Mikelchaffeerealtor.com Search Results

Meticulously designed and flawlessly executed, this exceptional 6,700-square-foot palatial estate on iconic Westway Drive is majestic. Nestled in Lido Shores, the property spans an impressive 1.67 acres—making it among the largest and most desirable waterfront holdings in the Lido/Longboat area. With a premier western exposure and sweeping waterfront frontage, the property offers unobstructed, panoramic views of Sarasota’s legendary sunsets and the Gulf of Mexico's ever-changing beauty. Architectural brilliance is evident in every aspect of the estate’s design, as classic Mediterranean influences blend with graceful elegance. Security and exclusivity are paramount, ensuring that every moment in this sanctuary is one of tranquility and distinction. A regal, gated entrance creates a dramatic sense of arrival, while the privileged location ensures seclusion and prominence along spectacular waterways and pristine Gulf Coast shorelines. The long driveway winds through mature, manicured landscaping—lush with live oaks, sabal palms, palmettos, and ferns, all illuminated by dramatic night lighting. The home’s brick-paved courtyard presentation is adorned with stately columns and intricate detailing, setting a tone of timeless sophistication that echoes throughout the property. A stately portico welcomes with a monumental carved-wood entry door that sets the tone for sophisticated interiors. Inside, grand rooms feature exquisite fixtures, polished finishes, and rich furnishings, unified by an elegantly styled aesthetic and an atmosphere of refined opulence. Every detail reflects a commitment to luxury, comfort, and timeless style. Stunning examples include exquisite marble and wood flooring, a sweeping curved staircase with iron railing, arched windows and doors, artisan millwork, high ceilings with custom details, triple crown molding, and bespoke cabinetry that embellish the home throughout. With three expansive levels, the residence boasts four en suite bedrooms, an attached 770-square-foot VIP apartment secluded from the rest of the house, two additional baths, dual living rooms, three formal and casual dining areas, three offices, a vast recreation room, a gym, two laundry rooms, an elevator, two fireplaces, a three-car garage, and dozens of French doors and glass sliders that open to invite the incredible outdoors in. Expansive covered terraces and upper-level balconies stretch along the rear façade, offering multiple spaces for outdoor living and entertaining—perfect for both lavish celebrations and intimate gatherings. Outdoor living unfolds effortlessly with a sleek pool and spa, inviting lounges, open-air dining areas, and voluminous acreage that add to the options and appeal of waterfront living. Every aspect of the residence, from its expansive footprint to its gilded amenities, has been thoughtfully designed to deliver a lifestyle of unrivaled sophistication, comfort, and exclusivity. This coastal refuge offers an irreplaceable opportunity in Sarasota’s elite waterfront market. The estate’s enviable location offers easy access to Sarasota’s world-class beaches, the downtown’s vibrant cultural scene, and the boutique shopping and fine dining venues of St. Armands Circle. This exceptional listing is truly stunning, perfect for a luxurious lifestyle in a magnificent setting. A must-see in person to fully appreciate its wonderful allure and unique characteristics.

4 Beds ⋅ 7 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code

Meticulously designed and flawlessly executed, this exceptional 6,700-square-foot palatial estate on iconic Westway Drive is majestic. Nestled in Lido Shores, the property spans an impressive 1.67 acres—making it among the largest and most desirable waterfront holdings in the Lido/Longboat area. With a premier western exposure and sweeping waterfront frontage, the property offers unobstructed, panoramic views of Sarasota’s legendary sunsets and the Gulf of Mexico's ever-changing beauty. Architectural brilliance is evident in every aspect of the estate’s design, as classic Mediterranean influences blend with graceful elegance. Security and exclusivity are paramount, ensuring that every moment in this sanctuary is one of tranquility and distinction. A regal, gated entrance creates a dramatic sense of arrival, while the privileged location ensures seclusion and prominence along spectacular waterways and pristine Gulf Coast shorelines. The long driveway winds through mature, manicured landscaping—lush with live oaks, sabal palms, palmettos, and ferns, all illuminated by dramatic night lighting. The home’s brick-paved courtyard presentation is adorned with stately columns and intricate detailing, setting a tone of timeless sophistication that echoes throughout the property. A stately portico welcomes with a monumental carved-wood entry door that sets the tone for sophisticated interiors. Inside, grand rooms feature exquisite fixtures, polished finishes, and rich furnishings, unified by an elegantly styled aesthetic and an atmosphere of refined opulence. Every detail reflects a commitment to luxury, comfort, and timeless style. Stunning examples include exquisite marble and wood flooring, a sweeping curved staircase with iron railing, arched windows and doors, artisan millwork, high ceilings with custom details, triple crown molding, and bespoke cabinetry that embellish the home throughout. With three expansive levels, the residence boasts four en suite bedrooms, an attached 770-square-foot VIP apartment secluded from the rest of the house, two additional baths, dual living rooms, three formal and casual dining areas, three offices, a vast recreation room, a gym, two laundry rooms, an elevator, two fireplaces, a three-car garage, and dozens of French doors and glass sliders that open to invite the incredible outdoors in. Expansive covered terraces and upper-level balconies stretch along the rear façade, offering multiple spaces for outdoor living and entertaining—perfect for both lavish celebrations and intimate gatherings. Outdoor living unfolds effortlessly with a sleek pool and spa, inviting lounges, open-air dining areas, and voluminous acreage that add to the options and appeal of waterfront living. Every aspect of the residence, from its expansive footprint to its gilded amenities, has been thoughtfully designed to deliver a lifestyle of unrivaled sophistication, comfort, and exclusivity. This coastal refuge offers an irreplaceable opportunity in Sarasota’s elite waterfront market. The estate’s enviable location offers easy access to Sarasota’s world-class beaches, the downtown’s vibrant cultural scene, and the boutique shopping and fine dining venues of St. Armands Circle. This exceptional listing is truly stunning, perfect for a luxurious lifestyle in a magnificent setting. A must-see in person to fully appreciate its wonderful allure and unique characteristics.

1083 Westway Drive, Sarasota

$5,900,000

An extraordinary opportunity awaits to create a world-class waterfront estate along one of Sarasota's most coveted stretches of Gulf coastline. Perfectly positioned within the exclusive Lido Shores community, this cleared and construction-ready homesite presents a rare opportunity to design and build a custom coastal masterpiece in one of Florida's most sought after barrier island enclaves. Spanning nearly 12,000 square feet with an impressive 143 feet of direct Gulf frontage, the property captures breathtaking panoramic water views, unforgettable sunsets, and the tranquil Gulf beauty from one of the area's most sought-after locations. With private neighborhood beach access and an exceptional waterfront setting, this remarkable homesite offers the ideal foundation for a residence that reflects your unique vision and lifestyle. Thoughtfully prepared for development, the quarter-acre parcel features a striking stone-faced perimeter wall with a gated entry for privacy, professionally designed landscaping that creates an elegant first impression, and an approved seawall permit to further enhance the property's long-term value and functionality. Imagine a residence defined by soaring walls of glass framing endless Gulf views, expansive indoor and outdoor living spaces designed for effortless entertaining, a spectacular chef's kitchen, private wellness amenities, a resort-inspired pool and spa, and every luxury imaginable. Select the builder of your choice and collaborate on a home tailored to your exact specifications—where architectural excellence and coastal elegance become one. Opportunities to acquire a Gulf-front homesite of this caliber are exceedingly rare. More than simply vacant land, this is an invitation to create a timeless legacy estate on one of Sarasota's most distinguished addresses—where exceptional design, uncompromising luxury, and the incomparable beauty of the sand, sea, and sky come together to create something truly extraordinary.

Lido Shores SubDv. ⋅ 34236 Zip Code

An extraordinary opportunity awaits to create a world-class waterfront estate along one of Sarasota's most coveted stretches of Gulf coastline. Perfectly positioned within the exclusive Lido Shores community, this cleared and construction-ready homesite presents a rare opportunity to design and build a custom coastal masterpiece in one of Florida's most sought after barrier island enclaves. Spanning nearly 12,000 square feet with an impressive 143 feet of direct Gulf frontage, the property captures breathtaking panoramic water views, unforgettable sunsets, and the tranquil Gulf beauty from one of the area's most sought-after locations. With private neighborhood beach access and an exceptional waterfront setting, this remarkable homesite offers the ideal foundation for a residence that reflects your unique vision and lifestyle. Thoughtfully prepared for development, the quarter-acre parcel features a striking stone-faced perimeter wall with a gated entry for privacy, professionally designed landscaping that creates an elegant first impression, and an approved seawall permit to further enhance the property's long-term value and functionality. Imagine a residence defined by soaring walls of glass framing endless Gulf views, expansive indoor and outdoor living spaces designed for effortless entertaining, a spectacular chef's kitchen, private wellness amenities, a resort-inspired pool and spa, and every luxury imaginable. Select the builder of your choice and collaborate on a home tailored to your exact specifications—where architectural excellence and coastal elegance become one. Opportunities to acquire a Gulf-front homesite of this caliber are exceedingly rare. More than simply vacant land, this is an invitation to create a timeless legacy estate on one of Sarasota's most distinguished addresses—where exceptional design, uncompromising luxury, and the incomparable beauty of the sand, sea, and sky come together to create something truly extraordinary.

1215 Westway Drive, Sarasota

$13,900,000

One of Sarasota's most extraordinary Gulf-front estates, this magnificent coastal sanctuary is gracefully positioned within the exclusive enclave of Lido Shores, representing the pinnacle of luxury, architectural distinction, and timeless elegance. Framed by a majestic backdrop of endless Gulf waters and breathtaking sunsets, the residence commands one of the area's most coveted stretches of coastline, where panoramic views and unparalleled privacy create an unforgettable setting. Designed by celebrated architect Clifford M. Scholz, this exceptional 6,862-square-foot masterpiece is a striking expression of modern sophistication, seamlessly blending architectural artistry with refined coastal living. Spectacular interiors unfold beneath soaring ceilings accented by dramatic designer lighting, while walls of floor-to-ceiling glass dissolve the boundaries between indoors and the stunning waterfront beyond. Formal living and dining rooms are complemented by inviting gathering spaces, a sun-filled breakfast nook, and a versatile bonus room designed to accommodate both intimate family living and grand-scale entertaining. At the heart of the home, the remarkable chef's kitchen delivers an exceptional culinary experience, anchored by a magnificent La Cornue range with a matching commercial-grade vent hood. Top-tier appliances, a generous butler's pantry, climate-controlled wine storage, and a beautifully appointed built-in bar create an environment equally suited for lavish entertaining or relaxed evenings with family and friends. Five luxurious bedrooms, six full baths, and two powder rooms provide exceptional accommodations, including two private guest suites enhanced by charming loft spaces. The secluded owner's retreat was thoughtfully designed to evoke comfort and tranquility, while two executive offices provide refined spaces for work or study. Elevating everyday living even further are a traditional sauna and a state-of-the-art infrared light therapy room, offering a private wellness experience worthy of a world-class spa. Throughout the residence, exquisite craftsmanship is evident in every detail, from the one-of-a-kind custom staircase to two elegant fireplaces that enrich the home's warmth and architectural character. Outdoors, an extensive waterfront terrace embraces the Gulf with effortless elegance. A heated resort-style pool with a cascading waterfall serves as the centerpiece of the lush tropical landscape, creating a spectacular setting for entertaining or quiet relaxation while surrounded by sweeping coastal vistas. Arriving through grand entry gates, the estate immediately conveys a sense of prestige and seclusion. A striking Turkish shell stone perimeter wall provides exceptional privacy, while the expansive grounds present a rare opportunity to further enhance the property by creating an extraordinary multigenerational family compound or additional guest accommodations. Thoughtfully elevated for superior storm resilience, the residence combines enduring construction with uncompromising luxury. Located just minutes from the boutiques and fine dining of St. Armands Circle and the vibrant arts, culture, and waterfront attractions of downtown Sarasota, this remarkable property is far more than an exceptional residence—it is a legacy estate destined to remain one of Lido Key's most iconic and distinguished Gulf-front homes for generations to come. The adjacent parcel at 1215 Westway is also available for purchase.

6 Beds ⋅ 7 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code

One of Sarasota's most extraordinary Gulf-front estates, this magnificent coastal sanctuary is gracefully positioned within the exclusive enclave of Lido Shores, representing the pinnacle of luxury, architectural distinction, and timeless elegance. Framed by a majestic backdrop of endless Gulf waters and breathtaking sunsets, the residence commands one of the area's most coveted stretches of coastline, where panoramic views and unparalleled privacy create an unforgettable setting. Designed by celebrated architect Clifford M. Scholz, this exceptional 6,862-square-foot masterpiece is a striking expression of modern sophistication, seamlessly blending architectural artistry with refined coastal living. Spectacular interiors unfold beneath soaring ceilings accented by dramatic designer lighting, while walls of floor-to-ceiling glass dissolve the boundaries between indoors and the stunning waterfront beyond. Formal living and dining rooms are complemented by inviting gathering spaces, a sun-filled breakfast nook, and a versatile bonus room designed to accommodate both intimate family living and grand-scale entertaining. At the heart of the home, the remarkable chef's kitchen delivers an exceptional culinary experience, anchored by a magnificent La Cornue range with a matching commercial-grade vent hood. Top-tier appliances, a generous butler's pantry, climate-controlled wine storage, and a beautifully appointed built-in bar create an environment equally suited for lavish entertaining or relaxed evenings with family and friends. Five luxurious bedrooms, six full baths, and two powder rooms provide exceptional accommodations, including two private guest suites enhanced by charming loft spaces. The secluded owner's retreat was thoughtfully designed to evoke comfort and tranquility, while two executive offices provide refined spaces for work or study. Elevating everyday living even further are a traditional sauna and a state-of-the-art infrared light therapy room, offering a private wellness experience worthy of a world-class spa. Throughout the residence, exquisite craftsmanship is evident in every detail, from the one-of-a-kind custom staircase to two elegant fireplaces that enrich the home's warmth and architectural character. Outdoors, an extensive waterfront terrace embraces the Gulf with effortless elegance. A heated resort-style pool with a cascading waterfall serves as the centerpiece of the lush tropical landscape, creating a spectacular setting for entertaining or quiet relaxation while surrounded by sweeping coastal vistas. Arriving through grand entry gates, the estate immediately conveys a sense of prestige and seclusion. A striking Turkish shell stone perimeter wall provides exceptional privacy, while the expansive grounds present a rare opportunity to further enhance the property by creating an extraordinary multigenerational family compound or additional guest accommodations. Thoughtfully elevated for superior storm resilience, the residence combines enduring construction with uncompromising luxury. Located just minutes from the boutiques and fine dining of St. Armands Circle and the vibrant arts, culture, and waterfront attractions of downtown Sarasota, this remarkable property is far more than an exceptional residence—it is a legacy estate destined to remain one of Lido Key's most iconic and distinguished Gulf-front homes for generations to come. The adjacent parcel at 1215 Westway is also available for purchase.

1209 Westway Drive, Sarasota

$6,995,000

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.

4 Beds ⋅ 6 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code

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.

246 Morningside Drive, Sarasota

$11,900,000

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.

5 Beds ⋅ 8 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code

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.

1435 Westway Drive, Sarasota

$6,100,000

A rare and remarkable opportunity within the exclusive Lido Shores neighborhood — this exceptional .69-acre Gulf-facing parcel (with direct access to Lido Beach) offers the ideal canvas to create a custom coastal retreat in one of Sarasota’s most coveted locations. 1003 Westway Drive is perfectly positioned at the end of a quiet street and bordered by a nature preserve on one sidet. The setting delivers an unrivled sense of privacy while offering access to Pansy Bayou. You'll enjoy the potential for Gulf of Mexico, Sarasota Bay, and downtown skyline views from a thoughtfully designed residence. Imagine evenings defined by spectacular sunsets and a lifestyle centered around water, nature and refined coastal living. Residents of Lido Shores enjoy private beach access, placing the Gulf’s renowned shoreline just moments away. From this location, a short stroll leads to the vibrant shopping, dining, and cultural experiences of St. Armands Circle — blending exclusivity with convenience in a way few addresses can match. For those seeking an even grander vision, the adjacent parcel presents the opportunity to assemble a truly sublime estate - or even a guest house or sport pavillion - just steps from the Gulf. Craft your upscale Florida lifestyle from the ground up in a setting defined by beauty, rarity, and possibility.

Lido Shores SubDv. ⋅ 34236 Zip Code

A rare and remarkable opportunity within the exclusive Lido Shores neighborhood — this exceptional .69-acre Gulf-facing parcel (with direct access to Lido Beach) offers the ideal canvas to create a custom coastal retreat in one of Sarasota’s most coveted locations. 1003 Westway Drive is perfectly positioned at the end of a quiet street and bordered by a nature preserve on one sidet. The setting delivers an unrivled sense of privacy while offering access to Pansy Bayou. You'll enjoy the potential for Gulf of Mexico, Sarasota Bay, and downtown skyline views from a thoughtfully designed residence. Imagine evenings defined by spectacular sunsets and a lifestyle centered around water, nature and refined coastal living. Residents of Lido Shores enjoy private beach access, placing the Gulf’s renowned shoreline just moments away. From this location, a short stroll leads to the vibrant shopping, dining, and cultural experiences of St. Armands Circle — blending exclusivity with convenience in a way few addresses can match. For those seeking an even grander vision, the adjacent parcel presents the opportunity to assemble a truly sublime estate - or even a guest house or sport pavillion - just steps from the Gulf. Craft your upscale Florida lifestyle from the ground up in a setting defined by beauty, rarity, and possibility.

1003 Westway Drive, Sarasota

$3,600,000

A rare and remarkable opportunity within the exclusive Lido Shores neighborhood — this exceptional .87-acre parcel at 1051 Westway Drive offers the ideal canvas to create a custom coastal estate in one of Sarasota’s most coveted locations. Perfectly positioned at the end of a quiet street and bordered by a nature preserve on one side, the setting delivers an unrivled sense of privacy while offering access to Pansy Bayou. You'll enjoy the potential for Gulf of Mexico, Sarasota Bay, and downtown skyline views from a thoughtfully designed residence. Imagine evenings defined by spectacular sunsets and a lifestyle centered around water, nature and refined coastal living. Residents of Lido Shores enjoy private beach access, placing the Gulf’s renowned shoreline just moments away. From this location, a short stroll leads to the vibrant shopping, dining, and cultural experiences of St. Armands Circle — blending exclusivity with convenience in a way few addresses can match. For those seeking an even grander vision, the adjacent parcel presents the opportunity to assemble a truly sublime estate - or even a guest house or sport pavillion - just steps from the Gulf. Craft your upscale Florida lifestyle from the ground up in a setting defined by beauty, rarity, and possibility.

Lido Shores SubDv. ⋅ 34236 Zip Code

A rare and remarkable opportunity within the exclusive Lido Shores neighborhood — this exceptional .87-acre parcel at 1051 Westway Drive offers the ideal canvas to create a custom coastal estate in one of Sarasota’s most coveted locations. Perfectly positioned at the end of a quiet street and bordered by a nature preserve on one side, the setting delivers an unrivled sense of privacy while offering access to Pansy Bayou. You'll enjoy the potential for Gulf of Mexico, Sarasota Bay, and downtown skyline views from a thoughtfully designed residence. Imagine evenings defined by spectacular sunsets and a lifestyle centered around water, nature and refined coastal living. Residents of Lido Shores enjoy private beach access, placing the Gulf’s renowned shoreline just moments away. From this location, a short stroll leads to the vibrant shopping, dining, and cultural experiences of St. Armands Circle — blending exclusivity with convenience in a way few addresses can match. For those seeking an even grander vision, the adjacent parcel presents the opportunity to assemble a truly sublime estate - or even a guest house or sport pavillion - just steps from the Gulf. Craft your upscale Florida lifestyle from the ground up in a setting defined by beauty, rarity, and possibility.

1051 Westway Drive, Sarasota

$6,999,000

Gulf-Front Opportunity in Lido Shores — 127 Feet on the Open Water! A rare offering in Sarasota’s coveted Lido Shores, this Gulf-front property presents an exceptional opportunity to build a signature coastal estate on one of the region’s most desirable stretches of shoreline. Positioned on nearly half an acre (0.41 acres) with 127 feet of direct frontage on the Gulf of Mexico, this homesite is perfectly placed at the dynamic junction of New Pass, where turquoise waters meet the open Gulf—an unmatched setting for boating enthusiasts, beach lovers, and architectural visionaries. With sweeping full Gulf-to-bay views, the property’s orientation captures dramatic sunsets and ever-changing waterfront scenery. Deep-water access and immediate proximity to the channel create effortless passage for boating, sailing, kayaking, or fishing. A concrete seawall is already in place, providing a strong foundation for future waterfront design and dock possibilities. Set among some of Sarasota’s most notable modern and luxury residences, this lot sits within the prestigious Lido Shores—an enclave known for its privacy, walkability, and architectural pedigree. Owners have the option to join the Lido Shores Association, which offers access to a private, gated beach park just moments from the property, complete with Gulf access, picnic zones, and a secluded stretch of sand exclusive to community members. With 97 feet of frontage on Westway Drive, a generous building envelope, and its privileged water position, the site allows for a substantial custom residence, pool, outdoor living areas, and multi-car garage. Whether envisioned as a modernist showpiece or timeless coastal retreat, the location elevates every possibility. Lido Shores offers the ideal blend of tranquility and access. A short stroll brings you to North Lido Beach—one of Sarasota’s most natural and peaceful shorelines. Just over the bridge is St. Armands Circle, home to luxury boutiques, fine dining, and year-round entertainment. Nearby New Pass Grill & Bait Shop, Mote Marine Laboratory & Aquarium, Sarasota Sailing Squadron, and Ken Thompson Park highlight the area’s coastal charm and outdoor experiences. A quick drive connects you to the cultural heartbeat of downtown Sarasota, including the Van Wezel Performing Arts Hall, Marie Selby Botanical Gardens, the Ringling Museum, theaters, galleries, and the city’s bayfront promenade. Marinas, world-class golf and tennis clubs, and resort amenities further enhance the unparalleled lifestyle available at this address. With its magnitude, water frontage, and premier location, 1199 Westway Drive stands as one of the most compelling Gulf-front building opportunities in Southwest Florida—a place where your future dream home can rise above the waves and capture Sarasota’s most extraordinary vistas.

Lido Shores SubDv. ⋅ 34236 Zip Code

Gulf-Front Opportunity in Lido Shores — 127 Feet on the Open Water! A rare offering in Sarasota’s coveted Lido Shores, this Gulf-front property presents an exceptional opportunity to build a signature coastal estate on one of the region’s most desirable stretches of shoreline. Positioned on nearly half an acre (0.41 acres) with 127 feet of direct frontage on the Gulf of Mexico, this homesite is perfectly placed at the dynamic junction of New Pass, where turquoise waters meet the open Gulf—an unmatched setting for boating enthusiasts, beach lovers, and architectural visionaries. With sweeping full Gulf-to-bay views, the property’s orientation captures dramatic sunsets and ever-changing waterfront scenery. Deep-water access and immediate proximity to the channel create effortless passage for boating, sailing, kayaking, or fishing. A concrete seawall is already in place, providing a strong foundation for future waterfront design and dock possibilities. Set among some of Sarasota’s most notable modern and luxury residences, this lot sits within the prestigious Lido Shores—an enclave known for its privacy, walkability, and architectural pedigree. Owners have the option to join the Lido Shores Association, which offers access to a private, gated beach park just moments from the property, complete with Gulf access, picnic zones, and a secluded stretch of sand exclusive to community members. With 97 feet of frontage on Westway Drive, a generous building envelope, and its privileged water position, the site allows for a substantial custom residence, pool, outdoor living areas, and multi-car garage. Whether envisioned as a modernist showpiece or timeless coastal retreat, the location elevates every possibility. Lido Shores offers the ideal blend of tranquility and access. A short stroll brings you to North Lido Beach—one of Sarasota’s most natural and peaceful shorelines. Just over the bridge is St. Armands Circle, home to luxury boutiques, fine dining, and year-round entertainment. Nearby New Pass Grill & Bait Shop, Mote Marine Laboratory & Aquarium, Sarasota Sailing Squadron, and Ken Thompson Park highlight the area’s coastal charm and outdoor experiences. A quick drive connects you to the cultural heartbeat of downtown Sarasota, including the Van Wezel Performing Arts Hall, Marie Selby Botanical Gardens, the Ringling Museum, theaters, galleries, and the city’s bayfront promenade. Marinas, world-class golf and tennis clubs, and resort amenities further enhance the unparalleled lifestyle available at this address. With its magnitude, water frontage, and premier location, 1199 Westway Drive stands as one of the most compelling Gulf-front building opportunities in Southwest Florida—a place where your future dream home can rise above the waves and capture Sarasota’s most extraordinary vistas.

1199 Westway Drive, Sarasota

$4,925,000

Experience the epitome of island living in this luxurious three-bedroom, four-bath residence. With high-end finishes and spacious rooms featuring soaring ceilings, every detail exudes comfort and elegance. Enjoy leisure time with a ping-pong table, a theater room, and a pristine pool that basks in southern exposure, overlooking the tranquil open bayou. The kitchen, complete with a breakfast area, offers stunning views of the pool and bayou, while a cozy office space provides an ideal work-from-home environment. The home also features a beautiful dining room with a wet bar and a welcoming living room adorned with elegant wood floors throughout. Each bedroom offers luxurious en-suite baths, and the master bath is a true retreat. The expansive pool deck area and the convenience of a two-car garage and boat dock add to the home’s charm. Plus, with an elevator and a full-house generator, you’ll enjoy ultimate comfort and peace of mind.

3 Beds ⋅ 4 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code

Experience the epitome of island living in this luxurious three-bedroom, four-bath residence. With high-end finishes and spacious rooms featuring soaring ceilings, every detail exudes comfort and elegance. Enjoy leisure time with a ping-pong table, a theater room, and a pristine pool that basks in southern exposure, overlooking the tranquil open bayou. The kitchen, complete with a breakfast area, offers stunning views of the pool and bayou, while a cozy office space provides an ideal work-from-home environment. The home also features a beautiful dining room with a wet bar and a welcoming living room adorned with elegant wood floors throughout. Each bedroom offers luxurious en-suite baths, and the master bath is a true retreat. The expansive pool deck area and the convenience of a two-car garage and boat dock add to the home’s charm. Plus, with an elevator and a full-house generator, you’ll enjoy ultimate comfort and peace of mind.

340 Morningside Drive, Sarasota