, an income-producing opportunity or a flexible live-work estate, this remarkable property offers the rare combination of space, freedom and location. Schedule your private showing today and experience the endless possibilities for yourself. Welcome home to 1516 Fox Creek Dr!

At the end of Westway Drive, where Lido Shores meets the open water of New Pass, 1435 Westway Drive occupies one of Sarasota's most extraordinary waterfront settings. Private, gated, and set on a double lot, the estate captures sweeping views across New Pass toward Longboat Key while offering direct deepwater access to the Gulf of Mexico and Sarasota Bay. This is the rare property that delivers every element of elevated coastal living in one address: boating, privacy, architectural presence, beach access, proximity to St. Armands Circle, and a level of land rarely found on Lido Key. Designed by Brian Phipps and built in 2013, the British West Indies-inspired residence blends timeless coastal architecture with modern luxury. Inside, expansive living spaces are framed by tall ceilings, walls of glass, rich wood flooring, custom millwork, and a natural connection to the water beyond. The great room opens to the waterfront terraces, creating an effortless flow between interior comfort and outdoor living. The kitchen is designed for both daily living and large-scale entertaining, with premium appliances including Sub-Zero and Wolf, generous stone surfaces, custom cabinetry, and an open connection to the main living and dining areas. Whether hosting guests after a day on the boat or enjoying a quiet evening overlooking the water, the home feels equally suited to celebration and retreat. With five bedrooms, two primary suites, and elevator service, the floor plan offers rare flexibility for owners, family, and extended guests. The upper-level owner's retreat is a private sanctuary, complete with a sitting area, wet bar, wine refrigeration, espresso station, study, dual walk-in closets, and a terrace overlooking New Pass, the Gulf, and the lights of Longboat Key beyond. The outdoor living experience is exceptional. Covered terraces, a summer kitchen, resort-style pool, waterfall feature, and waterfront lounge spaces create a private setting designed around the view. The dock includes a 24,000-lb boat lift and additional jet ski lift, placing premier boating waters directly at your door. From here, New Pass provides immediate access to the Gulf, Sarasota Bay, Longboat Key, and the surrounding barrier islands. What truly sets the property apart is its scale. The estate spans approximately three-quarters of an acre, including an adjacent parcel that has been transformed into a lush private garden with mature landscaping, open lawn, fire pit, pond, cascading waterfall, and meandering paths. It gives the home a sense of arrival and breathing room that is almost impossible to recreate in this location. With its own gated access and generous dimensions, this portion of the property also offers future flexibility for a guest house, wellness pavilion, additional structure, or further reimagining, subject to applicable approvals. Lido Shores remains one of Sarasota's most coveted coastal enclaves, known for its architectural pedigree, quiet streets, private beach access, and rare positioning between the Gulf, New Pass, St. Armands Circle, downtown Sarasota, and Longboat Key. Residents enjoy the privacy of a true neighborhood while remaining moments from dining, shopping, boating, beaches, and culture. Previously recognized as an HGTV Ultimate House Hunt winner for waterside living, 1435 Westway Drive is more than a waterfront residence-it is a private Sarasota estate with presence, scale, and a setting that cannot be duplicated.

Like a Picassos' Mona Lisa, a true masterpiece. THIS home is the GEM of all jewels. It is one of a kind, created with artistry-imagination & craftsmanship that simply cannot be replicated. This is not your typical concrete block home. It has warmth, & timeless character. Every detail reflects the skill of master craftsmen whose work has become increasingly rare. Homes of this quality are no longer built, making this residence as exceptional as it is beautiful. In a world filled with contemporary concrete boxes that often lack warmth, personality & charm, this home stands apart. It invites you to slow down, sit back, stay awhile, and savor every moment. It doesn't just provide shelter-it embraces you with comfort, elegance, & a sense of belonging. Warm, ageless, and unforgettable, this is more than a home. It is a work of art that quietly whispers, Stay here...create new memories for a lifetime Timeless Elegance, Effortless Living where HISTORY Meets MODERN LUXURY @ Casa del Carnevale, an exquisite waterfront estate, situated in the prestigious St. Armands Key, a neighborhood of John Ringling Estates. This home seamlessly blends history with modern luxury, offering views of the Sarasota Waterway & Bay with a historic designation. Casa del Carnevale presents a rare opportunity to own an esteemed historical home. Offered for only the fifth time in its storied history, this exceptional estate combines Old World architectural charm with contemporary opulence. The home underwent an extensive renovation, with meticulous attention to detail and craftsmanship, utilizing top-tier materials & artisanship. Expanded from 4,000 to nearly 10,000 sq. ft. under roof & featuring over 7,800 sq. f.t of air-conditioned space, Casa del Carnevale preserves its original charm while offering a reimagined layout that exceeds modern luxury standards. Set on three sprawling lots, 30,000+ square feet, the estate boasts 171 feet of waterfrontage, a private dock lift, a floating lift for jet skis-kayaks, & breathtaking views of Sarasota Waterway. The lush, meticulously designed tropical landscaping creates a private oasis that feels like you are walking in Selby Gardens on St. Armands. The residence includes five bedrooms and six and a half baths across two spacious levels with an elevator. Multiple terraces provide perfect outdoor retreats & entertaining areas, all complemented by stunning garden water vistas, a central courtyard, & an elegant 65' saltwater pool & spa with arched spraying fountains and iridescent glass tiles. Other luxury features include a three-car garage, elevator, nanny's quarters, walk-in wine room, billiards room, office, & custom impact-glass arched windows designed to maximize unobstructed views. The chef's kitchen boasts premium finishes, top-of-the-line appliances, a 5-Star La Cornue range & hood from France, featuring gas or electric ovens (kitchen art). Sub-Zero refrigerators, a Bosch dishwasher, a Miele microwave, a Miele built-in coffee machine, a stand-alone beverage refrigerator, and ice maker. Throughout the home, exposed beams, warm wood tones, natural stone, custom ironwork, Pecky Cypress wood throughout, & curated artwork create an inviting, sophisticated atmosphere, offered furnished. Instant enjoyment to create everlasting memories, Casa del Carnevale is a rare and exquisite blend of history, elegance & modern comfort on one of Sarasota's most coveted waterfront estates. IS A MUST-SEE IN PERSON TO FULLY APPRECIATE.

Designed by renowned Sarasota architect Guy Peterson, this striking contemporary waterfront residence is tucked within the coveted Lido Shores community, where private deeded beach access and protected waters create one of Sarasota's most sought-after coastal lifestyles. Occupying one-and-a-half lots along the tranquil shoreline of Pansy Bayou, the residence blends award-worthy architecture with extensive recent renovations, offering an extraordinary balance of modern design, waterfront living, and effortless indoor-outdoor entertaining. Walls of floor-to-ceiling impact glass capture ever-changing bayou vistas while flooding the home with natural light. Spanning more than 4,600 square feet, the four-bedroom residence has been extensively remodeled from 2020 through 2024 with exceptional attention to detail. New hurricane-rated Viracon glass windows and doors, new stucco, wood flooring throughout, updated plaster walls and ceilings, new roof, elevator servicing all three living levels, new HVAC compressors, and a whole-house 32-kW generator provide peace of mind while preserving the home's clean architectural aesthetic. Sophisticated Ketra lighting adjusts throughout the day to complement natural sunlight, while a distributed audio system, security cameras, alarm system, and integrated smart-home features further elevate everyday living. A dramatic foyer introduces 18-foot ceilings and expansive waterfront views that immediately draw your eye through the residence. The formal living room is anchored by floor-to-ceiling glass framing peaceful water views from nearly every vantage point. The open-concept layout flows effortlessly into the dining area, highlighted by an imported Czech hand-blown glass chandelier, before continuing into the gourmet kitchen and family room. The chef's kitchen is thoughtfully designed with sleek custom cabinetry, stone countertops, oversized center island with seating, newer premium appliances, wine refrigeration, ice maker, two dishwashers, multiple beverage refrigerators, and expansive prep areas. Overlooking the family room with walls of custom built-ins, the space remains connected to the waterfront beyond while maintaining a clean contemporary aesthetic. A sculptural solid-wood staircase with glass railings, together with the elevator, provides access to each level. The second floor is devoted to private accommodations, highlighted by the waterfront primary suite offering its own terrace, walls of glass overlooking the pool and bayou, spacious walk-in closet, and a beautifully reimagined spa-inspired bath. Two additional bedroom suites enjoy private baths, while a fourth bedroom currently serves as a den. The upper levels continue to impress with a private office and full bath opening onto an expansive third-floor terrace overlooking the bay and downtown skyline. Above, the rooftop observation deck captures panoramic views stretching from Sarasota Bay to the Gulf. Outdoor living is every bit as remarkable. A newly constructed IPE waterfront deck extends to the water's edge-positioned closer to the shoreline than would be permitted today-creating an exceptional entertaining venue overlooking the peaceful waterfront. The private dock is equipped with a boat lift. The resort-inspired grounds also feature a heated lap pool, spa, outdoor entertaining pavilion, new irrigation system, extensive landscape lighting, and tranquil garden spaces that perfectly complement the home's modern architecture.

The Gillespie Park Casa del Sol Is Finally on the Market! Nestled beneath a canopy of majestic oaks in Sarasota's beloved and historic Gillespie Park, Casa del Sol is an extraordinary Mediterranean-inspired estate where timeless architecture, modern luxury, and resort-style living come together just moments from the heart of downtown. Built in 2007 with solid masonry construction, this remarkable property offers 3,338 total square feet, including a 2,854-square-foot main residence, a beautifully appointed 484-square-foot detached studio casita resting above the spacious detached 2 car garage w/covered carport. This 4 bedrooms, 4.5 bathrooms, is offered for under $2 million. Designed to capture the romance of an authentic Mediterranean villa, the home showcases imported Colombian roof tiles, handcrafted Colombian brick pavers, rich hardwood flooring, elegant French doors, a chef's kitchen with stainless steel appliances, a gas range and fireplace, dual-zone HVAC, a tankless water heater, and a convenient second-floor laundry room. Every detail reflects exceptional craftsmanship while blending seamlessly with today's modern lifestyle. Step outside to your own private tropical retreat, where lush landscaping, a sparkling heated pool (with fountain water feature), and a newly installed privacy fence create an atmosphere of serenity and effortless entertaining. The detached studio casita offers outstanding flexibility as a luxurious guest suite, executive office, fitness studio, creative space, or income-producing accommodation. It is separately metered for convenience. Just a 2 min walk from the 10-acre John Hamilton Gillespie Park and a 2 minute drive (or short walk or bike ride) from Downtown Main Street and Sarasota's award-winning restaurants, boutiques, theaters, galleries, waterfront, and renowned Farmers Market, Casa del Sol places the very best of Sarasota at your doorstep. Located within the desirable Downtown Neighborhood (DTN) zoning district allowing one-week minimum short-term rentals, the property presents a rare opportunity as a primary residence, seasonal escape, or exceptional investment. Rarely does a home provide this level of architectural distinction, walkable downtown convenience, investment flexibility, and resort-inspired living. Casa del Sol is finally on the market, offering an extraordinary opportunity to experience one of Sarasota's most coveted lifestyles.

This Spanish Mediterranean style home built in 1925 is nestled in the coveted West of Trail subdivision of DeSota Park in the South Poinsettia park Neighborhood just two blocks from the fine dining and boutique shopping offered in Southside Village. This home is ideally located outside of any flood zones and weathered the 2024 hurricane season without any damage.This listed historic home with detached casita is rich with character. The beautifully designed residence offers 2,330 square feet of living space. The home boasts a total of 12 rooms featuring a spacious entry, open plan living area including a formal dining room, living space and chef's kitchen and a versatile family room located directly off the pool area. The 3 bedroom main house has 2 bedrooms with their own en-suite bathrooms plus an additional 3rd bedroom/office/flex space, updated hurricane rated windows and whole home tankless hot water heater. The casita offers the 4th bedroom with en suite bath and kitchenette. Upon entering the tiled courtyard you are invited to step inside and discover an abundance of architectural details like the hurricane rated pecky cypress entry door, arched doorways, pecky cypress beams and fireplace mantel, custom built-ins and original architectural details that all add up to the unique touches of sophistication. The northern exposure fills the home with natural light, highlighting the garden views through casement dual pane hurricane rated windows adorned with tasteful and functional window treatments.Inside the spacious foyer your attention is drawn to the custom window treatments and new flooring and opens to an expansive open plan living room featuring a working fireplace with a pecky cypress mantel that adds warmth and ambiance and pecky cypress beams. The living space is flanked by a light filled dining room that opens to a second private courtyard and the recently renovated gourmet chef's kitchen that includes custom cabinetry, Taj Mahal quartzite countertops, zellige tile backsplash and top of the line appliances - SubZero refrigerator, Thermador warming drawer and Italian Fulgor Milano gas range. Down the hall the main floor primary suite includes a large ensuite bathroom with a separate shower, four closets for ample storage and a convenient laundry space. The second bedroom suite is tucked away with dual closets, dressing area, its own courtyard and private access to the pool. At the back of the home the 3rd bedroom/office/flexroom is located off a large and comfortable family room with pecky cypress beams and tile flooring that opens up through a wall of hurricane rated stack glass back doors to the pool area. The pool area is a tropical paradise featuring a heated pool and hot tub with a new remote controlled electronic system. The pool cage encompasses plenty of space for lounging and dining and includes the entry to the casita and full bath with mini split unit, tile flooring and wooden beams, includes built-in murphy bed and a dedicated generator. Outside the casita is a large paver courtyard with a custom outdoor cooking area that includes a plumbed 36 natural gas grill with rotisserie and pizza oven accessories and an outdoor refrigerator. This West of Trail home is ideally located in the Southside Elementary School district, convenient to Sarasota Memorial Hospital and located just steps away from Morton's Gourmet Grocery and some of Sarasota's best restaurants, shopping and art galleries.

This tastefully updated and remodeled single story home is ideally located within the sought after Bird Key neighborhood. Set on a large corner lot, it features a clean, contemporary style that feels both current and easy to live in. The home offers three bedrooms, two and a half bathrooms, and a two car garage, creating a comfortable and well balanced living environment. Inside, the open concept split floor plan provides both flow and definition, with separate living and family rooms suited to modern living. The remodeled kitchen features quartz countertops and sleek contemporary cabinetry and is centrally positioned to connect the main living, dining, and family spaces. Both living areas open through impact sliding glass doors to the lanai and pool, creating an easy transition between indoor and outdoor living. Fully opening sliders from the living and family rooms extend the space onto the pool deck, making the home particularly well suited for entertaining. The primary suite includes a spacious bedroom, walk in closet, and an updated en suite bathroom. Two additional guest bedrooms and a bathroom are located on the opposite side of the home, offering privacy for family and guests. The generously sized family room easily incorporates a small home office area. Recent improvements include a new tile roof in 2025, whole house propane generator 2025, a newer air conditioning system in 2023, and impact windows for added security and peace of mind. Bird Key offers one of Sarasota's most desirable locations, just minutes from downtown Sarasota, St. Armands Circle, and Lido Beach. Residents also benefit from the nearby Bird Key Yacht Club, currently undergoing a full redevelopment and expected to reopen early in 2027 as a premier destination for boating, tennis, and social activities. PLEASE NOTE FRONT DOOR ENTRY IS LOCATED ON BOBWHITE WAY.

Exotic and extremely private bay front property on the market for the first time in 40 years. In fact, this is only the third time it's been available in 100 years. Travel back in time to find ancient oaks and large palms, Banyans, and cedars. It's an idyllic paradise reminding us of why people have come to these shores for millennia. Even the beachfront appears unadulterated as do several others along Sarasota's north shore. Although this is direct waterfront, most of the land is not in the flood zone creating many possibilities for new structures on or near grade. What is most unique is the 444-foot lot depth. This is almost 4 times that of other bayfront parcels being redeveloped in the area. This extreme distance provides complete privacy from Bay Shore Road and with each adjacent property a multi-acre estate, the feeling of spaciousness and seclusion is complete. Leave the world behind on the long, winding shell drive through tree canopy and lush vegetation. At the end of the road is the original homesite on a small bluff directly on and overlooking Sarasota Bay. Your views are of Longboat and Lido Key and out New Pass to the Gulf of Mexico. Looking south you see our bustling little city of Sarasota and the John Ringling Bridge. Enjoy sea breezes in the afternoon and sunsets all year round. The original home on property evokes a bygone era but land values, building codes and FEMA regulations point toward new construction. A parcel like this is an architects dream providing the size necessary to create what anyone might want, elevation allowing cascading terraces down to the waterfront and multiple, potential footprints for accessory dwellings, accessory structures and more. Bay Shore Road has become an eclectic location for the grandest homes in Sarasota. This has led to sales over 10 million dollars and have exceeded 15 million. But you could not put a price on the most spectacular neighbor, Ca' d Zan. John Ringling's gilded Venetian palace anchors the neighborhood to the north and downtown Sarasota is just 2 miles south. Other nearby cultural & educational institutions include the Ringling Museum of Art, the Asolo Theater of Performing Arts, the Sarasota Ballet, the Ringling College of Art & Design and our newest amenity, The Bay Park Conservancy redeveloping 53 acres of City waterfront into a world class public park.

Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides exceptional convenience to the bridge, mainland, and all that the island has to offer. The home features 4 bedrooms and 4.5 bathrooms, with the upper level remaining intact and in great condition. The ground level experienced flooding during the recent hurricanes; however, the seller has already completed professional remediation, providing a clean slate for updates and renovations to suit your vision. Situated on a protected deep-water basin, the property is ideal for boating and waterfront living, complete with a private dock, no fixed bridges, and direct access just minutes to the Gulf. The home also features a pool, offering the perfect foundation to create a true coastal retreat. This is a unique opportunity to secure a well-located waterfront property and finish it to your exact specifications in one of Siesta Key’s most desirable communities.

This is over FIVE ACRES in one of Sarasota's most PRIVATE communities, where seeing deer in your backyard is normal, the only traffic you'll hear is birds, and you can finally enjoy the kind of quiet that's becoming incredibly hard to find. Even though it feels like you're miles away from everything, you're less than 15 minutes from groceries and restaurants around Lakewood Ranch, about 25 minutes from downtown Sarasota, and roughly 30 minutes from Siesta Key Beach. You really don't have to choose between CONVENIENCE and PRIVACY anymore. Inside, the home is just over 4,000 square feet with FOUR bedrooms, FOUR bathrooms, plus BONUS room and LOFT space, soaring ceilings, and an open floor plan that was designed for both everyday living and entertaining. The chef's kitchen flows into the great room, while the covered lanai and saltwater pool become an extension of the living space. This home was CUSTOM built in 2016 with hurricane resilience in mind. It features IMPACT windows and doors throughout, a whole-house GENERATOR, and it's about 42' elevated and NOT in a flood zone. When everyone else is worrying about storms, this is the kind of home designed to help you feel prepared. You're just minutes from Lakewood Ranch, but without the high HOA and CDD fees or the cookie-cutter neighborhoods where the view out your window is the side of your neighbor's house. Here there's room to throw the ball, have a garden, or play in the treehouse. Sitting on more than FIVE ACRES, you have room to dream. Add a barn, create a homestead, bring horses, build another structure, or simply leave it exactly as it is and enjoy the PRIVACY that comes with owning this much land. Nestled within The Ranches at Bern Creek neighborhood which has all properties 5-10 acres in size, you will always maintain your peace, even when new development starts filling in around the area. Finding a beautiful custom home with acreage and just a short drive to Lakewood Ranch, downtown, and the beaches-with this level of privacy, hurricane preparedness, low HOA fees, and a location that's still convenient to everything Sarasota has to offer-is incredibly rare.

Nestled behind the gates of one of Palmer Ranch's most esteemed neighborhoods, this exceptional John Cannon custom home in Silver Oak offers the perfect blend of timeless architecture, modern luxury and lasting value. Spanning more than 3,800 sf, this meticulously renovated residence features 4 bedrooms, 3.5 baths, a private study and a spacious game room - all on one level! Completely reimagined in 2026, nearly every major component of the home has been replaced or upgraded, creating a truly turnkey residence with exceptional craftsmanship throughout. Rich handcrafted hardwood flooring flows seamlessly from room to room, complemented by custom Fabuwood cabinetry, Cambria quartz countertops and refined designer finishes. The first glance of luxury greets you at the entry with new arched iron doors. Inside you'll find 12ft ceilings with custom wall coverings and lighting - with views to the pool and preserve. At the heart of the home, the curated kitchen is outfitted with a premium Wolf gas range, GE Monogram refrigerator, Cove dishwasher, double ovens, Scotsman ice maker and a beverage center. The primary suite is a luxurious retreat with wonderful light and outdoor views - complete with a custom California Closets walk-in closet that's truly over the top. The spa-inspired bath is magazine worthy - featuring a gradient tiled wall, double vanities, soaking tub, oversized shower and Cambria countertops. A handsome study provides the perfect home office or library, while the expansive game room offers additional space for recreation, media or another suite. Stunning living spaces feature a well-designed bar, electric fireplaces that add warmth and ambiance and views to the private preserve. The split plan provides three additional suites providing privacy to guests and family. Outdoor living is equally impressive. The resort-style pool has been completely resurfaced with new waterline tile and is surrounded by elegant Blanco marble lanai decking beneath a newly constructed screen enclosure-creating an inviting outdoor oasis for year-round entertaining. The large preserve lot offers privacy and long range views - with new landscaping. The 3-car side load garage has high ceilings, storage galore and is air conditioned. Built for both beauty and peace of mind, the home features a newer roof (2025), new HVAC system with all-new ductwork (2026), complete attic re-pipe, PGT hurricane-impact windows and sliding doors (2026), a hurricane-rated Suncoast Iron front entry door (2026) and a motorized hurricane screen system protecting the lanai (2026). Silver Oak is a sought-after community featuring custom builds, oversized homesites, mature trees, gated access and low HOAs. Close to shopping, top-rated schools and the Legacy Trail for walking, biking and exploring. 8986 Bloomfield Boulevard is more than a beautifully updated home-it's a rare opportunity to enjoy the prestige and charm of an established neighborhood with the confidence and comfort of a home rarely found updated to this level! The work has been done - simply move in, unpack, and start enjoying the Sarasota lifestyle!

Architectural elegance abounds in this John Cannon custom built pool home in Silver Oak on Palmer ranch. Situated on a very private & quiet lot backed by pond view & acres of protected preserve. Nearly 3200 sq. ft. under air features 4 bedrooms plus an office with built in desk area & 3full baths. You will enjoy the expansive primary bedroom. Recent upgrades including a new tile roof in 2019, 2 new AC systems, pool/spa updated with new Pebble Tec finish, new stairs & railings, LED lanai lights & more. Paver brick lanai with new outdoor kitchen. Upon entering this home you will be greeted by soaring ceilings, artistic trays & architectural details indicative of John Cannon Homes. Family room features gas fireplace, fully pocketing sliders opening the entire living room up to the outside lanai. New Cambria counters in kitchen & DR, kitchen island at counter height & upgraded stainless steel appliances. Hurricane protection throughout for low insurance costs. Over size side entry 3 car garage. Pool cage upgraded with no-see-um screens & stronger structural integrity. Many other upgrades to please the most discriminating buyers. Located in the heart of Palmer Ranch near shopping, Legacy Bike Trail & world famous Siesta Key Beach.

Perfectly positioned along the water, this exceptional residence offers a refined coastal lifestyle just moments from Siesta Key. Tucked away on a quiet street, the contemporary home enjoys southern exposure and approximately 100 feet of canal frontage with direct access to Sarasota Bay. Designed for both entertaining and everyday living, the open-concept interior features soaring ceilings exceeding 14 feet and expansive walls of impact-rated pocketing glass. When opened, the living areas flow seamlessly to a covered outdoor lounge, resort-style pool and spa, and a fully equipped outdoor kitchen, creating effortless indoor-outdoor living. The primary suite is privately located on the east side of the home and features oversized windows and glass sliders opening directly to the waterfront pool terrace, along with a custom walk-in closet and spa-inspired en-suite bath. On the west wing, two sun-filled guest bedrooms with walk-in closets share a beautifully appointed bathroom. A flexible bonus or media room serves as a fourth bedroom and includes an en-suite bath and walk-in closet. Additional features include a dedicated study or den, a fully air-conditioned split three-car garage, and thoughtfully designed spaces that balance style and functionality. With direct boating access to the Intracoastal and no HOA restrictions, this property offers an ideal waterfront lifestyle. Enjoy daily sunsets over the water and front-row views of Siesta Key's Fourth of July fireworks-all from the comfort of your own home. Conveniently located minutes from Siesta Key Beach, Downtown Sarasota, and premier dining, shopping, and cultural destinations-including The Bay Park, Selby Gardens, and the Van Wezel Performing Arts Hall-this home presents a rare opportunity to enjoy contemporary design, privacy, and boating access in a sought-after coastal setting.

Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis-peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota's vibrant arts and culture scene.

This home truly has it all - space, privacy, layout made for everyday living and entertaining! This is a rare opportunity to own a private, estate-sized home on over an acre in Sarasota-quietly tucked inside the gated community of Beneva Oaks at the end of a cul-de-sac. Set back from the road and surrounded by towering oak trees, the property offers a sense of peace, space, and privacy that makes it easy to feel at home the moment you arrive. Built in 1980 by a professional builder for his own family, the home was intentionally created to fully enjoy the beauty, shade, and tranquility of the property-something that can be felt throughout the home. With more than 5,200 square feet of living space, the interior offers a versatile layout designed to bring people together while still allowing room to spread out. A welcoming foyer with a graceful spiral staircase sets the tone, opening to multiple living areas ideal for hosting holidays, celebrating milestones, or enjoying everyday moments with family. The formal dining room provides a beautiful setting for special gatherings, while the eat-in kitchen serves as the heart of the home, featuring double ovens, a separate Sub-Zero refrigerator and freezer, and views of the lush backyard. The main-level primary suite offers a peaceful retreat, complete with a sitting area and a renovated spa-style bathroom with a freestanding soaking tub and custom walk-in shower. A first-floor office with custom built-ins and surround sound adds flexibility for working from home or creative use. Upstairs, four additional bedrooms, two full baths, and a flexible bonus space provide extra room for guests or hobbies. Three bedrooms open onto a screened balcony, while an additional open balcony invites quiet moments to unwind and take in the surrounding greenery. Outdoor living is an extension of the home itself, with a screened lanai, resurfaced saltwater pool, Trex decking, and paver walkways creating a setting for both entertaining and everyday relaxation. The backyard is bordered by city-owned green space beyond the rear wall, enhancing privacy and reinforcing the feeling of a natural retreat. Thoughtful updates throughout include new flooring, renovated bathrooms, four zoned air-conditioning systems, tankless water heaters, updated irrigation with a private well, a replaced septic system, a newer roof, and maintained fencing. A circular driveway and three-car side-entry garage completes the property Thoughtfully designed, surrounded by nature, and brimming with comfort...your new home awaits!

Virtually Staged. Nestled within the exclusive enclave of Regent Lake, an intimate community of just 13 residences, this exceptional lakefront estate offers a rare opportunity to enjoy refined living on more than an acre overlooking a picturesque spring fed lake. Showcasing the sought after Osprey floor plan, this thoughtfully designed four bedroom, three bathroom residence spans more than 3,100 square feet and includes a private office, an oversized three car garage, and a split floor plan that balances elegant entertaining with everyday comfort. A long approach welcomes you to a setting defined by privacy, tranquility, and sweeping water views. Inside, the spacious living areas are thoughtfully designed to capture the beauty of the surrounding landscape while providing an inviting flow for both everyday living and entertaining. The gourmet kitchen is the heart of the home, featuring granite countertops, custom wood cabinetry, stainless steel appliances, a built in oven and microwave, cooktop, walk in pantry, center island, breakfast bar, and a charming morning room overlooking the grounds. The primary suite serves as a peaceful retreat with direct access to the lanai and pool, serene lake views, dual closets, dual vanities, a soaking tub, and a separate walk in shower. Designed to embrace Florida's indoor outdoor lifestyle, the screened lanai and sparkling pool provide the perfect backdrop for entertaining or quiet evenings watching spectacular sunsets over the water. The expansive homesite offers a private fenced area for pets and abundant opportunities to enjoy the natural beauty and wildlife surrounding the lake. Thoughtful improvements include a new air conditioner and water heater in 2025, Bahama hurricane shutters, a whole house generator with a buried 500 gallon propane tank, a reinforced 150 mile per hour rated garage door, added attic insulation, and beautiful new flooring throughout all bedrooms. With low HOA fees, no CDD fees, and a location just minutes from shopping, dining, top rated schools, and Sarasota's world renowned beaches, this is more than a home. It is an opportunity to enjoy the privacy of an estate sized waterfront home with the convenience of city amenities nearby.

Introducing THE RETREAT, a stunning two-story residence. FOUR (4) bedroom, THREE (3) bath. Paver driveway, 3 CAR GARAGE, LVP flooring. Home has been professionally staged. Pool size is 12 x 26 , leaving plenty of green space for pets in the backyard! Back yard fence will fully enclose the back yard with gates on both sides of the home. This exceptional new build boasts superior block construction, a durable metal roof, impact-resistant windows, doors, and sliders. Inside is a thoughtfully designed open floor plan, featuring soaring 10-foot ceilings and elegant 8-foot solid core doors that enhance the home's impressiveness. The gourmet kitchen is complete with a 6-foot island, luxurious quartz countertops, custom shaker cabinetry, and a top-of-the-line appliance package, perfect for both daily meals and entertaining. The primary bedroom, located on the main level, is a serene retreat with stunning tray ceilings, large his/her walk-in closets, double vanity, and a spacious walk-in shower. Bedroom 2, also on the first floor, is versatile and can serve as an additional bedroom or a home office. Upstairs, you'll find two more generously sized bedrooms that share a beautifully appointed full bathroom. The home's detailed interior is complemented by luxury vinyl plank flooring throughout both levels, providing durability and style. Outdoors, a gas-heated saltwater pool and paver deck creates the ideal setting for relaxation and entertainment. Conveniently located with easy access to downtown Sarasota, the Legacy Trail, Payne Park, Sarasota Memorial Hospital, and the world-renowned beaches of Longboat and Siesta Keys, this home offers the perfect blend of luxury, comfort, and convenience for modern family living. Experience elevated living at its finest in your RETREAT!

A rare opportunity to own a one of a kind custom built residence in the heart of downtown Sarasota, 1680 Cherry Lane is tucked into one of Laurel Park's most charming streets while being just moments from everything that makes downtown so special. Blending timeless architecture with modern luxury, this brand new residence offers an exceptional lifestyle defined by thoughtful design, refined finishes, and one of Sarasota's most coveted locations.Spanning 3,128 square feet, this thoughtfully designed two story home features five bedrooms and four bathrooms, including a first floor primary suite and an additional main level bedroom that can easily function as a private office, guest suite, or den. Upstairs, three additional bedrooms provide flexibility for family, guests, or multigenerational living, creating a floor plan that is equally suited for everyday living and entertaining.At the heart of the home, the open concept living spaces are centered around a beautifully appointed chef's kitchen featuring premium Thermador appliances, custom cabinetry, quartzite countertops, and an oversized island that seamlessly connects the kitchen, dining, and living areas. Expansive PGT impact rated windows and doors flood the home with natural light while creating a seamless connection to the outdoor living spaces, while the private pool provide the perfect backdrop for year round entertaining and relaxation.Located within the highly sought after Southside Elementary School district, this exceptional residence is just minutes from downtown Sarasota's acclaimed restaurants, boutique shopping, Burns Court, Bayfront Park, Marina Jack, the city's vibrant arts and cultural scene, and Sarasota's world renowned Gulf beaches. Combining custom craftsmanship, luxury finishes, and an unbeatable location, 1680 Cherry Lane presents a rare opportunity to own a brand new custom home in one of Sarasota's most desirable neighborhoods.

Virtually Staged. Rare brand-new construction in the heart of Laurel Park, 1681 Oak Street offers the ideal blend of modern luxury, thoughtful functionality, and an unbeatable downtown Sarasota lifestyle. Perfectly positioned in one of Sarasota’s most sought-after neighborhoods, this newly built residence places you just moments from downtown dining, shopping, Bayfront Park, Burns Court, Marina Jack, and Sarasota’s world-renowned Gulf beaches, while offering the charm and convenience of coveted downtown living.Spanning 3,128 square feet, the thoughtfully designed two-story floor plan features five bedrooms and four baths, including a first-floor primary suite and an additional main-level bedroom that can easily function as a private office, guest suite, or den. Upstairs, three additional bedrooms provide flexibility for family, guests, or multigenerational living, creating a layout that balances everyday comfort with long-term versatility.Designed for both elevated entertaining and daily living, the open-concept interior is centered around a beautifully appointed kitchen with premium Thermador appliances, custom cabinetry, quartzite surfaces, and seamless connection to the main living spaces. Expansive impact-rated PGT windows and doors fill the home with natural light while providing peace of mind and enhancing the home’s clean, modern aesthetic.Outside, a serene private pool creates a true backyard retreat and extends the living experience outdoors for year-round enjoyment. Whether hosting friends after dinner downtown or enjoying a quiet afternoon at home, the outdoor setting offers the perfect balance of privacy and relaxation.Located within the highly sought-after Southside Elementary School district and just minutes from Sarasota’s beaches, cultural amenities, restaurants, parks, and waterfront, 1681 Oak Street presents a rare opportunity to own a newly built home in Laurel Park, where quality construction, location, and lifestyle come together in one exceptional offering.

Waterfront property. Build your dream custom home with Skyline Custom Development, an unmatched luxury waterfront home contractor/specialist. Quietly nestled in one of Sarasota's most treasured neighborhoods, Cherokee Park, this lot sits on a secluded street outlined with beautiful banyan and canopy trees. This coveted property features mature landscaping and offers 100 feet of water frontage on a canal that opens up to the magical waters of Sarasota Bay. Additionally, this property contains a brand new seawall and dock. An ideal centrally located property just a bike ride away from the world-renowned beaches of Siesta Key and trendy downtown Sarasota. *Existing structure to be removed. ***Subject property to be divided, existing home to be torn down.

Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key's coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet chef's kitchen, which features a quartz waterfall island, custom cabinetry, and high-end appliances. **Expansive sliding glass doors open to over 1,200 square feet of covered outdoor living space, framing views of lush tropical landscaping and a resort-style pool with a sun shelf. The primary suite is a true sanctuary, complete with a free-standing soaking tub and an oversized walk-in shower. The outdoor living experience is unrivaled. Multiple covered lanais and balconies provide perfect spaces for entertaining, relaxing with morning coffee, or enjoying Sarasota's sunsets. **Additional features include an elevator servicing all three levels, additional guest suites, flexible bonus spaces, a two-car garage, and storm-rated windows and doors for elevated construction. Stylish coastal architecture with Hardie board siding and a metal roof completes the package. **Located just steps from Siesta Key's world-famous beaches and minutes from the vibrant shops and restaurants of Siesta Village, this location offers the perfect blend of luxury and island lifestyle. **Short-term rentals are permitted, providing a flexible investment opportunity. **This property is also conveniently located in close proximity to Downtown Sarasota, Southside Village, and top hospitals, restaurants, and entertainment. This is your chance to build a custom masterpiece in a truly unparalleled location. Build your dream home with us, or purchase the lot and plans separately. Use our trusted general contractor or bring your own builder. Are you ready to turn your vision into a reality?

Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougainvillea Street. Occupying three lots, it is nestled gracefully in Sarasota's most cherished neighborhood. Set on a tranquil, tree-lined avenue, moments from vibrant Southside Village, Sarasota Memorial Hospital, and the renowned sands of Siesta Key, this thoughtfully enhanced residence exudes a rare character and allure that newer homes simply cannot replicate. From the moment you step inside, you're captivated by a refined blend of historic charm and contemporary luxury. Rich hardwood flooring, detailed crown moldings, and designer lighting create a warm and refined ambiance throughout the spacious, open-concept layout. Anchoring this home is a beautifully reimagined gourmet chef's kitchen, showcasing high-end stainless steel appliances, luminous granite countertops, bespoke cabinetry, and an expansive island-ideally suited for gatherings both grand and intimate. The luxurious master suite is a serene retreat, illuminated by abundant natural light and offering generous closet space alongside a spa-inspired ensuite with a sumptuous walk-in shower and dual vanities. Additional bedrooms and versatile living areas effortlessly accommodate family, guests, or a tailored home office. Unique to this remarkable residence is the thoughtfully designed separate living quarters, complete with a private entrance, an inviting bedroom, a fully equipped kitchen, and a full bathroom. Ideal for hosting guests, housing extended family, or offering privacy to long-term visitors, these quarters are unique. Outside, the magic only continues-enchanting gardens burst with colorful bougainvillea, and mature greenery surrounds an inviting patio that effortlessly extends the living space outdoors, perfect for sunlit gatherings or quiet moments beneath Sarasota's famous skies. With meticulous care and modern upgrades, including a newer roof, advanced HVAC systems with two newly installed air conditioning units, recently replaced front-facing windows, and fully updated plumbing and electrical infrastructure, this home blends historic character with contemporary convenience, ensuring comfort, efficiency, and peace of mind. 1829 Bougainvillea Street represents more than just a renowned address; it offers a rare opportunity to own a property rich in Sarasota history and charm, distinctively set apart from uniformity and infused with authentic character. Welcome home to an extraordinary residence awaiting your personal story. Its roots run deep into our community. The prior owners have all remained friends to this day, and the resurgence of the modern cottage is now at the forefront of interior design and architecture. This property embodies that trend in a way no other home can. A true one-of-a-kind that will never be replicated.

A Key West-inspired waterfront retreat in prestigious Bird Key, this residence blends timeless coastal design with extensive updates and exceptional indoor-outdoor living. Set along 101 feet of canal frontage with direct access to Sarasota Bay, the property offers a rare opportunity to enjoy a boating lifestyle in one of the area's most sought-after neighborhoods. Manicured landscaping and inviting front porches introduce the home's architectural charm, while inside, nearly 3,400 square feet of living space unfolds across two levels (furnishings may be purchased separately). Beautiful hardwood flooring connects the open layout, where vaulted ceilings, skylights, and impact-rated PGT windows and doors fill the interiors with natural light. The double glass and solid wood entry opens to a bright, contemporary living space that flows effortlessly into the formal dining area. At the heart of the home, the eat-in chef's kitchen is thoughtfully designed with shaker-style cabinetry, quartz countertops, stainless steel appliances, a center island, and a breakfast bar peninsula. A dedicated cafe-style dining area is complemented by a wet bar featuring dual wine cooler/beverage refrigerator, and floating shelving. Impact sliding glass doors open to the covered outdoor entertaining area and pool deck beyond. This inviting space overlooks the family room. Upstairs, the oversized primary suite offers a private retreat with terrace access, a spacious en-suite bathroom, and a walk-in closet. A second en-suite bedroom also enjoys its own terrace, while two additional guest bedrooms share a third bath, providing flexibility for family and visitors. Outdoor living is designed for both relaxation and entertaining. The heated swimming pool is surrounded by a brick paver deck, with an additional open deck ideal for lounging. Just beyond, the extended dock and newly reinforced seawall (2025) create a seamless connection to the water, offering direct access to the waterway that flows out to Sarasota Bay, for boating and waterfront enjoyment. A long list of improvements enhances the home's value and peace of mind, including a 2023 metal roof, impact PGT windows and doors, updated mechanical systems, and recent exterior upgrades such as new soffit, fascia, and gutters (2026). Bird Key is known for its central location between downtown Sarasota and St. Armands Circle, offering residents convenient access to waterfront dining, boutique shopping, and cultural venues. Just minutes away, Lido Beach and Longboat Key provide some of the region's most celebrated Gulf-front shorelines, while nearby marinas and yacht clubs complement the boating lifestyle that defines this exceptional community.

Experience modern luxury at its finest in this exceptional 5-bedroom, 3.5-bath residence which redefines modern luxury through innovative design, advanced technology, and uncompromising construction. Thoughtfully designed and constructed in 2022, built of concrete and protected by impact-rated hurricane windows and doors, this home offers outstanding durability, efficiency, and peace of mind. Ideally situated in a premier location, offering convenient access to highly rated hospitals, top-performing schools, exceptional dining destinations, and a vibrant cultural arts scene. Inside, nearly 2,600 square feet of thoughtfully designed living space unfolds beneath soaring two-story ceilings and dramatic glass windows creating a breathtaking sense of openness flooding the main living spaces with natural light and picturesque views of the surrounding landscape. Clean architectural lines, minimalist linear slot vents, and carefully curated finishes create a sophisticated contemporary aesthetic. The main level features three well-appointed bedrooms, while the upper floor offers two spacious bedrooms connected by a full Jack and Jill bathroom-an ideal layout for private guests' accommodations, home offices, or flexible living space. Designed for effortless living, the fully integrated smart home system provides remote access to programable lighting, surround sound, security, climate control, motorized window treatments, and a concealed drop-down projector screen that transforms the main living area into a private theater experience. Foam-insulated walls provide enhanced sound attenuation and energy efficiency, while dual-zoned HVAC systems with UV filtration ensure personalized year-round comfort and superior indoor air quality. The chef's kitchen showcases premium Thermador appliances, a built-in island microwave, elegant white quartz countertops, and an expansive breakfast bar ideal for entertaining and everyday living. Additional practical features include generous under-stair storage, whole-house water filtration, integrated surround sound with AirPlay connectivity, and a dedicated washer and dryer within the primary suite in addition to the main laundry area. The home is also equipped with interior and exterior power infrastructure for high-voltage EV charging, providing convenience for current and future electric vehicle owners. The luxurious primary retreat is designed as a private sanctuary, complete with a built-in white noise system and spa-inspired amenities. All three full bathroom features walk in showers, heated towel rails and under-vanity air heaters, elevating everyday comfort to a resort-like experience. Outdoor living is equally impressive. A spacious covered patio overlooks a stunning screened lap pool with panoramic screening that maximizes views while maintaining comfort and privacy. The pool area includes an outdoor shower, underwater sound system and lighting, while the fully built-in outdoor kitchen creates the perfect setting for entertaining year-round. The home is fully fenced with low-maintenance landscaping, complemented by a minimalist garden design and premium artificial turf, provides beauty without the upkeep. Combining architectural excellence, cutting-edge technology, energy-efficient construction, an unbeatable location, and exceptional indoor-outdoor living, this remarkable home offers a rare opportunity to enjoy modern luxury without compromise.

Experience modern luxury in this stunning new construction home located in Sarasota's highly sought-after West of Trail area. Offering 5 bedrooms, 5.5 bathrooms, and 4,165 square feet under air (5,614 total square feet), this exceptional residence combines custom design with everyday functionality.A grand entry welcomes you with soaring 12-foot ceilings, a spacious foyer, and a striking staircase that sets the tone for the home's contemporary elegance. The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating the perfect space for entertaining and daily living. The chef-inspired kitchen features custom solid wood cabinetry, quartz countertops, premium Thermador appliances, and an oversized island designed for gathering with family and friends. A custom built-in feature wall in the living room adds both style and practicality.The bright first-floor office, complete with convenient bathroom access, can easily function as a guest suite and overlooks the beautifully landscaped front yard. Upstairs, 10-foot ceilings enhance the spacious feel throughout. The luxurious primary suite serves as a private retreat, accessed through double doors and opening to a private balcony that extends the second-floor living space. Each additional bedroom offers its own en-suite bathroom and walk-in closet, providing comfort and privacy for family and guests alike. A spacious second-floor laundry room with built-in cabinetry adds convenience.Outside, lush tropical landscaping and a full irrigation system complement the home's impressive curb appeal. Premium upgrades include impact-rated windows and doors, epoxy-coated garage floors, designer exterior lighting, pre-wiring for security cameras, and dual HVAC systems for enhanced comfort and energy efficiency.Ideally located West of Trail, this exceptional home is just minutes from downtown Sarasota, Sarasota Memorial Hospital, premier dining and shopping, local parks, and the world-renowned beaches of Siesta Key. Schedule your private showing today and discover the perfect blend of luxury, location, and modern living.