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Virtually Staged. Welcome to 2258 Hillview Street, in the coveted Arlington Park neighborhood. At 2,921 square feet of living space, this 4-bedroom, 4.5-bath home pairs a coastal luxury aesthetic with custom craftsmanship and seamless indoor-outdoor living, all just minutes from Downtown Sarasota and the #1 ranked best beach Siesta Key. Custom built in 2021 and meticulously maintained, this home brings an Old Florida charm to new construction. A covered front porch, soft green shingle-style siding, a red front door, a metal roof, and a paver driveway give it a welcoming, timeless look. As you enter, the space greets you with tall ceilings and expansive impact-rated windows that fill the home with natural light. Gorgeous wide-plank hardwood, smooth textured walls and ceilings, and curated designer finishes keep everything clean and polished. The kitchen is a stunner, with custom wood cabinetry, premium stainless appliances, under-cabinet lighting, a pot filler, and an oversized black walnut butcher block island. Built-in window seats with custom cushions and storage below tuck into the kitchen and the living room nook. The main floor primary suite is a private retreat with a designer wallpaper accent wall and tray ceiling, two walk-in closets with custom closet systems, and sliding doors that open to the pool and patio. The spa-inspired bath has a freestanding soaking tub set against mirrored arabesque glass tile, an oversized marble walk-in shower, and a double vanity with additional storage. The iconic banana leaf wallpaper covered hallway leads to the laundry room, which has teal custom cabinetry, a utility sink, built-in hanging rods, and loads of storage. The powder bath is covered floor to ceiling in blue mosaic tile and has easy access to the pool and patio. The shiplap staircase has hardwood treads and a fun leopard print runner leading to a loft with additional living space. Three more bedrooms with custom closets and beautifully finished baths offer plenty of room. Outside, the saltwater pool has a waterfall, and the covered paver lanai is made for dining and lounging. Mature tropical landscaping, an outdoor shower, and irrigation round out the outdoor space, and a soft water treatment system serves the whole home. An oversized driveway leads back to the gated entry for the detached two-car garage. Arlington Park & Aquatic Complex is nearby, with a 50-meter lap pool, tennis and basketball courts, an outdoor fitness area, a half-mile walking trail, and a dog park. Southside Village has restaurants and shops, and Morton’s Gourmet Market and Sarasota Memorial Hospital are close too. Downtown Sarasota, Siesta Key, Lido Key, and St. Armands Circle are all just minutes away, and there are no HOA fees.

4 Beds ⋅ 5 Baths ⋅ La Linda Terrace SubDv. ⋅ 34239 Zip Code

Virtually Staged. Welcome to 2258 Hillview Street, in the coveted Arlington Park neighborhood. At 2,921 square feet of living space, this 4-bedroom, 4.5-bath home pairs a coastal luxury aesthetic with custom craftsmanship and seamless indoor-outdoor living, all just minutes from Downtown Sarasota and the #1 ranked best beach Siesta Key. Custom built in 2021 and meticulously maintained, this home brings an Old Florida charm to new construction. A covered front porch, soft green shingle-style siding, a red front door, a metal roof, and a paver driveway give it a welcoming, timeless look. As you enter, the space greets you with tall ceilings and expansive impact-rated windows that fill the home with natural light. Gorgeous wide-plank hardwood, smooth textured walls and ceilings, and curated designer finishes keep everything clean and polished. The kitchen is a stunner, with custom wood cabinetry, premium stainless appliances, under-cabinet lighting, a pot filler, and an oversized black walnut butcher block island. Built-in window seats with custom cushions and storage below tuck into the kitchen and the living room nook. The main floor primary suite is a private retreat with a designer wallpaper accent wall and tray ceiling, two walk-in closets with custom closet systems, and sliding doors that open to the pool and patio. The spa-inspired bath has a freestanding soaking tub set against mirrored arabesque glass tile, an oversized marble walk-in shower, and a double vanity with additional storage. The iconic banana leaf wallpaper covered hallway leads to the laundry room, which has teal custom cabinetry, a utility sink, built-in hanging rods, and loads of storage. The powder bath is covered floor to ceiling in blue mosaic tile and has easy access to the pool and patio. The shiplap staircase has hardwood treads and a fun leopard print runner leading to a loft with additional living space. Three more bedrooms with custom closets and beautifully finished baths offer plenty of room. Outside, the saltwater pool has a waterfall, and the covered paver lanai is made for dining and lounging. Mature tropical landscaping, an outdoor shower, and irrigation round out the outdoor space, and a soft water treatment system serves the whole home. An oversized driveway leads back to the gated entry for the detached two-car garage. Arlington Park & Aquatic Complex is nearby, with a 50-meter lap pool, tennis and basketball courts, an outdoor fitness area, a half-mile walking trail, and a dog park. Southside Village has restaurants and shops, and Morton’s Gourmet Market and Sarasota Memorial Hospital are close too. Downtown Sarasota, Siesta Key, Lido Key, and St. Armands Circle are all just minutes away, and there are no HOA fees.

2258 Hillview Street, Sarasota

$524,900

Virtually Staged. Discover the best of Sarasota living at 2142 Waldemere Street, a turnkey furnished home ideally located within the city limits of Sarasota. Offering the flexibility to serve as a full time residence, seasonal retreat, or income producing property, this home combines an exceptional location with valuable recent improvements. Located in Flood Zone X, updates include a new metal roof (2026), new screened porch enclosure (2026), outdoor shower (2026), newer washer and dryer (2025/2026), HVAC system (2023), kitchen appliances (2023), and PVC plumbing. Designed for indoor and outdoor Florida living, the home features a private fenced backyard, spacious screened porch with an outdoor TV, outdoor shower, and mature tropical landscaping. Previously operated as a successful short term rental, the property generated approximately $50,157 in gross rental revenue in 2025 and $55,323 in 2024, with January through April historically renting for approximately $8,000 per month. The location is a standout. Situated within Sarasota city limits, the property allows for 7 day minimum rentals and is conveniently located near Sarasota Memorial Hospital, Hillview's popular dining and shopping, and Arlington Park with its nature trails, tennis courts, dog park, fitness amenities, and community pool. Downtown Sarasota is just minutes away, with Siesta Key and Sarasota's Gulf beaches also within easy reach. Whether you're searching for a full time residence, seasonal Sarasota retreat, or your next investment, this property offers recent improvements, inviting outdoor living, rental flexibility, and a central Sarasota location that is difficult to replicate. Sold as-is. Additional photos coming 10/13.

3 Beds ⋅ 2 Baths ⋅ La Linda Terrace SubDv. ⋅ 34239 Zip Code

Virtually Staged. Discover the best of Sarasota living at 2142 Waldemere Street, a turnkey furnished home ideally located within the city limits of Sarasota. Offering the flexibility to serve as a full time residence, seasonal retreat, or income producing property, this home combines an exceptional location with valuable recent improvements. Located in Flood Zone X, updates include a new metal roof (2026), new screened porch enclosure (2026), outdoor shower (2026), newer washer and dryer (2025/2026), HVAC system (2023), kitchen appliances (2023), and PVC plumbing. Designed for indoor and outdoor Florida living, the home features a private fenced backyard, spacious screened porch with an outdoor TV, outdoor shower, and mature tropical landscaping. Previously operated as a successful short term rental, the property generated approximately $50,157 in gross rental revenue in 2025 and $55,323 in 2024, with January through April historically renting for approximately $8,000 per month. The location is a standout. Situated within Sarasota city limits, the property allows for 7 day minimum rentals and is conveniently located near Sarasota Memorial Hospital, Hillview's popular dining and shopping, and Arlington Park with its nature trails, tennis courts, dog park, fitness amenities, and community pool. Downtown Sarasota is just minutes away, with Siesta Key and Sarasota's Gulf beaches also within easy reach. Whether you're searching for a full time residence, seasonal Sarasota retreat, or your next investment, this property offers recent improvements, inviting outdoor living, rental flexibility, and a central Sarasota location that is difficult to replicate. Sold as-is. Additional photos coming 10/13.

2142 Waldemere Street, Sarasota

$1,890,000

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

5 Beds ⋅ 4 Baths ⋅ La Linda Terrace SubDv. ⋅ 34239 Zip Code

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

2138 Hawthorne Street, Sarasota

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