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An exceptional opportunity to own a rare waterfront homesite in Cherokee Park, one of Sarasota’s most established neighborhoods. Encompassing an expansive 20,215 square feet, this remarkable property offers the perfect canvas to create a custom estate tailored to your vision. Surrounded by magnificent residences, mature trees, and lush tropical landscaping, this nearly half-acre parcel provides a beautiful setting for an extraordinary home. With tranquil canal views and generous space for expansive indoor-outdoor living, a resort-style pool, lush gardens, and elegant entertaining areas, the possibilities are truly exceptional. Cherokee Park is celebrated for its timeless character, beautiful tree-lined streets, and prime location west of the Trail. Enjoy convenient access to Southside Village, downtown Sarasota, fine dining, boutique shopping, Sarasota Memorial Hospital, and the world-renowned beaches of Siesta Key. Whether envisioning a contemporary residence or a timeless coastal estate, this exceptional property presents a rare opportunity to build in one of Sarasota’s most sought-after neighborhoods. Secure your place in Cherokee Park and bring your architectural vision to life.

Cherokee Park SubDv. ⋅ 34239 Zip Code

An exceptional opportunity to own a rare waterfront homesite in Cherokee Park, one of Sarasota’s most established neighborhoods. Encompassing an expansive 20,215 square feet, this remarkable property offers the perfect canvas to create a custom estate tailored to your vision. Surrounded by magnificent residences, mature trees, and lush tropical landscaping, this nearly half-acre parcel provides a beautiful setting for an extraordinary home. With tranquil canal views and generous space for expansive indoor-outdoor living, a resort-style pool, lush gardens, and elegant entertaining areas, the possibilities are truly exceptional. Cherokee Park is celebrated for its timeless character, beautiful tree-lined streets, and prime location west of the Trail. Enjoy convenient access to Southside Village, downtown Sarasota, fine dining, boutique shopping, Sarasota Memorial Hospital, and the world-renowned beaches of Siesta Key. Whether envisioning a contemporary residence or a timeless coastal estate, this exceptional property presents a rare opportunity to build in one of Sarasota’s most sought-after neighborhoods. Secure your place in Cherokee Park and bring your architectural vision to life.

1620 N Lodge Drive, Sarasota

$2,450,000

Rarely available in Cherokee Park, widely regarded as one of Sarasota’s most desirable West of Trail neighborhoods, 1722 North Drive presents an extraordinary opportunity on a remarkably oversized 150-by-150-foot homesite with an impressive 150 feet of street frontage. Significantly larger and more generously proportioned than many properties in the neighborhood, the square parcel offers the scale, symmetry, and flexibility increasingly difficult to find in Sarasota’s most established luxury enclaves. Cherokee Park is distinguished by its quiet, tree-lined streets and an architectural landscape where beautifully restored historic residences sit alongside prominent new custom homes designed and built by some of Sarasota’s most respected architects and builders. Within that setting, this property stands apart. Mature, century-old oak trees frame the perimeter, creating a park-like canopy of privacy, shade, and character while leaving the heart of the lot remarkably open. The combination of its ideal square configuration, substantial street presence, and undisturbed tree canopy creates a compelling canvas for a future luxury residence, with room to build a custom home, pool, outdoor living areas, and landscaped grounds without overwhelming the site. The existing home is charming, comfortable, and move-in ready, giving its next owner the flexibility to enjoy the property immediately, renovate over time, or hold it while designing a future custom residence. Recent improvements include a new air-conditioning system, hot water heater, sewer line, and resurfaced pool, all completed in 2024. A separate bonus space offers an ideal setting for a work-from-home office, art studio, gym, or creative retreat. Located just moments from Southside Elementary School and close to Southside Village, downtown Sarasota, the bayfront, and Sarasota Memorial Hospital, 1722 North Drive combines one of the city’s most coveted residential settings with the dimensions and character of a truly distinctive homesite. Whether enjoyed as it stands today or reimagined as a significant new estate, this is a rare opportunity to secure an unusually substantial parcel and lasting value in the heart of Cherokee Park.

3 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code

Rarely available in Cherokee Park, widely regarded as one of Sarasota’s most desirable West of Trail neighborhoods, 1722 North Drive presents an extraordinary opportunity on a remarkably oversized 150-by-150-foot homesite with an impressive 150 feet of street frontage. Significantly larger and more generously proportioned than many properties in the neighborhood, the square parcel offers the scale, symmetry, and flexibility increasingly difficult to find in Sarasota’s most established luxury enclaves. Cherokee Park is distinguished by its quiet, tree-lined streets and an architectural landscape where beautifully restored historic residences sit alongside prominent new custom homes designed and built by some of Sarasota’s most respected architects and builders. Within that setting, this property stands apart. Mature, century-old oak trees frame the perimeter, creating a park-like canopy of privacy, shade, and character while leaving the heart of the lot remarkably open. The combination of its ideal square configuration, substantial street presence, and undisturbed tree canopy creates a compelling canvas for a future luxury residence, with room to build a custom home, pool, outdoor living areas, and landscaped grounds without overwhelming the site. The existing home is charming, comfortable, and move-in ready, giving its next owner the flexibility to enjoy the property immediately, renovate over time, or hold it while designing a future custom residence. Recent improvements include a new air-conditioning system, hot water heater, sewer line, and resurfaced pool, all completed in 2024. A separate bonus space offers an ideal setting for a work-from-home office, art studio, gym, or creative retreat. Located just moments from Southside Elementary School and close to Southside Village, downtown Sarasota, the bayfront, and Sarasota Memorial Hospital, 1722 North Drive combines one of the city’s most coveted residential settings with the dimensions and character of a truly distinctive homesite. Whether enjoyed as it stands today or reimagined as a significant new estate, this is a rare opportunity to secure an unusually substantial parcel and lasting value in the heart of Cherokee Park.

1722 North Drive, Sarasota

$2,000,000

This exceptional 100X200 lot in historic Cherokee Park awaits your dream home, with Fergeson Brothers as the designated design and construction company; This west-of-the-trail neighborhood is located on Sarasota Bay in the City of Sarasota.

Cherokee Park SubDv. ⋅ 34239 Zip Code

This exceptional 100X200 lot in historic Cherokee Park awaits your dream home, with Fergeson Brothers as the designated design and construction company; This west-of-the-trail neighborhood is located on Sarasota Bay in the City of Sarasota.

1749 Cherokee Drive, Sarasota

$11,995,000

One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room with refined finishes and modern systems while preserving its timeless architectural character. Hidden away at the end of Southwest Drive within the coveted Cherokee Park neighborhood, this 5-bedroom home offers exceptional seclusion and privacy, surrounded by lush, verdant landscaping, specimen trees and mature oaks, with tranquil water views providing a serene backdrop throughout the entire home. A masterpiece by design, this architectural gem was designed by esteemed architect Clifford Scholtz and built with impeccable craftsmanship by Rich Perrone of Perrone Construction. Among the recent exterior improvements are a new roof and gutters, fresh exterior paint, new decorative landscape lighting, and a refreshed outdoor shower. Inside, thoughtfully curated modern finishes and updates seamlessly blend with classic architectural details such as columns, archways, and a mahogany-paneled office, creating interiors that feel bright, open, and timeless. New European white oak flooring flows through the main living areas, while Stark carpeting adds warmth to the staircase, select bedrooms, and the bonus room. A culinary enthusiast’s dream, the completely updated kitchen boasts Taj Mahal leathered stone countertops, White Haze dolomite backsplash, a micro cement hood, painted cabinetry, an oversized island, new sinks and faucets, a Sub-Zero fridge/freezer, and more. The charming breakfast area and adjacent family room, featuring a new micro cement fireplace with Taj Mahal hearth, are set against a backdrop of expansive windows and glass doors that capture picturesque bay views. A luxurious and peaceful retreat, the elaborate primary suite features a beautifully updated bath showcasing new vanities with Taj Mahal countertops and Brizo fixtures, plus new flooring, soaking tub, and walk-in shower. Secondary baths throughout the home have also been refreshed. Covered patios and loggias extend from the main living areas, creating ideal spaces for relaxation and enjoyment. Upstairs, the expansive gathering room impresses with its custom Perla Venata quartzite bar, freshly painted ceiling beams, large windows, and balcony access overlooking the bay, pool, and lush grounds. This is the perfect perch to enjoy large gatherings, relax at the bar, shoot pool, or have friends and family over on game day. Outside, the property unfolds as a private oasis, with a screened porch featuring Chicago brick pavers, a Wolf gas grill, Sub-Zero fridge, and refreshed finishes including a tiled backsplash, updated hardware, new sink and faucet, and refinished cabinetry. Chicago brick pavers also surround the free-form pool, creating a cohesive outdoor living environment. At the water’s edge, boaters will delight in the protected deep-water boat basin with two lifts (10,000-lb. and 16,000-lb. capacities), providing effortless maritime adventures. A detached oversized 3-car garage, connected by a covered walkway, provides ample space for storage or workshop use. Additional updates of note include updated HVAC systems, tankless water heaters, and modernized electrical throughout. A whole house generator rounds out the superlative systems. This exquisitely updated estate represents a rare offering where timeless elegance meets modern sophistication on one of Sarasota's most extraordinary waterfront settings.

5 Beds ⋅ 7 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code

One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room with refined finishes and modern systems while preserving its timeless architectural character. Hidden away at the end of Southwest Drive within the coveted Cherokee Park neighborhood, this 5-bedroom home offers exceptional seclusion and privacy, surrounded by lush, verdant landscaping, specimen trees and mature oaks, with tranquil water views providing a serene backdrop throughout the entire home. A masterpiece by design, this architectural gem was designed by esteemed architect Clifford Scholtz and built with impeccable craftsmanship by Rich Perrone of Perrone Construction. Among the recent exterior improvements are a new roof and gutters, fresh exterior paint, new decorative landscape lighting, and a refreshed outdoor shower. Inside, thoughtfully curated modern finishes and updates seamlessly blend with classic architectural details such as columns, archways, and a mahogany-paneled office, creating interiors that feel bright, open, and timeless. New European white oak flooring flows through the main living areas, while Stark carpeting adds warmth to the staircase, select bedrooms, and the bonus room. A culinary enthusiast’s dream, the completely updated kitchen boasts Taj Mahal leathered stone countertops, White Haze dolomite backsplash, a micro cement hood, painted cabinetry, an oversized island, new sinks and faucets, a Sub-Zero fridge/freezer, and more. The charming breakfast area and adjacent family room, featuring a new micro cement fireplace with Taj Mahal hearth, are set against a backdrop of expansive windows and glass doors that capture picturesque bay views. A luxurious and peaceful retreat, the elaborate primary suite features a beautifully updated bath showcasing new vanities with Taj Mahal countertops and Brizo fixtures, plus new flooring, soaking tub, and walk-in shower. Secondary baths throughout the home have also been refreshed. Covered patios and loggias extend from the main living areas, creating ideal spaces for relaxation and enjoyment. Upstairs, the expansive gathering room impresses with its custom Perla Venata quartzite bar, freshly painted ceiling beams, large windows, and balcony access overlooking the bay, pool, and lush grounds. This is the perfect perch to enjoy large gatherings, relax at the bar, shoot pool, or have friends and family over on game day. Outside, the property unfolds as a private oasis, with a screened porch featuring Chicago brick pavers, a Wolf gas grill, Sub-Zero fridge, and refreshed finishes including a tiled backsplash, updated hardware, new sink and faucet, and refinished cabinetry. Chicago brick pavers also surround the free-form pool, creating a cohesive outdoor living environment. At the water’s edge, boaters will delight in the protected deep-water boat basin with two lifts (10,000-lb. and 16,000-lb. capacities), providing effortless maritime adventures. A detached oversized 3-car garage, connected by a covered walkway, provides ample space for storage or workshop use. Additional updates of note include updated HVAC systems, tankless water heaters, and modernized electrical throughout. A whole house generator rounds out the superlative systems. This exquisitely updated estate represents a rare offering where timeless elegance meets modern sophistication on one of Sarasota's most extraordinary waterfront settings.

3000 Southwest Drive, Sarasota

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