Homes for Sale Near Sarasota High in Sarasota - 649 homes

Remarks: Welcome to one of Sarasota’s most coveted West of Trail addresses, a location that is truly the heart of everything this city is known and loved for. Nestled just north of Cherokee Park and steps from the Bay, this beautifully updated Florida-style bungalow places you within one of the most established and upscale pockets of Southside Village. This area is known for its walkability, mature tree-lined streets, and a rare blend of history, charm, and coastal convenience. Living here means you are only moments from cherished Sarasota landmarks. Southside Village is right around the corner with Morton’s Gourmet Market, boutique shops, local cafés, and some of the city’s favorite restaurants. McClellan Park, one of Sarasota’s original historic neighborhoods, sits just minutes away and adds to the character and prestige of the surrounding streets. The Bayfront is within easy reach for sunset walks, morning jogs, or peaceful waterfront breaks during the day. This prime address also places you within a short drive of Siesta Key Beach, known for its powdery quartz sand, turquoise water, and consistently top-ranked status among America’s best beaches. Downtown Sarasota is less than ten minutes away, offering world-class dining, art galleries, the opera, theaters, festivals, and the vibrant marina. St. Armands Circle and Lido Beach are also close, perfect for weekend exploring, shopping, or coastal dining nights. Families will appreciate being zoned for the Southside Elementary district, along with proximity to Sarasota Memorial Hospital, local parks, art centers, marinas, and every convenience needed for easy everyday living. Surrounded by prestigious multi-million-dollar homes and some of the most sought-after real estate in Sarasota, this location offers unmatched appeal and long-term value. Inside, the home blends Old World charm with modern comfort. An open, light-filled floor plan features high ceilings, thoughtful updates, and sliding hurricane-rated doors that open to the lush lanai and tropical gardens. Natural light pours through multiple windows, highlighting updated flooring, Italian built-in closets, and contemporary finishes. The surrounding landscaping creates a private retreat ideal for quiet mornings, relaxing afternoons, and cozy evenings outdoors. If you have been searching for a home that pairs character and comfort with an unbeatable West of Trail location, this charming bungalow is one you simply must see.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Kaisen Mitchell (941-726-7657)

Remarks: This exceptional five-bedroom, three-bathroom residence spans 2,468 square feet of living space, offering an inspired floor plan in the gated community of Garden Village. The partially oversized backyard provides ample room to create an outdoor oasis or a large pool. The heart of this remarkable home features a gourmet kitchen with an eat-in dining area, an expansive walk-in pantry, and an oversized island, perfect for entertaining. The first level conveniently offers a main-floor bedroom, while the second story houses the primary bedroom suite complete with an en-suite bathroom, plus three additional bedrooms. Recent updates elevate this home above others on the market, including freshly painted interiors, a new Samsung washer, dryer, and dishwasher installed in August 2025, a brand new AC system installed in March 2026, and a Mitsubishi mini-split system in the garage that provides both air conditioning and heat. Built in 2020, this Garden Village home offers low HOA fees, no CDD, and is not in a flood zone, complemented by modest homeowners association dues that will not strain your budget. The location provides quick access to Interstate 75, Downtown Sarasota, A-rated schools, shopping, and nearby beaches.

Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)

Listing Agent: Mark Quire (941-993-5706)

Remarks: One or more photo(s) has been virtually staged. Nestled near the gentle waters of Roberts Bay, this enchanting Siesta Key home rests on a quiet cul de sac street where the only sounds are the whisper of palms and the laughter of neighbors walking by. T location captures the essence of island life — peaceful, private, and just moments from where the sun dips into the Gulf. A short stroll or quick bike or golf cart ride has you in the center of vibrant Siesta Key. This home is dependable and offers new hurricane impact-rated windows, garage door and sliders; re-lined plumbing lines as well as new pex water supply lines throughout; and a new HVAC system and water heater. Step inside, and you’ll feel the warmth of a home that’s been lovingly renewed. Every detail reflects care and comfort — from the four inviting bedrooms and two full baths to the light-filled kitchen adorned with stainless steel appliances and a captivating blue glass tile backsplash reminiscent of the Gulf waters just moments from your front door. The dining area invites long, easy meals, while two separate living spaces offer versatility for gathering, relaxing, or simply enjoying the rhythm of coastal living. Life is low maintenance and carefree with durable lvp flooring that looks modern and will compliment your coastal décor. Beyond the back door lies a spacious, fenced yard — a blank canvas waiting for your imagination. Picture a pool glimmering under the afternoon sun, a lush garden framed with tropical blooms, or a firepit where evenings stretch into starlit conversations. Here, you aren’t confined to someone else’s vision — you have the freedom to create your own perfect oasis suited to your tastes and dreamy outdoor vibe. The charming front porch welcomes your guests — a cheerful prelude to the life that awaits within. New hurricane-rated windows offer confidence and calm, while the spacious two-car garage with smart epoxy flooring and the generous, indoor laundry room offers convience. This is more than a house; it’s a fresh beginning on Siesta Key — a place where your coastal dream can take root.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)

Listing Agent: Rudy Dudon (941-234-3991)

Remarks: PRICE IMPROVEMENT! An exceptional one-story Allegra home in Sarasota’s coveted West of Trail Flower Streets, perfectly positioned within the Southside School district and just steps from the charming Southside Village restaurants, shops, and Morton’s Gourmet Market. This impeccably designed 3-bedroom + office + bonus room, 2.5-bathroom home epitomizes modern coastal living and showcases the esteemed Kristi Ann single story floor plan, offering a seamless blend of sophisticated design and everyday functionality, making it an ideal primary or seasonal residence. Double doors open to the soaring 18-foot ceiling and wall of expansive 10-foot pocketing sliders which draw you towards the resort-like outdoor retreat, perfect for relaxing or entertaining. The living room features a dramatic floating tray ceiling with Halo-LED lighting and a focal wall complete with a remote-controlled electric fireplace. The chef's kitchen is functional and stylish, equipped with stainless steel appliances, a 5-burner gas range, Quartz island and countertops, and a generous walk-in pantry. The dining area, both intimate and elegant, includes a built-in Quartz-topped buffet, creating a serene space for family meals or hosting guests. The primary suite offers a tranquil escape, with vaulted ceiling accented by charming wood beams. The spacious custom walk-in closet ensures ample storage, while the spa-like en-suite bathroom, featuring glass-enclosed shower and designer tile, is the perfect respite after a long day. Two additional large guest bedrooms, along with a well-appointed guest bathroom and powder room, offer comfort and privacy for family or visitors. This award-winning floorplan also boasts a dedicated office, versatile bonus room, laundry room, and a 2-car AC'd garage with added storage. Step outside and discover an expansive lanai with a resort-style heated pool, spa, and impressive summer kitchen, all surrounded by lush landscaping and illuminated by custom lighting. The disappearing corner sliders seamlessly blend indoor and outdoor spaces, offering the quintessential Sarasota lifestyle. This home is packed with custom features, including designer lighting and built-ins, PGT impact windows, solid-core interior doors, and spray foam insulation for optimal energy efficiency. Recent upgrades include remote-controlled Kevlar shades for additional hurricane protection/storage for outside furnishings/sunshade, new AC unit with UV lights, 2023 mini split AC unit in the garage, and a whole-home in-duct air purifier. Ideally positioned near Southside School, Southside Village, Sarasota Memorial Hospital, Downtown Sarasota, and Siesta Key Beach, it delivers the ultimate blend of location, luxury, and lifestyle. Built to the latest hurricane codes and outside the flood zone, the home provides peace of mind along with timeless design. Every detail has been thoughtfully curated, creating an exceptional opportunity for discerning buyers to experience the best of Sarasota living in a true single-story gem.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Lenore Treiman (941-356-9642)

Remarks: Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.

Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)

Listing Agent: Joel Schemmel (941-587-4894)

Remarks: Under contract-accepting backup offers. Spectacular Bay, Downtown, John Ringling Bridge views and glorious sunsets are yours in this sophisticated 3 bedroom, 3.5 bath Downtown Sarasota residence in the exclusive Tessera condominium, providing a distinguished lifestyle and easy access to all that Sarasota has to offer. Exceeding the highest standards of design, form and function, numerous updates and features offer convenience and refined style and this exceptional home blends the privacy and scale of a single-family residence with the ease and amenities of luxury condominium living. Enter the home through the beautifully appointed double-door foyer, framed by a circular tray ceiling, bespoke chandelier, and gallery-style walls ideal for art and sculpture. The walls of glass bestow best-in-class panoramic views while thoughtful finishes; warm luxury vinyl plank flooring, chic Mica wallpaper, designer lighting, and a fresh coastal palette set a tone of understated sophistication. Walk into the expansive main living area, where floor-to-ceiling sliders optimize Bay views and effortlessly connect to a flexible sitting area—perfect for relaxing, watching the game, or opening to the main space for larger gatherings. The elegant dining area offers stunning Bay vistas that elevate every meal. The kitchen is both functional and inviting, showcasing stone countertops, a double-door refrigerator, dual wall ovens, a large pantry, abundant cabinetry, and a convenient pass through to the dining area. Enter the sprawling primary suite, a private retreat enhanced by its own terrace and a reimagined layout providing his-and-hers bathrooms, dual vanities, two generous walk-in closets, soaking bathtub and a shared marble-and-glass surround shower. Floor-to-ceiling windows frame treetop and Bay views, creating a serene environment from sunrise to sunset. The additional bedrooms offer comfort and privacy, including a guest suite with ensuite bathroom and terrace access, and a second guest bedroom currently serving as a sophisticated office with custom wood built-ins and tailored desk. The convenient guest bath features custom wallpaper and the large laundry room features a brand-new full-size washer and dryer. Solid-core paneled doors, on trend gold hardware, new lighting from Franklin Lighting, and ample storage throughout enhance the home’s effortless livability. Step onto the two sprawling wrap-around terraces—quiet, private, and designed for year-round enjoyment—ideal for dining, lounging, or entertaining among mature live oak canopies or taking in sweeping Bay views and world class sunsets. A rare, oversized private two-car garage with built-in shelving and electrical outlet, an on-floor storage room, and all building water detection system further elevate convenience. Tessera offers exceptional privacy with only two residences per floor and no shared common walls. Amenities include a heated 60-foot pool with sun deck, whirlpool spa, and state-of-the-art fitness center —all fully updated in 2024, along with the lobby and community spaces redesigned by JKL Design. The pet friendly building also offers a grilling area and bicycle storage. Located in the heart of Sarasota’s downtown, just steps from Main Street, Burns Court, the Bayfront, and Selby Gardens, Tessera offers an unparalleled blend of luxury and convenience.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Lenore Treiman (941-356-9642)

Remarks: Positioned along the powdery white sands of Siesta Key’s renowned Crescent Beach, this villa residence within Casa Blanca Beach Resort presents an exceptional opportunity to own in one of Sarasota’s most iconic Gulf-front communities. Casa Blanca is a unique collection of individually owned villas and apartments, each thoughtfully furnished and appointed for effortless coastal living or income-producing flexibility, with minimum rental periods of just 5–7 nights depending on ownership preference. This two-bedroom residence is fully equipped with an updated kitchen and bathroom, all cookware and linens, and the conveniences of individually controlled air conditioning, cable television, and Wi-Fi, creating a seamless turnkey experience for both owners and guests. The community enhances the Gulf-front setting with a clubhouse, pool and multiple on-site laundry facilities, all designed to support easy, resort-style living. Set directly on Crescent Beach, internationally celebrated for its fine, quartz-crystal sand and consistently ranked among the top beaches in the United States, this property captures the essence of Sarasota’s coastal appeal. Ideally situated just off Stickney Point Bridge, it offers effortless access to Sarasota’s renowned dining, shopping, and cultural attractions. With Siesta Beach just steps away, this is a rare opportunity to own in a beloved beachfront destination, whether as a personal retreat, full-time residence, or high-demand investment property.

Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)

Listing Agent: Joel Schemmel (941-587-4894)

Remarks: Modern coastal living in a prime West of the Trail location. This extensively renovated 3-bedroom, 2-bath residence offers nearly 1,900 square feet of bright, open living space with clean finishes and seamless indoor-outdoor flow. Renovations include updated systems, impact windows and doors, and a complete kitchen and bath redesign. The private pool with spa and swim shelf, along with upgraded exterior features, creates a relaxed and functional outdoor setting designed for low-maintenance living. Positioned in one of Sarasota’s most desirable neighborhoods, where new construction and continued demand continue to push values forward, this property captures both lifestyle and long-term potential. No HOA or rental restrictions provide flexibility for full-time use, seasonal enjoyment, or income potential. Currently operating as a successful luxury short-term rental. A standout opportunity in a location that continues to set the pace for Sarasota living.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Ralf Michael Guensch (941-350-3450)

Remarks: Three-Bedroom Pool Home with Great Potential in Ringling Park Located in Sarasota’s established Ringling Park neighborhood, this 3-bedroom, 2-bath home offers solid potential and a fantastic opportunity to make it your own. Set on a spacious pie-shaped lot, the property includes a BRAND-NEW roof, an in-ground caged pool, and ample yard space, fully fenced—perfect for outdoor living or pets. Inside, the layout features a bonus room that can serve as a home office, or flex space. The kitchen is equipped with newer appliances. There is a 1-car garage, extra storage plus a large driveway providing plenty of parking. The location of this home is a true standout—just minutes from downtown Sarasota, local parks, and schools. Whether you're looking for a primary residence, investment, or renovation project, this property offers a great foundation in a highly desirable area. This home is currently rented.

Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)

Listing Agent: Ingrid Caruso (941-539-6233)