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$249,000

Recent upgrades and meticulous maintenance at this pristine concrete block home in Cherokee Park, one of Holly Hill's most established and serene neighborhoods. Less than one mile to PICTONA, the area's only world class Pickleball facility, and only a short drive to the Halifax River and area beaches. The 1,384 sq ft of functional living space includes two bedrooms and two full bathrooms, each on their own wing of the home, making for two separate suites. The spacious kitchen is in the center of the home and includes a pantry, plenty of cabinet space, and newer stainless-steel appliances. Off the kitchen is a large dining area and living room with an entire wall of built-ins, over-looking the beautifully shaded backyard through the wall-to-wall sliding glass doors which allow plenty of natural light. The primary suite is massive with tons of closet space in the triple closets and has access to the backyard through a glass slider. Primary bathroom includes a large walk-in tiled shower and has access to the laundry room complete with utility sink, storage, shelving, and washer and dryer conveying. The second bedroom is on the other side of the home and could easily be its own guest suite with its own closet and bathroom with shower/tub combo. Plenty of storage throughout this home as well. The 2-car garage is off the laundry room with extra shelving already in place. Outside, you can enjoy the recently refreshed landscaping from the large concrete back patio, plenty of room in the back for a storage shed or pool! Indian Oaks is a quiet street with mature trees and no thru traffic. Grocers, Centennial Park, Pictona, Holly Hill Family YMCA, and Tanger Outlets are all nearby. Recent updates include a BRAND-NEW hot water heater (2026) and new mailbox. Roof 2011, HVAC 2017 (serviced yearly). Currently zoned for Holly Hill School, Ormond Beach Elementary, and Mainland High School. All information and room sizes in this listing are intended to be accurate but cannot be guaranteed. Buyers and their agents are always encouraged to perform due diligence.

2 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 32117 Zip Code

Recent upgrades and meticulous maintenance at this pristine concrete block home in Cherokee Park, one of Holly Hill's most established and serene neighborhoods. Less than one mile to PICTONA, the area's only world class Pickleball facility, and only a short drive to the Halifax River and area beaches. The 1,384 sq ft of functional living space includes two bedrooms and two full bathrooms, each on their own wing of the home, making for two separate suites. The spacious kitchen is in the center of the home and includes a pantry, plenty of cabinet space, and newer stainless-steel appliances. Off the kitchen is a large dining area and living room with an entire wall of built-ins, over-looking the beautifully shaded backyard through the wall-to-wall sliding glass doors which allow plenty of natural light. The primary suite is massive with tons of closet space in the triple closets and has access to the backyard through a glass slider. Primary bathroom includes a large walk-in tiled shower and has access to the laundry room complete with utility sink, storage, shelving, and washer and dryer conveying. The second bedroom is on the other side of the home and could easily be its own guest suite with its own closet and bathroom with shower/tub combo. Plenty of storage throughout this home as well. The 2-car garage is off the laundry room with extra shelving already in place. Outside, you can enjoy the recently refreshed landscaping from the large concrete back patio, plenty of room in the back for a storage shed or pool! Indian Oaks is a quiet street with mature trees and no thru traffic. Grocers, Centennial Park, Pictona, Holly Hill Family YMCA, and Tanger Outlets are all nearby. Recent updates include a BRAND-NEW hot water heater (2026) and new mailbox. Roof 2011, HVAC 2017 (serviced yearly). Currently zoned for Holly Hill School, Ormond Beach Elementary, and Mainland High School. All information and room sizes in this listing are intended to be accurate but cannot be guaranteed. Buyers and their agents are always encouraged to perform due diligence.

1009 Indian Oaks W, Holly Hill

$245,000

Welcome to this single-story, block-construction home in Holly Hill offering 4 bedrooms, 2 full bathrooms and 1,116 square feet of living space. The property sits on a 0.19-acre lot and features tile flooring, central air conditioning, public water and sewer, an attached garage and additional covered carport parking. The practical floor plan provides flexible space for everyday living, guests or a home office. Conveniently located near shopping, dining and major roadways, this home is ready for its next owner. Schedule your private showing today!

4 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 32117 Zip Code

Welcome to this single-story, block-construction home in Holly Hill offering 4 bedrooms, 2 full bathrooms and 1,116 square feet of living space. The property sits on a 0.19-acre lot and features tile flooring, central air conditioning, public water and sewer, an attached garage and additional covered carport parking. The practical floor plan provides flexible space for everyday living, guests or a home office. Conveniently located near shopping, dining and major roadways, this home is ready for its next owner. Schedule your private showing today!

Daytona Beach

$2,300,000

Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and a rare opportunity to create a home tailored to your vision. Surrounded by a lush, expansive yard with ample room for a pool, the property offers exceptional flexibility for its next owner. Enjoy the home's timeless character as it is, or take advantage of the opportunity to create your dream home in one of Sarasota's most established neighborhoods. Inside, a light-filled, open floor plan is complemented by beautiful wood floors and an inviting sense of warmth throughout. The main level features a comfortable guest bedroom with an adjacent full bath, as well as a spacious en-suite primary bedroom, offering the ease and convenience of first-floor living. Upstairs, a private en-suite retreat is filled with character, featuring charming dormer windows, built-in window seats, and extensive storage. Adding to the property's remarkable potential is a recently approved variance along the side of the lot, providing an additional 10 feet of buildable envelope and expanding the possibilities for a future renovation, addition, or new residence. Ideally situated West of the Trail, this exceptional property places you close to top-rated schools, Sarasota Memorial Hospital, the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and vibrant downtown Sarasota. With its coveted location, generous homesite, and unique development potential, this Cherokee Park property presents an extraordinary opportunity to create something truly special.

3 Beds ⋅ 4 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code

Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and a rare opportunity to create a home tailored to your vision. Surrounded by a lush, expansive yard with ample room for a pool, the property offers exceptional flexibility for its next owner. Enjoy the home's timeless character as it is, or take advantage of the opportunity to create your dream home in one of Sarasota's most established neighborhoods. Inside, a light-filled, open floor plan is complemented by beautiful wood floors and an inviting sense of warmth throughout. The main level features a comfortable guest bedroom with an adjacent full bath, as well as a spacious en-suite primary bedroom, offering the ease and convenience of first-floor living. Upstairs, a private en-suite retreat is filled with character, featuring charming dormer windows, built-in window seats, and extensive storage. Adding to the property's remarkable potential is a recently approved variance along the side of the lot, providing an additional 10 feet of buildable envelope and expanding the possibilities for a future renovation, addition, or new residence. Ideally situated West of the Trail, this exceptional property places you close to top-rated schools, Sarasota Memorial Hospital, the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and vibrant downtown Sarasota. With its coveted location, generous homesite, and unique development potential, this Cherokee Park property presents an extraordinary opportunity to create something truly special.

1585 South Drive, Central Sarasota

$2,690,000

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, Central Sarasota

$285,000

Move-in ready and beautifully updated! This 3-bedroom, 2-bath concrete block home offers the perfect blend of comfort and convenience in the desirable Indian Oaks community. The open-concept floor plan features a spacious living area with a cozy brick fireplace and an updated kitchen with granite countertops, stainless steel appliances, and modern finishes. A versatile bonus room is ideal for a home office, playroom, or fitness space. The spacious bedrooms offer generous closet space, while both bathrooms have been tastefully updated. Enjoy the privacy of a fully fenced backyard with plenty of room to entertain, garden, or relax. Conveniently located just minutes from the Halifax River, Ormond Beach, Daytona Beach, shopping, dining, parks, and I-95. Whether you're a first-time homebuyer, downsizing, or searching for an investment property, this home is a must-see!

3 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 32117 Zip Code

Move-in ready and beautifully updated! This 3-bedroom, 2-bath concrete block home offers the perfect blend of comfort and convenience in the desirable Indian Oaks community. The open-concept floor plan features a spacious living area with a cozy brick fireplace and an updated kitchen with granite countertops, stainless steel appliances, and modern finishes. A versatile bonus room is ideal for a home office, playroom, or fitness space. The spacious bedrooms offer generous closet space, while both bathrooms have been tastefully updated. Enjoy the privacy of a fully fenced backyard with plenty of room to entertain, garden, or relax. Conveniently located just minutes from the Halifax River, Ormond Beach, Daytona Beach, shopping, dining, parks, and I-95. Whether you're a first-time homebuyer, downsizing, or searching for an investment property, this home is a must-see!

1013 Indian Oaks E Unit E, Holly Hill

$299,000

This is a beautifully remodeled home so close to everything! Just down the street are the Tangor Outlets, restaurants, I95 and everything Daytona and Ormond Beach have to offer in less than 5 minutes each way.

4 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 32117 Zip Code

This is a beautifully remodeled home so close to everything! Just down the street are the Tangor Outlets, restaurants, I95 and everything Daytona and Ormond Beach have to offer in less than 5 minutes each way.

1003 Cherokee Ranch Road, Holly Hill

$1,549,000

Less than 4 miles to Siesta Key Beach and under 3 miles to Downtown Sarasota, this newly built 4-bed modern home in Sarasota delivers luxury living, investment flexibility, and an exceptional West of the Trail location. Built in 2024, this contemporary residence offers approximately 2,900 square feet with 4 bedrooms+ den and 4.5 baths, featuring open-concept living spaces, clean modern design, energy-efficient construction, and seamless indoor-outdoor flow ideal for entertaining. Located within Sarasota city limits with 7-night minimum rental potential, this property is an outstanding opportunity for both investors and end users seeking a luxury lifestyle close to Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, and Siesta Key Beach. Room for a future pool. Located within the coveted Southside school district.

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

Less than 4 miles to Siesta Key Beach and under 3 miles to Downtown Sarasota, this newly built 4-bed modern home in Sarasota delivers luxury living, investment flexibility, and an exceptional West of the Trail location. Built in 2024, this contemporary residence offers approximately 2,900 square feet with 4 bedrooms+ den and 4.5 baths, featuring open-concept living spaces, clean modern design, energy-efficient construction, and seamless indoor-outdoor flow ideal for entertaining. Located within Sarasota city limits with 7-night minimum rental potential, this property is an outstanding opportunity for both investors and end users seeking a luxury lifestyle close to Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, and Siesta Key Beach. Room for a future pool. Located within the coveted Southside school district.

1734 Wisconsin Lane, Central Sarasota

$6,950,000

Dreaming of breathtaking sunsets? This property is for you! A one of a kind bayfront lot located in highly sought-after Cherokee Park, West of Trail. Located in "X" flood zone this property offers unobstructed panoramic views of Sarasota Bay. The stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a 16,000lb lift and direct access to Sarasota's exceptional boating waters. Enjoy the home as it is or take advantage of this rare opportunity to build a custom waterfront estate on this magnificent property. Offered at $6,990,000, do not miss your chance to own one of Sarasota's finest waterfront locations.

4 Beds ⋅ 4 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code

Dreaming of breathtaking sunsets? This property is for you! A one of a kind bayfront lot located in highly sought-after Cherokee Park, West of Trail. Located in "X" flood zone this property offers unobstructed panoramic views of Sarasota Bay. The stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a 16,000lb lift and direct access to Sarasota's exceptional boating waters. Enjoy the home as it is or take advantage of this rare opportunity to build a custom waterfront estate on this magnificent property. Offered at $6,990,000, do not miss your chance to own one of Sarasota's finest waterfront locations.

1504 S Lodge Drive, Central Sarasota

$12,750,000

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, Central Sarasota