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$2,299,000

Historic Gillespie Park Home | Luxury Downtown Sarasota Living on Three Lots! Discover a rare opportunity to own a beautifully restored historic home in Gillespie Park, one of Downtown Sarasota's most desirable historic neighborhoods. Originally built during Florida's celebrated Land Boom of the 1920s, this exceptional residence has been thoughtfully expanded and extensively renovated, preserving its timeless architectural character while seamlessly incorporating the modern amenities today's luxury buyers expect. Occupying 3 lots, this remarkable property offers an extraordinary combination of privacy, mature landscaping, and expansive outdoor living spaces just moments from Downtown Sarasota, The Bay Park, the Rosemary District, Sarasota Bay, Marina Jack, boutique shopping, acclaimed restaurants, theaters, galleries, and the city's vibrant cultural scene. Whether you're searching for a luxury primary residence or a distinctive historic Sarasota home, this property delivers an unmatched downtown lifestyle. A substantial two-story addition completed in 2019 expanded the home by approximately 800 square feet, creating a floor plan designed for modern living while remaining true to the home's original architecture. The addition enlarged the chef's kitchen and added a full bathroom, pantry, utility room, and reading room on the main level. Upstairs, the primary suite was transformed into a luxurious retreat with a spa-inspired bathroom and dual walk-in closets. At the heart of the home is a beautifully renovated chef's kitchen featuring premium Thermador appliances, including three ovens, a six-burner gas cooktop, custom cabinetry, granite countertops, and a charming bay window overlooking the professionally landscaped gardens. Rich hardwood flooring, renovated bathrooms, fresh interior paint, generous bedrooms, and preserved architectural details create the perfect balance between historic elegance and contemporary comfort. Extensively updated for comfort, efficiency, and peace of mind, the residence features custom hurricane-impact windows installed in 2024 and designed to replicate the home's original windows while providing modern storm protection, energy efficiency, and enhanced sound insulation. Additional improvements include a new roof (2022), an expansive screened lanai completed in 2022 and enhanced with an upgraded drainage system in 2025, a new driveway, gutters, underground drainage, professionally installed irrigation, and two air-conditioning systems. Professionally designed Florida-native landscaping, winding brick pathways, tranquil gardens, and a newly established butterfly garden create a peaceful retreat rarely found this close to the heart of Sarasota. Offering the rare combination of a fully renovated historic Sarasota home, three separately platted lots, luxury finishes, modern infrastructure, and an exceptional Downtown Sarasota location, this one-of-a-kind residence is ideally positioned near The Bay Park, Sarasota Bay, the Rosemary District, Marina Jack, the Sarasota Farmers Market, Selby Botanical Gardens, the Sarasota Opera House, boutique shopping, award-winning dining, and the area's world-renowned Gulf beaches. Rich in history yet thoughtfully designed for today's lifestyle, this extraordinary home presents a rare opportunity to experience the very best of Downtown Sarasota luxury living.

4 Beds ⋅ 4 Baths ⋅ Inwood Park SubDv. ⋅ 34236 Zip Code

Historic Gillespie Park Home | Luxury Downtown Sarasota Living on Three Lots! Discover a rare opportunity to own a beautifully restored historic home in Gillespie Park, one of Downtown Sarasota's most desirable historic neighborhoods. Originally built during Florida's celebrated Land Boom of the 1920s, this exceptional residence has been thoughtfully expanded and extensively renovated, preserving its timeless architectural character while seamlessly incorporating the modern amenities today's luxury buyers expect. Occupying 3 lots, this remarkable property offers an extraordinary combination of privacy, mature landscaping, and expansive outdoor living spaces just moments from Downtown Sarasota, The Bay Park, the Rosemary District, Sarasota Bay, Marina Jack, boutique shopping, acclaimed restaurants, theaters, galleries, and the city's vibrant cultural scene. Whether you're searching for a luxury primary residence or a distinctive historic Sarasota home, this property delivers an unmatched downtown lifestyle. A substantial two-story addition completed in 2019 expanded the home by approximately 800 square feet, creating a floor plan designed for modern living while remaining true to the home's original architecture. The addition enlarged the chef's kitchen and added a full bathroom, pantry, utility room, and reading room on the main level. Upstairs, the primary suite was transformed into a luxurious retreat with a spa-inspired bathroom and dual walk-in closets. At the heart of the home is a beautifully renovated chef's kitchen featuring premium Thermador appliances, including three ovens, a six-burner gas cooktop, custom cabinetry, granite countertops, and a charming bay window overlooking the professionally landscaped gardens. Rich hardwood flooring, renovated bathrooms, fresh interior paint, generous bedrooms, and preserved architectural details create the perfect balance between historic elegance and contemporary comfort. Extensively updated for comfort, efficiency, and peace of mind, the residence features custom hurricane-impact windows installed in 2024 and designed to replicate the home's original windows while providing modern storm protection, energy efficiency, and enhanced sound insulation. Additional improvements include a new roof (2022), an expansive screened lanai completed in 2022 and enhanced with an upgraded drainage system in 2025, a new driveway, gutters, underground drainage, professionally installed irrigation, and two air-conditioning systems. Professionally designed Florida-native landscaping, winding brick pathways, tranquil gardens, and a newly established butterfly garden create a peaceful retreat rarely found this close to the heart of Sarasota. Offering the rare combination of a fully renovated historic Sarasota home, three separately platted lots, luxury finishes, modern infrastructure, and an exceptional Downtown Sarasota location, this one-of-a-kind residence is ideally positioned near The Bay Park, Sarasota Bay, the Rosemary District, Marina Jack, the Sarasota Farmers Market, Selby Botanical Gardens, the Sarasota Opera House, boutique shopping, award-winning dining, and the area's world-renowned Gulf beaches. Rich in history yet thoughtfully designed for today's lifestyle, this extraordinary home presents a rare opportunity to experience the very best of Downtown Sarasota luxury living.

1874 6th Street, Sarasota

$1,450,000

FULLY FURNISHED SHORT TERM RENTAL PROPERTY. Experience the best of "West of Trail" living in this impeccably maintained, renovated pool home situated on an OVERSIZED LOT. The interior features include refinished HARDWOOD FLOORS, double-paned windows, and an UPDATED KITCHEN equipped with custom cabinetry, granite countertops, and stainless-steel appliances. The inviting main living area is highlighted by a tray ceiling, gas fireplace and French doors leading to a private outdoor area and SALTWATER POOL, perfect for the Florida lifestyle. The fully FENCED professionally landscaped yard includes a PUTTING GREEN. Significant improvements offer peace of mind and long-term value, including a new standing seam METAL ROOF (2025), NEWER A/C system (2022)/mini-split (2024), and completely REPLUMBED with PVC. The air-conditioned TWO-CAR GARAGE features new epoxy flooring and is currently utilized as a versatile game room. Ideally located in the sought-after Southside Elementary district, this residence provides quick access to Southside Village, downtown Sarasota, and the renowned beaches of Siesta and Lido Key. This property has a great rental history (over $83,000 in the first year) along with $27,000+ in future bookings, please inquire for more details

3 Beds ⋅ 2 Baths ⋅ Hudson Bayou SubDv. ⋅ 34236 Zip Code

FULLY FURNISHED SHORT TERM RENTAL PROPERTY. Experience the best of "West of Trail" living in this impeccably maintained, renovated pool home situated on an OVERSIZED LOT. The interior features include refinished HARDWOOD FLOORS, double-paned windows, and an UPDATED KITCHEN equipped with custom cabinetry, granite countertops, and stainless-steel appliances. The inviting main living area is highlighted by a tray ceiling, gas fireplace and French doors leading to a private outdoor area and SALTWATER POOL, perfect for the Florida lifestyle. The fully FENCED professionally landscaped yard includes a PUTTING GREEN. Significant improvements offer peace of mind and long-term value, including a new standing seam METAL ROOF (2025), NEWER A/C system (2022)/mini-split (2024), and completely REPLUMBED with PVC. The air-conditioned TWO-CAR GARAGE features new epoxy flooring and is currently utilized as a versatile game room. Ideally located in the sought-after Southside Elementary district, this residence provides quick access to Southside Village, downtown Sarasota, and the renowned beaches of Siesta and Lido Key. This property has a great rental history (over $83,000 in the first year) along with $27,000+ in future bookings, please inquire for more details

1931 High Point Circle, Sarasota

$1,350,000

Live grounded. Create freely. Canvas RADD introduces a single-level, 3-bedroom, 3-bath live/work residence set at street level in Sarasota’s Rosemary Arts and Design District, designed for flexibility, presence, and creative flow in one of the city’s most dynamic neighborhoods. The layout unfolds across one generous level with high ceilings and expansive windows that bring in natural light and neighborhood energy, supporting a live/work configuration ideal for studios, offices, client-facing spaces, or simply room to spread out. A private landscaped yard and courtyard extend the home outdoors, offering a rare urban luxury for morning routines, informal meetings, pets, and evenings under the lights while remaining connected to the city. The architecture is sharp and purposeful, defined by clean lines, modern materials, and interiors that feel collected rather than conventional, complemented by the convenience of a private garage and effortless ground-floor access. Residents also enjoy access to curated shared amenities including a fitness studio for daily resets and a conference room for focused work, collaboration, or creative sessions without leaving the block. From the front door, Sarasota opens up quickly with walkable access to neighborhood favorites like Project Coffee, Shack Yoga, the Sarasota Farmers Market, and local dining and shopping throughout the Rosemary District, along with seamless access to the arts and culture of Downtown Sarasota including live performances, concerts, galleries, and theaters, plus easy drives to St. Armands Circle and nearby Gulf beaches.

3 Beds ⋅ 2 Baths ⋅ Vista Urbana SubDv. ⋅ 34236 Zip Code

Live grounded. Create freely. Canvas RADD introduces a single-level, 3-bedroom, 3-bath live/work residence set at street level in Sarasota’s Rosemary Arts and Design District, designed for flexibility, presence, and creative flow in one of the city’s most dynamic neighborhoods. The layout unfolds across one generous level with high ceilings and expansive windows that bring in natural light and neighborhood energy, supporting a live/work configuration ideal for studios, offices, client-facing spaces, or simply room to spread out. A private landscaped yard and courtyard extend the home outdoors, offering a rare urban luxury for morning routines, informal meetings, pets, and evenings under the lights while remaining connected to the city. The architecture is sharp and purposeful, defined by clean lines, modern materials, and interiors that feel collected rather than conventional, complemented by the convenience of a private garage and effortless ground-floor access. Residents also enjoy access to curated shared amenities including a fitness studio for daily resets and a conference room for focused work, collaboration, or creative sessions without leaving the block. From the front door, Sarasota opens up quickly with walkable access to neighborhood favorites like Project Coffee, Shack Yoga, the Sarasota Farmers Market, and local dining and shopping throughout the Rosemary District, along with seamless access to the arts and culture of Downtown Sarasota including live performances, concerts, galleries, and theaters, plus easy drives to St. Armands Circle and nearby Gulf beaches.

1343 4th Street Unit 102, Sarasota